title: Aspergillines A-E, highly oxygenated hexacyclic indole-tetrahydrofuran-tetramic acid derivatives from Aspergillus versicolor.
abstract: Aspergillines A-E (1-5) are highly oxygenated cyclopiazonic acid (CPA)-derived alkaloids bearing a rigid and sterically congested hexacyclic indole-tetrahydrofuran-tetramate scaffold, isolated from the endophytic fungus Aspergillus vesicolor. Apergillines A-C represent a new subclass of CPA-derived alkaloids, and aspergillines B and E possess a butanoic acid methyl ester moiety. The structures, including absolute configuration, were elucidated by interpretation of the NMR, X-ray crystallographic, and circular dichroism data. All compounds displayed anti-TMV and cytotoxic activities.
authors.affiliation: Key Laboratory of Tobacco Chemistry of Yunnan Province, China Tobacco Yunnan Industrial Co., Ltd. , Kunming 650231, People's Republic of China.
authors.forename: Min
authors.initials: M
authors.lastname: Zhou
authors.forename: Ming-Ming
authors.initials: MM
authors.lastname: Miao
authors.forename: Gang
authors.initials: G
authors.lastname: Du
authors.forename: Xiao-Nian
authors.initials: XN
authors.lastname: Li
authors.forename: Shan-Zhai
authors.initials: SZ
authors.lastname: Shang
authors.forename: Wei
authors.initials: W
authors.lastname: Zhao
authors.forename: Zhi-Hua
authors.initials: ZH
authors.lastname: Liu
authors.forename: Guang-Yu
authors.initials: GY
authors.lastname: Yang
authors.forename: Chun-Tao
authors.initials: CT
authors.lastname: Che
authors.forename: Qiu-Fen
authors.initials: QF
authors.lastname: Hu
authors.forename: Xue-Mei
authors.initials: XM
authors.lastname: Gao
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001230:Aspergillus / Q000737:chemistry*; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007211:Indoles / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011760:Pyrrolidinones / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D000970:Antineoplastic Agents; D006576:Heterocyclic Compounds, 4 or More Rings; D007211:Indoles; D011760:Pyrrolidinones; C009435:tetramic acid; C000543:cyclopiazonic acid