title: Taichunamides: Prenylated Indole Alkaloids from Aspergillus taichungensis (IBT 19404).
abstract: Seven new prenylated indole alkaloids, taichunamides A-G, were isolated from the fungus Aspergillus taichungensis (IBT 19404). Taichunamides A and B contained an azetidine and 4-pyridone units, respectively, and are likely biosynthesized from notoamide S via (+)-6-epi-stephacidin A. Taichunamides C and D contain endoperoxide and methylsulfonyl units, respectively. This fungus produced indole alkaloids containing an anti-bicyclo[2.2.2]diazaoctane core, whereas A. protuberus and A. amoenus produced congeners with a syn-bicyclo[2.2.2]diazaoctane core. Plausible biosynthetic pathways to access these cores within the three species likely arise from an intramolecular hetero Diels-Alder reaction.
authors.affiliation: Graduated School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto, 862-0973, Japan.
authors.forename: Ippei
authors.initials: I
authors.lastname: Kagiyama
authors.affiliation: Graduated School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto, 862-0973, Japan.
authors.forename: Hikaru
authors.initials: H
authors.lastname: Kato
authors.affiliation: Graduated School of Integrated Arts and Sciences, Hiroshima University, 1-7-1 Kagamiyama, Higashi-hiroshima, 739-8521, Japan.
authors.forename: Tatsuo
authors.initials: T
authors.lastname: Nehira
authors.affiliation: Section for Eukaryotic Biotechnology, Departments of System Biology, Technical University of Denmark, Building 221, 2800, Kongens Lyngby, Denmark.
authors.forename: Jens C
authors.initials: JC
authors.lastname: Frisvad
authors.affiliation: Life Sciences Institute and Departments of Medicinal Chemistry, Chemistry, Microbiology & Immunology, The University of Michigan, 210 Washtenaw Avenue, Ann Arbor, MI, 48109-2216, USA.
authors.forename: David H
authors.initials: DH
authors.lastname: Sherman
authors.affiliation: Department of Chemistry, Colorado State University, 1301 Center Avenue, Fort Collins, CO, 80523, USA.|Department of Chemistry, Colorado State University, 1301 Center Avenue, Fort Collins, CO, 80523, USA.
authors.forename: Robert M
authors.initials: RM
authors.lastname: Williams
authors.affiliation: Graduated School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto, 862-0973, Japan. sachiko@kumamoto-u.ac.jp.
authors.forename: Sachiko
authors.initials: S
authors.lastname: Tsukamoto
mesh_terms: D001230:Aspergillus / Q000737:chemistry*; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D054876:Prenylation
chemical_list: D026121:Indole Alkaloids
keywords: alkaloids; biosynthesis; cycloaddition; natural products; structure elucidation