Analysis of cyclopentafused isomers of benz(a)anthracene in wood smoke

Abstract

A previously-unidentified peak occurring in chromatograms of the polycyclic aromatic hydrocarbon fraction from wood smoke particulate extracts analysed by capillary gas chromatography on a DB-5 column was found to correspond in retention index and molecular mass either to benzo(a)fluoranthene or to benzo(1)aceanthrylene, one of a series of four novel and highly mutagenic cyclopentafused isomers of benz(a)anthracene. Detailed subfractionation, and re-analysis on a liquid crystal capillary column, indicated that the identity of this peak was most likely to be benzo(a)fluoranthene, a compound not previously reported in woodsmoke.

Detection of Benz[j]aceanthrylene in Urban Air and Evaluation of Its Genotoxic Potential

“…15,16 Trace amounts of B[j]A have been found in the emissions from coalfired residential furnaces and hard-coal combustion, 21,22 but not in wood smoke PM. 23 Air Sampling. Two collection sites for air PM were used: Stockholm University, Stockholm, Sweden and the Faculty of Technology, UNICAMP, Limeira, Brazil.…”

“…15,16 Trace amounts of B[j]A have been found in the emissions from coalfired residential furnaces and hard-coal combustion, 21,22 but not in wood smoke PM. 23 Substituted B[j]As, such as 3-methyland 1,2-dihydro-3-methyl-B[j]A, have been determined in coal tar pitch, cigarette smoke, and air PM. 24−27 To date, very few studies have analyzed the levels of B[j]A in air PM 28 and to the authors' knowledge, no epidemiological studies have investigated the carcinogenicity of B[j]A.…”

“…One poorly studied PAH that has shown high carcinogenic potential is benz­[ j ]­aceanthrylene (B­[ j ]­A). , B­[ j ]­A is a cyclopenta-fused and bay-region containing PAH. As with other PAHs B­[ j ]­A requires metabolic activation in order to exert is biological activity and studies have identified two major routes of activation: epoxidation of the cyclopenta-ring, resulting in the B­[ j ]­A-1,2-epoxide, and diol-epoxidation of the bay-region, resulting in the B­[ j ]­A-9,10-diol-7,8-epoxide. ,, The former is the major metabolite found as a 1,2-diol in human and rat liver tissues and cells. , B­[ j ]­A is a potent bacterial and mammalian cell mutagen and is more tumorigenic than B­[ a ]P in SENCAR mice and in A/J mice lung. , Trace amounts of B­[ j ]­A have been found in the emissions from coal-fired residential furnaces and hard-coal combustion, , but not in wood smoke PM . Substituted B­[ j ]­As, such as 3-methyl- and 1,2-dihydro-3-methyl-B­[ j ]­A, have been determined in coal tar pitch, cigarette smoke, and air PM. − To date, very few studies have analyzed the levels of B­[ j ]­A in air PM and to the authors’ knowledge, no epidemiological studies have investigated the carcinogenicity of B­[ j ]­A.…”