Molecules

11 pages, 356 KiB

Open AccessArticle

Anti-Inflammatory and Antioxidant Components from Hygroryza aristata

by Yu-Ming Chung^1,†, Yu-Hsuan Lan^2,†, Tsong-Long Hwang¹

and Yann-Lii Leu^1,*

¹ Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 33302, Taiwan

² School of Pharmacy, China Medical University, Taichung 40402, Taiwan

^† These authors contributed equally to this work.

Molecules 2011, 16(3), 1917-1927; https://doi.org/10.3390/molecules16031917 - 25 Feb 2011

Cited by 20 | Viewed by 9106

Abstract

Twenty-six known compounds and two new compounds, including a new lignan, (7S*,8R*,7’R*,8’S*)-icariol A₂-9-O-b-xylopyranoside (1), and a new indole alkaloid, hygarine (2), were isolated from the extracts of [...] Read more.

Twenty-six known compounds and two new compounds, including a new lignan, (7S*,8R*,7’R*,8’S*)-icariol A₂-9-O-b-xylopyranoside (1), and a new indole alkaloid, hygarine (2), were isolated from the extracts of Hygroryza aristata (Gramineae). The structures of all compounds were elucidated on the basis of NMR spectral analysis. The compounds (-)-epigallocatechin-3-O-gallate (4) and (-)-epicatechin-3-O-gallate (5) possess free radical scavenging activities and compound 1 could inhibit superoxide anion generation and elastase release by fMLP/CB-induced human neutrophils with IC50 values of 19.33 ± 0.86 and 24.14 ± 1.59 mM, respectively. Full article

(This article belongs to the Section Natural Products Chemistry)

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28 pages, 350 KiB

Open AccessArticle

QSAR Models for CXCR2 Receptor Antagonists Based on the Genetic Algorithm for Data Preprocessing Prior to Application of the PLS Linear Regression Method and Design of the New Compounds Using In Silico Virtual Screening

by Tahereh Asadollahi¹, Shayessteh Dadfarnia¹, Ali Mohammad Haji Shabani¹, Jahan B. Ghasemi^2,* and Maryam Sarkhosh²

¹ Department of Chemistry, Faculty of Science, Yazd University, Yazd 89195, Iran

² Department of Chemistry, Faculty of Science, K. N. Toosi University of Technology, Tehran, Iran

Molecules 2011, 16(3), 1928-1955; https://doi.org/10.3390/molecules16031928 - 25 Feb 2011

Cited by 53 | Viewed by 9235

Abstract

The CXCR2 receptors play a pivotal role in inflammatory disorders and CXCR2 receptor antagonists can in principle be used in the treatment of inflammatory and related diseases. In this study, quantitative relationships between the structures of 130 antagonists of the CXCR2 receptors and [...] Read more.

The CXCR2 receptors play a pivotal role in inflammatory disorders and CXCR2 receptor antagonists can in principle be used in the treatment of inflammatory and related diseases. In this study, quantitative relationships between the structures of 130 antagonists of the CXCR2 receptors and their activities were investigated by the partial least squares (PLS) method. The genetic algorithm (GA) has been proposed for improvement of the performance of the PLS modeling by choosing the most relevant descriptors. The results of the factor analysis show that eight latent variables are able to describe about 86.77% of the variance in the experimental activity of the molecules in the training set. Power prediction of the QSAR models developed with SMLR, PLS and GA-PLS methods were evaluated using cross-validation, and validation through an external prediction set. The results showed satisfactory goodness-of-fit, robustness and perfect external predictive performance. A comparison between the different developed methods indicates that GA-PLS can be chosen as supreme model due to its better prediction ability than the other two methods. The applicability domain was used to define the area of reliable predictions. Furthermore, the in silico screening technique was applied to the proposed QSAR model and the structure and potency of new compounds were predicted. The developed models were found to be useful for the estimation of pIC₅₀ of CXCR2 receptors for which no experimental data is available. Full article

(This article belongs to the Section Medicinal Chemistry)

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17 pages, 211 KiB

Open AccessArticle

Synthesis of New Visnagen and Khellin Furochromone Pyrimidine Derivatives and Their Anti-Inflammatory and Analgesic Activity

by Ameen Ali Abu-Hashem^1,*,†

and Mohamed M. Youssef^2,‡

¹ Departments of Photochemistry, National Research Center, 12622 Dokki, Giza, Egypt

² Department of Chemistry, Faculty of Science, Cairo University, Giza, Egypt

^† Current Address: Department of Chemistry, Faculty of Science, Jazan University, 2097 Jazan, Saudi Arabia.

^‡ Current Address: Department of Chemistry, Faculty of Science, Taif University, Taif, Saudi Arabia.

Molecules 2011, 16(3), 1956-1972; https://doi.org/10.3390/molecules16031956 - 25 Feb 2011

Cited by 81 | Viewed by 11052

Abstract

6-[(4-Methoxy/4,9-dimethoxy)-7-methylfurochromen-5-ylideneamino]-2-thioxo-2,3-dihydropyrimidin-4-ones 1a,b were prepared by reaction of 6-amino-2-thiouracil with visnagen or khellin, respectively. Reaction of 1a,b with methyl iodide afforded furochromenylideneaminomethylsulfanylpyrimidin-4-ones 2a,b. Compounds 2a,b were reacted with secondary aliphatic amines to give the corresponding furochromen-ylideneamino-2-substituted pyrimidin-4-ones 3a–d. Reaction of 3a–d with [...] Read more.

6-[(4-Methoxy/4,9-dimethoxy)-7-methylfurochromen-5-ylideneamino]-2-thioxo-2,3-dihydropyrimidin-4-ones 1a,b were prepared by reaction of 6-amino-2-thiouracil with visnagen or khellin, respectively. Reaction of 1a,b with methyl iodide afforded furochromenylideneaminomethylsulfanylpyrimidin-4-ones 2a,b. Compounds 2a,b were reacted with secondary aliphatic amines to give the corresponding furochromen-ylideneamino-2-substituted pyrimidin-4-ones 3a–d. Reaction of 3a–d with phosphorus oxychloride yielded 6-chlorofurochromenylidenepyrimidinamines 4a–d, which were reacted with secondary amines to afford furochromenylideneamino-2,6-disubstituted pyrimidin-4-ones 5a–d. In addition, reaction of 5a–d with 3-chloropentane-2,4-dione gave 3-chloro-furochromenylpyrimidopyrimidines 6a–d. The latter were reacted with piperazine and morpholine to give 1-(furochromenyl)-pyrimidopyrimidine-3,6,8-triylpiperazines or -3,6,8-triylmorpholines 7a–d. The chemical structures of the newly synthesized compound ware characterized by IR, ¹H-NMR, ¹³C-NMR and mass spectral analysis. These compounds were also screened for their analgesic and anti-inflammatory activities. Some of them, particularly 3–7, exhibited promising activities. Full article

(This article belongs to the Special Issue Cycloaddition Reactions in Organic Synthesis)

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8 pages, 394 KiB

Open AccessArticle

Effect of End Groups on the Raman Spectra of Lycopene and β-Carotene under High Pressure

by Ming-Ming Huo¹, Wei-Long Liu^1,*, Zhi-Ren Zheng^1,*, Wei Zhang¹, Ai-Hua Li¹ and Da-Peng Xu²

¹ Center for Condensed Matter Science and Technology, Department of Physics, Harbin Institute of Technology, Harbin, 150001, China

² College of Physics, Ji Lin University, Changchun 130023, China

Molecules 2011, 16(3), 1973-1980; https://doi.org/10.3390/molecules16031973 - 25 Feb 2011

Cited by 31 | Viewed by 9504

Abstract

The Raman spectra of all-trans-lycopene in n-hexane were measured under high pressure, and the results compared with those of β-carotene. The different pressure effects on Raman spectra are analyzed taking into account the different structures of lycopene and [...] Read more.

The Raman spectra of all-trans-lycopene in n-hexane were measured under high pressure, and the results compared with those of β-carotene. The different pressure effects on Raman spectra are analyzed taking into account the different structures of lycopene and β-carotene molecules. It is concluded that: (a) the vibronic coupling between the S₁ and S₀ states of β-carotene is stronger than that of lycopene, (b) the diabatic frequency increment of the ν₁mode is more susceptible to pressure than that of the ν₂ mode for lycopene, and (c) β-rings rotation can relieve the pressure effect on the C=C bond length in β-carotene. This work provides some insights for elucidating the structural and environmental effects on Raman spectra of carotenoids. Full article

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6 pages, 187 KiB

Open AccessCommunication

A Simple and Practical Solvent-Free Preparation of Polymaleimide

by Xing-Rong Zhang, Bing-Tao Tang and Shu-Fen Zhang^*

State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China

Molecules 2011, 16(3), 1981-1986; https://doi.org/10.3390/molecules16031981 - 28 Feb 2011

Cited by 11 | Viewed by 6190

Abstract

Polymaleimide (PMAI) was synthesized by reacting polymaleic anhydride (PMA) with urea via a solvent-free reaction at 180 °C. The conversion of PMA could reach 95%. This method is simple, practical and environmentally-friendly. The structure of the resulting PMAI was characterized by ¹H-NMR [...] Read more.

Polymaleimide (PMAI) was synthesized by reacting polymaleic anhydride (PMA) with urea via a solvent-free reaction at 180 °C. The conversion of PMA could reach 95%. This method is simple, practical and environmentally-friendly. The structure of the resulting PMAI was characterized by ¹H-NMR and IR. Full article

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36 pages, 897 KiB

Open AccessReview

Chemical Arsenal for the Study of O-GlcNAc

by Eun J. Kim

Department of Science Education-Chemistry Major, Daegu University, Gyeongbuk 712-714, Korea

Molecules 2011, 16(3), 1987-2022; https://doi.org/10.3390/molecules16031987 - 28 Feb 2011

Cited by 27 | Viewed by 12716

Abstract

The concepts of both protein glycosylation and cellular signaling have been influenced by O-linked-β-N-acetylglucosamine (O-GlcNAc) modification (O-GlcNAcylation) on the hydroxyl group of serine or threonine residues. Unlike conventional protein glycosylation, O-GlcNAcylation is localized in the nucleocytoplasm and [...] Read more.

The concepts of both protein glycosylation and cellular signaling have been influenced by O-linked-β-N-acetylglucosamine (O-GlcNAc) modification (O-GlcNAcylation) on the hydroxyl group of serine or threonine residues. Unlike conventional protein glycosylation, O-GlcNAcylation is localized in the nucleocytoplasm and its cycling is a dynamic process that operates in a highly regulated manner in response to various cellular stimuli. These characteristics render O-GlcNAcylation similar to phosphorylation, which has long been considered a major regulatory mechanism in cellular processes. Various efficient chemical approaches and novel mass spectrometric (MS) techniques have uncovered numerous O-GlcNAcylated proteins that are involved in the regulation of many important cellular events. These discoveries imply that O-GlcNAcylation is another major regulator of cellular signaling. However, in contrast to phosphorylation, which is regulated by hundreds of kinases and phosphatases, dynamic O-GlcNAc cycling is catalyzed by only two enzymes: uridine diphospho-N-acetyl-glucosamine:polypeptide β-N-acetylglucosaminyl transferase (OGT) and β-D-N-acetylglucosaminidase (OGA). Many useful chemical tools have recently been used to greatly expand our understanding of the extensive crosstalk between O-GlcNAcylation and phosphorylation and hence of cellular signaling. This review article describes the various useful chemical tools that have been developed and discusses the considerable advances made in the O-GlcNAc field. Full article

(This article belongs to the Special Issue Glycosides)

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9 pages, 207 KiB

Open AccessArticle

Drug Resistance Modulation in Staphylococcus Aureus, a New Biological Activity for Mesoionic Hydrochloride Compounds

by Cledualdo Soares de Oliveira¹, Vivyanne Dos Santos Falcão-Silva³, José Pinto Siqueira-Júnior³, David Peter Harding¹, Bruno Freitas Lira¹, Jorge Gonçalo Fernandes Lorenzo², José Maria Barbosa-Filho² and Petrônio Filgueiras de Athayde-Filho^1,*

¹ Department of Chemistry, Federal University of Paraíba, 58059, João Pessoa, PB, Brazil

² Laboratory of Pharmaceutical Technology, Federal University of Paraíba, 58051, João Pessoa, PB, Brazil

³ Department of Molecular Biology, Federal University of Paraíba, 58059, João Pessoa, PB, Brazil

Molecules 2011, 16(3), 2023-2031; https://doi.org/10.3390/molecules16032023 - 28 Feb 2011

Cited by 22 | Viewed by 9517

Abstract

Two salts of the mesoionic compounds 1,4-diphenyl-5-(5-nitro-2-furanyl)-1,3,4-thiadiazolium-2-thiol chloride (MC-1) and 4-phenyl-5-(5-nitro-2-furanyl)-1,3,4-thiadiazolium-2-phenylamine chloride (MC-2) were synthesized utilizing 1,4-diphenyl-thiosemicarbazide and 5-nitro-2-furoyl chloride as starting materials. Their structures were characterized by IR, ¹H-NMR, ¹³C-NMR and elemental analysis. These compounds were [...] Read more.

Two salts of the mesoionic compounds 1,4-diphenyl-5-(5-nitro-2-furanyl)-1,3,4-thiadiazolium-2-thiol chloride (MC-1) and 4-phenyl-5-(5-nitro-2-furanyl)-1,3,4-thiadiazolium-2-phenylamine chloride (MC-2) were synthesized utilizing 1,4-diphenyl-thiosemicarbazide and 5-nitro-2-furoyl chloride as starting materials. Their structures were characterized by IR, ¹H-NMR, ¹³C-NMR and elemental analysis. These compounds were analyzed for their influence on the effectiveness of norfloxacin, tetracycline, and erythromycin (standard antibiotics) against resistant strains of Staphylococcus aureus. MC-1 and MC-2, at sub-inhibitory concentrations of 16 μg/mL, favourably modulated the antibiotic activity of tetracycline by 16- and 32-fold, respectively (MIC), and that of erythromycin by 4-fold. Full article

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

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21 pages, 275 KiB

Open AccessReview

Antioxidant Therapy as a Potential Approach to Severe Influenza-Associated Complications

by Noboru Uchide^* and Hiroo Toyoda

Department of Clinical Molecular Genetics, School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Molecules 2011, 16(3), 2032-2052; https://doi.org/10.3390/molecules16032032 - 28 Feb 2011

Cited by 118 | Viewed by 17028

Abstract

With the appearance of the novel influenza A (H1N1) virus 2009 strain we have experienced a new influenza pandemic and many patients have died from severe complications associated with this pandemic despite receiving intensive care. This suggests that a definitive medical treatment for [...] Read more.

