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Issue 54, 2019
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O-Methylation steps during strobilurin and bolineol biosynthesis

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Abstract

Strobilurins are potent antifungal polyketides produced by basidiomycete fungi. Two genes encoding O-methyltransferases (O-MeT) are present in the biosynthetic gene cluster of strobilurin A 1. In previous studies, the two O-MeT enzymes Str2 and Str3 were found to catalyse the final steps of the biosynthesis of 1. Here, we show by in vivo expression experiments, that O-methylation during strobilurin biosynthesis is regiospecific. O-MeT Str2 acts first and selectively catalyses the methylation of the carboxyl group of strobilurin and bolineol precursors. Str3 catalyses the subsequent methyl transfer to the enol group to form strobilurin A 1, but cannot methylate bolineol 4. Toxicity tests showed increasing antifungal activity of intermediates through the pathway and that bolineol 4 shows antifungal activity against A. oryzae NSAR1 with an MIC of 0.1 mg ml−1.

Graphical abstract: O-Methylation steps during strobilurin and bolineol biosynthesis

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Supplementary files

Article information


Submitted
16 Aug 2019
Accepted
20 Sep 2019
First published
04 Oct 2019

This article is Open Access

RSC Adv., 2019,9, 31527-31531
Article type
Paper

O-Methylation steps during strobilurin and bolineol biosynthesis

K. E. Lebe and R. J. Cox, RSC Adv., 2019, 9, 31527
DOI: 10.1039/C9RA06412E

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

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    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
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    [Original citation] - Published by The Royal Society of Chemistry.

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