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Xenobiotica
the fate of foreign compounds in biological systems
Volume 22, 1992 - Issue 11
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Original Article

Microsomal formation of a pyrrolic alcohol glutathione conjugate of the pyrrolizidine alkaloid senecionine

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Pages 1321-1327 | Received 04 Dec 1991, Accepted 20 Apr 1992, Published online: 23 Apr 2010

References

  • Allen J. R., Hsu I. C., Carstens L. A. Dehydroretronecine-induced rhabdomyosarcomas in rats. Cancer Research 1975; 35: 997–1002
  • Buhler D. R., Kedzierski B. Biological reactive intermediates of pyrrolizidine alkaloids. Biological Reactive Intermediates, J. J. Kocsis, D. J. Jollow, C. M. Witmer, J. O. Nelson, R. Snyder. Plenum, New York 1986; vol. III: 611–620
  • Culvenor C. C. J., Edgar J. A., Smith L. W., Tweeddale H. J. Dihydropyrrolizines III. Preparation and reactions of derivatives related to pyrrolizidine alkaloids. Australian Journal of Chemistry 1970; 23: 1853–1867
  • Hirono I. Natural carcinogenic products of plant origin. CRC Critical Reviews in Toxicology 1981; 8: 235–266
  • Hoskins W. M., Crout D. H. G. Pyrrolizidine alkaloid analogues. Preparation of semisynthetic esters of retronecine. Journal of the Chemical Society Perkin Transactions I 1977; 538–544
  • Hsu I. C., Robertson K. A., Shumaker R. C., Allen J. R. Binding of tritiated dehydroretronecine to macromolecules. Research Communications in Chemical Pathology and Pharmacology 1975; 11: 99–106
  • Hsu I. C., Robertson K. A., Allen J. R. Tissue distribution, binding properties, and lesions produced by dehydroretronecine in the nonhuman primate. Chemico-Biological Interactions 1976; 12: 19–28
  • Huxtable R. J. Herbal teas and toxins: novel aspects of pyrrolizidine poisoning in the United States. Perspectives in Biology and Medicine 1980; 24: 1–14
  • Huxtable R. J., Bowers R., Mattocks A. R., Michnicka M. Sulfur conjugates as putative pneumotoxic metabolites of the pyrrolizidine alkaloid, monocrotaline. Biological Reactive Intermediates, vol. IV: Molecular and Cellular Effects and their impact on Human Health, C. M. Witmer, R. R. Snyder, D. J. Jollow, G. F. Kalf, J. J. Kocsis, I. G. Sipes. Plenum, New York 1990; 605–611
  • Jago M. V., Edgar J. A., Smith L. W., Culvenor C. C. J. Metabolic conversion of heliotridine-based pyrrolizidine alkaloids to dehydroheliotridine. Molecular Pharmacology 1970; 6: 402–406
  • Karchesy J. J., Arbogast B., Deinzer M. L. Kinetics of alkylation reactions of pyrrolizidine alkaloid pyrroles. Journal of Organic Chemistry 1987; 52: 3867–3872
  • Kedzierski B., Buhler D. R. Method for determination of pyrrolizidine alkaloids and their pyrrolizidine alkaloids. Toxicology Letters 1986; 25: 115–119
  • Kedzierski B., Buhler D. R. Method for determination of pyrrolizidine alkaloids and their metabolites by high-performance liquid chromatography. Analytical Biochemistry 1986; 152: 59–65
  • Lafranconi W. M., Ohkuma S., Huxtable R. J. Biliary excretion of novel pneumotoxic metabolites of the pyrrolizidine alkaloid, monocrotaline. Toxicon 1985; 23: 983–992
  • Lame M. W., Morin D., Jones A. D., Segall H. J., Wilson D. W. Isolation and identification of a pyrrolic glutathione conjugate metabolite of the pyrrolizidine alkaloid monocrotaline. Toxicology Letters 1990; 51: 321–329
  • Lowry O. H., Rosebrough N. J., Farr A. L., Randall R. J. Protein measurement with the Folin phenol reagent. Journal of Biological Chemistry 1951; 193: 265–275
  • Mattocks A. R. Chemistry and Toxicology of Pyrrolizidine Alkaloids. Academic Press, New York 1986
