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Xiaoli Xu, Yue Wu, Mingyang Hu, Xiang Li, Qichao Bao, Jinlei Bian, Qidong You, Xiaojin Zhang
DDO-6101, a simplified structure obtained from the Garcinia natural product (NP) gambogic acid (GA), has been previously shown to possess high cytotoxicity to a variety of human tumour cell lines. To improve its physicochemical properties and in vivo cytotoxic potency, a series of novel carbamate-bearing derivatives based on DDO-6101 was synthesized and characterized. The structural modifications revealed that the presence of a carbamate moiety was useful for obtaining comparable cytotoxicity and improved aqueous solubility and permeability...
October 21, 2016: Scientific Reports
Hong Zhang, Zheng Dan, Zhi-Jie Ding, Yuan-Zhi Lao, Hong-Sheng Tan, Hong-Xi Xu
A UPLC-PDA-QTOFMS-guided isolation strategy was employed to screen and track potentially new compounds from Garcinia oblongifolia. As a result, two new prenylated xanthones, oblongixanthones D and E (1-2), six new prenylated benzoylphloroglucinol derivatives, oblongifolins V-Z (3-7) and oblongifolin AA (8), as well as a known compound oblongifolin L (9), were isolated from the EtOAc-soluble fraction of an acetone extract of the leaves of Garcinia oblongifolia guided by UPLC-PDA-QTOFMS analysis. The structures of the new compounds were elucidated by 1D- and 2D-NMR spectroscopic analysis and mass spectrometry...
October 21, 2016: Scientific Reports
Alamgir A Dar, Nisar A Dangroo, Arun Raina, Arem Qayum, Shashank Singh, Anil Kumar, Payare L Sangwan
Five new xanthones, named coxanthones A-E (1-5), together with 21 known secondary metabolites (6-26) that include seven xanthones, five flavonoids, two steroids and seven triterpenoids were isolated from the chemically unexplored whole plant Codonopsis ovata. The structures of new metabolites were elucidated by HRMS, interpretation of NMR spectra and other spectroscopic techniques. The absolute configuration of the stereogenic centre of coxanthone B (2) was determined by electronic circular dichroism (ECD) spectroscopy...
October 10, 2016: Phytochemistry
Hossam M Abdallah, Hany M El-Bassossy, Gamal A Mohamed, Ali M El-Halawany, Khalid Z Alshali, Zainy M Banjar
Advanced glycation end-products (AGEs) are associated with a non-enzymatic reaction between the amino group of a protein and the carbonyl group of a sugar during hyperglycemia. The precipitation of AGEs in different tissues leads to many complications, such as endothelial dysfunction, cardiovascular complications, atherosclerosis, retinopathy, neuropathy, and Alzheimer's disease. Garcinia mangostana L. (Clusiaceae) (GM) was selected owing to the ability of its polar and non-polar fractions to inhibit AGE formation...
October 13, 2016: Journal of Natural Medicines
M Cuccioloni, L Bonfili, M Mozzicafreddo, V Cecarini, S Scuri, M Cocchioni, M Nabissi, G Santoni, A M Eleuteri, M Angeletti
Mangiferin is a natural xanthone glycoside with therapeutic potential. Herein, its cytotoxic properties were explored in a human cell model of breast adenocarcinoma. The results supported the multi-target nature of mangiferin action, as the inhibition of three enzymatic systems, namely HMG-CoA reductase, the proteasome and plasmin, respectively in charge of regulating cholesterol homeostasis, protein turnover and cell adhesion, was documented for the first time. Globally, mangiferin was able to selectively block breast cancer cell growth by inducing apoptosis and by arresting cell proliferation through a combined action on cholesterol and proteasome pathways, as well as to inhibit plasmin-mediated mechanisms of cell migration...
