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Molecules, Volume 20, Issue 12 (December 2015)

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Open AccessCommunication Guignardones P–S, New Meroterpenoids from the Endophytic Fungus Guignardia mangiferae A348 Derived from the Medicinal Plant Smilax glabra
Molecules 2015, 20(12), 22900-22907; https://doi.org/10.3390/molecules201219890
Received: 23 November 2015 / Revised: 15 December 2015 / Accepted: 17 December 2015 / Published: 21 December 2015
Cited by 11 | Viewed by 2030 | PDF Full-text (3618 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Four new meroterpenoids, guignardones P–S (14), and three known analogues (57) were isolated from the endophytic fungal strain Guignardia mangiferae A348. Their structures were elucidated on the basis of spectroscopic analysis and single crystal X-ray
[...] Read more.
Four new meroterpenoids, guignardones P–S (14), and three known analogues (57) were isolated from the endophytic fungal strain Guignardia mangiferae A348. Their structures were elucidated on the basis of spectroscopic analysis and single crystal X-ray diffraction. All the isolated compounds were evaluated for their inhibitory effects on SF-268, MCF-7, and NCI-H460 human cancer cell lines. Compounds 2 and 4 exhibited weak inhibitions of cell proliferation against MCF-7 cell line. Full article
(This article belongs to the collection Bioactive Compounds)
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Open AccessArticle Cross-Coupling Synthesis of Methylallyl Alkenes: Scope Extension and Mechanistic Study
Molecules 2015, 20(12), 22890-22899; https://doi.org/10.3390/molecules201219886
Received: 20 November 2015 / Revised: 9 December 2015 / Accepted: 14 December 2015 / Published: 21 December 2015
Cited by 6 | Viewed by 1550 | PDF Full-text (5257 KB) | HTML Full-text | XML Full-text
Abstract
Cross-coupling reactions between 2-methyl-2-propen-1-ol and various boronic acids are used to obtain aromatic-(2-methylallyl) derivatives. However, deboronation or isomerization side reactions may occur for several boronic acids. We describe herein the synthesis of original alkenes with good yields under mild reaction conditions that decrease
[...] Read more.
Cross-coupling reactions between 2-methyl-2-propen-1-ol and various boronic acids are used to obtain aromatic-(2-methylallyl) derivatives. However, deboronation or isomerization side reactions may occur for several boronic acids. We describe herein the synthesis of original alkenes with good yields under mild reaction conditions that decrease these side reactions. The scope of this environmentally benign reaction is thereby extended to a wide variety of boronic acids. A mechanistic study was conducted and suggested a plausible catalytic cycle mechanism, pointing to the importance of the Lewis acidity of the boronic acid used. Full article
(This article belongs to the Section Organic Chemistry)
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Open AccessArticle The Sensitivity of Endodontic Enterococcus spp. Strains to Geranium Essential Oil
Molecules 2015, 20(12), 22881-22889; https://doi.org/10.3390/molecules201219888
Received: 18 September 2015 / Revised: 7 December 2015 / Accepted: 14 December 2015 / Published: 21 December 2015
Cited by 1 | Viewed by 1745 | PDF Full-text (199 KB) | HTML Full-text | XML Full-text
Abstract
Enterococci are able to survive endodontic procedures and contribute to the failure of endodontic therapy. Thus, it is essential to identify novel ways of eradicating them from infected root canals. One such approach may be the use of antimicrobials such as plant essential
[...] Read more.
Enterococci are able to survive endodontic procedures and contribute to the failure of endodontic therapy. Thus, it is essential to identify novel ways of eradicating them from infected root canals. One such approach may be the use of antimicrobials such as plant essential oils. Enterococcal strains were isolated from endodontically treated teeth by standard microbiological methods. Susceptibility to antibiotics was evaluated by the disc-diffusion method. The minimal inhibitory concentration (MIC) of geranium essential oil was investigated by microdilution in 96-well microplates in Mueller Hinton Broth II. Biofilm eradication concentrations were checked in dentin tests. Geranium essential oil inhibited enterococcal strains at concentrations ranging from 1.8–4.5 mg/mL. No correlation was shown between resistance to antibiotics and the MICs of the test antimicrobials. The MICs of the test oil were lower than those found to show cytotoxic effects on the HMEC-1 cell line. Geranium essential oil eradicated enterococcal biofilm at concentrations of 150 mg/mL. Geranium essential oil inhibits the growth of endodontic enterococcal species at lower concentrations than those required to reach IC50 against the HMEC-1 cell line, and is effective against bacteria protected in biofilm at higher concentrations. In addition, bacteria do not develop resistance to essential oils. Hence, geranium essential oil represents a possible alternative to other antimicrobials during endodontic procedures. Full article
(This article belongs to the Section Natural Products Chemistry)
Open AccessCommunication Fatty Acid Profile and Biological Activities of Linseed and Rapeseed Oils
Molecules 2015, 20(12), 22872-22880; https://doi.org/10.3390/molecules201219887
Received: 2 November 2015 / Revised: 13 December 2015 / Accepted: 16 December 2015 / Published: 21 December 2015
Cited by 12 | Viewed by 2194 | PDF Full-text (907 KB) | HTML Full-text | XML Full-text
Abstract
It has been postulated that fatty acids found in edible oils may exert beneficial health effects by the modulation of signaling pathways regulating cell differentiation and proliferation, especially in the treatment of cardiovascular diseases. In the present study, the biological effects of selected
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It has been postulated that fatty acids found in edible oils may exert beneficial health effects by the modulation of signaling pathways regulating cell differentiation and proliferation, especially in the treatment of cardiovascular diseases. In the present study, the biological effects of selected edible oils—linseed (LO) and rapeseed (RO) oils—were tested in vitro on fibroblast cells. The fatty acid profile of the oils was determined using gas chromatography and FTIR spectroscopy. LO was found to be rich in α-linolenic acid (ALA), whereas oleic acid was the most abundant species in RO. Fatty acids were taken up by the cells and promoted cell proliferation. No oxidative stress-mediated cytotoxic or genotoxic effects were observed after oil stimulation. Oils ameliorated the process of wound healing as judged by improved migration of fibroblasts to the wounding area. As ALA-rich LO exhibited the most potent wound healing activity, ALA may be considered a candidate for promoting the observed effect. Full article
(This article belongs to the collection Bioactive Compounds)
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Open AccessArticle Bioactive Properties of Tabebuia impetiginosa-Based Phytopreparations and Phytoformulations: A Comparison between Extracts and Dietary Supplements
Molecules 2015, 20(12), 22863-22871; https://doi.org/10.3390/molecules201219885
Received: 12 November 2015 / Revised: 15 December 2015 / Accepted: 17 December 2015 / Published: 21 December 2015
Cited by 2 | Viewed by 2083 | PDF Full-text (207 KB) | HTML Full-text | XML Full-text
Abstract
Tabebuia impetiginosa (Mart. ex DC.) Standl. has been used in traditional medicine for many centuries, being nowadays marketed as dried plant material (inner bark) for infusions, pills, and syrups. The main objective of the present work was to validate its popular use through
[...] Read more.
