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- Title
Taichunamides: Prenylated Indole Alkaloids from Aspergillus taichungensis (IBT 19404).
- Authors
Kagiyama, Ippei; Kato, Hikaru; Nehira, Tatsuo; Frisvad, Jens C.; Sherman, David H.; Williams, Robert M.; Tsukamoto, Sachiko
- 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.
- Subjects
INDOLE; MICROBIAL metabolites; ORGANONITROGEN compounds; ASPERGILLUS toxins; INDOLE alkaloids; ALKALOIDS
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 3, p1128
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201509462