  • Mattocks A. R., Bird I. Pyrrolic and N-oxide metabolites formed from pyrrolizidine alkaloids by hepatic microsomes in vitro: Relevance to in vivo hepatotoxicity. Chemico-Biological Interactions 1983; 43: 209–222
  • Mattocks A. R., Jukes R. Recovery of the pyrrolic nucleus of pyrrolizidine alkaloid metabolites from sulphur conjugates in tissues and body fluids. Chemico-Biological Interactions 1990a; 75: 225–239
  • Mattocks A. R., Jukes R. Trapping and measurement of short-lived alkylating agents in a recirculating flow system. Chemico-Biological Interactions 1990b; 76: 19–30
  • Mattocks A. R., White I. N. H. Conversion of pyrrolizidine alkaloids to N-oxides and to dihydropyrrolizidine derivatives by rat-liver microsomes in vitro. Chemico-Biological Interactions 1971; 3: 383–391
  • Mattocks A. R., Legg R. J., Jukes R. Trapping of short-lived electrophilic metabolites of pyrrolizidine alkaloids escaping from perfused rat liver. Toxicology Letters 1990; 54: 93–99
  • Mattocks A. R., Croswell S., Jukes R., Huxtable R. J. Identity of a biliary metabolite formed from monocrotaline in isolated perfused rat liver. Toxicon 1991; 29: 409–415
  • McLean E. K. The toxic actions of pyrrolizidine (senecio) alkaloids. Pharmacological Reviews 1970; 22: 429–483
  • Niwa H., Ogawa T., Okamoto O., Yamada K. Alkylation of nucleosides by dehydromono-crotaline, the putative toxic metabolite of the carcinogenic pyrrolizidine alkaloid monocrotaline. Tetrahedron Letters 1991; 32: 927–930
  • Omura T., Sato R. The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. Journal of Biological Chemistry 1964; 239: 2370–2378
  • Reed R. L., Buhler D. R. The synthesis of 3H-putrescine and subsequent biosynthesis of 3H-jacobine, a pyrrolizidine alkaloid from Senecio jacobaea. Journal of Labelled Compounds and Radiopharmaceuticals 1988; 25: 1041–1048
  • Reed R. L., Ahern K. G., Pearson G. D., Buhler D. R. Crosslinking of DNA by dehydroretronecine, a metabolite of pyrrolizidine alkaloids. Corcinogenesis 1988; 9: 1355–1361
  • Robertson K. A. Alkylation of N2 in deoxyguanosine by dehydroretronecine, a carcinogenic metabolite of the pyrrolizidine alkaloid monocrotaline. Cancer Research 1982; 42: 8–14
  • Robertson K. A., Seymour J. L., Hsia M. T., Allen J. R. Covalent interaction of dehydroretronecine, a carcinogenic metabolite of the pyrrolizidine alkaloid monocrotaline, with cysteine and glutathione. Cancer Research 1977; 37: 3141–3144
  • Vamvakas S., Anders M. W. Formation of reactive intermediates by phase II enzymes: glutathione-dependent bioactivation reactions. Biological Reactive Intermediates, vol. IV: Molecular and Cellular Effects and their Impact on Human Health, C. M. Witmer, R. R. Snyder, D. J. Jollow, G. F. Kalf, J. J. Kocsis, I. G. Sipes. Plenum, New York, 13–24, White I. N. H. Mattocks A. R. 1971, Factors affecting the conversion of pyrrolizidine alkaloids to N-oxides and to pyrrolic derivatives in vitro. Xenobiotica 1991 1 503–505
  • White I. N. H., Mattocks A. R. Reaction of dihydropyrrolidines with deoxyribonucleic acids in vitro. Biochemical Journal 1972; 128: 291–297
  • Wickramanayake P. P., Arbogast B. L., Buhler D. R., Deinzer M. L., Burlingame A. L. Alkylation of nucleosides and nucleotides by dehydroretronecine; characterization of covalent adducts by liquid secondary ion mass spectrometry. Journal of the American Chemical Society 1985; 107: 2485–2488
  • Williams D. E., Reed R. L., Kedzierski B., Dannan G. A., Guengerich F. P., Buhler D. R. Bioactivation and detoxication of the pyrrolizidine alkaloid senecionine by cytochrome P-450 enzymes in rat liver. Drug Metabolism and Disposition 1989; 17: 387–392

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