Skip to main content
PMC home page
Biochemical Journal logoLink to Biochemical Journal
. 1965 Oct;97(1):7–16. doi: 10.1042/bj0970007

The metabolism of benz[a]anthracene and dibenz[a,h]anthracene and their 5,6-epoxy-5,6-dihydro derivatives by rat-liver homogenates

E Boyland 1, P Sims 1
PMCID: PMC1264537  PMID: 16749126

Abstract

1. Benz[a]anthracene was hydroxylated by rat-liver homogenates on the 3,4-,5,6- or 8,9-bond to yield phenols and dihydrodihydroxy compounds. Metabolic action at the 7- and 12-positions was also detected. 5,6-Epoxy-5,6-dihydrobenzanthracene was converted into a phenol that is probably 5-hydroxybenzanthracene and 5,6-dihydro-5,6-dihydroxybenzanthracene. Both substrates yielded a product that is probably S-(5,6-dihydro-6-hydroxy-5-benzanthracenyl)glutathione. 2. Dibenz[a,h]anthracene was hydroxylated by rat-liver homogenates to yield products that are probably 3- and 4-hydroxydibenzanthracene, 1,2-dihydro-1,2-dihydroxydibenzanthracene, 3,4-dihydro-3,4-dihydroxydibenzanthracene and 5,6-dihydro-5,6-dihydroxydibenzanthracene. There was no evidence for metabolic action at the 7- and 14-positions. 5,6-Epoxy-5,6-dihydrodibenzanthracene was converted into a phenol that is probably 5-hydroxydibenzanthracene and 5,6-dihydro-5,6-dihydroxydibenzanthracene. Both substrates yielded a glutathione conjugate that is probably S-(5,6-dihydro-6-hydroxy-5-dibenzanthracenyl)glutathione. 3. The synthesis of 5,6-epoxy-5,6-dihydrodibenzanthracene is described and the reactions of this epoxide and 5,6-epoxy-5,6-dihydrobenzanthracene with water and thiols have been investigated. 4. The oxidation of dibenzanthracene in the ascorbic acid–Fe2+ ion–oxygen model system is described.

Full text

PDF
7

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. BOYLAND E., SIMS P. METABOLISM OF POLYCYCLIC COMPOUNDS. THE METABOLISM OF 7,12-DIMETHYLBENZ(ALPHA)ANTHRACENE BY RAT-LIVER HOMOGENATES. Biochem J. 1965 Jun;95:780–787. doi: 10.1042/bj0950780. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. BOYLAND E., SIMS P. METABOLISM OF POLYCYCLIC COMPOUNDS. THE METABOLISM OF 9,10-EPOXY-9,10-DIHYDROPHENANTHRENE IN RATS. Biochem J. 1965 Jun;95:788–792. doi: 10.1042/bj0950788. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. BOYLAND E., SIMS P. Metabolism of polycyclic compounds. 12. An acid-labile precursor of 1-naphthylmercapturic acid and naphthol: an N-acetyl-S-(1:2-dihydrohydroxy-naphthyl)-L-cysteine. Biochem J. 1958 Mar;68(3):440–447. doi: 10.1042/bj0680440. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. BOYLAND E., SIMS P. Metabolism of polycyclic compounds. 20. The metabolism of phenanthrene in rabbits and rats: mercapturic acids and related compounds. Biochem J. 1962 Sep;84:564–570. doi: 10.1042/bj0840564. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. BOYLAND E., WILLIAMS K. AN ENZYME CATALYSING THE CONJUGATION OF EPOXIDES WITH GLUTATHIONE. Biochem J. 1965 Jan;94:190–197. doi: 10.1042/bj0940190. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Boyland E., Kumura M., Sims P. Metabolism of polycyclic compounds. 26. The hydroxylation of some aromatic hydrocarbons by the ascorbic acid model hydroxylating system and by rat-liver microsomes. Biochem J. 1964 Sep;92(3):631–638. doi: 10.1042/bj0920631. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Boyland E., Levi A. A., Mawson E. H., Roe E. Metabolism of polycyclic compounds: Production of a dihydroxy-1:2:5:6-dibenzanthracene from 1:2:5:6-dibenzanthracene. Biochem J. 1941 Jan;35(1-2):184–191. doi: 10.1042/bj0350184. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Boyland E., Ramsay G. S., Sims P. Metabolism of polycyclic compounds. 18. The secretion of metabolites of naphthalene, 1:2-dihydronaphthalene and 1:2-epoxy-1:2:3:4-tetrahydronaphthalene in rat bile. Biochem J. 1961 Feb;78(2):376–384. doi: 10.1042/bj0780376. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Boyland E., Sims P. Metabolism of polycyclic compounds. 23. The metabolism of pyrene in rats and rabbits. Biochem J. 1964 Feb;90(2):391–398. doi: 10.1042/bj0900391. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Boyland E., Sims P. Metabolism of polycyclic compounds. 24. The metabolism of benz[alpha]anthracene. Biochem J. 1964 Jun;91(3):493–506. doi: 10.1042/bj0910493. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. HEIDELBERGER C., WIEST W. G. The metabolic degradation in the mouse of 1,2,5,6-dibenzanthracene-9,10-C14. II. 5-Hydroxy-1,2-naphthalic acid, a new metabolite. Cancer Res. 1951 Jul;11(7):511–518. [PubMed] [Google Scholar]
  12. Sims P. Metabolism of polycyclic compounds. 25. The metabolism of anthracene and some related compounds in rats. Biochem J. 1964 Sep;92(3):621–631. doi: 10.1042/bj0920621. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Biochemical Journal are provided here courtesy of The Biochemical Society

RESOURCES