Tabebuia impetiginosa (Mart. ex DC.) Standl. has been used in traditional medicine for many centuries, being nowadays marketed as dried plant material (inner bark) for infusions, pills, and syrups. The main objective of the present work was to validate its popular use through the bioactivity evaluation of the inner bark (methanolic extract and infusion) and of two different formulations (pills and syrup) also based on the same plant-material. The antioxidant activity was evaluated by in vitro assays testing free radical scavenging activity, reducing power and inhibition of lipid peroxidation in brain homogenates. The cytotoxicity was determined in four human tumor cell lines (MCF-7, NCI-H460, HeLa and HepG2, and also in non-tumor cells (porcine liver primary cells, PLP2)). Furthermore, the sample was chemically characterized regarding free sugars, organic acids, fatty acids, and tocopherols. Syrup and methanolic extract showed the highest antioxidant activity, related to their highest amount of phenolics and flavonoids. Methanolic extract was the only sample showing cytotoxic effects on the tested human tumor cell lines, but none of the samples showed toxicity in PLP2. Glucose and oxalic acid were, respectively, the most abundant sugar and organic acid in the sample. Unsaturated predominated over the saturated fatty acids, due to oleic, linoleic, and linolenic acids expression. α- and γ-Tocopherols were also identified and quantified. Overall, T. impetiginosa might be used in different phytoformulations, taking advantage of its interesting bioactive properties and chemical composition. Full article
(This article belongs to the collection Bioactive Compounds)
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Open AccessArticle Ellagitannins and Flavan-3-ols from Raspberry Pomace Modulate Caecal Fermentation Processes and Plasma Lipid Parameters in Rats
Molecules 2015, 20(12), 22848-22862; https://doi.org/10.3390/molecules201219878
Received: 5 October 2015 / Revised: 25 November 2015 / Accepted: 14 December 2015 / Published: 21 December 2015
Cited by 6 | Viewed by 1847 | PDF Full-text (478 KB) | HTML Full-text | XML Full-text
Abstract
Raspberry pomace is a source of polyphenols, which nutritional and health promoting properties are not sufficiently known. The aim of this 8-weeks study was to scrutinize if raspberry extracts (REs) with different ellagitannins to flavan-3-ols ratios might favorably affect the caecal fermentation processes
[...] Read more.
Raspberry pomace is a source of polyphenols, which nutritional and health promoting properties are not sufficiently known. The aim of this 8-weeks study was to scrutinize if raspberry extracts (REs) with different ellagitannins to flavan-3-ols ratios might favorably affect the caecal fermentation processes and blood lipid profile in rats. Forty male Wistar rats were fed with a standard diet or its modification with two types of REs (E1 and E2) characterized by different ratios of ellagitannins to flavan-3-ols (7.7 and 3.1 for E1 and E2, respectively) and added to a diet at two dosages of polyphenolic compounds (0.15 and 0.30% of a diet; L and H treatments, respectively). Irrespective of polyphenols dietary level, both REs reduced the activity of bacterial β-glucuronidase, increased production of butyric acid in the caecum and reduced triacylglycerols in blood plasma. The E1 treatment at both dosages caused more effective reduction in the concentration of ammonia and elevated acetate level in the caecal digesta than E2. On the other hand, only the E2 treatment lowered value of the atherogenic index when compared with control group. When comparing dosages of REs, a higher one was more potent to reduce the activity of bacterial β-glucosidase, β-, α-galactosidase and lowered value of the HDL profile in plasma. To conclude, REs may favorably modulate the activity of the caecal microbiota and blood lipid profile in rats; however, the intensity of these effects may be related to the dosages of dietary polyphenols and to their profile, e.g., ellagitannins to flavan-3-ols ratio. Full article
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Open AccessReview Properties and Applications of Polyvinyl Alcohol, Halloysite Nanotubes and Their Nanocomposites
Molecules 2015, 20(12), 22833-22847; https://doi.org/10.3390/molecules201219884
Received: 15 October 2015 / Revised: 27 November 2015 / Accepted: 11 December 2015 / Published: 19 December 2015
Cited by 61 | Viewed by 3465 | PDF Full-text (3289 KB) | HTML Full-text | XML Full-text
Abstract
The aim of this review was to analyze/investigate the synthesis, properties, and applications of polyvinyl alcohol–halloysite nanotubes (PVA–HNT), and their nanocomposites. Different polymers with versatile properties are attractive because of their introduction and potential uses in many fields. Synthetic polymers, such as PVA,
[...] Read more.
The aim of this review was to analyze/investigate the synthesis, properties, and applications of polyvinyl alcohol–halloysite nanotubes (PVA–HNT), and their nanocomposites. Different polymers with versatile properties are attractive because of their introduction and potential uses in many fields. Synthetic polymers, such as PVA, natural polymers like alginate, starch, chitosan, or any material with these components have prominent status as important and degradable materials with biocompatibility properties. These materials have been developed in the 1980s and are remarkable because of their recyclability and consideration of the natural continuation of their physical and chemical properties. The fabrication of PVA–HNT nanocomposites can be a potential way to address some of PVA’s limitations. Such nanocomposites have excellent mechanical properties and thermal stability. PVA–HNT nanocomposites have been reported earlier, but without proper HNT individualization and PVA modifications. The properties of PVA–HNT for medicinal and biomedical use are attracting an increasing amount of attention for medical applications, such as wound dressings, drug delivery, targeted-tissue transportation systems, and soft biomaterial implants. The demand for alternative polymeric medical devices has also increased substantially around the world. This paper reviews individualized HNT addition along with crosslinking of PVA for various biomedical applications that have been previously reported in literature, thereby showing the attainability, modification of characteristics, and goals underlying the blending process with PVA. Full article
(This article belongs to the Section Molecular Diversity)
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Open AccessFeature PaperReview Pharmacophore Models and Pharmacophore-Based Virtual Screening: Concepts and Applications Exemplified on Hydroxysteroid Dehydrogenases
Molecules 2015, 20(12), 22799-22832; https://doi.org/10.3390/molecules201219880
Received: 19 November 2015 / Revised: 3 December 2015 / Accepted: 9 December 2015 / Published: 19 December 2015
Cited by 23 | Viewed by 3361 | PDF Full-text (6349 KB) | HTML Full-text | XML Full-text
Abstract
Computational methods are well-established tools in the drug discovery process and can be employed for a variety of tasks. Common applications include lead identification and scaffold hopping, as well as lead optimization by structure-activity relationship analysis and selectivity profiling. In addition, compound-target interactions
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Computational methods are well-established tools in the drug discovery process and can be employed for a variety of tasks. Common applications include lead identification and scaffold hopping, as well as lead optimization by structure-activity relationship analysis and selectivity profiling. In addition, compound-target interactions associated with potentially harmful effects can be identified and investigated. This review focuses on pharmacophore-based virtual screening campaigns specifically addressing the target class of hydroxysteroid dehydrogenases. Many members of this enzyme family are associated with specific pathological conditions, and pharmacological modulation of their activity may represent promising therapeutic strategies. On the other hand, unintended interference with their biological functions, e.g., upon inhibition by xenobiotics, can disrupt steroid hormone-mediated effects, thereby contributing to the development and progression of major diseases. Besides a general introduction to pharmacophore modeling and pharmacophore-based virtual screening, exemplary case studies from the field of short-chain dehydrogenase/reductase (SDR) research are presented. These success stories highlight the suitability of pharmacophore modeling for the various application fields and suggest its application also in futures studies. Full article
(This article belongs to the Special Issue Chemoinformatics)
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Open AccessArticle Studies on Chromatographic Fingerprint and Fingerprinting Profile-Efficacy Relationship of Saxifraga stolonifera Meerb.
