Hydroxylation of Longiborneol by a Clm2-Encoded CYP450 Monooxygenase to Produce Culmorin in Fusarium graminearum
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- 作者：Adilah Bahadoor ; Danielle Schneiderman ; Larissa Gemmill ; Whynn Bosnich ; Barbara Blackwell ; Jeremy E. Melanson ; Garnet McRae ; Linda J. Harris
- 刊名：Journal of Natural Products
- 出版年：2016
- 出版时间：January 22, 2016
- 年：2016
- 卷：79
- 期：1
- 页码：81-88
- 全文大小：450K
- ISSN：1520-6025
文摘
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 (1). 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 (2) 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 (3), 5-hydroxylongiborneol (4), 12-hydroxylongiborneol (5), 15-hydroxylongiborneol (6), and 11-epi-acetylculmorin (7). The structures of the new compounds were elucidated by a combination of HRMS, 1D and 2D NMR, and X-ray crystallography.