Key Laboratory of Systems Microbial Biotechnology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, Tianjin 300308, China.
Org Lett. 2021 Apr 2;23(7):2455-2459. doi: 10.1021/acs.orglett.1c00360. Epub 2021 Mar 17.
Shikonin and -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.
紫酮和 - 对映体萘醌衍生物是许多紫草科物种中的重要成分。我们报告说，细胞色素 P450 单加氧酶（CYPs）来自一个新的 CYP82AR 亚家族，催化异戊烯侧链 C-1'位置的去氧紫草酮的羟化。在四种紫草科植物的每个物种中都发现了两个同源物。一种 CYP 优先将去氧紫草酮转化为紫草酮，而另一种则对映选择性地将去氧紫草酮羟化为萘醌。这一发现可能是紫草/萘醌产生的紫草科植物的一个普遍特征。
