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© 1985 Oxford University Press

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Secondary metabolites of benzo[a]pyrene: 3-hydroxy-trans-7,8-dihydro-7,8-dihydroxybenzo[a]pyrene, a biliary metabolite of 3-hydroxybenzo[a]pyrene in the rat

Odartey Ribeiro, Charles A. Kirkby, Paul C. Hirom and Peter Millburn

Department of Biochemistry, St. Mary's Hospital Medical School Norfolk Place, London W2 1PG, UK

Rats administered 3-hydroxybenzo[a]pyrene (50 mg/kg, i.p.), excrete via the bile metabolites which, after treatment with ß-glucuronidase and aryl sulphatase, yield, in addition to 3-hydroxybenzo[a]pyrene, 3-hydroxy-trans-7,8-dihydro-7,8-dihydroxybenzo[a]pyrene (3-OH-BP-7, 8-diol) and a minor, highly labile, metabolite tentatively identified as 3,5-dihydroxybenzo[a]pyrene. These novel metabolites are readily isolated in a pure state via preparative layer chromatography. The structure of the 3-OH-BP-7, 8-diol was revealed by its u.v., proton magnetic resonance and mass spectral properties. Its hydroxyl functions are in a predominantly quasi-diequatorial conformation.


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