Tags

Type your tag names separated by a space and hit enter

Characterization of procyanidin B2 oxidation products in an apple juice model solution and confirmation of their presence in apple juice by high-performance liquid chromatography coupled to electrospray ion trap mass spectrometry.
J Mass Spectrom. 2011 Nov; 46(11):1186-97.JM

Abstract

Procyanidins (i.e. condensed tannins) are polyphenols commonly found in fruits. During juice and cider making, apple polyphenol oxidase catalyzes the oxidation of caffeoylquinic acid (CQA) into its corresponding o-quinone which further reacts with procyanidins and other polyphenols, leading to the formation of numerous oxidation products. However, the structure and the reaction pathways of these neoformed phenolic compounds are still largely unknown. Experiments were carried out on a model system to gain insights into the chemical processes occurring during the initial steps of fruit processing. Procyanidin B2 was oxidized by caffeoylquinic acid o-quinone (CQAoq) in an apple juice model solution. The reaction products were monitored using high performance liquid chromatography (HPLC) coupled to ultraviolet (UV)-visible and electrospray tandem mass spectrometry (ESI-MS/MS) in the negative mode. Oxidative conversion of procyanidin B2 ([M-H](-) at m/z 577) into procyanidin A2 at m/z 575 was unambiguously confirmed. In addition, several classes of products were characterized by their deprotonated molecules ([M-H](-)) and their MS/MS fragmentation patterns: hetero-dimers (m/z 929) and homo-dimers (m/z 1153 and 705) resulting from dimerization involving procyanidin and CQA molecules; intramolecular addition products at m/z 575, 573, 927, 1151 and 703. Interestingly, no extensive polymerization was observed. Analysis of a cider apple juice enabled comparison with the results obtained on a biosynthetic model solution. However, procyanidin A2 did not accumulate but seemed to be an intermediate in the formation of an end-product at m/z 573 for which two structural hypotheses are given. These structural modifications of native polyphenols as a consequence of oxidation probably have an impact on the organoleptic and nutritional properties of apple juices and other apple-derived foods.

Authors+Show Affiliations

UR117, Recherches Cidricoles et Biotransformation des Fruits et Légumes, INRA, F-35653 Le Rheu, France.No affiliation info availableNo 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

22124992

Citation

Poupard, Pascal, et al. "Characterization of Procyanidin B2 Oxidation Products in an Apple Juice Model Solution and Confirmation of Their Presence in Apple Juice By High-performance Liquid Chromatography Coupled to Electrospray Ion Trap Mass Spectrometry." Journal of Mass Spectrometry : JMS, vol. 46, no. 11, 2011, pp. 1186-97.
Poupard P, Sanoner P, Baron A, et al. Characterization of procyanidin B2 oxidation products in an apple juice model solution and confirmation of their presence in apple juice by high-performance liquid chromatography coupled to electrospray ion trap mass spectrometry. J Mass Spectrom. 2011;46(11):1186-97.
Poupard, P., Sanoner, P., Baron, A., Renard, C. M., & Guyot, S. (2011). Characterization of procyanidin B2 oxidation products in an apple juice model solution and confirmation of their presence in apple juice by high-performance liquid chromatography coupled to electrospray ion trap mass spectrometry. Journal of Mass Spectrometry : JMS, 46(11), 1186-97. https://doi.org/10.1002/jms.2007
Poupard P, et al. Characterization of Procyanidin B2 Oxidation Products in an Apple Juice Model Solution and Confirmation of Their Presence in Apple Juice By High-performance Liquid Chromatography Coupled to Electrospray Ion Trap Mass Spectrometry. J Mass Spectrom. 2011;46(11):1186-97. PubMed PMID: 22124992.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Characterization of procyanidin B2 oxidation products in an apple juice model solution and confirmation of their presence in apple juice by high-performance liquid chromatography coupled to electrospray ion trap mass spectrometry. AU - Poupard,Pascal, AU - Sanoner,Philippe, AU - Baron,Alain, AU - Renard,Catherine M G C, AU - Guyot,Sylvain, PY - 2011/11/30/entrez PY - 2011/11/30/pubmed PY - 2012/1/26/medline SP - 1186 EP - 97 JF - Journal of mass spectrometry : JMS JO - J Mass Spectrom VL - 46 IS - 11 N2 - Procyanidins (i.e. condensed tannins) are polyphenols commonly found in fruits. During juice and cider making, apple polyphenol oxidase catalyzes the oxidation of caffeoylquinic acid (CQA) into its corresponding o-quinone which further reacts with procyanidins and other polyphenols, leading to the formation of numerous oxidation products. However, the structure and the reaction pathways of these neoformed phenolic compounds are still largely unknown. Experiments were carried out on a model system to gain insights into the chemical processes occurring during the initial steps of fruit processing. Procyanidin B2 was oxidized by caffeoylquinic acid o-quinone (CQAoq) in an apple juice model solution. The reaction products were monitored using high performance liquid chromatography (HPLC) coupled to ultraviolet (UV)-visible and electrospray tandem mass spectrometry (ESI-MS/MS) in the negative mode. Oxidative conversion of procyanidin B2 ([M-H](-) at m/z 577) into procyanidin A2 at m/z 575 was unambiguously confirmed. In addition, several classes of products were characterized by their deprotonated molecules ([M-H](-)) and their MS/MS fragmentation patterns: hetero-dimers (m/z 929) and homo-dimers (m/z 1153 and 705) resulting from dimerization involving procyanidin and CQA molecules; intramolecular addition products at m/z 575, 573, 927, 1151 and 703. Interestingly, no extensive polymerization was observed. Analysis of a cider apple juice enabled comparison with the results obtained on a biosynthetic model solution. However, procyanidin A2 did not accumulate but seemed to be an intermediate in the formation of an end-product at m/z 573 for which two structural hypotheses are given. These structural modifications of native polyphenols as a consequence of oxidation probably have an impact on the organoleptic and nutritional properties of apple juices and other apple-derived foods. SN - 1096-9888 UR - https://www.unboundmedicine.com/medline/citation/22124992/Characterization_of_procyanidin_B2_oxidation_products_in_an_apple_juice_model_solution_and_confirmation_of_their_presence_in_apple_juice_by_high_performance_liquid_chromatography_coupled_to_electrospray_ion_trap_mass_spectrometry_ L2 - https://doi.org/10.1002/jms.2007 DB - PRIME DP - Unbound Medicine ER -