Hepatic metabolism of diallyl disulphide in rat and man

References

• AMAGASE, H., PETESCH, B. L., MATSUURA, H., KASUGA, S. and ITAKURA, Y., 2001, Intake of garlic and its bioactive components. Journal of Nutrition, 131, 955S–962S.
   Google Scholar
• BELANGER, P. M. and ATITSE-GBEASSOR, A., 1982, Inhibitory effect of tranylcypromine on hepatic drug metabolism in the rat. Biochemical Pharmacology, 31, 2679–2683.
   Google Scholar
• BLOCK, E., 1992, The organosulfur chemistry of the genus Allium — implications for the organic chemistry of sulfur. Angezvandte Chemie, 31, 1135–1178.
   Web of Science ®Google Scholar
• BOURRIE, M., MEUNIER, V., BERGER, Y. and FABRE, G., 1996, Cytochrome P450 isoform inhibitors as a tool for the investigation of metabolic reactions catalyzed by human liver microsomes. Journal of Pharmacology and Experimental Therapeutics, 277, 321–332.
   PubMed Web of Science ®Google Scholar
• BRADFORD, M. M., 1976, A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein—dye binding. Analytical Biochemistry, 72, 248–254.
   PubMed Web of Science ®Google Scholar
• CAI, X. J., BLOCK, E., UDEN, P. C., QUIMBY, B. D. and SULLIVAN, J. J., 1995, Allium chemistry: identification of natural abundance organoselenium compounds in human breath after ingestion of garlic using gas chromatography with atomic emission detection. Journal of Agricultural and Food Chemistry, 43, 1751–1753.
   Google Scholar
• DAMANI, L. A., 1987, Metabolism of sulphur-containing drugs. In D. J. Benford, J. W. Bridges and G. G. Gibson (eds), Drug Metabolism from Molecules to Man (London: Taylor & Francis), pp. 581–603.
   Google Scholar
• EDWARDS, A. M., GLISTAK, M. L., LUCAS, C. M. and WILSON, P. A., 1984, 7-Ethoxycoumarin deethylase activity as a convenient measure of liver drug metabolizing enzymes: regulation in cultured rat hepatocytes. Biochemical Pharmacology, 33, 1537–1546.
   PubMed Web of Science ®Google Scholar
• EGEN-SCHWIND, C., ECKARD, R. and KEMPER, F. H., 1992, Metabolism of garlic constituents in the isolated perfused rat liver. Planta Medica, 58, 301–305.
   PubMed Web of Science ®Google Scholar
• FURNISS, B. S., HANNAFORD, A. J., SMITH, P. W. G. and TATcHELL, A. R., 1989, Vogel's Text Book of Practical Organic Chemistry, 5th edn (Chichester: Wiley).
   Google Scholar
• GARDNER, I., WAKAZONO, H., BERGIN, P., DE WAZIERS, I., BEAUNE, P., KENNA, J. G. and CALDWELL, J., 1997, Cytochrome P450 mediated bioactivation of methyleugenol to l'-hydroxymethyleugenol in Fischer 344 rat and human liver microsomes. Carcinogenesis, 18, 1775–1783.
   PubMed Web of Science ®Google Scholar
• GERMAIN, E., AUGER, J., GINIES, C., SIESS, M.-H. and TEYSSIER, C., 2002, In vivo metabolism of diallyl disulphide in the rat: identification of two new metabolites. Xenobiotica, 32, 1127–1138.
   Google Scholar
• HABER, D., SIESS, M. H., DE WAZIERS, I., BEAUNE, P. and SUSCHETET, M., 1994, Modification of hepatic drug-metabolizing enzymes in rat fed naturally occurring allyl sulphides. Xenobiotica, 24, 169–182.
   PubMed Web of Science ®Google Scholar
• KITCHELL, B. B., RAUCKMAN, E. J. and ROSEN, G. M., 1978, The effect of temperature on mixed function amine oxidase intrinsic fluorescence and oxidative activity. Molecular Pharmacology, 14, 1092–1098.
   PubMed Web of Science ®Google Scholar
• LAAKSO, I., SEPPANEN-LAAKSO, T., HILTUNEN, R., MULLER, B., JANSEN, H. and KNOBLOCH, K., 1989, Volatile garlic odor components: gas phases and adsorbed exhaled air analysed by headspace gas chromatography-mass spectrometry. Planta Medica, 55, 257–261.
   Google Scholar
• LATTARD, V., LACHUER, J., BURONFOSSE, T., OARNIER, F. and BENOIT, E., 2002, Physiological factors affecting the expression of FM01 and FM03 in the rat liver and kidney. Biochemical Pharmacology, 63, 1453–1464.
   PubMed Web of Science ®Google Scholar
• LAWSON, L. D. and WANG, Z. J., 1993, Pre-hepatic fate of the organosulfur compounds derived from garlic (Allium sativum). Planta Medica, 59, A688—A689.
   Google Scholar
• LE BON, A. M. and SIESS, M. H., 2000, Organosulphur compounds from Allium and the chemoprevention of cancer. Drug Metabolism and Drug Interactions, 17, 51–79.
   PubMedGoogle Scholar
• MILNER, J. A., 2001, A historical perspective on garlic and cancer. Journal of Nutrition, 131, 1027S–1031S.
