Aspergillines A–E, Highly Oxygenated Hexacyclic Indole–Tetrahydrofuran–Tetramic Acid Derivatives from Aspergillus versicolor

Aspergillines A–E (1–5) are highly oxygenated cyclopiazonic acid (CPA)-derived alkaloids bearing a rigid and sterically congested hexacyclic indole–tetrahydrofuran–tetramate scaffold, isolated from the endophytic fungus Aspergillus vesicolor. Apergillines A–C represent a new subclass of CPA-derived alkaloids, and aspergillines B and E possess a butanoic acid methyl ester moiety. The structures, including absolute configuration, were elucidated by interpretation of the NMR, X-ray crystallographic, and circular dichroism data. All compounds displayed anti-TMV and cytotoxic activities.