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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

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

Huadong Chen, Dominique N Soroka, Yuhui Hu, Xiaoxin Chen, Shengmin Sang

Mol Nutr Food Res. 2013 Mar;57(3):447-58.

PMID: 23322393

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP36700455	8-Shogaol		36700-45-5	Price

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