Details
| Original language | English |
|---|---|
| Pages (from-to) | 31527-31531 |
| Number of pages | 5 |
| Journal | RSC Advances |
| Volume | 9 |
| Issue number | 54 |
| Early online date | 4 Oct 2019 |
| Publication status | Published - 2019 |
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.
ASJC Scopus subject areas
- Chemistry(all)
- General Chemistry
- Chemical Engineering(all)
- General Chemical Engineering
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In: RSC Advances, Vol. 9, No. 54, 2019, p. 31527-31531.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - O-Methylation steps during strobilurin and bolineol biosynthesis
AU - Lebe, Karen E.
AU - Cox, Russell J.
N1 - Funding information: KEL thanks the Leibniz Universität Hannover for funding. DFG is thanked for the provision of LCMS and NMR equipment (INST 187/621-1, INST 187/686-1). RJC thanks Risa No?ani for a standard sample of 1. The publication of this article was funded by the Open Access fund of Leibniz Universität Hannover.
PY - 2019
Y1 - 2019
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85073426199&partnerID=8YFLogxK
U2 - 10.1039/c9ra06412e
DO - 10.1039/c9ra06412e
M3 - Article
AN - SCOPUS:85073426199
VL - 9
SP - 31527
EP - 31531
JO - RSC Advances
JF - RSC Advances
SN - 2046-2069
IS - 54
ER -