Novel nonadride, heptadride and maleic acid metabolites from the byssochlamic acid producer Byssochlamys fulva IMI 40021 – an insight into the biosynthesis of maleidrides. Issue 96 (9th October 2015)

• Record Type: Journal Article
• Authors: Szwalbe, Agnieszka J.; Williams, Katherine; O'Flynn, Daniel E.; Bailey, Andrew M.; Mulholland, Nicholas P.; Vincent, Jason L.; Willis, Christine L.; Cox, Russell J.; Simpson, Thomas J.
• Is Part Of: Chemical communications. Volume 51:Issue 96(2015)
• Page Start: 17088
• Page End: 17091
• Publication Date: 2015-10-09
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c5cc06988b
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Byssochlamic acid and the novel heptadride, agnestadride A are biosynthesised via alternative dimerisations of a maleic acid monomer. 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.