Betina V, Kuzela S
Chem Biol Interact. 1987;62(2):179-89. doi: 10.1016/0009-2797(87)90089-5.
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.
使用大鼠肝脏线粒体研究了七种蒽醌衍生物的结构-解偶联活性关系。三种在蒽醌核的β位带有游离羟基的化合物（1,3,6,8-四羟基蒽醌、1-乙酰基-2,4,5,7-四羟基-9,10-蒽二酮和skyrin）表现出解偶联效应。鲁格洛辛、鲁古林和大黄素甲醚（均在β位缺乏羟基）无活性。红菌素是大黄素甲醚在γ位带有游离羟基的衍生物，在所测试的系列中表现出最高的解偶联活性。此外，红菌素消除了线粒体中能量依赖的Ca2+保留并诱导Ca2+泄漏。它还阻止了ATP使线粒体膜通电，并像羰基氰-3-氯苯腙（CCCP）一样诱导ATP诱导的膜电位丧失。数据表明，蒽醌核γ位或β位的游离羟基是羟基蒽醌解偶联活性的先决条件。
