S-adenosylmethionine synthesis: Molecular mechanisms and clinical implications

Pharmacology and Therapeutics

Volumn 73, Issue 3, 1997, Pages 265-280

  Mato, José M ^a   Alvarez, Luis ^a   Ortiz, Pablo ^a   Pajares, María A ^a  

^a INSTITUTO DE INVESTIGACIONES BIOMÉDICAS ALBERTO SOLS   (Spain)

Author keywords

glutathione; liver disease; methionine adenosyltransferase; oxidative stress; S adenosylhomocysteine; S adenosylmethionine

Indexed keywords

GLUTATHIONE; METHIONINE ADENOSYLTRANSFERASE; S ADENOSYLHOMOCYSTEINE; S ADENOSYLMETHIONINE;

ARTICLE; ENZYME DEFICIENCY; GENE EXPRESSION; GENETIC DISORDER; LIVER CIRRHOSIS; LIVER DISEASE; METHYLATION; MOLECULAR CLONING; OXIDATIVE STRESS; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN SYNTHESIS;

EID: 0030920140     PISSN: 01637258     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0163-7258(96)00197-0     Document Type: Review

References (172)

1. Alvarez, L., Asuncion, M., Corrales, F., Pajares, M. A. and Mato, J. M. (1991) Analysis of the 5′ non-coding region of rat liver S-adenosylmethionine synthetase mRNA and comparison of the Mr deduced from the cDNA sequence and the purified enzyme. FEBS Lett. 290: 142-146.
2. Alvarez, L., Corrales, F., Martin-Duce, A. and Mato, J. M. (1993) Characterization of a full-length cDNA encoding human liver S-adenosylmethionine synthetase. Tissue-specific gene expression and mRNA levels in hepatopathies. Biochem. J. 293: 481-486.
3. Alvarez, L., Mingorance, J., Pajares, M. A. and Mato, J. M. (1994) Expression of rat liver S-adenosylmethionine synthetase in Escherichia coli results in two active oligomeric forms. Biochem. J. 301: 557-561.
4. Avila, M., Mingorance, J., Martínez-Chantar, M. L., Casado, M., Martín-Sanz, P., Boscá, L. and Mato, J. M. (1996) Regulation of rat liver S-adenosylmethionine synthetase during septic shock: role of nitric oxide. Hepatology, in press.
5. Barak, A. J., Beckenhauer, H. C., Tuma, D. J. and Badakash, S. (1987) Effects of prolonged ethanol feeding on methionine metabolism in rat liver. Biochem. Cell. Biol. 63: 230-233.
6. Belli, D. C., Fournier, L. A., Lepage, G., Yousef, I. and Roy, C. C. (1994) S-adenosylmethionine prevents total parenteral nutrition-induced cholestasis in the rat. J. Hepatol. 21: 18-23.
7. Berger, R. (1985) Biochemical aspects of type I hereditary tyrosinemia. In: Inherited Diseases of Amino Acid Metabolism, pp. 192-197, Bickel, H. and Wechtel, U. (eds.) Georg Theme/ Verlar Thieme, Stuttgart.
8. Berger, R., van Faassen, H. and Smith, G. P. (1983) Biochemical studies on the enzymatic deficiencies in hereditary tyrosinemia. Clin. Chim. Acta. 134: 129-141.
9. Bergmann, S., Shatrov, V., Ratter, F., Schiemann, S., Schulze-Osthoff, K. and Lehmann, V. (1994) Adenosine and homocysteine together enhance TNF-mediated cytotoxicity but do not alter activation of nuclear factor kB in L929 cells. J. Immunol. 153: 1736-1743.
10. Boerjan, W., Bauw, G., Van Montagu, M. and Inze, D. (1994) Distinct phenotypes generated by overexpression and suppression of S-adenosyl-L-methionine synthetase reveal developmental patterns of gene silencing in tobacco. Plant Cell 6: 1401-1414.
11. Bray, G. P., Tredger, M. and Williams, R. (1992) S-Adenosylmethionine protects against acetaminophen hepatotoxicity in two mouse models. Hepatology 15: 297-301.
12. Buhl, R., Jaffe, H. A. and Holroyd, K. J. (1989) Systemic glutathione deficiency in symptom-free HIV-seropositive individuals. Lancet ii: 1294-1298.
13. Butler, T. C. (1961) Reduction of carbon tetrachloride in vivo and reduction of carbon tetrachloride and chloroform in vitro by tissues and tissue constituents. J. Pharmacol. Exp. Ther. 134: 311-319.
