A Novel Uncoupler of Mitochondrial Respiration, 9, 10-Epoxy-12-octadecenoate, Exists in Human Burned Skin

In human burned skin, several polyunsaturated fatty acids, especially linoleate and its peroxide were isolated by high-performance liquid chromatography. Chemical structure of the epoxide was determined to be 9, 10-epoxy-12-octadecenoate by gas-chromatography/mass spectrometry, nuclear magnetic resonance measurements and ozonolysis. The epoxide showed an uncoupling activity to liver mitochondrial respiration and diminished the respiratory control of mitochondria. Formation of the epoxide in the burned skin was related to clinical observation of the “burn toxin” which appears after severe burns.