Uncoupling effect of fungal hydroxyanthraquinones on mitochondrial oxidative phosphorylation.

Abstract:

:Structure-uncoupling activity relationship of seven anthraquinone derivatives were investigated using rat liver mitochondria. Three compounds bearing the free hydroxyl group at the beta-position of their anthraquinone nucleus (1,3,6,8-tetrahydroxyanthraquinone, 1-acetyl-2,4,5,7-tetrahydroxy-9,10-anthracenedione and skyrin) exhibited uncoupling effect. Rugulosin, rugulin and physcion (all lacking the hydroxyl at the beta-position) were ineffective. Erythroglaucin, a derivative of physcion with the free hydroxyl group at the gamma-position, exhibited the highest uncoupling activity in the series tested. In addition, erythroglaucin abolished the energy dependent Ca2+ retention in mitochondria and induced Ca2+ leak. It also prevented the energization of mitochondrial membrane by ATP and induced a loss of the ATP induced membrane potential similarly as did carbonylcyanamide-3-chlorophenyl hydrazone (CCCP). The data show that the free hydroxyl group at either the gamma-position or the beta-position of anthraquinone nucleus is a prerequisite of the uncoupling activity of hydroxyanthraquinones.

journal_name

Chem Biol Interact

authors

Betina V,Kuzela S

doi

10.1016/0009-2797(87)90089-5

subject

Has Abstract

pub_date

1987-01-01 00:00:00

pages

179-89

issue

2

eissn

0009-2797

issn

1872-7786

pii

0009-2797(87)90089-5

journal_volume

62

pub_type

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