   Google Scholar
• MINAMI, T., BOKU, T., INADA, K., MORITA, M. and OKAZAKI, Y., 1989, Odor components of human breath after the ingestion of grated raw garlic. Journal of Food Science, 54, 763–765.
   Web of Science ®Google Scholar
• MIRON, T., RABINKOV, A., MIRELMAN, D., WILCHEK, M. and WEINER, L., 2000, The mode of action of allicin: its ready permeability through phospholipid membranes may contribute to its biological activity. Biochimica et Biophysica Acta, 1463, 20–30.
   PubMed Web of Science ®Google Scholar
• NNANE, I. P. and DAMANI, L. A., 1999, Metabolism of ethyl methyl sulphide and sulphoxide in rat microsomal fractions. Xenobiotica, 29, 1101–1113.
   PubMed Web of Science ®Google Scholar
• NNANE, I. P. and DAMANI, L. A., 2002, HPLC analysis of 4-chlorophenyl methyl sulphide and diphenyl sulphide and their corresponding sulphoxides and sulphones in rat liver macrosomes. Journal of Pharmaceutical and Biomedical Analysis, 27, 315–325.
   PubMed Web of Science ®Google Scholar
• OMURA, T. and SATO, R., 1964, The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. Journal of Biological Chemistry, 269, 2370–2378.
   Google Scholar
• PHELPS, S. and HARRIS, W. S., 1993, Garlic supplementation and lipoprotein oxidation susceptibility. _Lipids, 28, 475–477.
   PubMed Web of Science ®Google Scholar
• PRASAD, K., LAXDAL, V. A., Yu, M. and RANEY, B. L., 1996, Evaluation of hydroxyl radical-scavenging property of garlic. Molecular and Cellular Biochemistry, 154, 55–63.
   PubMed Web of Science ®Google Scholar
• PUSHPENDRAN, C. K., DEVASAGAYAM, T. P., CHINTALWAR, G. J., BANERJI, A. and EAPEN, J., 1980, The metabolic fate of [355]-diallyl disulphide in mice. Experientia, 36, 1000–1001.
   PubMedGoogle Scholar
• RABINKOV, A., MIRON, T., MIRELMAN, D., WILCHEK, M., OLOZMAN, S., YAVIN, E. and WEINER, L., 2000, S-allylmercaptoglutathione: the reaction product of allicin with glutathione possesses
   Google Scholar
• SH-modifying and antioxidant properties. Biochimica et Biophysica Acta, 1499, 144–153.
   Google Scholar
• REUTER, H. D., 1995, Allium sativum and Allium ursinum: Part 2. Pharmacology and medicinal application. Phytomedicine, 2, 73–91.
   PubMed Web of Science ®Google Scholar
• RIVLIN, S., 2001, Historical perspective on the use of garlic. Journal of Nutrition, 131, 951S-954S. SHEEN, L. Y., Wu, C. C., LH, C. K. and TSAI, S. J., 1999, Metabolites of diallyl disulfide and diallyl sulfide in primary rat hepatocytes. Food and Chemical Toxicology, 37, 1139–1146.
   Web of Science ®Google Scholar
• SHIMADA, T., YAMAZAKI, H., MIMURA, M., INUI, Y. and OUENGERICH, F. P., 1994, Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. Journal of Pharmacology and Experimental Therapeutics. 270, 414–23.
   PubMed Web of Science ®Google Scholar
• SHu, L. and HOLLENBERG, P. F., 1997, Alkylation of cellular macromolecules and target specificity of carcinogenic nitrosodialkylamines: metabolic activation by cytochromes P450 2B1 and 2E1. Carcinogenesis, 18, 801–810.
   PubMed Web of Science ®Google Scholar
• TANAKA, E., 2001, Chlorzoxazone: a probe drug the metabolism of which can be used to monitor one-point blood sampling in the carbon tetrachloride-intoxicated rat. Human Experimental Toxicology, 20, 381–385.
   PubMed Web of Science ®Google Scholar
• TAUCHER, J., HANSEL, A., JORDAN, A. and LINDINGER, W., 1996, Analysis of compounds in human breath after ingestion of garlic using proton-transfer-reaction mass spectrometry. Journal of Agricultural and Food Chemistry, 44, 3778–3782.
   Web of Science ®Google Scholar
• TEYSSIER, C. and SIESS, M. H., 2000, Metabolism of dipropyl disulfide by rat liver phase I and II enzymes and by isolated perfused rat liver. Drug Metabolism and Disposition, 28, 648–654.
   PubMed Web of Science ®Google Scholar
• WAXMAN, D. J., DANNAN, G. A. and OUENGERICH, F. P., 1985, Regulation of rat hepatic cytochrome P-450: age-dependent expression, hormonal imprinting, and xenobiotic inducibility of sex-specific isoenzymes. Biochemistry, 24, 4409–4417.
   PubMed Web of Science ®Google Scholar
• YEUNG, C. K., LANG, D. H., THUMMEL, K. E. and RETTIE, A. E., 2000, Immunoquantitation of FM01 in human liver, kidney, and intestine. Drug Metabolism and Disposition, 28, 1107–1111.
   PubMed Web of Science ®Google Scholar