Molecules

936 KiB

Open AccessReview

Protein-Carbohydrate Interaction between Sperm and the Egg-Coating Envelope and Its Regulation by Dicalcin, a Xenopus laevis Zona Pellucida Protein-Associated Protein

by Naofumi Miwa

Molecules 2015, 20(5), 9468-9486; https://doi.org/10.3390/molecules20059468 - 22 May 2015

Cited by 13 | Viewed by 7167

Abstract

Protein-carbohydrate interaction regulates multiple important processes during fertilization, an essential biological event where individual gametes undergo intercellular recognition to fuse and generate a zygote. In the mammalian female reproductive tract, sperm temporarily adhere to the oviductal epithelium via the complementary interaction between carbohydrate-binding [...] Read more.

Protein-carbohydrate interaction regulates multiple important processes during fertilization, an essential biological event where individual gametes undergo intercellular recognition to fuse and generate a zygote. In the mammalian female reproductive tract, sperm temporarily adhere to the oviductal epithelium via the complementary interaction between carbohydrate-binding proteins on the sperm membrane and carbohydrates on the oviductal cells. After detachment from the oviductal epithelium at the appropriate time point following ovulation, sperm migrate and occasionally bind to the extracellular matrix, called the zona pellucida (ZP), which surrounds the egg, thereafter undergoing the exocytotic acrosomal reaction to penetrate the envelope and to reach the egg plasma membrane. This sperm-ZP interaction also involves the direct interaction between sperm carbohydrate-binding proteins and carbohydrates within the ZP, most of which have been conserved across divergent species from mammals to amphibians and echinoderms. This review focuses on the carbohydrate-mediated interaction of sperm with the female reproductive tract, mainly the interaction between sperm and the ZP, and introduces the fertilization-suppressive action of dicalcin, a Xenopus laevis ZP protein-associated protein. The action of dicalcin correlates significantly with a dicalcin-dependent change in the lectin-staining pattern within the ZP, suggesting a unique role of dicalcin as an inherent protein that is capable of regulating the affinity between the lectin and oligosaccharides attached on its target glycoprotein. Full article

(This article belongs to the Special Issue Protein-Carbohydrate Interactions, and Beyond)

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1008 KiB

Open AccessArticle

Relationship between High-Performance Liquid Chromatography Fingerprints and Uric Acid-Lowering Activities of Cichorium intybus L.

by Chun-Sheng Zhu, Bing Zhang, Zhi-Jian Lin, Xue-Jie Wang, Yue Zhou, Xiao-Xia Sun and Ming-Liang Xiao

Molecules 2015, 20(5), 9455-9467; https://doi.org/10.3390/molecules20059455 - 22 May 2015

Cited by 29 | Viewed by 6861

Abstract

This study aimed to explore the spectrum-effect relationships between high-performance liquid chromatography fingerprints and the uric acid-lowering activities of chicory. Chemical fingerprints of chicory samples from ten different sources were determined by high-performance liquid chromatography, and then investigated by similarity analysis and hierarchical [...] Read more.

This study aimed to explore the spectrum-effect relationships between high-performance liquid chromatography fingerprints and the uric acid-lowering activities of chicory. Chemical fingerprints of chicory samples from ten different sources were determined by high-performance liquid chromatography, and then investigated by similarity analysis and hierarchical clustering analysis. Pharmacodynamics experiments were conducted in animals to obtain the uric acid-lowering activity information of each chicory sample. The spectrum-effect relationships between chemical fingerprints and the uric acid-lowering activities of chicory were established by canonical correlation analysis. The structures of potential effective peaks were identified by liquid chromatography with tandem mass spectrometry. The results showed that a close correlation existed between the spectrum and effect of chicory. Aesculin, chlorogenic acid, chicoric acid, isochlorogenic acid A/B/C and 13,14-seco-stigma5(6),14(15)-diene-3α-ol might be the main effective constituents. This work provides a general model of the combination of high-performance liquid chromatography and uric acid-lowering activities to study the spectrum-effect relationships of chicory, which can be used to discover the principle components responsible for the bioactivity. Full article

(This article belongs to the Section Natural Products Chemistry)

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1539 KiB

Open AccessReview

Palladium-Catalyzed Modification of Unprotected Nucleosides, Nucleotides, and Oligonucleotides

by Kevin H. Shaughnessy

Molecules 2015, 20(5), 9419-9454; https://doi.org/10.3390/molecules20059419 - 22 May 2015

Cited by 79 | Viewed by 11378

Abstract

Synthetic modification of nucleoside structures provides access to molecules of interest as pharmaceuticals, biochemical probes, and models to study diseases. Covalent modification of the purine and pyrimidine bases is an important strategy for the synthesis of these adducts. Palladium-catalyzed cross-coupling is a powerful [...] Read more.

Synthetic modification of nucleoside structures provides access to molecules of interest as pharmaceuticals, biochemical probes, and models to study diseases. Covalent modification of the purine and pyrimidine bases is an important strategy for the synthesis of these adducts. Palladium-catalyzed cross-coupling is a powerful method to attach groups to the base heterocycles through the formation of new carbon-carbon and carbon-heteroatom bonds. In this review, approaches to palladium-catalyzed modification of unprotected nucleosides, nucleotides, and oligonucleotides are reviewed. Polar reaction media, such as water or polar aprotic solvents, allow reactions to be performed directly on the hydrophilic nucleosides and nucleotides without the need to use protecting groups. Homogeneous aqueous-phase coupling reactions catalyzed by palladium complexes of water-soluble ligands provide a general approach to the synthesis of modified nucleosides, nucleotides, and oligonucleotides. Full article

(This article belongs to the Special Issue Nucleoside Modifications)

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2199 KiB

Open AccessArticle

Cellular Structural Changes in Candida albicans Caused by the Hydroalcoholic Extract from Sapindus saponaria L.

by Cristiane S. Shinobu-Mesquita, Patricia S. Bonfim-Mendonça, Amanda L. Moreira, Izabel C. P. Ferreira, Lucelia Donatti, Adriana Fiorini and Terezinha I. E. Svidzinski

Molecules 2015, 20(5), 9405-9418; https://doi.org/10.3390/molecules20059405 - 22 May 2015

Cited by 18 | Viewed by 8387

Abstract

Vulvovaginal candidiasis (VVC) is a disease caused by the abnormal growth of yeast-like fungi in the mucosa of the female genital tract. Candida albicans is the principal etiological agent involved in VVC, but reports have shown an increase in the prevalence of Candida [...] Read more.