With the appearance of the novel influenza A (H1N1) virus 2009 strain we have experienced a new influenza pandemic and many patients have died from severe complications associated with this pandemic despite receiving intensive care. This suggests that a definitive medical treatment for severe influenza-associated complications has not yet been established. Many studies have shown that superoxide anion produced by macrophages infiltrated into the virus-infected organs is implicated in the development of severe influenza-associated complications. Selected antioxidants, such as pyrrolidine dithiocabamate, N-acetyl-L-cysteine, glutathione, nordihydroguaiaretic acid, thujaplicin, resveratrol, (+)-vitisin A, ambroxol, ascorbic acid, 5,7,4-trihydroxy-8-methoxyflavone, catechins, quercetin 3-rhamnoside, iso- quercetin and oligonol, inhibit the proliferation of influenza virus and scavenge superoxide anion. The combination of antioxidants with antiviral drugs synergistically reduces the lethal effects of influenza virus infections. These results suggest that an agent with antiviral and antioxidant activities could be a drug of choice for the treatment of patients with severe influenza-associated complications. This review article updates knowledge of antioxidant therapy as a potential approach to severe influenza-associated complications. Full article

(This article belongs to the Special Issue Antioxidants)

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12 pages, 327 KiB

Open AccessArticle

Potent Anti-Platelet Constituents from Centaurea iberica

by Amna Nisar Khan¹, Itrat Fatima¹, Urooj Abdul Khaliq¹, Abdul Malik^1,*, Ghulam Abbas Miana², Zia-ur-Rehman Qureshi³ and Huma Rasheed³

¹ International Centre for Chemical and Biological Sciences, HEJ Research Institute of Chemistry, University of Karachi, Karachi 75270, Pakistan

² Riphah Institute of Pharmaceutical Sciences, Riphah International University, 7th Avenue, G-7/4 Islamabad, Pakistan

³ International Centre for Chemical and Biological Sciences, Dr. Panjwani Centre for Molecular Medicine and Drug Research, University of Karachi, Karachi 75270, Pakistan

Molecules 2011, 16(3), 2053-2064; https://doi.org/10.3390/molecules16032053 - 28 Feb 2011

Cited by 19 | Viewed by 6916

Abstract

New naturally occurring nitrogenous compounds 1 and 2, along with a new dimeric lignan glucoside 3, have been isolated from the ethyl acetate soluble fraction of Centaurea iberica. Their structures have been elucidated through spectroscopic techniques. All the isolated compounds [...] Read more.

New naturally occurring nitrogenous compounds 1 and 2, along with a new dimeric lignan glucoside 3, have been isolated from the ethyl acetate soluble fraction of Centaurea iberica. Their structures have been elucidated through spectroscopic techniques. All the isolated compounds showed significant platelet aggregation inhibition. Full article

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10 pages, 146 KiB

Open AccessArticle

From Symmetric Glycerol Derivatives to Dissymmetric Chlorohydrins

by Carmen Solarte, Marc Escribà, Jordi Eras, Gemma Villorbina

, Ramon Canela^*

and Mercè Balcells

Department of Chemistry, Lleida University, Alcalde Rovira Roure 191, 25198 Lleida, Spain

Molecules 2011, 16(3), 2065-2074; https://doi.org/10.3390/molecules16032065 - 2 Mar 2011

Cited by 7 | Viewed by 6692

Abstract

The anticipated worldwide increase in biodiesel production will result in an accumulation of glycerol for which there are insufficient conventional uses. The surplus of this by-product has increased rapidly during the last decade, prompting a search for new glycerol applications. We describe here [...] Read more.

The anticipated worldwide increase in biodiesel production will result in an accumulation of glycerol for which there are insufficient conventional uses. The surplus of this by-product has increased rapidly during the last decade, prompting a search for new glycerol applications. We describe here the synthesis of dissymmetric chlorohydrin esters from symmetric 1,3-dichloro-2-propyl esters obtained from glycerol. We studied the influence of two solvents: 1,4-dioxane and 1-butanol and two bases: sodium carbonate and 1-butylimidazole, on the synthesis of dissymmetric chlorohydrin esters. In addition, we studied the influence of other bases (potassium and lithium carbonates) in the reaction using 1,4-dioxane as the solvent. The highest yield was obtained using 1,4-dioxane and sodium carbonate. Full article

(This article belongs to the Special Issue Asymmetric Synthesis)

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9 pages, 250 KiB

Open AccessArticle

In Vitro Inhibitory Effects of Cyandin-3-rutinoside on Pancreatic α-Amylase and Its Combined Effect with Acarbose

by Sarinya Akkarachiyasit¹, Sirintorn Yibchok-Anun¹, Sumrit Wacharasindhu² and Sirichai Adisakwattana^3,4,*

¹ Department of Pharmacology, Faculty of Veterinary Science, Chulalongkorn University, Bangkok 10330, Thailand

² Natural Products Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand

³ Department of Transfusion Medicine, Faculty of Allied Health Sciences, The Medical Food Research and Development Center, Chulalongkorn University, Bangkok 10330, Thailand

⁴ Program in Nutrition and Dietetics, Faculty of Allied Health Sciences, Chulalongkorn University, Bangkok 10330, Thailand

Molecules 2011, 16(3), 2075-2083; https://doi.org/10.3390/molecules16032075 - 2 Mar 2011

Cited by 80 | Viewed by 8652

Abstract

The inhibitory activity on pancreatic α-amylase by cyanidin-3-rutinoside was examined in vitro. The IC₅₀ value of cyanidin-3-rutinoside against pancreatic α-amylase was 24.4 ± 0.1 μM. The kinetic analysis revealed that pancreatic α-amylase was inhibited by cyanidin-3-rutinoside in a non-competitive manner. The [...] Read more.

The inhibitory activity on pancreatic α-amylase by cyanidin-3-rutinoside was examined in vitro. The IC₅₀ value of cyanidin-3-rutinoside against pancreatic α-amylase was 24.4 ± 0.1 μM. The kinetic analysis revealed that pancreatic α-amylase was inhibited by cyanidin-3-rutinoside in a non-competitive manner. The additive inhibition of a combination of cyanidin-3-rutinoside with acarbose against pancreatic α-amylase was also found. These results provide the first evidence for the effect of cyanidin-3-rutinoside in a retarded absorption of carbohydrates by inhibition of pancreatic α-amylase which may be useful as a potential inhibitor for prevention and treatment of diabetes mellitus. Full article

(This article belongs to the Section Medicinal Chemistry)

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13 pages, 2709 KiB

Open AccessArticle

Luteolin Isolated from the Medicinal Plant Elsholtzia rugulosa (Labiatae) Prevents Copper-Mediated Toxicity in β-Amyloid Precursor Protein Swedish Mutation Overexpressing SH-SY5Y Cells

by Rui Liu¹, Fanrui Meng¹, Li Zhang¹, Ailin Liu¹, Hailin Qin¹, Xi Lan¹, Lin Li² and Guanhua Du^1,*

¹ Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

² Xuanwu Hospital Capital Medical University, Beijing 100053, China

Molecules 2011, 16(3), 2084-2096; https://doi.org/10.3390/molecules16032084 - 2 Mar 2011

Cited by 65 | Viewed by 9823

Abstract

Luteolin, a 3’,4’,5,7-tetrahydroxyflavone, is a plant flavonoid and pharmacologically active agent that has been isolated from several plant species. In the present study, the effects of luteolin obtained from the medicinal plant Elsholtzia rugulosa and the related mechanisms were examined in an Alzheimer's [...] Read more.

Luteolin, a 3’,4’,5,7-tetrahydroxyflavone, is a plant flavonoid and pharmacologically active agent that has been isolated from several plant species. In the present study, the effects of luteolin obtained from the medicinal plant Elsholtzia rugulosa and the related mechanisms were examined in an Alzheimer's disease (AD) cell model. In this model, copper was used to exacerbate the neurotoxicity in β-amyloid precursor protein Swedish mutation stably overexpressed SH-SY5Y cells (named “APPsw cells” for short). Based on this model, we demonstrated that luteolin increased cell viability, reduced intracellular ROS generation, enhanced the activity of SOD and reversed mitochondrial membrane potential dissipation. Inhibition of caspase-related apoptosis was consistently involved in the neuroprotection afforded by luteolin. Furthermore, it down-regulated the expression of AβPP and lowered the secretion of Aβ_1-42. These results indicated that luteolin from the Elsholtzia rugulosa exerted neroprotective effects through mechanisms that decrease AβPP expression, lower Aβ secretion, regulate the redox imbalance, preserve mitochondrial function, and depress the caspase family-related apoptosis. Full article

(This article belongs to the Section Natural Products Chemistry)

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10 pages, 122 KiB

Open AccessReview

Positive Allosteric Modulators of Type 5 Metabotropic Glutamate Receptors (mGluR5) and Their Therapeutic Potential for the Treatment of CNS Disorders

by Richard M. Cleva and M. Foster Olive^*

Department of Psychology, Arizona State University, Tempe, Arizona 85287, USA

Molecules 2011, 16(3), 2097-2106; https://doi.org/10.3390/molecules16032097 - 2 Mar 2011

Cited by 67 | Viewed by 10859

Abstract

Studies utilizing selective pharmacological antagonists or targeted gene deletion have demonstrated thattype 5 metabotropic glutamate receptors (mGluR5) are critical mediators and potential therapeutic targets for the treatment of numerous disorders of the central nervous system (CNS), including depression, anxiety, drug addiction, chronic pain, [...] Read more.

Studies utilizing selective pharmacological antagonists or targeted gene deletion have demonstrated thattype 5 metabotropic glutamate receptors (mGluR5) are critical mediators and potential therapeutic targets for the treatment of numerous disorders of the central nervous system (CNS), including depression, anxiety, drug addiction, chronic pain, Fragile X syndrome, Parkinson’s disease, and gastroesophageal reflux disease. However, in recent years, the development of positive allosteric modulators (PAMs) of the mGluR5 receptor have revealed that allosteric activation of this receptor may also be of potential therapeutic benefit for the treatment of other CNS disorders, including schizophrenia, cognitive deficits associated with chronic drug use, and deficits in extinction learning. Here we summarize the discovery and characterization of various mGluR5 PAMs, with an emphasis on those that are systemically active. We will also review animal studies showing that these molecules have potential efficacy as novel antipsychotic agents. Finally, we will summarize findings that suggest that mGluR5 PAMs have pro-cognitive effects such as the ability toenhance synaptic plasticity, improve performance in various learning and memory tasks, including extinction of drug-seeking behavior, and reverse cognitive deficits produced by chronic drug use. Full article

(This article belongs to the Special Issue Neuroactive Compounds)

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12 pages, 238 KiB

Open AccessArticle

Detection of Cytotoxic Activity of Lectin on Human Colon Adenocarcinoma (Sw480) and Epithelial Cervical Carcinoma (C33-A)

by Carmen Valadez-Vega^1,*, Gerardo Alvarez-Manilla², Leticia Riverón-Negrete³, Alejandro García-Carrancá⁴, José A. Morales-González¹

, Clara Zuñiga-Pérez¹, Eduardo Madrigal-Santillán¹

, Jaime Esquivel-Soto⁵, Cesar Esquivel-Chirino⁵, Roberto Villagómez-Ibarra⁶, Mirandeli Bautista¹

and Ángel Morales-González⁷

¹ Instituto de Ciencias de la Salud, Universidad Autónoma del Estado de Hidalgo, Ex-Hacienda de la Concepción, Tilcuautla, 42080 Pachuca de Soto, Hgo, Mexico

² Ezose Sciences Inc, Pine Brook, New Jersey 07058, USA

³ Parasitología Experimental, Instituto Nacional de Pediatría, Mexico, D.F. Mexico

⁴ Laboratorio de Virus y Cáncer, Unidad de Investigación Biomédica en Cáncer. Instituto de Investigaciones Biomédicas, Universidad Nacional Autónoma de México and Instituto Nacional de Cancerología, Secretaría de Salud, Mexico, D.F., Mexico

⁵ Facultad de Odontología, Universidad Nacional Autónoma de México (UNAM), México, D.F., Mexico

⁶ Instituto de Ciencias Básicas e Ingeniería, Universidad Autónoma del Estado de Hidalgo, Pachuca, Hidalgo, Mexico

⁷ Escuela Superior de Cómputo, Instituto Politécnico Nacional, México, D.F., Mexico

Molecules 2011, 16(3), 2107-2118; https://doi.org/10.3390/molecules16032107 - 2 Mar 2011

Cited by 32 | Viewed by 9321

Abstract

Lectins comprise a heterogeneous class of proteins that recognize the carbohydrate moieties of glycoconjugates with high specificity. Numerous studies have shown that lectins are capable of recognizing specific carbohydrate moieties displayed by malignant cells or tissues. The present work was performed to investigate [...] Read more.

Lectins comprise a heterogeneous class of proteins that recognize the carbohydrate moieties of glycoconjugates with high specificity. Numerous studies have shown that lectins are capable of recognizing specific carbohydrate moieties displayed by malignant cells or tissues. The present work was performed to investigate the effects of tepary bean (Phaseolus acutifolius) lectins on proliferation, colony formation, and alteration of DNA synthesis of human malignant cells. Tepary bean lectin showed dose dependent effects on the inhibition of viability as well as on colony formation in two human malignant cells lines (C33-A, Sw480); By contrast, tepary bean lectin only showed significant effects on DNA synthesis on Sw480 cells. Our results provide evidence of the anti- proliferative and cytotoxic effects of the tepary bean lectins on C33-A and Sw480 cells lines. Full article

(This article belongs to the Section Molecular Diversity)

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16 pages, 2235 KiB

Open AccessArticle

Tamm-Horsfall Glycoprotein Enhances PMN Phagocytosis by Binding to Cell Surface-Expressed Lactoferrin and Cathepsin G That Activates MAP Kinase Pathway

by Syue-Cian Siao¹, Ko-Jen Li²

, Song-Chou Hsieh², Cheng-Han Wu², Ming-Chi Lu³, Chang-Youh Tsai⁴

and Chia-Li Yu^1,2,*

¹ Institute of Molecular Medicine, National Taiwan University College of Medicine, No. 7 Chung-Shan South Road, Taipei 100, Taiwan

² Department of Internal Medicine, National Taiwan University Hospital and National Taiwan University College of Medicine, No.7 Chung-Shan South Road, Taipei 100, Taiwan

³ Division of Allergy, Immunology and Rheumatology, Buddhist Dalin Tzu-Chi General Hospital, No.2 Ming-Shen Road, Dalin, Chia-Yi, Taiwan

⁴ Section of Allergy, Immunology and Rheumatology, Taipei-Veterans General Hospital, No.201 Section 2, Shih-Pai Road, Taipei 11217, Taiwan

Molecules 2011, 16(3), 2119-2134; https://doi.org/10.3390/molecules16032119 - 3 Mar 2011

Cited by 20 | Viewed by 10991

Abstract

The molecular basis of polymorphonuclear neutrophil (PMN) phagocytosis-enhancing activity (PEA) by human purified urinary Tamm-Horsfall glyco- protein (THP) has not been elucidated. In this study, we found human THP bound to lactoferrin (LF) and cathepsin G (CG) expressed on the surface of PMN, [...] Read more.

