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Application of positive and negative electrospray ionization, collision-induced dissociation and tandem mass spectrometry to a study of the fragmentation of 6-hydroxyluteolin 7-O-glucoside and 7-O-glucosyl-(1 --> 3)-glucoside.
Rapid Commun Mass Spectrom. 2005; 19(19):2734-42.RC

Abstract

Mass spectrometric methodology based on the combined use of positive and negative electrospray ionization, collision-induced dissociation (CID) and tandem mass spectrometry (MS/MS) has been applied to the structural characterization of 6-hydroxyluteolin 7-O-glucoside and 7-O-glucosyl-(1 --> 3)-glucoside. In-source fragmentation of both glycosides at an increased potential yielded the protonated and deprotonated aglycone, allowing CID spectra to be obtained. The differentiation between quercetin and 6-hydroxyluteolin aglycones was achieved by product ion analysis of the protonated and deprotonated aglycone (m/z 303 and 301), that showed the characteristic product ions (1,3)A at m/z 151 and 153 for quercetin, and m/z 167 and 169 for 6-hydroxyluteolin, consistent with the trihydroxylated A-ring skeleton. In the negative ion mode both glycosides were shown to undergo collision-induced homolytic and heterolytic cleavages of the O-glycosidic bond producing the aglycone radical-anion [Y0-H]-* and Y0(-) product ions. At lower collision energy, various fragmentations involving the glucose moieties were observed with a relatively higher abundance for the monoglucoside compared to the diglucoside. In the latter case both the inner and the terminal glucose residues were involved in the fragmentations, giving useful information on the 1 --> 3 interglycosidic linkage. CID MS/MS analysis of the sodiated molecules gave complementary information for the structural characterization of the studied compounds. Fragmentation mechanisms are proposed for the observed product ions.

Authors+Show Affiliations

Unité de Phytopharmacie et Médiateurs Chimiques, INRA, Route de Saint-Cyr, 78026 Versailles Cedex, France. nouressafi@yahoo.frNo affiliation info availableNo affiliation info available

Pub Type(s)

Comparative Study
Evaluation Study
Journal Article

Language

eng

PubMed ID

16136518

Citation

Es-Safi, Nour-Eddine, et al. "Application of Positive and Negative Electrospray Ionization, Collision-induced Dissociation and Tandem Mass Spectrometry to a Study of the Fragmentation of 6-hydroxyluteolin 7-O-glucoside and 7-O-glucosyl-(1 --> 3)-glucoside." Rapid Communications in Mass Spectrometry : RCM, vol. 19, no. 19, 2005, pp. 2734-42.
Es-Safi NE, Kerhoas L, Ducrot PH. Application of positive and negative electrospray ionization, collision-induced dissociation and tandem mass spectrometry to a study of the fragmentation of 6-hydroxyluteolin 7-O-glucoside and 7-O-glucosyl-(1 --> 3)-glucoside. Rapid Commun Mass Spectrom. 2005;19(19):2734-42.
Es-Safi, N. E., Kerhoas, L., & Ducrot, P. H. (2005). Application of positive and negative electrospray ionization, collision-induced dissociation and tandem mass spectrometry to a study of the fragmentation of 6-hydroxyluteolin 7-O-glucoside and 7-O-glucosyl-(1 --> 3)-glucoside. Rapid Communications in Mass Spectrometry : RCM, 19(19), 2734-42.
Es-Safi NE, Kerhoas L, Ducrot PH. Application of Positive and Negative Electrospray Ionization, Collision-induced Dissociation and Tandem Mass Spectrometry to a Study of the Fragmentation of 6-hydroxyluteolin 7-O-glucoside and 7-O-glucosyl-(1 --> 3)-glucoside. Rapid Commun Mass Spectrom. 2005;19(19):2734-42. PubMed PMID: 16136518.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Application of positive and negative electrospray ionization, collision-induced dissociation and tandem mass spectrometry to a study of the fragmentation of 6-hydroxyluteolin 7-O-glucoside and 7-O-glucosyl-(1 --> 3)-glucoside. AU - Es-Safi,Nour-Eddine, AU - Kerhoas,Lucien, AU - Ducrot,Paul-Henri, PY - 2005/9/2/pubmed PY - 2005/11/8/medline PY - 2005/9/2/entrez SP - 2734 EP - 42 JF - Rapid communications in mass spectrometry : RCM JO - Rapid Commun Mass Spectrom VL - 19 IS - 19 N2 - Mass spectrometric methodology based on the combined use of positive and negative electrospray ionization, collision-induced dissociation (CID) and tandem mass spectrometry (MS/MS) has been applied to the structural characterization of 6-hydroxyluteolin 7-O-glucoside and 7-O-glucosyl-(1 --> 3)-glucoside. In-source fragmentation of both glycosides at an increased potential yielded the protonated and deprotonated aglycone, allowing CID spectra to be obtained. The differentiation between quercetin and 6-hydroxyluteolin aglycones was achieved by product ion analysis of the protonated and deprotonated aglycone (m/z 303 and 301), that showed the characteristic product ions (1,3)A at m/z 151 and 153 for quercetin, and m/z 167 and 169 for 6-hydroxyluteolin, consistent with the trihydroxylated A-ring skeleton. In the negative ion mode both glycosides were shown to undergo collision-induced homolytic and heterolytic cleavages of the O-glycosidic bond producing the aglycone radical-anion [Y0-H]-* and Y0(-) product ions. At lower collision energy, various fragmentations involving the glucose moieties were observed with a relatively higher abundance for the monoglucoside compared to the diglucoside. In the latter case both the inner and the terminal glucose residues were involved in the fragmentations, giving useful information on the 1 --> 3 interglycosidic linkage. CID MS/MS analysis of the sodiated molecules gave complementary information for the structural characterization of the studied compounds. Fragmentation mechanisms are proposed for the observed product ions. SN - 0951-4198 UR - https://www.unboundmedicine.com/medline/citation/16136518/Application_of_positive_and_negative_electrospray_ionization_collision_induced_dissociation_and_tandem_mass_spectrometry_to_a_study_of_the_fragmentation_of_6_hydroxyluteolin_7_O_glucoside_and_7_O_glucosyl__1___>_3__glucoside_ L2 - https://doi.org/10.1002/rcm.2122 DB - PRIME DP - Unbound Medicine ER -