Document Detail


Characterization of thiol-conjugated metabolites of ginger components shogaols in mouse and human urine and modulation of the glutathione levels in cancer cells by [6]-shogaol.
MedLine Citation:
PMID:  23322393     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
SCOPE: Shogaols, a series of major constituents in dried ginger with the most abundant being [6]-, [8]-, and [10]-shogaols, show much higher anticancer potencies than gingerols. Previously, we reported the mercapturic acid pathway as a major metabolic route for [6]-shogaol in mice. However, it is still unclear how the side chain length affects the metabolism of shogaols and how shogaols are metabolized in humans.
METHODS AND RESULTS: We first investigate the metabolism of [10]-shogaol in mouse urine, and then investigate the biotransformation of shogaols in human urine. Our results show that eight major thiol-conjugated metabolites of [10]-shogaol were detected in mouse urine, while six major thiol-conjugated metabolites of [6]-shogaol, two thiol-conjugated metabolites of [8]-shogaol, and two thiol-conjugated metabolites of [10]-shogaol were detected in urine collected from human after drinking ginger tea, using LC/ESI-MS/MS. Our results clearly indicate the mercapturic acid pathway is a major metabolic route for [10]-shogaol in mice and for shogaols in human. Furthermore, we also investigated the regulation of glutathione (GSH) by [6]-shogaol in human colon cancer cells HCT-116. Our results show [6]-shogaol, after initially depleting glutathione levels, can subsequently restore and increase GSH levels over time.
CONCLUSION: Shogaols are metabolized extensively in mouse and human to form thiol-conjugated metabolites and GSH might play an important role in the cancer-preventive activity of ginger.
Authors:
Huadong Chen; Dominique N Soroka; Yuhui Hu; Xiaoxin Chen; Shengmin Sang
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2013-01-16
Journal Detail:
Title:  Molecular nutrition & food research     Volume:  57     ISSN:  1613-4133     ISO Abbreviation:  Mol Nutr Food Res     Publication Date:  2013 Mar 
Date Detail:
Created Date:  2013-03-15     Completed Date:  2013-12-23     Revised Date:  2014-03-06    
Medline Journal Info:
Nlm Unique ID:  101231818     Medline TA:  Mol Nutr Food Res     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  447-58     Citation Subset:  IM    
Copyright Information:
© 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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MeSH Terms
Descriptor/Qualifier:
Acetylcysteine / metabolism
Adult
Animals
Antineoplastic Agents, Phytogenic / pharmacology
Beverages
Catechols / pharmacokinetics,  pharmacology*,  urine*
Cell Line, Tumor
Female
Ginger / chemistry*,  metabolism
Glutathione / metabolism*
Guaiacol / analogs & derivatives,  chemistry,  urine
HCT116 Cells / drug effects,  metabolism
Humans
Male
Mice
Mice, Inbred C57BL
Molecular Structure
Sulfhydryl Compounds / metabolism,  urine
Tandem Mass Spectrometry
Grant Support
ID/Acronym/Agency:
CA138277/CA/NCI NIH HHS; CA138277S1/CA/NCI NIH HHS; R21 CA138277/CA/NCI NIH HHS
Chemical
Reg. No./Substance:
0/(10)-shogaol; 0/(8)-shogaol; 0/Antineoplastic Agents, Phytogenic; 0/Catechols; 0/Sulfhydryl Compounds; 6JKA7MAH9C/Guaiacol; 83DNB5FIRF/shogaol; GAN16C9B8O/Glutathione; WYQ7N0BPYC/Acetylcysteine
Comments/Corrections

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