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Identification and characterization of two Isatis indigotica O-methyltransferases methylating C-glycosylflavonoids

文献类型： 外文期刊

作者： Tan, Yuping 1 ; Yang, Jian 1 ; Jiang, Yinyin 1 ; Sun, Shufu 1 ; Wei, Xiaoyan 1 ; Wang, Ruishan 1 ; Bu, Junling 1 ; Li, Dayong 5 ; Kang, Liping 1 ; Chen, Tong 1 ; Guo, Juan 1 ; Cui, Guanghong 1 ; Tang, Jinfu 1 ; Huang, Luqi 1 ;

作者机构： 1.China Acad Chinese Med Sci, Natl Resource Ctr Chinese Mat Med, State Key Lab Dao Di Herbs, Beijing 100700, Peoples R China

2.Shenyang Pharmaceut Univ, Sch Tradit Chinese Med, Shenyang 117004, Peoples R China

3.Anhui Univ Chinese Med, Sch Pharm, Hefei 230012, Peoples R China

4.Jilin Agr Univ, Coll Chinese Med Mat, Changchun 130118, Peoples R China

5.Beijing Acad Agr & Forestry Sci, Natl Engn Res Ctr Vegetables, Beijing Vegetable Res Ctr, Beijing 100097, Peoples R China

期刊名称：HORTICULTURE RESEARCH （ 2021影响因子：7.291； 五年影响因子：7.487 ）

ISSN： 2662-6810

年卷期： 2022 年 9 卷

页码：

收录情况： SCI

摘要： Isatis indigotica accumulates several active substances, including C-glycosylflavonoids, which have important pharmacological activities and health benefits. However, enzymes catalyzing the methylation step of C-glycosylflavonoids in I. indigotica remain unknown. In this study, three O-methyltransferases (OMTs) were identified from I. indigotica that have the capacity for O-methylation of the C-glycosylflavonoid isoorientin. The Type II OMTs IiOMT1 and IiOMT2 efficiently catalyze isoorientin to form isoscoparin, and decorate one of the aromatic vicinal hydroxyl groups on flavones and methylate the C6, C8, and 3'-hydroxyl positions to form oroxylin A, wogonin, and chrysoeriol, respectively. However, the Type I OMT IiOMT3 exhibited broader substrate promiscuity and methylated the C7 and 3'-hydroxyl positions of flavonoids. Further site-directed mutagenesis studies demonstrated that five amino acids of IiOMT1/IiOMT2 (D121/D100, D173/D149, A174/A150R, N200/N176, and D248/D233) were critical residues for their catalytic activity. Additionally, only transient overexpression of Type II OMTs IiOMT1 and IiOMT2 in Nicotiana benthamiana significantly increased isoscoparin accumulation, indicating that the Type II OMTs IiOMT1 and IiOMT2 could catalyze the methylation step of C-glycosylflavonoid, isoorientin at the 3'-hydroxyl position. This study provides insights into the biosynthesis of methylated C-glycosylflavonoids, and IiOMTs could be promising catalysts in the synthesis of bioactive compounds.

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