Molecules 2015, 20(12), 22781-22798; https://doi.org/10.3390/molecules201219882
Received: 28 September 2015 / Revised: 15 December 2015 / Accepted: 15 December 2015 / Published: 19 December 2015
Cited by 9 | Viewed by 2449 | PDF Full-text (1538 KB) | HTML Full-text | XML Full-text
Abstract
This work investigated the spectrum-effect relationships between high performance liquid chromatography (HPLC) fingerprints and the anti-benign prostatic hyperplasia activities of aqueous extracts from Saxifraga stolonifera. The fingerprints of S. stolonifera from various sources were established by HPLC and evaluated by similarity analysis
[...] Read more.
This work investigated the spectrum-effect relationships between high performance liquid chromatography (HPLC) fingerprints and the anti-benign prostatic hyperplasia activities of aqueous extracts from Saxifraga stolonifera. The fingerprints of S. stolonifera from various sources were established by HPLC and evaluated by similarity analysis (SA), hierarchical clustering analysis (HCA) and principal component analysis (PCA). Nine samples were obtained from these 24 batches of different origins, according to the results of SA, HCA and the common chromatographic peaks area. A testosterone-induced mouse model of benign prostatic hyperplasia (BPH) was used to establish the anti-benign prostatic hyperplasia activities of these nine S. stolonifera samples. The model was evaluated by analyzing prostatic index (PI), serum acid phosphatase (ACP) activity, concentrations of serum dihydrotestosterone (DHT), prostatic acid phosphatase (PACP) and type II 5α-reductase (SRD5A2). The spectrum-effect relationships between HPLC fingerprints and anti-benign prostatic hyperplasia activities were investigated using Grey Correlation Analysis (GRA) and partial least squares regression (PLSR). The results showed that a close correlation existed between the fingerprints and anti-benign prostatic hyperplasia activities, and peak 14 (chlorogenic acid), peak 17 (quercetin 5-O-β-d-glucopyranoside) and peak 18 (quercetin 3-O-β-l-rhamno-pyranoside) in the HPLC fingerprints might be the main active components against anti-benign prostatic hyperplasia. This work provides a general model for the study of spectrum-effect relationships of S. stolonifera by combing HPLC fingerprints with a testosterone-induced mouse model of BPH, which can be employed to discover the principle components of anti-benign prostatic hyperplasia bioactivity. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Tissue- Specific Expression Analysis of Anthocyanin Biosynthetic Genes in White- and Red-Fleshed Grape Cultivars
Molecules 2015, 20(12), 22767-22780; https://doi.org/10.3390/molecules201219883
Received: 18 October 2015 / Revised: 11 December 2015 / Accepted: 15 December 2015 / Published: 19 December 2015
Cited by 9 | Viewed by 2176 | PDF Full-text (1858 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Yan73, a teinturier (dyer) grape variety in China, is one of the few Vitis vinifera cultivars with red-coloured berry flesh. To examine the tissue-specific expression of genes associated with berry colour in Yan73, we analysed the differential accumulation of anthocyanins in the skin
[...] Read more.
Yan73, a teinturier (dyer) grape variety in China, is one of the few Vitis vinifera cultivars with red-coloured berry flesh. To examine the tissue-specific expression of genes associated with berry colour in Yan73, we analysed the differential accumulation of anthocyanins in the skin and flesh tissues of two red-skinned grape varieties with either red (Yan73) or white flesh (Muscat Hamburg) based on HPLC-MS analysis, as well as the differential expression of 18 anthocyanin biosynthesis genes in both varieties by quantitative RT-PCR. The results revealed that the transcripts of GST, OMT, AM3, CHS3, UFGT, MYBA1, F3′5′H, F3H1 and LDOX were barely detectable in the white flesh of Muscat Hamburg. In particular, GST, OMT, AM3, CHS3 and F3H1 showed approximately 50-fold downregulation in the white flesh of Muscat Hamburg compared to the red flesh of Yan73. A correlation analysis between the accumulation of different types of anthocyanins and gene expression indicated that the cumulative expression of GST, F3′5′H, LDOX and MYBA1 was more closely associated with the acylated anthocyanins and the 3′5′-OH anthocyanins, while OMT and AM3 were more closely associated with the total anthocyanins and methoxylated anthocyanins. Therefore, the transcripts of OMT, AM3, GST, F3′5′H, LDOX and MYBA1 explained most of the variation in the amount and composition of anthocyanins in skin and flesh of Yan73. The data suggest that the specific localization of anthocyanins in the flesh tissue of Yan73 is most likely due to the tissue-specific expression of OMT, AM3, GST, F3′5′H, LDOX and MYBA1 in the flesh. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessFeature PaperArticle OSU-6: A Highly Efficient, Metal-Free, Heterogeneous Catalyst for the Click Synthesis of 5-Benzyl and 5-Aryl-1H-tetrazoles
Molecules 2015, 20(12), 22757-22766; https://doi.org/10.3390/molecules201219881
Received: 18 November 2015 / Revised: 7 December 2015 / Accepted: 11 December 2015 / Published: 19 December 2015
Cited by 7 | Viewed by 1860 | PDF Full-text (2132 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
OSU-6, an MCM-41 type hexagonal mesoporous silica with mild Brönsted acid properties, has been used as an efficient, metal-free, heterogeneous catalyst for the click synthesis of 5-benzyl and 5-aryl-1H-tetrazoles from nitriles in DMF at 90 °C. This catalyst offers advantages including
[...] Read more.
