Antioxidant mechanisms of polyphenolic caffeic acid oligomers, constituents of Salvia officinalis.

Abstract:

:Caffeic acid, rosmarinic acid and oligomers of caffeic acid with multiple catechol groups are all constituents of Salvia officinalis. Their antioxidant potential was investigated with regard to their radical scavenging activity and the stability and structure of the intermediate radicals. Pulse-radiolytic studies revealed very high rate constants with hydroxyl radicals. Evidence from kinetic modeling calculations suggested an unusual complex behavior due to the presence of both O4- and O3-semiquinones and formation and decay of a hydroxyl radical adduct at the vinyl side chain. The radical structures observed by EPR spectroscopy after autoxidation in slightly alkaline solutions were only partially identified due to their instability and generally represented dissociated O4-semiquinones. Hybrid density-functional calculations of the potential radical structures showed distinct differences between the resonance stabilization of the O4- and O3-semiquinones of caffeic and dihydrocaffeic acids, reflected also in the considerably faster decay of the O3-semiquinone observed by pulse radiolysis. No evidence was found for dimerization reactions via Cbeta radicals typical for lignin biosynthesis.

journal_name

Biol Res

journal_title

Biological research

authors

Bors W,Michel C,Stettmaier K,Lu Y,Foo LY

doi

10.4067/s0716-97602004000200017

keywords:

subject

Has Abstract

pub_date

2004-01-01 00:00:00

pages

301-11

issue

2

eissn

0716-9760

issn

0717-6287

journal_volume

37

pub_type

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