Document Detail


Fragmentation characteristics and isomeric differentiation of flavonol O-rhamnosides using negative ion electrospray ionization tandem mass spectrometry.
MedLine Citation:
PMID:  23280977     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
RATIONALE: Flavonoids exhibit a wide range of biological activities. The differentiation and structural characterization of the flavonol O-rhamnosides and their isomers are important research topics. Electrospray ionization tandem mass spectrometry (ESI-MS(n) ) is an indispensable tool and has become an efficient method for the identification of bioactive natural products.
METHODS: Negative ion ESI-MS(n) was used to characterize and differentiate flavonol O-rhamnosides and their isomeric compounds. The collision energies in collision-induced dissociation were varied to optimize the structural information.
RESULTS: Flavonol 7-O-rhamnosides containing either a hydroxyl or a methoxyl group at the C-8 position clearly differed from their isomeric compounds, such as the flavonol 3-O-rhamnosides, in the product ion spectra of the [M-H](-) ions. The differences in the locations of the glycosyl group and OCH(3) group resulted in a significant change in the relative abundances of the Y(0)(-) and [Y(0) -H](-•) ions, and the formation of some characteristic ions, such as (1,3)A(0)(-) and [(1,3)A(0)-CH(3)](-•).
CONCLUSIONS: An efficient ESI-MS(n) method for the structural identification and isomeric differentiation of flavonol O-rhamnosides was developed. The differences in the glycosyl type, and the glycosylation and methoxylation positions in the structures of isomeric flavonoids, can be determined using (-)ESI-MS(n) spectra. The formation and relative abundances of [Y(0)-H](-•) and Y(0) (-) ions, as well as the comparison of some diagnostic ions, are vital in the differentiation of isomeric flavonoids. These results have practical applications in the rapid identification of flavonol O-rhamnosides present in crude bioactive extracts.
Authors:
Keyume Ablajan; Anagu Tuoheti
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Rapid communications in mass spectrometry : RCM     Volume:  27     ISSN:  1097-0231     ISO Abbreviation:  Rapid Commun. Mass Spectrom.     Publication Date:  2013 Feb 
Date Detail:
Created Date:  2013-01-02     Completed Date:  2013-06-03     Revised Date:  2013-06-07    
Medline Journal Info:
Nlm Unique ID:  8802365     Medline TA:  Rapid Commun Mass Spectrom     Country:  England    
Other Details:
Languages:  eng     Pagination:  451-60     Citation Subset:  IM    
Copyright Information:
Copyright © 2012 John Wiley & Sons, Ltd.
Affiliation:
Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uyghur Autonomous Region, College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi, 830046, P.R. China. ablajan209@hotmail.com
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MeSH Terms
Descriptor/Qualifier:
Flavonoids / analysis,  chemistry*
Glycosides / analysis,  chemistry*
Ions / chemistry
Isomerism
Plant Extracts / chemistry
Rhodiola / chemistry
Spectrometry, Mass, Electrospray Ionization / methods*
Tandem Mass Spectrometry / methods*
Chemical
Reg. No./Substance:
0/Flavonoids; 0/Glycosides; 0/Ions; 0/Plant Extracts

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