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Mass spectrometric evidence for the existence of oligomeric anthocyanins in grape skins.
J Agric Food Chem. 2004 Nov 17; 52(23):7144-51.JA

Abstract

The fractionation of a grape skin extract by multilayer countercurrent chromatography coupled with step gradient elution allowed the preparation of a fraction almost devoid of free anthocyanins. This fraction appeared to be almost exclusively polymeric, as judged by liquid chromatographic-mass spectrometric (LC-MS) analysis, color-bleaching tests with sulfur dioxide, and thiolysis. Electrospray mass spectrometric analysis indicated that the pigmented material in this fraction was chiefly composed of direct condensation products of anthocyanin extending up to trimers. With regard to their linkages, the anthocyanin units in the oligomers were possibly linked by either an A-type (by both carbon-carbon and ether bonds) or B-type (by carbon-carbon bond) linkage, like proanthocyanidins. The terminal anthocyanin unit of the oligomers is consistently in the flavylium form but the extension units are in the flavan form for the A-type oligomers and in the flavene form for the B-type oligomers. Although their linkages still need to be defined rigorously, this is the first mass spectrometric evidence confirming the existence of anthocyanin oligomers in the grape skin extract.

Authors+Show Affiliations

Vidal S
The Australian Wine Research Institute, Post Office Box 197, Glen Osmond SA 5064, Australia.
Meudec E
No affiliation info available
Cheynier V
No affiliation info available
Skouroumounis G
No affiliation info available
Hayasaka Y
No affiliation info available

MeSH

AnthocyaninsChromatography, LiquidFruitMass SpectrometryPolymersSpectrometry, Mass, Electrospray IonizationVitis

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

15537330

Citation

Vidal, Stéphane, et al. "Mass Spectrometric Evidence for the Existence of Oligomeric Anthocyanins in Grape Skins." Journal of Agricultural and Food Chemistry, vol. 52, no. 23, 2004, pp. 7144-51.
Vidal S, Meudec E, Cheynier V, et al. Mass spectrometric evidence for the existence of oligomeric anthocyanins in grape skins. J Agric Food Chem. 2004;52(23):7144-51.
Vidal, S., Meudec, E., Cheynier, V., Skouroumounis, G., & Hayasaka, Y. (2004). Mass spectrometric evidence for the existence of oligomeric anthocyanins in grape skins. Journal of Agricultural and Food Chemistry, 52(23), 7144-51.
Vidal S, et al. Mass Spectrometric Evidence for the Existence of Oligomeric Anthocyanins in Grape Skins. J Agric Food Chem. 2004 Nov 17;52(23):7144-51. PubMed PMID: 15537330.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Mass spectrometric evidence for the existence of oligomeric anthocyanins in grape skins. AU - Vidal,Stéphane, AU - Meudec,Emmanuelle, AU - Cheynier,Véronique, AU - Skouroumounis,George, AU - Hayasaka,Yoji, PY - 2004/11/13/pubmed PY - 2004/12/21/medline PY - 2004/11/13/entrez SP - 7144 EP - 51 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 52 IS - 23 N2 - The fractionation of a grape skin extract by multilayer countercurrent chromatography coupled with step gradient elution allowed the preparation of a fraction almost devoid of free anthocyanins. This fraction appeared to be almost exclusively polymeric, as judged by liquid chromatographic-mass spectrometric (LC-MS) analysis, color-bleaching tests with sulfur dioxide, and thiolysis. Electrospray mass spectrometric analysis indicated that the pigmented material in this fraction was chiefly composed of direct condensation products of anthocyanin extending up to trimers. With regard to their linkages, the anthocyanin units in the oligomers were possibly linked by either an A-type (by both carbon-carbon and ether bonds) or B-type (by carbon-carbon bond) linkage, like proanthocyanidins. The terminal anthocyanin unit of the oligomers is consistently in the flavylium form but the extension units are in the flavan form for the A-type oligomers and in the flavene form for the B-type oligomers. Although their linkages still need to be defined rigorously, this is the first mass spectrometric evidence confirming the existence of anthocyanin oligomers in the grape skin extract. SN - 0021-8561 UR - https://www.unboundmedicine.com/medline/citation/15537330/Mass_spectrometric_evidence_for_the_existence_of_oligomeric_anthocyanins_in_grape_skins_ DB - PRIME DP - Unbound Medicine ER -