Vulvovaginal candidiasis (VVC) is a disease caused by the abnormal growth of yeast-like fungi in the mucosa of the female genital tract. Candida albicans is the principal etiological agent involved in VVC, but reports have shown an increase in the prevalence of Candida non-C. albicans (CNCA) cases, which complicates VVC treatment because CNCA does not respond well to antifungal therapy. Our group has reported the in vitro antifungal activity of extracts from Sapindus saponaria L. The present study used scanning electron microscopy and transmission electron microscopy to further evaluate the antifungal activity of hydroalcoholic extract from S. saponaria (HE) against yeast obtained from VVC and structural changes induced by HE. We observed the antifungal activity of HE against 125 vaginal yeasts that belonged to four different species of the Candida genus and S. cerevisae. The results suggest that saponins that are present in HE act on the cell wall or membrane of yeast at the first moments after contact, causing damage to these structures and cell lysis. Full article

(This article belongs to the Section Natural Products Chemistry)

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795 KiB

Open AccessCommunication

Synthesis and Biological Evaluation of Novel Water-Soluble Poly-(ethylene glycol)-10-hydroxycamptothecin Conjugates

by Na Guo, Du Jiang, Luyao Wang, Xing You, Yu-Ou Teng and Peng Yu

Molecules 2015, 20(5), 9393-9404; https://doi.org/10.3390/molecules20059393 - 21 May 2015

Cited by 4 | Viewed by 8834

Abstract

In order to improve the antitumor activity and water solubility of 10-hydroxycamptothecin (HCPT), a series of novel HCPT conjugates were designed and synthesized by conjugating polyethylene glycol (PEG) to the 10-hydroxyl group of HCPT via a valine spacer. The in vitro stability of [...] Read more.

In order to improve the antitumor activity and water solubility of 10-hydroxycamptothecin (HCPT), a series of novel HCPT conjugates were designed and synthesized by conjugating polyethylene glycol (PEG) to the 10-hydroxyl group of HCPT via a valine spacer. The in vitro stability of these synthesized compounds was determined in pH 7.4 buffer at 37 °C, and the results showed that they released HCPT at different rates. All the compounds demonstrated significant antitumor activity in vitro against K562, HepG2 and HT-29 cells. Among them, compounds, 4a, 4d, 4e and 4f, exhibited 2–5 times higher potency than HCPT. The stability and antitumor activity of these conjugates were found to be closely related to the length of PEG and the linker type, conjugates with a relatively short PEG chain and carbamate linkages (compounds 4a and 4f) exhibited controlled release of HCPT and excellent antitumor in vitro activity. Full article

(This article belongs to the Collection Efficient Pharmaceutical and Chemical Approaches for Anticancer Therapy: Design, Preliminary Evaluations, and Further Developments)

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716 KiB

Open AccessArticle

Chemical Composition and Antioxidant Activity of Essential Oil of Six Pinus Taxa Native to China

by Qing Xie, Zhihong Liu and Zhouqi Li

Molecules 2015, 20(5), 9380-9392; https://doi.org/10.3390/molecules20059380 - 21 May 2015

Cited by 44 | Viewed by 7839

Abstract

The essential oils obtained by steam distillation from needles of six China endemic Pinus taxa (P. tabulaeformis, P. tabulaeformis f. shekanensis, P. tabulaeformis var. mukdensis, P. tabulaeformis var. umbraculifera, P. henryi and P [...] Read more.

The essential oils obtained by steam distillation from needles of six China endemic Pinus taxa (P. tabulaeformis, P. tabulaeformis f. shekanensis, P. tabulaeformis var. mukdensis, P. tabulaeformis var. umbraculifera, P. henryi and P. massoniana) were analysed by GC/MS. A total of 72 components were separated and identified by GC/MS from the six taxa. The major constituents of the essential oils were: α-pinene (6.78%–20.55%), bornyl acetale (3.32%–12.71%), β-caryophellene (18.26%–26.31%), α-guaiene (1.23%–8.19%), and germacrene D (1.26%–9.93%). Moreover, the essential oils were evaluated for antioxidant potential by three assays (DPPH, FRAP and ABTS) and tested for their total phenolic content. The results showed that all essential oils exhibited acceptable antioxidant activities and these strongly suggest that these pine needles may serve as a potential source of natural antioxidants for food and medical purposes. Full article

(This article belongs to the Collection Recent Advances in Flavors and Fragrances)

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Open AccessReview

Green Polymer Chemistry: Enzyme Catalysis for Polymer Functionalization

by Sanghamitra Sen and Judit E. Puskas

Molecules 2015, 20(5), 9358-9379; https://doi.org/10.3390/molecules20059358 - 21 May 2015

Cited by 62 | Viewed by 12017

Abstract

Enzyme catalyzed reactions are green alternative approaches to functionalize polymers compared to conventional methods. This technique is especially advantageous due to the high selectivity, high efficiency, milder reaction conditions, and recyclability of enzymes. Selected reactions can be conducted under solventless conditions without the [...] Read more.

Enzyme catalyzed reactions are green alternative approaches to functionalize polymers compared to conventional methods. This technique is especially advantageous due to the high selectivity, high efficiency, milder reaction conditions, and recyclability of enzymes. Selected reactions can be conducted under solventless conditions without the application of metal catalysts. Hence this process is becoming more recognized in the arena of biomedical applications, as the toxicity created by solvents and metal catalyst residues can be completely avoided. In this review we will discuss fundamental aspects of chemical reactions biocatalyzed by Candida antarctica lipase B, and their application to create new functionalized polymers, including the regio- and chemoselectivity of the reactions. Full article

(This article belongs to the Special Issue Enzyme-Catalyzed Reactions)

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Open AccessArticle

Essential Oil from Berries of Lebanese Juniperus excelsa M. Bieb Displays Similar Antibacterial Activity to Chlorhexidine but Higher Cytocompatibility with Human Oral Primary Cells

by Barbara Azzimonti, Andrea Cochis, Marc El Beyrouthy, Marcello Iriti, Francesca Uberti, Rita Sorrentino, Manuela Miriam Landini, Lia Rimondini and Elena Maria Varoni

Molecules 2015, 20(5), 9344-9357; https://doi.org/10.3390/molecules20059344 - 21 May 2015

Cited by 53 | Viewed by 8578

Abstract

Chlorhexidine (CHX), one of the most effective drugs administered for periodontal treatment, presents collateral effects including toxicity when used for prolonged periods; here, we have evaluated the bactericidal potency and the cytocompatibility of Juniperus excelsa M. Bieb essential oil (EO) in comparison with [...] Read more.

