Document Detail

Identification and quantitation of novel vitamin E metabolites, sulfated long-chain carboxychromanols, in human A549 cells and in rats.
MedLine Citation:
PMID:  17299205     Owner:  NLM     Status:  MEDLINE    
The metabolism of vitamin E involves oxidation of the phytyl chain to generate the terminal metabolite 7,8-dimethyl-2-(beta-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, approximately 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 beta-oxidation. In addition, the HPLC fluorescence assay is a useful tool for the investigation of vitamin E metabolism.
Qing Jiang; Helene Freiser; Karl V Wood; Xinmin Yin
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2007-02-13
Journal Detail:
Title:  Journal of lipid research     Volume:  48     ISSN:  0022-2275     ISO Abbreviation:  J. Lipid Res.     Publication Date:  2007 May 
Date Detail:
Created Date:  2007-05-02     Completed Date:  2007-06-22     Revised Date:  2014-09-11    
Medline Journal Info:
Nlm Unique ID:  0376606     Medline TA:  J Lipid Res     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1221-30     Citation Subset:  IM    
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MeSH Terms
Cell Line
Chromans / analysis*,  chemistry,  metabolism*
Chromatography, High Pressure Liquid
Molecular Structure
Rats, Wistar
Spectrometry, Fluorescence
Sulfates / chemistry*
Vitamin E / analysis*,  chemistry,  metabolism*
Grant Support
R01 AT-001821/AT/NCCAM NIH HHS; R01 AT001821/AT/NCCAM NIH HHS; R01 AT001821-03/AT/NCCAM NIH HHS; R01 AT001821-04/AT/NCCAM NIH HHS; R01 AT001821-05/AT/NCCAM NIH HHS
Reg. No./Substance:
0/Chromans; 0/Sulfates; 1406-18-4/Vitamin E; 950-99-2/2,2,5,7,8-pentamethyl-1-hydroxychroman

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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