The molecular basis of polymorphonuclear neutrophil (PMN) phagocytosis-enhancing activity (PEA) by human purified urinary Tamm-Horsfall glyco- protein (THP) has not been elucidated. In this study, we found human THP bound to lactoferrin (LF) and cathepsin G (CG) expressed on the surface of PMN, identified by a proteomic study with MALDI-TOF- LC/LC/mass spectrometric analysis. Pre-incubation of 10% SDS-PAGE electrophoresed PMN lysates with monoclonal anti-LF or anti-CG antibody reduced the binding with THP. To elucidate the signaling pathway of THP on PMN activation, we found THP enhanced ERK1/2 phosphorylation, reduced p38 MAP kinase phosphorylation, but had no effect on DNA binding of the five NF-kB family members in PMN. To further clarify whether the carbohydrate-side chains or protein-core structure in THP molecule is responsible for THP-PEA, THP was cleaved by different degrading enzymes with carbohydrate specificity (neuraminidase and β-galactosidase), protein specificity (V8 protease and proteinase K) or glycoconjugate specificity (carboxylpeptidase Y and O-sialoglycoprotein endopeptidase). We clearly demonstrated that the intact protein-core structure in THP molecule was more important for THP-PEA than carbohydrate-side chains. Putting these results together, we conclude that THP adheres to surface-expressed LF and CG on PMN and transduces signaling via the MAP kinase pathway to enhance PMN phagocytosis. Full article

(This article belongs to the Special Issue Glycosides)

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11 pages, 136 KiB

Open AccessArticle

In-Vitro Antibacterial Properties of Crude Aqueous and n-Hexane Extracts of the Husk of Cocos nucifera

by Taiwo Adesola Akinyele¹, Omobola Oluranti Okoh², David Ayinde Akinpelu³ and Anthony Ifeanyi Okoh^1,*

¹ Applied and Environmental Microbiology Research Group (AEMREG), Department of Biochemistry and Microbiology, University of Fort Hare, P/Bag X1314, Alice 5700, South Africa

² Department of Chemistry, University of Fort Hare, Alice 5700, South Africa

³ Department of Microbiology Obafemi Awolowo University, Ile Ife 220005, Nigeria

Molecules 2011, 16(3), 2135-2145; https://doi.org/10.3390/molecules16032135 - 3 Mar 2011

Cited by 23 | Viewed by 9192

Abstract

The increasing numbers of cases of antibiotic resistance among pathogenic bacteria such as Vibrio species poses a major problem to the food and aquaculture industries, as most antibiotics are no longer effective in controlling pathogenic bacteria affecting these industries. Therefore, this study was [...] Read more.

The increasing numbers of cases of antibiotic resistance among pathogenic bacteria such as Vibrio species poses a major problem to the food and aquaculture industries, as most antibiotics are no longer effective in controlling pathogenic bacteria affecting these industries. Therefore, this study was carried out to assess the antibacterial potentials of crude aqueous and n-hexane extracts of the husk of Cocos nucifera against some selected Vibrio species and other bacterial pathogens including those normally implicated in food and wound infections. The crude extracts were screened against forty-five strains of Vibrio pathogens and twenty-five other bacteria isolates made up of ten Gram positive and fifteen Gram negative bacteria. The aqueous extract was active against 17 of the tested bacterial and 37 of the Vibrio isolates; while the n-hexane extract showed antimicrobial activity against 21 of the test bacteria and 38 of the test Vibrio species. The minimum inhibitory concentrations (MICs) of the aqueous and n-hexane extracts against the susceptible bacteria ranged between 0.6–5.0 mg/mL and 0.3–5.0 mg/mL respectively, while the time kill study result for the aqueous extract ranged between 0.12 Log₁₀ and 4.2 Log₁₀ cfu/mL after 8 hours interaction in 1 × MIC and 2 × MIC. For the n-hexane extract, the log reduction ranged between 0.56 Log₁₀ and 6.4 Log₁₀ cfu/mL after 8 hours interaction in 1 × MIC and 2 × MIC. This study revealed the huge potential of C. nucifera extracts as alternative therapies against microbial infections. Full article

(This article belongs to the Section Natural Products Chemistry)

45 pages, 390 KiB

Open AccessReview

Antiplasmodial Natural Products

by Cláudio R. Nogueira and Lucia M. X. Lopes^*

Instituto de Química, Universidade Estadual Paulista, UNESP, C. P. 355, 14801-970, Araraquara, SP, Brazil

Molecules 2011, 16(3), 2146-2190; https://doi.org/10.3390/molecules16032146 - 4 Mar 2011

Cited by 105 | Viewed by 13727

Abstract

Malaria is a human infectious disease that is caused by four species of Plasmodium. It is responsible for more than 1 million deaths per year. Natural products contain a great variety of chemical structures and have been screened for antiplasmodial activity as potential [...] Read more.

Malaria is a human infectious disease that is caused by four species of Plasmodium. It is responsible for more than 1 million deaths per year. Natural products contain a great variety of chemical structures and have been screened for antiplasmodial activity as potential sources of new antimalarial drugs. This review highlights studies on natural products with antimalarial and antiplasmodial activity reported in the literature from January 2009 to November 2010. A total of 360 antiplasmodial natural products comprised of terpenes, including iridoids, sesquiterpenes, diterpenes, terpenoid benzoquinones, steroids, quassinoids, limonoids, curcubitacins, and lanostanes; flavonoids; alkaloids; peptides; phenylalkanoids; xanthones; naphthopyrones; polyketides, including halenaquinones, peroxides, polyacetylenes, and resorcylic acids; depsidones; benzophenones; macrolides; and miscellaneous compounds, including halogenated compounds and chromenes are listed in this review. Full article

(This article belongs to the Section Natural Products Chemistry)

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27 pages, 583 KiB

Open AccessReview

Tannins of Constant Structure in Medicinal and Food Plants—Hydrolyzable Tannins and Polyphenols Related to Tannins

by Takuo Okuda^1,* and Hideyuki Ito²

¹ Emeritus Professor, Okayama University, Tsushima-naka, Okayama 700, Japan

² Division of Pharmaceutical Sciences, Okayama University Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Tsushima-naka, Okayama 700, Japan

Molecules 2011, 16(3), 2191-2217; https://doi.org/10.3390/molecules16032191 - 4 Mar 2011

Cited by 247 | Viewed by 23656

Abstract

In addition to the commonly used classification as hydrolyzable tannins and condensed tannins, tannins can also be categorized into two other types: polyphenols of constant chemical structure (Type A) and polyphenols of variable composition (Type B). Both types of tannins and related polyphenols [...] Read more.

In addition to the commonly used classification as hydrolyzable tannins and condensed tannins, tannins can also be categorized into two other types: polyphenols of constant chemical structure (Type A) and polyphenols of variable composition (Type B). Both types of tannins and related polyphenols account for a large part of plant polyphenols, but accurate structure-activity correlations on a molecular basis can be determined mainly for type A compounds, among which are hydrolysable tannins such as the ellagitannins and their oxidized congeners, some gallotannins, epigallocatechin gallate, caffetannins, etc. Among the activities determined on a molecular basis are the chemical, biological and pharmacological actions such as superoxide anion scavenging, apoptosis, antitumor, anti-EVB, anti-MRSA and anti-plasmin inhibitory activities, etc., in addition to their fundamental activities, i.e., binding to proteins, large molecular compounds and metallic ions, and antioxidant activities. Some structure-specific activities were found for the condensation of dehydroellagitannins with co-existing compounds under mild conditions, and the host-mediated antitumor actions of ellagitannin oligomers. Structures and activities of metabolites of geraniin, a dehydroellagitannin, were revealed. Some stilbenoids and phlorotannins of firm structures have been known to have many activities similar to those of the type A tannins. Full article

(This article belongs to the Special Issue Tannins)

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15 pages, 904 KiB

Open AccessArticle

Microwave-Assisted Extraction of Phenolic Antioxidants from Potato Peels

by Ashutosh Singh^1,*, Kebba Sabally², Stan Kubow², Danielle J. Donnelly³, Yvan Gariepy¹, Valérie Orsat¹ and G.S.V. Raghavan¹

¹ Department of Bioresource Engineering, McGill University, 21,111 Lakeshore Rd., Sainte-Anne-de-Bellevue, QC H9X 3V9, Canada

² School of Dietetics & Human Nutrition, McGill University, QC H9X 3V9, Canada

³ Department of Plant Science, McGill University, QC H9X 3V9, Canada

Molecules 2011, 16(3), 2218-2232; https://doi.org/10.3390/molecules16032218 - 7 Mar 2011

Cited by 127 | Viewed by 13657

Abstract

A response surface method was used to optimize the microwave-assisted extraction parameters such as extraction time (t) (min), solvent (methanol) concentration (S) (v/v) and microwave power level (MP) for extraction of antioxidants from potato peels. Max. total [...] Read more.

A response surface method was used to optimize the microwave-assisted extraction parameters such as extraction time (t) (min), solvent (methanol) concentration (S) (v/v) and microwave power level (MP) for extraction of antioxidants from potato peels. Max. total phenolics content of 3.94 mg g⁻¹ dry weight (dw) was obtained at S of 67.33%, t of 15 min and a MP of 14.67%. For ascorbic acid (1.44 mg g⁻¹dw), caffeic acid (1.33 mg g⁻¹ dw), ferulic acid (0.50 mg g⁻¹dw) max contents were obtained at S of 100%, t of 15 min, and MP of 10%, while the max chlorogenic acid content (1.35 mg g⁻¹dw) was obtained at S of 100%, t of 5 min, and MP of 10%. The radical scavenging activity of the extract was evaluated by using the DPPH assay and optimum antioxidant activity was obtained at S of 100%, t of 5 min, and MP of 10%. Full article

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20 pages, 280 KiB

Open AccessReview

Analgesic-like Activity of Essential Oils Constituents

by Damião Pergentino De Sousa

Department of Physiology, Federal University of Sergipe, CEP 49100-000, São Cristóvão, SE, Brazil

Molecules 2011, 16(3), 2233-2252; https://doi.org/10.3390/molecules16032233 - 7 Mar 2011

Cited by 160 | Viewed by 22062

Abstract

Research on neuroactive drugs is a pharmaceutical sector of high interest and growth. The discovery of efficient drugs that can relieve pain is a subject of research in the pharmaceutical industry and academic field because pain is a symptom of many diseases. This [...] Read more.

Research on neuroactive drugs is a pharmaceutical sector of high interest and growth. The discovery of efficient drugs that can relieve pain is a subject of research in the pharmaceutical industry and academic field because pain is a symptom of many diseases. This review will summarize results on the discovery of essential oil constituents with analgesic-like activity from the chemical and pharmacological perspectives. Overall, 43 bioactive compounds were selected in nociception models. Among them, 62.8% were monoterpenes, 18.6% sesquiterpenes and other constituents represented 18.6%. The data show the potential of this group of natural product chemicals as analgesic drugs that may be useful for therapeutic purposes. Full article

(This article belongs to the Special Issue Neuroactive Compounds)

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6 pages, 205 KiB

Open AccessCommunication

In Vitro Cytotoxic Evaluation of a Novel Phosphinyl Derivative of Boldine

by Franz A. Thomet¹, Pablo Piñol², Joan Villena² and Patricio G. Reveco^1,*

¹ Department of Chemistry, Universidad Técnica Federico Santa María, Avenida España N° 1680, Valparaíso, Chile

² Centro Regional de Estudios en Alimentos Saludables (CREAS), Department of Biomedical Science, School of Medicine, Universidad de Valparaíso, Avenida Hontaneda N° 2664, Valparaíso, Chile

Molecules 2011, 16(3), 2253-2258; https://doi.org/10.3390/molecules16032253 - 7 Mar 2011

Cited by 6 | Viewed by 7088

Abstract

2,9-Dimethoxymethylboldine (2), 2,9-dimethoxymethyl-3-bromoboldine (3) and 2,9-dimethoxymethyl-3-diphenylphosphinylboldine (4) have been synthesized in an effort to find compounds with potential pharmacological applications. The cytotoxic activities of the natural precursor 1 and these three derivatives have been measured as IC [...] Read more.

2,9-Dimethoxymethylboldine (2), 2,9-dimethoxymethyl-3-bromoboldine (3) and 2,9-dimethoxymethyl-3-diphenylphosphinylboldine (4) have been synthesized in an effort to find compounds with potential pharmacological applications. The cytotoxic activities of the natural precursor 1 and these three derivatives have been measured as IC₅₀ inhibitory growth. The diphenylphosphinyl derivative 4 showed a significant cytotoxic activity on two breast cancer cell lines, namely MCF-7 and MDA-MB-231, with IC₅₀ values of 55.5 and 62.7 [µM], respectively. These results suggest that the kind of structural modifications introduced to synthesize compound 4 represent a promising way to enhance the cytotoxic activity of boldine derivatives. Full article

(This article belongs to the Section Natural Products Chemistry)

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9 pages, 214 KiB

Open AccessArticle

Diterpenoid Tanshinones and Phenolic Acids from Cultured Hairy Roots of Salvia miltiorrhiza Bunge and Their Antimicrobial Activities

by Jianglin Zhao¹, Jingfeng Lou¹, Yan Mou¹, Peiqin Li¹, Jianyong Wu² and Ligang Zhou^1,*

¹ College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, China

² Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, China

Molecules 2011, 16(3), 2259-2267; https://doi.org/10.3390/molecules16032259 - 7 Mar 2011

Cited by 82 | Viewed by 11116

Abstract

Four diterpenoid tanshinones and three phenolic acids were isolated from the crude ethanol extract of the cultured hairy roots of Salvia miltiorrhiza Bunge by bioassay-guided fractionation. By means of physicochemical and spectrometric analysis, they were identified as tanshinone ΙΙA (1), tanshinone [...] Read more.

