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.

SUBMITTER: Kagiyama I 

PROVIDER: S-EPMC4960981 | biostudies-literature | 2016 Jan

REPOSITORIES: biostudies-literature