Hydroxylation of longiborneol by a Clm2-encoded CYP450 monooxygenase to produce culmorin in Fusarium graminearum

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DOIResolve DOI: https://doi.org/10.1021/acs.jnatprod.5b00676
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Name affiliation
  1. National Research Council Canada. Measurement Science and Standards
FormatText
TypeArticle
Journal titleJournal of Natural Products
ISSN0163-3864
1520-6025
Abstract
A second structural gene required for culmorin biosynthesis in the plant pathogen Fusarium graminearum is described. Clm2 encodes a regio- and stereoselective cytochrome P450 monooxygenase for C-11 of longiborneol. Clm2 gene disruptants were grown in liquid culture and assessed for culmorin production via HPLC-evaporative light scattering detection. The analysis indicated a complete loss of culmorin from the liquid culture of the ΔClm2 mutants. Culmorin production resumed in a ΔClm2 complementation experiment. A detailed analysis of the secondary metabolites extracted from the large-scale liquid culture of disruptant ΔClm2D20 revealed five new natural products: 3-hydroxylongiborneol, 5-hydroxylongiborneol, 12-hydroxylongiborneol, 15-hydroxylongiborneol, and 11-epi-acetylculmorin. The structures of the new compounds were elucidated by a combination of HRMS, 1D and 2D NMR, and X-ray crystallography.
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LanguageEnglish
Peer reviewedYes
NPARC number21277245
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Record identifier1f5fac78-bcd8-4996-be7a-d8f4613c29d3
Record created2016-01-21
Record modified2016-05-09
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