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Antioxidant xanthones and anthraquinones isolated from a marine-derived fungus Aspergillus versicolor

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Chinese Journal of Natural Medicines 2018年第3期16卷 219-224页

作者： WU Ze-Hong LIU Dong XU Ying CHEN Jian-Liang LIN Wen-Han The Eighth Affiliated Hospital Sun Yat-sen University State Key Laboratory of Natural and Biomimetic Drugs Peking University Shenzhen Key Laboratory of Marine Bioresource & Eco-environmental Science Shenzhen Engineering Laboratory for Marine Algal Biotechnology College of Life Science Shenzhen University

Chemical examination of an EtOAc extract of cultured Aspergillus versicolor fungus from deep-sea sediments resulted in the isolation of four xanthones, eight anthraquinones and five alkaloids, including a new xanthone, oxisterigmatocystin D （1） and a new alkaloid, aspergillusine A （13）. High resolution electron impact mass spectrometry （HR-EI-MS）, FT-IR spectroscopy, and NMR techniques were used to elucidate the structures of these compounds, and the absolute configuration of compound 1 was established by its NMR features and coupling constant. Furthermore, the biosynthesis pathway of these xanthones and anthraquinones were deduced, and their antioxidant activity and cytotoxicity in human cancer cell lines （HTC-8, Bel-7420, BGC-823, A549, and A2780） were evaluated. The trolox equivalent antioxidant capacity （TEAC） assay indicated most of the xanthones and anthraquinones possessing moderate antioxidant activities. The Nrf2-dependent luciferase reporter gene assay revealed that compounds 6, 7, 9, and 12 potentially activated the expression of Nrf2-regulated gene. In addition, compounds 5 and 11 showed weak cytotoxicity on A549 with the ICs0 values of 25.97 and 25.60 gmol·L^-1, respectively.

关键词： Aspergillus versicolor xanthones Anthraquinones Antioxidant activity Cytotoxicity

Optimized Separation of Pharmacologically Active xanthones from Securidaca inappendiculata by Capillary Electrophoresis

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Chinese Chemical Letters 2002年第3期13卷 269-272页

作者： TaoBO XueDongYANG 等 ChemistryDepartment PekingUniversityBeijing100871 InstituteofMedicinalPlantDevelopment PekingUnionMedicalCollegeandChineseAcademyofMedicalSciencesBeijing100094

A capillary electrophoresis (CE) method has been firstly used for the separation of the therapeutically important xanthones from Securidaca inappendiculata. The separation of the nine xanthones was systematically optimized with respect to pH, concentration of running buffers, addition of sulfated b-CD, applied voltage and column temperature. Baseline separation was achieved for the nine xanthones in less than 15 minutes using a background electrolyte consisting of 200 mmol/L borate (pH 9.5) and 10 mmol/L sulfated b-CD.

关键词： Separation xanthones Securidaca inappendiculata capillary electrophoresis sulfated b-CD. Introduction

Optimized Separation of Nine xanthones by Microemulsion Electrokinetic Chromatography

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Chinese Chemical Letters 2002年第9期13卷 877-880页

作者： Tao BO Hu Wei LIU Ke An LI Chemistry Department Peking UniversityBeijing 100871

A microemulsion electrokinetic chromatography method has been firstly used for the separation of the therapeutically important xanthones from Securidaca inappendiculata. The separation of the nine xanthones was systematically optimized with respect to pH, composition of microemulsion, addition of cyclodextrins, applied voltage and column temperature. Baseline separation was successfully achieved for the nine xanthones, which was also compared with that by micellar electrokinetic chromatography.

关键词： Separation xanthones Securidaca inappendiculata microemulsion electrokinetic chromatography micellar electrokinetic chromatography.

New xanthones from Polygala crotalarioides

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Chemical Research in Chinese Universities 2006年第3期22卷 400-402页

作者： DENG Shi-ming YANG Xian-hui ZHAO You-xing ZHOU Jun State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of Botany Chinese Academy of Sciences Kunming 650204 P. R. China Ocean College Hainan University Haikou 570228 P. R. China

Introduction xanthones are secondary metabolites commonly occurring in a few higher plant families, fungi and lichen. Their high taxonomic value in such families and their pharmacological properties, including in vitro cytotoxicity, in vivo antitumour activity, antifungal, antibacterial, antiinflammatory properties and aldose reductase inhibitory activity have provoked great interest. The discovery of the antidiabetic activity of some axnthones＇ from Swertiaceae has prompted us to undertake a more broadly search for novel xanthones from plants of Polygalaceae. The phytochemical investigation has not been performed on this plant up to now. Herein we report the isolation and structure elucidation of two new xanthones （ compounds 1 and 2 ） and three known xanthones （compound 3, 4 and 5 ）.

关键词： Polygala crotalarfoides Polygalaceae xanthones

Identification and characterization of two new xanthones from Cudrania fruticosa

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Chinese Journal of Natural Medicines 2015年第10期13卷 781-785页

作者： LIANG Bo XU Li-Zhen YANG Shi-Lin GONG Xiao-Jie Medical College Dalian University Institute of Medicinal Plant Development Chinese Academy of Medical Sciences and Peking Union Medical College

The present study was designed to investigate the chemical constituents of the roots of Cudrania fruticosa Wight. Compounds were isolated by various column chromatographic methods including silica gel, polyamide, sephadex LH-20, and semi-preparative HPLC. Their structures were elucidated by a combination of 1D and 2D NMR techniques, mass spectrometry, and chemical methods. Two new xanthones, Cudraxanthone T and U(1-2), along with four known compounds(3-6) were isolated from the roots of Cudrania fruticosa Wight.