Four diterpenoid tanshinones and three phenolic acids were isolated from the crude ethanol extract of the cultured hairy roots of Salvia miltiorrhiza Bunge by bioassay-guided fractionation. By means of physicochemical and spectrometric analysis, they were identified as tanshinone ΙΙA (1), tanshinone Ι (2), cryptotanshinone (3), dihydrotanshinone Ι (4), rosmarinic acid (5), caffeic acid (6), and danshensu (7). These compounds were evaluated to show a broad antimicrobial spectrum of activity on test microorganisms including eight bacterial and one fungal species. Among the four tanshinones, cryptotanshinone (3) and dihydrotanshinone Ι (4) exhibited stronger antimicrobial activity than tanshinone ΙΙA (1) and tanshinone Ι (2). The results indicated that the major portion of the antimicrobial activity was due to the presence of tanshinones and phenolic acids in S. miltiorrhiza hairy roots, which could be used as the materials for producing antimicrobial agents for use in agricultural practice in the future. Full article

(This article belongs to the Collection Bioactive Compounds)

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6 pages, 122 KiB

Open AccessArticle

Lignans and Other Constituents from Aerial Parts of Haplophyllum Villosum

by Parimah Parhoodeh, Mawardi Rahmani^*, Najihah Mohd Hashim, Mohd Aspollah Sukari and Gwendoline Ee Cheng Lian

Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia

Molecules 2011, 16(3), 2268-2273; https://doi.org/10.3390/molecules16032268 - 7 Mar 2011

Cited by 20 | Viewed by 6641

Abstract

During our phytochemical investigation of Haplophyllum villosum (Rutaceae), a perennial herb from Iran, a new 4,8-diaryl-3,7-dioxobicyclo-(3,3,0)-octane type lignan, eudesmin A (1), together with four known compounds–eudesmin (2), haplamine (3), umbelliferone (4) and scopoletin (5 [...] Read more.

During our phytochemical investigation of Haplophyllum villosum (Rutaceae), a perennial herb from Iran, a new 4,8-diaryl-3,7-dioxobicyclo-(3,3,0)-octane type lignan, eudesmin A (1), together with four known compounds–eudesmin (2), haplamine (3), umbelliferone (4) and scopoletin (5)–were isolated from aerial parts of the plant. The structures of the compounds were elucidated using NMR spectral analysis (¹H-NMR,¹³C-NMR, HSQC, COSY and HMBC) as well as UV, IR and MS spectra and comparison with previously reported data. Full article

(This article belongs to the Collection Bioactive Compounds)

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11 pages, 212 KiB

Open AccessArticle

Synthesis and Biological Evaluation of 4-Aroyl-6,7,8-Trimethoxyquinolines as a Novel Class of Anticancer Agents

by Cheng-Chih Hsieh^1,2, Hsueh-Yun Lee³, Chih-Ying Nien³, Ching-Chuan Kuo⁴, Chi-Yen Chang⁴, Jang-Yang Chang^4,* and Jing-Ping Liou^3,*

¹ Graduate Institute of Medical Sciences, National Defense Medical Center, No.161, Sec.6. Min-Chuan E. Road, Taipei 114, Taiwan

² Department of Pharmacy Practice, Tri-Service General Hospital, No.325, Sec.2. Cheng-Kung Road, Taipei 114, Taiwan

³ School of Pharmacy, College of Pharmacy, Taipei Medical University, No. 250 Wuxing Street, Taipei 11031, Taiwan

⁴ National Institute of Cancer Research, National Health Research Institutes. 2 F, No.367, Sheng Li Road, Tainan 704, Taiwan

Molecules 2011, 16(3), 2274-2284; https://doi.org/10.3390/molecules16032274 - 7 Mar 2011

Cited by 3 | Viewed by 7592

Abstract

A series of 2-aroyl and 2-aryl-5,6,7-trimethoxyquinoline and 4-aroyl-6,7,8-trimethoxyquinoline combretastatin analogs were synthesized and evaluated for their potential anticancer activity. The 4-aroylquinoline 11 inhibited the growth of the human cancer cells lines KB, HT-29, and MKN45, as well as the three human resistant cancer [...] Read more.

A series of 2-aroyl and 2-aryl-5,6,7-trimethoxyquinoline and 4-aroyl-6,7,8-trimethoxyquinoline combretastatin analogs were synthesized and evaluated for their potential anticancer activity. The 4-aroylquinoline 11 inhibited the growth of the human cancer cells lines KB, HT-29, and MKN45, as well as the three human resistant cancer cell lines KB-vin10, KB-S15, and KB-7D, with IC₅₀ values of 217, 327, 239, 246, 213, and 252 nM, respectively. Full article

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8 pages, 212 KiB

Open AccessArticle

Antimicrobial Properties of Some Bis(Iminoacenaphthene (BIAN)-Supported N-Heterocyclic Carbene Complexes of Silver and Gold

by Rachel R. Butorac¹, Salem S. Al-Deyab² and Alan H. Cowley^1,*

¹ Department of Chemistry and Biochemistry, University of Texas at Austin, University Station, A5300, Austin, TX 78712, USA

² Chemistry Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia

Molecules 2011, 16(3), 2285-2292; https://doi.org/10.3390/molecules16032285 - 9 Mar 2011

Cited by 37 | Viewed by 8097

Abstract

The AgCl, AgOAc, AuCl, and AuOAc complexes of the new bis(imino)acenaphthene(BIAN)-supported N-heterocyclic carbene ligand and the precursor imidazolium salt have been investigated with respect to their antimicrobial activities against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Psudomonas aeruginosa. The [...] Read more.

The AgCl, AgOAc, AuCl, and AuOAc complexes of the new bis(imino)acenaphthene(BIAN)-supported N-heterocyclic carbene ligand and the precursor imidazolium salt have been investigated with respect to their antimicrobial activities against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Psudomonas aeruginosa. The most active antimicrobial is the precursor imidazolium salt, which has a minimum inhibitory concentration (MIC) value of Full article

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11 pages, 199 KiB

Open AccessArticle

Identification and Determination of Flavonoids in Astragali Radix by High Performance Liquid Chromatography Coupled with DAD and ESI-MS Detection

by Yan-Wen Lv¹, Wei Hu¹, Yu-Ling Wang¹, Lan-Fang Huang^1,*, Yun-Biao He² and Xian-Zhen Xie³

¹ Department of Chemistry and Material Engineering, Quzhou College, Quzhou 324000, China

² Changde Institute for Drug Control, Changde 415000, China

³ Department of Medicine and Pharmacy, Changde Vocational Technical College, Changde 415000, China

Molecules 2011, 16(3), 2293-2303; https://doi.org/10.3390/molecules16032293 - 9 Mar 2011

Cited by 24 | Viewed by 11053

Abstract

A method for the analysis of flavonoids in Astragali Radix by high-performance liquid chromatography (HPLC) combined with photodiode-array detection (DAD) and an electrospray ionization (ESI) - mass spectrometry (MS) was developed. After the samples were extracted with ethanol, the optimum separation conditions for [...] Read more.

A method for the analysis of flavonoids in Astragali Radix by high-performance liquid chromatography (HPLC) combined with photodiode-array detection (DAD) and an electrospray ionization (ESI) - mass spectrometry (MS) was developed. After the samples were extracted with ethanol, the optimum separation conditions for these analytes were achieved using a gradient elution system and a 2.0 × 150 mm Shimadzu VP-ODS column. Eight flavonoids were identified to exist in Astragali Radix based on their characteristic UV data and mass spectra. The concentrations of three major components in this herb—ononin, calycosin and formononetin—were determined by LC/ESI-MS in positive selective ion monitoring (SIM) mode. The calibration curves were linear in the range of 0.9~180.0 μg·mL⁻¹for ononin, 1.8~360.0 μg·mL⁻¹for calycosin and 1.4~280 μg·mL⁻¹ for formononetin, respectively. The limits of quantification (LOQ) and detection (LOD) were 0.9 μg· mL⁻¹and 0.2 μg mL⁻¹for ononin, 1.8 μg mL⁻¹and 0.5 μg·mL⁻¹for calycosin, 1.4 μg mL⁻¹and 0.5 μg·mL⁻¹ for formononetin, respectively. The standard recoveries were between 95.4~104.7%. The developed method was proven to be useful for the quantitative and qualitative analysis of flavonoid constituents in various resources of Astragali Radix. Full article

(This article belongs to the Section Natural Products Chemistry)

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9 pages, 228 KiB

Open AccessArticle

Synthesis and Antimicrobial Evaluation of Some Heterocyclic Chalcone Derivatives

by Nagwa Mohamed Mahrous Hamada¹ and Essam Mohamed Sharshira^2,*

¹ Department of Chemistry, Faculty of Education, Alexandria University, Alexandria, Egypt

² Department of Chemistry, Faculty of Science, Alexandria University, Alexandria, Egypt

Molecules 2011, 16(3), 2304-2312; https://doi.org/10.3390/molecules16032304 - 9 Mar 2011

Cited by 37 | Viewed by 8960

Abstract

Some new heterocyclic compounds containing isoxazole, pyrazole and oxadiazole ring systems were prepared from various chalcones. The synthesized compounds have been characterized by elemental analysis and spectral methods. These compounds were screened for their antimicrobial activities. Full article

(This article belongs to the Special Issue Cycloaddition Reactions in Organic Synthesis)

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10 pages, 438 KiB

Open AccessArticle

Effect of Calcinated Oyster Shell Powder on Growth, Yield, Spawn Run, and Primordial Formation of King Oyster Mushroom (Pleurotus Eryngii)

by Ung-Kyu Choi¹, Ok-Hwan Lee^2,*

and Young-Chan Kim^3,*

¹ School of Nano-Bioscience and Chemical Engineering, Ulsan National Institute of Science and Technology, Ulsan 689, Korea

² Department of Food Science and Biotechnology, Kangwon National University, Chuncheon 200, Korea

³ Institute of Korea Food Research, Seongnam, Kyonggi 463, Korea

Molecules 2011, 16(3), 2313-2322; https://doi.org/10.3390/molecules16032313 - 10 Mar 2011

Cited by 21 | Viewed by 10883

Abstract

This study was conducted to evaluate the calcium (Ca) absorption efficacy of king oyster mushroom (Pleurotus eryngii) grown on sawdust medium supplemented with Ca-sources, including oyster shell powder, and to determine the efficacy of oyster shell powder as a calcium supplement [...] Read more.

This study was conducted to evaluate the calcium (Ca) absorption efficacy of king oyster mushroom (Pleurotus eryngii) grown on sawdust medium supplemented with Ca-sources, including oyster shell powder, and to determine the efficacy of oyster shell powder as a calcium supplement on growth, yield, spawn run and primordial formation of P. eryngii. Optimum calcination of oyster shell powder was achieved at the temperature of 620.56 °C. A 1% supplementation of oyster shell powder in sawdust medium did not suppress the mycelial growth of P. eryngii. Also the supplementation of 2% calcinated oyster shell powder to sawdust medium potentially increased the calcium content up to a level of 315.7 ± 15.7 mg/100 g in the fruiting body of P. eryngii, without extension of duration of spawn run and the retardation of the days to primordial formation. These results suggest that the shellfish by-products, including oyster shell powder, can be utilized to develop calcium enriched king oyster mushrooms. Full article

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11 pages, 277 KiB

Open AccessArticle

An Allelochemical from Myrica gale with Strong Phytotoxic Activity against Highly Invasive Fallopia x bohemica Taxa

by Jean Popovici^1,*,†, Cedric Bertrand²

, Dominique Jacquemoud¹, Floriant Bellvert¹, Maria P. Fernandez¹, Gilles Comte¹ and Florence Piola³

¹ Universite de Lyon, F-69622 Lyon, France, and Universite Lyon 1, Villeurbanne, CNRS, UMR5557, Ecologie Microbienne, 43 Boulevard du 11 Novembre 1918, F-69622 Villeurbanne Cedex, France

² Laboratoire de Chimie des Biomolécules et de l'Environnement, Université de Perpignan, F-66860, Perpignan, France

³ Laboratoire d'Ecologie des Hydrosystèmes Fluviaux, Unité Mixte de Recherche 5023, Centre National de la Recherche Scientifique, Université Lyon 1, 43 Boulevard du 11 Novembre 1918, 69622 Villeurbanne Cedex, France

^† Current address: School of Biological Science, University of Queensland, St. Lucia 4072, QLD, Australia.

Molecules 2011, 16(3), 2323-2333; https://doi.org/10.3390/molecules16032323 - 10 Mar 2011

Cited by 24 | Viewed by 11153

Abstract

We report the identification of the allelochemical 3-(1-oxo-3-phenylpropyl)-1,1,5-trimethylcyclo-hexane-2,4,6-trione, known as myrigalone A, from the fruits and leaves of Myrica gale. The structure of the compound was confirmed by high-resolution techniques (UV, MS and NMR analysis). The compound is phytotoxic towards classical plant [...] Read more.

We report the identification of the allelochemical 3-(1-oxo-3-phenylpropyl)-1,1,5-trimethylcyclo-hexane-2,4,6-trione, known as myrigalone A, from the fruits and leaves of Myrica gale. The structure of the compound was confirmed by high-resolution techniques (UV, MS and NMR analysis). The compound is phytotoxic towards classical plant species used for allelochemical assays and also against Fallopia x bohemica, a highly invasive plant. Application of either powdered dry leaves or dry fruits of M. gale also showed in vitro phytotoxic activity. We hypothesize that M. gale could be used as a green allelopathic shield to control Fallopia x bohemica invasion, in addition to its potential use as an environmentally friendly herbicide. Full article

(This article belongs to the Section Natural Products Chemistry)

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14 pages, 230 KiB

Open AccessArticle

Antioxidant and Antityrosinase Activities of Various Extracts from the Fruiting Bodies of Lentinus lepideus

by Ki Nam Yoon¹, Nuhu Alam¹, Kyung Rim Lee¹, Pyung Gyun Shin², Jong Chun Cheong², Young Bok Yoo² and Tae Soo Lee^1,*

¹ Division of Life Sciences, University of Incheon, Incheon 406-840, Korea

² Mushroom Division, National Institute of Horticultural & Herbal Science, RDA, Suwon 441-707, Korea

Molecules 2011, 16(3), 2334-2347; https://doi.org/10.3390/molecules16032334 - 10 Mar 2011

Cited by 58 | Viewed by 11148

Abstract

Lentinus lepideus is an edible mushroom currently available in Korea. The acetone, methanol and hot water extracts were prepared and assayed for their antioxidant and antityrosinase inhibitory activities. The hot water extract showed the strongest β-carotene-linoleic acid inhibition compared to the other extracts. [...] Read more.

