Molecules

Editorial

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177 KiB

Open AccessEditorial

Steady Impact Factor Growth for MDPI Open Access Journals

by Alexander Thiesen

Molecules 2012, 17(9), 10971-10973; https://doi.org/10.3390/molecules170910971 - 12 Sep 2012

Viewed by 6546

Abstract

For the past three years MDPI has announced the newly released impact factors for its Open Access journals by the means of an annual editorial [1–3]. In 2012 we are—once again—pleased to report that the growth of the impact factors of MDPI’s Open [...] Read more.

For the past three years MDPI has announced the newly released impact factors for its Open Access journals by the means of an annual editorial [1–3]. In 2012 we are—once again—pleased to report that the growth of the impact factors of MDPI’s Open Access journals continues. This year’s edition of the Journal Citation Reports (JCR), which is published annually by Thomson Reuters, includes 10 journals published by MDPI, including three that have received their first official Impact Factors—International Journal of Environmental Research and Public Health (IJERPH), Materials and Nutrients. Table 1 reports the latest Impact Factors for 2011. Figure 1 graphically depicts the evolution of the Impact Factors for four MDPI open access journals that have received Impact Factors in the past. Table 2 reports the ranking of the MDPI journals within the subject categories of the Science Citation Index Expanded (SCIE). [...] Full article

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Research

Jump to: Editorial, Review, Other

475 KiB

Open AccessArticle

Determination of the Optical GAP in Thin Films of Amorphous Dilithium Phthalocyanine Using the Tauc and Cody Models

by María Elena Sánchez-Vergara, Juan Carlos Alonso-Huitron, Arturo Rodriguez-Gómez and Jerry N. Reider-Burstin

Molecules 2012, 17(9), 10000-10013; https://doi.org/10.3390/molecules170910000 - 24 Aug 2012

Cited by 68 | Viewed by 7626

Abstract

Semiconducting thin films were grown on quartz substrates and crystalline silicon wafers, using dilithium phthalocyanine and the organic ligands 2,6-dihydroxyanthraquinone and 2,6-diaminoanthraquinone as the starting compounds. The films, thus obtained, were characterized by Fourier Transform infrared (FTIR), fast atomic bombardment (FAB+) mass and [...] Read more.

Semiconducting thin films were grown on quartz substrates and crystalline silicon wafers, using dilithium phthalocyanine and the organic ligands 2,6-dihydroxyanthraquinone and 2,6-diaminoanthraquinone as the starting compounds. The films, thus obtained, were characterized by Fourier Transform infrared (FTIR), fast atomic bombardment (FAB+) mass and ultraviolet-visible (UV-Vis) spectroscopies. The surface morphology of these films was analyzed by means of atomic force microscopy (AFM) and scanning electron microscopy (SEM). It was found that the temperature-dependent electric current in all cases showed a semiconductor behavior with conductivities on the order of 10⁻⁶·S cm⁻¹, whereas the highest value corresponded to the thin film based upon the bidentate amine. The Tauc and Cody optical band gap values of thin films were calculated from the absorption coefficients and were found to be around 1.5 eV, with another strong band between 2.3 and 2.43 eV, arising from non-direct transitions. The curvature in the Tauc plot influencing the determination of the optical gap, the Tauc optical gap corresponding to the thicker film is smaller. The dependence of the Cody optical gap on the film thickness was negligible. Full article

(This article belongs to the Special Issue Tetrapyrroles, Porphyrins and Phthalocyanines)

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242 KiB

Open AccessArticle

Synthesis and Biological Activity Evaluation of Novel β-Substituted Nitromethylene Neonicotinoid Analogues

by Baozhu Wang, Jiagao Cheng, Zhiping Xu, Xiaoyong Xu, Xusheng Shao and Zhong Li

Molecules 2012, 17(9), 10014-10025; https://doi.org/10.3390/molecules170910014 - 24 Aug 2012

Cited by 9 | Viewed by 4360

Abstract

The structure-based design and synthesis of a series of novel neonicotinoid analogues are described. The novel neonicotinoid analogues were designed based upon the reaction of enamine derivatives with electron-withdrawing β-substituents with electrophilic thiocyanogen reagents. These compounds were characterized by spectroscopic methods. Bioassays [...] Read more.

The structure-based design and synthesis of a series of novel neonicotinoid analogues are described. The novel neonicotinoid analogues were designed based upon the reaction of enamine derivatives with electron-withdrawing β-substituents with electrophilic thiocyanogen reagents. These compounds were characterized by spectroscopic methods. Bioassays indicated that some of the synthesized compounds exhibited excellent bioactivity against cowpea aphids (Aphis craccivora). The LC₅₀ values of compounds 7, 9, 12, 13, 15, 17, 19, 20 and commercial imidacloprid were 0.01567, 0.00974, 0.02494, 0.01893, 0.02677, 0.01778, 0.0220, 0.02447 and 0.03502 mmol L⁻¹, respectively, which suggested that they could be used as leads for future development of new insecticides. Full article

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439 KiB

Open AccessArticle

Synthesis of Oligonucleotides Carrying Thiol Groups Using a Simple Reagent Derived from Threoninol

by Sonia Pérez-Rentero, Santiago Grijalvo, Rubén Ferreira and Ramon Eritja

Molecules 2012, 17(9), 10026-10045; https://doi.org/10.3390/molecules170910026 - 24 Aug 2012

Cited by 10 | Viewed by 8085

Abstract

Oligonucleotides carrying thiol groups are useful intermediates for a remarkable number of applications involving nucleic acids. In this study, DNA oligonucleotides carrying tert-butylsulfanyl (t-BuS) protected thiol groups have been prepared. A building block derived from threoninol has been developed to [...] Read more.

Oligonucleotides carrying thiol groups are useful intermediates for a remarkable number of applications involving nucleic acids. In this study, DNA oligonucleotides carrying tert-butylsulfanyl (t-BuS) protected thiol groups have been prepared. A building block derived from threoninol has been developed to introduce a thiol group at any predetemined position of an oligonucleotide. The resulting thiolated oligonucleotides have been used for the preparation of oligonucleotide conjugates and for the functionalization of gold nanoparticles using the reactivity of the thiol groups. Full article

(This article belongs to the Special Issue Nucleic Acid Analogs)

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207 KiB

Open AccessArticle

Two New Daucane Sesquiterpenoids from Daphne aurantiaca

by You-Xing Zhao, Sheng-Zhuo Huang, Qing-Yun Ma, Wen-Li Mei and Hao-Fu Dai

Molecules 2012, 17(9), 10046-10051; https://doi.org/10.3390/molecules170910046 - 24 Aug 2012

Cited by 7 | Viewed by 4856

Abstract

Two new daucane sesquiterpenoids 1β,2β-epoxy-10(H)α-dauca-11(12)-ene-7α,14-diol (1) and 1α,2α-epoxy-10(H)α-dauca-11(12)-ene-7α,14-diol (2) were isolated from the plateau medicinal plant Daphne aurantiaca Diels. (Thymelaeceae). Their structures were elucidated by 1D and 2D NMR spectroscopy, as well as HR-ESI-MS data. Full article

(This article belongs to the Section Natural Products Chemistry)

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358 KiB

Open AccessArticle

Formononetin Attenuates IL-1β-Induced Apoptosis and NF-κB Activation in INS-1 Cells

by Yao Wang, Yunxia Zhu, Lu Gao, Han Yin, Zuoling Xie, Dong Wang, Zhengqiu Zhu and Xiao Han

Molecules 2012, 17(9), 10052-10064; https://doi.org/10.3390/molecules170910052 - 24 Aug 2012

Cited by 63 | Viewed by 6810

Abstract

Several studies suggest that the inflammation plays a role in the pathogenesis of some glucose disorders in adults. Exposure of pancreatic β-cells to cytokines, such as interleukin-1β (IL-1β), is thought to contribute to β-cell apoptosis. One important event triggered by IL-1β is induction [...] Read more.

Several studies suggest that the inflammation plays a role in the pathogenesis of some glucose disorders in adults. Exposure of pancreatic β-cells to cytokines, such as interleukin-1β (IL-1β), is thought to contribute to β-cell apoptosis. One important event triggered by IL-1β is induction of nitric oxide synthase (iNOS), an enzyme that catalyzes intracellular generation of the cytotoxic free radical NO. Recent work have suggested that formononetin, as an O-methylated isoflavone found in a number of plants and herbs like Astragalus membranaceus, inhibited some pro-inflammatory cytokine production in macrophages. However, the roles of formononetin in pancreatic beta cells have not been fully established. The aim of the present study was to assess possible in vitro effects of formononetin on cell apoptosis induced by IL-1β in the rat insulinoma cell line, INS-1. Our results demonstrate that formononetin significantly prevents IL-1β-increased INS-1 cell death and blocks cytokine-induced apoptotic signaling (the reduction of Bax/Bcl-2 ratio and caspase-3 activity). Formononetin also inhibited the activation of nuclear factor-kappaB (NF-κB), which is a significant transcription factor for iNOS, so as to decease nitric oxide (NO) formation in a dose dependent manner in vitro. Our observations indicated that formononetin could protect against pancreatic β-cell apoptosis caused by IL-1β and therefore could be used in the future as a new drug improving diabetes mellitus. Full article

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211 KiB

Open AccessCommunication

Inhibition of Burkholderia multivorans Adhesion to Lung Epithelial Cells by Bivalent Lactosides

by Ciara Wright, Rosaria Leyden, Paul V. Murphy, Máire Callaghan, Trinidad Velasco-Torrijos and Siobhán McClean

Molecules 2012, 17(9), 10065-10071; https://doi.org/10.3390/molecules170910065 - 24 Aug 2012

Cited by 2 | Viewed by 5503

Abstract

Burkholderia cepacia complex (Bcc) is an opportunistic pathogen in cystic fibrosis patients which is inherently resistant to antimicrobial agents. The mechanisms of attachment and pathogenesis of Bcc, a group of 17 species, are poorly understood. The most commonly identified Bcc species in newly [...] Read more.

Burkholderia cepacia complex (Bcc) is an opportunistic pathogen in cystic fibrosis patients which is inherently resistant to antimicrobial agents. The mechanisms of attachment and pathogenesis of Bcc, a group of 17 species, are poorly understood. The most commonly identified Bcc species in newly colonised patients, Burkholderia multivorans, continues to be acquired from the environment. Development of therapies which can prevent or reduce the risk of colonization on exposure to Bcc in the environment would be a better alternative to antimicrobial agents. Previously, it has been shown that Bcc strains bound to many glycolipid receptors on lung epithelia. Using a real-time PCR method to quantify the levels of binding of B. multivorans to the lung epithelial cells, we have examined glycoconjugate derivatives for their potential to inhibit host cell attachment. Bivalent lactosides previously shown to inhibit galectin binding significantly reduced the attachment of B. multivorans to CF lung epithelial cells at micromolar concentrations. This was in contrast to monosaccharides and lactose, which were only effective in the millimolar range. Development of glycoconjugate therapies such as these, which inhibit attachment to lung epithelial cells, represent an alternative means of preventing infection with inherently antimicrobially resistant pathogens such as B. multivorans. Full article

(This article belongs to the Special Issue Advances in Carbohydrate Chemistry 2012)

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376 KiB

Open AccessCommunication

A New Cubitane Diterpenoid from the Soft Coral Sinularia crassa

by Ching-Hsiao Cheng, Yun-Sheng Lin, Zhi-Hong Wen and Jui-Hsin Su

Molecules 2012, 17(9), 10072-10078; https://doi.org/10.3390/molecules170910072 - 24 Aug 2012

Cited by 10 | Viewed by 4848

Abstract

A new cubitane diterpenoid, crassalone A (1), was isolated from the marine soft coral Sinularia crassa. The structure was determined by extensive spectroscopic analyses. Compound 1 is not cytotoxic (IC₅₀ > 20 μg/mL) toward the four human cancer cell [...] Read more.

A new cubitane diterpenoid, crassalone A (1), was isolated from the marine soft coral Sinularia crassa. The structure was determined by extensive spectroscopic analyses. Compound 1 is not cytotoxic (IC₅₀ > 20 μg/mL) toward the four human cancer cell lines tested (HL60, MDA-MB-231, HCT-116 and DLD-1). Full article

(This article belongs to the Section Natural Products Chemistry)

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419 KiB

Open AccessArticle

4-Ferrocenylpyridine- and 4-Ferrocenyl-3-ferrocenylmethyl-3,4-dihydropyridine-3,5-dicarbonitriles: Multi-Component Synthesis, Structures and Electrochemistry

by Elena I. Klimova, Marcos Flores-Alamo, Sandra Cortez Maya, Mark E. Martínez, Luis Ortiz-Frade and Tatiana Klimova

Molecules 2012, 17(9), 10079-10093; https://doi.org/10.3390/molecules170910079 - 24 Aug 2012

Cited by 11 | Viewed by 4814

Abstract

The reactions of 2-cyano-3-ferrocenylacrylonitrile (1) with malononitrile (2) in a MeOH/H₂O or 2-PrOH/H₂O medium in the presence of Na₂CO₃ afforded 6-alkoxy-2-amino-4-ferrocenylpyridine-3,5-dicarbonitriles 3a,b (multi-component condensation) and 6-alkoxy-2-amino-4-ferrocenyl-3-ferrocenylmethyl-3,4-dihydropyridine-3,5-dicarbonitriles 4a,b (multi-component [...] Read more.

The reactions of 2-cyano-3-ferrocenylacrylonitrile (1) with malononitrile (2) in a MeOH/H₂O or 2-PrOH/H₂O medium in the presence of Na₂CO₃ afforded 6-alkoxy-2-amino-4-ferrocenylpyridine-3,5-dicarbonitriles 3a,b (multi-component condensation) and 6-alkoxy-2-amino-4-ferrocenyl-3-ferrocenylmethyl-3,4-dihydropyridine-3,5-dicarbonitriles 4a,b (multi-component cyclodimerization). Analogous reactions of 1 with 2 in an MeOH/H₂O medium in the presence of NaOH, piperidine, or morpholine gave compounds 3a, 4a and 2-amino-4-ferrocenyl-6-hydroxy-, 6-piperidino- and 6-morpholinopyridine-3,5-dicarbonitriles 3c–e, respectively. The structures of the compounds 3b, 4a and 4b were established by the spectroscopic data and X-ray diffraction analysis. The electrochemical behaviour of compounds 3b, 3d and 4b was investigated by means of cyclic voltammetry. Full article

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910 KiB

Open AccessArticle

Activity of Spray-dried Microparticles Containing Pomegranate Peel Extract against Candida albicans

by Eliana Harue Endo, Tânia Ueda-Nakamura, Celso Vataru Nakamura and Benedito Prado Dias Filho

Molecules 2012, 17(9), 10094-10107; https://doi.org/10.3390/molecules170910094 - 24 Aug 2012

Cited by 42 | Viewed by 6604

Abstract

Pomegranate has attracted interest from researchers because of its chemical composition and biological properties. It possesses strong antioxidant activity, with potential health benefits, and also antimicrobial properties. The aim of this study was to produce microparticles containing pomegranate extract by the spray-drying technique, [...] Read more.

Pomegranate has attracted interest from researchers because of its chemical composition and biological properties. It possesses strong antioxidant activity, with potential health benefits, and also antimicrobial properties. The aim of this study was to produce microparticles containing pomegranate extract by the spray-drying technique, utilizing alginate or chitosan as encapsulating agents. Characterization and antifungal assays were carried out. Production yields were about 40% for alginate microparticles and 41% for chitosan. Mean diameters were 2.45 µm and 2.80 µm, and encapsulation efficiencies were 81.9% and 74.7% for alginate and chitosan microparticles, respectively. The spray-drying process preserved the antifungal activity against Candida albicans. These results could be useful for developing dosage forms for treating candidiasis, and should be further investigated in in vivo models. Full article

(This article belongs to the Section Natural Products Chemistry)

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282 KiB

Open AccessArticle

Ameliorative Effects of Curculigoside from Curculigo orchioides Gaertn on Learning and Memory in Aged Rats

by Xiu-Ying Wu, Jian-Zhong Li, Jian-Zheng Guo and Bao-Yuan Hou

Molecules 2012, 17(9), 10108-10118; https://doi.org/10.3390/molecules170910108 - 24 Aug 2012

Cited by 32 | Viewed by 6190

Abstract

This study was designed to evaluate the ameliorating effects of curculigoside from Curculigo orchioides Gaertn on learning and memory in aged rats. In the present study, the ameliorating effects of curculigoside were determined through animal behaviour studies (including step-down test and Y-maze test), [...] Read more.

This study was designed to evaluate the ameliorating effects of curculigoside from Curculigo orchioides Gaertn on learning and memory in aged rats. In the present study, the ameliorating effects of curculigoside were determined through animal behaviour studies (including step-down test and Y-maze test), and the possible mechanisms were explored by evaluation of the activity of acetylcholinesterase (AchE) and determination of the expression of BACE1. Oral adminstration of the curculigoside (20, 40 mg/kg/day) for 14 days can significantly improve the latency and number of errors in aged rats based on the behaviour study results. In addition, the activity of AchE can be decreased by treatment of the curculigoside (10, 20, 40 mg/kg/day). Moreover, the expression of BACE1 can be down-regulated in the hippocampus of aged rats treated with curculigoside. The results of our present work have indicated that curculigoside can improve cognitive function in aged animals, possibly by decreasing the activity of AchE in the cerebra and inhibiting the expression of BACE1 in the hippocampus. In conclusion, our results suggested that curculigoside can be possible developed as a new drug for the treatment of Alzheimer’s disease in the future. Full article

(This article belongs to the Section Natural Products Chemistry)

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1946 KiB

Open AccessArticle

Dry Etching of Copper Phthalocyanine Thin Films: Effects on Morphology and Surface Stoichiometry

by Jaron G. Van Dijken and Michael J. Brett

Molecules 2012, 17(9), 10119-10130; https://doi.org/10.3390/molecules170910119 - 24 Aug 2012

Cited by 6 | Viewed by 7524

Abstract

We investigate the evolution of copper phthalocyanine thin films as they are etched with argon plasma. Significant morphological changes occur as a result of the ion bombardment; a planar surface quickly becomes an array of nanopillars which are less than 20 nm in [...] Read more.

We investigate the evolution of copper phthalocyanine thin films as they are etched with argon plasma. Significant morphological changes occur as a result of the ion bombardment; a planar surface quickly becomes an array of nanopillars which are less than 20 nm in diameter. The changes in morphology are independent of plasma power, which controls the etch rate only. Analysis by X-ray photoelectron spectroscopy shows that surface concentrations of copper and oxygen increase with etch time, while carbon and nitrogen are depleted. Despite these changes in surface stoichiometry, we observe no effect on the work function. The absorbance and X-ray diffraction spectra show no changes other than the peaks diminishing with etch time. These findings have important implications for organic photovoltaic devices which seek nanopillar thin films of metal phthalocyanine materials as an optimal structure. Full article

(This article belongs to the Special Issue Tetrapyrroles, Porphyrins and Phthalocyanines)

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373 KiB

Open AccessArticle

Mechanistic Study of the Spiroindolones: A New Class of Antimalarials

by Bin Zou, Peiling Yap, Louis-Sebastian Sonntag, Seh Yong Leong, Bryan K. S. Yeung and Thomas H. Keller

Molecules 2012, 17(9), 10131-10141; https://doi.org/10.3390/molecules170910131 - 24 Aug 2012

Cited by 34 | Viewed by 6816

Abstract

During the synthesis of the new antimalarial drug candidate NITD609, a high degree of diastereoselectivity was observed in the Pictet-Spengler reaction. By isolating both the 4E and 4Z imine intermediates, a systematic mechanistic study of the reaction under both kinetic and [...] Read more.

