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Uncovering biosynthetic relationships between antifungal nonadrides and octadrides
Authors
Andrew M. Bailey
Russell J. Cox
+11 more
Trong T. Dao
Kate M. J. De Mattos-Shipley
Claudio Greco
David M. Heard
Nicholas P. Mulholland
Daniel E. O'Flynn
Thomas J. Simpson
Zhongshu Song
Catherine E. Spencer
Jason L. Vincent
Christine L. Willis
Publication date
1 January 2020
Publisher
Cambridge : RSC
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Cite
Abstract
Maleidrides are a class of bioactive secondary metabolites unique to filamentous fungi, which contain one or more maleic anhydrides fused to a 7-, 8- or 9- membered carbocycle (named heptadrides, octadrides and nonadrides respectively). Herein structural and biosynthetic studies on the antifungal octadride, zopfiellin, and nonadrides scytalidin, deoxyscytalidin and castaneiolide are described. A combination of genome sequencing, bioinformatic analyses, gene disruptions, biotransformations, isotopic feeding studies, NMR and X-ray crystallography revealed that they share a common biosynthetic pathway, diverging only after the nonadride deoxyscytalidin. 5-Hydroxylation of deoxyscytalidin occurs prior to ring contraction in the zopfiellin pathway of Diffractella curvata. In Scytalidium album, 6-hydroxylation-confirmed as being catalysed by the α-ketoglutarate dependent oxidoreductase ScyL2-converts deoxyscytalidin to scytalidin, in the final step in the scytalidin pathway. Feeding scytalidin to a zopfiellin PKS knockout strain led to the production of the nonadride castaneiolide and two novel ring-open maleidrides. © The Royal Society of Chemistry
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Institutionelles Repositorium der Leibniz Universität Hannover
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Last time updated on 01/11/2022