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Characterisation by liquid chromatography coupled to electrospray ionisation ion trap mass spectrometry of phloroglucinol and 4-methylcatechol oxidation products to study the reactivity of epicatechin in an apple juice model system.
J Chromatogr A. 2008 Feb 01; 1179(2):168-81.JC

Abstract

The reactivity of the (-)-epicatechin structure towards caffeoylquinic acid o-quinones was studied in an apple juice model solution. The approach consisted in considering separately the reactivities of the two phenolic moieties of an (-)-epicatechin molecule: phloroglucinol and 4-methylcatechol were chosen to represent A- and B-rings, respectively. The oxidation products were characterised by RP-HPLC coupled with electrospray ionisation Mass spectrometry (MS). The reactivities of the A- and B-rings were clearly different on the basis of the oxidation products formed. Both A- and B-rings could be involved in covalent bond formation, but electron transfers only occurred with the B-ring. Most of the (-)-epicatechin oxidation products were linked by A/B-ring linkage ("head-to-tail" intermolecular coupling). After this first dimerisation step, intramolecular reactions seemed to be favoured. Therefore, the complexity of oxidation products in apple juice does not only result from an extensive polymerisation of native phenolic compounds, but also from a multiplicity of small molecules in different oxidation states and isomeric forms.

Authors+Show Affiliations

UR117, Recherches Cidricoles et Biotransformation des Fruits et Légumes, INRA, F-35653 Le Rheu, France. pascal.poupard@rennes.inra.frNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

18093608

Citation

Poupard, Pascal, et al. "Characterisation By Liquid Chromatography Coupled to Electrospray Ionisation Ion Trap Mass Spectrometry of Phloroglucinol and 4-methylcatechol Oxidation Products to Study the Reactivity of Epicatechin in an Apple Juice Model System." Journal of Chromatography. A, vol. 1179, no. 2, 2008, pp. 168-81.
Poupard P, Guyot S, Bernillon S, et al. Characterisation by liquid chromatography coupled to electrospray ionisation ion trap mass spectrometry of phloroglucinol and 4-methylcatechol oxidation products to study the reactivity of epicatechin in an apple juice model system. J Chromatogr A. 2008;1179(2):168-81.
Poupard, P., Guyot, S., Bernillon, S., & Renard, C. M. (2008). Characterisation by liquid chromatography coupled to electrospray ionisation ion trap mass spectrometry of phloroglucinol and 4-methylcatechol oxidation products to study the reactivity of epicatechin in an apple juice model system. Journal of Chromatography. A, 1179(2), 168-81.
Poupard P, et al. Characterisation By Liquid Chromatography Coupled to Electrospray Ionisation Ion Trap Mass Spectrometry of Phloroglucinol and 4-methylcatechol Oxidation Products to Study the Reactivity of Epicatechin in an Apple Juice Model System. J Chromatogr A. 2008 Feb 1;1179(2):168-81. PubMed PMID: 18093608.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Characterisation by liquid chromatography coupled to electrospray ionisation ion trap mass spectrometry of phloroglucinol and 4-methylcatechol oxidation products to study the reactivity of epicatechin in an apple juice model system. AU - Poupard,Pascal, AU - Guyot,Sylvain, AU - Bernillon,Stephane, AU - Renard,Catherine M G C, Y1 - 2007/12/03/ PY - 2007/08/24/received PY - 2007/11/06/revised PY - 2007/11/23/accepted PY - 2007/12/21/pubmed PY - 2008/3/26/medline PY - 2007/12/21/entrez SP - 168 EP - 81 JF - Journal of chromatography. A JO - J Chromatogr A VL - 1179 IS - 2 N2 - The reactivity of the (-)-epicatechin structure towards caffeoylquinic acid o-quinones was studied in an apple juice model solution. The approach consisted in considering separately the reactivities of the two phenolic moieties of an (-)-epicatechin molecule: phloroglucinol and 4-methylcatechol were chosen to represent A- and B-rings, respectively. The oxidation products were characterised by RP-HPLC coupled with electrospray ionisation Mass spectrometry (MS). The reactivities of the A- and B-rings were clearly different on the basis of the oxidation products formed. Both A- and B-rings could be involved in covalent bond formation, but electron transfers only occurred with the B-ring. Most of the (-)-epicatechin oxidation products were linked by A/B-ring linkage ("head-to-tail" intermolecular coupling). After this first dimerisation step, intramolecular reactions seemed to be favoured. Therefore, the complexity of oxidation products in apple juice does not only result from an extensive polymerisation of native phenolic compounds, but also from a multiplicity of small molecules in different oxidation states and isomeric forms. SN - 0021-9673 UR - https://www.unboundmedicine.com/medline/citation/18093608/Characterisation_by_liquid_chromatography_coupled_to_electrospray_ionisation_ion_trap_mass_spectrometry_of_phloroglucinol_and_4_methylcatechol_oxidation_products_to_study_the_reactivity_of_epicatechin_in_an_apple_juice_model_system_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0021-9673(07)02076-6 DB - PRIME DP - Unbound Medicine ER -