CHEMICAL STUDIES ON TOBACCO-SMOKE .30. CHRYSENE AND METHYLCHRYSENES - PRESENCE IN TOBACCO-SMOKE AND CARCINOGENICITY
CHEMICAL STUDIES ON TOBACCO-SMOKE .30. CHRYSENE AND METHYLCHRYSENES - PRESENCE IN TOBACCO-SMOKE AND CARCINOGENICITY
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DOI：
10.1093/jnci/53.4.1121
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发表时间：
1974-01-01
影响因子：
10.3
通讯作者：
HOFFMANN, D
中科院分区：
文献类型：
--
作者：
HECHT, SS;BONDINELL, WE;HOFFMANN, D
通过明确的途径合成的纯度大于99.9%的6种甲基金霉素异构体和金霉素在小鼠皮肤上进行了完全致癌性和肿瘤引发活性试验。5-与其他甲基汞和甲基汞的轻微致癌性相比，甲基汞显示出较高的致癌性（与苯并[a]芘相当）。5-Methylchyramine也是一个强大的肿瘤引发剂; 3-methylchyramine有中度的肿瘤引发活性。建立了一种从卷烟烟气中分离甲基屈烯的方法。它涉及溶剂分配的冷凝物，以获得富含多环芳烃的馏分，然后通过柱色谱，Diels-Alder反应，以消除苯并[a]蒽，高速液相色谱富集的甲基屈，气相色谱分离1-，2-，3-，和4-甲基屈，和，最后，纸色谱分离5-和6-甲基屈。在定量研究中，我们使用14 C-5，6-金作为内标。一支美国混合无过滤嘴香烟（85 mm）的烟雾含有7.2 ng 6-甲基金、6.1 ng 3-甲基金、1.2 ng 2-甲基金、3.0 ng 1-甲基金、0.6 ng 5-甲基金和36.5 ng金。热解实验表明，烟草甾醇可能不是烟气中甲基屈烯的主要来源。
The 6 methylchrysene isomers, synthesized in greater than 99.9% purity via unambiguous routes, and chrysene were tested for complete carcinogenicity and tumor-initiating activity on mouse skin. 5-Methylchrysene showed a high level of carcinogenicity (comparable to that of benzo[a]pyrene) in contrast to the marginal carcinogenicity of the other methylchrysenes and chrysene. 5-Methylchrysene was also a powerful tumor initiator; 3-methylchrysene had moderate tumor-initiating activity. A method was developed for the isolation of methylchrysenes from cigarette smoke. It involved solvent partitioning of the condensate to obtain the fraction rich in polynuclear aromatic hydrocarbons, followed by column chromatography, a Diels-Alder reaction to remove benz[a]anthracenes, high-speed liquid chromatography to enrich the methylchrysenes, gas chromatography to separate 1-, 2-, 3-, and 4-methylchrysenes, and, finally, paper chromatography to separate 5- and 6-methylchrysenes. For quantitative studies we used14C-5,6-chrysene as internal standard. The smoke of one U.S. blended nonfilter cigarette (85 mm) contained 7.2 ng of 6-methylchrysene, 6.1 ng of 3-methylchrysene, 1.2 ng of 2-methylchrysene, 3.0 ng of 1-methylchrysene, 0.6 ng of 5-methylchrysene, and 36.5 ng of chrysene. Pyrolysis experiments indicated that tobacco sterols were probably not the major source of methylchrysenes in smoke.