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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.

SUBMITTER: Kato H

PROVIDER: S-EPMC4456087 | biostudies-literature | 2015 Feb

REPOSITORIES: biostudies-literature

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Isolation of notoamide S and enantiomeric 6-epi-stephacidin A from the fungus Aspergillus amoenus: biogenetic implications.

Kato Hikaru H Nakahara Takashi T Sugimoto Kayo K Matsuo Kanae K Kagiyama Ippei I Frisvad Jens C JC Sherman David H DH Williams Robert M RM Tsukamoto Sachiko S

Organic letters 20150123 3

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 ...[more]

PMID: 25615822

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