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Originally published In Press as doi:10.1194/jlr.D700001-JLR200 on February 13, 2007

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Journal of Lipid Research, Vol. 48, 1221-1230, May 2007
Copyright © 2007 by American Society for Biochemistry and Molecular Biology

Methods

Identification and quantitation of novel vitamin E metabolites, sulfated long-chain carboxychromanols, in human A549 cells and in rats

Qing Jiang1,*,{dagger}, Helene Freiser*,{dagger}, Karl V. Wood§ and Xinmin Yin*,{dagger}

* Interdepartmental Nutrition Program, Purdue University, West Lafayette, IN 47907
{dagger} Department of Foods and Nutrition, Purdue University, West Lafayette, IN 47907
§ Department of Chemistry, Purdue University, West Lafayette, IN 47907

Published, JLR Papers in Press, February 13, 2007.

1 To whom correspondence should be addressed. e-mail: qjiang{at}purdue.edu

The metabolism of vitamin E involves oxidation of the phytyl chain to generate the terminal metabolite 7,8-dimethyl-2-(ß-carboxyethyl)-6-hydroxychroman (CEHC) via intermediate formation of 13'-hydroxychromanol and long-chain carboxychromanols. Conjugated (including sulfated) metabolites were reported previously but were limited to CEHCs. Here, using electrospray and inductively coupled plasma mass spectrometry, we discovered that {gamma}-tocopherol ({gamma}-T) and {delta}-T were metabolized to sulfated 9'-, 11'-, and 13'-carboxychromanol (9'S, 11'S, and 13'S) in human A549 cells. To further study the metabolites, we developed a HPLC assay with fluorescence detection that simultaneously analyzes sulfated and nonconjugated intermediate metabolites. Using this assay, we found that sulfated metabolites were converted to nonconjugated carboxychromanols by sulfatase digestion. In cultured cells, ~45% long-chain carboxychromanols from {gamma}-T but only 10% from {delta}-T were sulfated. Upon supplementation with {gamma}-T, rats had increased tissue levels of 9'S, 11'S, and 13'S, 13'-hydroxychromanol, 13'-carboxychromanol, and {gamma}-CEHC. The plasma concentrations of combined sulfated long-chain metabolites were comparable to or exceeded those of CEHCs and increased proportionally with the supplement dosages of {gamma}-T. Our study identifies sulfated long-chain carboxychromanols as novel vitamin E metabolites and provides evidence that sulfation may occur parallel with ß-oxidation. In addition, the HPLC fluorescence assay is a useful tool for the investigation of vitamin E metabolism.

Supplementary key words tocopherol • tocotrienol • 7,8-dimethyl-2-(ß-carboxyethyl)-6-hydroxychroman • sulfation • metabolism • high-performance liquid chromatography • fluorescence detection

Abbreviations: {alpha}-T, ß-T, {gamma}-T, or {delta}-T, {alpha}-, ß-, {gamma}-, or {delta}-tocopherol; CEHC, 7,8-dimethyl-2-(ß-carboxyethyl)-6-hydroxychroman; 9'-, 11'-, and 13'-COOH, 9'-, 11'-, and 13'-carboxychromanol; ESI-MS, electrospray ionization mass spectrometry; ICP-MS, inductively coupled plasma mass spectrometry; 13'-OH, 13'-hydroxychromanol; 9'S, 11'S, and 13'S, sulfated 9'-, 11'-, and 13'-carboxychromanol


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Copyright © 2007 by the American Society for Biochemistry and Molecular Biology.