14. Cabrero, C. and Alemany, S. (1988) Conversion of rat liver S-adenosyl-L-methionine synthetase from high-Mr form to low-Mr form by LiBr. Biochim. Biophys. Acta 952: 277-281.
15. Cabrero, C., Puerta, J. and Alemany, S. (1987) Purification and comparison of two forms of S-adenosyl-L-methionine synthetase from rat liver. Eur. J. Biochem. 170: 299-304.
16. Cabrero, C., Martin-Duce, A., Ortiz, P., Alemany, S. and Mato, J. M. (1988) Specific loss of the high-molecular weight form of S-adenosyl-L-methionine synthetase in human liver cirrhosis. Hepatology 8: 1530-1534.
17. Cantoni, G. L. (1975) Biochemical methylations: selected aspects. Annu. Rev. Biochem. 44: 435-441.
18. Cantoni, G. L. and Chiang, P. K. (1980) The role of S-adenosylhomocysteine and S-adenosylhomocysteine hydrolase in the control of biological methylations. In: Natural Sulfur Compounds: Novel Biochemical and Structural Aspects, pp. 67-80, Cavallini, D., Gaull, G. E. and Zappia, V. (eds.) Plenum Press, New York.
19. Casini, A., Banchetti, E. and Milani, S. (1989) S-Adenosylmethionine inhibits collagen synthesis by human fibroblasts in vitro. Methods Fund. Exp. Clin. Pharmacol. 11: 331-334.
20. Castagna, A., Le Grazie, C., Accordini, A., Giulidori, P., Cavalli, G., Bottiglieri, T. and Lazzarin, A. (1995) Cerebrospinal fluid S-adenosylmethionine (SAMe) and glutathione concentrations in HIV infection: effect of parenteral treatment with SAMe. Neurology 35: 1678-1683.
21. Chanarin, I., Deacon, R., Lumb, M., Muir, M. and Perry, J. (1985) Cobalamin-folate interrelations: a critical review. Blood 66: 479-489.
22. Chase, H. P., Volpe, J. J. and Laster, L. (1968) Transsulfuration in mammals: fetal and early development of methionine-activating enzyme and its relation to hormonal influences. J. Clin. Invest. 47: 2099-2108.
23. Chawla, R. K. and Jones, D. P. (1994) Abnormal metabolism of S-adenosyl-L-methionine in hypoxic rat liver. Similarities to its abnormal metabolism in alcoholic cirrhosis. Biochim. Biophys. Acta. 1199: 45-51.
24. Chawla, R. K., Lewis, F. W., Kutner, M. H., Mate, D. M., Roy, R. G. B. and Rudman, D. (1984) Plasma cysteine, cystine and glutathione in cirrhosis. Gastroenterology 87: 770-776.
25. Chiang, P. K. and Cantoni, G. L. (1977) Activation of methionine for transmethylation: purification of the S-adenosylmethionine synthetase of baker's yeast and its separation into forms. J. Biol. Chem. 252: 4506-4513.
26. Chiang, P. K., Richard, M. H. and Cantoni, G. L. (1977) S-Adenosyl-L-homocysteine hydrolase: analogues of S-adenosyl-L-homocysteine as potential inhibitors. Mol. Pharmacol. 13: 939-947.
27. Clarke, R., Daly, L., Killian, R., Naughten, E., Gahalane, S., Fowler, B. and Graham, I. (1991) Hyperhomocysteinemia: an independent risk factor for vascular disease. N. Engl. J. Med. 324: 1149-1155.
28. Cook, R. J. and Wagner, C. (1984) Glycine N-methyltransferase is a folate binding protein. Proc. Natl. Acad. Sci. USA 81: 3631-3634.
29. Cooper, A. J. L. (1989) Methionine transamination in vivo. Biochem. J. 262: 689-691.
30. Corcoran, G. B. and Wong, B. K. (1986) Role of glutathione in prevention of acetaminophen induced hepatotoxicity by N-acetyl-L-cysteine in vivo: studies with N-acetyl-L-cysteine. J. Pharmacol. Exp. Ther. 238: 54-61.
31. Corrales, F., Cabrero, C., Pajares, M. A., Ortíz, P., Martín-Duce, A. and Mato, J. M. (1990) Inactivation and dissociation of S-adenosylmethionine synthetase by modification of sulfhydryl groups and its possible occurrence in cirrhosis. Hepatology 11: 216-222.