During the synthesis of the new antimalarial drug candidate NITD609, a high degree of diastereoselectivity was observed in the Pictet-Spengler reaction. By isolating both the 4E and 4Z imine intermediates, a systematic mechanistic study of the reaction under both kinetic and thermodynamic conditions was conducted. This study provides insight into the source of the diastereoselectivity for this important class of compounds. Full article

(This article belongs to the Special Issue Spiro Compounds)

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531 KiB

Open AccessArticle

Acetylcholinesterase-Inhibiting Activity of Salicylanilide N-Alkylcarbamates and Their Molecular Docking

by Ales Imramovsky, Sarka Stepankova, Jan Vanco, Karel Pauk, Juana Monreal-Ferriz, Jarmila Vinsova and Josef Jampilek

Molecules 2012, 17(9), 10142-10158; https://doi.org/10.3390/molecules170910142 - 24 Aug 2012

Cited by 46 | Viewed by 7166

Abstract

A series of twenty-five novel salicylanilide N-alkylcarbamates were investigated as potential acetylcholinesterase inhibitors. The compounds were tested for their ability to inhibit acetylcholinesterase (AChE) from electric eel (Electrophorus electricus L.). Experimental lipophilicity was determined, and the structure-activity relationships are discussed. The [...] Read more.

A series of twenty-five novel salicylanilide N-alkylcarbamates were investigated as potential acetylcholinesterase inhibitors. The compounds were tested for their ability to inhibit acetylcholinesterase (AChE) from electric eel (Electrophorus electricus L.). Experimental lipophilicity was determined, and the structure-activity relationships are discussed. The mode of binding in the active site of AChE was investigated by molecular docking. All the discussed compounds expressed significantly higher AChE inhibitory activity than rivastigmine and slightly lower than galanthamine. Disubstitution by chlorine in C'_(3,4) of the aniline ring and the optimal length of hexyl-undecyl alkyl chains in the carbamate moiety provided the most active AChE inhibitors. Monochlorination in C'₍₄₎ exhibited slightly more effective AChE inhibitors than in C'₍₃₎. Generally it can be stated that compounds with higher lipophilicity showed higher inhibition, and the activity of the compounds is strongly dependent on the length of the N-alkyl chain. Full article

(This article belongs to the Section Medicinal Chemistry)

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956 KiB

Open AccessArticle

Distribution of Primary and Specialized Metabolites in Nigella sativa Seeds, a Spice with Vast Traditional and Historical Uses

by Ilan Botnick, Wentao Xue, Einat Bar, Mwafaq Ibdah, Amnon Schwartz, Daniel M. Joel, Efraim Lev, Aaron Fait and Efraim Lewinsohn

Molecules 2012, 17(9), 10159-10177; https://doi.org/10.3390/molecules170910159 - 24 Aug 2012

Cited by 79 | Viewed by 9140

Abstract

Black cumin (Nigella sativa L., Ranunculaceae) is an annual herb commonly used in the Middle East, India and nowadays gaining worldwide acceptance. Historical and traditional uses are extensively documented in ancient texts and historical documents. Black cumin seeds and oil are commonly [...] Read more.

Black cumin (Nigella sativa L., Ranunculaceae) is an annual herb commonly used in the Middle East, India and nowadays gaining worldwide acceptance. Historical and traditional uses are extensively documented in ancient texts and historical documents. Black cumin seeds and oil are commonly used as a traditional tonic and remedy for many ailments as well as in confectionery and bakery. Little is known however about the mechanisms that allow the accumulation and localization of its active components in the seed. Chemical and anatomical evidence indicates the presence of active compounds in seed coats. Seed volatiles consist largely of olefinic and oxygenated monoterpenes, mainly p-cymene, thymohydroquinone, thymoquinone, γ-terpinene and α-thujene, with lower levels of sesquiterpenes, mainly longifolene. Monoterpene composition changes during seed maturation. γ-Terpinene and α-thujene are the major monoterpenes accumulated in immature seeds, and the former is gradually replaced by p-cymene, carvacrol, thymo-hydroquinone and thymoquinone upon seed development. These compounds, as well as the indazole alkaloids nigellidine and nigellicine, are almost exclusively accumulated in the seed coat. In contrast, organic and amino acids are primarily accumulated in the inner seed tissues. Sugars and sugar alcohols, as well as the amino alkaloid dopamine and the saponin α-hederin accumulate both in the seed coats and the inner seed tissues at different ratios. Chemical analyses shed light to the ample traditional and historical uses of this plant. Full article

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542 KiB

Open AccessArticle

A Synthetic Method to Access Symmetric and Non-Symmetric 2-(N,N'-disubstituted)guanidinebenzothiazoles

by Alejandro Cruz, Itzia I. Padilla-Martínez and Efrén V. García-Báez

Molecules 2012, 17(9), 10178-10191; https://doi.org/10.3390/molecules170910178 - 24 Aug 2012

Cited by 8 | Viewed by 7056

Abstract

Symmetric and non-symmetric 2-(N-H, N-methyl, N-ethylenyl and N-aryl)guanidinebenzothiazoles were synthesized from the reaction of ammonia, methylamine, pyrrolidine and aniline with dimethyl benzo[d]thiazol-2-yl-carbono-dithioimidate (5) as intermediate. The products were characterized by ¹H-, ¹³C-NMR [...] Read more.

Symmetric and non-symmetric 2-(N-H, N-methyl, N-ethylenyl and N-aryl)guanidinebenzothiazoles were synthesized from the reaction of ammonia, methylamine, pyrrolidine and aniline with dimethyl benzo[d]thiazol-2-yl-carbono-dithioimidate (5) as intermediate. The products were characterized by ¹H-, ¹³C-NMR spectroscopy and three of them by X-ray diffraction analysis. HN-phenyl protons formed intramolecular hydrogen bonds that assist the stereochemistry of the second substituent, whereas the HN-alkyl protons were involved in intermolecular hydrogen bonding. Full article

(This article belongs to the Section Organic Chemistry)

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Open AccessArticle

Chemical Composition of Essential Oil from Italian Populations of Artemisia alba Turra (Asteraceae)

by Antonella Maggio, Sergio Rosselli, Maurizio Bruno, Vivienne Spadaro, Francesco Maria Raimondo and Felice Senatore

Molecules 2012, 17(9), 10232-10241; https://doi.org/10.3390/molecules170910232 - 27 Aug 2012

Cited by 40 | Viewed by 5091

Abstract

The use of essential oils as chemotaxonomic markers could be useful for the classification of Artemisia species and to caracterize biodiversity in the different populations. An analysis of the chemical composition of four essential oils from Italian populations of Artemisia alba Turra (collected [...] Read more.

The use of essential oils as chemotaxonomic markers could be useful for the classification of Artemisia species and to caracterize biodiversity in the different populations. An analysis of the chemical composition of four essential oils from Italian populations of Artemisia alba Turra (collected in Sicily, Marche and Abruzzo) was investigated. In this paper an in depth study of the significant differences observed in the composition of these oils is reported. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Identification and Determination of Aconitum Alkaloids in Aconitum Herbs and Xiaohuoluo Pill Using UPLC-ESI-MS

by Ping Cui, Han Han, Rui Wang and Li Yang

Molecules 2012, 17(9), 10242-10257; https://doi.org/10.3390/molecules170910242 - 27 Aug 2012

Cited by 17 | Viewed by 5922

Abstract

A rapid, specific, and sensitive ultra-performance liquid chromatography-electrospray ionization-mass spectrometry (UPLC-ESI-MS) method to examine the chemical differences between Aconitum herbs and processed products has been developed and validated. Combined with chemometrics analysis of principal component analysis (PCA) and orthogonal projection to latent structural [...] Read more.

A rapid, specific, and sensitive ultra-performance liquid chromatography-electrospray ionization-mass spectrometry (UPLC-ESI-MS) method to examine the chemical differences between Aconitum herbs and processed products has been developed and validated. Combined with chemometrics analysis of principal component analysis (PCA) and orthogonal projection to latent structural discriminate analysis, diester-diterpenoid and monoester-type alkaloids, especially the five alkaloids which contributed to the chemical distinction between Aconitum herbs and processed products, namely mesaconitine (MA), aconitine (AC), hypaconitine (HA), benzoylmesaconitine (BMA), and benzoylhypaconitine (BHA), were picked out. Further, the five alkaloids and benzoylaconitine (BAC) have been simultaneously determined in the Xiaohuoluo pill. Chromatographic separations were achieved on a C₁₈ column and peaks were detected by mass spectrometry in positive ion mode and selected ion recording (SIR) mode. In quantitative analysis, the six alkaloids showed good regression, (r) > 0.9984, within the test ranges. The lower limit quantifications (LLOQs) for MA, AC, HA, BMA, BAC, and BHA were 1.41, 1.20, 1.92, 4.28, 1.99 and 2.02 ng·mL⁻¹, respectively. Recoveries ranged from 99.7% to 101.7%. The validated method was applied successfully in the analysis of the six alkaloids from different samples, in which significant variations were revealed. Results indicated that the developed assay can be used as an appropriate quality control assay for Xiaohuoluo pill and other herbal preparations containing Aconitum roots. Full article

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Open AccessArticle

The Effect of Camphor and Borneol on Rat Thymocyte Viability and Oxidative Stress

by Emiliya Cherneva, Voja Pavlovic, Andrija Smelcerovic and Denitsa Yancheva

Molecules 2012, 17(9), 10258-10266; https://doi.org/10.3390/molecules170910258 - 27 Aug 2012

Cited by 35 | Viewed by 7630

Abstract

Camphor and borneol are wildly distributed in the essential oils of medicinal plants from various parts of the World. Our study has been carried out to evaluate the effect of these two bicyclic monoterpenes on rat thymocytes. Camphor and borneol at concentrations of [...] Read more.

Camphor and borneol are wildly distributed in the essential oils of medicinal plants from various parts of the World. Our study has been carried out to evaluate the effect of these two bicyclic monoterpenes on rat thymocytes. Camphor and borneol at concentrations of 0.5 and 5 µg/mL did not induce significant toxicity on the immune system cells, while a significant increase of thymocyte viability was detected when cells were incubated with 50 µg/mL of camphor. A significant increase of cell viability was similarly detected when thymocytes were cultivated with borneol at concentrations of 0.5 and 5 µg/mL. The role of camphor and borneol in reactive oxygen species (ROS) production and mitochondrial membrane potential (MMP) disturbances in rat thymocytes as well as their potential mechanism(s) of action were also discussed. Full article

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Open AccessArticle

Evaluation of in Vivo Antioxidant and Immunity Enhancing Activities of Sodium Aescinate Injection Liquid

by Yong-Kun Wang, Jiang Han, Wu-Jun Xiong, Qiong-Ying Yuan, Yan-Ping Gu, Jun Li, Zhe Zhu, Hui Zhang and Cong-Jun Wang

Molecules 2012, 17(9), 10267-10275; https://doi.org/10.3390/molecules170910267 - 27 Aug 2012

Cited by 26 | Viewed by 5289

Abstract

Oxidative stress is involved in the development and progression of disease. Because sodium aescinate has been reported to have immunity enhancing and antioxidative effects, we investigated its activity by employing a hepatocellular carcinoma (HCC) mouse model. Sixty BALB/c mice were randomly divided into [...] Read more.

Oxidative stress is involved in the development and progression of disease. Because sodium aescinate has been reported to have immunity enhancing and antioxidative effects, we investigated its activity by employing a hepatocellular carcinoma (HCC) mouse model. Sixty BALB/c mice were randomly divided into four groups, including a 1.4 mg/kg treated group (n = 15), a 2.8 mg/kg treated group (n = 15), an untreated hepatocellular carcinoma control group (n = 15) and a normal control group (n = 15). After H22 cells were cultured for one week, we collected 2 × 10⁶ cells and injected them subcutaneously as 0.2 mL cell suspensions in sterile saline into the right shoulder region of every mouse. The animals were monitored for changes in activity, physical condition and body weight during the experiment. The next day after injection of H22 cells, animals in these test groups received one intraperitoneal injection of drug or physiological saline for 13 days. Results showed that in the sodium aescinate injection liquid (SAIL)-treated HCC mice, serum interleukin-1 beta (IL-1β), interleukin-6 (IL-6), tumor necrosis factor-alpha (TNF-α), interferon-gamma (IFN-γ), Gamma-glutamyltransferase (γ-GT), alanine transaminase (ALT), aspartate transaminase (AST) and alkaline phosphatase (ALP) levels were significantly decreased compared with normal control mice. In addition, treatment with sodium aescinate injection liquid significantly decreased blood and liver malondialdehyde (MDA) levels, increased glutathione (GSH) levels, and antioxidant enzyme [superoxide dismutase (SOD), catalase (CAT) and glutathione peroxidase (GSH-Px)] activities in a dose-dependent manner. We conclude that sodium aescinate injection liquid can decrease oxidative injury and enhance immunity functions in HCC mice. Full article

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Open AccessArticle

Antimicrobial Activity of Geranium Oil against Clinical Strains of Staphylococcus aureus

by Monika Bigos, Małgorzata Wasiela, Danuta Kalemba and Monika Sienkiewicz

Molecules 2012, 17(9), 10276-10291; https://doi.org/10.3390/molecules170910276 - 28 Aug 2012

Cited by 48 | Viewed by 15859

Abstract

The aim of this work was to investigate the antibacterial properties of geranium oil obtained from Pelargonium graveolens Ait. (family Geraniaceae), against one standard S. aureus strain ATCC 433000 and seventy clinical S. aureus strains. The agar dilution method was used for [...] Read more.

The aim of this work was to investigate the antibacterial properties of geranium oil obtained from Pelargonium graveolens Ait. (family Geraniaceae), against one standard S. aureus strain ATCC 433000 and seventy clinical S. aureus strains. The agar dilution method was used for assessment of bacterial growth inhibition at various concentrations of geranium oil. Susceptibility testing of the clinical strains to antibiotics was carried out using the disk-diffusion and E-test methods. The results of our experiment showed that the oil from P. graveolens has strong activity against all of the clinical S. aureus isolates—including multidrug resistant strains, MRSA strains and MLS_B-positive strains—exhibiting MIC values of 0.25–2.50 μL/mL. Full article

(This article belongs to the Special Issue Macromolecules Applied to Pharmaceutics)

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Open AccessArticle

Compositional Study and Antioxidant Potential of Ipomoea hederacea Jacq. and Lepidium sativum L. Seeds

by Muhammad Zia-Ul-Haq, Shakeel Ahmad, Luca Calani, Teresa Mazzeo, Daniele Del Rio, Nicoletta Pellegrini and Vincenzo De Feo

Molecules 2012, 17(9), 10306-10321; https://doi.org/10.3390/molecules170910306 - 29 Aug 2012

Cited by 96 | Viewed by 7824

Abstract

The present investigation has been carried out to determine the proximate composition, amino acids, metal contents, oil composition as well as the antioxidant capacity of the seeds of Ipomoea hederacea Jacq. and Lepidium sativum L. Proximate composition indicated a great difference in oil [...] Read more.

The present investigation has been carried out to determine the proximate composition, amino acids, metal contents, oil composition as well as the antioxidant capacity of the seeds of Ipomoea hederacea Jacq. and Lepidium sativum L. Proximate composition indicated a great difference in oil (14.09 ± 0.66, 28.03 ± 1.05) and fibre (16.55 ± 0.31, 6.75 ± 1.20) contents for I. hederacea and L. sativum, respectively. Fatty acid profile indicated that oleic acid (19.50 ± 0.37, 30.50 ± 0.16) and linoleic acid (52.09 ± 0.48, 8.60 ± 0.38) are the major fatty acids. γ-Tocopherol and d-tocopherol (28.70 ± 0.14, 111.56 ± 0.37) were the most abundant in the seed oil of I. hederacea and L. sativum, respectively. Results of TEAC, FRAP and TRAP antioxidant assays indicated that L. sativum has much greater antioxidant potential than I. hederacea. Full article

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Open AccessArticle

Antibacterial and Synergy of Berberines with Antibacterial Agents against Clinical Multi-Drug Resistant Isolates of Methicillin-Resistant Staphylococcus aureus (MRSA)

by Guo-Ying Zuo, Yang Li, Jun Han, Gen-Chun Wang, Yun-Ling Zhang and Zhong-Qi Bian

Molecules 2012, 17(9), 10322-10330; https://doi.org/10.3390/molecules170910322 - 29 Aug 2012

Cited by 44 | Viewed by 6050

Abstract

Antibacterial activity of berberine (Ber) and 8-acetonyl-dihydroberberine (A-Ber) alone and combined uses with antibacterial agents ampicillin (AMP), azithromycin (AZM), cefazolin (CFZ) and levofloxacin (LEV) was studied on 10 clinical isolates of SCCmec III type methicillin-resistant Staphylococcus aureus (MRSA). Susceptibility to each agent alone [...] Read more.

Antibacterial activity of berberine (Ber) and 8-acetonyl-dihydroberberine (A-Ber) alone and combined uses with antibacterial agents ampicillin (AMP), azithromycin (AZM), cefazolin (CFZ) and levofloxacin (LEV) was studied on 10 clinical isolates of SCCmec III type methicillin-resistant Staphylococcus aureus (MRSA). Susceptibility to each agent alone was tested using a broth microdilution method and the chequerboard and time-kill tests for the combined evaluations, respectively. The alone MICs/MBCs (mg/mL) ranges were 32–128/64–256 (Ber) and 32-128/128-512 (A-Ber). Significant synergies were observed for the Ber (A-Ber)/AZM and Ber (A-Ber)/LEV combinations against 90% of the tested MRSA strains, with fractional inhibitory concentration indices (FICIs) values ranged from 0.188 to 0.500. An additivity result was also observed for the Ber/AZM combination by time-kill curves. These results demonstrated for the first time that Ber and A-Ber enhanced the in vitro inhibitory efficacy of AZM and LEV to a same extent, which had potential for further investigation in combinatory therapeutic applications of patients infected with MRSA. Full article

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Open AccessArticle

Design and Synthesis of New Chacones Substituted with Azide/Triazole Groups and Analysis of Their Cytotoxicity Towards HeLa Cells

by Graziele D. Da Silva, Marina G. Da Silva, Estrela M. P. V. E. Souza, Andersson Barison, Sarah C. Simões, Fernando P. Varotti, Leandro A. Barbosa, Gustavo H. R. Viana and José A. F. P. Villar

Molecules 2012, 17(9), 10331-10343; https://doi.org/10.3390/molecules170910331 - 29 Aug 2012

Cited by 30 | Viewed by 5718

Abstract

A series of new chalcones substituted with azide/triazole groups were designed and synthesized, and their cytotoxic activity was evaluated in vitro against the HeLa cell line. O-Alkylation, Claisen-Schmidt condensation and Cu(I)-catalyzed cycloaddition of azides with terminal alkynes were applied in key steps. [...] Read more.

A series of new chalcones substituted with azide/triazole groups were designed and synthesized, and their cytotoxic activity was evaluated in vitro against the HeLa cell line. O-Alkylation, Claisen-Schmidt condensation and Cu(I)-catalyzed cycloaddition of azides with terminal alkynes were applied in key steps. Fifteen compounds were tested against HeLa cells. Compound 8c was the most active molecule, with an IC₅₀ value of 13.03 µM, similar to the value of cisplatin (7.37 µM). Full article

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Open AccessArticle

Preparation of Dry Extract of Mikania glomerata Sprengel (Guaco) and Determination of Its Coumarin Levels by Spectrophotometry and HPLC-UV

by Luciana Soares e Silva, Luciane Santos da Silva, Larissa Brumano, Paulo César Stringheta, Miriam Aparecida de Oliveira Pinto, Leticia Oliveira Moreira Dias, Camila De Sá Martins Muller, Elita Scio, Rodrigo Luiz Fabri, Helena C. Castro and Maria Da Penha Henriques do Amaral

Molecules 2012, 17(9), 10344-10354; https://doi.org/10.3390/molecules170910344 - 29 Aug 2012

Cited by 17 | Viewed by 9931

Abstract

Guaco (Mikania glomerata Sprengel) syrup is one of the most popular herbal medicines used to treat the symptoms of asthmatic bronchitis, cough and hoarseness. The coumarin 2H-1-benzopyran-2-one, is one of the major constituents of Guaco and contributes to its pharmacological [...] Read more.

