Smoking polycyclic hydrocarbons

CYPlAl Smoking (polycyclic aromatic hydrocarbons), char-grilled meat, omeprazole... 

Substances carcinogenic to animals (polycyclic hydrocarbons and nicotine-derived N-nitrosamines) have been identified in tobacco smoke condensates from cigarettes, cigars and pipes. Polycyclic hydrocarbons are responsible for the hepatic enzyme induction that occurs in smokers. 

This polycyclic, aromatic hydrocarbon is produced continuously by almost all plants, irrespective of their habitat, and remains qualitatively and quantitatively constant. The normal content of the carcinogenic 3.4 -benzpyrene equals 1 pg/lOO g dried plant material. (The assumed quantity of carcinogenic polycyclic hydrocarbons ingested daily with food and drinking water is calculated at 10 ig/day.) Food of animal origin, even in roasted, smoked or grilled form, contains substantially less benzpyrene than plants do. 

The polycyclic hydrocarbons in cigarette smoke are potent inducers of certain cytochrome P450 isozymes. There is a marked increase in the 2-hydroxylation of natural estradiol in smokers, but not of ethinylestradiol, suggesting that the two estrogens are metabolized by different P450 enzymes. There is thus probably no pharmacokinetic interaction between smoking and oral... 

Theophylline and polycyclic hydrocarbons in tobacco smoke (3-methylcholanthrene) represent a second type of enzyme inducer with broad induction effects. They induce CyP lA in which no change in P4go reductase occurs and a different terminal oxidase appears. After this type of induction, the clearance of tlieophylline but not that of antipyrine is increased. These substances have served as prototypes for the classification of enzyme inducers. Obviously, when patients are on a drug with a narrow therapeutic index, their dosing regimen would need to be adjusted should a known enzyme-inducing drug be added to or deleted from their therapy. 

Examples for the fluorescence detection system are the determination of quinine in soft drinks and the important quantification of benzo[a]pyrene and other polycyclic hydrocarbons (PAH) in smoke flavourings or smoke preparations [13-14]... 

Being interested here in the volatile components of coffee aroma, we shall arbitrarily limit the list of the aromatic hydrocarbons to tricyclic structures. The higher fused polycyclic hydrocarbons (fluoranthene [206-44-0], pyrene [129-00-0], chrysene [218-01-9], benz[ ]anthracene (1,2-benzanthracene) [56-55-3], benz[< ]acephenanthrylene (3,4-benzofluoranthene) [205-99-2], benzo[ ]pyrene (3,4-benzopyrene, 3,4-BP) [50-32-8], benzo[e]pyrene (1,2-benzopyrene) [192-97-2], perylene [198-55-0], benzo[g,/i,/]perylene (1,12-benzopyrene) [191-24-2], and dibenz[ ,//]anthracene (1,2,5,6-dibenzanthracene) [53-70-3]) cannot be considered as a part of the aroma. However, as some of these, specially benzo[o pyrene, are known for carcinogenic properties, they have been particularly analyzed in food subject to roasting or smoke-curing. 

At the Internet address, http //legacy.library.ucsf.edu/cgi, by inserting the topic aromatic polycyclic hydrocarbons, one may access over twenty BAT and Brown and Williamson (B W) memoranda by Chakraborty, Thornton, and others on PAHs in tobacco smoke. 

Polycyclic Hydrocarbons Reported in Tobacco Smoke by Year-End 1955... 

Several carcinogenic higher aromatic polycyclic hydrocarbons [are] present in tobacco smoke condensate. They include benzo[a]pyrene benzo[e]pyrene chrysene. .., benz[a] anthracene dibenz[a,/ ]anthracene and dibenzo[a,i] pyrene. .. From the amount in which these materials have been found in tobacco smoke condensate it was evident that these, by themselves, could not account for the total biological activity observed. 

Benzo(a)pyrene is present in much larger concentrations than is any other carcinogenic polycyclic hydrocarbon. The inability to account for the carcinogenicity of the tobacco products, except to a very minor degree, by the amonnt of benzo(a)pyrene present was unanticipated. Both Drnckrey (1056) and Wynder (4300) emphasized that the benzo(a)pyrene concentration of various tobacco and smoke preparations is only sufficient to account for a very small part of the carcinogenicity of these materials [see pp. 144-145 in (3999)]. 

Numerous pyrolytic studies have shown that the hexane or petroleum ether. .. extract of tobacco contains the major precursors of smoke polycyclic aromatic hydrocarbons [Wynder et al. (4355), Schlotzhauer et al. (3468), Schlotzhauer and Chortyk (3451)]. However, many of these studies were made under conditions which produced optimum PAH yields [Schmeltz and Hoffmann (3489)] thus, the PAH distributions were not comparable to those in [CSC] and the data obtained could not be exactly correlated with PAH production during the smoking process. 

Conversion of Tobacco Leaf Constituents to Total Mainstream Smoke Polycyclic Aromatic Hydrocarbons... 

Personal Exposure to Tobacco Smoke Polycyclic Aromatic Hydrocarbons Listed as Tumorigens... 

Allen, R.E. A rapid method for the determination of polycyclic hydrocarbons in cigarette smoke 30th Tobacco Chemists Research Conference, Program Booklet and Abstracts, Vol. 30, Paper No. 46, 1976, p. 32. 

Bilimoria, M.H., J. Johnson, M.A. Nisbet, S. Schmeller, and K.K. Georgieff Inhibition of radical initiated polymerisation of vinyl acetate by tobacco smoke and some polycyclic hydrocarbons Beitr. Tabakforsch. 7 (1973) 158-164. 

British Empire Cancer Campaign Aromatic polycyclic hydrocarbons in cigarette smoke Brit. Emp. Cancer Camp., Ann. Rpt. 35 (1958) 303-305. 

Campbell, J.M. and A.J. Lindsey Polycyclic hydrocarbons extracted from tobacco. The effect upon total quantities found in smoking Brit. J. Cancer 10 (1956) 649-652. 

Chakraborty, B.B., K.D. Kilbum, and R.E. Thornton Reduction in the concentration of aromatic polycyclic hydrocarbons in cigarette smoke Chem. and Ind. (London) (1971) 672. 

Ciaravolo, S., G. Lionetti, M. Gionti, A. Nunziata, and E. Pierri Microwave-assisted extraction An efficient method for the determination of polycyclic hydrocarbons in particulate phase mainstream cigarette smoke 2004 CORESTA Congress, Kyoto, Japan, Poster SSIO Microwave-assisted extraction An efficient method for the determination of polycychc hydrocarbons in particulate phase mainstream cigarette smoke Manuscript, May (2005). 

Cooper, R.L. and A.J. Lindsey 3,4-Benzpyrene and other polycyclic hydrocarbons in cigarette smoke Brit. J. Cancer 9 (1955) 304-309. 

Benestad Genotoxicity and polycyclic hydrocarbon analysis of environmental tobacco smoke samples from restaurants Mutagenesis 1 (1986) 287-292. 1860b. 

Lyons, M.J. Comparison of aromatic polycyclic hydrocarbons from gasoline engine and diesel engine exhausts, general atmospheric dust, and cigarette smoke condensate in Symposium Analysis of carcinogenic... 

Pyriki, C. The appearance of polycyclic hydrocarbons in cigarette smoke CORESTAInf. Bull. 1960(1) 11-13. 

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