Fusarochromene, a novel tryptophan-derived metabolite from Fusarium sacchari

James W. Marshall; Kate M. J. de Mattos-Shipley; Iman A. Y. Ghannam; Asifa Munawar; Jonathan C. Killen; Colin M. Lazarus; Russell J. Cox; Christine L. Willis; Thomas J. Simpson

doi:10.1039/D0OB02031A

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Fusarochromene, a novel tryptophan-derived metabolite from Fusarium sacchari†

James W. Marshall,

^a Kate M. J. de Mattos-Shipley,*^b Iman A. Y. Ghannam,

^ac Asifa Munawar,^b Jonathan C. Killen,^a Colin M. Lazarus,^b Russell J. Cox,

^ad Christine L. Willis

^a and Thomas J. Simpson

*^a

Author affiliations

* Corresponding authors

^a School of Chemistry, University of Bristol, Cantock's Close, Bristol, UK
E-mail: tom.simpson@bristol.ac.uk

^b School of Biological Sciences, University of Bristol, 24 Tyndall Avenue, Bristol, UK
E-mail: kd4495@bristol.ac.uk

^c Chemistry of Natural and Microbial Products Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, El-Bohouth Street, Dokki, Cairo, Egypt

^d Institute for Organic Chemistry and BMWZ, Leibniz University of Hannover, Schneiderberg 38, Hannover, Germany

Abstract

Fusarochromene isolated from the plant pathogenic fungus, Fusarium sacchari is closely related to a group of mycotoxins including fusarochromanone previously isolated from various Fusaria spp. Despite their assumed polyketide biogenesis, incorporation studies with ¹³C-labelled acetate, glycerol and tryptophans show that fusarochromene is unexpectedly derived via oxidative cleavage of the aromatic amino acid tryptophan. A putative biosynthetic gene cluster has been identified.

This article is part of the themed collection: Chemical Biology in OBC

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DOI: https://doi.org/10.1039/D0OB02031A
Article type: Paper
Submitted: 05 Oct 2020
Accepted: 22 Oct 2020
First published: 23 Oct 2020
This article is Open Access

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Org. Biomol. Chem., 2021,19, 182-187

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Fusarochromene, a novel tryptophan-derived metabolite from Fusarium sacchari

J. W. Marshall, K. M. J. de Mattos-Shipley, I. A. Y. Ghannam, A. Munawar, J. C. Killen, C. M. Lazarus, R. J. Cox, C. L. Willis and T. J. Simpson, Org. Biomol. Chem., 2021, 19, 182 DOI: 10.1039/D0OB02031A

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Organic & Biomolecular Chemistry

Fusarochromene, a novel tryptophan-derived metabolite from Fusarium sacchari†

Abstract

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Fusarochromene, a novel tryptophan-derived metabolite from Fusarium sacchari

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