Gamma-tocopherol Detoxification of Nitrogen Dioxide: Superiority to Alpha-tocopherol

Overview

Journal Proc Natl Acad Sci U S A

Specialty Science

Date 1993 Mar 1

PMID 8446589

Citations 84

Authors

R V Cooney

A A Franke

P J Harwood

L J Custer

L J Mordan

Affiliations

Soon will be listed here.

Abstract

In the vitamin E group, alpha-tocopherol is generally considered to be the most potent antioxidant with the highest vitamin bioactivity, yet gamma-tocopherol is produced in greater amounts by many plants and is the principal tocopherol in the United States diet. This report describes a fundamental difference in the chemical reactivities of alpha-tocopherol and gamma-tocopherol with nitrogen dioxide (NO2), which leads to the formation of a nitrosating agent from alpha-tocopherol, but not from gamma-tocopherol. Nitric oxide (NO) is a major product of the reaction of gamma-tocopherol with NO2, while alpha-tocopherol reacts with NO2 to form an intermediate tocopheroxide analogue. The biological significance of gamma-tocopherol is suggested by limited epidemiological data as well as the observation that it is a more potent inhibitor than alpha-tocopherol of neoplastic transformation during the postinitiation phase in 3-methylcholanthrene-treated C3H/10T1/2 murine fibroblasts. This latter property suggests the superiority of gamma-tocopherol in a mammalian biological assay and a role for endogenous NO production in promotion of neoplastic transformation.

Citing Articles

The Role of Vitamin E Isoforms and Metabolites in Cancer Prevention: Mechanistic Insights into Sphingolipid Metabolism Modulation.

Jang Y, Kim C Nutrients. 2024; 16(23).

PMID: 39683509 PMC: 11644559. DOI: 10.3390/nu16234115.

Associations between Plasma Tocopherols and Lung Cancer Risk: Results from the Southern Community Cohort Study.

Yoon H, Wu J, Shidal C, Sun Y, Franke A, Yang J Cancer Epidemiol Biomarkers Prev. 2024; 33(4):480-488.

PMID: 38284815 PMC: 10990776. DOI: 10.1158/1055-9965.EPI-23-1107.

Conductometric Studies of Formation the Inclusion Complexes of Phenolic Acids with β-Cyclodextrin and 2-HP-β-Cyclodextrin in Aqueous Solutions.

Kinart Z Molecules. 2023; 28(1).

PMID: 36615484 PMC: 9822027. DOI: 10.3390/molecules28010292.

Current Naturopathy to Combat Alzheimer's Disease.

Chakrovorty A, Bhattacharjee B, Saxena A, Samadder A, Nandi S Curr Neuropharmacol. 2022; 21(4):808-841.

PMID: 36173068 PMC: 10227918. DOI: 10.2174/1570159X20666220927121022.

δ-Tocotrienol is the Most Potent Vitamin E Form in Inhibiting Prostate Cancer Cell Growth and Inhibits Prostate Carcinogenesis in Ptenp-/- Mice.

Wang H, Yan W, Sun Y, Yang C Cancer Prev Res (Phila). 2022; 15(4):233-245.

PMID: 35144931 PMC: 8984964. DOI: 10.1158/1940-6207.CAPR-21-0508.

References

Klepper L . Nitric Oxide Emissions from Soybean Leaves during in Vivo Nitrate Reductase Assays. Plant Physiol. 1987; 85(1):96-9. PMC: 1054210. DOI: 10.1104/pp.85.1.96. View

Marletta M, Yoon P, Iyengar R, Leaf C, Wishnok J . Macrophage oxidation of L-arginine to nitrite and nitrate: nitric oxide is an intermediate. Biochemistry. 1988; 27(24):8706-11. DOI: 10.1021/bi00424a003. View

Potischman N, Herrero R, Brinton L, REEVES W, Stacewicz-Sapuntzakis M, Jones C . A case-control study of nutrient status and invasive cervical cancer. II. Serologic indicators. Am J Epidemiol. 1991; 134(11):1347-55. DOI: 10.1093/oxfordjournals.aje.a116037. View