Lentinus lepideus is an edible mushroom currently available in Korea. The acetone, methanol and hot water extracts were prepared and assayed for their antioxidant and antityrosinase inhibitory activities. The hot water extract showed the strongest β-carotene-linoleic acid inhibition compared to the other extracts. At 8 mg/mL, the methanolic extract showed a high reducing power of 1.21. The acetone and methanol extracts were more effective in scavenging DPPH radicals than the hot water extract. The strongest chelating effect was obtained from the methanolic extract. Xanthine oxidase and tyrosinase inhibitory activities of the acetonic, methanol and hot water extracts increased with increasing concentration. Gallic acid, chlorogenic acid, vanillin, naringin, naringenin, formononetin, and biochanin-A were detected in the acetonitrile and hydrochloric acid (5:1) solvent extract. This study suggests that fruiting bodies of L. lepideus can potentially be used as a readily accessible source of natural antioxidants. Full article

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17 pages, 225 KiB

Open AccessReview

Wine and Grape Tannin Interactions with Salivary Proteins and Their Impact on Astringency: A Review of Current Research

by Jacqui M. McRae^1,* and James A. Kennedy²

¹ The Australian Wine Research Institute, PO Box 197, Glen Osmond SA 5064, Australia

² Department of Viticulture and Enology, California State University, 2360 E. Barstow Ave MS VR89, Fresno, CA 93740, USA

Molecules 2011, 16(3), 2348-2364; https://doi.org/10.3390/molecules16032348 - 11 Mar 2011

Cited by 227 | Viewed by 21266

Abstract

Astringency is an important characteristic of red wine quality. The sensation is generally thought to be produced by the interaction of wine tannins with salivary proteins and the subsequent aggregation and precipitation of protein-tannin complexes. The importance of wine astringency for marketability has [...] Read more.

Astringency is an important characteristic of red wine quality. The sensation is generally thought to be produced by the interaction of wine tannins with salivary proteins and the subsequent aggregation and precipitation of protein-tannin complexes. The importance of wine astringency for marketability has led to a wealth of research on the causes of astringency and how tannins impact the quality of the sensation, particularly with respect to tannin structure. Ultimately, the understanding of how tannin structure impacts astringency will allow the controlled manipulation of tannins via such methods as micro-oxygenation or fining to improve the quality of wines. Full article

(This article belongs to the Special Issue Tannins)

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10 pages, 1104 KiB

Open AccessArticle

A-Type Cranberry Proanthocyanidins Inhibit the RANKL-Dependent Differentiation and Function of Human Osteoclasts

by Shinichi Tanabe¹, Juliana Santos¹, Vu Dang La¹, Amy B. Howell² and Daniel Grenier^1,*

¹ Groupe de Recherche en Écologie Buccale, Faculté de Médecine Dentaire, Université Laval, 2420 Rue de La Terrasse, Quebec City, QC, G1V0A6, Canada

² Marucci Center for Blueberry and Cranberry Research, Rutgers, The State University of New Jersey, Chatsworth, NJ 08019, USA

Molecules 2011, 16(3), 2365-2374; https://doi.org/10.3390/molecules16032365 - 11 Mar 2011

Cited by 32 | Viewed by 11737

Abstract

This study investigated the effect of A-type cranberry proanthocyanidins (AC-PACs) on osteoclast formation and bone resorption activity. The differentiation of human pre-osteoclastic cells was assessed by tartrate-resistant acid phosphatase (TRAP) staining, while the secretion of interleukin-8 (IL-8) and matrix metalloproteinases (MMPs) was measured [...] Read more.

This study investigated the effect of A-type cranberry proanthocyanidins (AC-PACs) on osteoclast formation and bone resorption activity. The differentiation of human pre-osteoclastic cells was assessed by tartrate-resistant acid phosphatase (TRAP) staining, while the secretion of interleukin-8 (IL-8) and matrix metalloproteinases (MMPs) was measured by ELISA. Bone resorption activity was investigated by using a human bone plate coupled with an immunoassay that detected the release of collagen helical peptides. AC-PACs up to 100 µg/mL were atoxic for osteoclastic cells. TRAP staining evidenced a dose-dependent inhibition of osteoclastogenesis. More specifically, AC-PACs at 50 µg/mL caused a 95% inhibition of RANKL-dependent osteoclast differentiation. This concentration of AC-PACs also significantly increased the secretion of IL-8 (6-fold) and inhibited the secretion of both MMP-2 and MMP-9. Lastly, AC-PACs (10, 25, 50 and 100 µg/ml) affected bone degradation mediated by mature osteoclasts by significantly decreasing the release of collagen helical peptides. This study suggests that AC-PACs can interfere with osteoclastic cell maturation and physiology as well as prevent bone resorption. These compounds may be considered as therapeutic agents for the prevention and treatment of periodontitis. Full article

(This article belongs to the Special Issue Tannins)

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16 pages, 442 KiB

Open AccessArticle

Cranberry Proanthocyanidins Mediate Growth Arrest of Lung Cancer Cells through Modulation of Gene Expression and Rapid Induction of Apoptosis

by Laura A. Kresty^1,*, Amy B. Howell² and Maureen Baird³

¹ Department of Epidemiology and Public Health, University of Miami Miller School of Medicine and Sylvester Cancer Center, Miami, Florida 33136, USA

² Marucci Center for Blueberry Cranberry Research, Rutgers University, Chatsworth, New Jersey 08019, USA

³ Department of Pathology, The Ohio State University, Columbus, Ohio 43240, USA

Molecules 2011, 16(3), 2375-2390; https://doi.org/10.3390/molecules16032375 - 11 Mar 2011

Cited by 42 | Viewed by 11663

Abstract

Cranberries are rich in bioactive constituents purported to enhance immune function, improve urinary tract health, reduce cardiovascular disease and more recently, inhibit cancer in preclinical models. However, identification of the cranberry constituents with the strongest cancer inhibitory potential and the mechanism associated with [...] Read more.

Cranberries are rich in bioactive constituents purported to enhance immune function, improve urinary tract health, reduce cardiovascular disease and more recently, inhibit cancer in preclinical models. However, identification of the cranberry constituents with the strongest cancer inhibitory potential and the mechanism associated with cancer inhibition by cranberries remains to be elucidated. This study investigated the ability of a proanthocyanidin rich cranberry fraction (PAC) to alter gene expression, induce apoptosis and impact the cell cycle machinery of human NCI-H460 lung cancer cells. Lung cancer is the leading cause of cancer-related deaths in the United States and five year survival rates remain poor at 16%. Thus, assessing potential inhibitors of lung cancer-linked signaling pathways is an active area of investigation. Full article

(This article belongs to the Special Issue Tannins)

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23 pages, 1625 KiB

Open AccessReview

Quantitative Mass Spectrometry for Bacterial Protein Toxins — A Sensitive, Specific, High-Throughput Tool for Detection and Diagnosis

by Anne E. Boyer¹, Maribel Gallegos-Candela¹, Renato C. Lins², Zsuzsanna Kuklenyik¹, Adrian Woolfitt¹, Hercules Moura¹, Suzanne Kalb¹, Conrad P. Quinn³ and John R. Barr^1,*

¹ Centers for Disease Control and Prevention, 4770 Buford Hwy, NE, Atlanta, GA 30341, USA

² Battelle Analytical Services, Atlanta, at the Centers for Disease Control and Prevention, 4770 Buford Hwy, NE, Atlanta, GA 30341, USA

³ Centers for Disease Control and Prevention, 1600 Clifton Rd., Atlanta, GA 30333, USA

Molecules 2011, 16(3), 2391-2413; https://doi.org/10.3390/molecules16032391 - 14 Mar 2011

Cited by 51 | Viewed by 13537

Abstract

Matrix-assisted laser-desorption time-of-flight (MALDI-TOF) mass spectrometry (MS) is a valuable high-throughput tool for peptide analysis. Liquid chromatography electrospray ionization (LC-ESI) tandem-MS provides sensitive and specific quantification of small molecules and peptides. The high analytic power of MS coupled with high-specificity substrates is ideally [...] Read more.

Matrix-assisted laser-desorption time-of-flight (MALDI-TOF) mass spectrometry (MS) is a valuable high-throughput tool for peptide analysis. Liquid chromatography electrospray ionization (LC-ESI) tandem-MS provides sensitive and specific quantification of small molecules and peptides. The high analytic power of MS coupled with high-specificity substrates is ideally suited for detection and quantification of bacterial enzymatic activities. As specific examples of the MS applications in disease diagnosis and select agent detection, we describe recent advances in the analyses of two high profile protein toxin groups, the Bacillus anthracis toxins and the Clostridium botulinum neurotoxins. The two binary toxins produced by B. anthracis consist of protective antigen (PA) which combines with lethal factor (LF) and edema factor (EF), forming lethal toxin and edema toxin respectively. LF is a zinc-dependent endoprotease which hydrolyzes specific proteins involved in inflammation and immunity. EF is an adenylyl cyclase which converts ATP to cyclic-AMP. Toxin-specific enzyme activity for a strategically designed substrate, amplifies reaction products which are detected by MALDI-TOF-MS and LC-ESI-MS/MS. Pre-concentration/purification with toxin specific monoclonal antibodies provides additional specificity. These combined technologies have achieved high specificity, ultrasensitive detection and quantification of the anthrax toxins. We also describe potential applications to diseases of high public health impact, including Clostridium difficile glucosylating toxins and the Bordetella pertussis adenylyl cyclase. Full article

(This article belongs to the Special Issue Toxins - Organic and Analytical Chemistry)

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17 pages, 312 KiB

Open AccessArticle

Investigating Spectrum of Biological Activity of 4- and 5-Chloro-2-hydroxy-N-[2-(arylamino)-1-alkyl-2-oxoethyl]benzamides

by Ales Imramovsky^1,*, Matus Pesko², Katarina Kralova², Marcela Vejsova³, Jirina Stolarikova⁴, Jarmila Vinsova⁵ and Josef Jampilek^6,*

¹ Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentska 573, 532 10 Pardubice, Czech Republic

² Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia

³ Department of Clinical Microbiology, Charles University Medical School and Teaching Hospital, Sokolska 581, Hradec Kralove 500 05, Czech Republic

⁴ Laboratory for Mycobacterial Diagnostics and TB, Institute of Public Health in Ostrava, Partyzanske namesti 7, 702 00 Ostrava, Czech Republic

⁵ Department of Inorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic

⁶ Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 612 42 Brno, Czech Republic

Molecules 2011, 16(3), 2414-2430; https://doi.org/10.3390/molecules16032414 - 14 Mar 2011

Cited by 45 | Viewed by 7732

Abstract

In this study, a series of twenty-two 5-chloro-2-hydroxy-N-[2-(arylamino)-1-alkyl-2-oxoethyl]benzamides and ten 4-chloro-2-hydroxy-N-[2-(arylamino)-1-alkyl-2-oxoethyl]benzamides is described. The compounds were analyzed using RP-HPLC to determine lipophilicity. Primary in vitro screening of the synthesized compounds was performed against mycobacterial, bacterial and fungal strains. They [...] Read more.

In this study, a series of twenty-two 5-chloro-2-hydroxy-N-[2-(arylamino)-1-alkyl-2-oxoethyl]benzamides and ten 4-chloro-2-hydroxy-N-[2-(arylamino)-1-alkyl-2-oxoethyl]benzamides is described. The compounds were analyzed using RP-HPLC to determine lipophilicity. Primary in vitro screening of the synthesized compounds was performed against mycobacterial, bacterial and fungal strains. They were also evaluated for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The compounds showed biological activity comparable with or higher than the standards isoniazid, fluconazole, penicillin G or ciprofloxacin. For all the compounds, the relationships between the lipophilicity and the chemical structure of the studied compounds as well as their structure-activity relationships are discussed. Full article

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12 pages, 161 KiB

Open AccessArticle

Bioflocculant Production by Virgibacillus sp. Rob Isolated from the Bottom Sediment of Algoa Bay in the Eastern Cape, South Africa

by Sekelwa Cosa¹, Leonard V. Mabinya¹, Ademola O. Olaniran², Omobola O. Okoh³, Kim Bernard⁴, Shaun Deyzel⁴ and Anthony I. Okoh^1,*

¹ Applied and Environmental Microbiology Research Group (AEMREG), Department of Biochemistry and Microbiology, University of Fort Hare, Private Bag X1314, Alice 5700, South Africa

² Division of Microbiology, University of KwaZulu Natal, Durban Westville, South Africa

³ Department of Chemistry, University of Fort Hare, Alice, South Africa

⁴ South African Environmental Observation Network, SAEON, Elwandle Node, 18 Somerset Street, Grahamstown, 6140, South Africa

Molecules 2011, 16(3), 2431-2442; https://doi.org/10.3390/molecules16032431 - 14 Mar 2011

Cited by 79 | Viewed by 9627

Abstract

A bioflocculant-producing marine bacterium previously isolated from marine sediment of Algoa Bay was screened for flocculant production. Comparative analysis of 16S rDNA sequence identified the isolate to have 99% similarity to Virgibacillus sp. XQ-1 and it was deposited in the GenBank as Virgibacillus [...] Read more.