October 12, 2016: Food & Function
Xiong Wei, Danlin Liang, Qing Wang, Xiangbao Meng, Zhongjun Li
Total synthesis of mangiferin, homomangiferin, and neomangiferin, three C-glycosyl xanthone natural products with a wide spectrum of pharmacological effects, has been achieved starting from 2,3,4,6-tetra-O-benzyl-α/β-d-glucopyranose. The key steps involve a stereoselective Lewis acid promoted C-glycosylation of protected phloroglucinol with tetrabenzylglucopyranosyl acetate and a highly regioselective base-induced cyclization for the construction of the core xanthone skeleton.
September 21, 2016: Organic & Biomolecular Chemistry
Tandeka Magcwebeba, Pieter Swart, Sonja Swanevelder, Elizabeth Joubert, Wentzel Gelderblom
Ultraviolet B (UVB) radiation is one of the major predisposing risk factors of skin cancer. The anticancer and photoprotective effects of unoxidized rooibos (Aspalathus linearis) and honeybush (Cyclopia) herbal teas, containing high levels of dihydrochalones and xanthones, respectively, have been demonstrated in skin cancer models in vivo. In the current study, the anti-inflammatory effects of methanol and aqueous extracts of these herbal teas were investigated in a UVB/HaCaT keratinocyte model with intracellular interleukin-1α (icIL-1α) accumulation as a biomarker...
October 2, 2016: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Yanhua Jia, Chengwen Xiong
The anti-microbial and anti-oxidant effects of xanthones extract from Swertia macrosperma C.B. Clark were investigated using extracts from whole plant and partitioned by petroleum ether, ethyl acetate and n-butanol, respectively. Anti-microbial and anti-oxidant activities were detected among different fractions. High-performance liquid chromatography was performed to separate and purify the elutions. The compounds were elucidated by 1H, 13C NMR and LCMS. The ethyl acetate extract showed maximum inhibitory activity in fungal organisms and Gram-positive bacteria, and had the highest anti-oxidant capacity...
August 10, 2016: Natural Product Research
Tandeka Unathi Magcwebeba, Sylvia Riedel, Sonja Swanevelder, Pieter Swart, Dalene De Beer, Elizabeth Joubert, Wentzel Christoffel Andreas Gelderblom
OBJECTIVES: The relationship between polyphenol constituents, antioxidant properties of aqueous and methanol extracts of green tea (Camellia sinensis), the herbal teas, rooibos (Aspalathus linearis) and honeybush (Cyclopia spp.), against skin cell viability was investigated in vitro. METHODS: The effect of extracts, characterised in terms of polyphenol content and antioxidant properties, on cell viability of premalignant, normal and malignant skin cells was determined...
September 27, 2016: Journal of Pharmacy and Pharmacology
Jyotshna, Puja Khare, Karuna Shanker
Xanthones are naturally synthesized in various biological systems such as plants, lichens, and fungi and are stored as by-products. In addition to taxonomic significance they are also important in the treatment/management of a number of human disorders. Mangiferin and its derived lead molecule have never qualified for use in a clinical trial despite a number of pharmacological studies that have proven its effectiveness as an antioxidant, analgesic, antidiabetic, antiproliferative, chemopreventive, radioprotective, cardiotonic, immunomodulatory, and diuretic...
September 23, 2016: BioFactors
Chi-Su Yoon, Dong-Cheol Kim, Tran Hong Quang, Jungwon Seo, Dae Gill Kang, Ho Sub Lee, Hyuncheol Oh, Youn-Chul Kim
Cudrania tricuspidata Bureau (Moraceae) is an important source of traditional Korean and Chinese medicines used to treat neuritis and inflammation. Cudratricusxanthone A (1), a prenylated xanthone, isolated from C. tricuspidata, has a variety of biological and therapeutic activities. The goal of this study was to examine the effects of compound 1 on neuroinflammation and characterize its mechanism of action in lipopolysaccharide (LPS)-stimulated BV2 microglia. Cudratricusxanthone A (1) suppressed the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 enzymes and decreased the production of iNOS-derived nitric oxide and COX-2-derived prostaglandin E2 in LPS-stimulated mouse BV2 microglia...
