Oxidation of Procyanidins with Various Degrees of Condensation: Influence on the Color-Deepening Phenomenon.

Color deepening in red rice is a known phenomenon that occurs during postharvest storage. As procyanidins potentially causes this color deepening, we previously subjected synthetic procyanidin B3, a model procyanidin, to chemical oxidation and determined the structures of the products. To further elucidate the effects of various degrees of polymerization on color deepening, in this study we oxidized synthetic procyanidin C2. The intensity of the UV-vis absorption between 300 and 500 nm in the spectrum of the reaction mixture increased with increasing oxidation time. This absorption following the oxidation of procyanidin C2 was more intense than that of procyanidin B3. HPLC-ESI-MS of the oxidized reaction mixture revealed several new peaks that suggested the formation of products with new intramolecular rather than intermolecular bonds. The major product was structurally identified by comparison with the UPLC-ESI-MS/MS data for a synthetic procyanidin C2 oxide, independently prepared by condensing procyanidin B3 oxide and taxifolin.