OSU-6, an MCM-41 type hexagonal mesoporous silica with mild Brönsted acid properties, has been used as an efficient, metal-free, heterogeneous catalyst for the click synthesis of 5-benzyl and 5-aryl-1H-tetrazoles from nitriles in DMF at 90 °C. This catalyst offers advantages including ease of operation, milder conditions, high yields, and reusability. Studies are presented that demonstrate the robust nature of the catalyst under the optimized reaction conditions. OSU-6 promotes the 1,3-dipolar addition of azides to nitriles without significant degradation or clogging of the nanoporous structure. The catalyst can be reused up to five times without a significant reduction in yield, and it does not require treatment with acid between reactions. Full article
(This article belongs to the Section Organic Chemistry)
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Open AccessReview Unfolded Protein Response and Macroautophagy in Alzheimer’s, Parkinson’s and Prion Diseases
Molecules 2015, 20(12), 22718-22756; https://doi.org/10.3390/molecules201219865
Received: 30 October 2015 / Revised: 30 November 2015 / Accepted: 9 December 2015 / Published: 18 December 2015
Cited by 15 | Viewed by 3193 | PDF Full-text (2421 KB) | HTML Full-text | XML Full-text
Abstract
Proteostasis are integrated biological pathways within cells that control synthesis, folding, trafficking and degradation of proteins. The absence of cell division makes brain proteostasis susceptible to age-related changes and neurodegeneration. Two key processes involved in sustaining normal brain proteostasis are the unfolded protein
[...] Read more.
Proteostasis are integrated biological pathways within cells that control synthesis, folding, trafficking and degradation of proteins. The absence of cell division makes brain proteostasis susceptible to age-related changes and neurodegeneration. Two key processes involved in sustaining normal brain proteostasis are the unfolded protein response and autophagy. Alzheimer’s disease (AD), Parkinson’s disease (PD) and prion diseases (PrDs) have different clinical manifestations of neurodegeneration, however, all share an accumulation of misfolded pathological proteins associated with perturbations in unfolded protein response and macroautophagy. While both the unfolded protein response and macroautophagy play an important role in the prevention and attenuation of AD and PD progression, only macroautophagy seems to play an important role in the development of PrDs. Macroautophagy and unfolded protein response can be modulated by pharmacological interventions. However, further research is necessary to better understand the regulatory pathways of both processes in health and neurodegeneration to be able to develop new therapeutic interventions. Full article
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Open AccessArticle Phenolic Assesment of Uncaria tomentosa L. (Cat’s Claw): Leaves, Stem, Bark and Wood Extracts
Molecules 2015, 20(12), 22703-22717; https://doi.org/10.3390/molecules201219875
Received: 14 October 2015 / Revised: 7 December 2015 / Accepted: 10 December 2015 / Published: 18 December 2015
Cited by 14 | Viewed by 2907 | PDF Full-text (2451 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The phenolic composition of extracts from Uncaria tomentosa L. from different regions of Costa Rica was studied using advanced analytical techniques such as UPLC/TQ-ESI-MS and 13C-NMR. Samples from leaves, stems, bark and wood (n = 22) were subjected to extraction to
[...] Read more.
The phenolic composition of extracts from Uncaria tomentosa L. from different regions of Costa Rica was studied using advanced analytical techniques such as UPLC/TQ-ESI-MS and 13C-NMR. Samples from leaves, stems, bark and wood (n = 22) were subjected to extraction to obtain phenolic and alkaloid extracts, separately. Comparatively, higher values of total phenolic content were observed for leaves, stems and bark (225–494 gallic acid equivalents/g) than for wood extracts (40–167 gallic acid equivalents/g). A total of 32 non-flavonoid and flavonoid compounds were identified in the phenolic extracts: hydroxybenzoic acids (benzoic, salicylic, 4-hydroxybenzoic, prochatechuic, gallic, syringic and vanillic acids), hydroxycinnamic acids (p-coumaric, caffeic, ferulic and isoferulic acids), flavan-3-ols monomers [(+)-catechin and (−)-epicatechin)], procyanidin dimers (B1, B2, B3, B4, B5, B7 and two other of unknown structure) and trimers (C1, T2 and one of unknown structure), flavalignans (four unknown structures pertaining to the cinchonain family) and propelargonidin dimers (four unknown structures, reported for the first time in U. tomentosa). Additionally, alkaloid extracts obtained from the plant residue after phenolic extraction exhibited a content of tetracyclic and pentacyclic alkaloids ranging between 95 and 275 mg/100 g of dry material for bark extracts, and between 30 and 704 mg/100 g for leaves extracts. In addition, a minor alkaloid was isolated and characterized, namely 18,19-dehydrocorynoxinoic acid. Our results confirmed the feasibility of U. tomentosa as a suitable raw material for obtaining phenolic- and alkaloid-rich extracts of potential interest. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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Open AccessArticle Solid-State Characterization and Biological Activity of Betulonic Acid Derivatives
Molecules 2015, 20(12), 22691-22702; https://doi.org/10.3390/molecules201219876
Received: 1 November 2015 / Revised: 4 December 2015 / Accepted: 7 December 2015 / Published: 18 December 2015
Cited by 2 | Viewed by 1697 | PDF Full-text (2263 KB) | HTML Full-text | XML Full-text
Abstract
Betulonic acid belongs to the pentacyclic triterpenic derivative class and can be obtained through the selective oxidation of betulin. In this study we set obtaining several functionalized derivatives of this compound by its condensation with several amino compounds such as aminoguanidine, hydroxylamine, n
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Betulonic acid belongs to the pentacyclic triterpenic derivative class and can be obtained through the selective oxidation of betulin. In this study we set obtaining several functionalized derivatives of this compound by its condensation with several amino compounds such as aminoguanidine, hydroxylamine, n-butylamine and thiosemicarbazide as our goal. The functionalization of the parent compound led to several molecules with antiproliferative potential, the most promising being 3–2-carbamothioylhydrazonolup-20(29)-en-28-oic acid. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Short-Term and Sub-Chronic Dietary Exposure to Aspalathin-Enriched Green Rooibos (Aspalathus linearis) Extract Affects Rat Liver Function and Antioxidant Status
Molecules 2015, 20(12), 22674-22690; https://doi.org/10.3390/molecules201219868
Received: 9 November 2015 / Revised: 9 December 2015 / Accepted: 11 December 2015 / Published: 18 December 2015
Cited by 5 | Viewed by 2406 | PDF Full-text (1075 KB) | HTML Full-text | XML Full-text | Correction
Abstract
An aspalathin-enriched green rooibos (Aspalathus linearis) extract (GRE) was fed to male Fischer rats in two independent studies for 28 and 90 days. The average dietary total polyphenol (TP) intake was 756 and 627 mg Gallic acid equivalents (GAE)/kg body weight
[...] Read more.
