Platanetin: A Potent Natural Uncoupler and Inhibitor of the Exogenous NADH Dehydrogenase in Intact Plant Mitochondria.

Platanetin is a 3,5,7,8-tetrahydroxy, 6-isoprenyl flavone isolated from the bud scales of the plane tree (Platanus acerifolia Willd.). Its effects on the oxidative activities of isolated potato and mung bean mitochondria have been studied. The most noticeable effect is the selective inhibitory effect of this compound on the activity of the external NADH dehydrogenase of the inner membrane. A 50% inhibition of the NADH oxidation rate is obtained at a 2 micromolar concentration. This activity is probably due to the flavonoid structure and the high lipophilicity of platanetin associated with the presence of the isoprenyl chain. Another important effect of platanetin is its uncoupling activity on oxidative phosphorylation. The presence of easily dissociable hydroxyl groups and the high lipophilicity of platanetin allow a potent H(+) transfer through the mitochondrial inner membrane. This uncoupling activity is comparable to that of carbonyl cyanide p-trifluoromethoxyphenylhydrazone. Platanetin is therefore the most active natural uncoupler known at the present time (full uncoupling at 2 micromolar with succinate as substrate). At higher concentrations (10 micromolar and more), platanetin can transfer electrons from the mitochondrial inner membrane to O(2); the branching point of this KCN-salicylhydroxamic acid insensitive platanetin dependent oxidative pathway is located at the level of flavoproteins, no transfer occurring when succinate is the substrate. The redox properties of platanetin are in accord with such an activity.