Abstract
The antioxidant properties of sesame lignans (sesamol, sesamin and sesamolin) were evaluated in comparison to tocols (α- and γ-tocopherols and α-tocotrienol) and butylated hydroxytoluene (BHT) using the following in vitro lipid peroxidation systems: (i) rat liver microsomes and cumene hydroperoxide (CumOOH)/Fe2+-ADP-NADPH (enzymatic) or (ii) rat liver mitochondria and Fe2+-ascorbate (nonenzymatic) systems. Sesamol containing a free phenolic group inhibited lipid peroxidation in both the systems whereas sesamin and sesamolin having methylenedioxy groups were effective only in the microsomal system. Since detoxifying enzymes are localized in microsomes, the inhibitory effects of sesamin and sesamolin observed in the microsomal system may be attributed to their metabolites. However, the inhibitory effects of lignans were lower than tocols and BHT. Combination of individual lignans and tocopherols (α, γ) or α-tocotrienol showed higher inhibitory effects than the sum of individual inhibitions in CumOOH and Fe2+-ascorbate systems suggesting synergistic interactions. The time course of CumOOH-mediated lipid peroxidation showed a lag period and a decreased rate of thiobarbituric acid reactive product formation in the presence of individual lignans in combination with α-tocopherol suggesting recycling of α-tocopherol. (Mol Cell Biochem 262: 195–202, 2004)
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Shahidi F, Shukla VKS: Non-triacylglycerol constituents of fats, oils.Inform 7: 1227–1232, 1996
Sugano M, Akimoto K: Sesamin a multifuntional gift from nature. J Chinese Nutr Sci 18: 1–11, 1993
Namiki M: The chemistry and physiological functions of sesame. Food Rev Int 11: 281–329, 1995
Fukuda Y, Nagata M, Osawa T, Namiki M: Chemical aspects of the antioxidant activity of roasted sesame seed oil and the effect of using the oil for frying. Agric Biol Chem 50: 857–862, 1986.
Fukuda Y, Nagata M, Osawa T, Namiki M: Contribution of lignan analogues to antioxidant activity of refined unroasted sesame seed oil. J Am Oil Chem Soc 10: 1027–1031, 1986
Pauline S: Current research in natural food antioxidants. Inform 5: 679–687, 1994
Budowski P: Antioxidant properties of sesamol. J Am Oil Chem Soc 27: 264–267, 1950
Budowski P, Connor RTO, Feild ET: Sesame oil. VI. Determination of sesamin. J Am Oil Chem Soc 2: 51–54, 1951
Johnson D, Lardy H: Isolation of liver or kidney mitochondria. Methods Enzymol 10: 94–96, 1967
Ernster L, Nordenbrand K: Microsomal lipid peroxidation. Methods Enzymol 10: 574–580, 1967
Lowry OH, Rosebrough NJ, Palade GE: Protein measurement with folin phenol reagent. J Biol Chem 193: 265–275, 1951
Weiss RH, Estabrook RW: The Mechanism of cumene hydroperoxide dependent lipid peroxidation. The function of cytochrome P450. Arch Biochem Biophys 251: 348–360, 1986
Sringen BA, Buege JA, Neil FO, Aust DS: The mechanism of NADPH dependent lipid peroxidation. J Biol Chem 254: 5892–5899, 1979
Forthey SR, Lynn Jr WS: Role of ascorbate and cysteine on swelling and lipid peroxidation in rat liver mitochondria. Arch Biochem Biophys 104: 241–247, 1964
Slater TF, Sawyer BC: The stimulatory effects of carbon tetrachloride and other halogeno-alkanes on peroxidative reactions in rat liver fractions in vitro. Biochem J 123: 805–814, 1971
Zhu QY, Huang YY, Chen ZY: Interaction between flavanoids and α-tocopherol in human lowdensity lipoprotein. J Nutr Biochem 11: 14–21, 2000
Anthony TB: The role of antioxidant nutrients in disease. Inform 3: 1214–1217, 1992
Hauman BF: Antioxidants: Health implications. Inform 5: 242–253, 1994
Estabrook RW, Weiss RH: The mechanism of cumene hydroperoxide dependent lipid peroxidation. The significance of oxygen uptake. Arch Biochem Biophys 251: 336–347, 1986