Guaco (Mikania glomerata Sprengel) syrup is one of the most popular herbal medicines used to treat the symptoms of asthmatic bronchitis, cough and hoarseness. The coumarin 2H-1-benzopyran-2-one, is one of the major constituents of Guaco and contributes to its pharmacological effects. The pharmaceutical capsule form of dry extract of Guaco is recommended by the Brazilian Program of Medicinal Plants and Herbal Medicines and used in primary health care. In order to identify a new protocol to obtain the raw material for Guaco capsule production we evaluated two methods, including a freeze-drying process (lyophilization) and the spray-dryer technique, as well as the use of two adjuvants, Maltodextrins and Aerosil^®, in different concentrations. The coumarin levels of the dried extracts were analyzed by UV-spectrophotometry and HPLC-UV/DAD. The adjuvant Aerosil^® 8% showed better dry powder physical appearance. Lyophilization was observed to be the best process to obtain the dry extract of Guaco based on the measured coumarin levels. Full article

(This article belongs to the Special Issue Coumarins and Xanthones)

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Open AccessArticle

The Dual Action of Epigallocatechin Gallate (EGCG), the Main Constituent of Green Tea, against the Deleterious Effects of Visible Light and Singlet Oxygen-Generating Conditions as Seen in Yeast Cells

by Radu Mitrica, Ioana Dumitru, Lavinia L. Ruta, Augustin M. Ofiteru and Ileana C. Farcasanu

Molecules 2012, 17(9), 10355-10369; https://doi.org/10.3390/molecules170910355 - 29 Aug 2012

Cited by 19 | Viewed by 6794

Abstract

Green tea extracts (GTEs) as well as their main component, the polyphenol epigallocatechin gallate (EGCG), are known for their versatile antioxidant, antimicrobial, antitumoral or anti-inflammatory effects. In spite of the huge beneficial action, there is increasing evidence that under certain conditions green tea [...] Read more.

Green tea extracts (GTEs) as well as their main component, the polyphenol epigallocatechin gallate (EGCG), are known for their versatile antioxidant, antimicrobial, antitumoral or anti-inflammatory effects. In spite of the huge beneficial action, there is increasing evidence that under certain conditions green tea and its components can be detrimental to living organisms. Using Saccharomyces cerevisiae strains with various defects in the response to oxidative stress, we found that GTEs or EGCG act in synergy with visible light, exhibiting either deleterious or protective effects depending on the solvent employed. Similar synergistic effects could be observed under singlet oxygen-generating conditions, such as light exposure in the presence of photosensitizers or UV-A irradiation, therefore solvent variance may represent a powerful tool to modulate the preparation of green tea extracts, depending on the intended target. Full article

(This article belongs to the Special Issue Antioxidants 2012)

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Open AccessArticle

Antiviral Effect of Matrine against Human Enterovirus 71

by Yajun Yang, Jinghui Xiu, Xu Zhang, Liangfeng Zhang, Kai Yan, Chuan Qin and Jiangning Liu

Molecules 2012, 17(9), 10370-10376; https://doi.org/10.3390/molecules170910370 - 29 Aug 2012

Cited by 72 | Viewed by 6110

Abstract

Human enterovirus 71, a member of the Picornaviridae family, is one of the major causative agent of hand, foot and mouth disease in children less than six years old. This illness has caused mortalities in large-scale outbreaks in the Asia-Pacific region in recent [...] Read more.

Human enterovirus 71, a member of the Picornaviridae family, is one of the major causative agent of hand, foot and mouth disease in children less than six years old. This illness has caused mortalities in large-scale outbreaks in the Asia-Pacific region in recent years. No vaccine or antiviral therapy is available. In this study, antiviral effect of matrine against enterovirus 71 were evaluated in vitro and in vivo. Matrine could suppress the viral RNA copy number on rhabdomyosarcoma cells. Moreover, matrine treatment of mice challenged with a lethal dose of enterovirus 71 reduced the mortality and relieved clinical symptoms. The results showed that matrine may represent a potential therapeutic agent for enterovirus 71 infection. Full article

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Open AccessArticle

Novel Pyranopyrazoles: Synthesis and Theoretical Studies

by Ahmed A. Al-Amiery, Redah I. Al-Bayati, Fouad M. Saed, Wassan B. Ali, Abdul Amir H. Kadhum and Abu Bakar Mohamad

Molecules 2012, 17(9), 10377-10389; https://doi.org/10.3390/molecules170910377 - 30 Aug 2012

Cited by 33 | Viewed by 5735

Abstract

A series of pyranopyrazoles, namely, 7-(2-aminoethyl)-3,4-dimethyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (2), (Z)-3,4-dimethyl-1-(4-((4-nitrobenzylidene)amino)phenyl)pyrano[2,3-c]pyrazol-6(1H)-one (5), 1-(4-(3,4-dimethyl-6-oxopyrano[2,3-c]pyrazol-1(6H)-yl)phenyl)-3-(naphthalen-1-yl)urea (6), (Z)-ethyl 4-((3,4-dimethyl-6-oxo-1,6-dihydropyrano[2,3-c]pyrazol-5-yl)diazenyl)benzoate (8) and 3,4-dimethyl-N-(naphthalen-1-yl)-6-oxopyrano[2,3-c]pyrazole-1(6H)-carboxamide (9) were synthesized [...] Read more.

A series of pyranopyrazoles, namely, 7-(2-aminoethyl)-3,4-dimethyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (2), (Z)-3,4-dimethyl-1-(4-((4-nitrobenzylidene)amino)phenyl)pyrano[2,3-c]pyrazol-6(1H)-one (5), 1-(4-(3,4-dimethyl-6-oxopyrano[2,3-c]pyrazol-1(6H)-yl)phenyl)-3-(naphthalen-1-yl)urea (6), (Z)-ethyl 4-((3,4-dimethyl-6-oxo-1,6-dihydropyrano[2,3-c]pyrazol-5-yl)diazenyl)benzoate (8) and 3,4-dimethyl-N-(naphthalen-1-yl)-6-oxopyrano[2,3-c]pyrazole-1(6H)-carboxamide (9) were synthesized and characterized by means of their UV-VIS, FT-IR, ¹H-NMR and ¹³C-NMR spectral data. Density Functional Theory calculations of the synthesized pyranopyrazoles were performed using molecular structures with optimized geometries. Molecular orbital calculations have provided detail description of the orbitals, including spatial characteristics, nodal patterns, and the contributions of individual atoms. Full article

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Open AccessArticle

A Comparison of Fruit Chemical Characteristics of Two Wild Grown Rubus Species from Different Locations of Croatia

by Dubravka Dujmović Purgar, Boris Duralija, Sandra Voća, Aleš Vokurka and Sezai Ercisli

Molecules 2012, 17(9), 10390-10398; https://doi.org/10.3390/molecules170910390 - 30 Aug 2012

Cited by 31 | Viewed by 5209

Abstract

The main focus of our study was to investigate differences in nutritional (dry matter, soluble solids content, total acidity and pH value) and bioactive values (ascorbic acid, total anthocyanins, total phenols, and non-flavonoids content) of wild grown raspberry (Rubus idaeus) and [...] Read more.

The main focus of our study was to investigate differences in nutritional (dry matter, soluble solids content, total acidity and pH value) and bioactive values (ascorbic acid, total anthocyanins, total phenols, and non-flavonoids content) of wild grown raspberry (Rubus idaeus) and blackberry (Rubus discolor) genotypes harvested from native populations in Croatia. The average total acidity ranged from 0.93 to 1.72% in R. discolor and 1.57 to 1.91% in R. idaeus. Ascorbic acid was found between 22.34 mg and 45.00 mg 100 g⁻¹ in R. idaeus, while it was between 30.64 mg and 33.09 mg 100 g⁻¹ in R. discolor genotypes. A great variability in total anthocyanins was detected in Croatian wild blackberry and raspberry genotypes, ranging from 2,226 to 2,367 mg kg⁻¹ for blackberries and 279 to 582 mg kg⁻¹ for raspberries, indicating wild blackberries are particularly rich in anthocyanins. On the basis of these results, it can be concluded that investigated wild growing fruit species have a great potential in nutritive research, as well as in biodiversity research. It is necessary to carry out further investigation and evaluation of wild growing fruit species to utilize them in the most appropriate way, as well as conservation of interesting accessions in the gene banks. Full article

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Open AccessArticle

Cloning, Phylogenetic Analysis and 3D Modeling of a Putative Lysosomal Acid Lipase from the Camel, Camelus dromedarius

by Farid Shokry Ataya

Molecules 2012, 17(9), 10399-10413; https://doi.org/10.3390/molecules170910399 - 30 Aug 2012

Cited by 5 | Viewed by 4542

Abstract

Acid lipase belongs to a family of enzymes that is mainly present in lysosomes of different organs and the stomach. It is characterized by its capacity to withstand acidic conditions while maintaining high lipolytic activity. We cloned for the first time the full [...] Read more.

Acid lipase belongs to a family of enzymes that is mainly present in lysosomes of different organs and the stomach. It is characterized by its capacity to withstand acidic conditions while maintaining high lipolytic activity. We cloned for the first time the full coding sequence of camel’s lysosomal acid lipase, cLIPA using RT-PCR technique (Genbank accession numbers JF803951 and AEG75815, for the nucleotide and aminoacid sequences respectively). The cDNA sequencing revealed an open reading frame of 1,197 nucleotides that encodes a protein of 399 aminoacids which was similar to that from other related mammalian species. Bioinformatic analysis was used to determine the aminoacid sequence, 3D structure and phylogeny of cLIPA. Bioinformatics analysis suggested the molecular weight of the translated protein to be 45.57 kDa, which could be decreased to 43.16 kDa after the removal of a signal peptide comprising the first 21 aminoacids. The deduced cLIPA sequences exhibited high identity with Equus caballus (86%), Numascus leucogenys (85%), Homo sapiens (84%), Sus scrofa (84%), Bos taurus (82%) and Ovis aries (81%). cLIPA shows high aminoacid sequence identity with human and dog-gastric lipases (58%, and 59% respectively) which makes it relevant to build a 3D structure model for cLIPA. The comparison confirms the presence of the catalytic triad and the oxyanion hole in cLIPA. Phylogenetic analysis revealed that camel cLIPA is grouped with monkey, human, pig, cow and goat. The level of expression of cLIPA in five camel tissues was examined using Real Time-PCR. The highest level of cLIPA transcript was found in the camel testis (162%), followed by spleen (129%), liver (100%), kidney (20.5%) and lung (17.4%). Full article

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Open AccessArticle

Synthesis, Structure and Insecticidal Activities of Some Novel Amides Containing N-Pyridylpyrazole Moeities

by Wei-Li Dong, Jing-Ying Xu, Li-Xia Xiong and Zheng-Ming Li

Molecules 2012, 17(9), 10414-10428; https://doi.org/10.3390/molecules170910414 - 31 Aug 2012

Cited by 24 | Viewed by 7108

Abstract

In our search for environmentally benign insecticides with high activity, low toxicity and low residue, a novel series of amides containing N-pyridylpyrazole moieties were designed and synthesized. The structures of the title compounds were characterized and confirmed by ¹H-NMR and elemental [...] Read more.

In our search for environmentally benign insecticides with high activity, low toxicity and low residue, a novel series of amides containing N-pyridylpyrazole moieties were designed and synthesized. The structures of the title compounds were characterized and confirmed by ¹H-NMR and elemental analysis. Furthermore, the structure of compound 7l was determined by single crystal X-ray diffraction. The preliminary bioassay tests showed that some of them exhibited good insecticidal activities against Mythimna separata Walker, Plutella xylostella (Linnaeus, 1758) and Laphygma exigua Hübner. Full article

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Open AccessArticle

Computational Prediction of Blood-Brain Barrier Permeability Using Decision Tree Induction

by Claudia Suenderhauf, Felix Hammann and Jörg Huwyler

Molecules 2012, 17(9), 10429-10445; https://doi.org/10.3390/molecules170910429 - 31 Aug 2012

Cited by 86 | Viewed by 10076

Abstract

Predicting blood-brain barrier (BBB) permeability is essential to drug development, as a molecule cannot exhibit pharmacological activity within the brain parenchyma without first transiting this barrier. Understanding the process of permeation, however, is complicated by a combination of both limited passive diffusion and [...] Read more.

Predicting blood-brain barrier (BBB) permeability is essential to drug development, as a molecule cannot exhibit pharmacological activity within the brain parenchyma without first transiting this barrier. Understanding the process of permeation, however, is complicated by a combination of both limited passive diffusion and active transport. Our aim here was to establish predictive models for BBB drug permeation that include both active and passive transport. A database of 153 compounds was compiled using in vivo surface permeability product (logPS) values in rats as a quantitative parameter for BBB permeability. The open source Chemical Development Kit (CDK) was used to calculate physico-chemical properties and descriptors. Predictive computational models were implemented by machine learning paradigms (decision tree induction) on both descriptor sets. Models with a corrected classification rate (CCR) of 90% were established. Mechanistic insight into BBB transport was provided by an Ant Colony Optimization (ACO)-based binary classifier analysis to identify the most predictive chemical substructures. Decision trees revealed descriptors of lipophilicity (aLogP) and charge (polar surface area), which were also previously described in models of passive diffusion. However, measures of molecular geometry and connectivity were found to be related to an active drug transport component. Full article

(This article belongs to the Special Issue QSAR and Its Applications)

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Open AccessArticle

Simple Synthesis of Modafinil Derivatives and Their Anti-inflammatory Activity

by Jae-Chul Jung, Yeonju Lee, Jee-Young Son, Eunyoung Lim, Mankil Jung and Seikwan Oh

Molecules 2012, 17(9), 10446-10458; https://doi.org/10.3390/molecules170910446 - 3 Sep 2012

Cited by 31 | Viewed by 8557

Abstract

Simple synthesis of modafinil derivatives and their biological activity are described. The key synthetic strategies involve substitution and coupling reactions. We determined the anti-inflammatory effects of modafinil derivatives in cultured BV2 cells by measuring the inhibition of nitrite production and expression of iNOS [...] Read more.

Simple synthesis of modafinil derivatives and their biological activity are described. The key synthetic strategies involve substitution and coupling reactions. We determined the anti-inflammatory effects of modafinil derivatives in cultured BV2 cells by measuring the inhibition of nitrite production and expression of iNOS and COX-2 after LPS stimulation. It was found that for sulfide analogues introduction of aliphatic groups on the amide part (compounds 11a–d) resulted in lower anti-inflammatory activity compared with cyclic or aromatic moieties (compounds 11e–k). However, for the sulfoxide analogues, introduction of aliphatic moieties (compounds 12a–d) showed higher anti-inflammatory activity than cyclic or aromatic fragments (compounds 12e–k) in BV-2 microglia cells. Full article

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Open AccessArticle

Fumigant Antifungal Activity of Myrtaceae Essential Oils and Constituents from Leptospermum petersonii against Three Aspergillus Species

by Eunae Kim and Il-Kwon Park

Molecules 2012, 17(9), 10459-10469; https://doi.org/10.3390/molecules170910459 - 3 Sep 2012

Cited by 71 | Viewed by 7140

Abstract

Commercial plant essential oils obtained from 11 Myrtaceae plant species were tested for their fumigant antifungal activity against Aspergillus ochraceus, A. flavus, and A. niger. Essential oils extracted from Leptospermum petersonii at air concentrations of 56 × 10⁻³ mg/mL [...] Read more.

Commercial plant essential oils obtained from 11 Myrtaceae plant species were tested for their fumigant antifungal activity against Aspergillus ochraceus, A. flavus, and A. niger. Essential oils extracted from Leptospermum petersonii at air concentrations of 56 × 10⁻³ mg/mL and 28 × 10⁻³ mg/mL completely inhibited the growth of the three Aspergillus species. However, at an air concentration of 14 × 10⁻³ mg/mL, inhibition rates of L. petersonii essential oils were reduced to 20.2% and 18.8% in the case of A. flavus and A. niger, respectively. The other Myrtaceae essential oils (56 × 10⁻³ mg/mL) only weakly inhibited the fungi or had no detectable affect. Gas chromatography-mass spectrometry analysis identified 16 compounds in L. petersonii essential oil. The antifungal activity of the identified compounds was tested individually by using standard or synthesized compounds. Of these, neral and geranial inhibited growth by 100%, at an air concentration of 56 × 10⁻³ mg/mL, whereas the activity of citronellol was somewhat lover (80%). The other compounds exhibited only moderate or weak antifungal activity. The antifungal activities of blends of constituents identified in L. petersonii oil indicated that neral and geranial were the major contributors to the fumigant and antifungal activities. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Structural Characterization and Identification of Major Constituents in Jitai Tablets by High-Performance Liquid Chromatography/Diode-Array Detection Coupled with Electrospray Ionization Tandem Mass Spectrometry

by Shuping Wang, Lei Liu, Lingling Wang, Yaohua Hu, Weidong Zhang and Runhui Liu

Molecules 2012, 17(9), 10470-10493; https://doi.org/10.3390/molecules170910470 - 3 Sep 2012

Cited by 70 | Viewed by 8300

Abstract

In the present study a universally applicable HPLC-DAD/ESI-MS/MS method was developed for carrying out the comprehensive characterization of Jitai tablets (JTT). Based on the ESI-MSⁿ fragmentation patterns of the reference standards, a total of 101 components were identified or tentatively characterized by [...] Read more.

In the present study a universally applicable HPLC-DAD/ESI-MS/MS method was developed for carrying out the comprehensive characterization of Jitai tablets (JTT). Based on the ESI-MSⁿ fragmentation patterns of the reference standards, a total of 101 components were identified or tentatively characterized by comparing their retention times, UV and MS spectra with those of reference standards or through the matching of empirical information with those of published components in the in-house library. The characteristic fragmentation pattern of alkaloids, phenolic acids, tanshinones, flavonoid glycosides, cyanogenic glycosides, ginsenosides, 2-(2-phenylethyl) chromones, phthalides and gingerol-related compounds were tentatively elucidated using structurally-relevant product ions. It was observed that neutral losses of C₉H₁₀O₃ and C₉H₈O₂ were the characteristic product ions of scopola alkaloids. Neutral fragment mandelonitrile was the characteristic ion of cyanogenic glycosides. To our knowledge, tropylium ionand C₄H₂O unit were the characteristic ions of 2-(2-phenylethyl) chromone, which resulted from the Retro-Diels-Alder (RDA) cleavage of the C ring. The results indicated that the developed analysis method could be employed as a rapid, effective technique for structural characterization of chemical constituents in TCM. This work is expected to provide comprehensive information for the quality evaluation and pharmacokinetic studies of JTT. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Steroidal and Phenolic Glycosides from the Bulbs of Lilium pumilum DC and Their Potential Na⁺/K⁺ ATPase Inhibitory Activity

by Zhong-Liu Zhou, Zong-Cai Feng, Chun-Yan Fu, Hua-Lin Zhang and Jing-Min Xia

Molecules 2012, 17(9), 10494-10502; https://doi.org/10.3390/molecules170910494 - 3 Sep 2012

Cited by 28 | Viewed by 4756

Abstract

A new steroidal saponin, named pumilum A (1), and a new phenolic glycoside, threo-1-(4′-hydroxy-2′-methoxyphenyl)-2-(2′′,4′′-dihydroxyphenyl)-1,3-propanediol-4′-O-β-D-glucopyranoside (7) were isolated from the methanolic extract of the bulbs of Lilium pumilum DC, along with five known steroidal saponins. [...] Read more.

