Simulation of the hepatic metabolism of stilbene and its tricyclic derivatives by Fenton and Ruff reagents: models for cytochrome P-450 activation of chemical carcinogens.
Reactions of trans-stilbene, cis-stilbene, 5H-dibenzo [a,d] cyclo-heptene 5-one and 5H-dibenz [b,f] azepine (iminostilbene) with Fenton reagent [Fe (II)/H2O2] clearly simulate their hepatic metabolism. Expoxidation on the corresponding ethylenic linkage was found to be a common pathway of these compounds. Epoxides of trans-stilbene, cis-stilbene, and 5H-dibenzo[a,d]cycloheptene 5-one were further oxidized to dihydrodiols, alpha-hydroxyketones, diketones, and finally cleavage of the ethylenic bonds to the formation of the corresponding aldehydes. However, the unstable epoxide of iminostilbene gave 9-acridinecarbaldehyde that is further oxidized to 9-acridone. Reaction of both trans- and cis-stilbene with Ruff reagent [Fe III)/H2O2] gave the same oxidative products to that obtained from Fenton reagent. The radical scavenger 2,6 bis (1,1-dimethylethyl)-4-methyl phenol (BHT) decreases the total yield conversion and increases the formation ratio of both cis-epoxide and d,l-hydrobenzoin from cis-stilbene.
Zbaida
S
S
Department of Pharmacy, School of Pharmacy, Hebrew University of Jerusalem, Israel.
Kariv
R
R
D001711:Biotransformation; D002273:Carcinogens / Q000378:metabolism*; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism*; D003984:Dibenzazepines / Q000378:metabolism; D003986:Dibenzocycloheptenes / Q000378:metabolism; D008401:Gas Chromatography-Mass Spectrometry; D006861:Hydrogen Peroxide; D007501:Iron; D008099:Liver / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008954:Models, Biological; D013267:Stilbenes / Q000378:metabolism*
D002273:Carcinogens; D003984:Dibenzazepines; D003986:Dibenzocycloheptenes; C045076:Fenton's reagent; D013267:Stilbenes; C011222:dibenzsuberone; D003577:Cytochrome P-450 Enzyme System; D006861:Hydrogen Peroxide; D007501:Iron; C527817:dibenzazepine