A bioflocculant-producing marine bacterium previously isolated from marine sediment of Algoa Bay was screened for flocculant production. Comparative analysis of 16S rDNA sequence identified the isolate to have 99% similarity to Virgibacillus sp. XQ-1 and it was deposited in the GenBank as Virgibacillus sp. Rob with accession number HQ537127. The bacterium produced biflocculants optimally in glucose (70.4%) and peptone (70.4%) as sole sources of carbon and nitrogen, alkaline pH (12) (74%); and the presence of Fe²⁺(74%). Chemical analysis of the bioflocculant revealed it to be a polysaccharide. Full article

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24 pages, 233 KiB

Open AccessReview

Allobetulin and Its Derivatives: Synthesis and Biological Activity

by Wim Dehaen^1,*

, Anastassiya A. Mashentseva^1,2 and Talgat S. Seitembetov³

¹ Molecular Design and Synthesis, Department of Chemistry, University of Leuven, Celestijnenlaan 200F, 3-3001 Leuven, Belgium

² Department of Chemistry, The L.N.Gumilev Eurasian National University, Munaitpasov str. 5, 010008 Astana, Kazakhstan

³ Department of Biochemistry, Medical University “Astana”, Beybetshilyk. 51, 010000 Astana, Kazakhstan

Molecules 2011, 16(3), 2443-2466; https://doi.org/10.3390/molecules16032443 - 14 Mar 2011

Cited by 92 | Viewed by 11671

Abstract

This review covers the chemistry of allobetulin analogs, including their formation by rearrangement from betulin derivatives, their further derivatisation, their fusion with heterocyclic rings, and any further rearrangements of allobetulin compounds including ring opening, ring contraction and ring expansion reactions. In the last [...] Read more.

This review covers the chemistry of allobetulin analogs, including their formation by rearrangement from betulin derivatives, their further derivatisation, their fusion with heterocyclic rings, and any further rearrangements of allobetulin compounds including ring opening, ring contraction and ring expansion reactions. In the last part, the most important biological activities of allobetulin derivatives are listed. One hundred and fifteen references are cited and the relevant literature is covered, starting in 1922 up to the end of 2010. Full article

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19 pages, 1214 KiB

Open AccessReview

Miniproteins as Phage Display-Scaffolds for Clinical Applications

by Frederic Zoller^1,2, Uwe Haberkorn^1,2 and Walter Mier^2,*

¹ Clinical Cooperation Unit Nuclear Medicine, German Cancer Research Center, INF 280, 69120 Heidelberg, Germany

² Department of Nuclear Medicine, University Hospital Heidelberg, INF 400, 69120 Heidelberg, Germany

Molecules 2011, 16(3), 2467-2485; https://doi.org/10.3390/molecules16032467 - 14 Mar 2011

Cited by 29 | Viewed by 10211

Abstract

Miniproteins are currently developed as alternative, non-immunoglobin proteins for the generation of novel binding motifs. Miniproteins are rigid scaffolds that are stabilised by alpha-helices, beta-sheets and disulfide-constrained secondary structural elements. They are tolerant to multiple amino acid substitutions, which allow for the integration [...] Read more.

Miniproteins are currently developed as alternative, non-immunoglobin proteins for the generation of novel binding motifs. Miniproteins are rigid scaffolds that are stabilised by alpha-helices, beta-sheets and disulfide-constrained secondary structural elements. They are tolerant to multiple amino acid substitutions, which allow for the integration of a randomised affinity function into the stably folded framework. These properties classify miniprotein scaffolds as promising tools for lead structure generation using phage display technologies. Owing to their high enzymatic resistance and structural stability, miniproteins are ideal templates to display binding epitopes for medical applications in vivo. This review summarises the characteristics and the engineering of miniproteins as a novel class of scaffolds to generate of alternative binding agents using phage display screening. Moreover, recent developments for therapeutic and especially diagnostic applications of miniproteins are reviewed. Full article

(This article belongs to the Special Issue Phage Display of Combinatorial Libraries)

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15 pages, 2632 KiB

Open AccessArticle

Role of the Morphology and Polyphosphate in Trichoderma harzianum Related to Cadmium Removal

by Adriana De Freitas Lima^1,2, Gabrielle Ferreira de Moura^2,3, Marcos Antonio Barbosa de Lima^2,4, Patrícia Mendes de Souza^2,5, Carlos Alberto Alves da Silva², Galba Maria De Campos Takaki^2,* and Aline Elesbão Do Nascimento²

¹ Master Course in Development of Environmental Processes, Catholic University of Pernambuco, Recife, PE, Brazil

² Nucleus of Research in Environmental Sciences, Catholic University of Pernambuco, 50.050-590 Recife, PE, Brazil

³ Maurício de Nassau Faculty, Recife, PE, Brazil

⁴ Biology Department, Federal Rural University of Pernambuco, Recife, PE, Brazil

⁵ PNPD-CAPES, Catholic University of Pernambuco, Recife, PE, Brazil

Molecules 2011, 16(3), 2486-2500; https://doi.org/10.3390/molecules16032486 - 15 Mar 2011

Cited by 39 | Viewed by 12106

Abstract

This study concerns the metabolism of polyphosphate in Trichoderma harzianum, a biocontrol agent with innate resistance against most chemicals used in agriculture, including metals, when grown in the presence of different concentrations of cadmium. The biomass production was affected by the concentration [...] Read more.

This study concerns the metabolism of polyphosphate in Trichoderma harzianum, a biocontrol agent with innate resistance against most chemicals used in agriculture, including metals, when grown in the presence of different concentrations of cadmium. The biomass production was affected by the concentration of metal used. Control cultures were able to accumulate polyphosphate under the conditions used. Moreover, the presence of cadmium induced a reduction in polyphosphate content related to the concentration used. The morphological/ultrastructural aspects were characterized by using optical and scanning electron microscopy, and were affected by the heavy metal presence and concentration. The efficiency of cadmium removal revealed the potential of the microorganism for use in remediation. The data indicate the potential for polyphosphate accumulation by the fungus, as well as its degradation related to tolerance/survival in the presence of cadmium ions. Full article

(This article belongs to the Section Natural Products Chemistry)

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6 pages, 109 KiB

Open AccessArticle

Fungicidal Properties of the Essential Oil of Hesperozygis marifolia on Aspergillus flavus Link

by Marco Martín González-Chávez¹, Norma Cecilia Cárdenas-Ortega¹, Cristina Andrea Méndez-Ramos¹ and Salud Pérez-Gutiérrez^2,*

¹ Centro de Investigación y Estudios de Posgrado, Facultad de Ciencias Químicas, Universidad Autónoma de San Luis Potosí, Av. Dr. Manuel Nava 6, Zona Universitaria, San Luis Potosí, SLP, 78210, Mexico

² Departamento de Sistemas Biológicos, Universidad Autónoma Metropolitana, A.P. 23-181, México D. F. 11560, Mexico

Molecules 2011, 16(3), 2501-2506; https://doi.org/10.3390/molecules16032501 - 15 Mar 2011

Cited by 13 | Viewed by 8665

Abstract

The chemical composition of the essential oil from Hesperozygis marifolia was analyzed by gas chromatography-mass spectrometry (GC-MS), and fourteen compounds were identified. (R)-pulegone (40.75%), isomenthone (30.34%) and menthone (4.46%) were found to be the main components of the oil. The essential [...] Read more.

The chemical composition of the essential oil from Hesperozygis marifolia was analyzed by gas chromatography-mass spectrometry (GC-MS), and fourteen compounds were identified. (R)-pulegone (40.75%), isomenthone (30.34%) and menthone (4.46%) were found to be the main components of the oil. The essential oil at a concentration of 2.0 mg/mL and (R)-pulegone at concentration of 0.8 mg/mL completely inhibited the growth of Aspergillus flavus Link. The fungicidal effects of this essential oil warrant further research into its potential for commercial use. Full article

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12 pages, 174 KiB

Open AccessArticle

Screening of Natural Organic Volatiles from Prunus mahaleb L. Honey: Coumarin and Vomifoliol as Nonspecific Biomarkers

by Igor Jerković^1,*

, Zvonimir Marijanović² and Mladenka Malenica Staver³

¹ Faculty of Chemistry and Technology, University of Split, N. Tesle 10/V, 21000 Split, Croatia

² Marko Marulić Polytechnic in Knin, P. Krešimira IV 30, 22300 Knin, Croatia

³ Department of Biotechnology, University of Rijeka, S. Krautzeka bb, 51000 Rijeka, Croatia

Molecules 2011, 16(3), 2507-2518; https://doi.org/10.3390/molecules16032507 - 16 Mar 2011

Cited by 39 | Viewed by 8978

Abstract

Headspace solid-phase microextraction (HS-SPME; PDMS/DVB fibre) and ultrasonic solvent extraction (USE; solvent A: pentane and diethyl ether (1:2 v/v), solvent B: dichloromethane) followed by gas chromatography and mass spectrometry (GC, GC-MS) were used for the analysis of Prunus mahaleb L. honey samples. Screening [...] Read more.

Headspace solid-phase microextraction (HS-SPME; PDMS/DVB fibre) and ultrasonic solvent extraction (USE; solvent A: pentane and diethyl ether (1:2 v/v), solvent B: dichloromethane) followed by gas chromatography and mass spectrometry (GC, GC-MS) were used for the analysis of Prunus mahaleb L. honey samples. Screening was focused toward chemical composition of natural organic volatiles to determine if it is useful as a method of determining honey-sourcing. A total of 34 compounds were identified in the headspace and 49 in the extracts that included terpenes, norisoprenoids and benzene derivatives, followed by minor percentages of aliphatic compounds and furan derivatives. High vomifoliol percentages (10.7%–24.2%) in both extracts (dominant in solvent B) and coumarin (0.3%–2.4%) from the extracts (more abundant in solvent A) and headspace (0.9%–1.8%) were considered characteristic for P. mahaleb honey and highlighted as potential nonspecific biomarkers of the honey’s botanical origin. In addition, comparison with P. mahaleb flowers, leaves, bark and wood volatiles from our previous research revealed common compounds among norisoprenoids and benzene derivatives. Full article

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8 pages, 187 KiB

Open AccessArticle

Synthesis and Biological Evaluation of Novel Acenaphthene Derivatives as Potential Antitumor Agents

by Yong-Mei Xie^†, Yi Deng^†, Xiao-Yun Dai, Jie Liu, Liang Ouyang, Yu-Quan Wei^* and Ying-Lan Zhao^*

¹ State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, Chengdu, 610041, China

^† These authors contributed equally to this work.

Molecules 2011, 16(3), 2519-2526; https://doi.org/10.3390/molecules16032519 - 17 Mar 2011

Cited by 17 | Viewed by 8613

Abstract

Twelve novel acenaphthene derivatives have been synthesized. The structures of all compounds were confirmed by ¹H-NMR, MS and elemental analysis. Their antitumor activities were evaluated in six human solid tumor cell lines, namely non-small cell lung cancer (H460), human colon adenocarcinoma (SW480), [...] Read more.

Twelve novel acenaphthene derivatives have been synthesized. The structures of all compounds were confirmed by ¹H-NMR, MS and elemental analysis. Their antitumor activities were evaluated in six human solid tumor cell lines, namely non-small cell lung cancer (H460), human colon adenocarcinoma (SW480), human breast cancer cell (MDA-MB-468 and SKRB-3), human melanoma cell (A375) and human pancreatic cancer (BxPC-3) . Among them, compound 3c shows the best antitumor activity against SKRB-3 cell line, as high as the positive control adriamycin. Full article

(This article belongs to the Section Medicinal Chemistry)

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15 pages, 157 KiB

Open AccessArticle

Antioxidant Bibenzyl Derivatives from Notholaena nivea Desv.

by Giuseppina Cioffi¹, Paola Montoro¹, Olga Lock De Ugaz², Antonio Vassallo³

, Lorella Severino⁴, Cosimo Pizza¹ and Nunziatina De Tommasi^1,*

¹ Dipartimento di Scienze Farmaceutiche e Biomediche, Università degli Studi di Salerno, Via Ponte Don Melillo,1 84084 Fisciano (SA), Italy

² Pontificia Universidad Catolica del Perù, Apartado, 1761, Lima, Peru

³ Dipartimento di Chimica, Università degli Studi della Basilicata, Viale dell’Ateneo Lucano,10 85100 Potenza, Italy

⁴ Dipartimento di Patologia e Sanità Animale, Sez. Tossicologia, Università di Napoli Federico II, Via Del Pino,1 80137, Napoli, Italy

Molecules 2011, 16(3), 2527-2541; https://doi.org/10.3390/molecules16032527 - 17 Mar 2011

Cited by 16 | Viewed by 9733

Abstract

Four new bibenzyl derivatives were isolated, together with other known bibenzyls, by bioassay-guided fractionation of a CHCl₃-MeOH extract of Notholaena nivea Desv. (Pteridaceae) aerial parts. The structures were elucidated by NMR, ESIMS and other spectral analyses. Their antioxidative effects towards superoxide, [...] Read more.

Four new bibenzyl derivatives were isolated, together with other known bibenzyls, by bioassay-guided fractionation of a CHCl₃-MeOH extract of Notholaena nivea Desv. (Pteridaceae) aerial parts. The structures were elucidated by NMR, ESIMS and other spectral analyses. Their antioxidative effects towards superoxide, lipidic peroxidation and the 2,2'-azino-bis-3-ethilbenzothiazoline-6-sulfonic acid (ABTS) radical were assayed. Results showed that the compound 3,12-dihydroxy-5-methoxybibenzyl (6) is the most active compound in the ABTS free-radical scavenging test, while in the coupled oxidation of β-carotene and linoleic acid assay the compound 5,12-dihydroxy-3-methoxydibenzyl-6-carboxylic acid (1) exerted the highest activity after 1h. A superoxide anion enzymatic test was also carried out and the results were confirmed by an inhibition of xanthine oxidase activity assay. The putative protective role played by compounds 1 and 6 on the injurious effects of reactive oxygen metabolites on the intestinal epithelium, using a Caco-2 human cell line, was investigated. H₂O₂-induced alterations were prevented by preincubating the cells with compounds 1 and 6. Full article

(This article belongs to the Section Natural Products Chemistry)

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9 pages, 454 KiB

Open AccessArticle

The Effect of Lycium Barbarum Polysaccharide on Alcohol-Induced Oxidative Stress in Rats

by Daye Cheng^1,* and Hong Kong²

¹ Department of Transfusion, The First Hospital of China Medical University, Shenyang, Liaoning Province, China

² Department of Laboratory Medicine, Shengjing Hospital of China Medical University, Shenyang, Liaoning Province, China

Molecules 2011, 16(3), 2542-2550; https://doi.org/10.3390/molecules16032542 - 17 Mar 2011

Cited by 118 | Viewed by 9764

Abstract

The aim of this study was to investigate the effects of Lycium barbarum Polysaccharide (LBP) on alcohol-induced liver damage in rats. A total of 36 rats were divided into control, ethanol and ethanol + LBP groups. Rats in the ethanol group were fed [...] Read more.

