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Fragmentation study of iridoid glucosides through positive and negative electrospray ionization, collision-induced dissociation and tandem mass spectrometry.
Rapid Commun Mass Spectrom. 2007; 21(7):1165-75.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 mass spectral study of a series of six naturally occurring iridoids through in-source fragmentation of the protonated [M+H]+, deprotonated [M--H]- and sodiated [M+Na]+ ions. This led to the unambiguous determination of the molecular masses of the studied compounds and allowed CID spectra of the molecular ions to be obtained. Valuable structural information regarding the nature of both the glycoside and the aglycone moiety was thus obtained. Glycosidic cleavage and ring cleavages of both aglycone and sugar moieties were the major fragmentation pathways observed during CID, where the losses of small molecules, the cinnamoyl and the cinnamate parts were also observed. The formation of the ionized aglycones, sugars and their product ions was thus obtained giving information on their basic skeleton. The protonated, i.e. [M+H]+ and deprotonated [M--H]-, ions were found to fragment mainly by glycosidic cleavages. MS/MS spectra of the [M+Na]+ ions gave complementary information for the structural characterization of the studied compounds. Unlike the dissociation of protonated molecular ions, that of sodiated molecules also provided sodiated sugar fragments where the C0+ fragment corresponding to the glucose ion was obtained as base peak for all the studied compounds.

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)

Journal Article

Language

eng

PubMed ID

17330213

Citation

Es-Safi, Nour-Eddine, et al. "Fragmentation Study of Iridoid Glucosides Through Positive and Negative Electrospray Ionization, Collision-induced Dissociation and Tandem Mass Spectrometry." Rapid Communications in Mass Spectrometry : RCM, vol. 21, no. 7, 2007, pp. 1165-75.
Es-Safi NE, Kerhoas L, Ducrot PH. Fragmentation study of iridoid glucosides through positive and negative electrospray ionization, collision-induced dissociation and tandem mass spectrometry. Rapid Commun Mass Spectrom. 2007;21(7):1165-75.
Es-Safi, N. E., Kerhoas, L., & Ducrot, P. H. (2007). Fragmentation study of iridoid glucosides through positive and negative electrospray ionization, collision-induced dissociation and tandem mass spectrometry. Rapid Communications in Mass Spectrometry : RCM, 21(7), 1165-75.
Es-Safi NE, Kerhoas L, Ducrot PH. Fragmentation Study of Iridoid Glucosides Through Positive and Negative Electrospray Ionization, Collision-induced Dissociation and Tandem Mass Spectrometry. Rapid Commun Mass Spectrom. 2007;21(7):1165-75. PubMed PMID: 17330213.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Fragmentation study of iridoid glucosides through positive and negative electrospray ionization, collision-induced dissociation and tandem mass spectrometry. AU - Es-Safi,Nour-Eddine, AU - Kerhoas,Lucien, AU - Ducrot,Paul-Henri, PY - 2007/3/3/pubmed PY - 2007/5/30/medline PY - 2007/3/3/entrez SP - 1165 EP - 75 JF - Rapid communications in mass spectrometry : RCM JO - Rapid Commun Mass Spectrom VL - 21 IS - 7 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 mass spectral study of a series of six naturally occurring iridoids through in-source fragmentation of the protonated [M+H]+, deprotonated [M--H]- and sodiated [M+Na]+ ions. This led to the unambiguous determination of the molecular masses of the studied compounds and allowed CID spectra of the molecular ions to be obtained. Valuable structural information regarding the nature of both the glycoside and the aglycone moiety was thus obtained. Glycosidic cleavage and ring cleavages of both aglycone and sugar moieties were the major fragmentation pathways observed during CID, where the losses of small molecules, the cinnamoyl and the cinnamate parts were also observed. The formation of the ionized aglycones, sugars and their product ions was thus obtained giving information on their basic skeleton. The protonated, i.e. [M+H]+ and deprotonated [M--H]-, ions were found to fragment mainly by glycosidic cleavages. MS/MS spectra of the [M+Na]+ ions gave complementary information for the structural characterization of the studied compounds. Unlike the dissociation of protonated molecular ions, that of sodiated molecules also provided sodiated sugar fragments where the C0+ fragment corresponding to the glucose ion was obtained as base peak for all the studied compounds. SN - 0951-4198 UR - https://www.unboundmedicine.com/medline/citation/17330213/Fragmentation_study_of_iridoid_glucosides_through_positive_and_negative_electrospray_ionization_collision_induced_dissociation_and_tandem_mass_spectrometry_ L2 - https://doi.org/10.1002/rcm.2930 DB - PRIME DP - Unbound Medicine ER -