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Tao Chen, Hongmei Li, Chen Chen, Lixin Wei, Yulin Li
Large-scale preparation and α-glucosidase inhibitory activity of a specific xanthone swertioside from Swertia mussotii were investigated in this study. Firstly, an efficient method was successfully established by liquid-liquid extraction, preparative high-performance liquid chromatography and sephadex LH-20 for large-scale preparation of swertioside. The recovery of swertioside reached 92.0%. Secondly, in vitro α-glucosidase inhibition experiment showed that swertioside had good inhibition close to acarbose...
March 17, 2017: Journal of Chromatographic Science
Binh T D Trinh, Tam T T Quach, Dung N Bui, Dan Staerk, Lien-Hoa D Nguyen, Anna K Jäger
Three new xanthones, oblongixanthone F-H (1-3), along with eight known xanthones (4-11), were isolated from an EtOAc extract of the twigs of Garcinia oblongifolia. Their structures were elucidated by spectroscopic analysis including 1D- and 2D-NMR spectroscopy and mass spectrometry. The antidiabetic effects of all isolated compounds were evaluated by in vitro α-glucosidase and PTP1B inhibition assays. Compound 11 was the most active compound, and inhibited α-glucosidase and PTP1B with IC50 values of 1.7±0...
March 16, 2017: Fitoterapia
Xue Fei Tan, Zia Uddin, Chanin Park, Yeong Hun Song, Minky Son, Keun Woo Lee, Ki Hun Park
Protein tyrosine phosphatase 1B (PTP1B) plays important role in diabetes, obesity and cancer. The methanol extract of the gum resin of Garcinia hanburyi (G. hanburyi) showed potent PTP1B inhibition at 10µg/ml. The active compounds were identified as prenylated caged xanthones (1-9) which inhibited PTP1B in dose-dependent manner. Carboxybutenyl group within caged motif (A ring) was found to play a critical role in enzyme inhibition such as 1-6 (IC50s=0.47-4.69µM), whereas compounds having hydroxymethylbutenyl 7 (IC50=70...
March 6, 2017: Bioorganic & Medicinal Chemistry
Cherdsak Boonyong, Chutichot Pattamadilok, Rutt Suttisri, Suree Jianmongkol
BACKGROUND: Up-regulation of P-gp is an adaptive survival mechanism of cancer cells from chemotherapy. Three new phytochemicals including two benzophenones, guttiferone K (GK) and oblongifolin C (OC), and a xanthone, isojacaruebin (ISO), are potential anti-cancer agents. However, the capability of these compounds to increase multidrug-resistance (MDR) through P-gp up-regulation in cancer cells has not been reported. PURPOSE: This study was to investigate the effects of GK, OC and ISO on P-gp up-regulation in colorectal adenocarcinoma cells (Caco-2 cells)...
April 15, 2017: Phytomedicine: International Journal of Phytotherapy and Phytopharmacology
Huaming Tao, Xiaoyi Wei, Xiuping Lin, Xuefeng Zhou, Junde Dong, Bin Yang
Two new xanthone derivatives, penixanthones A (1) and B (2), together with three known compounds, aspenicillide (3), 1,5-dihydroxy-3-methoxy-7-methyl-anthracene-9,10-dione (4) and 1,2-indandiol (5), were isolated from the ethyl acetate extract of a culture of the fungus Penicillium sp. SYFz-1, which was separated from a mangrove soil sample. The structures of these compounds were elucidated by spectroscopic methods including NMR and mass spectrometry. The absolute configurations of penixanthones A (1) and B (2) were determined on the basis of electronic circular dichroism (ECD) data analysis...
March 16, 2017: Natural Product Research
Clementina M M Santos, Daniela Ribeiro, Artur M S Silva, Eduarda Fernandes
In response to an inflammatory stimulus, arachidonic acid (AA), the main polyunsaturated fatty acid present in the phospholipid layer of cell membranes, is released and metabolized to a series of eicosanoids. These bioactive lipid mediators of inflammation arise physiologically through the action of the enzymes 5-lipoxygenase (5-LOX) and cyclooxygenases (constitutive COX-1 and inducible COX-2). It is believed that dual inhibition of 5-LOX and COXs may have a higher beneficial impact in the treatment of inflammatory disorders rather than the inhibition of each enzyme...
March 11, 2017: Inflammation
Ming-Hui Wang, Kuo-Jun Zhang, Qin-Lan Gu, Xiao-Ling Bi, Jin-Xin Wang
Mangosteen (Garcinia mangostana Linn.) is a well-known tropical tree indigenous to Southeast Asia. Its fruit's pericarp abounds with a class of isoprenylated xanthones which are referred as mangostins. Numerous in vitro and in vivo studies have shown that mangostins and their derivatives possess diverse pharmacological activities, such as antibacterial, antifungal, antimalarial, anticarcinogenic, antiatherogenic activities as well as neuroprotective properties in Alzheimer's disease (AD). This review article provides a comprehensive review of the pharmacological activities of mangostins and their derivatives to reveal their promising utilities in the treatment of certain important diseases, mainly focusing on the discussions of the underlying molecular targets/pathways, modes of action, and relevant structure-activity relationships (SARs)...
