Function of plastochromanol and other biological prenyllipids in the inhibition of lipid peroxidation-A comparative study in model systems.

Lipid peroxidation is an oxidation reaction leading to the generation of lipid hydroperoxides. Here we present comparative data on the inhibition of lipid peroxidation by a variety of biological prenyllipids in liposomes prepared from natural lipid membranes. Lipid peroxidation was initiated by hydrophilic and hydrophobic azo initiators, as well as by singlet oxygen generated via photosensitized reaction of hydrophobic zinc tetraphenylporphine. When lipid peroxidation was initiated in the water phase, tocopherols and plastochromanol-8 were more effective than prenylquinols, such as plastoquinol-9, ubiquinol-10 or α-tocopherolquinol. However, if the peroxidation was initiated within the hydrophobic interior of liposome membranes, long-chain prenyllipids, such as plastoquinol-9 and plastochromanol-8, were considerably more active than tocopherols in the inhibition of the reaction. In the latter system, tocopherols showed even prooxidant activity. The prooxidant activity of α-tocopherol was prevented by plastoquinol, suggesting the reduction of α-tocopheroxyl radical by the quinol. All the investigated prenyllipids were able to inhibit singlet oxygen-mediated lipid peroxidation but the most active were prenylquinols in this respect. Among all the prenyllipids investigated, plastochromanol-8 was the most versatile antioxidant in the inhibition of lipid peroxidation initiated by the three different methods.