Hydroxylation of Longiborneol by a Clm2-Encoded CYP450 Monooxygenase to Produce Culmorin in Fusarium graminearum
Hydroxylation of Longiborneol by a Clm2-Encoded CYP450 Monooxygenase to Produce Culmorin in Fusarium graminearum
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DOI：
10.1021/acs.jnatprod.5b00676
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发表时间：
2016-01-01
影响因子：
5.1
通讯作者：
Harris, Linda J.
中科院分区：
文献类型：
--
作者：
Bahadoor, Adilah;Schneiderman, Danielle;Harris, Linda J.
描述了植物病原菌禾谷镰刀菌素生物合成所需的第二个结构基因。Clm2编码龙脑C-11的区域和立体选择性细胞色素P450单加氧酶(1)。在液体培养中培养ClM2基因干扰物，并通过高效液相-蒸发光散射检测来评估Cumorin的产生。分析表明，DeltaClm2突变体的液体培养完全丧失了culmorin(2)。库尔莫林的生产在Delta Clm2补充试验中恢复。对DeltaClm2D20的大规模液体培养提取的次生代谢物进行了详细的分析，发现了5个新的天然产物：3-羟基龙脑(3)、5-羟基龙脑(4)、12-羟基龙脑(5)、15-羟基龙脑(6)和11-表乙酰降冰片素(7)。新化合物的结构经高分辨MS、一维和二维核磁共振、X-射线单晶确证。
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.