Chlorhexidine (CHX), one of the most effective drugs administered for periodontal treatment, presents collateral effects including toxicity when used for prolonged periods; here, we have evaluated the bactericidal potency and the cytocompatibility of Juniperus excelsa M. Bieb essential oil (EO) in comparison with 0.05% CHX. The EO was extracted from berries by hydrodistillation and components identified by gas chromatography and mass spectrometry. Bacterial inhibition halo analysis, quantitative cell viability 2,3-bis(2-methoxy-4-nitro-5-sulphophenyl)-5-[(phenyl amino) carbonyl]-2H-tetrazolium hydroxide assay (XTT), and colony forming unit (CFU) count were evaluated against the two biofilm formers Aggregatibacter actinomycetemcomitans and Streptococcus mutans. Finally, cytocompatibility was assessed with human primary gingival fibroblasts (HGF) and mucosal keratinocytes (HK). The resulting EO was mainly composed of monoterpene hydrocarbons and oxygenated monoterpenes. An inhibition halo test demonstrated that both bacteria were sensitive to the EO; XTT analysis and CFU counts confirmed that 10-fold-diluted EO determined a statistically significant (p < 0.05) reduction in bacteria count and viability towards both biofilm and planktonic forms in a comparable manner to those obtained with CHX. Moreover, EO displayed higher cytocompatibility than CHX (p < 0.05). In conclusion, EO exhibited bactericidal activity similar to CHX, but a superior cytocompatibility, making it a promising antiseptic alternative to CHX. Full article

(This article belongs to the Collection Phytochemicals: Biosynthesis, Metabolism and Biological Activities)

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1261 KiB

Open AccessReview

Complex Interplay of Hormonal Signals during Grape Berry Ripening

by Ana Margarida Fortes, Rita Teresa Teixeira and Patricia Agudelo-Romero

Molecules 2015, 20(5), 9326-9343; https://doi.org/10.3390/molecules20059326 - 21 May 2015

Cited by 118 | Viewed by 13273

Abstract

Grape and wine production and quality is extremely dependent on the fruit ripening process. Sensory and nutritional characteristics are important aspects for consumers and their development during fruit ripening involves complex hormonal control. In this review, we explored data already published on grape [...] Read more.

Grape and wine production and quality is extremely dependent on the fruit ripening process. Sensory and nutritional characteristics are important aspects for consumers and their development during fruit ripening involves complex hormonal control. In this review, we explored data already published on grape ripening and compared it with the hormonal regulation of ripening of other climacteric and non-climacteric fruits. The roles of abscisic acid, ethylene, and brassinosteroids as promoters of ripening are discussed, as well as the role of auxins, cytokinins, gibberellins, jasmonates, and polyamines as inhibitors of ripening. In particular, the recently described role of polyamine catabolism in grape ripening is discussed, together with its putative interaction with other hormones. Furthermore, other recent examples of cross-talk among the different hormones are presented, revealing a complex interplay of signals during grape development and ripening. Full article

(This article belongs to the Collection Wine Chemistry)

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807 KiB

Open AccessArticle

Synthesis, Structural Characterization and Biological Activity of Novel Cyclohexane-1,3-dione Ligands and Their Metal Complexes

by Nevin Turan, Hanifi Körkoca, Ragıp Adigüzel, Naki Çolak and Kenan Buldurun

Molecules 2015, 20(5), 9309-9325; https://doi.org/10.3390/molecules20059309 - 21 May 2015

Cited by 15 | Viewed by 6367

Abstract

Some new Zn(II) and Cu(II) complexes [Cu(L¹)(OAc)₂]∙H₂O, [Cu(L¹)(NO₃)H₂O]∙NO₃∙3.5H₂O, [Zn(L¹)(NO₃)₂]∙4.5H₂O, [Zn(L¹)(OAc)₂(H₂O)₂]∙3H₂ [...] Read more.

Some new Zn(II) and Cu(II) complexes [Cu(L¹)(OAc)₂]∙H₂O, [Cu(L¹)(NO₃)H₂O]∙NO₃∙3.5H₂O, [Zn(L¹)(NO₃)₂]∙4.5H₂O, [Zn(L¹)(OAc)₂(H₂O)₂]∙3H₂O, [Cu₂(L²)(OAc)₄]∙2H₂O∙2DMF, [Cu(L²)₂]∙2NO₃∙1.5DMF∙H₂O, [Zn(L²)₂(NO₃)₂]∙DMF and [Zn₂(L²)(OAc)₄(H₂O)₄]∙5H₂O; L¹ = 2-[2-(2-methoxyphenyl)hydrazono]cyclohexane-1,3-dione and L² = 2-[2-(3-nitrophenyl)hydrazono]cyclohexane-1,3-dione were synthesized and characterized by IR, ¹H-NMR,¹³C-NMR and ultraviolet (UV-Vis.) spectroscopy, elemental analysis, magnetic susceptibility, mass spectrometry and thermogravimetry-differential thermal analysis (TGA-DTA). The synthesized ligands and their complexes were tested for antibacterial activity against Escherichia coli ATCC 25922, Enterococcus faecalis ATCC 29212, Staphylococcus aureus ATCC 25923, and Salmonella typhimurium CCM 583. Some of complexes showed medium-level antibacterial activity against the test bacteria compared with ampicillin. Full article

(This article belongs to the Section Organic Chemistry)

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Open AccessArticle

Comparisons of the Pharmacokinetic Profile of Four Bioactive Components after Oral Administration of Gan-Sui-Ban-Xia Decoction Plus-Minus Gansui and Gancao Drug Combination in Normal Rats

by Yang Zhang, Dawei Qian, Ying Pan, Zhenghua Zhu, Jing Huang, Junzuan Xi, Jianming Guo, Xueping Zhou, Gansheng Zhong and Jinao Duan

Molecules 2015, 20(5), 9295-9308; https://doi.org/10.3390/molecules20059295 - 20 May 2015

Cited by 13 | Viewed by 6573

Abstract

Gan-Sui-Ban-Xia Decoction (GSBXD) was first presented by Zhang Zhongjing in the book Synopsis of Golden Chamber during the Han Dynasty period. The formula was then used for the treatment of persistent fluid retention with floating pulse in Traditional Chinese Medicine (TCM), which in [...] Read more.

Gan-Sui-Ban-Xia Decoction (GSBXD) was first presented by Zhang Zhongjing in the book Synopsis of Golden Chamber during the Han Dynasty period. The formula was then used for the treatment of persistent fluid retention with floating pulse in Traditional Chinese Medicine (TCM), which in modern medicine is known as malignant ascites. Here, a rapid liquid chromatography-tandem mass spectrometry (LC-MS/MS) method has been developed for the determination of glycyrrhizinic acid, liquiritin, paeoniflorin, albiflorin after oral administration of GSBXD plus-minus Gansui and Gancao anti-drug combination to investigate the possible pharmacokinetic profile differences of different prescriptions with GSBXD in normal rats. The differences of pharmacokinetic parameters among groups were tested by the Student’s t-test with p < 0.05 as the level of significance. Significant differences were found between the Gansui and Gancao anti-drug combination and other herbs in GSBXD on pharmacokinetic profile of glycyrrhizinic acid, liquiritin, paeoniflorin and albiflorin. The obtained knowledge might contribute to the rationality of the clinic use of GSBXD and also reveal the compatibility conditions of the Gansui and Gancao anti-drug combination. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessReview

Recent Advances in Click Chemistry Applied to Dendrimer Synthesis

by Mathieu Arseneault, Caroline Wafer and Jean-François Morin

Molecules 2015, 20(5), 9263-9294; https://doi.org/10.3390/molecules20059263 - 20 May 2015

Cited by 132 | Viewed by 18499

Abstract

Dendrimers are monodisperse polymers grown in a fractal manner from a central point. They are poised to become the cornerstone of nanoscale devices in several fields, ranging from biomedicine to light-harvesting. Technical difficulties in obtaining these molecules has slowed their transfer from academia [...] Read more.

