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
✍ Scribed by Shumel Zbaida; Rami Kariv
- Publisher
- John Wiley and Sons
- Year
- 1990
- Tongue
- English
- Weight
- 559 KB
- Volume
- 11
- Category
- Article
- ISSN
- 0142-2782
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✦ Synopsis
Abstract
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)/H~2~O~2~] clearly simulate their hepatic metabolism. Epoxidation 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, α‐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/H~2~O~2~] 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.