Cooney R, Ross P, Bartolini G . N-nitrosation and N-nitration of morpholine by nitrogen dioxide: inhibition by ascorbate, glutathione and alpha-tocopherol. Cancer Lett. 1986; 32(1):83-90. DOI: 10.1016/0304-3835(86)90042-x. View

McLaughlin P, Weihrauch J . Vitamin E content of foods. J Am Diet Assoc. 1979; 75(6):647-65. View

Patnaik R, Nair P . Studies on the binding of d-alpha-tocopherol to rat liver nuclei. Arch Biochem Biophys. 1977; 178(2):333-41. DOI: 10.1016/0003-9861(77)90201-6. View

Selander H, Nilsson J . Vitamin E and air pollution. Nitrogen dioxide oxidation of -tocopherol model compound. Acta Pharm Suec. 1972; 9(2):125-8. View

Wink D, Kasprzak K, Maragos C, Elespuru R, Misra M, Dunams T . DNA deaminating ability and genotoxicity of nitric oxide and its progenitors. Science. 1991; 254(5034):1001-3. DOI: 10.1126/science.1948068. View

Pryor W, Lightsey J . Mechanisms of nitrogen dioxide reactions: initiation of lipid peroxidation and the production of nitrous Acid. Science. 1981; 214(4519):435-7. DOI: 10.1126/science.214.4519.435. View

10.

Zhang L, Cooney R, Bertram J . Carotenoids enhance gap junctional communication and inhibit lipid peroxidation in C3H/10T1/2 cells: relationship to their cancer chemopreventive action. Carcinogenesis. 1991; 12(11):2109-14. DOI: 10.1093/carcin/12.11.2109. View

11.

Tran K, Chan A . Comparative uptake of alpha- and gamma-tocopherol by human endothelial cells. Lipids. 1992; 27(1):38-41. DOI: 10.1007/BF02537056. View

12.

Toth B, Patil K . Enhancing effect of vitamin E on murine intestinal tumorigenesis by 1,2-dimethylhydrazine dihydrochloride. J Natl Cancer Inst. 1983; 70(6):1107-11. View

13.

Busse R, Mulsch A . Induction of nitric oxide synthase by cytokines in vascular smooth muscle cells. FEBS Lett. 1990; 275(1-2):87-90. DOI: 10.1016/0014-5793(90)81445-t. View

14.

Reznikoff C, Bertram J, Brankow D, HEIDELBERGER C . Quantitative and qualitative studies of chemical transformation of cloned C3H mouse embryo cells sensitive to postconfluence inhibition of cell division. Cancer Res. 1973; 33(12):3239-49. View

15.

Lowry T, SCHUMAN L . Silo-filler's disease; a syndrome caused by nitrogen dioxide. J Am Med Assoc. 1956; 162(3):153-60. DOI: 10.1001/jama.1956.02970200001001. View

16.

Barinaga M . Is nitric oxide the "retrograde messenger"?. Science. 1991; 254(5036):1296-7. DOI: 10.1126/science.1962189. View

17.

BIERI J, Evarts R . Gamma tocopherol: metabolism, biological activity and significance in human vitamin E nutrition. Am J Clin Nutr. 1974; 27(9):980-6. DOI: 10.1093/ajcn/27.8.980. View

18.

MIRVISH S, Babcook D, Deshpande A, Nagel D . Identification of cholesterol as a mouse skin lipid that reacts with nitrogen dioxide to yield a nitrosating agent, and of cholesteryl nitrite as the nitrosating agent produced in a chemical system from cholesterol. Cancer Lett. 1986; 31(1):97-104. DOI: 10.1016/0304-3835(86)90171-0. View

19.

Hollstein M, Sidransky D, Vogelstein B, Harris C . p53 mutations in human cancers. Science. 1991; 253(5015):49-53. DOI: 10.1126/science.1905840. View

20.

Tannenbaum S, Mergens W . Reaction of nitrite with vitamins C and E. Ann N Y Acad Sci. 1980; 355:267-79. DOI: 10.1111/j.1749-6632.1980.tb21345.x. View