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Energetic and Electronic Computation of the Two-Hydrogen Atom Donation Process in Catecholic and Non-Catecholic Anthocyanidins

Energetic and Electronic Computation of the Two-Hydrogen Atom Donation Process in Catecholic and Non-Catecholic Anthocyanidins

Hussein M Ali, Isra H Ali

Food Chem. 2018 Mar 15;243:145-150.

PMID: 29146321

Abstract:

Antioxidant activity of anthocyanidins is greatly affected by the 3-hydroxyl group and/or a catecholic moiety. The two-hydrogen atom donation process is frequently used to explain the high antioxidant activity of polyphenolic compounds leading to the formation of stable diketones e.g. 1,2-quinones. Thermodynamic parameters, HOMO and spin density were computed to identify the favoured path, either through the 3-hydroxyl group or through the catecholic moiety in a series of catecholic and non-catecholic 3-oxy- (and deoxy)-anthocyanidins. DFT calculations showed that the donation process in non-catecholic anthocyanidins depended on the substituents on ring B. Anthocyanidins with 3',5'-diOMe groups showed donation through 3,4'-OH or, otherwise, through 3,5-OH groups. Catecholic 3-oxyanthocyanidins, on the other hand, showed donation through the 3,4'-OH path rather than the catecholic path (4',3'-path). The 3,4'-path was favoured by the formation of planar 3-radicals in the first step and the stabilization of 4'-radicals in the second step by H-bonding with the 3'-OH group.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP134010	Peonidin chloride		134-01-0	Price
AP643845	Malvidin chloride		643-84-5	Price

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