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

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

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

17 Citations (Scopus)
366 Downloads (Pure)

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.
Original languageEnglish
Pages (from-to)17088-17091
Number of pages4
JournalChemical Communications
Volume51
Issue number96
Early online date2 Oct 2015
DOIs
Publication statusPublished - 14 Dec 2015

Structured keywords

  • BCS and TECS CDTs

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