The ldentification of High Molecular Weight Polynuclear Aromatic Hydrocarbons in a Biologically Active Fraction of Cigarette Smoke Condensate

Abstract

A gel filtration chromatography method was developed for the isolation and concentration of the high molecular weight polynuclear aromatic hydrocarbons (PAH) contained in the most biologically active fraction of cigarette smoke condensate (CSC). The unusually complex mixture of large PAH found in CSC necessitated the use of preparative gas chromatography followed by high-pressure liquid chromatography to achieve separation and identification. Mass spectral, ultra-violet absorption, and chromatographic retention data were needed for the comprehensive identification of the large molecular weight PAH components of CSC. The majority of the more than 200 isolated compounds were identified. Compounds newly identified in CSC included 3,4-dimethylenepyrene, 3,4-trimethylenepyrene, cyclopenta(c,-d)pyrene, 4,5-methylenetriphenylene, benzo[b]perylene, and several dibenzofluoranthenes.

Protective effect of dietary tomatine against dibenzo[a,l]pyrene (DBP)‐induced liver and stomach tumors in rainbow trout

“…As a prerequisite to the tumor study, the acute toxicity of tomatine added to a control diet fed orally to rainbow trout was determined. DBP, a planar polyaromatic hydrocarbon, is a potent environmental hydrocarbon [12] and has been identified as a combustion product in coal smoke [13] and tobacco smoke [14]. DBP is a potent tumor initiator in mouse skin and rat mammary gland [12,15,16].…”

Formation of stable adducts and absence of depurinating DNA adducts in cells and DNA treated with the potent carcinogen dibenzo[ a,l ]pyrene or its diol epoxides

“…It has been detected in several environmental soil and sediment samples (12), in a biologically active fraction of cigarette smoke condensate (13), and in the particulates formed by combustion of smoky coal (14). DB[a,l]P is highly mutagenic in MCL-5 cells, a cell line derived from human B-lymphoblastoid cells that expresses several transfected cytochrome P450 genes and thus is capable of metabolizing PAH (15).…”

Intercalation of the (1R,2S,3R,4S)-N6-[1-(1,2,3,4- Tetrahydro-2,3,4-trihydroxybenz[a]anthracenyl)]-2‘-deoxyadenosyl Adduct in the N-ras Codon 61 Sequence: DNA Sequence Effects

“…The latter was intercalated 5′ to the modified adenine. The notion that sequence effects might be operative came from structural (34,44) and site-specific mutagenesis studies (45) with the adenyl N 6 benzo[a]pyrene SRSR (61,2) and (61,3) adducts, located at the first and second adenines of the ras61 oligodeoxynucleotide. For those BP adducts, the adduct located at the (61,2) position exhibited a single conformation, whereas the adduct located at the (61,3) position was described as a mixture of two conformations in equilibrium (27,28).…”

“…The structural refinement for the BA RSRS (61,3) adduct reveals that the BA moiety intercalates above the 5′-face of the modified base pair from the major groove. Two sequence effects are noted, when the BA RSRS (61,3) adduct is compared with the BA RSRS (61,2) adduct (33). First, the PAH moiety stacks with the adenine base at A 6 .…”