The aim of this study was to investigate the effects of Lycium barbarum Polysaccharide (LBP) on alcohol-induced liver damage in rats. A total of 36 rats were divided into control, ethanol and ethanol + LBP groups. Rats in the ethanol group were fed 7 g ethanol/kg body weight by gastric infusion, three times a day, for 30 consecutive days, while rats in the control group received the same volume of physiological saline instead of ethanol, and rats in ethanol + LBP group were fed both ethanol (7 g/kg body weight) and LBP (300 mg/Kg body weight/day). Alcoholic liver injury was examined by serum ALT and AST activities, alcoholic fatty liver was assessed by lipid levels, and oxidative stress was evaluated by SOD, CAT, GSH-Px, GSH and MDA assays. In the ethanol group, a significant elevation of enzymes and lipid in serum, increased MDA level and depletion of SOD, CAT, GSH-Px and GSH in liver were observed. LBP administration significantly ameliorated liver injury, prevented the progression of alcohol-induced fatty liver, and improved the antioxidant functions when compared with the ethanol group. Histopathological examination of rat liver revealed that LBP administration protected liver cells from the damage induced by ethanol. The results suggest that LBP is a promising agent to protect the liver from hepatotoxicity and fatty liver induced by ethanol intake. Full article

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10 pages, 345 KiB

Open AccessCommunication

LC/MS Guided Isolation of Alkaloids from Lotus Leaves by pH-Zone-Refining Counter-Current Chromatography

by Xia Xu¹, Cui-Rong Sun^1,*, Xiao-Jing Dai¹, Rui-Lin Hu¹, Yuan-Jiang Pan¹ and Zhang-Fa Yang^2,*

¹ Department of Chemistry, Zhejiang University, Hangzhou 310027, China

² Zhejiang Hisoar Pharmaceutical Co., LTD., No.100, Waisha Branch Rd., Jiaojiang District, Taizhou 318000, China

Molecules 2011, 16(3), 2551-2560; https://doi.org/10.3390/molecules16032551 - 18 Mar 2011

Cited by 22 | Viewed by 8361

Abstract

The traditional methods used in natural product separation primarily target the major components and the minor components may thus be lost during the separation procedure. Consequently, it’s necessary to develop efficient methods for the preparative separation and purification of relatively minor bioactive components. [...] Read more.

The traditional methods used in natural product separation primarily target the major components and the minor components may thus be lost during the separation procedure. Consequently, it’s necessary to develop efficient methods for the preparative separation and purification of relatively minor bioactive components. In this paper, a LC/MS method was applied to guide the separation of crude extract of lotus (Nelumbo nucifera Gaertn.) leaves whereby a minor component was identified in the LC/MS analysis. Afterwards, an optimized pH-zone-refining CCC method was performed to isolate this product, identified as N-demethylarmepavine. The separation procedure was carried out with a biphasic solvent system composed of hexane-ethyl acetate-methyl alcohol-water (1:6:1:6, v/v) with triethylamine (10 mM) added to the upper organic phase as a retainer and hydrochloric acid (5 mM) to the aqueous mobile phase eluent. Two structurally similar compounds – nuciferine and roemerine – were also obtained from the crude lotus leaves extract. In total 500 mg of crude extract furnished 7.4 mg of N-demethylarmepavine, 45.3 mg of nuciferine and 26.6 mg of roemerine with purities of 90%, 92% and 96%, respectively. Their structures were further identified by HPLC/ESI-MSⁿ, FTICR/MS and the comparison with reference compounds. Full article

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22 pages, 625 KiB

Open AccessArticle

Purification, Biochemical Characterization, and Bioactive Properties of a Lectin Purified from the Seeds of White Tepary Bean (Phaseolus Acutifolius Variety Latifolius)

by Carmen Valadez-Vega^1,*, Ana María Guzmán-Partida², Francisco Javier Soto-Cordova², Gerardo Álvarez-Manilla³, José A. Morales-González¹

, Eduardo Madrigal-Santillán¹

, José Roberto Villagómez-Ibarra⁴, Clara Zúñiga-Pérez¹, José Gutiérrez-Salinas⁵ and Marco A. Becerril-Flores¹

¹ Institute of Health Sciences, Universidad Autónoma del Estado de Hidalgo, Ex-Hacienda de la Concepción, Tilcuautla, CP 42080 Pachuca de Soto, Hgo, Mexico

² Center for Food Research and Development, A. C. Carretera a la Victoria Km 0.6 C.P. 83304. Hermosillo, Sonora, Mexico

³ Ezose Sciences Inc, Pine Brook, NJ 07058, USA

⁴ Basic Science and Engineering Institute, Universidad Autónoma del Estado de Hidalgo, Carr. A-Pachuca-Tulancingo Km 4.5 Cd Universitaria, CP 42184, Mineral de la Reforma, Hgo, Mexico

⁵ Laboratory of Biochemistry and Experimental Medicine, Division of Biomedical Research, National Medical Center “20 de Noviembre”, ISSSTE, México D.F., Mexico

Molecules 2011, 16(3), 2561-2582; https://doi.org/10.3390/molecules16032561 - 21 Mar 2011

Cited by 16 | Viewed by 12922

Abstract

The present work shows the characterization of Phaseolus acutifolius variety latifolius, on which little research has been published, and provides detailed information on the corresponding lectin. This protein was purified from a semi-domesticated line of white tepary beans from Sonora, Mexico, by precipitation [...] Read more.

The present work shows the characterization of Phaseolus acutifolius variety latifolius, on which little research has been published, and provides detailed information on the corresponding lectin. This protein was purified from a semi-domesticated line of white tepary beans from Sonora, Mexico, by precipitation of the aqueous extract with ammonium sulfate, followed by affinity chromatography on an immobilized fetuin matrix. MALDI TOF analysis of Phaseolus acutifolius agglutinin (PAA) showed that this lectin is composed of monomers with molecular weights ranging between 28 and 31 kDa. At high salt concentrations, PAA forms a dimer of 63 kDa, but at low salt concentrations, the subunits form a tetramer. Analysis of PAA on 2D-PAGE showed that there are mainly three types of subunits with isoelectric points of 4.2, 4.4, and 4.5. The partial sequence obtained by LC/MS/MS of tryptic fragments from the PAA subunits showed 90–100% identity with subunits from genus Phaseolus lectins in previous reports. The tepary bean lectin showed lower hemagglutination activity than Phaseolus vulgaris hemagglutinin (PHA-E) toward trypsinized human A and O type erythrocytes. The hemagglutination activity was inhibited by N-glycans from glycoproteins. Affinity chromatography with the immobilized PAA showed a high affinity to glycopeptides from thyroglobulin, which also has N-glycans with a high content of N-acetylglucosamine. PAA showed less mitogenic activity toward human lymphocytes than PHA-L and Con A. The cytotoxicity of PAA was determined by employing three clones of the 3T3 cell line, demonstrating variability among the clones as follows: T4 (DI₅₀ 51.5 µg/mL); J20 (DI₅₀ 275 µg/mL), and N5 (DI₅₀72.5 µg/mL). Full article

(This article belongs to the Section Molecular Diversity)

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16 pages, 1490 KiB

Open AccessArticle

Panduratin A Inhibits the Growth of A549 Cells through Induction of Apoptosis and Inhibition of NF-KappaB Translocation

by Shiau-Chuen Cheah^1,*, David R. Appleton^1,2, Sui-Ting Lee¹, May-Lynn Lam³, A. Hamid A. Hadi⁴ and Mohd. Rais Mustafa¹

¹ Centre of Natural Products & Drug Discovery (CENAR), Department of Pharmacology, Faculty of Medicine, University of Malaya, 50603 Kuala Lumpur, Malaysia

² Sime Darby Technology Centre, 1st Floor, Block B, UPM-MTDC Technology Centre III, UPM, Serdang 43400, Selangor, Malaysia

³ Cancer Research Initiatives Foundation (CARIF), 2nd Floor, Outpatient Centre, Sime Darby Medical Centre, 47500 Subang Jaya, Selangor Darul Ehsan, Malaysia

⁴ Centre of Natural Products & Drug Discovery (CENAR), Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia

Molecules 2011, 16(3), 2583-2598; https://doi.org/10.3390/molecules16032583 - 21 Mar 2011

Cited by 69 | Viewed by 17468

Abstract

In the present study we investigated the effects of panduratin A, isolated from Boesenbergia rotunda, on proliferation and apoptosis in A549 human non-small cell lung cancer cells. Cell proliferation and induction of apoptosis was determined by the real-time cellular analyzer (RTCA), MTT [...] Read more.

In the present study we investigated the effects of panduratin A, isolated from Boesenbergia rotunda, on proliferation and apoptosis in A549 human non-small cell lung cancer cells. Cell proliferation and induction of apoptosis was determined by the real-time cellular analyzer (RTCA), MTT assay and High Content Screening (HCS). The RTCA assay indicated that panduratin A exhibited cytotoxicity, with an IC₅₀ value of 4.4 µg/mL (10.8 µM). Panduratin A arrested cancer cells labeled with bromodeoxyuridine (BrdU) and phospho-Histone H3 in the mitotic phase. The cytotoxic effects of panduratin A were found to be accompanied by a dose-dependent induction of apoptosis, as assessed by DNA condensation, nuclear morphology and intensity, cell permeability, mitochondrial mass/ potential, F-actin and cytochrome c. In addition, treatment with an apoptosis-inducing concentration of panduratin A resulted in significant inhibition of Nuclear Factor-kappa Beta (NF-κB) translocation from cytoplasm to nuclei activated by tumor necrosis factor-alpha (TNF-α), as illustrated by the HCS assay. Our study provides evidence for cell growth inhibition and induction of apoptosis by panduratin A in the A549 cell line, suggesting its therapeutic potential as an NF-κB inhibitor. Full article

(This article belongs to the Section Natural Products Chemistry)

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10 pages, 353 KiB

Open AccessArticle

Studies on the Genetic Variation of the Green Unicellular Alga Haematococcus pluvialis (Chlorophyceae) Obtained from Different Geographical Locations Using ISSR and RAPD Molecular Marker

by Noroozi Mostafa^1,2, Hishamuddin Omar¹, Soon Guan Tan³ and Suhaimi Napis^3,*

¹ Department of Biology, Faculty of Science, University Putra Malaysia, 43400 Serdang, Selangor, Malaysia

² Department of Biology Faculty of Science, Alzahra University, Tehran 1993891176, Iran

³ Department of Cell and Molecular Biology, Faculty of Biotechnology and Biomolecular Science, University Putra Malaysia, 43400 Serdang, Selangor, Malaysia

Molecules 2011, 16(3), 2599-2608; https://doi.org/10.3390/molecules16032599 - 22 Mar 2011

Cited by 19 | Viewed by 8016

Abstract

Haematococcus pluvialis (Flotow) is a unicellular green alga, which is considered to be the best astaxanthin-producing organism. Molecular markers are suitable tools for the purpose of finding out genetic variations in organisms; however there have been no studies conducted on ISSR or RAPD [...] Read more.

Haematococcus pluvialis (Flotow) is a unicellular green alga, which is considered to be the best astaxanthin-producing organism. Molecular markers are suitable tools for the purpose of finding out genetic variations in organisms; however there have been no studies conducted on ISSR or RAPD molecular markers for this organism. The DNA of 10 different strains of H. pluvialis (four strains from Iran, two strains from Finland, one strain from Switzerland and three strains from the USA) was extracted. A genetic similarity study was carried out using 14 ISSR and 12 RAPD primers. Moreover, the molecular weights of the bands produced ranged from 0.14 to 3.4 Kb. The PCA and dendrogram clustered the H. pluvialis strains into various groups according to their geographical origin. The lowest genetic similarity was between the Iran2 and USA2 strains (0.08) and the highest genetic similarity was between Finland1 and Finland2 (0.64). The maximum numbers of bands produced by the ISSR and RAPD primers were 35 and 6 bands, respectively. The results showed that ISSR and RAPD markers are useful for genetic diversity studies of Haematococcus as they showed geographical discrimination. Full article

(This article belongs to the Section Molecular Diversity)

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17 pages, 913 KiB

Open AccessArticle

Chemical Composition and In Vitro Activity of Plant Extracts from Ferula communis and Dittrichia viscosa against Postharvest Fungi

by Erjon Mamoci^1,2, Ivana Cavoski^2,*, Vito Simeone², Donato Mondelli³, Lina Al-Bitar² and Pierluigi Caboni⁴

¹ Dipartimento di Science per l'Ambiente, Università degli Studi di Napoli "Parthenope" Centro Direzionale, Isola C4, 80143 Napoli, Italy

² Istituto Agronomico Mediterraneo di Bari,Via Ceglie 9, 70010 Valenzano, Italy

³ Dipartimento di Biologia e Chimica Agro-Forestale ed Ambientale, Università degli Studi di Bari, Via Amendola 165/A, 70126 Bari, Italy

⁴ Dipartimento di Tossicologia, Università degli Studi di Cagliari, Via Ospedale 72, 09124 Cagliari, Italy

Molecules 2011, 16(3), 2609-2625; https://doi.org/10.3390/molecules16032609 - 22 Mar 2011

Cited by 46 | Viewed by 12127

Abstract

F. communis and D. viscosa are perennial Mediterranean weeds that have been used for different therapeutic purposes in traditional pharmacopeia. Plant extracts were obtained from air dried D. viscosa young shoots (DvA) and F. communis aerial part (FcA) and roots (FcR) with n [...] Read more.