Serbinova E, Kagan V, Han D, Packer L: Free radical recycling and intermembrane mobility in the antioxidant properties of α-tocopherol and α-tocotrienol. Free Rad Biol Med 10: 263–275, 1991
Suzuki YJ, Tsuchiya M, Wassall SR, Choo YM, Govil G, Kagan VE, Packer L: Structural and dynamic membrane properties of α-tocopherol and α-tocotrienol, implications to the molecular mechanisms of their antioxidant potency. Biochemistry 32: 10692–10699, 1993
Rajkumar DV, Rao MNA: Dehydrogingerone and isoeugenol as inhibitors of lipid peroxidation and as free radical scavengers. Biochem Pharmacol 46: 2067–2072, 1993
Uchida M, Nakajin S, Toyoshima S, Shinoda M: Antioxidative effect of sesamol and related compounds on lipid peroxidation. Biol Pharm Bull 19: 623–626, 1996
Asami S, Akimoto K, Abe K, Akamatsu T, Konishi K, Shimizu S, Sugano M, Yamada H: Antioxidant activity of sesamin on NADPH dependent lipid peroxidation in liver microsomes. Nippon Noge Kagaku Kaishi 67: 265, 1993
Chen CC, Chen HY, Shiao MS, Lin YL, Kuo YH, Ou JC: Inhibition of low density lipoprotein oxidation by tetrahydrofurofuran lignans from forsythia suspensa and Magnolia Coco. Planta Med 65: 709–711, 1999
Kang M, Oaito M, Tsujihara N, Osawa T: Sesamolin inhibits lipid peroxidation in rat liver and kidney. J Nutr 128: 1018–1022, 1998
Parker RS, Sontag TJ, Swanson JE: Cytochrome P450 3A-dependent metabolism of tocopherols and inhibition by sesamin. Biochem Biophys Res Commun 277: 531–534, 2000
Kumagai Y, Lin YL, Philpot RM, Yamada H, Oguri K, Yoshimura H, Cho AK: Regiochemical differences in cytochrome P450 isoenzymes responsible for the oxidation of methylenedioxyphenyl groups by rabbit liver. Mol Pharmcol 42: 695–702, 1992
Yamashita K, Kawagoe Y, Nohara Y, Namiki M, Osawa T, Kawagishi S: Effect of sesame in the senescence accelerated mouse. J Jpn Soc Nutr Food Sci 43: 445–449, 1990
Chou TC, Marlett AL: Factors in the Chinese diet affecting carotene utilization. J Nutr 51: 305–315, 1953
Kagan VE, Serbinova EA, Packer L: Generation and recycling of radicals from phenolic antioxidants. Arch Biochem Biophys 280: 33–39, 1990
Kagan VE, Serbinova EA, Packer L: Recycling and antioxidant activity of tocopherol homologs of differing hydrocarbon chain lengths in liver microsomes. Arch Biochem Biophys 282: 221–225, 1990
Sontag TJ, Parker RS: Cytochrome P450 ?-hydroxylase pathway of tocopherol catabolism. J Biol Chem 277: 25290–25296, 2002
Leung HW, Vang MJ, Maris RD: The cooperative interaction between vitamin E and vitamin C in suppression of peroxidation of membrane phospholipids. Biochem Biophys Acta 264: 266–272, 1982
Scholz KS, Liken AD, Gumpricht E, Reddy CD: Glutahione-dependent factors and inhibition of rat liver microsomal lipid peroxidation. Free Rad Biol Med 23: 815–828, 1997
Kamal Eldin A, Patterson D, Appelqvist L: Sesamin (a compound from sesame oil) increases tocopherol levels in rats fed ad libitum. Lipids 30: 499–505, 1995
Nakabayashi A, Kitagawa Y, Suwa Y, Akimoto K, Asami S, Shimizu S, Hirose N, Sugano M, Yamada H: α-Tocopherol enhances the hypocholesterolemic action of sesamin in rats. Internat J Vit Nutr Res 65: 162–168, 1995
Jiong-Yan GU, Tsujitha K, Yamada YK, Sugano M: Combined effects of sesamin with alpha tocopherol or tocotrienols on lipid and immune indices in brown Norway rats. Nutr Res 17: 339–350, 1997
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Ghafoorunissa, Hemalatha, S. & Rao, M.V.V. Sesame lignans enhance antioxidant activity of vitamin E in lipid peroxidation systems. Mol Cell Biochem 262, 195–202 (2004). https://doi.org/10.1023/B:MCBI.0000038235.01389.a9
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DOI: https://doi.org/10.1023/B:MCBI.0000038235.01389.a9