2016: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Mary Snow Setzer, Javad Sharifi-Rad, William N Setzer
Recently, the emergence and spread of pathogenic bacterial resistance to many antibiotics (multidrug-resistant strains) have been increasing throughout the world. This phenomenon is of great concern and there is a need to find alternative chemotherapeutic agents to combat these antibiotic-resistant microorganisms. Higher plants may serve as a resource for new antimicrobials to replace or augment current therapeutic options. In this work, we have carried out a molecular docking study of a total of 561 antibacterial phytochemicals listed in the Dictionary of Natural Products, including 77 alkaloids (17 indole alkaloids, 27 isoquinoline alkaloids, 4 steroidal alkaloids, and 28 miscellaneous alkaloids), 99 terpenoids (5 monoterpenoids, 31 sesquiterpenoids, 52 diterpenoids, and 11 triterpenoids), 309 polyphenolics (87 flavonoids, 25 chalcones, 41 isoflavonoids, 5 neoflavonoids, 12 pterocarpans, 10 chromones, 7 condensed tannins, 11 coumarins, 30 stilbenoids, 2 lignans, 5 phenylpropanoids, 13 xanthones, 5 hydrolyzable tannins, and 56 miscellaneous phenolics), 30 quinones, and 46 miscellaneous phytochemicals, with six bacterial protein targets (peptide deformylase, DNA gyrase/topoisomerase IV, UDP-galactose mutase, protein tyrosine phosphatase, cytochrome P450 CYP121, and NAD⁺-dependent DNA ligase)...
September 12, 2016: Antibiotics
Devendra Mishra, Shivani Joshi, Shweta Mishra, Mukesh Lal Sah, Sama Ajay, Arun K Shaw
The chloroform extract of Swertia cordata (G. Don) roots was subjected to column chromatography, afforded two (one new and one known) xanthones. Both the compounds were isolated for the first time from S. cordata. The structures of the isolated compounds were established on the basis of melting point,1D ((1)H NMR & (13)C NMR) and 2D ((1)H (1)H COSY, HSQC & HMBC) NMR spectroscopy, in addition to high-resolution mass spectrometry.
September 13, 2016: Natural Product Research
S Genovese, S Fiorito, V A Taddeo, F Epifano
Prenylated xanthones are secondary metabolites that are particularly common in plants belonging to the Clusiaceae family. Such compounds have been the focus intensive research because of their potential as biologically active agents. Here, we survey data published over the past decade relating to the properties of prenylated xanthones to provide a more detailed view of the potential of these naturally occurring compounds as therapeutic agents.
September 2, 2016: Drug Discovery Today
Hani Z Asfour
A prenylated xanthone, α-mangostin was separated from the alcoholic extract of Garcinia mangostana pericarp. Its structure was established by different spectroscopic analysis. The total methanolic extract (TME) and different fractions of G. mangostana pericarp as well as α-mangostin were assessed for their antimicrobial and quorum sensing inhibitory effects (QSI). The TME, CHCl3 fraction, and α-mangostin exhibited strong activity against all tested strains. While, EtOAc, n-BuOH, and aqueous fractions showed moderate activity against some of the tested organisms...
July 2016: Pakistan Journal of Pharmaceutical Sciences
Soo-Myeong Jeon, Dong-Sung Lee, Gil-Saeong Jeong
HEADINGS ETHNOPHARMACOLOGICAL RELEVANCE: The roots of Cudrania tricuspidata is a deciduous tree found in Korea, China, and Japan. C. tricuspidata contains an abundance of various minerals, B vitamins, and flavonoids to help prevent diverse cancers. Cudratricusxanthone A (CTXA), a compound isolated from the roots of C. tricuspidata, has potent anti-proliferative, antioxidative, and monoamine oxidase inhibitory effects. AIM OF THE STUDY: In the present study, cudratricusxanthone A (CTXA) is a xanthone isolated from the bioassay-guided fractionation of the EtOH extract of C...
