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Characterization of non‐covalent complexes of rutin with cyclodextrins by electrospray ionization tandem mass spectrometry
Author(s) -
Guo Mingquan,
Song Fengrui,
Liu Zhiqiang,
Liu Shuying
Publication year - 2004
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.605
Subject(s) - chemistry , electrospray ionization , rutin , tandem mass spectrometry , characterization (materials science) , mass spectrometry , chromatography , protein mass spectrometry , direct electron ionization liquid chromatography–mass spectrometry interface , extractive electrospray ionization , electrospray , covalent bond , electrospray mass spectrometry , tandem , ionization , chemical ionization , organic chemistry , ion , nanotechnology , antioxidant , materials science , composite material
Electrospray ionization tandem mass spectrometry (ESI‐MS n ) and the phase solubility method were used to characterize the gas‐phase and solution‐phase non‐covalent complexes between rutin (R) and α‐, β‐ and γ‐cyclodextrins (CDs). The direct correlation between mass spectrometric results and solution‐phase behavior is thus revealed. The order of the 1 : 1 association constants ( K c ) of the complexes between R and the three CDs in solution calculated from solubility diagrams is in good agreement with the order of their relative peak intensities and relative collision‐induced dissociation (CID) energies of the complexes under the same ESI‐MS n condition in both the positive and negative ion modes. Not only the binding stoichiometry but also the relative stabilities and even binding sites of the CD–R complexes can be elucidated by ESI‐MS n . The diagnostic fragmentation of CD–R complexes, with a significant contribution of covalent fragmentation of rutin leaving the quercetin (Q) moiety attached to the CDs, provides convincing evidence for the formation of inclusion complexes between R and CDs. The diagnostic fragment ions can be partly confirmed by the complexes between Q and CDs. The gas‐phase stability order of the deprotonated CD–R complexes is β‐CD–R > α‐CD–R > γ‐CD/R; β‐CD seems to bind R more strongly than the other CDs. Copyright © 2004 John Wiley & Sons, Ltd.