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Diverse triterpene skeletons are derived from the expansion and divergent evolution of 2,3-oxidosqualene cyclases in plants

文献类型： 外文期刊

作者： Wang, Jing 1 ; Guo, Yanhong 1 ; Yin, Xue 1 ; Wang, Xiaoning 4 ; Qi, Xiaoquan 5 ; Xue, Zheyong 1 ;

作者机构： 1.Northeast Forestry Univ, Minist Educ, Key Lab Saline Alkali Vegetat Ecol Restorat, Harbin, Peoples R China

2.Northeast Forestry Univ, Heilongjiang Key Lab Plant Bioact Subst Biosynthe, Harbin, Peoples R China

3.Beijing Acad Agr & Forestry Sci, Inst Forestry & Pomol, Beijing, Peoples R China

4.Shandong Univ, Sch Pharmaceut Sci, Minist Educ, Dept Nat Prod Chem,Key Lab Chem Biol, Jinan, Peoples R China

5.Chinese Acad Sci, Inst Bot, Key Lab Plant Mol Physiol, Beijing, Peoples R China

关键词： Triterpene; oxidosqualene cyclase; functional divergence; catalytic mechanism; biosynthesis

期刊名称：CRITICAL REVIEWS IN BIOCHEMISTRY AND MOLECULAR BIOLOGY （ 影响因子：8.25； 五年影响因子：9.0 ）

ISSN： 1040-9238

年卷期：

页码：

收录情况： SCI

摘要： Triterpenoids are one of the largest groups of secondary metabolites and exhibit diverse structures, which are derived from C30 skeletons that are biosynthesized via the isoprenoid pathway by cyclization of 2,3-oxidosqualene. Triterpenoids have a wide range of biological activities, and are used in functional foods, drugs, and as industrial materials. Due to the low content levels in their native plants and limited feasibility and efficiency of chemical synthesis, heterologous biosynthesis of triterpenoids is the most promising strategy. Herein, we classified 121 triterpene alcohols/ketones according to their conformation and ring numbers, among which 51 skeletons have been experimentally characterized as the products of oxidosqualene cyclases (OSCs). Interestingly, 24 skeletons that have not been reported from nature source were generated by OSCs in heterologous expression. Comprehensive evolutionary analysis of the identified 152 OSCs from 75 species in 25 plant orders show that several pentacyclic triterpene synthases repeatedly originated in multiple plant lineages. Comparative analysis of OSC catalytic reaction revealed that stabilization of intermediate cations, steric hindrance, and conformation of active center amino acid residues are primary factors affecting triterpene formation. Optimization of OSC could be achieved by changing of side-chain orientations of key residues. Recently, methods, such as rationally design of pathways, regulation of metabolic flow, compartmentalization engineering, etc., were introduced in improving chassis for the biosynthesis of triterpenoids. We expect that extensive study of natural variation of large number of OSCs and catalytical mechanism will provide basis for production of high level of triterpenoids by application of synthetic biology strategies.

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