Enzymatic reduction of shogaol: a novel biotransformation pathway for the alpha,beta-unsaturated ketone system.
A novel reductive metabolism of 1-(4-hydroxy-3-methoxyphenyl)-deca-4-ene-3-one (shogaol), a pungent principle of ginger, was investigated in rat liver in vitro. Ethyl acetate-extractable metabolites of shogaol formed by incubation of this alpha,beta-unsaturated ketone with rat liver cytosolic fraction fortified with NADPH or NADPH-generating system were isolated, and two major metabolites were identified as 1-(4-hydroxy-3-methoxyphenyl)-decan-3-one (paradol) and 1-(4-hydroxy-3-methoxy)-decan-3-ol (reduced paradol). 1-(4-hydroxy-3-methoxyphenyl)-deca-1-ene-3-one (dehydroparadol), a non-pungent analog of shogaol, formed the same metabolites as did shogaol under similar incubation conditions. Paradol appears to be an intermediate in the reductive metabolism of the alpha,beta-unsaturated ketone moiety of shogaol to the corresponding saturated alcohol.
Surh
Y J
YJ
College of Pharmacy, Seoul National University, Korea.
Lee
S S
SS
D000818:Animals; D001711:Biotransformation; D002396:Catechols / Q000493:pharmacokinetics*; D002855:Chromatography, Thin Layer; D008099:Liver / Q000201:enzymology; D008297:Male; D013058:Mass Spectrometry; D015394:Molecular Structure; D010936:Plant Extracts / Q000493:pharmacokinetics*; D051381:Rats; D011919:Rats, Inbred Strains; D013055:Spectrophotometry, Infrared
D002396:Catechols; D010936:Plant Extracts; C040115:shogaol