title: Mutagenicity of hexahydrophenanthrenes and their oxirane derivatives.
abstract: The mutagenicity of some hexahydrophenanthrenes and their corresponding arene oxides was assayed in histidine-dependent mutants of Salmonella typhimurium TA98 and TA100. All the arene epoxides examined were devoid of mutagenic activity, although some of them could alkylate nicotinamide. By contrast, the 1,2,3,9,10, 10a-hexahydrophenanthrene, trans-1,2,3,4,4a,10a-hexahydrophenanthrene, 9-methyl-, 6-methoxy-trans-1,2,3,4,4a,10a-hexahydrophenanthrene, 7-bromo-trans-1,2,3,4,4a,10a-hexahydrophenanthrene and 9-methyl-trans-1,2,3,4,4a,10a-hexahydrophenanthrene were active as mutagens in the presence of S9 mix. A negative result was obtained with octahydrophenanthrene, suggesting that the benzylic double bond is a prerequisite for the mutagenic activities of hexahydrophenanthrenes. Thus, probably a very reactive intermediate (aryloxirane) formed by a secondary metabolism following the primary oxidation of the benzylic double bond by S9 mix could be responsible for the mutagenicity of the hexahydrophenanthrenes.
authors.affiliation: Dipartimento di Chimica Bioorganica, Facoltà di Farmacia, Pisa, Italy.
authors.forename: P
authors.initials: P
authors.lastname: Crotti
authors.forename: V
authors.initials: V
authors.lastname: Di Bussolo
authors.forename: D
authors.initials: D
authors.lastname: Benetti
authors.forename: V
authors.initials: V
authors.lastname: Longo
authors.forename: P G
authors.initials: PG
authors.lastname: Gervasi
mesh_terms: D004852:Epoxy Compounds / Q000378:metabolism / Q000633:toxicity; D009152:Mutagenicity Tests; D009153:Mutagens / Q000633:toxicity*; D010616:Phenanthrenes / Q000378:metabolism / Q000633:toxicity*; D012486:Salmonella typhimurium
chemical_list: D004852:Epoxy Compounds; D009153:Mutagens; D010616:Phenanthrenes