An aspalathin-enriched green rooibos (Aspalathus linearis) extract (GRE) was fed to male Fischer rats in two independent studies for 28 and 90 days. The average dietary total polyphenol (TP) intake was 756 and 627 mg Gallic acid equivalents (GAE)/kg body weight (bw)/day over 28 and 90 days, respectively, equaling human equivalent doses (HEDs) of 123 and 102 GAE mg/kg bw/day. Aspalathin intake of 295 mg/kg bw/day represents a HED of 48 mg/kg bw/day (90 day study). Consumption of GRE increased feed intake significantly (p < 0.05) compared to the control after 90 days, but no effect on body and organ weight parameters was observed. GRE significantly (p < 0.05) reduced serum total cholesterol and iron levels, whilst significantly (p < 0.05) increasing alkaline phosphatase enzyme activity after 90 days. Endogenous antioxidant enzyme activity in the liver, i.e., catalase and superoxide dismutase activity, was not adversely affected. Glutathione reductase activity significantly (p < 0.05) increased after 28 days, while glutathione (GSH) content was decreased after 90 days, suggesting an altered glutathione redox cycle. Quantitative Real Time polymerase chain reaction (PCR) analysis showed altered expression of certain antioxidant defense and oxidative stress related genes, indicative, among others, of an underlying oxidative stress related to changes in the GSH redox pathway and possible biliary dysfunction. Full article
(This article belongs to the Special Issue Antioxidants—A Risk-Benefit Analysis for Health)
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Open AccessArticle Potassium Hexacyanoferrate (III)-Catalyzed Dimerization of Hydroxystilbene: Biomimetic Synthesis of Indane Stilbene Dimers
Molecules 2015, 20(12), 22662-22673; https://doi.org/10.3390/molecules201219872
Received: 16 November 2015 / Revised: 7 December 2015 / Accepted: 9 December 2015 / Published: 18 December 2015
Cited by 3 | Viewed by 1923 | PDF Full-text (1885 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Using potassium hexacyanoferrate (III)–sodium acetate as oxidant, the oxidative coupling reaction of isorhapontigenin and resveratrol in aqueous acetone resulted in the isolation of three new indane dimers 4, 6, and 7, together with six known stilbene dimers. Indane dimer 5
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Using potassium hexacyanoferrate (III)–sodium acetate as oxidant, the oxidative coupling reaction of isorhapontigenin and resveratrol in aqueous acetone resulted in the isolation of three new indane dimers 4, 6, and 7, together with six known stilbene dimers. Indane dimer 5 was obtained for the first time by direct transformation from isorhapontigenin. The structures and relative configurations of the dimers were elucidated using spectral analysis, and their possible formation mechanisms were discussed. The results indicate that this reaction could be used as a convenient method for the semi-synthesis of indane dimers because of the mild conditions and simple reaction products. Full article
(This article belongs to the Section Bioorganic Chemistry)
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Open AccessArticle Storage Stability of Kinnow Fruit (Citrus reticulata) as Affected by CMC and Guar Gum-Based Silver Nanoparticle Coatings
Molecules 2015, 20(12), 22645-22661; https://doi.org/10.3390/molecules201219870
Received: 6 November 2015 / Revised: 4 December 2015 / Accepted: 11 December 2015 / Published: 18 December 2015
Cited by 8 | Viewed by 2422 | PDF Full-text (4799 KB) | HTML Full-text | XML Full-text
Abstract
The influence of carboxy methyl cellulose (CMC) and guargum-based coatings containing silver nanoparticles was studied on the postharvest storage stability of the kinnow mandarin (Citrus reticulata cv. Blanco) for a period of 120 days (85%–90% relative humidity) at 4 °C and 10
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The influence of carboxy methyl cellulose (CMC) and guargum-based coatings containing silver nanoparticles was studied on the postharvest storage stability of the kinnow mandarin (Citrus reticulata cv. Blanco) for a period of 120 days (85%–90% relative humidity) at 4 °C and 10 °C. Physicochemical and microbiological qualities were monitored after every 15 days of storage. Overall results revealed an increase in total soluble solid (TSS), total sugars, reducing sugars and weight loss but this increase was comparatively less significant in coated fruits stored at 4 °C. Ascorbic acid, total phenolics, and antioxidant activity was significantly enhanced in coated fruits stored at 4 °C. Titratable acidity significantly decreased during storage except for coated kinnow stored at 4 °C. In control samples stored at 10 °C, high intensity of fruit rotting and no chilling injury was observed. Total aerobic psychrotrophic bacteria and yeast and molds were noticed in all treatments during storage but the growth was not significant in coated fruits at 4 °C. Kinnow fruit can be kept in good quality after coating for four months at 4 °C and for 2 months at 10 °C. Full article
(This article belongs to the Special Issue Pharmaceutical Nanotechnology: Novel Approaches)
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Open AccessArticle Metathetical Redox Reaction of (Diacetoxyiodo)arenes and Iodoarenes
Molecules 2015, 20(12), 22635-22644; https://doi.org/10.3390/molecules201219874
Received: 25 November 2015 / Revised: 10 December 2015 / Accepted: 15 December 2015 / Published: 17 December 2015
Cited by 6 | Viewed by 2196 | PDF Full-text (2718 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The oxidation of iodoarenes is central to the field of hypervalent iodine chemistry. It was found that the metathetical redox reaction between (diacetoxyiodo)arenes and iodoarenes is possible in the presence of a catalytic amount of Lewis acid. This discovery opens a new strategy
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The oxidation of iodoarenes is central to the field of hypervalent iodine chemistry. It was found that the metathetical redox reaction between (diacetoxyiodo)arenes and iodoarenes is possible in the presence of a catalytic amount of Lewis acid. This discovery opens a new strategy to access (diacetoxyiodo)arenes. A computational study is provided to rationalize the results observed. Full article
(This article belongs to the Special Issue Hypervalent Iodine Chemistry)
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Open AccessArticle Analysis of Indole Alkaloids from Rhazya stricta Hairy Roots by Ultra-Performance Liquid Chromatography-Mass Spectrometry
Molecules 2015, 20(12), 22621-22634; https://doi.org/10.3390/molecules201219873
Received: 28 October 2015 / Revised: 10 December 2015 / Accepted: 11 December 2015 / Published: 17 December 2015
Cited by 3 | Viewed by 2212 | PDF Full-text (1367 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Rhazya stricta Decne. (Apocynaceae) contains a large number of terpenoid indole alkaloids (TIAs). This study focused on the composition of alkaloids obtained from transformed hairy root cultures of R. stricta employing ultra-performance liquid chromatography-mass spectrometry (UPLC-MS). In the UPLC-MS analyses, a total of
