Novel nonadride, heptadride and maleic acid metabolites from the byssochlamic acid producer Byssochlamys fulva IMI 40021-an insight into the biosynthesis of maleidrides

Szwalbe, Agnieszka J; Williams, Katherine; O'Flynn, Daniel E; Bailey, Andy M; Mulholland, Nicholas P; Vincent, Jason L; Willis, Chris L; Cox, Russell J; Simpson, Thomas J

Abstract

The filamentous fungus Byssochlamys fulva strain IMI 40021 produces (+)-byssochlamic acid 1, its novel dihydroanalogue 2 and four related secondary metabolites. Agnestadrides A, 17 and B, 18 constitute a novel class of seven-membered ring, maleic anhydride-containing (hence termed heptadride) natural products. The putative maleic anhydride precursor 5 for both nonadride and heptadride biosynthesis was isolated as a fermentation product for the first time and its structure confirmed by synthesis. Acid 5 undergoes facile decarboxylation to anhydride 6. The generic term maleidrides is proposed to encompass biosynthetically-related compounds containing maleic anhydride moieties fused to an alicyclic ring, varying in size and substituents.

• Journal Article Type: Article
• Acceptance Date: Oct 2, 2015
• Online Publication Date: Oct 2, 2015
• Publication Date: Dec 14, 2015
• Deposit Date: Apr 11, 2024
• Publicly Available Date: Apr 12, 2024
• Journal: Chemical Communications
• Print ISSN: 1359-7345
• Electronic ISSN: 1364-548X
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 51
• Issue: 96
• Pages: 17088-17091
• DOI: https://doi.org/10.1039/c5cc06988b
• Public URL: https://uwe-repository.worktribe.com/output/11881342
• Publisher URL: http://dx.doi.org/10.1039/C5CC06988B