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Identification of autoxidation oligomers of flavan-3-ols in model solutions by HPLC-MS/MS.
J Mass Spectrom. 2009 May; 44(5):633-40.JM

Abstract

Autoxidation of flavan-3-ols was carried out in aqueous/methanol model solutions under mildly acidic conditions (pH 6.0), and these autoxidation products were analyzed by using high performance liquid chromatography (HPLC) coupled with tandem mass spectrometry (MS/MS). The results showed that (+)-catechins and (-)-epicatechins generated autoxidation reaction with each other to form a series of oligomers that had the same [M - H](-) molecular ions (MS(1)) as those of natural procyanidins, but had completely different fragment ions (MS(2)). According to MS/MS analysis, the major fragments of these oligomers were derived not only from the retro-Diels-Alder (RDA) dissociations on the C-rings of the flavan-3-ol units, but also from the quinone-methide (QM) cleavage of the interflavan linkages (IFL), and thus they were identified as B-type dehydrodicatechins, B-type dehydrotricatechins and A-type dehydrotricatechins, respectively. The potential structures of their [M - H](-) molecular ions and partial fragment ions were deduced on the basis of the MS/MS characterization and the oxidation of flavan-3-ols in previous reports. Some specific fragment ions were found to be very useful for identifying the autoxidation oligomers (the B-type dehydrodicatechins at m/z 393, the B-type dehydrotricatechins at m/z 681 and the A-type dehydrotricatechins at m/z 725).

Authors+Show Affiliations

Centre for Viticulture and Enology, College of Food Science and Nutritional Engineering, China Agricultural University, Beijing 100083, China.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

19053150

Citation

He, Fei, et al. "Identification of Autoxidation Oligomers of Flavan-3-ols in Model Solutions By HPLC-MS/MS." Journal of Mass Spectrometry : JMS, vol. 44, no. 5, 2009, pp. 633-40.
He F, Pan QH, Shi Y, et al. Identification of autoxidation oligomers of flavan-3-ols in model solutions by HPLC-MS/MS. J Mass Spectrom. 2009;44(5):633-40.
He, F., Pan, Q. H., Shi, Y., Zhang, X. T., & Duan, C. Q. (2009). Identification of autoxidation oligomers of flavan-3-ols in model solutions by HPLC-MS/MS. Journal of Mass Spectrometry : JMS, 44(5), 633-40. https://doi.org/10.1002/jms.1536
He F, et al. Identification of Autoxidation Oligomers of Flavan-3-ols in Model Solutions By HPLC-MS/MS. J Mass Spectrom. 2009;44(5):633-40. PubMed PMID: 19053150.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Identification of autoxidation oligomers of flavan-3-ols in model solutions by HPLC-MS/MS. AU - He,Fei, AU - Pan,Qiu-Hong, AU - Shi,Ying, AU - Zhang,Xue-Ting, AU - Duan,Chang-Qing, PY - 2008/12/5/pubmed PY - 2009/7/29/medline PY - 2008/12/5/entrez SP - 633 EP - 40 JF - Journal of mass spectrometry : JMS JO - J Mass Spectrom VL - 44 IS - 5 N2 - Autoxidation of flavan-3-ols was carried out in aqueous/methanol model solutions under mildly acidic conditions (pH 6.0), and these autoxidation products were analyzed by using high performance liquid chromatography (HPLC) coupled with tandem mass spectrometry (MS/MS). The results showed that (+)-catechins and (-)-epicatechins generated autoxidation reaction with each other to form a series of oligomers that had the same [M - H](-) molecular ions (MS(1)) as those of natural procyanidins, but had completely different fragment ions (MS(2)). According to MS/MS analysis, the major fragments of these oligomers were derived not only from the retro-Diels-Alder (RDA) dissociations on the C-rings of the flavan-3-ol units, but also from the quinone-methide (QM) cleavage of the interflavan linkages (IFL), and thus they were identified as B-type dehydrodicatechins, B-type dehydrotricatechins and A-type dehydrotricatechins, respectively. The potential structures of their [M - H](-) molecular ions and partial fragment ions were deduced on the basis of the MS/MS characterization and the oxidation of flavan-3-ols in previous reports. Some specific fragment ions were found to be very useful for identifying the autoxidation oligomers (the B-type dehydrodicatechins at m/z 393, the B-type dehydrotricatechins at m/z 681 and the A-type dehydrotricatechins at m/z 725). SN - 1096-9888 UR - https://www.unboundmedicine.com/medline/citation/19053150/Identification_of_autoxidation_oligomers_of_flavan_3_ols_in_model_solutions_by_HPLC_MS/MS_ L2 - https://doi.org/10.1002/jms.1536 DB - PRIME DP - Unbound Medicine ER -