5-Lipoxygenase-derived oxylipins from the red alga Rhodymenia pertusa.

The lipid extract of the temperate red alga Rhodymenia pertusa has yielded four eicosanoid metabolites, three of which are new natural products. Using principally NMR and MS techniques, their structures were deduced as 5R,6S-dihydroxy-7(E),9(E),11(Z),14(Z)-eicosatetraenoic acid (5R,6S-diHETE), 5R*,6S*-dihydroxy-7(E),9(E),11(Z),14(Z),17(Z)-eicosapentaenoic acid (5R*,6S*-diHEPE), 5-hydroxy-6(E),8(Z),11(Z),14(Z)-eicosatetraenoic acid (5-HETE), 5-hydroxy-6(E),8(Z),11(Z),14(Z),17(Z)-eicosapentaenoic acid (5-HEPE). The co-occurrence of these metabolites strongly suggests that R. pertusa contains a unique 5R-lipoxygenase system acting on both arachidonic and eicosapentaenoic acids.

alpha-Tocopherol influences in vivo indices of lipid peroxidation in postmenopausal women given fish oil.

Although diets containing fish have been shown to be therapeutically valuable, the vitamin E requirement when large quantities of (n-3) fatty acids are consumed is not known. Additionally, as estrogens may function as an antioxidant, the requirement may be modified in postmenopausal women using hormone replacement therapy (HRT). Consequently, the purpose of this study was to measure the impact of graduated doses of RRR-alpha-tocopheryl acetate (TA) on in vivo indices of lipid peroxidation in postmenopausal women with and without hormone replacement therapy when given a supplement of fish oil. Forty-eight postmenopausal women, half receiving (+HRT) and half not receiving (-HRT) hormone replacement therapy, participated in a four-period, double-blind crossover trial. Each period lasted 5 wk followed by a 4-wk washout interval. During each period, the subjects consumed a 15-g supplement of fish oil and either 0, 100, 200, or 400 mg TA/d in a balanced, single square dosing order. Plasma levels of (n-3) fatty acids were significantly higher after fish oil supplementation; alpha-tocopherol concentration of plasma was significantly higher at each level of supplementation compared with the level without supplementation. Urinary excretion of thiobarbituric acid reactive substances (TBARS) and malondialdehyde, measured as the thiobarbituric-malondialdehyde adduct (TRA-MDA adduct), and the plasma concentration of the adduct were significantly greater after the fish oil supplement. Although urinary TBARS decreased linearly as the dose of TA increases (P < or = 0.05), urinary and plasma concentrations of TBA-MDA adduct did not. This study suggests that the evaluation of highly unsaturated fatty acids as oxidative stressors requires several measures of assessment.

Effects of interaction of RRR-alpha-tocopheryl acetate and fish oil on low-density-lipoprotein oxidation in postmenopausal women with and without hormone-replacement therapy.

We evaluated the effects of RRR-alpha-tocpheryl acetate (alpha-tocopheryl acetate) and hormone-replacement therapy (HRT) on the oxidative susceptibility of low-density lipoprotein (LDL) in postmenopausal women consuming a fish oil supplement. The independent effect of fish oil was also assessed. Forty-eight women, equally divided between women using and not using HRT, participated in a double-blind crossover trial. Each of the four periods lasted 5 wk and was followed by a 4-wk washout interval. During each period all subjects were given a 15-g supplement of fish oil and either 0 (placebo), 100, 200, or 400 mg alpha-tocopheryl acetate daily. LDL resistance to oxidative modification was assessed by calculating lag time, propagation rate, and maximum production of conjugated dienes. Supplementation with fish oil and placebo shortened lag time and slowed propagation rate in women both using and not using HRT. After subjects consumed fish oil, supplementation with alpha-tocopheryl acetate increased plasma and LDL alpha-tocopherol contents significantly and lengthened lag time (at even the lowest concentration) but had no significant effect on propagation rate or maximum production compared with values measured after consumption of fish oil alone. Women not using HRT had faster propagation rates and higher maximum production than women using HRT; after supplementation with fish oil and alpha-tocopheryl acetate these differences prevailed. Supplements as low as 100 mg alpha-tocopheryl acetate/d increase the resistance of LDL to oxidation when fish oil supplements are used. HRT and fish oil supplements may independently affect LDL oxidative susceptibility.