Hydroxylation of Longiborneol by a Clm2-Encoded CYP450 Monooxygenase to Produce Culmorin in Fusarium graminearum

被引：29

作者：

Bahadoor, Adilah ^{[1
]}

Schneiderman, Danielle ^{[1
]}

Gemmill, Larissa ^{[1
]}

Bosnich, Whynn ^{[1
]}

Blackwell, Barbara ^{[1
]}

Melanson, Jeremy E. ^{[2
]}

McRae, Garnet ^{[2
]}

Harris, Linda J. ^{[1
]}

机构：

[1] Agr & Agri Food Canada, Ottawa Res & Dev Ctr, Ottawa, ON K1A 0C6, Canada

[2] Natl Res Council Canada, Measurement Sci & Stand, Ottawa, ON K1A 0R6, Canada

来源：

JOURNAL OF NATURAL PRODUCTS | 2016年 / 79卷 / 01期

关键词：

TARGETED GENE REPLACEMENT; TRICHOTHECENE BIOSYNTHESIS; SECONDARY METABOLITES; HEAD BLIGHT; WHEAT; VIRULENCE; CHEMISTRY; REVEALS; FUNGI;

D O I：

10.1021/acs.jnatprod.5b00676

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

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 Delta Clm2 mutants. Culmorin production resumed in a Delta Clm2 complementation experiment. A detailed analysis of the secondary metabolites extracted from the large-scale liquid culture of disruptant Delta Clm2D20 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.

引用

页码：81 / 88

页数：8

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