Tunable Transition Metal–Ligand Complexation for Enhanced Elucidation of Flavonoid Diglycosides by Electrospray Ionization Mass Spectrometry

A tunable ESI-MS/MS strategy for differentiation of flavone and flavanone diglycoside isomers based on metal complexation with auxiliary ligands is reported. The addition of a metal salt and an auxiliary ligand to a flavonoid solution results in the formation of [M(II) (flavonoid-H) auxiliary ligand...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Society for Mass Spectrometry 2007-03, Vol.18 (3), p.422-431
Main Authors: Pikulski, Michael, Aguilar, Apolonio, Brodbelt, Jennifer S.
Format: Article
Language:English
Subjects:
Chemistry
Complexation
Coordination compounds
Diagnostic systems
Differentiation
Exact sciences and technology
Flavonoids
Flavonoids - analysis
Glycosides - analysis
Ionization
Ions
Isomers
Ligands
Mass spectrometry
Metals - chemistry
Molecular Structure
Organic chemistry
Reactivity and mechanisms
Spectrometry, Mass, Electrospray Ionization
Stereoisomerism
Tandem Mass Spectrometry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A tunable ESI-MS/MS strategy for differentiation of flavone and flavanone diglycoside isomers based on metal complexation with auxiliary ligands is reported. The addition of a metal salt and an auxiliary ligand to a flavonoid solution results in the formation of [M(II) (flavonoid-H) auxiliary ligand] + complexes, where M(II) is a transition metal. A series of auxiliary ligands with electron-withdrawing substituents were synthesized to tailor the relative metal binding affinities of the ligands and thus directly influence the stabilities, and consequently the dissociation pathways, of the complexes. Upon collisionally activated dissociation, the complexes yield fragmentation patterns in which the abundances of key diagnostic ions are enhanced, thus facilitating isomer differentiation.
ISSN:1044-0305
1879-1123
DOI:10.1016/j.jasms.2006.10.011