A new steroidal saponin, named pumilum A (1), and a new phenolic glycoside, threo-1-(4′-hydroxy-2′-methoxyphenyl)-2-(2′′,4′′-dihydroxyphenyl)-1,3-propanediol-4′-O-β-D-glucopyranoside (7) were isolated from the methanolic extract of the bulbs of Lilium pumilum DC, along with five known steroidal saponins. Their chemical structures were elucidated on the basis of detailed spectroscopic analysis, including 1D and 2D NMR techniques and chemical methods. In addition, the inhibitory activity of all the isolates on Na⁺/K⁺ ATPase was evaluated. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Antibacterial and Antioxidant Potency of Floral Honeys from Different Botanical and Geographical Origins

by Hasan A. Alzahrani, Rashid Alsabehi, Laïd Boukraâ, Fatiha Abdellah, Yuva Bellik and Balkees A. Bakhotmah

Molecules 2012, 17(9), 10540-10549; https://doi.org/10.3390/molecules170910540 - 4 Sep 2012

Cited by 95 | Viewed by 9905

Abstract

In order to assess their physicochemical and antioxidant properties as well as their antimicrobial potency, four varieties of honey from different botanical and geographical origins were used. The agar incorporation method was used to determine the antimicrobial potency of honeys. The total phenol [...] Read more.

In order to assess their physicochemical and antioxidant properties as well as their antimicrobial potency, four varieties of honey from different botanical and geographical origins were used. The agar incorporation method was used to determine the antimicrobial potency of honeys. The total phenol content was determined by a modified Folin–Ciocalteu method and the free radical scavenging activity by the Fe³⁺ reducing power (FRAP) assay. Manuka honey was the most effective against Staphylococcus aureus Oxa R and S. aureus Oxa S with a Minimum Inhibitory Concentration (MIC) of 6% and 7%, respectively, whereas wild carrot honey was the most effective against Pseudomonas aeruginosa, with a MIC of 12%. Lavender honey was the least effective against all tested strains, even though was found to have the lowest pH and water content. Manuka honey had the highest content of polyphenols, with 899.09 ± 11.75 mg gallic acid/kg, whereas lavender honey had the lowest, with 111.42 ± 3.54 mg gallic acid/kg. A very significant correlation (r value was 0.9079 at P < 0.05) was observed between the total polyphenolic content and the Fe²⁺ content formed in the presence of the honey antioxidants. The differences between honey samples in terms of antibacterial and antioxidant activity could be attributed to the natural variations in floral sources of nectar and the different locations. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Effects of Velvet Antler with Blood on Bone in Ovariectomized Rats

by Sung-Hui Tseng, Hsin-Ching Sung, Lih-Geeng Chen, Ying-Jang Lai, Kun-Teng Wang, Chun-Hsien Sung and Ching-Chiung Wang

Molecules 2012, 17(9), 10574-10585; https://doi.org/10.3390/molecules170910574 - 5 Sep 2012

Cited by 19 | Viewed by 6862

Abstract

In traditional Chinese medicine (TCM), both velvet antlers (VA) and VA blood can tonify qi, essence, and marrow, nourish the blood, and invigorate bones and tendons. In TCM, the combination of VA and VA blood is believed to have superior pharmacological effects. Scientific [...] Read more.

In traditional Chinese medicine (TCM), both velvet antlers (VA) and VA blood can tonify qi, essence, and marrow, nourish the blood, and invigorate bones and tendons. In TCM, the combination of VA and VA blood is believed to have superior pharmacological effects. Scientific evidence supporting the traditional therapeutic preference for redder antler is needed. The effectiveness of the combination therapy of VA middle sections (VAMs) and VA blood (VAM-B) was first examined in promoting proliferation of mouse osteoblastic cells (MC3T3-E1). The anti-osteoporotic activity of VAM-B (ratio of VAM:VA blood = 1:0.2) was evaluated with ovariectomized (OVX) rats at a dose of 0.2 g/kg. In VAM-B-treated OVX rats, the body weight decreased 10.7%, and the strength of vertebrae and the femur respectively increased 18.1% and 15.4%, compared to the control. VAM-B treatment also recovered the estrogen-related loss of the right tibial trabecular bone microarchitecture. Alkaline phosphatase (ALP) significantly decreased, but estradiol did not significantly change in serum of VAM-B-treated OVX rats. We also provide an effective strategy to enhance the anti-osteoporotic activity of VAM. In conclusion, our results provide scientific evidence supporting the traditional therapeutic preference of redder antler and indicate that VAM-B is a potential therapeutic agent for managing osteoporosis. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Design, Practical Synthesis, and Biological Evaluation of Novel 6-(Pyrazolylmethyl)-4-quinoline-3-carboxylic Acid Derivatives as HIV-1 Integrase Inhibitors

by Liming Hu, Song Yan, Zaigang Luo, Xiao Han, Yujie Wang, Zhanyang Wang and Chengchu Zeng

Molecules 2012, 17(9), 10652-10666; https://doi.org/10.3390/molecules170910652 - 6 Sep 2012

Cited by 21 | Viewed by 5213

Abstract

A series of novel 6-(pyrazolylmethyl)-4-oxo-4H-quinoline-3-carboxylic acid derivatives bearing different substituents on the N-position of quinoline ring were designed and synthesized as potential HIV-1 integrase (IN) inhibitors, based on the structurally related GS-9137 scaffold. The structures of all new compounds were confirmed [...] Read more.

A series of novel 6-(pyrazolylmethyl)-4-oxo-4H-quinoline-3-carboxylic acid derivatives bearing different substituents on the N-position of quinoline ring were designed and synthesized as potential HIV-1 integrase (IN) inhibitors, based on the structurally related GS-9137 scaffold. The structures of all new compounds were confirmed by ¹H-NMR, ¹³C-NMR and ESI (or HRMS) spectra. Detailed synthetic protocols and the anti-IN activity studies are also presented. Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessArticle

Synthesis and Protective Effect of Scutellarein on Focal Cerebral Ischemia/Reperfusion in Rats

by Lihua Qian, Minzhe Shen, Hao Tang, Yuping Tang, Li Zhang, Yifan Fu, Qianping Shi and Nian-Guang Li

Molecules 2012, 17(9), 10667-10674; https://doi.org/10.3390/molecules170910667 - 6 Sep 2012

Cited by 51 | Viewed by 5304

Abstract

Scutellarein, the main metabolite of scutellarin in vivo, has relatively better solubility, bioavailability and bio-activity than scutellarin. However, compared with scutellarin, it is very difficult to obtain scutellarein from Nature. Therefore, the present study focused on establishing an efficient route for the [...] Read more.

Scutellarein, the main metabolite of scutellarin in vivo, has relatively better solubility, bioavailability and bio-activity than scutellarin. However, compared with scutellarin, it is very difficult to obtain scutellarein from Nature. Therefore, the present study focused on establishing an efficient route for the synthesis of scutellarein by hydrolyzing scutellarin. Neurological deficit score and cerebral infarction volume with the administration of scutellarein were then used to compare its neuroprotective effects on focal cerebral ischemia/reperfusion in rats induced by middle cerebral artery occlusion (MCAO) with those of scutellarin. The results showed that scutellarein had better protective effect on focal cerebral ischemia/reperfusion than scutellarin, which laid the foundation for further research and development of scutellarein as a promising candidate for ischemic cerebro-vascular disease. Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessArticle

Activity-Guided Isolation of Antioxidant Compounds from Rhizophora apiculata

by Mingzhe Gao and Hongbin Xiao

Molecules 2012, 17(9), 10675-10682; https://doi.org/10.3390/molecules170910675 - 6 Sep 2012

Cited by 25 | Viewed by 5496

Abstract

Rhizophora apiculata (R. apiculata) contains an abundance of biologically active compounds due its special salt-tolerant living surroundings. In this study, the total phenolic content and antioxidant activities of various extract and fractions of stem of R. apiculata were investigated. Results indicated [...] Read more.

Rhizophora apiculata (R. apiculata) contains an abundance of biologically active compounds due its special salt-tolerant living surroundings. In this study, the total phenolic content and antioxidant activities of various extract and fractions of stem of R. apiculata were investigated. Results indicated that butanol fraction possesses the highest total phenolic content (181.84 mg/g GAE/g dry extract) with strongest antioxidant abilities. Following in vitro antioxidant activity-guided phytochemical separation procedures, lyoniresinol-3α-O-β-arabinopyranoside (1), lyoniresinol-3α-O-β-rhamnoside (2), and afzelechin-3-O-L-rhamno-pyranoside (3) were separated from the butanol fraction. These compounds showed more noticeable antioxidant activity than a BHT standard in the DPPH, ABTS and hydroxyl radical scavenging assays. HPLC analysis results showed that among different plant parts, the highest content of 1–3 was located in the bark (0.068%, 0.066% and 0.011%, respectively). The results imply that the R. apiculata might be a potential source of natural antioxidants and 1–3 are antioxidant ingredients in R. apiculata. Full article

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Open AccessArticle

Regiocontrolled Microwave Assisted Bifunctionalization of 7,8-Dihalogenated Imidazo[1,2-a]pyridines: A One Pot Double-Coupling Approach

by Emilie Marie, Sébastien Bouclé, Cécile Enguehard-Gueiffier and Alain Gueiffier

Molecules 2012, 17(9), 10683-10707; https://doi.org/10.3390/molecules170910683 - 6 Sep 2012

Cited by 7 | Viewed by 5095

Abstract

The reactivity of the 7-chloro-8-iodo- and 8-chloro-7-iodoimidazo[1,2-a]pyridines 1a–e diversely substituted on the 2 position, towards Suzuki-Miyaura, Sonogashira, and Buchwald-Hartwig cross-coupling reactions as well as cyanation was evaluated. Various methodologies are proposed to introduce aryl, heteroaryl, alkyne, amine or cyano [...] Read more.

The reactivity of the 7-chloro-8-iodo- and 8-chloro-7-iodoimidazo[1,2-a]pyridines 1a–e diversely substituted on the 2 position, towards Suzuki-Miyaura, Sonogashira, and Buchwald-Hartwig cross-coupling reactions as well as cyanation was evaluated. Various methodologies are proposed to introduce aryl, heteroaryl, alkyne, amine or cyano groups in the two positions depending on the nature of the substituent present in position 2. In both series, the substitution of the iodine atom was totally regioselective and the difficulty was to substitute the chlorine atom in a second step. Until now, only hetero(aryl) groups could be introduced though Suzuki-Miyaura cross-coupling. We overcame this problem evaluating both regioisomers in parallel. The double coupling approach was also studied allowing the one pot Suzuki/Suzuki, cyanation/Sonogashira and cyanation/Buchwald reactions leading to polyfunctionnalized imidazo[1,2-a]pyridines. Full article

(This article belongs to the Section Organic Chemistry)

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Open AccessArticle

An Improved Synthesis of 1,2-Diarylethanols under Conventional Heating and Ultrasound Irradiation

by Dong-Mei Gao, Wei-Li Ma, Tian-Rui Li, Liang-Zhu Huang and Zhen-Ting Du

Molecules 2012, 17(9), 10708-10715; https://doi.org/10.3390/molecules170910708 - 7 Sep 2012

Cited by 12 | Viewed by 4544

Abstract

A simple and efficient synthesis of 1,2-diarylethanols has been developed. The procedure involved the reaction between a variety of toluene derivatives and aryl aldehydes under conventional heating and ultrasound irradiation. This procedure possesses several advantages such as operational simplicity, high yield, safety and [...] Read more.

A simple and efficient synthesis of 1,2-diarylethanols has been developed. The procedure involved the reaction between a variety of toluene derivatives and aryl aldehydes under conventional heating and ultrasound irradiation. This procedure possesses several advantages such as operational simplicity, high yield, safety and environment benignancy. Ultrasound was proved to be very helpful to the reaction, markedly improving the yield and the reaction rate. Full article

(This article belongs to the Section Organic Chemistry)

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Open AccessArticle

Development and Characterization of EST-SSR Markers from Scapharca broughtonii and Their Transferability in Scapharca subcrenata and Tegillarca granosa

by Meng Li, Ling Zhu, Chun-Ya Zhou, Lin Lin, Yan-Jun Fan and Zhi-Meng Zhuang

Molecules 2012, 17(9), 10716-10723; https://doi.org/10.3390/molecules170910716 - 7 Sep 2012

Cited by 12 | Viewed by 4823

Abstract

Twenty-five novel EST-derived simple sequence repeat (EST-SSR) markers were developed in the ark shell Scapharca broughtonii. Polymorphisms of these EST-SSR markers were evaluated in 48 wild individuals collected from Shidao, Shandong Province, China. A total of 202 alleles were detected at 25 [...] Read more.

Twenty-five novel EST-derived simple sequence repeat (EST-SSR) markers were developed in the ark shell Scapharca broughtonii. Polymorphisms of these EST-SSR markers were evaluated in 48 wild individuals collected from Shidao, Shandong Province, China. A total of 202 alleles were detected at 25 loci. The numbers of alleles per locus ranged from 4 to 14, with an average of 8.08. The observed and expected heterozygosities varied from 0.2917 to 1.000 and from 0.3570 to 0.9002, respectively. After sequential Bonferroni correction for multiple tests, only one locus was found to deviate from Hardy-Weinberg equilibrium. Twenty-five EST-SSR markers showed a high rate of across-species transferability (100%) in Scapharca subcrenata and a low rate of across-genus transferability (20%) in Tegillarca granosa. These EST-SSRs will be helpful for QTL mapping, molecular breeding and investigation of population genetic diversity in ark shell S. broughtonii and other Scapharca species. Full article

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Open AccessArticle

Phenolic Antioxidants Isolated from the Flowers of Osmanthus fragrans

by Chien-Ya Hung, Yu-Cheng Tsai and Kuo-Yu Li

Molecules 2012, 17(9), 10724-10737; https://doi.org/10.3390/molecules170910724 - 7 Sep 2012

Cited by 68 | Viewed by 9783

Abstract

O. fragrans has slightly less antioxidative activity than green tea. Five phenolic compounds, tyrosyl acetate (1), (+)-phillygenin (2), (8E)-ligustroside (3), rutin (4), and verbascoside (5), were isolated from the CHCl₃ [...] Read more.

O. fragrans has slightly less antioxidative activity than green tea. Five phenolic compounds, tyrosyl acetate (1), (+)-phillygenin (2), (8E)-ligustroside (3), rutin (4), and verbascoside (5), were isolated from the CHCl₃ sub-extract of O. fragrans. The structures were elucidated by interpreting their spectral data. Evaluation of the antioxidative property of the isolated (+)-phillygenin (2), rutin (4), and verbascoside (5) revealed strong DPPH radical scavenging activity, with IC₅₀ values of 19.1, 10.3, and 6.2 μM, respectively. These isolates also exhibited an H₂O₂ scavenging ability, with IC₅₀ values of 10.5, 23.4, and 13.4 μM, respectively. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Novel Lipophilic Lanthanide Bis-Phthalocyanines Functionalized by Pentadecylphenoxy Groups: Synthesis, Characterization and UV-Photostability

by Rudolf Słota, Gabriela Dyrda, Maria Hofer, Giuseppe Mele, Ermelinda Bloise and Roberta del Sole

Molecules 2012, 17(9), 10738-10753; https://doi.org/10.3390/molecules170910738 - 7 Sep 2012

Cited by 27 | Viewed by 6394

Abstract

Novel sandwich-type phthalocyanines containing a rare earth metal core (Pr, Nd, Eu–Lu) and macrocycles peripherally substituted by pentadecylphenoxy groups were synthesized using a cardanol-based phthalonitrile precursor and the respective lanthanide acetate. Additionally, the metal free-base analog compound was studied for comparison. The purified [...] Read more.

Novel sandwich-type phthalocyanines containing a rare earth metal core (Pr, Nd, Eu–Lu) and macrocycles peripherally substituted by pentadecylphenoxy groups were synthesized using a cardanol-based phthalonitrile precursor and the respective lanthanide acetate. Additionally, the metal free-base analog compound was studied for comparison. The purified reaction products were all found to be thick and viscous substances at room temperature, showing liquid crystalline behavior with a distinct increase in fluidity at ca. 40 °C. The complexes are readily soluble in chloroalkyl solvents and dissolve fairly well in DMF with some tendency to form aggregates. Besides they are strongly hydrophobic and reveal a peculiar affinity for lipophilic media. The compounds have been characterized by UV-Vis (absorption and emission), FTIR, MS and DSC methods. Photochemical activity in the liquid phase (dimethylformamide, dichloromethane, mineral oil) and the degree of photodegradation demonstrated under constant UV-irradiation (λ = 352 nm) have been analyzed and discussed in terms of photostability. Full article

(This article belongs to the Special Issue Tetrapyrroles, Porphyrins and Phthalocyanines)

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Open AccessArticle

Endophytic Fungi Produce Gibberellins and Indoleacetic Acid and Promotes Host-Plant Growth during Stress

by Muhammad Waqas, Abdul Latif Khan, Muhammad Kamran, Muhammad Hamayun, Sang-Mo Kang, Yoon-Ha Kim and In-Jung Lee

Molecules 2012, 17(9), 10754-10773; https://doi.org/10.3390/molecules170910754 - 7 Sep 2012

Cited by 460 | Viewed by 17401

Abstract

We isolated and examined two endophytic fungi for their potential to secrete phytohormones viz. gibberellins (GAs) and indoleacetic acid (IAA) and mitigate abiotic stresses like salinity and drought. The endophytic fungi Phoma glomerata LWL2 and Penicillium sp. LWL3 significantly promoted the shoot and [...] Read more.

We isolated and examined two endophytic fungi for their potential to secrete phytohormones viz. gibberellins (GAs) and indoleacetic acid (IAA) and mitigate abiotic stresses like salinity and drought. The endophytic fungi Phoma glomerata LWL2 and Penicillium sp. LWL3 significantly promoted the shoot and allied growth attributes of GAs-deficient dwarf mutant Waito-C and Dongjin-beyo rice. Analysis of the pure cultures of these endophytic fungi showed biologically active GAs (GA₁, GA₃, GA₄ and GA₇) in various quantities. The cultures of P. glomerata and Penicillium sp. also contained IAA. The culture application and endophytic-association with host-cucumber plants significantly increased the plant biomass and related growth parameters under sodium chloride and polyethylene glycol induced salinity and drought stress as compared to control plants. The endophytic symbiosis resulted in significantly higher assimilation of essential nutrients like potassium, calcium and magnesium as compared to control plants during salinity stress. Endophytic-association reduced the sodium toxicity and promoted the host-benefit ratio in cucumber plants as compared to non-inoculated control plants. The symbiotic-association mitigated stress by compromising the activities of reduced glutathione, catalase, peroxidase and polyphenol oxidase. Under stress conditions, the endophyte-infection significantly modulated stress through down-regulated abscisic acid, altered jasmonic acid, and elevated salicylic acid contents as compared to control. In conclusion, the two endophytes significantly reprogrammed the growth of host plants during stress conditions. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Aggregating Behavior of Phenolic Compounds — A Source of False Bioassay Results?

by Leena Pohjala and Päivi Tammela

Molecules 2012, 17(9), 10774-10790; https://doi.org/10.3390/molecules170910774 - 7 Sep 2012

Cited by 86 | Viewed by 7041

Abstract

Previous descriptions of quercetin, a widely studied flavonoid, as a frequently reported nonspecific screening hit due to aggregating behavior has raised questions about the reliability of in vitro bioactivity reports of phenolic compounds. Here a systematic study on 117 phenolic compounds is presented, [...] Read more.

