title: Fumigaclavines D-H, new ergot alkaloids from endophytic Aspergillus fumigatus.
abstract: Ergot alkaloids are toxins which are produced biotechnologically on an industrial scale. The chemical investigation of endophytic Aspergillus fumigatus resulted in the isolation of five new ergot alkaloids named fumigaclavines D-H (2-6), along with three known analogues, fumigaclavine C (1), festuclavine (7), and fumigaclavine A (8). Their structures were unequivocally elucidated by extensive spectroscopic analyses in association with X-ray single-crystal diffraction. Fumigaclavines D-H are interesting clavine-type ergot alkaloids featuring a reverse prenyl moiety at C-2, with 1-4, 6, and 8 bearing additional substituents, e.g., an OH or OAc group at C-9. Compounds 2, 4, and 6-8 showed a broad spectrum of antimicrobial activity against a panel of anaerobic microorganisms, of which compounds 4 and 6 were the most active against Veillonella parvula with an MIC=16 µg/mL compared to that (0.12 µg/mL) of tinidazole, co-assayed as a positive reference.
authors.affiliation: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China.
authors.forename: Jing
authors.initials: J
authors.lastname: Xu
authors.affiliation: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China.
authors.forename: Yong Chun
authors.initials: YC
authors.lastname: Song
authors.affiliation: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China.
authors.forename: Ye
authors.initials: Y
authors.lastname: Guo
authors.affiliation: Department of Clinical Laboratory, the First Affiliated Hospital of Nanjing Medical University, Nanjing, P. R. China.
authors.forename: Ya Ning
authors.initials: YN
authors.lastname: Mei
authors.affiliation: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China.
authors.forename: Ren Xiang
authors.initials: RX
authors.lastname: Tan
mesh_terms: D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001232:Aspergillus fumigatus / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D004876:Ergot Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005285:Fermentation; D008826:Microbial Sensitivity Tests; D019906:Nuclear Magnetic Resonance, Biomolecular; D014961:X-Ray Diffraction
chemical_list: D000890:Anti-Infective Agents; D004876:Ergot Alkaloids