Dendrimers are monodisperse polymers grown in a fractal manner from a central point. They are poised to become the cornerstone of nanoscale devices in several fields, ranging from biomedicine to light-harvesting. Technical difficulties in obtaining these molecules has slowed their transfer from academia to industry. In 2001, the arrival of the “click chemistry” concept gave the field a major boost. The flagship reaction, a modified Hüisgen cycloaddition, allowed researchers greater freedom in designing and building dendrimers. In the last five years, advances in click chemistry saw a wider use of other click reactions and a notable increase in the complexity of the reported structures. This review covers key developments in the click chemistry field applied to dendrimer synthesis from 2010 to 2015. Even though this is an expert review, basic notions and references have been included to help newcomers to the field. Full article

(This article belongs to the Collection Advances in Click Chemistry)

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1989 KiB

Open AccessArticle

Caffeic Acid Phenethyl Ester and Ethanol Extract of Propolis Induce the Complementary Cytotoxic Effect on Triple-Negative Breast Cancer Cell Lines

by Anna Rzepecka-Stojko, Agata Kabała-Dzik, Aleksandra Moździerz, Robert Kubina, Robert D. Wojtyczka, Rafał Stojko, Arkadiusz Dziedzic, Żaneta Jastrzębska-Stojko, Magdalena Jurzak, Ewa Buszman and Jerzy Stojko

Molecules 2015, 20(5), 9242-9262; https://doi.org/10.3390/molecules20059242 - 20 May 2015

Cited by 60 | Viewed by 10415

Abstract

Chemotherapy of breast cancer could be improved by bioactive natural substances, which may potentially sensitize the carcinoma cells’ susceptibility to drugs. Numerous phytochemicals, including propolis, have been reported to interfere with the viability of carcinoma cells. We evaluated the in vitro cytotoxic activity [...] Read more.

Chemotherapy of breast cancer could be improved by bioactive natural substances, which may potentially sensitize the carcinoma cells’ susceptibility to drugs. Numerous phytochemicals, including propolis, have been reported to interfere with the viability of carcinoma cells. We evaluated the in vitro cytotoxic activity of ethanol extract of propolis (EEP) and its derivative caffeic acid phenethyl ester (CAPE) towards two triple-negative breast cancer (TNBC) cell lines, MDA-MB-231 and Hs578T, by implementation of the MTT and lactate dehydrogenase (LDH) assays. The morphological changes of breast carcinoma cells were observed following exposure to EEP and CAPE. The IC₅₀ of EEP was 48.35 µg∙mL⁻¹ for MDA-MB-23 cells and 33.68 µg∙mL⁻¹ for Hs578T cells, whereas the CAPE IC₅₀ was 14.08 µM and 8.01 µM for the MDA-MB-231 and Hs578T cell line, respectively. Here, we report that propolis and CAPE inhibited the growth of the MDA-MB-231 and Hs578T lines in a dose-dependent and exposure time-dependent manner. EEP showed less cytotoxic activity against both types of TNBC cells. EEP and, particularly, CAPE may markedly affect the viability of breast cancer cells, suggesting the potential role of bioactive compounds in chemoprevention/chemotherapy by potentiating the action of standard anti-cancer drugs. Full article

(This article belongs to the Collection Phytochemicals: Biosynthesis, Metabolism and Biological Activities)

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Open AccessArticle

Synthesis and Biological Evaluation of Hydrazone Derivatives as Antifungal Agents

by Bruna B. Casanova, Mauro N. Muniz, Thayse De Oliveira, Luís Flavio De Oliveira, Michel M. Machado, Alexandre M. Fuentefria, Grace Gosmann and Simone C. B. Gnoatto

Molecules 2015, 20(5), 9229-9241; https://doi.org/10.3390/molecules20059229 - 20 May 2015

Cited by 27 | Viewed by 7932

Abstract

Emerging yeasts are among the most prevalent causes of systemic infections with high mortality rates and there is an urgent need to develop specific, effective and non-toxic antifungal agents to respond to this issue. In this study 35 aldehydes, hydrazones and hydrazines were [...] Read more.

Emerging yeasts are among the most prevalent causes of systemic infections with high mortality rates and there is an urgent need to develop specific, effective and non-toxic antifungal agents to respond to this issue. In this study 35 aldehydes, hydrazones and hydrazines were obtained and their antifungal activity was evaluated against Candida species (C. parapsilosis, C. tropicalis, C. krusei, C. albicans, C. glabrata and C. lusitaneae) and Trichosporon asahii, in an in vitro screening. The minimum inhibitory concentrations (MICs) of the active compounds in the screening was determined against 10 clinical isolates of C. parapsilosis and 10 of T. asahii. The compounds 4-pyridin-2-ylbenzaldehyde] (13a) and tert-butyl-(2Z)-2-(3,4,5-trihydroxybenzylidine)hydrazine carboxylate (7b) showed the most promising MIC values in the range of 16–32 μg/mL and 8–16 μg/mL, respectively. The compounds’ action on the stability of the cell membrane and cell wall was evaluated, which suggested the action of the compounds on the fungal cell membrane. Cell viability of leukocytes and an alkaline comet assay were performed to evaluate the cytotoxicity. Compound 13a was not cytotoxic at the active concentrations. These results support the discovery of promising candidates for the development of new antifungal agents. Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessArticle

Aromatic Amino Acids-Guanidinium Complexes through Cation-π Interactions

by Cristina Trujillo, Ana A. Rodriguez-Sanz and Isabel Rozas

Molecules 2015, 20(5), 9214-9228; https://doi.org/10.3390/molecules20059214 - 20 May 2015

Cited by 11 | Viewed by 9508

Abstract

Continuing with our interest in the guanidinium group and the different interactions than can establish, we have carried out a theoretical study of the complexes formed by this cation and the aromatic amino acids (phenylalanine, histidine, tryptophan and tyrosine) using DFT methods and [...] Read more.

