التفاصيل البيبلوغرافية
| العنوان: |
Identification by physical means of organic moieties of conjugates produced from carbaryl by tobacco cells in suspension culture. |
| المؤلفون: |
Locke, Raymond, Chen, Jo, Damico, Joseph, Dusold, Laurence, Sphon, James |
| المصدر: |
Archives of Environmental Contamination & Toxicology; Dec1976, Vol. 4 Issue 1, p60-100, 41p |
| مستخلص: |
Carbaryl (1-naphthyl methylcarbamate), labeled withC in the C-naphthyl, carbonyl, or N-methyl position, was introduced into the culture medium of tobacco cells in suspension culture. Following incubation, cells were homogenized in water, centrifuged, and supernatants hydrolyzed with Β-glucosidase or HCl. Organic moieties (moieties) were characterized by two-dimensional thin-layer chromatography (TLC), and many were subsequently identified by infrared and mass spectrometry. On the basis of the data obtained withC-naphthyl-labeled carbaryl, it appeared that 18.4% of the total characterized metabolites represented unconjugated N-CHOH- carbaryl [1-naphthyl N-(hydroxymethyl)carbamate], excreted by the cells into the culture medium. The metabolites found in the cells primarily consisted of conjugates of 1-naphthol (73.6% of the total characterized metabolites) and N-CHOH-carbaryl (2.5%). Conjugates of 7-hydroxycarbaryl (7-hydroxy-1-naphthyl methylcarbamate), 4-hydroxycarbaryl (4-hydroxy-1-naphthyl methylcarbamate), and 5-hydroxycarbaryl (5-hydroxy-1-naphthyl methylcarbamate) were also detected in small amounts. Of five unknownC-naphthyl-labeled carbaryl metabolites, three were tentatively characterized as: O-1-naphthylcholesterol (cholest-5-en-3Β-yl-1-naphthol; 3.0%); an unconjugated hydroxylated 1,4-dihydro-1,4-epiperoxynaphthalene (1.4%); and an acidlabile, Β-glucosidase-resistant conjugate of a cis-dihydrodiol of 1-naphthol (0.3%; other than the trans-5,6-dihydrodiol). The cholesterol derivative may represent a new 'detoxification mechanism' in plants; the epiperoxide may help to elucidate plant oxidation mechanisms. A new TLC procedure was developed which successfully separated the acetate derivative of N-hydroxycarbaryl (1-naphthyl N-hydroxy- N-methylcarbamate) from 12 other common moieties of carbaryl metabolites and their acetate derivatives. A new two-dimensional TLC system was developed for the separation of underivatized N-hydroxycarbaryl from 14 other moieties of carbaryl metabolites; two additional two-dimensional TLC systems were utilized for moiety separations. With these TLC procedures, no conjugated or unconjugated N-hydroxycarbaryl could be detected in any tobacco cell culture fraction after incubation of cells in medium containing radiolabeled carbaryl. AuthenticC-naphthyllabeled N-CHOH-carbaryl was shown to be converted to desmethylcarbaryl (1-naphthylcarbamate) (97%) and 1-naphthol (3%) by 0.1N HCl hydrolysis. [ABSTRACT FROM AUTHOR] |
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| قاعدة البيانات: |
Complementary Index |