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Rhazya stricta Decne. (Apocynaceae) contains a large number of terpenoid indole alkaloids (TIAs). This study focused on the composition of alkaloids obtained from transformed hairy root cultures of R. stricta employing ultra-performance liquid chromatography-mass spectrometry (UPLC-MS). In the UPLC-MS analyses, a total of 20 TIAs were identified from crude extracts. Eburenine and vincanine were the main alkaloids followed by polar glucoalkaloids, strictosidine lactam and strictosidine. Secodine-type alkaloids, tetrahydrosecodinol, tetrahydro- and dihydrosecodine were detected too. The occurrence of tetrahydrosecodinol was confirmed for the first time for R. stricta. Furthermore, two isomers of yohimbine, serpentine and vallesiachotamine were identified. The study shows that a characteristic pattern of biosynthetically related TIAs can be monitored in Rhazya hairy root crude extract by this chromatographic method. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessReview Chemoprevention of Breast Cancer by Dietary Polyphenols
Molecules 2015, 20(12), 22578-22620; https://doi.org/10.3390/molecules201219864
Received: 2 October 2015 / Revised: 4 December 2015 / Accepted: 8 December 2015 / Published: 17 December 2015
Cited by 24 | Viewed by 4463 | PDF Full-text (9006 KB) | HTML Full-text | XML Full-text
Abstract
The review will discuss in detail the effects of polyphenols on breast cancer, including both the advantages and disadvantages of the applications of these natural compounds. First, we focus on the characterization of the main classes of polyphenols and then on in vitro
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The review will discuss in detail the effects of polyphenols on breast cancer, including both the advantages and disadvantages of the applications of these natural compounds. First, we focus on the characterization of the main classes of polyphenols and then on in vitro and in vivo experiments carried out in breast cancer models. Since the therapeutic effects of the administration of a single type of polyphenol might be limited because of the reduced bioavailability of these drugs, investigations on combination of several polyphenols or polyphenols with conventional therapy will also be discussed. In addition, we present recent data focusing on clinical trials with polyphenols and new approaches with nanoparticles in breast cancer. Besides the clinical and translational findings this review systematically summarizes our current knowledge about the molecular mechanisms of anti-cancer effects of polyphenols, which are related to apoptosis, cell cycle regulation, plasma membrane receptors, signaling pathways and epigenetic mechanisms. At the same time the effects of polyphenols on primary tumor, metastasis and angiogenesis in breast cancer are discussed. The increasing enthusiasm regarding the combination of polyphenols and conventional therapy in breast cancer might lead to additional efforts to motivate further research in this field. Full article
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Open AccessCommunication Seven New Tetrahydroanthraquinones from the Root of Prismatomeris connata and Their Cytotoxicity against Lung Tumor Cell Growth
Molecules 2015, 20(12), 22565-22577; https://doi.org/10.3390/molecules201219856
Received: 11 November 2015 / Revised: 6 December 2015 / Accepted: 7 December 2015 / Published: 17 December 2015
Cited by 2 | Viewed by 1813 | PDF Full-text (2402 KB) | HTML Full-text | XML Full-text
Abstract
The root of Prismatomeris connata has been used in China for centuries as the medicinal herb “Huang Gen” (HG), but its phytochemicals or active ingredients are not well understood. In this study, we performed chemical analysis of the ethyl acetate fraction
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The root of Prismatomeris connata has been used in China for centuries as the medicinal herb “Huang Gen” (HG), but its phytochemicals or active ingredients are not well understood. In this study, we performed chemical analysis of the ethyl acetate fraction of a HG ethanol extract. We thus isolated seven new tetrahydroanthraquinones, prisconnatanones C–I (compounds 17) from the root of P. connata and identified their structures using spectroscopic analyses. Their absolute configurations were established by both modified Mosher’s and Mo2OAc4 methods, and ORD techniques. Their cytotoxicity was tested in a panel of human lung tumor cells (H1229, HTB179, A549 and H520 cell lines). Prisconnatanone I (7) showed the highest activity, with an IC50 value ranging from 2.7 µM to 3.9 µM in the suppression of tumor cell growth, and the others with chelated phenolic hydroxyls exhibited relatively lower activity (IC50: 8–20 µM). In conclusion, these data suggest that some of the natural tetrahydroanthraquinones in HG are bioactive, and hydroxylation at C-1 significantly increases the cytotoxicity of these compounds against lung tumor cell growth. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Anti-Ulcerogenic Properties of Lycium chinense Mill Extracts against Ethanol-Induced Acute Gastric Lesion in Animal Models and Its Active Constituents
Molecules 2015, 20(12), 22553-22564; https://doi.org/10.3390/molecules201219867
Received: 29 October 2015 / Revised: 10 December 2015 / Accepted: 10 December 2015 / Published: 16 December 2015
Cited by 12 | Viewed by 2259 | PDF Full-text (3810 KB) | HTML Full-text | XML Full-text
Abstract
The objective of this study was to explore the gastroprotective properties of the aerial part of Lycium chinense Mill (LCA) against ethanol-induced gastric mucosa lesions in mice models. Administration of LCA at doses of 50, 100, 200 and 400 mg/kg body weight prior
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The objective of this study was to explore the gastroprotective properties of the aerial part of Lycium chinense Mill (LCA) against ethanol-induced gastric mucosa lesions in mice models. Administration of LCA at doses of 50, 100, 200 and 400 mg/kg body weight prior to ethanol consumption dose dependently inhibited gastric ulcers. The gastric mucosal injury was analyzed by gastric juice acidity, glutathione (GSH), superoxide dismutase (SOD), malondialdehyde (MDA), myeloperoxidase (MPO) activities. Furthermore, the levels of the inflammatory mediators, tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6) and interleukin-1β (IL-1β) in serum were also analyzed using ELISA. Pathological changes were also observed with the aid of hematoxylin-eosin (HE) staining. Our results indicated that LCA significantly reduced the levels of MPO, MDA and increased SOD and GSH activities. Furthermore, LCA also significantly inhibited the levels of TNF-α, IL-6, and IL-1β in the serum of ulcerated mice in a dose dependent manner. Immunohistological analysis indicated that LCA also significantly attenuated the overexpression of nuclear factor-κB in pretreated mice models. This findings suggests Lycium chinense Mill possesses gastroprotective properties against ethanol-induced gastric injury and could be a possible therapeutic intervention in the treatment and management of gastric ulcers. Full article
(This article belongs to the collection Bioactive Compounds)
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Open AccessCommunication Antiproliferative Activities of Water Infusions from Leaves of Five Cornus L. Species
Molecules 2015, 20(12), 22546-22552; https://doi.org/10.3390/molecules201219786
Received: 27 October 2015 / Revised: 20 November 2015 / Accepted: 24 November 2015 / Published: 16 December 2015
Cited by 6 | Viewed by 1667 | PDF Full-text (394 KB) | HTML Full-text | XML Full-text
Abstract
Cornaceae plants are known for their edible berries, and their leaves are used as tea. In the present study aqueous leaf extracts from Cornus mas (CM), C. alba (CA), C. flaviramea (CF), C. kousa (CK), and C. officinalis (CO) were tested for their
