CYP82AR Subfamily Proteins Catalyze C-1′ Hydroxylations of Deoxyshikonin in the Biosynthesis of Shikonin and Alkannin,Organic Letters

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CYP82AR Subfamily Proteins Catalyze C-1′ Hydroxylations of Deoxyshikonin in the Biosynthesis of Shikonin and Alkannin
Organic Letters ( IF 4.9 ) Pub Date : 2021-03-17 , DOI: 10.1021/acs.orglett.1c00360
Wan Song ₁ , Yibin Zhuang ₁ , Tao Liu ₁

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Shikonin and S-enantiomer alkannin are important naphthoquinone derivatives present in many Boraginaceae species. We report that cytochrome P450 monooxygenases (CYPs) from a new CYP82AR subfamily catalyzed hydroxylations of deoxyshikonin at C-1′ position of isoprenoid side chain. Two homologues were discovered from each species of the four Boraginaceae plants. One CYP preferred converting deoxyshikonin into shikonin, and the other stereoselectively hydroxylated deoxyshikonin into alkannin. The discovery might be a general feature of shikonin/alkannin-producing Boraginaceae plants.

中文翻译：

CYP82AR 亚家族蛋白在紫草素和 Alkannin 的生物合成中催化脱氧紫草素的 C-1' 羟基化

Shikonin和S-对映异构体 alkannin 是重要的萘醌衍生物，存在于许多紫草科物种中。我们报告说，来自新 CYP82AR 亚家族的细胞色素 P450 单加氧酶 (CYPs) 在类异戊二烯侧链的 C-1' 位置催化脱氧紫草素的羟基化。从四种紫草科植物的每个物种中发现了两个同源物。一种 CYP 倾向于将脱氧紫草素转化为紫草素，而另一种则通过立体选择性羟基化脱氧紫草素转化为烷酸。这一发现可能是产生紫草素/烷宁的紫草科植物的一个普遍特征。

更新日期：2021-04-02

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