February 2017: Chinese Journal of Natural Medicines
Sen Liu, Haibo Wang, Mingzhi Su, Gwi Ja Hwang, Jongki Hong, Jee H Jung
Two new metabolites, diorcinolic acid (1) and β-d-glucopyranosyl aspergillusene A (8), together with six diphenylethers (2-7), a diketopiperazine (9), a chromone (10) and a xanthone (11) were isolated from the fungus Aspergillus sydowii derived from the marine sponge Stelletta sp. The planar structures and their relative configurations were elucidated by analysing 1D, 2D NMR and HRESIMS data. Compound 8 is the first glycoside of phenolic bisabolane sesquiterpenes. Compounds 1 and 8 exhibited mild cytotoxicity against KB (human nasopharyngeal carcinoma cells), HepG2 (human liver cancer cells) and HCT 116 (human colon cancer cells)...
February 13, 2017: Natural Product Research
Haixia Wang, Xiang Yuan, Huiming Huang, Bo Zhang, Changnian Cao, Hong-Ping Zhao
The chemical investigation of ethanolic extract from Swertia mussotii Franch. has resulted in the isolation of 11 compounds which were identified as Orcinol-β-D-glucoside (1), Shamimin (2), Mangiferin (3), Decussatin (4), Bellidifolin (5), Desmethylbellidifolin (6), Protocatechuic acid (7), 1,7-Dihydroxy-3,8-dimethoxyxanthone (8), 1,8-Dihydroxy-3,5-dimethoxyxanthone (9), 1-Hydroxy-3,5-dimethoxyxanthone (10), Telephioidin (11). The chemical structures of these compounds were identified by a combination of spectroscopic analysis and a comparison with those reported in literature...
February 21, 2017: Natural Product Research
Supakorn Arthan, Cholpisut Tantapakul, Kwanjai Kanokmedhakul, Kasem Soytong, Somdej Kanokmedhakul
A new xanthone derivative, methyl 8-hydroxy-3-hydroxymethylxanthone-1-carboxylate (1), and seven known compounds, 8-hydroxy-3-methylxanthone-1-carboxylate (2), methyl 8-hydroxy-6-methylxanthone-1-carboxylate (3), ergosterol (4), cyathisterone (5), ergosta-4,6,8(14),22-tetraen-3-one (6), calvasterone (7) and 2-hexyl-3-methylmaleic anhydride (8) were first isolated from the fungus Apiospora montagnei. Their structures were elucidated on the basis of spectroscopic analysis (UV, IR, MS, 1D, and 2D NMR). Compounds 5 and 6 showed weak to very weak cytotoxicity against cancer cell lines, NCI-H187 and KB...
February 28, 2017: Natural Product Research
Chao-Yun Cai, Li Rao, Yong Rao, Jin-Xuan Guo, Zhi-Zun Xiao, Jing-Yu Cao, Zhi-Shu Huang, Bo Wang
Two series of compounds (chalcones and bis-chalcones) were designed, synthesized, and evaluated as α-glucosidase inhibitors (AGIs) with 1-deoxynojirimycin as positive control in vitro. Most of the compounds with two or four hydroxyl groups showed better inhibitory activities than 1-deoxynojirimycin towards α-glucosidase with noncompetitive mechanism. Moreover, most of the hydroxy bis-chalcones exhibit good α-glucosidase inhibitory activities in enzyme test. Inspiringly, bis-chalcones 2g (at 1 μM concentration) has stronger effect than 1-deoxynojirimycin on reducing the glucose level in HepG-2 cells (human liver cancer cell line)...
April 21, 2017: European Journal of Medicinal Chemistry
Marie Carene Nancy Picot, Onur Bender, Arzu Atalay, Gokhan Zengin, Loïc Loffredo, Francis Hadji-Minaglou, Mohamad Fawzi Mahomoodally
Aphloia theiformis (Vahl.) Benn. (AT) is traditionally used in Sub-Saharan African countries including Mauritius as a biomedicine for the management of several diseases. However, there is a dearth of experimental studies to validate these claims. We endeavoured to evaluate the inhibitory effects of crude aqueous extract as traditionally used together with the crude methanol extracts of AT leaves on urease, angiotensin (I) converting enzyme (ACE), acetylcholinesterase (AChE), cholesterol esterase (CEase), glycogen phosphorylase a (GPa), and glycation in vitro...
February 24, 2017: Biomedicine & Pharmacotherapy, Biomédecine & Pharmacothérapie
Susy Tjahjani
BACKGROUND: Malaria especially falciparum malaria still causes high morbidity and mortality in tropical countries. Several factors have been linked to this situation and the most important one is the rapid spread of parasite resistance to the currently available antimalarials, including artemisinin. Artemisinin is the main component of the currently recommended antimalarial, artemisinin based combination therapy (ACT), and it is a free radical generating antimalarial. Garcinia mangostana L (mangosteen) rind contain a lot of xanthone compounds acting as an antioxidant and exhibited antimalarial activity...
