UGT73F17, a new glycosyltransferase from Glycyrrhiza uralensis, catalyzes the regiospecific glycosylation of pentacyclic triterpenoids

被引：33

作者：

He, Junbin ^{[1
]}

Chen, Kuan ^{[1
]}

Hu, Zhi-min ^{[1
]}

Li, Kai ^{[1
]}

Song, Wei ^{[1
]}

Yu, Li-yan ^{[2
,3
]}

Leung, Chung-Hang ^{[4
]}

Ma, Dik-Lung ^{[5
]}

Qiao, Xue ^{[1
]}

Ye, Min ^{[1
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, 38 Xueyuan Rd, Beijing 100191, Peoples R China

[2] Chinese Acad Med Sci, Inst Med Biotechnol, Beijing 100050, Peoples R China

[3] Peking Union Med Coll, Beijing 100050, Peoples R China

[4] Univ Macau, Inst Chinese Med Sci, State Key Lab Qual Res Chinese Med, Macau, Peoples R China

[5] Hong Kong Baptist Univ, Dept Chem, Kowloon Tong, Hong Kong, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 62期

基金：

中国国家自然科学基金;

关键词：

CELL-SUSPENSION CULTURES; SAPONIN BIOSYNTHESIS; BIOACTIVE CONSTITUENTS; LIQUID-CHROMATOGRAPHY; MEDICAGO-TRUNCATULA; MASS-SPECTROMETRY; CENTELLA-ASIATICA; HERBAL MEDICINE; ACID; GLUCOSYLTRANSFERASE;

D O I：

10.1039/c8cc04215b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The regiospecific glycosylation of pentacyclic triterpenoids by UGT73F17, a new glycosyltransferase from Glycyrrhiza uralensis, is highlighted. UGT73F17 exhibited strict substrate specificity toward the carboxyl group at C-30/C-29 of pentacyclic triterpenoids, and showed high promiscuity to sugar donors. UGT73F17 represents the first identified triterpenoid 30/29-O-glycosyltransferase, and could be used as an effective biocatalyst to synthesize glycosyl ester saponins.

引用

页码：8594 / 8597

页数：4

共 35 条

[1] Genomics-based selection and functional characterization of triterpene glycosyltransferases from the model legume Medicago truncatula [J].

Achnine, L ;

Huhman, DV ;

Farag, MA ;

Sumner, LW ;

Blount, JW ;

Dixon, RA .

PLANT JOURNAL, 2005, 41 (06) :875-887

[2] UDP-Glycosyltransferases from the UGT73C Subfamily in Barbarea vulgaris Catalyze Sapogenin 3-O-Glucosylation in Saponin-Mediated Insect Resistance [J].

Augustin, Jorg M. ;

Drok, Sylvia ;

Shinoda, Tetsuro ;

Sanmiya, Kazutsuka ;

Nielsen, Jens Kvist ;

Khakimov, Bekzod ;

Olsen, Carl Erik ;

Hansen, Esben Halkjaer ;

Kuzina, Vera ;

Ekstrom, Claus Thorn ;

Hauser, Thure ;

Bak, Soren .

PLANT PHYSIOLOGY, 2012, 160 (04) :1881-1895

[3] Molecular activities, biosynthesis and evolution of triterpenoid saponins [J].

Augustin, Jorg M. ;

Kuzina, Vera ;

Andersen, Sven B. ;

Bak, Soren .

PHYTOCHEMISTRY, 2011, 72 (06) :435-457

[4] Chemical structures, production and enzymatic transformations of sapogenins and saponins from Centella asiatica (L.) Urban [J].

Azerad, Robert .

FITOTERAPIA, 2016, 114 :168-187

[5]

Ban L, 2012, NAT CHEM BIOL, V8, P769, DOI [10.1038/NCHEMBIO.1022, 10.1038/nchembio.1022]

[6] Molecular cloning of an ester-forming triterpenoid: UDP-glucose 28-O-glucosyltransferase involved in saponin biosynthesis from the medicinal plant Centella asiatica [J].

de Costa, Fernanda ;

Barber, Carla J. S. ;

Kim, Yeon-bok ;

Reed, Darwin W. ;

Zhang, Haixia ;

Fett-Neto, Arthur G. ;

Covello, Patrick S. .

PLANT SCIENCE, 2017, 262 :9-17

[7] BIOTRANSFORMATION OF 18-BETA-GLYCYRRHETINIC ACID BY CELL-SUSPENSION CULTURES OF GLYCYRRHIZA-GLABRA [J].

HAYASHI, H ;

FUKUI, H ;

TABATA, M .

PHYTOCHEMISTRY, 1990, 29 (07) :2149-2152

[8] Bioactive Constituents of Glycyrrhiza uralensis (Licorice): Discovery of the Effective Components of a Traditional Herbal Medicine [J].

Ji, Shuai ;

Li, Ziwei ;

Song, Wei ;

Wang, Yongrui ;

Liang, Wenfei ;

Li, Kai ;

Tang, Shunan ;

Wang, Qi ;

Qiao, Xue ;

Zhou, Demin ;

Yu, Siwang ;

Ye, Min .

JOURNAL OF NATURAL PRODUCTS, 2016, 79 (02) :281-292

[9] Enzymes for chemical synthesis [J].

Koeller, KM ;

Wong, CH .

NATURE, 2001, 409 (6817) :232-240

[10] Glycosyltransferases: Structures, functions, and mechanisms [J].

Lairson, L. L. ;

Henrissat, B. ;

Davies, G. J. ;

Withers, S. G. .

ANNUAL REVIEW OF BIOCHEMISTRY, 2008, 77 :521-555

← 1 2 3 4 →