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Cornaceae plants are known for their edible berries, and their leaves are used as tea. In the present study aqueous leaf extracts from Cornus mas (CM), C. alba (CA), C. flaviramea (CF), C. kousa (CK), and C. officinalis (CO) were tested for their antiproliferative activity in human breast cancer cells (MCF-7). Dose- (50–750 µg/mL) and time (24, 48, 72 h)-dependent antiproliferative effects were measured by WST-1, and correlated with the content of flavonoids (FL), total hydroxycinnamic derivatives (THD), total polyphenols (TP) and tannins (T). Extracts induced time dependent decreases in cell survival; CA, CO and CM were the most effective (11.2%, 10.3% and 11.1%, after 72 h). The ED50 (effective dose) values were similar for all extracts and times tested. The THD and TP were identical in all samples, while a two-fold higher T content was present in CK and CO, and of FL in CF. The maximal effects (% of surviving cells) negatively correlated with the T and TP levels, and positively with FL and THD. The results demonstrate the significant antiproliferative effects of the tested water extracts in MCF-7 cells, in which CA, CO and CM are the most effective; and the effectiveness is related to the T and TP contents. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle A Nanostructured Lipid System as a Strategy to Improve the in Vitro Antibacterial Activity of Copper(II) Complexes
Molecules 2015, 20(12), 22534-22545; https://doi.org/10.3390/molecules201219822
Received: 30 October 2015 / Revised: 23 November 2015 / Accepted: 24 November 2015 / Published: 16 December 2015
Cited by 6 | Viewed by 1956 | PDF Full-text (1097 KB) | HTML Full-text | XML Full-text
Abstract
The aim of this study was to construct a nanostructured lipid system as a strategy to improve the in vitro antibacterial activity of copper(II) complexes. New compounds with the general formulae [CuX2(INH)2]·nH2O (X = Cl and
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The aim of this study was to construct a nanostructured lipid system as a strategy to improve the in vitro antibacterial activity of copper(II) complexes. New compounds with the general formulae [CuX2(INH)2]·nH2O (X = Cl and n = 1 (1); X = NCS and n = 5 (2); X = NCO and n = 4 (3); INH = isoniazid, a drug widely used to treat tuberculosis) derived from the reaction between the copper(II) chloride and isoniazid in the presence or absence of pseudohalide ions (NCS or NCO) were synthesized and characterized by infrared spectrometry, electronic absorption spectroscopy, electron paramagnetic resonance (EPR) spectroscopy, elemental analysis, melting points and complexometry with 2,2′,2′′,2′′′-(Ethane-1,2-diyldinitrilo)tetraacetic acid (EDTA). The characterization techniques allowed us to confirm the formation of the copper(II) complexes. The Cu(II) complexes were loaded into microemulsion (MEs) composed of 10% phase oil (cholesterol), 10% surfactant [soy oleate and Brij® 58 (1:2)] and 80% aqueous phase (phosphate buffer pH = 7.4) prepared by sonication. The Cu(II) complex-loaded MEs displayed sizes ranging from 158.0 ± 1.060 to 212.6 ± 1.539 nm, whereas the polydispersity index (PDI) ranged from 0.218 ± 0.007 to 0.284 ± 0.034. The antibacterial activity of the free compounds and those that were loaded into the MEs against Staphylococcus aureus ATCC® 25923 and Escherichia coli ATCC® 25922, as evaluated by a microdilution technique, and the cytotoxicity index (IC50) against the Vero cell line (ATCC® CCL-81TM) were used to calculate the selectivity index (SI). Among the free compounds, only compound 2 (MIC 500 μg/mL) showed activity for S. aureus. After loading the compounds into the MEs, the antibacterial activity of compounds 1, 2 and 3 was significantly increased against E. coli (MIC’s 125, 125 and 500 μg/mL, respectively) and S. aureus (MICs 250, 500 and 125 μg/mL, respectively). The loaded compounds were less toxic against the Vero cell line, especially compound 1 (IC50 from 109.5 to 319.3 μg/mL). The compound 2- and 3-loaded MEs displayed the best SI for E. coli and S. aureus, respectively. These results indicated that the Cu(II) complex-loaded MEs were considerably more selective than the free compounds, in some cases, up to 40 times higher. Full article
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Open AccessArticle Novel Polycarbo-Substituted Imidazo[1,2-c]quinazolines: Synthesis and Cytotoxicity Study
Molecules 2015, 20(12), 22520-22533; https://doi.org/10.3390/molecules201219863
Received: 9 November 2015 / Revised: 30 November 2015 / Accepted: 1 December 2015 / Published: 15 December 2015
Cited by 5 | Viewed by 1524 | PDF Full-text (1226 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Amination of the 2-aryl-6-bromo-4-chloro-8-iodoquinazolines with 2-aminoethanol followed by acid-promoted cyclodehydration of the incipient 2-((6,8-dihalo-2-phenylquinazolin-4-yl)amino)ethanols afforded the corresponding novel 5-aryl-9-bromo-7-iodo-2,3-dihydro-2H-imidazo[1,2-c]quinazolines. The latter were, in turn, subjected to sequential (Sonogashira and Suzuki-Miyaura) and one-pot two-step (Sonogashira/Stille) cross-coupling reactions to afford diversely
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Amination of the 2-aryl-6-bromo-4-chloro-8-iodoquinazolines with 2-aminoethanol followed by acid-promoted cyclodehydration of the incipient 2-((6,8-dihalo-2-phenylquinazolin-4-yl)amino)ethanols afforded the corresponding novel 5-aryl-9-bromo-7-iodo-2,3-dihydro-2H-imidazo[1,2-c]quinazolines. The latter were, in turn, subjected to sequential (Sonogashira and Suzuki-Miyaura) and one-pot two-step (Sonogashira/Stille) cross-coupling reactions to afford diversely functionalized polycarbo-substituted 2H-imidazo[1,2-c]quinazolines. The imidazoquinazolines were screened for in vitro cytotoxicity against human breast adenocarcinoma (MCF-7) cells and human cervical cancer (HeLa) cells. Full article
(This article belongs to the Section Bioorganic Chemistry)
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Open AccessArticle Syntheses of 4-Indolylquinoline Derivatives via Reductive Cyclization of Indolylnitrochalcone Derivatives by Fe/HCl
Molecules 2015, 20(12), 22499-22519; https://doi.org/10.3390/molecules201219862
Received: 23 November 2015 / Revised: 7 December 2015 / Accepted: 8 December 2015 / Published: 15 December 2015
Cited by 2 | Viewed by 1816 | PDF Full-text (17734 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
An easy and efficient procedure for the synthesis of 4-indolylquinoline derivatives is described. This process involves two steps, the first of which is the Michael addition of indole to nitrochalcones promoted by sulfamic acid under solvent free conditions and the second step is
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An easy and efficient procedure for the synthesis of 4-indolylquinoline derivatives is described. This process involves two steps, the first of which is the Michael addition of indole to nitrochalcones promoted by sulfamic acid under solvent free conditions and the second step is a reductive cyclization of the indolylnitrochalcone intermediates to 4-indolylquinoline derivatives by Fe/HCl in ethanol. In both steps, the reactions are clean and the yields of products are high. Full article
(This article belongs to the collection Heterocyclic Compounds)
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Open AccessArticle Green Chemistry Approach for Synthesis of Effective Anticancer Palladium Nanoparticles
Molecules 2015, 20(12), 22476-22498; https://doi.org/10.3390/molecules201219860
Received: 26 November 2015 / Revised: 9 December 2015 / Accepted: 10 December 2015 / Published: 15 December 2015
Cited by 24 | Viewed by 3160 | PDF Full-text (5589 KB) | HTML Full-text | XML Full-text
Abstract