Previous descriptions of quercetin, a widely studied flavonoid, as a frequently reported nonspecific screening hit due to aggregating behavior has raised questions about the reliability of in vitro bioactivity reports of phenolic compounds. Here a systematic study on 117 phenolic compounds is presented, concerning their aggregating tendency and the relevance of this phenomenon to obtaining false bioassay results. Fourteen compounds formed aggregates detectable by dynamic light scattering (DLS) when assayed at 10 µM in Tris-HCl pH 7.5. Flavonoids were more prone to aggregation than other phenolic compounds, and the aggregate formation was highly dependent on the vehicle, ionic strength and pH. The compounds were also assayed against three unrelated enzymes in the presence and absence of Triton X-100, and their bioactivity ratios were collected from PubChem database. By comparing these datasets, quercetin and rhamnetin were confirmed as promiscuous inhibitors. In general, flavonoids exhibited also higher bioactivity ratios in the PubChem database than coumarins or organic acids. To conclude, aggregate formation can be controlled with Triton X-100 and this phenomenon needs to be considered when bioassay data is interpreted, but our data indicates that it does not always lead to unspecific inhibition of biological targets. Full article

(This article belongs to the Collection Bioactive Compounds)

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Open AccessArticle

Mesua beccariana (Clusiaceae), A Source of Potential Anti-cancer Lead Compounds in Drug Discovery

by Soek Sin Teh, Gwendoline Cheng Lian Ee, Siau Hui Mah, Yang Mooi Lim and Mawardi Rahmani

Molecules 2012, 17(9), 10791-10800; https://doi.org/10.3390/molecules170910791 - 10 Sep 2012

Cited by 18 | Viewed by 5016

Abstract

An investigation on biologically active secondary metabolites from the stem bark of Mesua beccariana was carried out. A new cyclodione, mesuadione (1), along with several known constituents which are beccamarin (2), 2,5-dihydroxy-1,3,4-trimethoxy anthraquinone (3), 4-methoxy-1,3,5-trihydroxyanthraquinone (4 [...] Read more.

An investigation on biologically active secondary metabolites from the stem bark of Mesua beccariana was carried out. A new cyclodione, mesuadione (1), along with several known constituents which are beccamarin (2), 2,5-dihydroxy-1,3,4-trimethoxy anthraquinone (3), 4-methoxy-1,3,5-trihydroxyanthraquinone (4), betulinic acid (5) and stigmasterol (6) were obtained from this ongoing research. Structures of these compounds were elucidated by extensive spectroscopic methods, including 1D and 2D-NMR, GC-MS, IR and UV techniques. Preliminary tests of the in vitro cytotoxic activities of all the isolated metabolites against a panel of human cancer cell lines Raji (lymphoma), SNU-1 (gastric carcinoma), K562 (erythroleukemia cells), LS-174T (colorectal adenocarcinoma), HeLa (cervical cells), SK-MEL-28 (malignant melanoma cells), NCI-H23 (lung adenocarcinoma), IMR-32 (neuroblastoma) and Hep-G2 (hepatocellular liver carcinoma) were carried out using an MTT assay. Mesuadione (1), beccamarin (2), betulinic acid (5) and stigmasterol (6) displayed strong inhibition of Raji cell proliferation, while the proliferation rate of SK-MEL-28 and HeLa were strongly inhibited by stigmasterol (6) and beccamarin (2), indicating these secondary metabolites could be anti-cancer lead compounds in drug discovery. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Photoelectrode Characteristics of Partially Hydrolyzed Aluminum Phthalocyanine Chloride/Fullerene C₆₀ Composite Nanoparticles Working in a Water Phase

by Shuai Zhang, Toshiyuki Abe, Tomokazu Iyoda and Keiji Nagai

Molecules 2012, 17(9), 10801-10815; https://doi.org/10.3390/molecules170910801 - 10 Sep 2012

Cited by 6 | Viewed by 6235

Abstract

Photoelectrochemical measurements were used to study the photoelectrode characteristics of composite nanoparticles composed of fullerene C₆₀ and partially hydrolyzed aluminum phthalocyanine chloride (AlPc). In cyclic voltammetry measurements, the electrodes coated with the composite nanoparticles were found to have photoanodic [electron donor: 2-mercaptoethanol [...] Read more.

Photoelectrochemical measurements were used to study the photoelectrode characteristics of composite nanoparticles composed of fullerene C₆₀ and partially hydrolyzed aluminum phthalocyanine chloride (AlPc). In cyclic voltammetry measurements, the electrodes coated with the composite nanoparticles were found to have photoanodic [electron donor: 2-mercaptoethanol (ME)] and photocathodic (electron acceptor: O₂) characteristics similar to those of the vapor-deposited p/n junction electrode. Their photoanodic features were further investigated with respect to the transient photocurrent response to light irradiation and the dependence on ME concentration (under potentiostatic conditions), from which it was noted that there was a decrease in the initial spiky photocathodic current and saturation of the steady-state photoanodic current at a higher ME concentration. Thus, the reaction kinetics was probably dominated by charge transport process. Moreover, external and internal quantum efficiency spectrum measurements indicated that the composite nanoparticles responded to the full spectrum of visible light ( < 880 nm) for both the photoanodic and photocathodic current. The present research will assist comprehension of photocatalytic behavior of the composite nanoparticles. Full article

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Open AccessArticle

Phorbol Esters from Jatropha Meal Triggered Apoptosis, Activated PKC-δ, Caspase-3 Proteins and Down-Regulated the Proto-Oncogenes in MCF-7 and HeLa Cancer Cell Lines

by Ehsan Oskoueian, Norhani Abdullah and Syahida Ahmad

Molecules 2012, 17(9), 10816-10830; https://doi.org/10.3390/molecules170910816 - 10 Sep 2012

Cited by 26 | Viewed by 6834

Abstract

Jatropha meal produced from the kernel of Jatropha curcas Linn. grown in Malaysia contains phorbol esters (PEs). The potential benefits of PEs present in the meal as anticancer agent are still not well understood. Hence, this study was conducted to evaluate the cytotoxic [...] Read more.

Jatropha meal produced from the kernel of Jatropha curcas Linn. grown in Malaysia contains phorbol esters (PEs). The potential benefits of PEs present in the meal as anticancer agent are still not well understood. Hence, this study was conducted to evaluate the cytotoxic effects and mode of actions of PEs isolated from Jatropha meal against breast (MCF-7) and cervical (HeLa) cancer cell lines. Isolated PEs inhibited cells proliferation in a dose-dependent manner of both MCF-7 and HeLa cell lines with the IC₅₀ of 128.6 ± 2.51 and 133.0 ± 1.96 µg PMA equivalents/mL respectively, while the values for the phorbol 12-myristate 13-acetate (PMA) as positive control were 114.7 ± 1.73 and 119.6 ± 3.73 µg/mL, respectively. Microscopic examination showed significant morphological changes that resemble apoptosis in both cell lines when treated with PEs and PMA at IC₅₀ concentration after 24 h. Flow cytometry analysis and DNA fragmentation results confirmed the apoptosis induction of PEs and PMA in both cell lines. The PEs isolated from Jatropha meal activated the PKC-δ and down-regulated the proto-oncogenes (c-Myc, c-Fos and c-Jun). These changes probably led to the activation of Caspase-3 protein and apoptosis cell death occurred in MCF-7 and HeLa cell lines upon 24 h treatment with PEs and PMA. Phorbol esters of Jatropha meal were found to be promising as an alternative to replace the chemotherapeutic drugs for cancer therapy. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Open AccessArticle

Protective Effects of the Key Compounds Isolated from Corni fructus against β-Amyloid-Induced Neurotoxicity in PC12 Cells

by Seung-Young Hong, Woo-Sik Jeong and Mira Jun

Molecules 2012, 17(9), 10831-10845; https://doi.org/10.3390/molecules170910831 - 10 Sep 2012

Cited by 68 | Viewed by 7833

Abstract

β-Amyloid (Aβ) peptide is the major component of senile plaques and is considered to have a causal role in the development and progression of Alzheimer’s disease (AD). There is compelling evidence supporting the notion that Aβ-induced cytotoxicity is mediated though the generation of [...] Read more.

β-Amyloid (Aβ) peptide is the major component of senile plaques and is considered to have a causal role in the development and progression of Alzheimer’s disease (AD). There is compelling evidence supporting the notion that Aβ-induced cytotoxicity is mediated though the generation of ROS. In the present study, we investigated the neuroprotective effects of ursolic acid (UA), p-coumaric acid (p-CA), and gallic acid (GA) isolated from Corni fructus (CF) against Aβ(25–35)-induced toxicity in PC12 cell. Exposure of PC12 cells to 50 μM Aβ(25–35) increased cellular oxidative stress, the number of apoptotic cells and caspase-3 activity and finally caused significant cell death. However, UA, p-CA, and GA not only suppressed the generation of ROS but also attenuated DNA fragmentation and eventually attenuated Aβ-induced apoptosis in a dose-dependent manner. In protecting cells against Aβ neurotoxicity, UA and GA possessed stronger ability against ROS generation than p-CA, while p-CA showed the strongest anti-apoptotic activity. Particularly, p-CA protected cells at the concentration range from 0.5 up to 125 μM without any adverse effect. Taken together, these effects of UA, p-CA, and GA may be partly associated with the neuroprotective effect of CF. Furthermore, our findings might raise a possibility of therapeutic applications of CF for preventing and/or treating neurodegenerative diseases. Full article

(This article belongs to the Collection Bioactive Compounds)

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Open AccessArticle

Synthesis and Antibacterial Activities of Novel 4-Hydroxy-7-hydroxy- and 3-Carboxycoumarin Derivatives

by Pen-Yuan Lin, Kuang-Sheng Yeh, Chien-Ling Su, Shiow-Yunn Sheu, Tiffany Chen, Keng-Liang Ou, Mei-Hsiang Lin and Lin-Wen Lee

Molecules 2012, 17(9), 10846-10863; https://doi.org/10.3390/molecules170910846 - 10 Sep 2012

Cited by 32 | Viewed by 6379

Abstract

Coumarin derivatives are used as fluorescent dyes and medicines. They also have some notable physiological effects, including the acute hepatoxicity and carcinogenicity of certain aflatoxins, the anticoagulant action of dicoumarol, and the antibiotic activity of novobicin and coumerymycin A1. Because the number of [...] Read more.

Coumarin derivatives are used as fluorescent dyes and medicines. They also have some notable physiological effects, including the acute hepatoxicity and carcinogenicity of certain aflatoxins, the anticoagulant action of dicoumarol, and the antibiotic activity of novobicin and coumerymycin A1. Because the number of drug resistant strains is increasing at present, the synthesis of new antibacterial compounds is one of the critical methods for treating infectious diseases. Therefore, a series of coumarin-substituted derivatives, namely 4-hydroxy- and 7-hydroxycoumarins, and 3-carboxycoumarins were synthesized. 4-Hydroxycoumarin derivatives 4a–c underwent rearrangement reactions. Both 4- and 7-hydroxycoumarins were treated with activated aziridines which produced series of ring-opened products 7, 8, 10, and 11. 3-Carboxy-coumarin amide dimer derivatives 14–21 were prepared by reacting aliphatic alkylamines and alkyldiamines with PyBOP and DIEA. In this study, we use a new technique called modified micro-plate antibiotic susceptibility test method (MMAST), which is more convenient, more efficient, and more accurate than previous methods and only a small amount of the sample is required for the test. Some of the compounds were produced by reactions with acid anhydrides and demonstrated the ability to inhibit Gram-positive microorganisms. The dimer derivatives displayed lower antibacterial activities. Full article

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Open AccessArticle

Ultrasound Irradiation Promoted Enzymatic Transesterification of (R/S)-1-Chloro-3-(1-naphthyloxy)-2-propanol

by Feng Wang, Hong Zhang, Jiaxin Wang, Ge Chen, Xuedong Fang, Zhi Wang and Lei Wang

Molecules 2012, 17(9), 10864-10874; https://doi.org/10.3390/molecules170910864 - 10 Sep 2012

Cited by 10 | Viewed by 4584

Abstract

(R)-1-Chloro-3-(1-naphthyloxy)-2-propanol (3), which is the key intermediate of (S)-propranolol, was successfully prepared via enantioselective transesterification catalyzed by lipase under ultrasound irradiation. Compared with conventional shaking, the enzyme activity and enantioselectivity were dramatically increased under ultrasound exposure. Effects [...] Read more.

(R)-1-Chloro-3-(1-naphthyloxy)-2-propanol (3), which is the key intermediate of (S)-propranolol, was successfully prepared via enantioselective transesterification catalyzed by lipase under ultrasound irradiation. Compared with conventional shaking, the enzyme activity and enantioselectivity were dramatically increased under ultrasound exposure. Effects of various reaction conditions on the synthetic activity of enzyme as well as enantioselectivity, including the type of enzyme, ultrasound power, solvent, acyl donor, temperature and substrate molar ratio, were investigated. Pseudomonas sp. lipase (PSL) showed an excellent catalytic performance under optimum conditions (enzyme activity: 78.3 ± 3.2 μmol·g⁻¹·min⁻¹, E value: 98 ± 6). Full article

(This article belongs to the Section Organic Chemistry)

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Open AccessArticle

Effect of Different Purification Techniques on the Characteristics of Heteropolysaccharide-Protein Biopolymer from Durian (Durio zibethinus) Seed

by Bahareh Tabatabaee Amid and Hamed Mirhosseini

Molecules 2012, 17(9), 10875-10892; https://doi.org/10.3390/molecules170910875 - 10 Sep 2012

Cited by 56 | Viewed by 6294

Abstract

Natural biopolymers from plant sources contain many impurities (e.g., fat, protein, fiber, natural pigment and endogenous enzymes), therefore, an efficient purification process is recommended to minimize these impurities and consequently improve the functional properties of the biopolymer. The main objective of the present [...] Read more.

Natural biopolymers from plant sources contain many impurities (e.g., fat, protein, fiber, natural pigment and endogenous enzymes), therefore, an efficient purification process is recommended to minimize these impurities and consequently improve the functional properties of the biopolymer. The main objective of the present study was to investigate the effect of different purification techniques on the yield, protein content, solubility, water- and oil-holding capacity of a heteropolysaccharide-protein biopolymer obtained from durian seed. Four different purification methods using different chemicals and solvents (i.e., A (isopropanol and ethanol), B (isopropanol and acetone), C (saturated barium hydroxide), and D (Fehling solution)] to liberate the purified biopolymer from its crude form were compared. In most cases, the purification process significantly (p < 0.05) improved the physicochemical properties of heteropolysaccharide-protein biopolymer from durian fruit seed. The present work showed that the precipitation using isopropanol and acetone (Method B) resulted in the highest purification yield among all the tested purification techniques. The precipitation using saturated barium hydroxide (Method C) led to induce the highest solubility and relatively high capacity of water absorption. The current study reveals that the precipitation using Fehling solution (Method D) most efficiently eliminates the protein fraction, thus providing more pure biopolymer suitable for biological applications. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Platelet-Activating Factor (PAF) Antagonistic Activity of a New Biflavonoid from Garcinia nervosa var. pubescens King

by Juriyati Jalil, Ibrahim Jantan, Azura Abdul Ghani and Shahnaz Murad

Molecules 2012, 17(9), 10893-10901; https://doi.org/10.3390/molecules170910893 - 10 Sep 2012

Cited by 13 | Viewed by 4584

Abstract

The methanol extract of the leaves of Garcinia nervosa var. pubescens King, which showed strong inhibitory effects on platelet-activating factor (PAF) receptor binding, was subjected to bioassay-guided isolation to obtain a new biflavonoid, II-3,I-5, II-5,II-7,I-4',II-4'-hexahydroxy-(I-3,II-8)-flavonylflavanonol together with two known flavonoids, 6-methyl-4'-methoxyflavone and acacetin. [...] Read more.

The methanol extract of the leaves of Garcinia nervosa var. pubescens King, which showed strong inhibitory effects on platelet-activating factor (PAF) receptor binding, was subjected to bioassay-guided isolation to obtain a new biflavonoid, II-3,I-5, II-5,II-7,I-4',II-4'-hexahydroxy-(I-3,II-8)-flavonylflavanonol together with two known flavonoids, 6-methyl-4'-methoxyflavone and acacetin. The structures of the compounds were elucidated by spectroscopic methods. The compounds were evaluated for their ability to inhibit PAF receptor binding to rabbit platelets using ³H-PAF as a ligand. The biflavonoid and acacetin showed strong inhibition with IC₅₀ values of 28.0 and 20.4 µM, respectively. The results suggest that these compounds could be responsible for the strong PAF antagonistic activity of the plant. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Synthesis of a New Series of Pyridine and Fused Pyridine Derivatives

by Siham AbdulRahman Al-Issa

Molecules 2012, 17(9), 10902-10915; https://doi.org/10.3390/molecules170910902 - 11 Sep 2012

Cited by 41 | Viewed by 9360

Abstract

The reaction of 4-methyl-2-phenyl-1,2-dihydro-6-oxo-5-pyridine- carbonitrile (1) with arylidene malononitrile afforded isoquinoline derivatives 2a,b. 6-Chloro-4-methyl-2-phenyl-5-pyridinecarbonitile (3) obtained by chlorination of compound 1 with phosphoryl chloride was converted into 6-amino-4-methyl-2-phenyl-5-pyridinecarbonitrile (4) and 6-hydrazido-4-methyl-2-phenyl-5-pyridinecarbonitrile (5) [...] Read more.

The reaction of 4-methyl-2-phenyl-1,2-dihydro-6-oxo-5-pyridine- carbonitrile (1) with arylidene malononitrile afforded isoquinoline derivatives 2a,b. 6-Chloro-4-methyl-2-phenyl-5-pyridinecarbonitile (3) obtained by chlorination of compound 1 with phosphoryl chloride was converted into 6-amino-4-methyl-2-phenyl-5-pyridinecarbonitrile (4) and 6-hydrazido-4-methyl-2-phenyl-5-pyridinecarbonitrile (5) in good yield, through reactions with ammonium acetate and hydrazine hydrate, respectively. Treatment of 4 with ethyl acetoacetate, acetic anhydride, formic acid, urea and thiourea gave the corresponding pyrido [2,3-d] pyrimidine derivatives 7–10a,b. A new series of 6-substituted-4-methyl-2-phenyl-5-pyridine carbonitriles 11–13 has been synthesized via reaction of 4 with phenyl isothiocyanate, benzenesulphonyl chloride and acetic anhydride. Treatment of 4 with malononitrile gave 1,8-naphthyridine derivative 14. The reactivity of hydrazide 5 towards acetic acid, phenylisothiocyanate and methylacrylate to give pyrazolo-[3,4-b]-pyridine derivatives 15–17 was studied. Treatment of 5 with acetic anhydride, phthalic anhydride and carbon disulphide gave pyridine derivatives 18,19 and 1,2,4-triazolo-[3,4-a]-pyridine derivative 20. Full article

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Open AccessArticle

Antiproliferation and Induction of Apoptosis in Ca9-22 Oral Cancer Cells by Ethanolic Extract of Gracilaria tenuistipitata

by Chi-Chen Yeh, Chao-Neng Tseng, Jing-Iong Yang, Hurng-Wern Huang, Yi Fang, Jen-Yang Tang, Fang-Rong Chang and Hsueh-Wei Chang

Molecules 2012, 17(9), 10916-10927; https://doi.org/10.3390/molecules170910916 - 11 Sep 2012

Cited by 90 | Viewed by 8634

Abstract

The water extract of Gracilaria tenuistipitata have been found to be protective against oxidative stress-induced cellular DNA damage, but the biological function of the ethanolic extracts of G. tenuistipitata (EEGT) is still unknown. In this study, the effect of EEGT on oral squamous [...] Read more.