关键词： Cudrania fruticosa xanthones Cudraxanthone T Cudraxanthone U

Antioxidant Nature Adds Further Therapeutic Value: An Updated Review on Natural xanthones and Their Glycosides

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Digital Chinese Medicine 2019年第3期2卷 166-192页

作者： ZAFAR Salman JIAN Yu-Qing LI Bin PENG Cai-Yun CHOUDHARY Muhammad Iqbal RAHMAN Atta-ur WANG Wei Institute of Chemical Sciences University of PeshawarPeshawar 25120Pakistan TCM and Ethnomedicine Innovation&Development International Laboratory Sino-Pakistan TCM and Ethnomedicine Research CenterSchool of PharmacyHunan University of Chinese MedicineChangshaHunan 410208China Research Institute of Chemistry International Center for Chemical and Biological SciencesUniversity of KarachiKarachi 75270Pakistan

Plants have so much to offer as far as the discovery of new bioactive molecules is *** the several classes of phytochemicals,xanthones offer greater structural diversity and pharmacological *** are variable but definitely antioxidant in *** they are attractive targets for natural product and medicinal *** and their glycosides possess broad spectrum interesting biological activities,such as cytotoxic,anti-inflammatory,antioxidant,anti-bacterial,neuroprotective,anti-HIV,enzyme inhibition,and *** radical scavenging ability of these molecules accounts for most of their added therapeutic *** paper intended to serve as a guide for future endeavors in quest for these ***-Activity Relationship(SAR)and mechanism of action is given for better understanding of their role as pharmacological *** most recent advances in the isolation of bioactive xanthones and their glycosides were presented *** paper will assist in directed approaches towards the discovery of analogues of xanthones.

关键词： xanthones Xanthone glycosides Antioxidant Radical scavenging Xanthone dimers Xanthone trimers

Flavanoids and xanthones isolated from Arenaria serpyllifolia L.

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Journal of Chinese Pharmaceutical Sciences 2013年第3期22卷 286-288页

作者：周观燊杨晓娟姜勇屠鹏飞北京大学医学部天然药物及仿生药物国家重点实验室北京大学药学院北京100191

Eight known compounds were isolated from the whole plants ofArenaria serpyllifolia L. by solvent fractionation and subsequent separations with silica gel, ODS, Sephadex LH-20 and semi-preparative HPLC chromatography. Their structures were determined by spectroscopic analysis and identified as quercetin （1）, quercetin 7-O-α-L-rhamnoside （2）, quercetin 3-O-α-L- rhamnoside （3）, 3-O-methyl quercetin （4）, 1,5-dihydroxyxanthone （5）, 1,5-dihydroxyxanthone-6-O-β-D-glucoside （6）, 5-hydroxy- l-methoxyxanthone （7） and 6-deoxyisojacareubin （8）. All these compounds were isolated from this title plant for the first time, and compounds 5-8 were obtained from genus Arenaria for the first time.

关键词： Arenaria serpyllifolia L. Chemical constituents Flavonoids xanthones

xanthones from the roots of Calophyllum membranaceum

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Xanthones from the roots of Calophyllum membranaceum

Bioactive xanthones from whole plants of Gentianella acuta

第九届全国药用植物及植物药学术研讨会

作者： Yu Jun,Song Xin-Ming,Chen Guang-ying~*,Han Chang-Ri~*,Zhao Jun,Yin Qi-Wei (Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education College of Chemistry and Chemical Engineering,Hainan Normal University,Haikou 571158,China)

AIM:To investigate chemical components of the ethyl acetate of Calophyllum ***:Isolation and purification were carried out by several column chromatographic *** were identified based on their physicochemical properties and spectral ***:Eleven xanthones were isolated from ethanol extract of the roots of ***,the structures of those xanthones were elucidated as 1,7-dihydroxy-3-methoxyxanthone(1),l,5,6-trihydroxyxanthone(2), l,3,6-trihydroxy-5- methoxy -xanthone(3),1,3,7-trihydroxyxanthone(4), l-hydroxy-6,7-dimethoxyxanthone(5),3,5- dihydroxyxanthone(6),4-hydroxy-3-methoxy xanthone(7),1,2-dimethoxyxanthone(8),1,3,5- trihydroxyxanthone(9),pyranojacareubin (10),1,4,5- trihydroxyxanthone(11).CONCLUSION:All compounds are firstly isolated from this plant and compounds 1,3-7,9 were isolated from the Calophyllum genus for the first time.

关键词： chemical components xanthones Calophyllium membranaceum Guttiferae

来源： cnki会议评论

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Chinese Herbal Medicines 2018年第1期10卷 99-102页

作者： sheng-cai yang jing-ya ruan yan-xia liu zhi-juan ding ya-juan ni tao wang yi zhang tianjin key laboratory of tcm chemistry and analysis institute of traditional chinese medicinetianjin university of traditional chinese medicinetianjin 300193China

Objective： To study the constituents from the whole plants of Gentianella acuta and their biological ***： The compounds were isolated by multiple chromatographic methods and the structures of mentioned isolates were determined by routine NMR experiments and chemical ***： A phytochemical investigation to obtain intestine motility inhibitor resulted in the isolation of one new xanthone glycoside,gentixanthonoside A（1）,along with nine tetrahydroxanthones,1,3,5R,8S-tetrahydroxy-5,6,7,8-tetrahydroxanthone（2）,1,3,5S,8S-tetrahydroxy-5,6,7,8-tetrahydroxanthone（3）,amarellin E（4）,amarellin F（5）,swertiachoside B（6）,amarellin D（7）,amarellin C（8）,amarellin A（9）,and amarellin B（10）from the whole plants of ***： Compounds 2 –10 showed significant reduce effects on contraction tension at 40 μM.

关键词： Gentianella acuta (Michx.) Hulten intestine motility Mongolia native medicine xanthones