title: Identification and biological evaluation of secondary metabolites from the endolichenic fungus Aspergillus versicolor.
abstract: A chemical investigation of the endolichenic fungus Aspergillus versicolor (125a), which was found in the lichen Lobaria quercizans, resulted in the isolation of four novel diphenyl ethers, named diorcinols F-H (1-3, resp.) and 3-methoxyviolaceol-II (4), eight new bisabolane sesquiterpenoids, named (-)-(R)-cyclo-hydroxysydonic acid (5), (-)-(7S,8R)-8-hydroxysydowic acid (6), (-)-(7R,10S)-10-hydroxysydowic acid (7), (-)-(7R,10R)-iso-10-hydroxysydowic acid (8), (-)-12-acetoxy-1-deoxysydonic acid (9), (-)-12-acetoxysydonic acid (10), (-)-12-hydroxysydonic acid (11), and (-)-(R)-11-dehydrosydonic acid (12), two new tris(pyrogallol ethers), named sydowiols D (13) and E (14), and fifteen known compounds, 15-29. All of the structures were determined by spectroscopic analyses, and a number of them were further identified through chemical transformations and electronic circular dichroism (ECD) calculations. Preliminary bioassays of these isolates for the determination of their inhibitory activities against the fungus Candida albicans, and their cytotoxicities against the human cancer cell lines PC3, A549, A2780, MDA-MB-231, and HEPG2 were also evaluated.
authors: Department of Natural Products Chemistry, Key Lab of Chemical Biology of Ministry of Education, School of Pharmaceutical Science, Shandong University, No. 44 West Wenhua Road, Jinan 250012, P. R. China (phone: +86-531-88382012; fax: +86-531-88382019).
authors: Xiao-Bin
authors: XB
authors: Li
authors: Yan-Hui
authors: YH
authors: Zhou
authors: Rong-Xiu
authors: RX
authors: Zhu
authors: Wen-Qiang
authors: WQ
authors: Chang
authors: Hui-Qing
authors: HQ
authors: Yuan
authors: Wei
authors: W
authors: Gao
authors: Lu-Lu
authors: LL
authors: Zhang
authors: Zun-Tian
authors: ZT
authors: Zhao
authors: Hong-Xiang
authors: HX
authors: Lou
mesh_terms: D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000494:pharmacology*; D001230:Aspergillus / Q000737:chemistry* / Q000378:metabolism; D002176:Candida albicans / Q000187:drug effects; D045744:Cell Line, Tumor / Q000187:drug effects; D002942:Circular Dichroism; D004353:Drug Evaluation, Preclinical / Q000379:methods; D006801:Humans; D008011:Lichens / Q000382:microbiology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010647:Phenyl Ethers / Q000737:chemistry / Q000494:pharmacology; D064210:Secondary Metabolism; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification; D013329:Structure-Activity Relationship
chemical_list: C549950:11-dehydrosydonic acid; C549951:12-acetoxysydonic acid; D000935:Antifungal Agents; D000972:Antineoplastic Agents, Phytogenic; D010647:Phenyl Ethers; D012717:Sesquiterpenes
keywords: Antifungal activity; Aspergillus versicolor; Bisabolane sesquiterpenoid; Cytotoxic activity; Endolichenic fungus; Fungi; Sesquiterpenoids