ArticleDrug metabolism and disposition: the biological fate of chemicals2012
Metabolism of [6]-shogaol in mice and in cancer cells.
Article in Drug metabolism and disposition: the biological fate of chemicals, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed.
- Phase II Metabolite-Inspired Tripeptide Editing Generates Anti-Inflammatory Candidates for Treatment-Refractory Ulcerative Colitis.International journal of molecular sciences · 2026Article
- Shogaol: A Natural Treasure from Ginger with Promising Therapeutic Applications.Chinese journal of integrative medicine · 2025Review
- Review of the anticancer properties of 6-shogaol: Mechanisms of action in cancer cells and future research opportunities.Food science & nutrition · 2024Review
- Article
- Anticancer perspective of 6-shogaol: anticancer properties, mechanism of action, synergism and delivery system.Chinese medicine · 2023Review
- Impact of Sulfur Fumigation on Ginger: Chemical and Biological Evidence.Journal of agricultural and food chemistry · 2022Article
- Pharmacokinetics of Gingerols, Shogaols, and Their Metabolites in Asthma Patients.Journal of agricultural and food chemistry · 2022Article
- Mechanisms of Chemopreventive and Therapeutic Proprieties of Ginger Extracts in Cancer.International journal of molecular sciences · 2021Review
- Pungent and volatile constituents of dried Australian ginger.Current research in food science · 2021Article
- Natural-lipid nanoparticle-based therapeutic approach to deliver 6-shogaol and its metabolites M2 and M13 to the colon to treat ulcerative colitis.Journal of controlled release : official journal of the Controlled Release Society · 2020Article
- Gingers and Their Purified Components as Cancer Chemopreventative Agents.Molecules (Basel, Switzerland) · 2019Review
- Enhanced Oral Bioavailability, Anti-Tumor Activity and Hepatoprotective Effect of 6-Shogaol Loaded in a Type of Novel Micelles of Polyethylene Glycol and Linoleic Acid Conjugate.Pharmaceutics · 2019Article
- Microbiota facilitates the formation of the aminated metabolite of green tea polyphenol (-)-epigallocatechin-3-gallate which trap deleterious reactive endogenous metabolites.Free radical biology & medicine · 2019Article
- Glucuronidation of [6]-shogaol, [8]-shogaol and [10]-shogaol by human tissues and expressed UGT enzymes: identification of UGT2B7 as the major contributor.RSC advances · 2018Article
- Absorption, Metabolic Stability, and Pharmacokinetics of Ginger Phytochemicals.Molecules (Basel, Switzerland) · 2017Article
- 6-Paradol and 6-Shogaol, the Pungent Compounds of Ginger, Promote Glucose Utilization in Adipocytes and Myotubes, and 6-Paradol Reduces Blood Glucose in High-Fat Diet-Fed Mice.International journal of molecular sciences · 2017Article
- Gastroprotective [6]-Gingerol Aspirinate as a Novel Chemopreventive Prodrug of Aspirin for Colon Cancer.Scientific reports · 2017Article
- Intestinal, portal, and peripheral profiles of daikenchuto (TU-100)'s active ingredients after oral administration.Pharmacology research & perspectives · 2015Article
- Ginger compound [6]-shogaol and its cysteine-conjugated metabolite (M2) activate Nrf2 in colon epithelial cells in vitro and in vivo.Chemical research in toxicology · 2014Article
- Cysteine-conjugated metabolites of ginger components, shogaols, induce apoptosis through oxidative stress-mediated p53 pathway in human colon cancer cells.Journal of agricultural and food chemistry · 2014Article
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9 authors.
Funding
Abstract
Ginger has received extensive attention because of its antioxidant, anti-inflammatory, and antitumor activities. However, the metabolic fate of its major components is still unclear. In the present study, the metabolism of [6]-shogaol, one of the major active components in ginger, was examined for the first time in mice and in cancer cells. Thirteen metabolites were detected and identified, seven of which were purified from fecal samples collected from [6]-shogaol-treated mice. Their structures were elucidated as 1-(4'-hydroxy-3'-methoxyphenyl)-4-decen-3-ol (M6), 5-methoxy-1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-one (M7), 3',4'-dihydroxyphenyl-decan-3-one (M8), 1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-ol (M9), 5-methylthio-1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-one (M10), 1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-one (M11), and 5-methylthio-1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-ol (M12) on the basis of detailed analysis of their (1)H, (13)C, and two-dimensional NMR data. The rest of the metabolites were identified as 5-cysteinyl-M6 (M1), 5-cysteinyl-[6]-shogaol (M2), 5-cysteinylglycinyl-M6 (M3), 5-N-acetylcysteinyl-M6 (M4), 5-N-acetylcysteinyl-[6]-shogaol (M5), and 5-glutathiol-[6]-shogaol (M13) by analysis of the MS(n) (n = 1-3) spectra and comparison to authentic standards. Among the metabolites, M1 through M5, M10, M12, and M13 were identified as the thiol conjugates of [6]-shogaol and its metabolite M6. M9 and M11 were identified as the major metabolites in four different cancer cell lines (HCT-116, HT-29, H-1299, and CL-13), and M13 was detected as a major metabolite in HCT-116 human colon cancer cells. We further showed that M9 and M11 are bioactive compounds that can inhibit cancer cell growth and induce apoptosis in human cancer cells. Our results suggest that 1) [6]-shogaol is extensively metabolized in these two models, 2) its metabolites are bioactive compounds, and 3) the mercapturic acid pathway is one of the major biotransformation pathways of [6]-shogaol.
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