Continuing with our interest in the guanidinium group and the different interactions than can establish, we have carried out a theoretical study of the complexes formed by this cation and the aromatic amino acids (phenylalanine, histidine, tryptophan and tyrosine) using DFT methods and PCM-water solvation. Both hydrogen bonds and cation-π interactions have been found upon complexation. These interactions have been characterized by means of the analysis of the molecular electron density using the Atoms-in-Molecules approach as well as the orbital interactions using the Natural Bond Orbital methodology. Finally, the effect that the cation-π and hydrogen bond interactions exert on the aromaticity of the corresponding amino acids has been evaluated by calculating the theoretical NICS values, finding that the aromatic character was not heavily modified upon complexation. Full article

(This article belongs to the Special Issue Noncovalent pi-Interactions)

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Open AccessReview

Curcumin, Inflammation, and Chronic Diseases: How Are They Linked?

by Yan He, Yuan Yue, Xi Zheng, Kun Zhang, Shaohua Chen and Zhiyun Du

Molecules 2015, 20(5), 9183-9213; https://doi.org/10.3390/molecules20059183 - 20 May 2015

Cited by 436 | Viewed by 66642

Abstract

It is extensively verified that continued oxidative stress and oxidative damage may lead to chronic inflammation, which in turn can mediate most chronic diseases including cancer, diabetes, cardiovascular, neurological, inflammatory bowel disease and pulmonary diseases. Curcumin, a yellow coloring agent extracted from turmeric, [...] Read more.

It is extensively verified that continued oxidative stress and oxidative damage may lead to chronic inflammation, which in turn can mediate most chronic diseases including cancer, diabetes, cardiovascular, neurological, inflammatory bowel disease and pulmonary diseases. Curcumin, a yellow coloring agent extracted from turmeric, shows strong anti-oxidative and anti-inflammatory activities when used as a remedy for the prevention and treatment of chronic diseases. How oxidative stress activates inflammatory pathways leading to the progression of chronic diseases is the focus of this review. Thus, research to date suggests that chronic inflammation, oxidative stress, and most chronic diseases are closely linked, and the antioxidant properties of curcumin can play a key role in the prevention and treatment of chronic inflammation diseases. Full article

(This article belongs to the Special Issue Curcumin, Inflammation, and Chronic Diseases: How are They Linked?)

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Open AccessArticle

Predicting the Composition of Red Wine Blends Using an Array of Multicomponent Peptide-Based Sensors

by Eman Ghanem, Helene Hopfer, Andrea Navarro, Maxwell S. Ritzer, Lina Mahmood, Morgan Fredell, Ashley Cubley, Jessica Bolen, Rabia Fattah, Katherine Teasdale, Linh Lieu, Tedmund Chua, Federico Marini, Hildegarde Heymann and Eric V. Anslyn

Molecules 2015, 20(5), 9170-9182; https://doi.org/10.3390/molecules20059170 - 20 May 2015

Cited by 25 | Viewed by 12533

Abstract

Differential sensing using synthetic receptors as mimics of the mammalian senses of taste and smell is a powerful approach for the analysis of complex mixtures. Herein, we report on the effectiveness of a cross-reactive, supramolecular, peptide-based sensing array in differentiating and predicting the [...] Read more.

Differential sensing using synthetic receptors as mimics of the mammalian senses of taste and smell is a powerful approach for the analysis of complex mixtures. Herein, we report on the effectiveness of a cross-reactive, supramolecular, peptide-based sensing array in differentiating and predicting the composition of red wine blends. Fifteen blends of Cabernet Sauvignon, Merlot and Cabernet Franc, in addition to the mono varietals, were used in this investigation. Linear Discriminant Analysis (LDA) showed a clear differentiation of blends based on tannin concentration and composition where certain mono varietals like Cabernet Sauvignon seemed to contribute less to the overall characteristics of the blend. Partial Least Squares (PLS) Regression and cross validation were used to build a predictive model for the responses of the receptors to eleven binary blends and the three mono varietals. The optimized model was later used to predict the percentage of each mono varietal in an independent test set composted of four tri-blends with a 15% average error. A partial least square regression model using the mouth-feel and taste descriptive sensory attributes of the wine blends revealed a strong correlation of the receptors to perceived astringency, which is indicative of selective binding to polyphenols in wine. Full article

(This article belongs to the Collection Wine Chemistry)

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Open AccessArticle

Characterization of Anthocyanins in Perilla frutescens var. acuta Extract by Advanced UPLC-ESI-IT-TOF-MSⁿ Method and Their Anticancer Bioactivity

by Yan-Kang He, You-Yuan Yao and Ya-Ning Chang

Molecules 2015, 20(5), 9155-9169; https://doi.org/10.3390/molecules20059155 - 19 May 2015

Cited by 44 | Viewed by 8690

Abstract

The anthocyanin extract from a domestic Perilla cultivar (Perilla frutescens var. acuta) were isolated and characterized with high mass accuracy and multi-dimensional fragmentation by means of ultra-performance liquid chromatography (UPLC) and electrospray ionization-ion trap-time of flight mass spectrometry analysis (ESI-IT-TOF-MSⁿ [...] Read more.

The anthocyanin extract from a domestic Perilla cultivar (Perilla frutescens var. acuta) were isolated and characterized with high mass accuracy and multi-dimensional fragmentation by means of ultra-performance liquid chromatography (UPLC) and electrospray ionization-ion trap-time of flight mass spectrometry analysis (ESI-IT-TOF-MSⁿ). The new developed and applied LC-MS method focused on in-depth screening of anthocyanin compounds with similar structures which also provided a new approach of anthocyanin characterization without the use of external standards. Selective detection of interested anthocyanins was achieved utilizing extracted ion chromatogram (EIC) analysis, while MSⁿ spectra were recorded to allow identification of the anthocyanin based on characteristic fragmentation patterns. Seven anthocyanins including one feruloyl (Cyanidin 3-O-feruloylglucoside-5-O-glucoside), two caffeoyl (Cyanidin 3-O-caffeoylglucoside-5-O-glucoside, Cyanidin 3-O-caffeoylglucoside-5-O-malonylglucoside) and four coumaroyl substituted anthocyanins (Cis-shisonin, Malonyl-cis-shisonin, Shisonin, and Malonyl-shisonin) were identified. Annexin-V FITC/PI flow cytometric assay was performed to analyze the influence of anthocyanin extract of P. frutescens var. acuta on cell apoptosis. The results suggested that Perilla anthocyanins can induce Hela cell apoptosis by a dose dependent manner. Full article

(This article belongs to the Special Issue New Technologies for the Recovery of Natural Products)

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Open AccessReview

Nanofibers of Cellulose and Its Derivatives Fabricated Using Direct Electrospinning

by Kousaku Ohkawa

Molecules 2015, 20(5), 9139-9154; https://doi.org/10.3390/molecules20059139 - 19 May 2015

Cited by 70 | Viewed by 9328

Abstract

A short review with 49 references describes the electrospinninng (ES) process for polysaccharides, cellulose and chitosan, and their derivatives, including cellulose acetate and hydroxypropyl cellulose. A majority of applied studies adopted a two step-process, in which the cellulose acetate was used for the [...] Read more.

