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Effect ofd-α-tocopherol analogues on lipoxygenase-dependent peroxidation of phospholipid-bile salt micelles

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Lipids

Abstract

In order to know whether or not vitamin E acts as an effective antioxidant in lipoxygenase-dependent peroxidation of phospholipids, the effect of vitamin E and vitamin E analogues, 2,2,5,7,8-pentamethyl-6-hydrohychroman (PMC) and 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox C), was investigated in enzymatic lipid peroxidation of bile salt micelles of pig liver phosphatidylcholine (PC) using soybean lipoxygenase. 15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid was exlusively produced by the reaction with the PC molecular species containing arachidonic acid moiety, indicating that the hydroperoxidation of pig liver PC entirely progresses through the enzymatic reaction. PMC suppressed the accumulation of PC-hydroperoxides (PC-OOH) more efficiently than eitherd-α-tocopherol (α-Toc) or Trolox C, and 50% inhibition concentration by PMC was close to that of quercetin, a known lipoxygenase inhibitor from natural origin. The antioxidant activity of PMC was also superior to that of either α-Toc or Trolox C in ferrous ion-induced nonenzymatic oxidation of PC micelles in the presence of a trace amount of PC-OOH, although the radical-scavenging activities of these compounds in solution were similar or comparable to one another. In conclusion, PMC is more effective than α-Toc as an inhibitor of lipoxygenase reaction with phospholipids and of autoxidation in phospholipids. The phytyl chain of α-Toc seems to be unfavorable for exerting an inhibitory effect on lipoxygenase reaction with phospholipid-bile salt micelles.

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Abbreviations

AMVN:

2,2′-azobis-(2,4-dimethylvaleronitrile)

BHA:

butylated hydroxyanisole [2(3)-tert-butyl-4-methoxyphenol]

15-HPETE:

15-hydroperoxy-5,8,11,13-eicosatetraenoic acid

HPLC:

high-performance liquid chromatography

IC50 :

50% inhibition concentrations

MeL-OOH:

methyl linoleate hydroperoxides

PC:

phosphatidylcholine

PC-OOH:

phosphatidylcholine hydroperoxides

PMC:

2,2,5,7,8-pentamethyl-6-hydroxychroman

SA-PC:

1-stearoyl-2-arachidonyl phosphatidylcholine

TBARS:

thiobarbiturac acid reacting substances

α-Toc:

d-α-Tocopherol

Trolox C:

6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid

UV:

ultraviolet

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Authors and Affiliations

  1. Department of Food Science and Technology, Faculty of Fisheries, Hokkaido University, 041, Hokkaido, Japan

    Hirofumi Arai, Tetsuya Suzuki & Kozo Takama

  2. National Food Research Institute, Ministry of Agriculture, Forestry and Fisheries, Kannondai, 305, Tsukuba Ibaraki, Japan

    Akihiko Nagao & Junji Terao

Authors
  1. Hirofumi Arai
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  2. Akihiko Nagao
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  3. Junji Terao
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  4. Tetsuya Suzuki
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  5. Kozo Takama
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Arai, H., Nagao, A., Terao, J. et al. Effect ofd-α-tocopherol analogues on lipoxygenase-dependent peroxidation of phospholipid-bile salt micelles. Lipids 30, 135–140 (1995). https://doi.org/10.1007/BF02538266

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  • DOI: https://doi.org/10.1007/BF02538266

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