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In vitro flavon-3-ol oxidation mediated by a B ring hydroxylation pattern.

Abstract：

:Flavonols are potent naturally occurring antioxidants. Chemical oxidation reactions in combination with modern spectroscopic techniques have been employed to identify oxidized flavonoid products. Although many oxidized derivatives have been generated from commercially available starting materials, few studies have developed a sequence of flavonoid substrates with a particular hydroxylation pattern to probe the mechanism of flavonoid oxidation. Here, we use AIBN (2,2'-azobisisobutyronitrile) in combination with a series of hydroxylated flavonols to probe the mechanism of flavonoid dimer formation and the role of singly or doubly oxidized species in generating and promoting oxidized flavonoid products. 3-Methoxyquercetin (3-hydroxyl group blocked) and luteolin (lack of 3-hydroxyl) were reacted with AIBN alone or with a second flavonol to serve as a C-3 hydroxyl donor to examine the mechanism of dimer formation. 3-Hydroxyflavones with increasing hydroxyl substitutions in the B ring were also reacted with AIBN in the presence or absence of an external nucleophile to examine the role of various hydroxyls in the formation of a carbocation intermediate via a doubly oxidized species. The presence of a free C-3 hydroxyl, coupled with a B ring ortho hydroxy unit, appears essential for dimer formation. An increase in the number of hydroxyls in the B ring facilitates products generated from a doubly oxidized species.

journal_name

Chem Res Toxicol

journal_title

Chemical research in toxicology

authors

Krishnamachari V,Levine LH,Zhou C,Paré PW

doi

10.1021/tx034242z

subject

Has Abstract

pub_date

2004-06-01 00:00:00

pages

795-804

issue

6

eissn

0893-228X

issn

1520-5010

journal_volume

17

pub_type

杂志文章

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