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Taichunamides: Prenylated Indole Alkaloids from Aspergillus taichungensis (IBT 19404)
Author(s) -
Kagiyama Ippei,
Kato Hikaru,
Nehira Tatsuo,
Frisvad Jens C.,
Sherman David H.,
Williams Robert M.,
Tsukamoto Sachiko
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201509462
Subject(s) - indole test , stereochemistry , bicyclic molecule , intramolecular force , chemistry , prenylation , fungus , aspergillus , indole alkaloid , biology , organic chemistry , botany , enzyme
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.