Issue 96, 2015

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

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
19 Aug 2015
Accepted
02 Oct 2015
First published
02 Oct 2015
This article is Open Access
Creative Commons BY license

Chem. Commun., 2015,51, 17088-17091

Author version available

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

A. J. Szwalbe, K. Williams, D. E. O'Flynn, A. M. Bailey, N. P. Mulholland, J. L. Vincent, C. L. Willis, R. J. Cox and T. J. Simpson, Chem. Commun., 2015, 51, 17088 DOI: 10.1039/C5CC06988B

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