Gamma-tocopherol detoxification of nitrogen dioxide: superiority to alpha-tocopherol
Open accessAbstract
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.
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From Dietary factors and low-grade inflammation in relation to overweight and obesity (2011) · cites this paper as [56]
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- Authors
- Cooney, R. V., Franke, A. A., Harwood, P. J., Hatch-Pigott, V, Custer, L. J., & Mordan, L. J.
- Affiliations
- University of Hawaiʻi at Mānoa (US)
- Cancer Research Center of Hawaii, University of Hawaii, Honolulu 96813.
- ORCID
- Franke, A A
- Venue
- Proceedings of the National Academy of Sciences
- Publisher
- National Academy of Sciences
- Published
- 1993-03
- Volume
- 90
- Issue
- 5
- Pages
- 1771-1775
- ISSN
- 0027-8424 (ISSN-L)
- 1091-6490
- PMC
- PMC45961
- OpenAlex
- W2060644706
- Cited by
- 343
- References
- 42
- Citations by year
- 2026: 1 · 2025: 6 · 2024: 5 · 2023: 4 · 2022: 7 · 2021: 5 · 2020: 7 · 2019: 4 · 2018: 6 · 2017: 11 · 2016: 7 · 2015: 7 · 2014: 11 · 2013: 11 · 2012: 17
- FWCI
- 3.31
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- Proceedings of the National Academy of Sciences (publishedVersion)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Institutes of Health (5r29es004302-05, 5r01ca051498-03)
- National Cancer Institute (CA-51498)
- National Institute of Environmental Health Sciences (ES04302)
- Topics
- Health Sciences › Medicine › Biochemistry › Antioxidant Activity and Oxidative Stress
- Health Sciences › Medicine › Biochemistry › Phytochemicals and Antioxidant Activities
- Physical Sciences › Chemistry › Organic Chemistry › Edible Oils Quality and Analysis
- Keywords
- gamma-tocopherol, alpha-tocopherol, vitamin E, nitrogen dioxide, nitrosation, nitric oxide, antioxidant activity, oncogenic transformation, 3-methylcholanthrene, endogenous nitric oxide
- MeSH terms
- Animals, Antioxidants, Cell Line, Cell Transformation, Neoplastic, Nitric Oxide, Nitrogen Dioxide, Vitamin E, Mice, In Vitro Techniques
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