F. communis and D. viscosa are perennial Mediterranean weeds that have been used for different therapeutic purposes in traditional pharmacopeia. Plant extracts were obtained from air dried D. viscosa young shoots (DvA) and F. communis aerial part (FcA) and roots (FcR) with n-hexane. The chemical compositions of the extracts were analyzed by HPLC-DAD, LC-MS (ESI) and LC-Q-TOF techniques. Two sesquiterpene lactones (inuviscolide, tomentosin) and three sesquiterpene acids (costic acid, hydroxycostic acid, ilicic acid) were identified from the D. viscosa extract, while in F. communis extracts three daucane sesquiterpenes (acetoxyferutinin, oxojaeskeanadioyl anisate, fertidin) and one coumarin (ferulenol) derivates were found. Biological activities of plant extracts were studied in in vitro experiments on the colonies and conidia of Botryotinia fuckeliana, Penicillium digitatum, P. expansum, Monilinia laxa, M. fructigena and Aspergillus spp. Extracts showed varying degree of antifungal activities on colony growth and conidia germination. The extract from FcA showed the least effect, while DvA extract had the strongest fungitoxic effects. FcR extract presented a fungitoxic effect on the colony growth, but it was not able to inhibit the conidia germination. These distinctions can be attributed to the differences in chemical composition of plant extracts. Full article

(This article belongs to the Section Natural Products Chemistry)

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10 pages, 189 KiB

Open AccessArticle

Synthesis and In Vitro Antibacterial Activity of 7-(3-Amino-6,7-dihydro-2-methyl-2H-pyrazolo[4,3-c] Pyridin-5(4H)-yl)fluoroquinolone Derivatives

by Xin Guo^1,2, Ming Liang Liu¹, Hui Yuan Guo¹, Yu Cheng Wang¹ and Ju Xian Wang^1,*

¹ Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

² College of Pharmaceutical Sciences, Southwest University, Chongqing 400715, China

Molecules 2011, 16(3), 2626-2635; https://doi.org/10.3390/molecules16032626 - 22 Mar 2011

Cited by 17 | Viewed by 8223

Abstract

A series of novel 7-(3-amino-6,7-dihydro-2-methyl-2H-pyrazolo[4,3-c]pyridin- 5(4H)-yl)fluoroquinolone derivatives were designed, synthesized and characterized by ¹H-NMR, MS and HRMS. These fluoroquinolones were evaluated for their in vitro antibacterial activity against representative Gram-positive and Gram-negative strains. Results reveal that most of [...] Read more.

A series of novel 7-(3-amino-6,7-dihydro-2-methyl-2H-pyrazolo[4,3-c]pyridin- 5(4H)-yl)fluoroquinolone derivatives were designed, synthesized and characterized by ¹H-NMR, MS and HRMS. These fluoroquinolones were evaluated for their in vitro antibacterial activity against representative Gram-positive and Gram-negative strains. Results reveal that most of the target compounds exhibit good growth inhibitory potency against methicillin-resistant Staphylococcus epidermidis (MRSE) (MIC: 0.25–4 μg/mL) and Streptococcus pneumoniae (MIC: 0.25–1 μg/mL). In addition, compound 8f is 8–128 fold more potent than the reference drugs gemifloxacin (GM), moxifloxacin (MX), ciprofloxacin (CP) and levofloxacin (LV) against methicillin-resistant Staphylococcus aureus 10-05 and Streptococcus hemolyticus 1002 and 2–64 fold more active against methicillin-sensitive Staphylococcus aureus 10-03 and 10-04. Full article

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10 pages, 209 KiB

Open AccessArticle

Immunosuppressive Activity of 8-Gingerol on Immune Responses in Mice

by Jing Lu^1,2,†, Shuang Guan^1,†, Xue Shen², Wenhui Qian², Guoren Huang², Xuming Deng^1,* and Guanghong Xie^1,*

¹ Department of Veterinary Pharmacology, College of Animal Science and Veterinary Medicine, Jilin University, Changchun, Jilin 130062, China

² Laboratory of Nutrition and Function Food, Jilin University, Changchun, Jilin 130062, China

^† These authors should be regarded as joint first author.

Molecules 2011, 16(3), 2636-2645; https://doi.org/10.3390/molecules16032636 - 22 Mar 2011

Cited by 38 | Viewed by 9234

Abstract

8-Gingerol is one of the principal components of ginger, which is widely used in China and elsewhere as a food, spice and herb. It shows immunosuppressive activity on the immune responses to ovalbumin (OVA) in mice. In the present study, we found that [...] Read more.

8-Gingerol is one of the principal components of ginger, which is widely used in China and elsewhere as a food, spice and herb. It shows immunosuppressive activity on the immune responses to ovalbumin (OVA) in mice. In the present study, we found that 8-gingerol suppressed lipopolysaccharide (LPS) and concanavalin A (ConA)-stimulated splenocyte proliferation in vitro. In vivo, 8-gingerol not only signiﬁcantly suppressed Con A-, LPS- and OVA-induced splenocyte proliferation (P < 0.05) but also decreased the percentage of CD19⁺B cells and CD3⁺ T cell (P < 0.05) at high doses (50, 100 mg/kg). Moreover, OVA-speciﬁc IgG, IgG1 and IgG2b levels in OVA-immunized mice were reduced by 8-gingerol at doses of 50, 100 mg/kg. These results suggest that 8-gingerol could suppress humoral and cellular immune responses in mice. The mechanism might be related to direct inhibition of sensitized T and B lymphocytes. Full article

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11 pages, 178 KiB

Open AccessArticle

Inter-Population Variability of Terpenoid Composition in Leaves of Pistacia lentiscus L. from Algeria: A Chemoecological Approach

by Samir Ait Said^1,2, Catherine Fernandez², Stéphane Greff², Franck Torre³, Arezki Derridj¹, Thierry Gauquelin² and Jean-Philippe Mevy^2,*

¹ Faculté des Sciences Biologiques et des Sciences Agronomiques, Université Mouloud MAMMERI BP 17 Tizi-Ouzou, Algeria

² Institut Méditerranéen d’Ecologie et Paléoécologie (IMEP), UMR CNRS 6116, Equipe Diversité Fonctionnelle des Communautés Végétales, Aix-Marseille Université, Centre Saint Charles. 3, place Victor Hugo. 13331, Marseille Cedex 3, France

³ Institut Méditerranéen d’Ecologie et Paléoécologie (IMEP), UMR CNRS 6116, Equipe Population, Communauté, Paysage. case 461, 13397, Aix-Marseille Université, Marseille Cedex 20, France

Molecules 2011, 16(3), 2646-2657; https://doi.org/10.3390/molecules16032646 - 22 Mar 2011

Cited by 24 | Viewed by 8818

Abstract

Three different altitudes were selected to study the variability of terpenoid composition from leaves of female plants of Pistacia lentiscus L. throughout the elevation gradient. GC-MS analyses showed that terpenoid contents change with altitude. Forty nine compounds were identified with a high interpopulation [...] Read more.

Three different altitudes were selected to study the variability of terpenoid composition from leaves of female plants of Pistacia lentiscus L. throughout the elevation gradient. GC-MS analyses showed that terpenoid contents change with altitude. Forty nine compounds were identified with a high interpopulation variability for low- and midaltitude sites that also exhibited the same major components when data were expressed on dry weight basis. However, Two-Way-ANOVA followed by Tukey’s post hoc test showed that monoterpene hydrocarbons increased with elevation, giving values of 21.7, 37.5 and 221.5 µg g⁻¹ dw for low- mid- and highlands, respectively. On the other hand, applying P.C.A. with data expressed in percentage of the chromatogram of the volatile extract led to the identification of three chemotypes associated with altitudinal levels. In highlands (Group I), the major compounds were b-caryophyllene (12%), δ-cadinene (9.3%) and a-pinene (6.3%) while in midlands (Group II), b-caryophyllene (11.5%), δ-cadinene (8.6%) and caryophyllene oxide (6.8%) were the main components. In lowlands (Group III) δ-cadinene (10.9%), cubebol (10.5%) and β-bisabolene (7.7%) were chiefly present. Hence, the involvement of genetic factors, temperature and drought in the chemical polymorphism of P. lentiscus associated with elevation is discussed in this report. Full article

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14 pages, 370 KiB

Open AccessArticle

Investigation of Solvolysis Kinetics of New Synthesized Fluocinolone Acetonide C-21 Esters—An In Vitro Model for Prodrug Activation

by Bojan D. Markovic^1,*, Vladimir D. Dobricic¹, Sote M. Vladimirov¹, Olivera A. Cudina¹, Vladimir M. Savic² and Katarina D. Karljikovic-Rajic³

¹ Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11221 Belgrade, Serbia

² Department of Organic Chemistry, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11221 Belgrade, Serbia

³ Department of Analytical Chemistry, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11221 Belgrade, Serbia

Molecules 2011, 16(3), 2658-2671; https://doi.org/10.3390/molecules16032658 - 23 Mar 2011

Cited by 11 | Viewed by 10783

Abstract

In this study the solvolysis of newly synthesized fluocinolone acetonide C-21 esters was analysed in comparison with fluocinonide during a 24-hour period of time. The solvolysis was performed in an ethanol-water (90:10 v/v) mixture using the excess of NaHCO₃. The solvolytic [...] Read more.

In this study the solvolysis of newly synthesized fluocinolone acetonide C-21 esters was analysed in comparison with fluocinonide during a 24-hour period of time. The solvolysis was performed in an ethanol-water (90:10 v/v) mixture using the excess of NaHCO₃. The solvolytic mixtures of each investigated ester have been assayed by a RP-HPLC method using isocratic elution with methanol-water (75:25 v/v); flow rate 1 mL/min; detection at 238 nm; temperature 25 °C. Solvolytic rate constants were calculated from the obtained data. Geometry optimizations and charges calculations were carried out by Gaussian W03 software. A good correlation (R = 0.9924) was obtained between solvolytic rate constants and the polarity of the C-O2 bond of those esters. The established relation between solvolytic rate constant (K) and lipophilicity (cLogP) with experimental anti-inflammatory activity could be indicative for topical corticosteroid prodrug activation. Full article

(This article belongs to the Special Issue Prodrugs)

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16 pages, 701 KiB

Open AccessReview

Challenges and Perspectives of Chemical Biology, a Successful Multidisciplinary Field of Natural Sciences

by Fernando A. Rojas-Ruiz¹, Leonor Y. Vargas-Méndez² and Vladimir V. Kouznetsov^1,*

¹ Laboratorio de Química Orgánica y Biomolecular, Facultad de Ciencias, Universidad Industrial de Santander, Bucaramanga, Colombia

² Grupo de Investigaciones Ambientales, Facultad de Química Ambiental, Universidad Santo Tomás, A. A. 1076, Bucaramanga, Colombia

Molecules 2011, 16(3), 2672-2687; https://doi.org/10.3390/molecules16032672 - 23 Mar 2011

Cited by 6 | Viewed by 13101

Abstract

Objects, goals, and main methods as well as perspectives of chemical biology are discussed. This review is focused on the fundamental aspects of this emerging field of life sciences: chemical space, the small molecule library and chemical sensibilization (small molecule microassays). Full article

(This article belongs to the Special Issue Diversity Oriented Synthesis)

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26 pages, 487 KiB

Open AccessReview

Glycosides, Depression and Suicidal Behaviour: The Role of Glycoside-Linked Proteins

by Gianluca Serafini^1,2,*, Maurizio Pompili^1,2,3, Marco Innamorati¹, Gloria Giordano¹, Roberto Tatarelli¹, David Lester⁴, Paolo Girardi^1,2 and Yogesh Dwivedi⁵

¹ Department of Neuroscience, Mental Health and Sensory Functions, “Sapienza” University of Rome, Suicide Prevention Center, Sant’Andrea Hospital, Via Grottarossa 1035-1039, 00189 Rome, Italy

² Villa Rosa, Scientific Medical Research Center, Suore Hospitaliere of the Sacred Heart of Jesus, 01100 Viterbo, Italy

³ McLean Hospital, Harvard Medical School, Boston, MA 02478, USA

⁴ The Richard Stockton College of New Jersey, Jimmie Leeds Road, Pomona, NJ 08240, USA

⁵ Department of Psychiatry, Psychiatric Institute, College of Medicine, University of Illinois at Chicago, Chicago, IL 60612, USA

Molecules 2011, 16(3), 2688-2713; https://doi.org/10.3390/molecules16032688 - 23 Mar 2011

Cited by 13 | Viewed by 10794

Abstract

Nowadays depression and suicide are two of the most important worldwide public health problems. Although their specific molecular mechanisms are still largely unknown, glycosides can play a fundamental role in their pathogenesis. These molecules act presumably through the up-regulation of plasticity-related proteins: probably [...] Read more.

Nowadays depression and suicide are two of the most important worldwide public health problems. Although their specific molecular mechanisms are still largely unknown, glycosides can play a fundamental role in their pathogenesis. These molecules act presumably through the up-regulation of plasticity-related proteins: probably they can have a presynaptic facilitatory effect, through the activation of several intracellular signaling pathways that include molecules like protein kinase A, Rap-1, cAMP, cADPR and G proteins. These proteins take part in a myriad of brain functions such as cell survival and synaptic plasticity. In depressed suicide victims, it has been found that their activity is strongly decreased, primarily in hippocampus and prefrontal cortex. These studies suggest that glycosides can regulate neuroprotection through Rap-1 and other molecules, and may play a crucial role in the pathophysiology of depression and suicide. Full article

(This article belongs to the Special Issue Glycosides)

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12 pages, 294 KiB

Open AccessArticle

Oxidative Decarboxylation of Levulinic Acid by Silver(I)/Persulfate

by Yan Gong and Lu Lin^*

Department of Resources Science and Engineering, State Key Lab of Pulp and Paper Engineering, South China University of Technology, Guangzhou 510640, China

Molecules 2011, 16(3), 2714-2725; https://doi.org/10.3390/molecules16032714 - 23 Mar 2011

Cited by 39 | Viewed by 10533

Abstract

The oxidative decarboxylation of levulinic acid (LA) by silver(I)/persulfate [Ag(I)/S₂O₈²⁻] has been investigated in this paper. The effects of buffer solution, initial pH value, time and temperature and dosages of Ag(I)/S₂O₈²⁻ on the decarboxylation [...] Read more.

The oxidative decarboxylation of levulinic acid (LA) by silver(I)/persulfate [Ag(I)/S₂O₈²⁻] has been investigated in this paper. The effects of buffer solution, initial pH value, time and temperature and dosages of Ag(I)/S₂O₈²⁻ on the decarboxylation of LA were examined in batch experiments and a reaction scheme was proposed on basis of the reaction process. The experimental results showed that a solution of NaOH-KH₂PO₄was comparatively suitable for the LA decarboxylation reaction by silver(I)/persulfate. Under optimum conditions (temperature 160 °C, pH 5.0, and time 0.5 h), the rate of LA conversion in NaOH-KH₂PO₄solutions with an initial concentration of 0.01 mol LA reached 70.2%, 2-butanone (methyl ethyl ketone) was the single product in the gas phase and the resulted molar yield reached 44.2%. Full article

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