An integrated strategy for the systematic characterization and discovery of new indole alkaloids from Uncaria rhynchophylla by UHPLC/DAD/LTQ-Orbitrap-MS

doi:10.1007/s00216-015-8777-0

CORC > 上海药物研究所 > 中国科学院上海药物研究所 > 上海中药现代化研究中心

	An integrated strategy for the systematic characterization and discovery of new indole alkaloids from Uncaria rhynchophylla by UHPLC/DAD/LTQ-Orbitrap-MS
	Pan, Huiqin; Yang, Wenzhi; Zhang, Yibei; Yang, Min; Feng, Ruihong; Wu, Wanying; Guo, Dean
刊名	ANALYTICAL AND BIOANALYTICAL CHEMISTRY
	2015-08
卷号	407 期号:20 页码:6057-6070
关键词	Uncaria rhynchophylla UHPLC/LTQ-Orbitrap-MS New indole alkaloid Systematic characterization Mass defect filtering
ISSN号	1618-2642
DOI	10.1007/s00216-015-8777-0
文献子类	Article
英文摘要	The exploration of new chemical entities from herbal medicines may provide candidates for the in silico screening of drug leads. However, this significant work is hindered by the presence of multiple classes of plant metabolites and many re-discovered structures. This study presents an integrated strategy that uses ultrahigh-performance liquid chromatography/linear ion-trap quadrupole/Orbitrap mass spectrometry (UHPLC/LTQ-Orbitrap-MS) coupled with in-house library data for the systematic characterization and discovery of new potentially bioactive molecules. Exploration of the indole alkaloids from Uncaria rhynchophylla (UR) is presented as a model study. Initially, the primary characterization of alkaloids was achieved using mass defect filtering and neutral loss filtering. Subsequently, phytochemical isolation obtained 14 alkaloid compounds as reference standards, including a new one identified as 16,17-dihydro-O-demethylhirsuteine by NMR analyses. The direct-infusion fragmentation behaviors of these isolated alkaloids were studied to provide diagnostic structural information facilitating the rapid differentiation and characterization of four different alkaloid subtypes. Ultimately, after combining the experimental results with a survey of an in-house library containing 129 alkaloids isolated from the Uncaria genus, a total of 92 alkaloids (60 free alkaloids and 32 alkaloid O-glycosides) were identified or tentatively characterized, 56 of which are potential new alkaloids for the Uncaria genus. Hydroxylation on ring A, broad variations in the C-15 side chain, new N-oxides, and numerous O-glycosides, represent the novel features of the newly discovered indole alkaloid structures. These results greatly expand our knowledge of UR chemistry and are useful for the computational screening of potentially bioactive molecules from indole alkaloids.
资助项目	Twelfth Five-Year National Science & Technology Support Program[2012BAI29B06] ; National Science and Technology Major Project for Major Drug Development[2013ZX09508104] ; National Science and Technology Major Project for Major Drug Development[2014ZX09304-307-001-007] ; Special Scientific Research in the Chinese Medicine Industry of State Administration of Traditional Chinese Medicine[201307002]
WOS关键词	NATURAL-PRODUCT ISOLATION ; TANDEM MASS-SPECTROMETRY ; IDENTIFICATION ; CHROMATOGRAPHY ; DEREPLICATION ; DEFECT ; FRAGMENTATION ; ACQUISITION ; METABOLITES
WOS研究方向	Biochemistry & Molecular Biology ; Chemistry
语种	英语
出版者	SPRINGER HEIDELBERG
WOS记录号	WOS:000358371200019
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/276456]
专题	上海中药现代化研究中心
通讯作者	Wu, Wanying
作者单位	Chinese Acad Sci, Shanghai Inst Mat Med, Natl Engn Lab TCM Standardizat Technol, Shanghai Res Ctr Modernizat Tradit Chinese Med, Shanghai 201203, Peoples R China
推荐引用方式 GB/T 7714	Pan, Huiqin,Yang, Wenzhi,Zhang, Yibei,et al. An integrated strategy for the systematic characterization and discovery of new indole alkaloids from Uncaria rhynchophylla by UHPLC/DAD/LTQ-Orbitrap-MS[J]. ANALYTICAL AND BIOANALYTICAL CHEMISTRY,2015,407(20):6057-6070.
APA	Pan, Huiqin.,Yang, Wenzhi.,Zhang, Yibei.,Yang, Min.,Feng, Ruihong.,...&Guo, Dean.(2015).An integrated strategy for the systematic characterization and discovery of new indole alkaloids from Uncaria rhynchophylla by UHPLC/DAD/LTQ-Orbitrap-MS.ANALYTICAL AND BIOANALYTICAL CHEMISTRY,407(20),6057-6070.
MLA	Pan, Huiqin,et al."An integrated strategy for the systematic characterization and discovery of new indole alkaloids from Uncaria rhynchophylla by UHPLC/DAD/LTQ-Orbitrap-MS".ANALYTICAL AND BIOANALYTICAL CHEMISTRY 407.20(2015):6057-6070.