title: Isolation of notoamide S and enantiomeric 6-epi-stephacidin A from the fungus Aspergillus amoenus: biogenetic implications.
abstract: Notoamide S has been hypothesized to be a key biosynthetic intermediate for characteristic metabolites stephacidin A, notoamide B, and versicolamide B in Aspergillus sp. but has not yet been isolated. The isolation of notoamide S and an enantiomeric mixture of 6-epi-stephacidin A enriched with the (-)-isomer from Aspergillus amoenus is reported. The presence of (+)-versicolamide B suggests that the fungus possesses only the oxidase, which converts (+)-6-epi-stephacidin A into (+)-Versicolamide B, but not for (-)-6-epi-Stephacidin A.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kumamoto University , 5-1 Oe-honmachi, Kumamoto 862-0973, Japan.
authors.forename: Hikaru
authors.initials: H
authors.lastname: Kato
authors.forename: Takashi
authors.initials: T
authors.lastname: Nakahara
authors.forename: Kayo
authors.initials: K
authors.lastname: Sugimoto
authors.forename: Kanae
authors.initials: K
authors.lastname: Matsuo
authors.forename: Ippei
authors.initials: I
authors.lastname: Kagiyama
authors.forename: Jens C
authors.initials: JC
authors.lastname: Frisvad
authors.forename: David H
authors.initials: DH
authors.lastname: Sherman
authors.forename: Robert M
authors.initials: RM
authors.lastname: Williams
authors.forename: Sachiko
authors.initials: S
authors.lastname: Tsukamoto
mesh_terms: D001230:Aspergillus / Q000378:metabolism*; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; C520596:notoamide B; C000596573:notoamide S; C470895:stephacidin A; C529010:versicolamide B