Document Detail


Metabolism of ginger component [6]-shogaol in liver microsomes from mouse, rat, dog, monkey, and human.
MedLine Citation:
PMID:  23322474     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
SCOPE: There are limited data on the metabolism of [6]-shogaol (6S), a major bioactive component of ginger. This study demonstrates metabolism of 6S in liver microsomes from mouse, rat, dog, monkey, and human.
METHODS AND RESULTS: The in vitro metabolism of 6S was compared among five species using liver microsomes from mouse, rat, dog, monkey, and human. Following incubations with 6S, three major reductive metabolites 1-(4'-hydroxy-3'-methoxyphenyl)-4-decen-3-ol (M6), 1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-ol (M9), and 1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-one (M11), as well as two new oxidative metabolites (1E,4E)-1-(4'-hydroxy-3'-methoxyphenyl)-deca-1,4-dien-3-one (M14) and (E)-1-(4'-hydroxy-3'-methoxyphenyl)-dec-1-en-3-one (M15) were found in all species. The kinetic parameters of M6 in liver microsomes from each respective species were quantified using Michaelis-Menten theory. A broad CYP-450 inhibitor, 1-aminobenzotriazole, precluded the formation of oxidative metabolites, M14 and M15, and 18β-glycyrrhetinic acid, an aldo-keto reductase inhibitor, eradicated the formation of the reductive metabolites M6, M9, and M11 in all species. Metabolites M14 and M15 were tested for cancer cell growth inhibition and induction of apoptosis and both showed substantial activity, with M14 displaying greater potency than 6S.
CONCLUSION: We conclude that 6S is metabolized extensively in mammalian species mouse, rat, dog, monkey, and human, and that there are significant interspecies differences to consider when planning preclinical trials toward 6S chemoprevention.
Authors:
Huadong Chen; Dominique Soroka; Yingdong Zhu; 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 May 
Date Detail:
Created Date:  2013-04-16     Completed Date:  2013-12-03     Revised Date:  2014-05-07    
Medline Journal Info:
Nlm Unique ID:  101231818     Medline TA:  Mol Nutr Food Res     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  865-76     Citation Subset:  IM    
Copyright Information:
© 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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MeSH Terms
Descriptor/Qualifier:
Alcohol Oxidoreductases / antagonists & inhibitors,  metabolism
Animals
Catechols / pharmacology*
Cell Line, Tumor
Chemoprevention
Chromatography, High Pressure Liquid
Cytochrome P-450 Enzyme System / antagonists & inhibitors,  metabolism
Dogs
Gas Chromatography-Mass Spectrometry
Ginger / chemistry*
Glycyrrhetinic Acid / analogs & derivatives,  pharmacology
Haplorhini
Humans
Magnetic Resonance Spectroscopy
Mice
Microsomes, Liver / metabolism*
Plant Extracts / pharmacology*
Rats
Rats, Sprague-Dawley
Triazoles / pharmacology
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/Catechols; 0/Plant Extracts; 0/Triazoles; 1449-05-4/18alpha-glycyrrhetinic acid; 1614-12-6/1-aminobenzotriazole; 83DNB5FIRF/shogaol; 9035-51-2/Cytochrome P-450 Enzyme System; EC 1.1.-/Alcohol Oxidoreductases; EC 1.1.1.21/carbonyl reductase (NADPH); P540XA09DR/Glycyrrhetinic Acid
Comments/Corrections

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


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