The water extract of Gracilaria tenuistipitata have been found to be protective against oxidative stress-induced cellular DNA damage, but the biological function of the ethanolic extracts of G. tenuistipitata (EEGT) is still unknown. In this study, the effect of EEGT on oral squamous cell cancer (OSCC) Ca9-22 cell line was examined in terms of the cell proliferation and oxidative stress responses. The cell viability of EEGT-treated OSCC cells was significantly reduced in a dose-response manner (p < 0.0001). The annexin V intensity and pan-caspase activity of EEGT-treated OSCC cells were significantly increased in a dose-response manner (p < 0.05 to 0.0001). EEGT significantly increased the reactive oxygen species (ROS) level (p < 0.0001) and decreased the glutathione (GSH) level (p < 0.01) in a dose-response manner. The mitochondrial membrane potential (MMP) of EEGT-treated OSCC cells was significantly decreased in a dose-response manner (p < 0.005). In conclusion, we have demonstrated that EEGT induced the growth inhibition and apoptosis of OSCC cells, which was accompanied by ROS increase, GSH depletion, caspase activation, and mitochondrial depolarization. Therefore, EEGT may have potent antitumor effect against oral cancer cells. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Systematic Study of the Physicochemical Properties of a Homologous Series of Aminobisphosphonates

by Aino-Liisa Alanne, Helena Hyvönen, Manu Lahtinen, Markku Ylisirniö, Petri Turhanen, Erkki Kolehmainen, Sirpa Peräniemi and Jouko Vepsäläinen

Molecules 2012, 17(9), 10928-10945; https://doi.org/10.3390/molecules170910928 - 12 Sep 2012

Cited by 36 | Viewed by 6167

Abstract

Aminobisphosphonates, e.g., alendronate and neridronate, are a well known class of molecules used as drugs for various bone diseases. Although these molecules have been available for decades, a detailed understanding of their most important physicochemical properties under comparable conditions is lacking. In this [...] Read more.

Aminobisphosphonates, e.g., alendronate and neridronate, are a well known class of molecules used as drugs for various bone diseases. Although these molecules have been available for decades, a detailed understanding of their most important physicochemical properties under comparable conditions is lacking. In this study, ten aminobisphosphonates, H₂N(CH₂)_nC(OH)[P(O)(OH)₂]₂, in which n = 2–5, 7–11 and 15 have been synthesized. Their aqueous solubility as a function of temperature and pH, pK_a-values, thermal stability, IR absorptions, and NMR spectral data for bothliquid (¹H, ¹³C, ³¹P-NMR) and solid state (¹³C, ¹⁵N and ³¹P-CPMAS NMR) were determined. Full article

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A Comparative Study of the Characteristics of Cross-Linked, Oxidized and Dual-Modified Rice Starches

by Hua-Xi Xiao, Qin-Lu Lin, Gao-Qiang Liu and Feng-Xiang Yu

Molecules 2012, 17(9), 10946-10957; https://doi.org/10.3390/molecules170910946 - 12 Sep 2012

Cited by 83 | Viewed by 6625

Abstract

Rice starch was cross-linked with epichlorohydrin (0.3%, w/w, on a dry starch basis) and oxidized with sodium hypochlorite (2.5% w/w), respectively. Two dual-modified rice starch samples (oxidized cross-linked rice starch and cross-linked oxidized rice starch) were obtained by the oxidation of cross-linked rice [...] Read more.

Rice starch was cross-linked with epichlorohydrin (0.3%, w/w, on a dry starch basis) and oxidized with sodium hypochlorite (2.5% w/w), respectively. Two dual-modified rice starch samples (oxidized cross-linked rice starch and cross-linked oxidized rice starch) were obtained by the oxidation of cross-linked rice starch and the cross-linking of oxidized rice starch at the same level of reagents. The physicochemical properties of native rice starch, cross-linked rice starch and oxidized rice starch were also studied parallel with those of the two dual-modified rice starch samples using rapid visco analysis (RVA), differential scanning calorimetry (DSC), dynamic rheometry and scanning electron microscopy (SEM). It was found that the levels of cross-linking and oxidation used in this study did not cause any significant changes in the morphology of rice starch granules. Cross-linked oxidized starch showed lower swelling power (SP) and solubility, and higher paste clarity in comparison with native starch. Cross-linked oxidized rice starch also had the lowest tendency of retrogradation and highest ability to resistant to shear compared with native, cross-linked, oxidized and oxidized cross-linked rice starches. These results suggest that the undesirable properties in native, cross-linked and oxidized rice starch samples could be overcome through dual-modification. Full article

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Open AccessArticle

Applied Biological and Physicochemical Activity of Isoquinoline Alkaloids: Oxoisoaporphine and Boldine

by Eduardo Sobarzo-Sánchez, Patricio González Soto, Cristóbal Valdés Rivera, Georgina Sánchez and María Eliana Hidalgo

Molecules 2012, 17(9), 10958-10970; https://doi.org/10.3390/molecules170910958 - 12 Sep 2012

Cited by 17 | Viewed by 6352

Abstract

The aim of this study was to determine the electronic influence of substituent groups and annelated rings such as oxazole-oxazinone on the physicochemical and photoprotection, antioxidant capacity, toxicity and singlet oxygen photosensitization biological properties of isoquinoline alkaloid frameworks. Thus, oxoisoaporphine derivatives 1– [...] Read more.

The aim of this study was to determine the electronic influence of substituent groups and annelated rings such as oxazole-oxazinone on the physicochemical and photoprotection, antioxidant capacity, toxicity and singlet oxygen photosensitization biological properties of isoquinoline alkaloid frameworks. Thus, oxoisoaporphine derivatives 1–5 and 3-azaoxoisoaporphine (6), some of them with phenolic structures, did not present any antioxidant capacity, possibly either by formation of keto-enol tautomerism species or the formation of unstable free radicals. Due to the singlet oxygen quantum yields (F_D) near to unity, and greater photostability than phenalenone, oxoisoaporphines 4–6 may be considered as photosensitizers for singlet oxygen production and can be used as new universal study tools. The biological application as antibacterial agents is an important and possible tool in the study of compounds with low cytotoxicity and high reactivity in antineoplastic chemotherapy. On the other hand, when boldine and its annelated derivatives B1–4 are irradiated, a photoprotector effect is observed (SPF = 2.35), even after 30 minutes of irradiation. They also act as photoprotectors in cell fibroblast cultures. No hemolysis was detected for boldine hydrochloride and its salts without irradiation. In solutions irradiated before incubation (at concentrations over 200 ppm) photoproducts were toxic to the nauplii of Artemia salina. Full article

(This article belongs to the Special Issue Aporphines and Oxoaporphines)

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A Structural Study of Epoxidized Natural Rubber (ENR-50) and Its Cyclic Dithiocarbonate Derivative Using NMR Spectroscopy Techniques

by Rosniza Hamzah, Mohamad Abu Bakar, Melati Khairuddean, Issam Ahmed Mohammed and Rohana Adnan

Molecules 2012, 17(9), 10974-10993; https://doi.org/10.3390/molecules170910974 - 12 Sep 2012

Cited by 50 | Viewed by 10196

Abstract

A structural study of epoxidized natural rubber (ENR-50) and its cyclic dithiocarbonate derivative was carried out using NMR spectroscopy techniques. The overlapping ¹H-NMR signals of ENR-50 at δ 1.56, 1.68–1.70, 2.06, 2.15–2.17 ppm were successfully assigned. In this work, the ¹³C-NMR [...] Read more.

A structural study of epoxidized natural rubber (ENR-50) and its cyclic dithiocarbonate derivative was carried out using NMR spectroscopy techniques. The overlapping ¹H-NMR signals of ENR-50 at δ 1.56, 1.68–1.70, 2.06, 2.15–2.17 ppm were successfully assigned. In this work, the ¹³C-NMR chemical shift assignments of ENR-50 were consistent to the previously reported work. A cyclic dithiocarbonate derivative of ENR-50 was synthesized from the reaction of purified ENR-50 with carbon disulfide (CS₂), in the presence of 4-dimethylaminopyridine (DMAP) as catalyst at reflux temperature. The cyclic dithiocarbonate formation involved the epoxide ring opening of the ENR-50. This was followed by insertion of the C–S moiety of CS₂ at the oxygen attached to the quaternary carbon and methine carbon of epoxidized isoprene unit, respectively. The bands due to the C=S and C–O were clearly observed in the FTIR spectrum while the ¹H-NMR spectrum of the derivative revealed the peak attributed to the methylene protons had split. The ¹³C-NMR spectrum of the derivative further indicates two new carbon peaks arising from the >C=S and quaternary carbon of cyclic dithiocarbonate. All other ¹H- and ¹³C-NMR chemical shifts of the derivative remain unchanged with respect to the ENR-50. Full article

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Inhibition of Cytochrome P450 3A in Rat Liver by the Diorganotin (IV) Compound di-n-Butyl-di-(4-chlorobenzo-hydroxamato)tin (IV) and Its Probable Mechanism

by Yunxia Zhang, Yunlan Li and Qingshan Li

Molecules 2012, 17(9), 10994-11009; https://doi.org/10.3390/molecules170910994 - 12 Sep 2012

Cited by 12 | Viewed by 4572

Abstract

The specific aims of this study were to evaluate the inhibition effect on CYP3A of di-n-butyl-di-(4-chlorobenzohydroxamato)tin (IV) (DBDCT), a tin-based complex with high antitumor activity, and the probable mechanism(s) of this action. Adult male SD rats were treated separately with natural [...] Read more.

The specific aims of this study were to evaluate the inhibition effect on CYP3A of di-n-butyl-di-(4-chlorobenzohydroxamato)tin (IV) (DBDCT), a tin-based complex with high antitumor activity, and the probable mechanism(s) of this action. Adult male SD rats were treated separately with natural saline (NS), lipopolysaccharide (LPS, 5 mg/kg), DBDCT (1.25, 2.5 and 5.0 mg/kg) intraperitoneally for 2 days after induction of CYP3A with dexamethasone (DEX, 100 mg/kg) for 4 days. Western blot analysis and fluorescent quantitation PCR (FQ-PCR) were conducted to determine the changes in expression of CYP3A, PXR, CAR and RXR. The biological accumulation of DBDCT and total Sn were determined by high-performance liquid chromatography (HPLC) and atomic fluorescence spectrometry (AFS). CYP450 content and CYP3A activities were significantly inhibited (p < 0.05) in DBDCT-treated rats compared with the control group, as was the expression of CYP3A (p < 0.05) at both protein and mRNA levels. In DBDCT-treated groups, the expression of PXR protein and mRNA increased, while the expression of CAR decreased. The biological accumulation of DBDCT and Sn in rat livers treated with DBDCT was high. The accumulation of DBDCT and Sn due to the inhibition of CYP3A may be involved in the mechanism of toxicity of DBDCT in rat liver. Full article

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Open AccessArticle

Novel Coumarin Derivatives Containing 1,2,4-Triazole, 4,5-Dicyanoimidazole and Purine Moieties: Synthesis and Evaluation of Their Cytostatic Activity

by Krešimir Benci, Leo Mandić, Tomislav Suhina, Mirela Sedić, Marko Klobučar, Sandra Kraljević Pavelić, Krešimir Pavelić, Karlo Wittine and Mladen Mintas

Molecules 2012, 17(9), 11010-11025; https://doi.org/10.3390/molecules170911010 - 12 Sep 2012

Cited by 48 | Viewed by 6822

Abstract

We report here on the synthesis and in vitro anti-tumor effects of a series of novel 1,2,4-triazole (compounds 3–6), 4,5-dicyanoimidazole (compound 7), and purine (compounds 8–13) coumarin derivatives and their acyclic nucleoside analogues 14–18 [...] Read more.

We report here on the synthesis and in vitro anti-tumor effects of a series of novel 1,2,4-triazole (compounds 3–6), 4,5-dicyanoimidazole (compound 7), and purine (compounds 8–13) coumarin derivatives and their acyclic nucleoside analogues 14–18. Structures of novel compounds 3–18 were deduced from their ¹H- and ¹³C-NMR and corresponding mass spectra. Results of anti-proliferative assays performed on a panel of selected human tumor cell lines revealed that compound 6 had moderate cytostatic activity against the HeLa cell line (IC₅₀ = 35 µM), whereas compound 10 showed moderate activity against the HeLa (IC₅₀ = 33 µM), HepG2 (IC₅₀ = 25 µM) and SW620 (IC₅₀ = 35 µM) cell lines. These compounds showed no cytotoxic effects on normal (diploid) human fibroblasts. Full article

(This article belongs to the Section Medicinal Chemistry)

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Synthesis and Chromatography-Free Purification of PNA-PEO Conjugates for the Functionalisation of Gold Sensors

by Monica Dettin, Davide Silvestri, Roberta Danesin, Erica Cretaio, Gianluca Picariello, Elisabetta Casarin, Agnese Sonato, Filippo Romanato and Margherita Morpurgo

Molecules 2012, 17(9), 11026-11045; https://doi.org/10.3390/molecules170911026 - 13 Sep 2012

Cited by 10 | Viewed by 6569

Abstract

Peptide Nucleic Acids (PNAs) linked to high molecular weight (MW) poly(ethylene oxide) (PEO) derivatives could be useful conjugates for the direct functionalisation of gold surfaces dedicated to Surface Plasmon Resonance (SPR)-based DNA sensing. However their use is hampered by the difficulty to obtain [...] Read more.

Peptide Nucleic Acids (PNAs) linked to high molecular weight (MW) poly(ethylene oxide) (PEO) derivatives could be useful conjugates for the direct functionalisation of gold surfaces dedicated to Surface Plasmon Resonance (SPR)-based DNA sensing. However their use is hampered by the difficulty to obtain them through a convenient and economical route. In this work we compared three synthetic strategies to obtain PNA-high MW PEO conjugates composed of (a) a 15-mer PNA sequence as the probe complementary to genomic DNA of Mycobacterium tuberculosis, (b) a PEO moiety (2 or 5 KDa MW) and (c) a terminal trityl-protected thiol necessary (after acidic deprotection) for grafting to gold surfaces. The 15-mer PNA was obtained by solid-phase synthesis. Its amino terminal group was later condensed to bi-functional PEO derivatives (2 and 5 KDa MW) carrying a Trt-cysteine at one end and a carboxyl group at the other end. The reaction was carried out either in solution, using HATU or PyOxim as coupling agents, or through the solid-phase approach, with 49.6%, 100% and 5.2% yield, respectively. A differential solvent extraction strategy for product purification without the need for chromatography is described. The ability of the 5 KDa PEO conjugate to function as a probe for complementary DNA detection was demonstrated using a Grating-Coupling Surface Plasmon Resonance (GC-SPR) system. The optimized PEO conjugation and purification protocols are economical and simple enough to be reproduced also within laboratories that are not highly equipped for chemical synthesis. Full article

(This article belongs to the Special Issue Nucleic Acid Analogs)

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Open AccessArticle

Synthesis of Highly Substituted Oxazoles through Iodine(III)-Mediated Reactions of Ketones with Nitriles

by Akio Saito, Nao Hyodo and Yuji Hanzawa

Molecules 2012, 17(9), 11046-11055; https://doi.org/10.3390/molecules170911046 - 13 Sep 2012

Cited by 30 | Viewed by 7622

Abstract

In the presence of trifluoromethanesulfonic acid (TfOH) or bis(trifluoromethane-sulfonyl)imide (Tf₂NH), iodosobenzene (PhI=O) efficiently promoted the reactions of dicarbonyl compounds as well as monocarbonyl compounds with nitriles to give 2,4-disubstituted and 2,4,5-trisubstituted oxazole in a single step under the mild conditions. Full article

(This article belongs to the Special Issue Organic Iodine Chemistry 2012)

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Open AccessArticle

Chemical Composition and Biological Activities of the Essential Oils from Duguetia lanceolata St. Hil. Barks

by Orlando V. Sousa, Glauciemar Del-Vechio-Vieira, Maria S. Alves, Aílson A. L. Araújo, Míriam A. O. Pinto, Maria P. H. Amaral, Mírian P. Rodarte and Maria A. C. Kaplan

Molecules 2012, 17(9), 11056-11066; https://doi.org/10.3390/molecules170911056 - 13 Sep 2012

Cited by 29 | Viewed by 5630

Abstract

Essential oils of Duguetia lanceolata barks, obtained at 2 (T2) and 4 h (T4), were identified by gas chromatography and gas chromatography/mass spectrometry. β-Elemene (12.7 and 14.9%), caryophyllene oxide (12.4 and 10.7%) and β-selinene (8.4 and 10.4%) were the most abundant components in [...] Read more.

Essential oils of Duguetia lanceolata barks, obtained at 2 (T2) and 4 h (T4), were identified by gas chromatography and gas chromatography/mass spectrometry. β-Elemene (12.7 and 14.9%), caryophyllene oxide (12.4 and 10.7%) and β-selinene (8.4 and 10.4%) were the most abundant components in T2 and T4, respectively. The essential oils inhibited the growth of Staphylococcus aureus, Streptococcus pyogenes, Escherichia coli and Candida albicans. The essential oils were cytotoxic against brine shrimp. The extraction time influenced the chemical composition and biological activities of essential oils obtained from the barks of D. lanceolata. Full article

(This article belongs to the Section Natural Products Chemistry)

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Primary Investigation of the Preparation of Nanoparticles by Precipitation

by Eliska Vaculikova, Veronika Grunwaldova, Vladimir Kral, Jiri Dohnal and Josef Jampilek

Molecules 2012, 17(9), 11067-11078; https://doi.org/10.3390/molecules170911067 - 13 Sep 2012

Cited by 19 | Viewed by 4808

Abstract

The absorption, distribution, biotransformation and excretion of a drug involve its transport across cell membranes. This process is essential and influenced by the characteristics of the drug, especially its molecular size and shape, solubility at the site of its absorption, relative lipid solubility, [...] Read more.

The absorption, distribution, biotransformation and excretion of a drug involve its transport across cell membranes. This process is essential and influenced by the characteristics of the drug, especially its molecular size and shape, solubility at the site of its absorption, relative lipid solubility, etc. One of the progressive ways for increasing bioavaibility is a nanoparticle preparation technique. Cholesterol, cholestenolone and pregnenolone acetate as model active pharmaceutical ingredients and some of the commonly used excipients as nanoparticle stabilizers were used in the investigated precipitation method that was modified and simplified and can be used as an effective and an affordable technique for the preparation of nanoparticles. All 120 prepared samples were analyzed by means of dynamic light scattering (Nanophox). The range of the particle size of the determined 100 nanoparticle samples was from 1 nm to 773 nm, whereas 82 samples contained nanoparticles of less than 200 nm. Relationships between solvents and used excipients and their amount are discussed. Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessArticle

Cyclizations Producing Hydrindanones with Two Methyl Groups at the Juncture Positions Mediated by Samarium Diiodide and Electrolysis

by Masakazu Sono, Natsuko Ise, Tsutomu Shoji and Motoo Tori

Molecules 2012, 17(9), 11079-11088; https://doi.org/10.3390/molecules170911079 - 13 Sep 2012

Cited by 5 | Viewed by 5421

Abstract

One-electron reductive intramolecular cyclization of enones with ketones or aldehydes mediated by samarium diiodide and electrolysis to afford cis-trimethyl- hydrindanolones. The reactions gave selectivities ranging from 1:1 to 100:0 depending on the conditions. Full article

(This article belongs to the Special Issue Challenges in Synthetic Chemistry)

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Open AccessArticle

Enhancement of Gene Silencing Effect and Membrane Permeability by Peptide-Conjugated 27-Nucleotide Small Interfering RNA

by Takanori Kubo, Kazuyoshi Yanagihara, Yuichiro Sato, Yasuhiro Morita and Toshio Seyama

Molecules 2012, 17(9), 11089-11102; https://doi.org/10.3390/molecules170911089 - 14 Sep 2012

Cited by 6 | Viewed by 5996

Abstract

Two different sizes of siRNAs, of which one type was 21-nucleotide (nt) siRNA containing 2-nt dangling ends and the other type was 27-nt siRNA with blunt ends, were conjugated with a nuclear export signal peptide of HIV-1 Rev at the 5′-sense end. Processing [...] Read more.