A short review with 49 references describes the electrospinninng (ES) process for polysaccharides, cellulose and chitosan, and their derivatives, including cellulose acetate and hydroxypropyl cellulose. A majority of applied studies adopted a two step-process, in which the cellulose acetate was used for the first ES process, followed by acetyl group removal to regenerate cellulose thin fibers. The electrospun nonwoven fabrics (ESNW) of regenerated cellulose can be modified by introduction of aldehyde groups by oxidative cleavage of vicinal diols using periodates, and these aldehyde groups serve as acceptors of foreign substances, with various chemical/biological functions, to be immobilized on the fiber surfaces in the ESNW matrices. Direct electrospinning of cellulose from trifluroacetic acid solution was also developed and the applied studies were summarized to conclude the current trends of interests in the ES and related technologies. Full article

(This article belongs to the Special Issue New Trends in Cellulose and Chitin Chemistry)

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Open AccessArticle

1,3-Diphenylethenylcarbazolyl-Based Monomer for Cross-Linked Hole Transporting Layers

by Maryte Daskeviciene, Giedre Bubniene, Tadas Malinauskas, Vygintas Jankauskas, Valentas Gaidelis, Valdas Paulauskas and Vytautas Getautis

Molecules 2015, 20(5), 9124-9138; https://doi.org/10.3390/molecules20059124 - 19 May 2015

Cited by 1 | Viewed by 5032

Abstract

A new cross-linkable monomer containing 1,3-diphenylethenylcarbazolyl-based hole-transporting moieties and four reactive epoxy groups, was prepared by a multistep synthesis route from 1,3-bis(2,2-diphenylethenyl)-9H-carbazol-2-ol and its application for the in situ formation of cross-linked hole transporting layers was investigated. A high concentration of [...] Read more.

A new cross-linkable monomer containing 1,3-diphenylethenylcarbazolyl-based hole-transporting moieties and four reactive epoxy groups, was prepared by a multistep synthesis route from 1,3-bis(2,2-diphenylethenyl)-9H-carbazol-2-ol and its application for the in situ formation of cross-linked hole transporting layers was investigated. A high concentration of flexible aliphatic epoxy chains ensures good solubility and makes this compound an attractive cross-linking agent. The synthesized compounds were characterized by various techniques, including differential scanning calorimetry, xerographic time of flight, and electron photoemission in air methods. Full article

(This article belongs to the Section Organic Chemistry)

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Open AccessReview

Gaseous Mediators Nitric Oxide and Hydrogen Sulfide in the Mechanism of Gastrointestinal Integrity, Protection and Ulcer Healing

by Marcin Magierowski, Katarzyna Magierowska, Slawomir Kwiecien and Tomasz Brzozowski

Molecules 2015, 20(5), 9099-9123; https://doi.org/10.3390/molecules20059099 - 19 May 2015

Cited by 97 | Viewed by 12770

Abstract

Nitric oxide (NO) and hydrogen sulfide (H₂S) are known as biological messengers; they play an important role in human organism and contribute to many physiological and pathophysiological processes. NO is produced from l-arginine by constitutive NO synthase (NOS) and inducible NOS [...] Read more.

Nitric oxide (NO) and hydrogen sulfide (H₂S) are known as biological messengers; they play an important role in human organism and contribute to many physiological and pathophysiological processes. NO is produced from l-arginine by constitutive NO synthase (NOS) and inducible NOS enzymatic pathways. This gaseous mediator inhibits platelet aggregation, leukocyte adhesion and contributes to the vessel homeostasis. NO is known as a vasodilatory molecule involved in control of the gastric blood flow (GBF) and the maintenance of gastric mucosal barrier integrity in either healthy gastric mucosa or that damaged by strong irritants. Biosynthesis of H₂S in mammals depends upon two enzymes cystathionine-β-synthase and cystathionine γ-lyase. This gaseous mediator, similarly to NO and carbon monoxide, is involved in neuromodulation, vascular contractility and anti-inflammatory activities. For decades, H₂S has been known to inhibit cytochrome c oxidase and reduce cell energy production. Nowadays it is generally considered to act through vascular smooth muscle ATP-dependent K⁺ channels, interacting with intracellular transcription factors and promote sulfhydration of protein cysteine moieties within the cell, but the mechanism of potential gastroprotective and ulcer healing properties of H₂S has not been fully explained. The aim of this review is to compare current results of the studies concerning the role of H₂S and NO in gastric mucosa protection and outline areas that may pose new opportunities for further development of novel therapeutic targets. Full article

(This article belongs to the Special Issue Nitric Oxide (NO) Release Chemistry)

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Open AccessArticle

LC-MS/MS Determination and Pharmacokinetic Study of Pedunculoside in Rat Plasma after Oral Administration of Pedunculoside and Ilex rotunda Extract

by Waiou Zhao, Li Pang, Dahai Xu and Nan Zhang

Molecules 2015, 20(5), 9084-9098; https://doi.org/10.3390/molecules20059084 - 19 May 2015

Cited by 14 | Viewed by 6534

Abstract

Ilex rotunda is widely used to treat many disorders as a traditional Chinese medicine (TCM) containing 4%–5% pedunculoside (PDC). A rapid, selective, and sensitive liquid chromatography-tandem mass spectrometry method (LC-MS/MS) was developed and validated to determine PDC in rat plasma by using 3β,19α-dihydroxyurs-12-en-28-oic [...] Read more.

Ilex rotunda is widely used to treat many disorders as a traditional Chinese medicine (TCM) containing 4%–5% pedunculoside (PDC). A rapid, selective, and sensitive liquid chromatography-tandem mass spectrometry method (LC-MS/MS) was developed and validated to determine PDC in rat plasma by using 3β,19α-dihydroxyurs-12-en-28-oic acid 28-β-D-glucopyranosyl ester (DEOG) as an internal standard. The analytes were extracted by protein precipitation and eluted on a C₁₈ chromatography column using a mobile phase of methanol–H₂O (70:30, v/v) delivered at a flow rate of 0.6 mL/min. Detection was performed using positive ion electrospray ionization in multiple reaction monitoring modes. The assay was linear over the concentration range of 0.60 ng/mL to 200 ng/mL, with a quantification limit of 0.60 ng/mL. Intra-day and inter-day precisions (%RSD) ranged from 2.12 to 9.51 for PDC, whereas the accuracy was within −7.83%~9.40%. The validated method was successfully applied to the pharmacokinetic study of PDC in rat plasma after oral administration of pure PDC and Ilex rotunda extract (IRE). Pharmacokinetic parameters of PDC in IRE, such as C_max, AUC_0–t, AUC_0–∞, t_1/2z_, and CL_z/F, statistically differed from those of the pure monomer (p < 0.01). However, T_max and MRT showed no significant differences between the two groups. Results suggested that other coexisting components in IRE may decrease the absorption of PDC. Compound-compound interactions between PDC and other herbal extract components can alter the pharmacokinetic behavior of PDC. The study will be helpful in providing references for understanding the action mechanism and clinical application of Ilex rotunda. Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessArticle

Four New Triterpenoids from Callicarpa kwangtungensis

by Guo-Ping Zhou, Yan Yu, Ming-Ming Yuan, Tengfei Ji, Hui-Zheng Fu and Rui-Jian Zhong

Molecules 2015, 20(5), 9071-9083; https://doi.org/10.3390/molecules20059071 - 19 May 2015

Cited by 22 | Viewed by 5232

Abstract

Four new triterpenoids which were identifed as 2α,3β,6β,19α-tetrahydroxy- oleanolic acid 28-O-β-D-glucopyranoside (1), 2-O-β-D-glucopyranosyloxy-3α,19α-di-hydroxyoleanolic acid (2), 2-O-β-D-glucopyranosyloxy-3α,19α-dihydroxyursolic acid (3), 2α,3α,6β,19α-tetrahydroxyursolic acid 28-O-β-D-glucopyranoside (4), were isolated from the aerial [...] Read more.

