Repeated evolution of cytochrome P450-mediated spiroketal steroid biosynthesis in plants.,Nature Communications

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Repeated evolution of cytochrome P450-mediated spiroketal steroid biosynthesis in plants.
Nature Communications ( IF 14.7 ) Pub Date : 2019-07-19 , DOI: 10.1038/s41467-019-11286-7
Bastien Christ _{1,

2} , Chengchao Xu ₁ , Menglong Xu ₁ , Fu-Shuang Li ₁ , Naoki Wada ₃ , Andrew J Mitchell ₁ , Xiu-Lin Han ₄ , Meng-Liang Wen ₄ , Makoto Fujita _{3,

5} , Jing-Ke Weng _{1,

6}

Affiliation

Diosgenin is a spiroketal steroidal natural product extracted from plants and used as the single most important precursor for the world steroid hormone industry. The sporadic occurrences of diosgenin in distantly related plants imply possible independent biosynthetic origins. The characteristic 5,6-spiroketal moiety in diosgenin is reminiscent of the spiroketal moiety present in anthelmintic avermectins isolated from actinomycete bacteria. How plants gained the ability to biosynthesize spiroketal natural products is unknown. Here, we report the diosgenin-biosynthetic pathways in himalayan paris (Paris polyphylla), a monocot medicinal plant with hemostatic and antibacterial properties, and fenugreek (Trigonella foenum-graecum), an eudicot culinary herb plant commonly used as a galactagogue. Both plants have independently recruited pairs of cytochromes P450 that catalyze oxidative 5,6-spiroketalization of cholesterol to produce diosgenin, with evolutionary progenitors traced to conserved phytohormone metabolism. This study paves the way for engineering the production of diosgenin and derived analogs in heterologous hosts.

中文翻译：

植物中细胞色素P450介导的螺酮类固醇生物合成的反复进化。

薯gen皂素是一种从植物中提取的螺状甾体类天然产物，被用作世界类固醇激素行业最重要的单一前体。薯related皂素在远缘植物中的零星出现暗示可能是独立的生物合成来源。薯gen皂苷元中特征性的5,6-螺酮基部分让人想起从放线菌中分离出的驱虫性阿维菌素中的螺酮基部分。植物如何获得生物合成螺旋体天然产物的能力尚不清楚。在这里，我们报道了具有止血和抗菌特性的单子叶药用植物喜马拉雅巴黎（Paris polyphylla）和葫芦巴（Trigonella foenum-graecum）（一种常用作催乳剂的双子叶植物烹饪植物）中薯gen皂甙元的生物合成途径。两种植物都独立招募了成对的细胞色素P450，它们催化胆固醇的氧化5，6-螺缩酮化生成薯os皂苷元，而进化祖细胞则追踪到保守的植物激素代谢。该研究为异源宿主中薯engineering皂苷元及其衍生类似物的生产工程化铺平了道路。

更新日期：2019-07-19

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