August 29, 2016: Journal of Ethnopharmacology
Mariusz Kózka, Karolina Słoczyńska, Natalia Szkaradek, Anna M Waszkielewicz, Elżbieta Pękala, Henryk Marona
This in vitro study was designed to examine the effect of some newly synthesized aminoalcanolic derivatives of xanthone (I, II) and aroxyalkyl derivatives of 2-methoxyphenylpiperazine (III, IV) having cardiovascular activity on the haemorheological parameters of RBCs from healthy individuals and patients with chronic venous disease. Additionally, the influence of compounds I-IV on some RBCs associated enzymes such as acetylcholinesterase (Ache), glucose-6-phosphate dehydrogenase (G6PD) and glutathione reductase (GR) as well as glutathione (GSH) content were determined in vitro in RBCs from healthy subjects...
August 16, 2016: Clinical Hemorheology and Microcirculation
Qianyu Liu, Dan Li, Anqi Wang, Zhen Dong, Sheng Yin, Qingwen Zhang, Yang Ye, Liangchun Li, Ligen Lin
Mangosteen (Garcinia mangostana, Clusiaceae) is called "queen of fruit" in Southeast Asia. In the current study, three dimeric xanthones, garcinoxanthones A-C, and four monomeric xanthones, garcinoxanthones D-G, together with 18 known xanthones, were isolated from the pericarps of G. mangostana, collected in Thailand. The structures of garcinoxanthones A-G were elucidated by analysis of their 1D and 2D NMR and other spectroscopic data, and their absolute configurations were determined by the CD spectra. All seven compounds were tested for nitric oxide (NO) inhibitory activity on lipopolysaccharide (LPS)-stimulated RAW264...
November 2016: Phytochemistry
Luísa Nathália Bolda Mariano, Luisa Mota da Silva, Priscila de Souza, Thaise Boeing, Lincon Bordignon Somensi, Tiago José Bonomini, Franco Delle Monache, Valdir Cechinel Filho, Sérgio Faloni de Andrade, Rivaldo Niero
The present study was designed to investigate the gastroprotective effect of xanthones 7-preniljacareubin (PJB), 1,3,5,6-tetrahydroxy xanthone (THX), 3-demethyl-2-geranyl-4-prenylbellidypholine (DGP) and 1,5,8-trihydroxy-4', 5'-dimethyl-2H-pyrane (2,3:3,2)-4-(3-methylbut-2-enyl) xanthone (TDP) isolated of branches from G. achachairu. Their structures were identified through the spectroscopic analysis in comparison with previously reported data. The xanthones were tested at dose of 10 mg/kg against ethanol 60%/HCl 0...
October 25, 2016: Chemico-biological Interactions
Anna M Waszkielewicz, Karolina Słoczyńska, Elżbieta Pękala, Paweł Żmudzki, Agata Siwek, Anna Gryboś, Henryk Marona
A series of new xanthone derivatives have been synthesized and evaluated for their anticonvulsant properties in the maximal electroshock (MES), subcutaneous metrazole (ScMet) tests as well as for neurotoxicity in the rotarod (TOX) in mice, i.p. and rats, p.o. Compound 9: R,S-2-{2-[(1-hydroxybutan-2-yl]amino)ethoxy}-9H-xanthen-9-one and compound 12: R,S-2-{3-[(1-hydroxybutan-2-yl)amino]propoxy}-9H-xanthen-9-one exerted activity in rats, p.o. 2 and 4 h after administration, respectively. Therefore, metabolic stability of the compounds was evaluated with use of rats microsomes, resulting in half-life t1/2 136 and 108 min, respectively, indicating that either the metabolites are very active, or the parent compounds exert other ADME properties other than metabolism which influence the late onset of activity...
August 20, 2016: Chemical Biology & Drug Design
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