Four new triterpenoids which were identifed as 2α,3β,6β,19α-tetrahydroxy- oleanolic acid 28-O-β-D-glucopyranoside (1), 2-O-β-D-glucopyranosyloxy-3α,19α-di-hydroxyoleanolic acid (2), 2-O-β-D-glucopyranosyloxy-3α,19α-dihydroxyursolic acid (3), 2α,3α,6β,19α-tetrahydroxyursolic acid 28-O-β-D-glucopyranoside (4), were isolated from the aerial parts of Callicarpa kwangtungensis together with three known triterpenoids identified as 2α,3β,21β-trihydroxyursolic acid 28-O-β-D-glucopyranoside (5), 2α,3α,19α,23-tetrahydroxyoleanolic acid 28-O-β-D-glucopyranoside (6), 2α,3α,19α,23-tetrahydroxyursolic acid 28-O-β-D-glucopyranoside (7). Their structures were elucidated by the combination of mass spectrometry (MS), one and two-dimensional NMR experiments. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Effects of Dietary Brazilian Palm Oil (Mauritia flexuosa L.) on Cholesterol Profile and Vitamin A and E Status of Rats

by Jailane De Souza Aquino, Juliana Késsia Barbosa Soares, Marciane Magnani, Thayza Christina Montenegro Stamford, Robson De Jesus Mascarenhas, Renata Leite Tavares and Tânia Lúcia Montenegro Stamford

Molecules 2015, 20(5), 9054-9070; https://doi.org/10.3390/molecules20059054 - 19 May 2015

Cited by 23 | Viewed by 7465

Abstract

In vitro studies have been carried out to establish the nutritional differences between crude and refined vegetable oils; however, the impact of the consumption of these foods on metabolism, in particular the effect of buriti oil, needs to be further evaluated. The aim [...] Read more.

In vitro studies have been carried out to establish the nutritional differences between crude and refined vegetable oils; however, the impact of the consumption of these foods on metabolism, in particular the effect of buriti oil, needs to be further evaluated. The aim of this study was to evaluate the biochemical and murine parameters and the vitamin A and E status in young rats fed with diets supplemented with crude or refined buriti oil. The animals (n = 30) were randomized into three groups receiving diet added of soybean oil (control), crude buriti oil (CBO) and refined buriti oil (RBO) for 28 days. Rats fed with diet added of refined buriti oil (RBO) showed reduced total cholesterol (up to 60.27%), LDL (64.75%), triglycerides (55.47%) and enzyme aspartate transaminase (21.57%) compared to those fed with diet added of crude oil. Serum and hepatic retinol and tocopherol were higher by two to three times in CBO and RBO groups compared to the control group, but no differences were observed for murine parameters. The results indicate that buriti oil is an important source of the antioxidant vitamins A and E, and refined buriti oil is suggested as alternative to improve the lipid profile of healthy rats. Full article

(This article belongs to the Special Issue Dietary Bioactive Compounds: Metabolism, Mechanisms and Translational Significance for Health and Prevention of Diseases)

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2985 KiB

Open AccessReview

Protein-Carbohydrate Interactions as Part of Plant Defense and Animal Immunity

by Kristof De Schutter and Els J. M. Van Damme

Molecules 2015, 20(5), 9029-9053; https://doi.org/10.3390/molecules20059029 - 19 May 2015

Cited by 86 | Viewed by 13934

Abstract

The immune system consists of a complex network of cells and molecules that interact with each other to initiate the host defense system. Many of these interactions involve specific carbohydrate structures and proteins that specifically recognize and bind them, in particular lectins. It [...] Read more.

The immune system consists of a complex network of cells and molecules that interact with each other to initiate the host defense system. Many of these interactions involve specific carbohydrate structures and proteins that specifically recognize and bind them, in particular lectins. It is well established that lectin-carbohydrate interactions play a major role in the immune system, in that they mediate and regulate several interactions that are part of the immune response. Despite obvious differences between the immune system in animals and plants, there are also striking similarities. In both cases, lectins can play a role as pattern recognition receptors, recognizing the pathogens and initiating the stress response. Although plants do not possess an adaptive immune system, they are able to imprint a stress memory, a mechanism in which lectins can be involved. This review will focus on the role of lectins in the immune system of animals and plants. Full article

(This article belongs to the Special Issue Protein-Carbohydrate Interactions, and Beyond)

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Open AccessArticle

S4MPLE—Sampler for Multiple Protein-Ligand Entities: Methodology and Rigid-Site Docking Benchmarking

by Laurent Hoffer, Camelia Chira, Gilles Marcou, Alexandre Varnek and Dragos Horvath

Molecules 2015, 20(5), 8997-9028; https://doi.org/10.3390/molecules20058997 - 19 May 2015

Cited by 27 | Viewed by 8496

Abstract

This paper describes the development of the unified conformational sampling and docking tool called Sampler for Multiple Protein-Ligand Entities (S4MPLE). The main novelty in S4MPLE is the unified dealing with intra- and intermolecular degrees of freedom (DoF). While classically programs are either designed [...] Read more.

