Ippei Kagiyama1, Hikaru Kato1, Tatsuo Nehira2, Jens C Frisvad3, David H Sherman4, Robert M Williams5,5, Sachiko Tsukamoto6. 1. Graduated School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto, 862-0973, Japan. 2. Graduated School of Integrated Arts and Sciences, Hiroshima University, 1-7-1 Kagamiyama, Higashi-hiroshima, 739-8521, Japan. 3. Section for Eukaryotic Biotechnology, Departments of System Biology, Technical University of Denmark, Building 221, 2800, Kongens Lyngby, Denmark. 4. Life Sciences Institute and Departments of Medicinal Chemistry, Chemistry, Microbiology & Immunology, The University of Michigan, 210 Washtenaw Avenue, Ann Arbor, MI, 48109-2216, USA. 5. Department of Chemistry, Colorado State University, 1301 Center Avenue, Fort Collins, CO, 80523, USA. 6. Graduated School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto, 862-0973, Japan. sachiko@kumamoto-u.ac.jp.
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.
Seven new prenylated indole alkaloids, n class="Chemical">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.
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