title: 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.
authors.affiliation: School of Chemistry, Bristol University, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Agnieszka J
authors.initials: AJ
authors.lastname: Szwalbe
authors.affiliation: School of Chemistry, Bristol University, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Katherine
authors.initials: K
authors.lastname: Williams
authors.affiliation: School of Chemistry, Bristol University, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Daniel E
authors.initials: DE
authors.lastname: O'Flynn
authors.affiliation: School of Biological Sciences, University of Bristol, Bristol Life Sciences Building, 24 Tyndall Avenue, Bristol, BS8 1TQ, UK.
authors.forename: Andrew M
authors.initials: AM
authors.lastname: Bailey
authors.affiliation: Syngenta, Jealott's Hill International Research Centre, Bracknell, Berkshire, RG42 6EY, UK.
authors.forename: Nicholas P
authors.initials: NP
authors.lastname: Mulholland
authors.affiliation: Syngenta, Jealott's Hill International Research Centre, Bracknell, Berkshire, RG42 6EY, UK.
authors.forename: Jason L
authors.initials: JL
authors.lastname: Vincent
authors.affiliation: School of Chemistry, Bristol University, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Christine L
authors.initials: CL
authors.lastname: Willis
authors.affiliation: School of Chemistry, Bristol University, Cantock's Close, Bristol, BS8 1TS, UK and Leibniz Universität Hannover, Institute of Organic Chemistry, Schneiderberg 1B, 30167 Hannover, Germany.
authors.forename: Russell J
authors.initials: RJ
authors.lastname: Cox
authors.affiliation: School of Chemistry, Bristol University, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Simpson
mesh_terms: D055323:Byssochlamys / Q000378:metabolism*; D005663:Furans / Q000737:chemistry / Q000378:metabolism*; D008298:Maleates / Q000737:chemistry / Q000378:metabolism*; D008299:Maleic Anhydrides / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure
chemical_list: D005663:Furans; D008298:Maleates; D008299:Maleic Anhydrides; C010875:byssochlamic acid; C030272:maleic acid