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  • Title: Analysis of the oxidative degradation of proanthocyanidins under basic conditions.
    Author: Jorgensen EM, Marin AB, Kennedy JA.
    Journal: J Agric Food Chem; 2004 Apr 21; 52(8):2292-6. PubMed ID: 15080635.
    Abstract:
    Proanthocyanidin isolates from grape (Vitis vinifera L. cv. Pinot noir) skin and seed underwent oxidative degradation in solution (10 g/L) under basic conditions while exposed to atmospheric oxygen. Degradation was monitored by reversed-phase HPLC following acid-catalyzed cleavage in the presence of excess phloroglucinol (phloroglucinolysis) and by high-performance gel permeation chromatography. All isolates degraded under these conditions and followed second-order kinetics for over 1 half-life, consistent with an oxidation reaction. The conversion of proanthocyanidins to known subunits (conversion yield) when measured by phloroglucinolysis showed a dramatic decline over the course of the reaction. With the exception of (+)-catechin extension subunits, all individual subunits decreased in concentration during the oxidation process, also following second-order kinetics for over 1 half-life. Skin proanthocyanidins degraded the fastest due to the presence of (-)-epigallocatechin extension subunits. Seed procyanidins were degraded with and without flavan-3-ol monomers. Flavan-3-ol monomers slowed the rate of seed procyanidin degradation. The mean degree of polymerization (mDP) determined by phloroglucinolysis indicated a large decrease in mDP as the reaction progressed; yet, by GPC, the size distribution of all proanthocyanidins changed little in comparison. The conversion yield could be an important parameter to follow when using phloroglucinolysis as a means for determining proanthocyanidin mDP, and when monitoring the oxidative degradation of proanthocyanidins.
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