Enzymatic reduction of xenobiotic alpha,beta-unsaturated ketones: formation of allyl alcohol metabolites from shogaol and dehydroparadol.
A novel reductive metabolism of shogaol [1-(4'-hydroxy-3'-methoxyphenyl)-deca-4-ene-3-one], a major pungent and pharmacologically active principle of ginger, was investigated in rat liver in vitro. The ethyl acetate extractable metabolites formed by incubation of this alpha,beta-unsaturated ketone with rat liver 12,000 x g supernatant fortified with NADPH-generating system were analyzed by high performance chromatography and gas chromatography/mass spectrometry. In addition to the saturated ketone and reduced alcohol metabolites, an allyl alcohol, 1-(4'-hydroxy-3'-methoxyphenyl)-deca-4-ene-3-ol, was identified as a new metabolite of shogaol. Likewise, dehydroparadol [1-(4'-hydroxy-3'-methoxyphenyl)-deca-1-ene-3-one], a non-pungent analog of shogaol, was also reduced to the corresponding allyl alcohol by the postmitochondrial fraction of rat kidney in the presence of NADPH-generating system.
Surh
Y J
YJ
Laboratory of Biochemistry, College of Pharmacy, Seoul National University, Korea.
Lee
S S
SS
D000433:1-Propanol / Q000378:metabolism; D000498:Allyl Compounds / Q000378:metabolism; D000818:Animals; D002396:Catechols / Q000138:chemical synthesis / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D008401:Gas Chromatography-Mass Spectrometry; D006139:Guaiacol / Q000031:analogs & derivatives* / Q000378:metabolism; D007668:Kidney / Q000201:enzymology / Q000378:metabolism*; D008099:Liver / Q000201:enzymology / Q000378:metabolism*; D008297:Male; D009153:Mutagens / Q000138:chemical synthesis / Q000378:metabolism*; D010084:Oxidation-Reduction; D010936:Plant Extracts / Q000378:metabolism*; D020005:Propanols; D051381:Rats; D017207:Rats, Sprague-Dawley
D000498:Allyl Compounds; D002396:Catechols; D009153:Mutagens; D010936:Plant Extracts; D020005:Propanols; C006463:allyl alcohol; C088509:dehydroparadol; D006139:Guaiacol; C040115:shogaol; D000433:1-Propanol