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ABTS radical-driven oxidation of polyphenols: isolation and structural elucidation of covalent adducts.
Biochem Biophys Res Commun. 2006 Jul 21; 346(1):321-9.BB

Abstract

The formation of covalent adducts obtained from the reaction of the polyphenols, trans-3,3',4',5,7-pentahydroxyflavan (catechin) and 1,3,5-trihydroxybenzene (phloroglucinol), with ABTS radicals is reported. Two adducts derived from (+)-catechin and three adducts from phloroglucinol were isolated and identified using reversed-phase high performance liquid chromatography (HPLC) and electrospray ionization mass spectrometry (ESI-MS). The molecular masses of the (+)-catechin-derived adducts (I(c) and II(c)) were found to be 802 and 559 Da, respectively, whereas the masses of phloroglucinol-derived adducts (I(p), II(p), and III(p)) were 638, 395, and 381 Da, respectively. The initially formed adducts (I(c), I(p)) were unstable and degraded to secondary adducts (II(c), II(p), and III(p)) releasing part of the ABTS molecule. The structures of these adducts were elucidated by interpreting the results of MS/MS analysis of prominent ions generated by both positive and negative ion ESI-MS. The adducts were found to scavenge ABTS radicals, an observation that could explain the complex kinetic behaviour manifested by the reactions of ABTS radicals with polyphenols. A mechanism, which accounts for both the formation of the adducts and the degradation products of ABTS radicals, is proposed.

Authors+Show Affiliations

Scion, Private Bag 3020, Rotorua, New Zealand. Ahmed.Osman@Scionresearch.comNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

16756947

Citation

Osman, A M., et al. "ABTS Radical-driven Oxidation of Polyphenols: Isolation and Structural Elucidation of Covalent Adducts." Biochemical and Biophysical Research Communications, vol. 346, no. 1, 2006, pp. 321-9.
Osman AM, Wong KK, Fernyhough A. ABTS radical-driven oxidation of polyphenols: isolation and structural elucidation of covalent adducts. Biochem Biophys Res Commun. 2006;346(1):321-9.
Osman, A. M., Wong, K. K., & Fernyhough, A. (2006). ABTS radical-driven oxidation of polyphenols: isolation and structural elucidation of covalent adducts. Biochemical and Biophysical Research Communications, 346(1), 321-9.
Osman AM, Wong KK, Fernyhough A. ABTS Radical-driven Oxidation of Polyphenols: Isolation and Structural Elucidation of Covalent Adducts. Biochem Biophys Res Commun. 2006 Jul 21;346(1):321-9. PubMed PMID: 16756947.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - ABTS radical-driven oxidation of polyphenols: isolation and structural elucidation of covalent adducts. AU - Osman,A M, AU - Wong,K K Y, AU - Fernyhough,A, Y1 - 2006/05/30/ PY - 2006/04/28/received PY - 2006/05/18/accepted PY - 2006/6/8/pubmed PY - 2006/8/29/medline PY - 2006/6/8/entrez SP - 321 EP - 9 JF - Biochemical and biophysical research communications JO - Biochem Biophys Res Commun VL - 346 IS - 1 N2 - The formation of covalent adducts obtained from the reaction of the polyphenols, trans-3,3',4',5,7-pentahydroxyflavan (catechin) and 1,3,5-trihydroxybenzene (phloroglucinol), with ABTS radicals is reported. Two adducts derived from (+)-catechin and three adducts from phloroglucinol were isolated and identified using reversed-phase high performance liquid chromatography (HPLC) and electrospray ionization mass spectrometry (ESI-MS). The molecular masses of the (+)-catechin-derived adducts (I(c) and II(c)) were found to be 802 and 559 Da, respectively, whereas the masses of phloroglucinol-derived adducts (I(p), II(p), and III(p)) were 638, 395, and 381 Da, respectively. The initially formed adducts (I(c), I(p)) were unstable and degraded to secondary adducts (II(c), II(p), and III(p)) releasing part of the ABTS molecule. The structures of these adducts were elucidated by interpreting the results of MS/MS analysis of prominent ions generated by both positive and negative ion ESI-MS. The adducts were found to scavenge ABTS radicals, an observation that could explain the complex kinetic behaviour manifested by the reactions of ABTS radicals with polyphenols. A mechanism, which accounts for both the formation of the adducts and the degradation products of ABTS radicals, is proposed. SN - 0006-291X UR - https://www.unboundmedicine.com/medline/citation/16756947/ABTS_radical_driven_oxidation_of_polyphenols:_isolation_and_structural_elucidation_of_covalent_adducts_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0006-291X(06)01194-6 DB - PRIME DP - Unbound Medicine ER -