Characterization of a glycosyltransferase from Paris polyphylla for application in biosynthesis of rare ophiopogonins and ginsenosides

doi:10.1016/j.phytochem.2024.114173

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	Characterization of a glycosyltransferase from Paris polyphylla for application in biosynthesis of rare ophiopogonins and ginsenosides
	Xu, Wen-Ke; Zhao, Chen-Xiao; Yang, Xiao-Wen; Chen, Yue-Gui; Yan, Yuan-Feng; Guo, Kai; Li, Sheng-Hong; Liu, Yan; Long, Li-Ping
	2024
发表期刊	PHYTOCHEMISTRY
ISSN	0031-9422
卷号	225 页码:114173
摘要	Saponins are bioactive components of many medicinal plants, possessing complicated chemical structures and extensive pharmacological activities, but the production of high-value saponins remains challenging. In this study, a 6 '-O-glucosyltransferase PpUGT7 (PpUGT91AH7) was functionally characterized from Paris polyphylla Smith var. yunnanensis (Franch.) Hand. -Mazz., which can transfer a glucosyl group to the C-6 ' position of diosgenin-3-O-rhamnosyl-(1 -* 2)-glucoside (1), pennogenin-3-O-rhamnosyl-(1 -* 2)-glucoside (2), and diosgenin-3O-glucoside (5). The KM and Kcat values of PpUGT7 towards the substrate 2 were 8.4 mu M and 2 x 10-3 s-1, respectively. Through molecular docking and site-directed mutagenesis, eight residues were identified to interact with the sugar acceptor 2 and be crucial for enzyme activity. Moreover, four rare ophiopogonins and ginsenosides were obtained by combinatorial biosynthesis, including an undescribed compound ruscogenin-3-O-glucosyl-(1 -* 6)-glucoside (10). Firstly, two monoglycosides 9 and 11 were generated using a known sterol 3-O beta-glucosyltransferase PpUGT80A40 with ruscogenin (7) and 20(S)-protopanaxadiol (8) as substrates, which were further glycosylated to the corresponding diglycosides 10 and 12 under the catalysis of PpUGT7. In addition, compounds 7-11 were found to show inhibitory effects on the secretion of TNF-alpha and IL-6 in macrophages RAW264.7. The findings provide valuable insights into the enzymatic glycosylation processes in the biosynthesis of bioactive saponins in P. polyphylla var. yunnanensis, and also serve as a reference for utilizing UDPglycosyltransferases to construct high-value or rare saponins for development of new therapeutic agents.
DOI	10.1016/j.phytochem.2024.114173
WOS记录号	WOS:001253298700001
引用统计	被引频次：3[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/76387
专题	中国科学院昆明植物研究所
推荐引用方式 GB/T 7714	Xu, Wen-Ke,Zhao, Chen-Xiao,Yang, Xiao-Wen,et al. Characterization of a glycosyltransferase from Paris polyphylla for application in biosynthesis of rare ophiopogonins and ginsenosides[J]. PHYTOCHEMISTRY,2024,225:114173.
APA	Xu, Wen-Ke.,Zhao, Chen-Xiao.,Yang, Xiao-Wen.,Chen, Yue-Gui.,Yan, Yuan-Feng.,...&Long, Li-Ping.(2024).Characterization of a glycosyltransferase from Paris polyphylla for application in biosynthesis of rare ophiopogonins and ginsenosides.PHYTOCHEMISTRY,225,114173.
MLA	Xu, Wen-Ke,et al."Characterization of a glycosyltransferase from Paris polyphylla for application in biosynthesis of rare ophiopogonins and ginsenosides".PHYTOCHEMISTRY 225(2024):114173.

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