The versatile O-methyltransferase LrOMT catalyzes multiple O-methylation reactions in amaryllidaceae alkaloids biosynthesis

doi:10.1016/j.ijbiomac.2019.09.011

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	The versatile O-methyltransferase LrOMT catalyzes multiple O-methylation reactions in amaryllidaceae alkaloids biosynthesis
	Li, Wei 3; Qiao, Chong 1,3; Pang, Jing 1,3; Zhang, Guolin 3; Luo, Yinggang 2,3
刊名	INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
	2019
卷号	141 页码:680-692
关键词	Amaryllidaceae alkaloids Biosynthesis O-Methyltransferase Lycoris radiata Galanthamine
ISSN号	0141-8130
DOI	10.1016/j.ijbiomac.2019.09.011
产权排序	1
文献子类	Article
英文摘要	Amaryllidaceae alkaloids are unique benzylphenethylamine derivatives that comprise of more than 600 members with a huge chemical diversity. Most of them showed interesting bioactivities, for instance, galanthamine (GAL) is clinically used for Alzheimer's disease treatment. All Amaryllidaceae alkaloids had been thought to be derived from 4'-O-methylnorbelladine originated from norbelladine catalyzed by norbelladine 4'-O-methyltransferase (N4OMT). Herein we mined the transcriptome datasets of Lycoris radiata, a GAL-producing plant. LrOMT was cloned, overexpressed in Escherichia coli, and purified to homogeneity. Bioinformatics analysis and enzymatic activity assays revealed that LrOMT is an S-adenosylmethionine-dependent Class I OMT. LrOMT exhibited both para- and meta-O-methylation activities toward norbelladine to give 4'- and 3'-O-methylnorbelladine. Twenty-four analogues, including the proposed biosynthetic intermediates, were introduced to investigate the substrate scope of LrOMT and it showed that the aromatic substrates should have two vicinal hydroxyl groups. The LrOMT-catalyzed O-methylation preference is dependent on the properties of the binding group of the substrates. The transcription levels of LrOMT were positively associated with the accumulation of the Amaryllidaceae alkaloids and the biosynthetic intermediates in L. radiata. The present work revealed that LrOMT catalyzes multiple O-methylation reactions and its characterization will be helpful to uncover novel biosynthetic genes for Amaryllidaceae alkaloids biosynthesis. (C) 2019 Elsevier B.V. All rights reserved.
学科主题	Biochemistry & Biophysics
URL标识	查看原文
WOS关键词	REGIOSELECTIVITY ; NORBELLADINE ; PRECURSORS ; SITE
WOS研究方向	Biochemistry & Molecular Biology ; Chemistry ; Polymer Science
语种	英语
出版者	ELSEVIER
WOS记录号	WOS:000506713000071
内容类型	期刊论文
源URL	[http://210.75.237.14/handle/351003/31011]
专题	国家天然药物工程技术研究中心_天然产物研究
通讯作者	Luo, Yinggang
作者单位	1.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China; 3.Chinese Acad Sci, Chengdu Inst Biol, Ctr Nat Prod Res, 9 Sect 4,Renmin Rd South, Chengdu 610041, Peoples R China;
推荐引用方式 GB/T 7714	Li, Wei,Qiao, Chong,Pang, Jing,et al. The versatile O-methyltransferase LrOMT catalyzes multiple O-methylation reactions in amaryllidaceae alkaloids biosynthesis[J]. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,2019,141:680-692.
APA	Li, Wei,Qiao, Chong,Pang, Jing,Zhang, Guolin,&Luo, Yinggang.(2019).The versatile O-methyltransferase LrOMT catalyzes multiple O-methylation reactions in amaryllidaceae alkaloids biosynthesis.INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,141,680-692.
MLA	Li, Wei,et al."The versatile O-methyltransferase LrOMT catalyzes multiple O-methylation reactions in amaryllidaceae alkaloids biosynthesis".INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES 141(2019):680-692.