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Isolation of antipodal (-)-versicolamide B and notoamides L-N from a marine-derived Aspergillus sp.

ABSTRACT: Antipodal (-)-versicolamide B and notoamides L-N were isolated from a marine-derived Aspergillus sp. The possible biosynthetic pathway of enantiomeric pairs of notoamide B and versicolamide B are proposed. Notoamide L is the first metabolite containing 25 carbons in the related prenylated indole alkaloids. Notoamide M is potentially a precursor to the proposed azadiene species involved in the putative intramolecular Diels-Alder reaction in the biogenesis of the bicyclo[2.2.2]diazaoctane ring system.

SUBMITTER: Tsukamoto S 

PROVIDER: S-EPMC2829632 | biostudies-literature | 2009 Mar

REPOSITORIES: biostudies-literature

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Isolation of antipodal (-)-versicolamide B and notoamides L-N from a marine-derived Aspergillus sp.

Tsukamoto Sachiko S   Kawabata Tetsuro T   Kato Hikaru H   Greshock Thomas J TJ   Hirota Hiroshi H   Ohta Tomihisa T   Williams Robert M RM  

Organic letters 20090301 6

Antipodal (-)-versicolamide B and notoamides L-N were isolated from a marine-derived Aspergillus sp. The possible biosynthetic pathway of enantiomeric pairs of notoamide B and versicolamide B are proposed. Notoamide L is the first metabolite containing 25 carbons in the related prenylated indole alkaloids. Notoamide M is potentially a precursor to the proposed azadiene species involved in the putative intramolecular Diels-Alder reaction in the biogenesis of the bicyclo[2.2.2]diazaoctane ring sys  ...[more]

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