Citation: ZHANG Fu-Gen, ZHOU Han-Yang, PENG Jing, WU Ji-Lan. Reactions between Flavonoids and α-Hydroxyl Ethyl Peroxyl Radicals: a Pulse Radiolysis Study[J]. Acta Physico-Chimica Sinica, ;2013, 29(01): 199-204. doi: 10.3866/PKU.WHXB201210232 shu

Reactions between Flavonoids and α-Hydroxyl Ethyl Peroxyl Radicals: a Pulse Radiolysis Study

1.
College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. China

Received Date: 13 August 2012
Available Online: 24 October 2012
Fund Project:

Lipid peroxidation (LPO) plays an important role in many pathological processes (such as hepatitis, hepatic sclerosis, atherosclerosis, cerebral hemorrhage and so on), and flavonoids are considered to be effective LPO-inhibitors. Thus we investigated the relationship between the chemical structure of flavonoids and the LPO activity and the antioxidant mechanism of flavonoids. In this work, α-hydroxyl ethyl peroxyl radicals were produced from radiolysis of aerated ethanol to model lipid peroxyl radicals. By detecting the decay of α-hydroxyl ethyl peroxyl radicals in the presence of different concentrations of flavonoids using pulse radiolysis, the reaction rate constants of α-hydroxyl ethyl peroxyl radicals with quercetin, rutin, catechin, and baicalin are determined for the first time. The antioxidant activity of these flavonoids decreases in the order: rutin > quercetin > baicalin > catechin. Flavone and pyrocatechol were used as model compounds for the different components in flavonoids and their reaction rate constants towards α-hydroxyl ethyl peroxyl radicals were (1.7±0.1)×10⁶ and (2.9±0.1)×10⁵ mol^-1·dm³· s^-1, respectively. The effect of chemical structure on the scavenging activity towards α-hydroxyl ethyl peroxyl radicals was investigated. The coexistence of the C₅-hydroxyl group in the A ring with the C₂＝C₃ in the C ring or the conjugated double bond of the B-C ring and the catechol group in the B ring provides the best antioxidant activity. In addition, the C₂＝C₃ in the C ring or the conjugated double bond of the B-C ring is more effective than the catechol group in the B ring, while the C₃-rutinose in the C ring has no obvious effect. Therefore, we conclude that the addition reaction between double bonds with peroxyl radicals plays an important role in the antioxidant activity of flavonoids in LPO.
- Flavonoids,
- Anti-lipid peroxidation,
- Pulse radiolysis,
- Dynamics,
- Chemical structure
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