Two different sizes of siRNAs, of which one type was 21-nucleotide (nt) siRNA containing 2-nt dangling ends and the other type was 27-nt siRNA with blunt ends, were conjugated with a nuclear export signal peptide of HIV-1 Rev at the 5′-sense end. Processing by Dicer enzyme, cell membrane permeability, and RNAi efficiency of the peptide-conjugated siRNAs were examined. Dicer cleaved the peptide-conjugated 27-nt siRNA leading to the release of 21-nt siRNA, whereas the peptide-conjugated 21-nt siRNA was not cleaved. High membrane permeability and cytoplasmic localization was found in the conjugates. Moreover, the peptide-conjugated 27-nt siRNA showed increased potency of RNAi in comparison with the nonmodified 21-nt and 27-nt siRNAs, whereas the peptide-conjugated 21-nt siRNA showed decreased RNAi efficacy. This potent RNAi efficacy is probably owing to acceleration of RISC through recognition by Dicer, as well as to the improvement of cell membrane permeability and intracellular accumulation. Full article

(This article belongs to the Special Issue Nucleic Acid Analogs)

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Open AccessCommunication

A 3-D Metal-Organic Framework Constructed with Manganese(ΙΙ), 4,4'-Oxybis(benzoic acid) and 2,2'-Biphenyl: Synthesis, Crystal Structure and Photoelectric Property Characterization

by Kai-Sheng Diao, Long Li, Yu-Qiu Ding and Fu-Hou Lei

Molecules 2012, 17(9), 11103-11112; https://doi.org/10.3390/molecules170911103 - 14 Sep 2012

Cited by 1 | Viewed by 5122

Abstract

Assembly of 4,4'-oxybis(benzoic acid) (H₂L) with manganese chloride in the presence of 2,2'-biphenyl (2,2'-bpy) affords a new coordination polymer [Mn₃L₃(2,2'-bpy)₂]_n (1), in which the [MnL₂]_n layers are extended by [...] Read more.

Assembly of 4,4'-oxybis(benzoic acid) (H₂L) with manganese chloride in the presence of 2,2'-biphenyl (2,2'-bpy) affords a new coordination polymer [Mn₃L₃(2,2'-bpy)₂]_n (1), in which the [MnL₂]_n layers are extended by L bridges resulting in a three-dimensional (3-D) coordination framework. The network structure of 1 has unusual (2,6)-connectivity and represents a new type of (8¹²·12³)(8)(3) topology. These identical and complementary networks are entangled to generate a self-penetrating supramolecular lattice. Moreover, the fluorescence spectrum of 1 exhibits fluorescent emission in the solution of methanol at room temperature. Electrochemical investigation illustrates the electrochemical properties of the title compound. The structure (C₆₂H₄₀Mn₃N₄O₁₅)_n is monoclinic with a = 14.2304(18), b = 17.019(2), c = 25.805(3) Å, α = γ = 90, β = 92.932(2)° and space group C2/c. Full article

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Open AccessArticle

Biological Activity and Safety of Tripterygium Extract Prepared by Sodium Carbonate Extraction

by Wei Fang, Fan Peng, Tao Yi, Cong Zhang, Chunxi Wan, Huibi Xu, Christopher Waikei Lam and Xiangliang Yang

Molecules 2012, 17(9), 11113-11123; https://doi.org/10.3390/molecules170911113 - 17 Sep 2012

Cited by 12 | Viewed by 6505

Abstract

The commercial preparation named “Tripterygium glycosides” prepared by column chromatography has been used for the treatment of inflammatory and autoimmune diseases with significant efficacy but concurrent toxicity. The aim of this study was to reduce the toxicity of Tripterygium extracts, using cytotoxicity [...] Read more.

The commercial preparation named “Tripterygium glycosides” prepared by column chromatography has been used for the treatment of inflammatory and autoimmune diseases with significant efficacy but concurrent toxicity. The aim of this study was to reduce the toxicity of Tripterygium extracts, using cytotoxicity and anti-inflammatory activity of the three principal active components of Tripterygium wilfordii Hook. F. (TWHF) as guiding parameters. Column chromatography was replaced by sodium carbonate extraction for removing the acidic compounds and enriching epoxyditerpenoids and alkaloids in the extract. Results showed that the therapeutic index (IC₅₀/EC₅₀) on murine macrophage Raw 264.7 cells and rat mesangial HBZY-1 cells of the extract prepared by sodium carbonate extraction was significantly higher than that of Tripterygium glycosides (0.8 and 5.2 vs. 0.3 and 2.6, p < 0.05), while its cytotoxicity on human liver HL7702 cells was significantly lower (14.5 ± 1.4 vs. 6.8 ± 0.9, p < 0.05). Further acute oral toxicity experiments showed that the LD₅₀ value of this extract was 1,210 mg/kg compared to 257 mg/kg for Tripterygium glycosides. All the above results suggest that Tripterygium extract prepared by sodium carbonate extraction may represent a potentially optimal source of medicine with good therapeutic index. Full article

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Open AccessArticle

Effects of Sorghum [Sorghum bicolor (L.) Moench] Crude Extracts on Starch Digestibility, Estimated Glycemic Index (EGI), and Resistant Starch (RS) Contents of Porridges

by Dilek Lemlioglu-Austin, Nancy D. Turner, Cassandra M. McDonough and Lloyd W. Rooney

Molecules 2012, 17(9), 11124-11138; https://doi.org/10.3390/molecules170911124 - 17 Sep 2012

Cited by 75 | Viewed by 9683

Abstract

Bran extracts (70% aqueous acetone) of specialty sorghum varieties (tannin, black, and black with tannin) were used to investigate the effects of sorghum phenolic compounds on starch digestibility, Estimated Glycemic Index (EGI), and Resistant Starch (RS) of porridges made with normal corn starch, [...] Read more.

Bran extracts (70% aqueous acetone) of specialty sorghum varieties (tannin, black, and black with tannin) were used to investigate the effects of sorghum phenolic compounds on starch digestibility, Estimated Glycemic Index (EGI), and Resistant Starch (RS) of porridges made with normal corn starch, enzyme resistant high amylose corn starch, and ground whole sorghum flours. Porridges were cooked with bran extracts in a Rapid Visco-analyser (RVA). The cooking trials indicated that bran extracts of phenolic-rich sorghum varieties significantly reduced EGI, and increased RS contents of porridges. Thus, there could be potential health benefits associated with the incorporation of phenolic-rich sorghum bran extracts into foods to slow starch digestion and increase RS content. Full article

(This article belongs to the Collection Bioactive Compounds)

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Open AccessArticle

Proximate Composition, Nutritional Attributes and Mineral Composition of Peperomia pellucida L. (Ketumpangan Air) Grown in Malaysia

by Der-Jiun Ooi, Shahid Iqbal and Maznah Ismail

Molecules 2012, 17(9), 11139-11145; https://doi.org/10.3390/molecules170911139 - 17 Sep 2012

Cited by 88 | Viewed by 13807

Abstract

This study presents the proximate and mineral composition of Peperomia pellucida L., an underexploited weed plant in Malaysia. Proximate analysis was performed using standard AOAC methods and mineral contents were determined using atomic absorption spectrometry. The results indicated Peperomia pellucida to be rich [...] Read more.

This study presents the proximate and mineral composition of Peperomia pellucida L., an underexploited weed plant in Malaysia. Proximate analysis was performed using standard AOAC methods and mineral contents were determined using atomic absorption spectrometry. The results indicated Peperomia pellucida to be rich in crude protein, carbohydrate and total ash contents. The high amount of total ash (31.22%) suggests a high-value mineral composition comprising potassium, calcium and iron as the main elements. The present study inferred that Peperomia pellucida would serve as a good source of protein and energy as well as micronutrients in the form of a leafy vegetable for human consumption. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Antitrypanosomal Alkaloids from the Marine Bacterium Bacillus pumilus

by Sergio Martínez-Luis, José Félix Gómez, Carmenza Spadafora, Héctor M. Guzmán and Marcelino Gutiérrez

Molecules 2012, 17(9), 11146-11155; https://doi.org/10.3390/molecules170911146 - 18 Sep 2012

Cited by 54 | Viewed by 7059

Abstract

Fractionation of the ethyl acetate extract of the marine bacterium Bacillus pumilus isolated from the black coral Antipathes sp. led to the isolation of five compounds: cyclo-(L-Leu-L-Pro) (1), 3-hydroxyacetylindole (2), N-acetyl-b-oxotryptamine (3 [...] Read more.

Fractionation of the ethyl acetate extract of the marine bacterium Bacillus pumilus isolated from the black coral Antipathes sp. led to the isolation of five compounds: cyclo-(L-Leu-L-Pro) (1), 3-hydroxyacetylindole (2), N-acetyl-b-oxotryptamine (3), cyclo-(L-Phe-L-Pro) (4), and 3-formylindole (5). The structures of compounds 1−5 were established by spectroscopic analyses, including HRESITOF-MS and NMR (¹H, ¹³C, HSQC, HMBC and COSY). Compounds 2, 3 and 5 caused the inhibition on the growth of Trypanosoma cruzi (T. cruzi), with IC₅₀ values of 20.6, 19.4 and 26.9 μM, respectively, with moderate cytotoxicity against Vero cells. Compounds 1−5 were found to be inactive when tested against Plasmodium falciparum and Leishmania donovani, therefore showing selectivity against T. cruzi parasites. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Antioxidant Profile of Trifolium pratense L.

by Biljana Kaurinovic, Mira Popovic, Sanja Vlaisavljevic, Heidy Schwartsova and Mirjana Vojinovic-Miloradov

Molecules 2012, 17(9), 11156-11172; https://doi.org/10.3390/molecules170911156 - 18 Sep 2012

Cited by 43 | Viewed by 7687

Abstract

In order to examine the antioxidant properties of five different extracts of Trifolium pratense L. (Leguminosae) leaves, various assays which measure free radical scavenging ability were carried out: 1,1-diphenyl-2-picrylhydrazyl, hydroxyl, superoxide anion and nitric oxide radical scavenger capacity tests and lipid peroxidation assay. [...] Read more.

In order to examine the antioxidant properties of five different extracts of Trifolium pratense L. (Leguminosae) leaves, various assays which measure free radical scavenging ability were carried out: 1,1-diphenyl-2-picrylhydrazyl, hydroxyl, superoxide anion and nitric oxide radical scavenger capacity tests and lipid peroxidation assay. In all of the tests, only the H₂O and (to some extent) the EtOAc extracts showed a potent antioxidant effect compared with BHT and BHA, well-known synthetic antioxidants. In addition, in vivo experiments were conducted with antioxidant systems (activities of GSHPx, GSHR, Px, CAT, XOD, GSH content and intensity of LPx) in liver homogenate and blood of mice after their treatment with extracts of T. pratense leaves, or in combination with CCl₄. Besides, in the extracts examined the total phenolic and flavonoid amounts were also determined, together with presence of the selected flavonoids: quercetin, luteolin, apigenin, naringenin and kaempferol, which were studied using a HPLC-DAD technique. HPLC-DAD analysis showed a noticeable content of natural products according to which the examined Trifolium pratense species could well be regarded as a promising new source of bioactive natural compounds, which can be used both as a food supplement and a remedy. Full article

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Open AccessArticle

Chemical Composition of Hexane Extract of Citrus aurantifolia and Anti-Mycobacterium tuberculosis Activity of Some of Its Constituents

by Nallely E. Sandoval-Montemayor, Abraham García, Elizabeth Elizondo-Treviño, Elvira Garza-González, Laura Alvarez and María Del Rayo Camacho-Corona

Molecules 2012, 17(9), 11173-11184; https://doi.org/10.3390/molecules170911173 - 19 Sep 2012

Cited by 82 | Viewed by 13307

Abstract

The main aim of this study was to isolate and characterize the active compounds from the hexane extract of the fruit peels of Citrus aurantiifolia, which showed activity against one sensitive and three monoresistant (isoniazid, streptomycin or ethambutol) strains of Mycobacterium tuberculosis [...] Read more.

The main aim of this study was to isolate and characterize the active compounds from the hexane extract of the fruit peels of Citrus aurantiifolia, which showed activity against one sensitive and three monoresistant (isoniazid, streptomycin or ethambutol) strains of Mycobacterium tuberculosis H₃₇Rv. The active extract was fractionated by column chromatography, yielding the following major compounds: 5-geranyloxypsoralen (1); 5-geranyloxy-7-methoxycoumarin (2); 5,7-dimethoxycoumarin (3); 5-methoxypsoralen (4); and 5,8-dimethoxypsoralen (5). The structures of these compounds were elucidated by 1D and 2D NMR spectroscopy. In addition, GC-MS analysis of the hexane extract allowed the identification of 44 volatile compounds, being 5,7-dimethoxycoumarin (15.79%), 3-methyl-1,2-cyclopentanedione (8.27%), 1-methoxy-ciclohexene (8.0%), corylone (6.93%), palmitic acid (6.89%), 5,8-dimethoxypsoralen (6.08%), a-terpineol (5.97%), and umbelliferone (4.36%), the major constituents. Four isolated coumarins and 16 commercial compounds identified by GC-MS were tested against M. tuberculosis H₃₇Rv and three multidrug-resistant M. tuberculosis strains using the Microplate Alamar Blue Assay. The constituents that showed activity against all strains were 5 (MICs = 25–50 mg/mL), 1 (MICs = 50–100 mg/mL), palmitic acid (MICs = 25–50 mg/mL), linoleic acid (MICs = 50–100 mg/mL), oleic acid (MICs = 100 mg/mL), 4-hexen-3-one (MICs = 50–100 mg/mL), and citral (MICs = 50–100 mg/mL). Compound 5 and palmitic acid were the most active ones. The antimycobacterial activity of the hexane extract of C. aurantifolia could be attributed to these compounds. Full article

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Open AccessArticle

In Vitro Antioxidant Activity Potential of Lantadene A, a Pentacyclic Triterpenoid of Lantana Plants

by Chong Grace-Lynn, Ibrahim Darah, Yeng Chen, Lachimanan Yoga Latha, Subramanion L. Jothy and Sreenivasan Sasidharan

Molecules 2012, 17(9), 11185-11198; https://doi.org/10.3390/molecules170911185 - 19 Sep 2012

Cited by 26 | Viewed by 6142

Abstract

Lantadenes are pentacyclic triterpenoids present in the leaves of the plant Lantana camara. In the present study, in vitro antioxidant activity and free radical scavenging capacity of lantadene A was evaluated using established in vitro models such as ferric reducing antioxidant power (FRAP), [...] Read more.

Lantadenes are pentacyclic triterpenoids present in the leaves of the plant Lantana camara. In the present study, in vitro antioxidant activity and free radical scavenging capacity of lantadene A was evaluated using established in vitro models such as ferric reducing antioxidant power (FRAP), 2,2-diphenyl-1-picryl-hydrazyl (DPPH•), hydroxyl radical (OH•), nitric oxide radical (NO•), superoxide anion scavenging activities and ferrous ion chelating assay. Interestingly, lantadene A showed considerable in vitro antioxidant, free radical scavenging capacity activities in a dose dependant manner when compared with the standard antioxidant in nitric oxide scavenging, superoxide anion radical scavenging and ferrous ion chelating assay. These findings show that the lantadene A possesses antioxidant activity with different mechanism of actions towards the different free radicals tested. Since lantadene A is a very popular drug in modern medicine, it is a promising candidate for use as an antioxidant and hepatoprotective agent. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Physicochemical and Antioxidant Properties of Algerian Honey

by Md. Ibrahim Khalil, Mohammed Moniruzzaman, Laïd Boukraâ, Mokhtar Benhanifia, Md. Asiful Islam, Md. Nazmul Islam, Siti Amrah Sulaiman and Siew Hua Gan

Molecules 2012, 17(9), 11199-11215; https://doi.org/10.3390/molecules170911199 - 20 Sep 2012

Cited by 185 | Viewed by 15899

Abstract

The aim of the present study was to characterize the physical, biochemical and antioxidant properties of Algerian honey samples (n = 4). Physical parameters, such as pH, moisture content, electrical conductivity (EC), total dissolved solids (TDS), color intensity, total sugar and sucrose content [...] Read more.

The aim of the present study was to characterize the physical, biochemical and antioxidant properties of Algerian honey samples (n = 4). Physical parameters, such as pH, moisture content, electrical conductivity (EC), total dissolved solids (TDS), color intensity, total sugar and sucrose content were measured. Several biochemical and antioxidant tests were performed to determine the antioxidant properties of the honey samples. The mean pH was 3.84 ± 0.01, and moisture the content was 13.21 ± 0.16%. The mean EC was 0.636 ± 0.001, and the mean TDS was 316.92 ± 0.92. The mean color was 120.58 ± 0.64 mm Pfund, and the mean 5-hydroxymethylfurfural (HMF) content was 21.49 mg/kg. The mean total sugar and reducing sugar contents were 67.03 ± 0.68 g/mL and 64.72 ± 0.52 g/g, respectively. The mean sucrose content was 2.29 ± 0.65%. High mean values of phenolic (459.83 ± 1.92 mg gallic acid/kg), flavonoid (54.23 ± 0.62 mg catechin/kg), ascorbic acid (159.70 ± 0.78 mg/kg), AEAC (278.15 ± 4.34 mg/kg), protein (3381.83 ± 6.19 mg/kg) and proline (2131.47 ± 0.90) contents, as well as DPPH (39.57% ± 4.18) and FRAP activities [337.77 ± 1.01 µM Fe (II)/100 g], were also detected, indicating that Algerian honey has a high antioxidant potential. Strong positive correlations were found between flavonoid, proline and ascorbic acid contents and color intensity with DPPH and FRAP values. Thus, the present study revealed that Algerian honey is a good source of antioxidants. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Salvianolic Acid A Protects the Peripheral Nerve Function in Diabetic Rats through Regulation of the AMPK-PGC1α-Sirt3 Axis

by Xiaoyan Yu, Li Zhang, Xiuying Yang, Huakang Huang, Zhonglin Huang, Lili Shi, Hengai Zhang and Guanhua Du

Molecules 2012, 17(9), 11216-11228; https://doi.org/10.3390/molecules170911216 - 20 Sep 2012

Cited by 57 | Viewed by 7056

Abstract

Salvianolic acid A (SalA) is one of the main efficacious, water-soluble constituents of Salvia miltiorrhiza Bunge. This study investigated the protective effects of SalA on peripheral nerve in diabetic rats. Administration of SalA (0.3, 1 and 3 mg/kg, ig) was started from the [...] Read more.

Salvianolic acid A (SalA) is one of the main efficacious, water-soluble constituents of Salvia miltiorrhiza Bunge. This study investigated the protective effects of SalA on peripheral nerve in diabetic rats. Administration of SalA (0.3, 1 and 3 mg/kg, ig) was started from the 5th week after strepotozotocin (STZ60 mg/kg) intraperitoneal injection and continued for 8 weeks. Paw withdrawal mechanical threshold (PWMT) and motor nerve conduction velocity (MNCV) were used to assess peripheral nerve function. The western blot methods were employed to test the expression levels of serine-threonine liver kinase B1 (LKB1), AMP-activated protein kinase (AMPK), peroxisome proliferator-activated receptor-gamma coactivator-1alpha (PGC-1α), silent information regulator protein3 (sirtuin 3/Sirt3) and neuronal nitric oxide synthase (nNOS) in sciatic nerve. Results showed that SalA administration could increase PWMT and MNCV in diabetic rats; reduce the deterioration of sciatic nerve pathology; increase AMPK phosphorylation level, up-regulate PGC-1α, Sirt3 and nNOS expression, but had no influence on LKB1. These results suggest that SalA has protective effects against diabetic neuropathy. The beneficial effects of SalA on peripheral nerve function in diabetic rats might be attributed to improvements in glucose metabolism through regulation of the AMPK-PGC1α-Sirt3 axis. Full article

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Open AccessArticle

Bioassay-Guided Isolation and Identification of Cytotoxic Compounds from Gymnosperma glutinosum Leaves

by Ramiro Quintanilla-Licea, Rolando Morado-Castillo, Ricardo Gomez-Flores, Hartmut Laatsch, María Julia Verde-Star, Humberto Hernández-Martínez, Patricia Tamez-Guerra, Reyes Tamez-Guerra and Cristina Rodríguez-Padilla

Molecules 2012, 17(9), 11229-11241; https://doi.org/10.3390/molecules170911229 - 20 Sep 2012

Cited by 18 | Viewed by 8771

Abstract

Bioassay-guided fractionation of hexane extracts of Gymnosperma glutinosum (Asteraceae) leaves, collected in North Mexico, afforded the known compounds hentriacontane (1) and (+)-13S,14R,15-trihydroxy-ent-labd-7-ene (2), as well as the new ent-labdane diterpene (−)-13S [...] Read more.

