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Issue 10, 2019
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Structure revision of cryptosporioptides and determination of the genetic basis for dimeric xanthone biosynthesis in fungi

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Abstract

Three novel dimeric xanthones, cryptosporioptides A–C were isolated from Cryptosporiopsis sp. 8999 and their structures elucidated. Methylation of cryptosporioptide A gave a methyl ester with identical NMR data to cryptosporioptide, a compound previously reported to have been isolated from the same fungus. However, HRMS analysis revealed that cryptosporioptide is a symmetrical dimer, not a monomer as previously proposed, and the revised structure was elucidated by extensive NMR analysis. The genome of Cryptosporiopsis sp. 8999 was sequenced and the dimeric xanthone (dmx) biosynthetic gene cluster responsible for the production of the cryptosporioptides was identified. Gene disruption experiments identified a gene (dmxR5) encoding a cytochrome P450 oxygenase as being responsible for the dimerisation step late in the biosynthetic pathway. Disruption of dmxR5 led to the isolation of novel monomeric xanthones. Cryptosporioptide B and C feature an unusual ethylmalonate subunit: a hrPKS and acyl CoA carboxylase are responsible for its formation. Bioinformatic analysis of the genomes of several fungi producing related xanthones, e.g. the widely occurring ergochromes, and related metabolites allows detailed annotation of the biosynthetic genes, and a rational overall biosynthetic scheme for the production of fungal dimeric xanthones to be proposed.

Graphical abstract: Structure revision of cryptosporioptides and determination of the genetic basis for dimeric xanthone biosynthesis in fungi

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Publication details

The article was received on 16 Nov 2018, accepted on 20 Jan 2019 and first published on 21 Jan 2019


Article type: Edge Article
DOI: 10.1039/C8SC05126G
Citation: Chem. Sci., 2019,10, 2930-2939
  • Open access: Creative Commons BY license
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    Structure revision of cryptosporioptides and determination of the genetic basis for dimeric xanthone biosynthesis in fungi

    C. Greco, K. de Mattos-Shipley, Andrew M. Bailey, N. P. Mulholland, J. L. Vincent, C. L. Willis, R. J. Cox and T. J. Simpson, Chem. Sci., 2019, 10, 2930
    DOI: 10.1039/C8SC05126G

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