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.

Citation

Szwalbe, A. J., Williams, K., O'Flynn, D. E., Bailey, A. M., Mulholland, N. P., Vincent, J. L., …Simpson, T. J. (2015). Novel nonadride, heptadride and maleic acid metabolites from the byssochlamic acid producer Byssochlamys fulva IMI 40021-an insight into the biosynthesis of maleidrides. Chemical Communications, 51(96), 17088-17091. https://doi.org/10.1039/c5cc06988b

• 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