The purpose of this study was to design and synthesize Palladium nanoparticles (PdNPs) using an environmentally friendly approach and evaluate the in vitro efficacy of PdNPs in human ovarian cancer A2780 cells. Ultraviolet-Visible (UV-Vis) spectroscopy was used to monitor the conversion of Pd(II)
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The purpose of this study was to design and synthesize Palladium nanoparticles (PdNPs) using an environmentally friendly approach and evaluate the in vitro efficacy of PdNPs in human ovarian cancer A2780 cells. Ultraviolet-Visible (UV-Vis) spectroscopy was used to monitor the conversion of Pd(II) ions to Pd(0)NPs. X-ray diffraction (XRD) revealed the crystallinity of the as-synthesized PdNPs and Fourier transform infrared spectroscopy (FTIR) further confirmed the role of the leaf extract of Evolvulus alsinoides as a reducing and stabilizing agent for the synthesis of PdNPs. Dynamic light scattering (DLS) and transmission electron microscopy (TEM) showed that the average size of the NPs was 5 nm. After a 24-h exposure to PdNPs, cell viability and light microscopy assays revealed the dose-dependent toxicity of the PdNPs. Furthermore, the dose-dependent cytotoxicity of the PdNPs was confirmed by lactate dehydrogenase (LDH), increased reactive oxygen species (ROS) generation, activation of PdNPs-induced autophagy, impairment of mitochondrial membrane potential (MMP), enhanced caspase-3 activity, and detection of TUNEL-positive cells. Our study demonstrates a single, simple, dependable and green approach for the synthesis of PdNPs using leaf extracts of Evolvulus alsinoides. Furthermore, the in vitro efficacy of PdNPs in human ovarian cancer cells suggests that it could be an effective therapeutic agent for cancer therapy. Full article
(This article belongs to the Special Issue Pharmaceutical Nanotechnology: Novel Approaches)
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Open AccessArticle Phenolic Profiling of Duchesnea indica Combining Macroporous Resin Chromatography (MRC) with HPLC-ESI-MS/MS and ESI-IT-MS
Molecules 2015, 20(12), 22463-22475; https://doi.org/10.3390/molecules201219859
Received: 14 October 2015 / Revised: 20 November 2015 / Accepted: 10 December 2015 / Published: 15 December 2015
Cited by 13 | Viewed by 2184 | PDF Full-text (775 KB) | HTML Full-text | XML Full-text
Abstract
Duchesnea indica (D. indica) is an important traditional Chinese medicine, and has long been clinically used to treat cancer in Asian countries. It has been described previously as a rich source of phenolic compounds with a broad array of diversified structures,
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Duchesnea indica (D. indica) is an important traditional Chinese medicine, and has long been clinically used to treat cancer in Asian countries. It has been described previously as a rich source of phenolic compounds with a broad array of diversified structures, which are the major active ingredients. However, an accurate and complete phenolic profiling has not been determined yet. In the present work, the total phenolic compounds in crude extracts from D. indica were enriched and fractionated over a macroporous resin column, then identified by HPLC-ESI-MS/MS and ESI-IT-MS (ion trap MS). A total of 27 phenolic compounds were identified in D. indica, of which 21 compounds were identified for the first time. These 27 phenolic compounds encompassing four phenolic groups, including ellagitannins, ellagic acid and ellagic acid glycosides, hydroxybenzoic acid and hydroxycinnamic acid derivatives, and flavonols, were then successfully quantified using peak areas against those of the corresponding standards with good linearity (R2 > 0.998) in the range of the tested concentrations. As a result, the contents of individual phenolic compounds varied from 6.69 mg per 100 g dry weight (DW) for ellagic acid to 71.36 mg per 100 g DW for brevifolin carboxylate. Not only did this study provide the first phenolic profiling of D. indica, but both the qualitative identification and the subsequent quantitative analysis of 27 phenolic compounds from D. indica should provide a good basis for future exploration of this valuable medicinal plant. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Authentication of Cordyceps sinensis by DNA Analyses: Comparison of ITS Sequence Analysis and RAPD-Derived Molecular Markers
Molecules 2015, 20(12), 22454-22462; https://doi.org/10.3390/molecules201219861
Received: 27 November 2015 / Revised: 8 December 2015 / Accepted: 10 December 2015 / Published: 15 December 2015
Cited by 12 | Viewed by 2499 | PDF Full-text (2963 KB) | HTML Full-text | XML Full-text
Abstract
Cordyceps sinensis is an endoparasitic fungus widely used as a tonic and medicinal food in the practice of traditional Chinese medicine (TCM). In historical usage, Cordyceps specifically is referring to the species of C. sinensis. However, a number of closely related species
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Cordyceps sinensis is an endoparasitic fungus widely used as a tonic and medicinal food in the practice of traditional Chinese medicine (TCM). In historical usage, Cordyceps specifically is referring to the species of C. sinensis. However, a number of closely related species are named themselves as Cordyceps, and they are sold commonly as C. sinensis. The substitutes and adulterants of C. sinensis are often introduced either intentionally or accidentally in the herbal market, which seriously affects the therapeutic effects or even leads to life-threatening poisoning. Here, we aim to identify Cordyceps by DNA sequencing technology. Two different DNA-based approaches were compared. The internal transcribed spacer (ITS) sequences and the random amplified polymorphic DNA (RAPD)-sequence characterized amplified region (SCAR) were developed here to authenticate different species of Cordyceps. Both approaches generally enabled discrimination of C. sinensis from others. The application of the two methods, supporting each other, increases the security of identification. For better reproducibility and faster analysis, the SCAR markers derived from the RAPD results provide a new method for quick authentication of Cordyceps. Full article
(This article belongs to the Section Molecular Diversity)
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Open AccessArticle New Ent-Kaurane-Type Diterpene Glycosides and Benzophenone from Ranunculus muricatus Linn.
Molecules 2015, 20(12), 22445-22453; https://doi.org/10.3390/molecules201219801
Received: 21 October 2015 / Revised: 16 November 2015 / Accepted: 21 November 2015 / Published: 15 December 2015
Cited by 2 | Viewed by 1677 | PDF Full-text (1186 KB) | HTML Full-text | XML Full-text
Abstract
Two new ent-kaurane diterpene glycosides, ranunculosides A (1) and B (2), and a new benzophenone, ranunculone C (3), were isolated from the aerial part of Ranunculus muricatus Linn. The chemical structures of compounds 13
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Two new ent-kaurane diterpene glycosides, ranunculosides A (1) and B (2), and a new benzophenone, ranunculone C (3), were isolated from the aerial part of Ranunculus muricatus Linn. The chemical structures of compounds 13 were established to be (2S)-ent-kauran-2β-ol-15-en-14-O-β-d-glucopyranoside, (2S,4S)-ent-kauran-2β,18-diol-15-en-14-O-β-d-glucopyranoside, and (R)-3-[2-(3,4-dihydroxybenzoyl)-4,5-dihydroxy-phenyl]-2-hydroxylpropanoic acid, respectively, by spectroscopic data and chemical methods. The absolute configuration of 1 was determined by the combinational application of RP-HPLC analysis and Mosher’s method. Full article
(This article belongs to the Section Molecular Diversity)
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