Mechanism of inhibition of lipid peroxidation by gamma-terpinene, an unusual and potentially useful hydrocarbon antioxidant.
gamma-Terpinene (TH), a monoterpene hydrocarbon present in essential oils, retards the peroxidation of linoleic acid (LH). The peroxidation of TH has been shown to yield p-cymene as the only organic product in a chain reaction in which the chain carrier is the hydroperoxyl radical, HOO(.). The peroxidation of LH is well-known to be a chain reaction in which the chains are carried by linoleylperoxyl radicals, LOO., and the products are linoleyl hydroperoxides. The retardation of LH peroxidation by TH has been found to be due to rapid chain termination via a very fast cross-reaction between HOO. and LOO. radicals. This antioxidant mechanism is completely different from the mechanism of antioxidant action of vitamin E. Since vitamin E becomes a prooxidant at high concentrations, the addition of essential oils containing TH to edible lipids may provide an alternative or supplementary strategy for obtaining large increases in their oxidative stability and shelf life, something that cannot be achieved by simply adding more and more vitamin E.
Foti
Mario C
MC
Istituto di Chimica Biomolecolare del CNR-Sezione di Catania, Via del Santuario 110, I-95028 Valverde (CT), Italy. foti@issn.ct.cnr.it
Ingold
K U
KU
D000081005:Cyclohexane Monoterpenes; D005227:Fatty Acids / Q000494:pharmacology*; D005609:Free Radicals; D019787:Linoleic Acid / Q000378:metabolism; D015227:Lipid Peroxidation / Q000187:drug effects*; D008054:Lipid Peroxides / Q000378:metabolism*; D039821:Monoterpenes; D010084:Oxidation-Reduction; D013729:Terpenes / Q000494:pharmacology*
D000081005:Cyclohexane Monoterpenes; D005227:Fatty Acids; D005609:Free Radicals; D008054:Lipid Peroxides; D039821:Monoterpenes; D013729:Terpenes; C013584:lipid peroxidation inhibitor; C018669:gamma-terpinene; D019787:Linoleic Acid