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Tandem mass spectrometry of the B-type procyanidins in wine and B-type dehydrodicatechins in an autoxidation mixture of (+)-catechin and (-)-epicatechin.
J Mass Spectrom. 2003 Apr; 38(4):438-46.JM

Abstract

We describe the characterization of the B-type procyanidins in wine and the B-type dehydrodicatechins (dimeric flavan-3-ols) obtained for the autoxidation of (+)-catechin and (-)-epicatechin by tandem mass spectrometry (MS/MS) coupled to reversed-phase high-performance liquid chromatography (HPLC). The MS/MS analysis demonstrates that the interesting major fragments derive from the dissociations of the C-ring on the catechin or epicatechin unit, such as retro-Diels-Alder reactions. The two kinds of dimers give completely different fragmentations because of the striking effect of the C-C interflavan linkage (IFL). For the natural dimers in wine, a catechin or epicatechin unit linking to the C-4 position stabilizes the product ions by forming a large pi-pi hyperconjugated system, whereas a similar pi-pi system is formed within dehydrodicatechin B through the C-C IFL. Thus dissociation in MS/MS experiments was inhibited. Apparently, the fragmentations of the dimers differ from that of the monomer, which is very important in the study of the gas-phase ion behaviour of the polymeric flavan-3-ols. In addition, two specific fragment ions at m/z 451 for native dimers and at m/z 393 for autoxidation species in HPLC/MS/MS were found to be very useful for analysing mixtures of B-type procyanidins and B-type dehydrodicatechins in food and beverages.

Authors+Show Affiliations

Chemistry Department, Brock University, St. Catharines, Ontario, Canada, L2S 3A1.No affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

12717756

Citation

Sun, Weixing, and Jack M. Miller. "Tandem Mass Spectrometry of the B-type Procyanidins in Wine and B-type Dehydrodicatechins in an Autoxidation Mixture of (+)-catechin and (-)-epicatechin." Journal of Mass Spectrometry : JMS, vol. 38, no. 4, 2003, pp. 438-46.
Sun W, Miller JM. Tandem mass spectrometry of the B-type procyanidins in wine and B-type dehydrodicatechins in an autoxidation mixture of (+)-catechin and (-)-epicatechin. J Mass Spectrom. 2003;38(4):438-46.
Sun, W., & Miller, J. M. (2003). Tandem mass spectrometry of the B-type procyanidins in wine and B-type dehydrodicatechins in an autoxidation mixture of (+)-catechin and (-)-epicatechin. Journal of Mass Spectrometry : JMS, 38(4), 438-46.
Sun W, Miller JM. Tandem Mass Spectrometry of the B-type Procyanidins in Wine and B-type Dehydrodicatechins in an Autoxidation Mixture of (+)-catechin and (-)-epicatechin. J Mass Spectrom. 2003;38(4):438-46. PubMed PMID: 12717756.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Tandem mass spectrometry of the B-type procyanidins in wine and B-type dehydrodicatechins in an autoxidation mixture of (+)-catechin and (-)-epicatechin. AU - Sun,Weixing, AU - Miller,Jack M, PY - 2003/4/30/pubmed PY - 2003/7/25/medline PY - 2003/4/30/entrez SP - 438 EP - 46 JF - Journal of mass spectrometry : JMS JO - J Mass Spectrom VL - 38 IS - 4 N2 - We describe the characterization of the B-type procyanidins in wine and the B-type dehydrodicatechins (dimeric flavan-3-ols) obtained for the autoxidation of (+)-catechin and (-)-epicatechin by tandem mass spectrometry (MS/MS) coupled to reversed-phase high-performance liquid chromatography (HPLC). The MS/MS analysis demonstrates that the interesting major fragments derive from the dissociations of the C-ring on the catechin or epicatechin unit, such as retro-Diels-Alder reactions. The two kinds of dimers give completely different fragmentations because of the striking effect of the C-C interflavan linkage (IFL). For the natural dimers in wine, a catechin or epicatechin unit linking to the C-4 position stabilizes the product ions by forming a large pi-pi hyperconjugated system, whereas a similar pi-pi system is formed within dehydrodicatechin B through the C-C IFL. Thus dissociation in MS/MS experiments was inhibited. Apparently, the fragmentations of the dimers differ from that of the monomer, which is very important in the study of the gas-phase ion behaviour of the polymeric flavan-3-ols. In addition, two specific fragment ions at m/z 451 for native dimers and at m/z 393 for autoxidation species in HPLC/MS/MS were found to be very useful for analysing mixtures of B-type procyanidins and B-type dehydrodicatechins in food and beverages. SN - 1076-5174 UR - https://www.unboundmedicine.com/medline/citation/12717756/Tandem_mass_spectrometry_of_the_B_type_procyanidins_in_wine_and_B_type_dehydrodicatechins_in_an_autoxidation_mixture_of__+__catechin_and_____epicatechin_ L2 - https://doi.org/10.1002/jms.456 DB - PRIME DP - Unbound Medicine ER -