Electrochemistry of flavonoids. Relationships between redox potentials, inhibition of mitochondrial respiration, and production of oxygen radicals by flavonoids.

Abstract:

:We have investigated the redox behavior of a series of structurally related flavonoids employing cyclic voltammetry under physiological conditions. The flavonoids that auto-oxidized and produced oxygen radicals had oxidation potentials (E 1/2) significantly lower [-30 to +60 mV vs (SCE)] than those that did not undergo auto-oxidation (+130 to +340 mV vs SCE). The range of E 1/2 values for the auto-oxidizable flavonoids was comparable to the E 1/2 range reported for the optimum quinone induced production of superoxide (O2 pi) in mitochondrial NADH-CoQ reductase (complex I). The most potent flavonoid inhibitors of mitochondrial succinate-CoQ reductase (complex II) possessed hydroxyl configurations capable of supporting redox reactions. For a series of 3,5,7-trihydroxyflavones that differed by b-ring hydroxylation it was found that decreasing E 1/2 of the flavonoids was associated with decreasing I50 values towards succinoxidase. These findings suggest that the electrochemical properties of the flavonoids may contribute to their biological activity.

journal_name

Biochem Pharmacol

journal_title

Biochemical pharmacology

authors

Hodnick WF,Milosavljević EB,Nelson JH,Pardini RS

doi

10.1016/0006-2952(88)90253-5

subject

Has Abstract

pub_date

1988-07-01 00:00:00

pages

2607-11

issue

13

eissn

0006-2952

issn

1873-2968

pii

0006-2952(88)90253-5

journal_volume

37

pub_type

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