This paper describes the development of the unified conformational sampling and docking tool called Sampler for Multiple Protein-Ligand Entities (S4MPLE). The main novelty in S4MPLE is the unified dealing with intra- and intermolecular degrees of freedom (DoF). While classically programs are either designed for folding or docking, S4MPLE transcends this artificial specialization. It supports folding, docking of a flexible ligand into a flexible site and simultaneous docking of several ligands. The trick behind it is the formal assimilation of inter-molecular to intra-molecular DoF associated to putative inter-molecular contact axes. This is implemented within the genetic operators powering a Lamarckian Genetic Algorithm (GA). Further novelty includes differentiable interaction fingerprints to control population diversity, and fitting a simple continuum solvent model and favorable contact bonus terms to the AMBER/GAFF force field. Novel applications—docking of fragment-like compounds, simultaneous docking of multiple ligands, including free crystallographic waters—were published elsewhere. This paper discusses: (a) methodology, (b) set-up of the force field energy functions and (c) their validation in classical redocking tests. More than 80% success in redocking was achieved (RMSD of top-ranked pose < 2.0 Å). Full article

(This article belongs to the Special Issue Molecular Docking in Drug Design)

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1074 KiB

Open AccessCommunication

Inhibitory Effects of Verrucarin A on Tunicamycin-Induced ER Stress in FaO Rat Liver Cells

by Eun Young Bae, Seung Woong Lee, Sin Seong, Wonjun Cho, Jong Seog Ahn and Hyun-Sug Cho

Molecules 2015, 20(5), 8988-8996; https://doi.org/10.3390/molecules20058988 - 19 May 2015

Cited by 5 | Viewed by 7374

Abstract

Endoplasmic reticulum (ER) stress is linked with development and maintenance of cancer, and serves as a therapeutic target for treatment of cancer. Verrucarin A, isolated from the broth of Fusarium sp. F060190, showed potential inhibitory activity on tunicamycin-induced ER stress in FaO rat [...] Read more.

Endoplasmic reticulum (ER) stress is linked with development and maintenance of cancer, and serves as a therapeutic target for treatment of cancer. Verrucarin A, isolated from the broth of Fusarium sp. F060190, showed potential inhibitory activity on tunicamycin-induced ER stress in FaO rat liver cells. In addition, the compound decreased tunicamycin-induced GRP78 promoter activity in a dose dependent manner without inducing significant inhibition of luciferase activity and cell growth for 6 and 12 h. Moreover, the compound decreased the expression of GRP78, CHOP, XBP-1, and suppressed XBP-1, and reduced phosphorylation of IRE1α in FaO rat liver cells. This evidence suggests for the first time that verrucarin A inhibited tunicamycin-induced ER stress in FaO rat liver cells. Full article

(This article belongs to the Collection Bioactive Compounds)

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Open AccessReview

Chemistry and Biological Activity of Ramalina Lichenized Fungi

by Antônio Sérgio Nascimento Moreira, Raimundo Braz-Filho, Vicente Mussi-Dias and Ivo José Curcino Vieira

Molecules 2015, 20(5), 8952-8987; https://doi.org/10.3390/molecules20058952 - 19 May 2015

Cited by 47 | Viewed by 9870

Abstract

Lichens are a form of symbiont between a fungus and an alga or cyanobacterium, which contains a wide variety of organic compounds with certain secondary metabolite classes typical of these organisms. The Ramalina genus has approximately 246 species distributed around the World, of [...] Read more.

Lichens are a form of symbiont between a fungus and an alga or cyanobacterium, which contains a wide variety of organic compounds with certain secondary metabolite classes typical of these organisms. The Ramalina genus has approximately 246 species distributed around the World, of which in this review approximately 118 species with published chemical or biological activity studies of extracts or isolated compounds were cited. From the 153 mentioned compounds, only 27 passed were tested for biological activity, being usnic acid the most studied compound and the one showing the best results in almost all in vitro tests performed, although other compounds also presented excellent results as antimicrobial, antitumor and anti-inflammatory agents, among others. Extracts of several species also presented significant results in performed biological tests, demonstrating the potential that these organisms have, in particular, the gender Ramalina, to produce bioactive molecules that can be used as a model for the production of pharmaceuticals. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Structural Characteristics and Non-Linear Optical Behaviour of a 2-Hydroxynicotinate-Containing Zinc-Based Metal-Organic Framework

by Shruti Mendiratta, Cheng-Hua Lee, Sih-Ying Lee, Ya-Chuan Kao, Bor-Chen Chang, Yih-Hsing Lo and Kuang-Lieh Lu

Molecules 2015, 20(5), 8941-8951; https://doi.org/10.3390/molecules20058941 - 18 May 2015

Cited by 19 | Viewed by 6370

Abstract

Materials with non-linear optical (NLO) properties play an important role in the construction of electronic devices for optical communications, optical data processing and data storage. With this aim in mind, a Zn(II)-based metal-organic framework {[Zn₂(nica)₂(bpy)_1.5(H₂O)]×0.5(bpy)×3H [...] Read more.

Materials with non-linear optical (NLO) properties play an important role in the construction of electronic devices for optical communications, optical data processing and data storage. With this aim in mind, a Zn(II)-based metal-organic framework {[Zn₂(nica)₂(bpy)_1.5(H₂O)]×0.5(bpy)×3H₂O}_n (1), was synthesized using 4,4ʹ-bipyridine (bpy) and a potentially bidentate ligand, 2-hydroxynicotinic acid (H₂nica) with a salicylate binding moiety. A single-crystal X-ray diffraction analysis revealed that compound 1 crystallized in the orthorhombic space group Fdd2 and was composed of a three dimensional porous framework. Since Fdd2 belonged to a class of non-centrosymmetric space groups, we therefore investigated the non-linear optical behaviour of compound 1. Photoluminescence studies revealed that compound 1 exhibited a blue light emission with a maxima at 457 nm. Full article

(This article belongs to the Special Issue Metal-Organic Frameworks: Chemistry and Applications)

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Open AccessArticle

Absorption and Metabolism Characteristics of Triptolide as Determined by a Sensitive and Reliable LC-MS/MS Method

by Xiaomei Gong, Yan Chen and Yi Wu

Molecules 2015, 20(5), 8928-8940; https://doi.org/10.3390/molecules20058928 - 18 May 2015

Cited by 33 | Viewed by 6350

Abstract

In this research, a sensitive and reliable LC-MS/MS method was developed and applied to determine the concentration of triptolide in rat plasma, microsomes, and cell incubation media. The absolute oral bioavailability of triptolide is 63.9% at a dose of 1 mg·kg⁻¹. [...] Read more.

In this research, a sensitive and reliable LC-MS/MS method was developed and applied to determine the concentration of triptolide in rat plasma, microsomes, and cell incubation media. The absolute oral bioavailability of triptolide is 63.9% at a dose of 1 mg·kg⁻¹. In vitro, the bidirectional transport of triptolide across Caco-2 cells was studied. A markedly higher transport of triptolide across Caco-2 cells was observed in the basolateral-to-apical direction and was abrogated in the presence of the P-gp inhibitor, verapamil. The result indicated that P-gp might be involved in the absorption of triptolide in intestinal. The metabolic stability was also investigated using human liver microsome incubation systems in vitro. In HLMs, incubations with an initial triptolide concentration of 1 μM resulted in an 82.4% loss of substrate over 60 min, and the t_1/2 was 38 min, which indicated that triptolide was easily metabolized in human liver microsomes. In conclusion, the absolute oral bioavailability of triptolide in plasma, transport across Caco-2 cell monolayers, and metabolic stability in human liver microsomes were systematically investigated by using a sensitive and reliable LC-MS/MS method. Full article

(This article belongs to the Section Natural Products Chemistry)

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