Autoxidation of polyunsaturated esters in water: chemical structure and biological activity of the products.

When polyunsaturated esters or fatty acids are dispersed for long periods in water in the presence of air, water-soluble substances are formed in great variety. Because these short-chain products are constantly eluted by the aqueous phase and are consequently not available for further reaction in the oil phase, many intermediates of classical autoxidation can be isolated and identified. The identification of several of these compounds is described. Some of the peroxidic and nonperoxidic autoxidation products show biochemical activity-in particular, inhibition of glycolysis and of respiration during incubation with tumor cells in vitro. Minimal inhibitory concentrations of pure, isolated products have been determined for Ehrlich ascites tumor cells. Synthetic short-chain (C(4)-C(10)) hydroxylated alpha,-unsaturated aldehydes have been shown to have this action and also to cause morphological changes in these cells which quickly lead to their death. Normal cells are not affected. Possible therapeutic use of these compounds in the treatment of malignant neoplasms is discussed.