Microsomal ring-fission of cis- and trans-acenaphthene-1,2-diol

Area of Science:

• Biochemistry
• Enzymology
• Organic Chemistry

Background:

• Acenaphthene diols are polycyclic aromatic hydrocarbon derivatives.
• Microsomes are key cellular components involved in xenobiotic metabolism.

Purpose of the Study:

• To investigate the ring-fission metabolism of cis- and trans-acenaphthene-1,2-diol.
• To identify the metabolic products and understand the reaction mechanism.

Main Methods:

• Incubation of diols with rat liver microsomes.
• Spectrophotometric monitoring of NAD+ reduction.
• Isolation and identification of metabolic products.

Main Results:

• 1,8-Naphthalic acid was identified as a major metabolite.
• Optimal pH for cis-diol oxidation was 9.4; for trans-diol, it was 9.8.
• Inhibition by p-chloromercuribenzoate and 2,4-dichlorophenol suggests enzyme involvement.

Conclusions:

• Rat liver microsomes mediate the ring-fission of acenaphthene diols.
• The reaction likely proceeds via 1,8-naphthalic aldehyde intermediate.
• Enzyme-catalyzed mechanisms are proposed for this metabolic pathway.