Bioassay-guided fractionation of hexane extracts of Gymnosperma glutinosum (Asteraceae) leaves, collected in North Mexico, afforded the known compounds hentriacontane (1) and (+)-13S,14R,15-trihydroxy-ent-labd-7-ene (2), as well as the new ent-labdane diterpene (−)-13S,14R,15-trihydroxy-7-oxo-ent-labd-8(9)-ene (3). In addition, D-glycero-D-galactoheptitol (4) was isolated from the methanolic extract of this plant. Their structures were established on the basis of high-field 1D- and 2D NMR methods supported by HR-MS data. The cytotoxic activity was determined by using the in vitro L5178Y-R lymphoma murine model. Hentriacontane (1) and the new ent-labdane 3 showed weak cytotoxicity, whereas the ent-labdane 2 showed significant (p < 0.05) and concentration dependent cytotoxicity (up to 78%) against L5178Y-R cells at concentrations ranging from 7.8 to 250 µg/mL. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

A Phytoanticipin Derivative, Sodium Houttuyfonate, Induces in Vitro Synergistic Effects with Levofloxacin against Biofilm Formation by Pseudomonas aeruginosa

by Jing Shao, Huijuan Cheng, Changzhong Wang and Yan Wang

Molecules 2012, 17(9), 11242-11254; https://doi.org/10.3390/molecules170911242 - 20 Sep 2012

Cited by 30 | Viewed by 8365

Abstract

Antibiotic resistance has become the main deadly factor in infections, as bacteria can protect themselves by hiding in a self-constructed biofilm. Consequently, more attention is being paid to the search for “non-antibiotic drugs” to solve this problem. Phytoanticipins, the natural antibiotics from plants, [...] Read more.

Antibiotic resistance has become the main deadly factor in infections, as bacteria can protect themselves by hiding in a self-constructed biofilm. Consequently, more attention is being paid to the search for “non-antibiotic drugs” to solve this problem. Phytoanticipins, the natural antibiotics from plants, could be a suitable alternative, but few works on this aspect have been reported. In this study, a preliminary study on the synergy between sodium houttuyfonate (SH) and levofloxacin (LFX) against the biofilm formation of Pseudomonas aeruginosa was performed. The minimal inhibitory concentrations (MIC) of LFX and SH, anti-biofilm formation and synergistic effect on Pseudomonas aeruginosa, and quantification of alginate were determined by the microdilution method, crystal violet (CV) assay, checkerboard method, and hydroxybiphenyl colorimetry. The biofilm morphology of Pseudomonas aeruginosa was observed by fluorescence microscope and scanning electric microscope (SEM). The results showed that: (i) LFX and SH had an obvious synergistic effect against Pseudomonas aeruginosa with MIC values of 0.25 μg/mL and 128 μg/mL, respectively; (ii) ½ × MIC SH combined with 2 × MIC LFX could suppress the biofilm formation of Pseudomonas aeruginosa effectively, with up to 73% inhibition; (iii) the concentration of alginate decreased dramatically by a maximum of 92% after treatment with the combination of antibiotics; and (iv) more dead cells by fluorescence microscope and more removal of extracellular polymeric structure (EPS) by SEM were observed after the combined treatment of LFX and SH. Our experiments demonstrate the promising future of this potent antimicrobial agent against biofilm-associated infections. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Influence of Sample Processing on the Analysis of Carotenoids in Maize

by Sol Rivera and Ramon Canela

Molecules 2012, 17(9), 11255-11268; https://doi.org/10.3390/molecules170911255 - 21 Sep 2012

Cited by 71 | Viewed by 10132

Abstract

We performed a number of tests with the aim to develop an effective extraction method for the analysis of carotenoid content in maize seed. Mixtures of methanol–ethyl acetate (6:4, v/v) and methanol–tetrahydrofuran (1:1, v/v) were the most effective solvent systems for carotenoid extraction [...] Read more.

We performed a number of tests with the aim to develop an effective extraction method for the analysis of carotenoid content in maize seed. Mixtures of methanol–ethyl acetate (6:4, v/v) and methanol–tetrahydrofuran (1:1, v/v) were the most effective solvent systems for carotenoid extraction from maize endosperm under the conditions assayed. In addition, we also addressed sample preparation prior to the analysis of carotenoids by liquid chromatography (LC). The LC response of extracted carotenoids and standards in several solvents was evaluated and results were related to the degree of solubility of these pigments. Three key factors were found to be important when selecting a suitable injection solvent: compatibility between the mobile phase and injection solvent, carotenoid polarity and content in the matrix. Full article

(This article belongs to the Special Issue Carotenoids)

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Open AccessArticle

Association of KIF6 Variant with Lipid Level and Angiographic Coronary Artery Disease Events Risk in the Han Chinese Population

by Ge Wu, Gui-Bin Li and Bin Dai

Molecules 2012, 17(9), 11269-11280; https://doi.org/10.3390/molecules170911269 - 21 Sep 2012

Cited by 12 | Viewed by 6114

Abstract

KIF6 is a class of molecular motor from the kinesin superfamily. Recently, multiple large studies consisting mainly of Europeans have shown that KIF6 Trp719Arg SNP may be a new predictive factor for coronary artery disease (CAD) event risk. The allelic frequency distribution of [...] Read more.

KIF6 is a class of molecular motor from the kinesin superfamily. Recently, multiple large studies consisting mainly of Europeans have shown that KIF6 Trp719Arg SNP may be a new predictive factor for coronary artery disease (CAD) event risk. The allelic frequency distribution of rs20455 is different in various populations, yet studies among the Han population, one of the largest ethnic groups in the World, have not been conducted. This study is aimed to evaluate the association of KIF6 Trp719Arg variant with angiographic CAD and serum lipid levels in the Han population from northern China. In this case-controlled study, peripheral blood samples were collected from 356 patients and 568 controls of Han Chinese origin. Genotyping was performed by a high-resolution melting curve. The impact of rs20455 on CAD and non-fatal MI was evaluated in a dominant genetic model with stepwise multiple regression analysis. There were no significant differences of genotypes and allele frequency between angiographic CAD and control groups (p > 0.05); however, that of MI and non-MI subgroups were significant differences (p < 0.05). After adjusting for significant risk factors, angiographic CAD risk was not significantly increased in 719Arg allele carriers compared with non-carriers. Further analysis revealed that the non-fatal MI risk and triglyceride levels were significantly higher in 719Arg allele carriers than non-carriers. In conclusion, KIF6 719Arg allele was not an independent risk factor for angiographic CAD susceptibility in Han populations from northern China. However, it was associated with a significantly higher TG level, which may indicate an increased myocardial infarction risk in angiographic CAD patients. Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessArticle

In Vitro Antioxidant Properties of Flavonoids and Polysaccharides Extract from Tobacco (Nicotiana tabacum L.) Leaves

by Qiao-Mei Ru, Li-Juan Wang, Wei-Ming Li, Jing-Lu Wang and Yu-Ting Ding

Molecules 2012, 17(9), 11281-11291; https://doi.org/10.3390/molecules170911281 - 21 Sep 2012

Cited by 42 | Viewed by 9862

Abstract

In the present study, antioxidant properties of flavonoids and polysaccharides from tobacco (Nicotiana tabacum L.) leaves were evaluated in several in vitro systems, e.g., scavenging activities on hydroxyl, superoxide anion, 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radicals, and reducing power. Flavonoids showed [...] Read more.

In the present study, antioxidant properties of flavonoids and polysaccharides from tobacco (Nicotiana tabacum L.) leaves were evaluated in several in vitro systems, e.g., scavenging activities on hydroxyl, superoxide anion, 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radicals, and reducing power. Flavonoids showed much better activity than polysaccharides in scavenging activities on free radicals. When compared to the positive control, ascorbic acid, both showed weaker antioxidant potential. However, flavonoids possessed comparable superoxide anion, DPPH and ABTS radical scavenging abilities to ascorbic acid at high concentration (600 μg/mL). Meanwhile, it was found that flavonoids had prominent effects on the reducing power, which was equivalent to ascorbic acid, and was significantly higher than polysaccharides. These results clearly indicate that flavonoids are effective in scavenging free radicals and have the potential to be powerful antioxidants. Thus, tobacco leaves could be considered as a potential source of natural antioxidants for food, pharmaceutical, cosmetics or nutraceutical industries. Full article

(This article belongs to the Section Natural Products Chemistry)

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Review

Jump to: Editorial, Research, Other

418 KiB

Open AccessReview

Synthetic Approaches and Pharmacological Activity of 1,3,4-Oxadiazoles: A Review of the Literature from 2000–2012

by Cledualdo Soares De Oliveira, Bruno Freitas Lira, José Maria Barbosa-Filho, Jorge Gonçalo Fernandez Lorenzo and Petrônio Filgueiras De Athayde-Filho

Molecules 2012, 17(9), 10192-10231; https://doi.org/10.3390/molecules170910192 - 27 Aug 2012

Cited by 242 | Viewed by 16768

Abstract

This review provides readers with an overview of the main synthetic methodologies for 1,3,4-oxadiazole derivatives, and of their broad spectrum of pharmacological activities as reported over the past twelve years. Full article

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Open AccessReview

Cassia spectabilis (DC) Irwin et Barn: A Promising Traditional Herb in Health Improvement

by Subramanion L. Jothy, Angeline Torey, Ibrahim Darah, Yee Siew Choong, Dharmaraj Saravanan, Yeng Chen, Lachimanan Yoga Latha, Subramanian Deivanai and Sreenivasan Sasidharan

Molecules 2012, 17(9), 10292-10305; https://doi.org/10.3390/molecules170910292 - 29 Aug 2012

Cited by 27 | Viewed by 12071

Abstract

The genus Cassia, comprising about 600 species widely distributed worldwide is well known for its diverse biological and pharmacological properties. Cassia spectabilis (sin Senna spectabilis) (DC) Irwin et Barn (Fabaceae) is widely grown as an ornamental plant in tropical and subtropical [...] Read more.

The genus Cassia, comprising about 600 species widely distributed worldwide is well known for its diverse biological and pharmacological properties. Cassia spectabilis (sin Senna spectabilis) (DC) Irwin et Barn (Fabaceae) is widely grown as an ornamental plant in tropical and subtropical areas. C. spectabilis has been commonly used in traditional medicine for many years. Information in the biomedical literature has indicated the presence of a variety of medicinally-important chemical constituents in C. spectabilis. Pharmacological studies by various groups of investigators have shown that C. spectabilis possesses significant biological activity, such as antibacterial, antibiofilm, antifungal and antioxidant properties. Beside this, toxicity studies of this plant have revealed no toxic effect on mice. In view of the immense medicinal importance of C. spectabilis, this review aimed at compiling all currently available information on C. spectabilis’s botany, phytochemistry, pharmacology, and mechanism of actions, toxicology and its ethnomedicinal uses. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessReview

Promising Therapeutics with Natural Bioactive Compounds for Improving Learning and Memory — A Review of Randomized Trials

by Hemant Kumar, Sandeep Vasant More, Sang-Don Han, Jin-Yong Choi and Dong-Kug Choi

Molecules 2012, 17(9), 10503-10539; https://doi.org/10.3390/molecules170910503 - 3 Sep 2012

Cited by 49 | Viewed by 9437

Abstract

Cognitive disorders can be associated with brain trauma, neurodegenerative disease or as a part of physiological aging. Aging in humans is generally associated with deterioration of cognitive performance and, in particular, learning and memory. Different therapeutic approaches are available to treat cognitive impairment [...] Read more.

Cognitive disorders can be associated with brain trauma, neurodegenerative disease or as a part of physiological aging. Aging in humans is generally associated with deterioration of cognitive performance and, in particular, learning and memory. Different therapeutic approaches are available to treat cognitive impairment during physiological aging and neurodegenerative or psychiatric disorders. Traditional herbal medicine and numerous plants, either directly as supplements or indirectly in the form of food, improve brain functions including memory and attention. More than a hundred herbal medicinal plants have been traditionally used for learning and memory improvement, but only a few have been tested in randomized clinical trials. Here, we will enumerate those medicinal plants that show positive effects on various cognitive functions in learning and memory clinical trials. Moreover, besides natural products that show promising effects in clinical trials, we briefly discuss medicinal plants that have promising experimental data or initial clinical data and might have potential to reach a clinical trial in the near future. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessReview

Extraction of Volatile Oil from Aromatic Plants with Supercritical Carbon Dioxide: Experiments and Modeling

by Jose P. Coelho, Ana F. Cristino, Patrícia G. Matos, Amélia P. Rauter, Beatriz P. Nobre, Rui L. Mendes, João G. Barroso, Ana Mainar, Jose S. Urieta, João M. N. A. Fareleira, Helena Sovová and António F. Palavra

Molecules 2012, 17(9), 10550-10573; https://doi.org/10.3390/molecules170910550 - 5 Sep 2012

Cited by 48 | Viewed by 8720

Abstract

An overview of the studies carried out in our laboratories on supercritical fluid extraction (SFE) of volatile oils from seven aromatic plants: pennyroyal (Mentha pulegium L.), fennel seeds (Foeniculum vulgare Mill.), coriander (Coriandrum sativum L.), savory (Satureja fruticosa Béguinot [...] Read more.

An overview of the studies carried out in our laboratories on supercritical fluid extraction (SFE) of volatile oils from seven aromatic plants: pennyroyal (Mentha pulegium L.), fennel seeds (Foeniculum vulgare Mill.), coriander (Coriandrum sativum L.), savory (Satureja fruticosa Béguinot), winter savory (Satureja montana L.), cotton lavender (Santolina chamaecyparisus) and thyme (Thymus vulgaris), is presented. A flow apparatus with a 1 L extractor and two 0.27 L separators was built to perform studies at temperatures ranging from 298 to 353 K and pressures up to 30.0 MPa. The best compromise between yield and composition compared with hydrodistillation (HD) was achieved selecting the optimum experimental conditions of extraction and fractionation. The major differences between HD and SFE oils is the presence of a small percentage of cuticular waxes and the relative amount of thymoquinone, an oxygenated monoterpene with important biological properties, which is present in the oils from thyme and winter savory. On the other hand, the modeling of our data on supercritical extraction of volatile oil from pennyroyal is discussed using Sovová’s models. These models have been applied successfully to the other volatile oil extractions. Furthermore, other experimental studies involving supercritical CO₂ carried out in our laboratories are also mentioned. Full article

(This article belongs to the Special Issue Terpenoids)

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Open AccessReview

Specific Binding of Anionic Porphyrin and Phthalocyanine to the G-Quadruplex with a Variety of in Vitro and in Vivo Applications

by Hidenobu Yaku, Takashi Murashima, Daisuke Miyoshi and Naoki Sugimoto

Molecules 2012, 17(9), 10586-10613; https://doi.org/10.3390/molecules170910586 - 5 Sep 2012

Cited by 71 | Viewed by 10144

Abstract

The G-quadruplex, a four-stranded DNA structure with stacked guanine tetrads (G-quartets), has recently been attracting attention because of its critical roles in vitro and in vivo. In particular, the G-quadruplex functions as ligands for metal ions and aptamers for various molecules. Interestingly, [...] Read more.

The G-quadruplex, a four-stranded DNA structure with stacked guanine tetrads (G-quartets), has recently been attracting attention because of its critical roles in vitro and in vivo. In particular, the G-quadruplex functions as ligands for metal ions and aptamers for various molecules. Interestingly, the G-quadruplex can show peroxidase-like activity with an anionic porphyrin, iron (III) protoporphyrin IX (hemin). Importantly, hemin binds to G-quadruplexes with high selectivity over single-stranded DNA (ssDNA) and double-stranded DNA (dsDNA), which is attributable to an electrostatic repulsion of phosphate groups in ssDNA and dsDNA. The G-quadruplex and hemin-G-quadruplex complex allow development of sensing techniques to detect DNA, metal ions and proteins. In addition to hemin, anionic phthalocyanines also bind to the G-quadruplex formed by human telomere DNA, specifically over ssDNA and dsDNA. Since the binding of anionic phthalocyanines to the G-quadruplex causes an inhibition of telomerase activity, which plays a role in the immortal growth of cancer cells, anionic phthalocyanines are promising as novel anticancer drug candidates. This review focuses on the specific binding of hemin and anionic phthalocyanines to G-quadruplexes and the applications in vitro and in vivo of this binding property. Full article

(This article belongs to the Special Issue Tetrapyrroles, Porphyrins and Phthalocyanines)

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Open AccessReview

Advances in the Chemical Analysis and Biological Activities of Chuanxiong

by Weixia Li, Yuping Tang, Yanyan Chen and Jin-Ao Duan

Molecules 2012, 17(9), 10614-10651; https://doi.org/10.3390/molecules170910614 - 6 Sep 2012

Cited by 124 | Viewed by 9609

Abstract

Chuanxiong Rhizoma (Chuan-Xiong, CX), the dried rhizome of Ligusticum chuanxiong Hort. (Umbelliferae), is one of the most popular plant medicines in the World. Modern research indicates that organic acids, phthalides, alkaloids, polysaccharides, ceramides and cerebrosides are main components responsible for the bioactivities and [...] Read more.

Chuanxiong Rhizoma (Chuan-Xiong, CX), the dried rhizome of Ligusticum chuanxiong Hort. (Umbelliferae), is one of the most popular plant medicines in the World. Modern research indicates that organic acids, phthalides, alkaloids, polysaccharides, ceramides and cerebrosides are main components responsible for the bioactivities and properties of CX. Because of its complex constituents, multidisciplinary techniques are needed to validate the analytical methods that support CX’s use worldwide. In the past two decades, rapid development of technology has advanced many aspects of CX research. The aim of this review is to illustrate the recent advances in the chemical analysis and biological activities of CX, and to highlight new applications and challenges. Emphasis is placed on recent trends and emerging techniques. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessCorrection

Hasegawa, T., et al. Structure-Odor Relationships of αSantalol Derivatives with Modified Side Chains. Molecules, 2012, 17, 2259-2270

by Toshio Hasegawa, Hiroaki Izumi, Yuji Tajima and Hideo Yamada

Molecules 2012, 17(9), 11292-11293; https://doi.org/10.3390/molecules170911292 - 21 Sep 2012

Cited by 1 | Viewed by 5480

Abstract

The authors are sorry to report that some of the ¹³C-NMR data reported in their recently published paper [1] were incorrect. While this manuscript was in preparation and pending recording of some ¹³C-NMR spectra the data of α-santalol was used as [...] Read more.

The authors are sorry to report that some of the ¹³C-NMR data reported in their recently published paper [1] were incorrect. While this manuscript was in preparation and pending recording of some ¹³C-NMR spectra the data of α-santalol was used as a placeholder. Upon revising the manuscript according to the reviewers’ comments, they mistakenly thought that all spectral data had been replaced by the correct measured data. Consequently the authors wish to make at this time the following corrections to the paper. [...] Full article

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Molecules, Volume 17, Issue 9 (September 2012) – 92 articles , Pages 10000-11293

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