February 28, 2017: BMC Complementary and Alternative Medicine
Yunpeng Zhao, Wenhan Wang, Xihai Wu, Xiaoqian Ma, Ruize Qu, Xiaomin Chen, Chenghao Liu, Yaoge Liu, Xiaokai Wang, Pengcheng Yan, Hao Zhang, Jingrui Pan, Weiwei Li
This study aimed to investigate whether mangiferin played a protective role in a well-established dermatitis mouse model and tumor necrosis factor alpha (TNF-α)-induced RAW264.7 macrophages. Contact dermatitis is an inflammatory skin disease in the clinic, while its underlying mechanism still remains to be elucidated. Mangiferin, 1,3,6,7-tetrahydroxyxanthone-C2-β-d-glucoside (C-glucosyl xanthone), a natural antioxidant that was reported to inhibit inflammatory reactions, has been recently proved to be a potential therapy for inflammation...
February 18, 2017: International Immunopharmacology
Srinivasan Narasimhan, Shanmugam Maheshwaran, Imad A Abu-Yousef, Amin F Majdalawieh, Janarthanam Rethavathi, Prince Edwin Das, Palmiro Poltronieri
The microbial contamination in food packaging has been a major concern that has paved the way to search for novel, natural anti-microbial agents, such as modified α-mangostin. In the present study, twelve synthetic analogs were obtained through semi-synthetic modification of α-mangostin by Ritter reaction, reduction by palladium-carbon (Pd-C), alkylation, and acetylation. The evaluation of the anti-microbial potential of the synthetic analogs showed higher bactericidal activity than the parent molecule. The anti-microbial studies proved that I E showed high anti-bacterial activity whereas I I showed the highest anti-fungal activity...
February 12, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Joana R Almeida, Marta Correia-da-Silva, Emília Sousa, Jorge Antunes, Madalena Pinto, Vitor Vasconcelos, Isabel Cunha
Natural products with a sulfated scaffold have emerged as antifouling agents with low or nontoxic effects to the environment. In this study 13 sulfated polyphenols were synthesized and tested for antifouling potential using the anti-settlement activity of mussel (Mytilus galloprovincialis) plantigrade post-larvae and bacterial growth inhibition towards four biofilm-forming bacterial strains. Results show that some of these Nature-inspired compounds were bioactive, particularly rutin persulfate (2), 3,6-bis(β-D-glucopyranosyl) xanthone persulfate (6), and gallic acid persulfate (12) against the settlement of plantigrades...
February 13, 2017: Scientific Reports
Jie Lin, Renlei Wang, Guohua Xu, Zhengfeng Ding, Xueshen Zhu, Erwei Li, Ling Liu
Leptosphaerins H and I (1 and 2), two new xanthone derivatives, and six known compounds, leptosphaerin F (3), monodictysin B (4), norlichexanthone (5), leptosphaerin D (6), moniliphenone (7) and emodinbianthrone (8) have been isolated from a scale-up fermentation of the ascomycete fungus Leptosphaeria sp. Their structures were primarily elucidated by interpretation of NMR spectroscopic data. The absolute configuration of 1 was assigned using the modified Mosher method, whereas that of C-8a in 2 was determined via the CD data...
February 15, 2017: Journal of Antibiotics
William J Robson, Paul A Sutton, Paul McCormack, Neil P Chilcott, Steven J Rowland
Identification of the heteroatom (nitrogen, sulfur, and oxygen)-containing compounds of petroleum is of key importance when considering industrial and environmental issues associated with crude oil production. The more commonly performed methods of crude oil fractionation are often insufficient in the extent to which they separate oils, not allowing defined "molecular" fractions to be obtained. Methods capable of performing a class type separation are uncommon and are often extensive and resource and time intensive...
February 21, 2017: Analytical Chemistry
Shawn Blumberg, Stephen F Martin
The citreamicins comprise a novel class of polycyclic xanthone natural products that have not yet yielded to total synthesis. A concise 11-step synthesis of the pentacyclic core of citreamicin η is now reported that features the use of a general approach for the synthesis of 1,4-dioxygenated xanthones. The synthesis also showcases improved techniques for effecting regioselective bromination of certain substituted phenols and coupling of acetylides with hindered ketones.
February 8, 2017: Organic Letters
Hongmei Li, Tao Chen, Jing Sun, Weiqing Wang, Yulin Li
Two groups of xanthone isomers (1-hydroxy-3,5,8-trimethoxyxanthone and 1-hydroxy-3,7,8-trimethoxyxanthone, 1,8-dihydroxy-3,7-dimethoxyxanthone and 1,8-dihydroxy-3,5-dimethanolxanthone) and two other xanthones (3-methoxy-1,5,8-trihydroxyxanthone and 3,5-dimethoxy-1-hydroxyxanthone) were separated from Swertia franchetiana. First, a solvent system composed of petroleum ether/methanol/water (2:1:0.6, v/v) was developed for the liquid-liquid extraction of these xanthones from the crude extract. Then, an efficient method was established for one step separation of these six xanthones by high-speed counter-current chromatography using n-hexane/ethyl acetate/methanol/ethanol/water (6:4:4:2:4, v/v) as the solvent system...
February 6, 2017: Journal of Separation Science
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