32. Corrales, F., Ochoa, P., Rivas, C., Martín-Lomas, M., Mato, J. M. and Pajares, M. A. (1991) Inhibition of glutathione synthesis in the liver leads to S-adenosyl-L-methionine synthetase reduction, Hepatology 14: 528-533.
33. 4-induced S-adenosylmethionine synthetase inactivation and attenuates liver injury. Hepatology 16: 1022-1027.
34. De Clercq, E. (1987) S-Adenosylhomocysteine hydrolase inhibitors as broad spectrum antiviral agents. Biochem. Pharmacol. 36: 2567-2575.
35. Deigner, H. P., Mato, J. M. and Pajares, M. A. (1995) Study of the rat liver S-adenosylmethionine synthetase active site with 8-azido ATP. Biochem. J. 308: 565-571.
36. De la Rosa, J., Geller, A. M., LeGros, H. L. and Kotb, M. (1992a) Induction of interleukin-2 production but not methionine adenosyltransferase activity or S-adenosylmethionine turnover in Jurkat T-cells. Cancer Res. 52: 3361-3366.
37. De la Rosa, J., LeGros, H. L., Geller, A. M. and Kotb, M. (1992b) Changes in the relative amount of subunits of methionine adenosyltransferase in human lymphocytes upon stimulation with a polyclonal T cell mitogen. J. Biol. Chem. 267: 10699-10704.
38. De la Rosa, J., Ostrowski, J., Hryniewicz, M. M., Kredich, N. M., Kotb, M., LeGros, H. L., Valentine, M. and Geller, A. M. (1995) Chromosomal localization and catalytic properties of the recombinant alpha subunit of human lymphocyte methionine adenosyltransferase. J. Biol. Chem. 270: 21860-21868.
39. Diamond, M. I., Miner, J. N., Yoshinaga, S. K. and Yamamoto, K. R. (1990) Transcription factor interactions: selectors of positive or negative regulation from a single DNA element. Science 249: 1266-1272.
40. Di Monte, D. A., Chan, P. and Sandy, M. S. (1992) Glutathione in Parkinson's disease: a link between oxidative stress and mitochondrial damage? Ann. Neural. 32: S111-S115.
41. Di Padova, C., Tritapepe, R., Rovagnati, P., Pozzoli, M. and Stramentinoli, G. (1984) Decreased blood levels of ethanol and acetyldehyde by S-adenosyl-L-methionine in humans. Arch. Toxicol. 7: 240-242.
42. Di Padova, C., Di Padova, F., Tritapepe, R. and Stramentinoli, G. (1985) S-Adenosyl-L-methionine protection against alfa-naftyl-isothiocyanate-induced cholestasis in the rat. Toxicol. Lett. 29: 131-136.
43. Dizik, M, Christman, J. K. and Wainfan, E. (1991) Alterations in expression and methylation of specific genes in liver of rats fed a cancer promoting methyl-deficient diet. Carcinogenesis 12: 1307-1312.
44. Dunne, J. B., Davenport, M., Williams, R. and Tredger, J. M. (1994) Evidence that S-adenosylmethionine and N-acetylcysteine reduce injury from sequential cold and warm ischaemia in the isolated perfused rat liver. Transplantation 57: 1161-1168.
45. Eck, H. P., Gmunder, H., Hartmann, M., Petzoldt, D., Daniel, V. and Droge, W. (1989) Low concentrations of acid-soluble thiol (cysteine) in the blood and plasma of HIV-1 infected patients. Biol. Chem. Hoppe Seyler 370: 101-108.
46. Feo, F., Pascale, R., Garcea, R., Daino, L. and Pirsi, L. (1986) Effect of the variations of S-adenosyl-L-methionine liver content on fat accumulation and ethanol metabolism in ethanol-intoxicated rats. Toxicol. Appl. Pharmacol. 83: 331-341.
47. Fernandez, E., Galan, A. I., Moran, D., Gonzalez-Buitrago, J. M., Muñoz, M. E. and Jimenez, R. (1995) Reversal of cyclosporine A-induced alterations in biliary secretion by S-adenosyl-L-methionine in rats. J. Pharmacol. Ther. 275: 114-119.
48. Finkelstein, J. D. (1967) Methionine metabolism in mammals: effect of age, diet, and hormones on three enzymes of the pathway in rat tissues. Arch. Biochem. Biophys. 122: 583-590.
49. Finkelstein, J. D. (1990) Methionine metabolism in mammals. J. Nutr. Biochem. 1: 228-236.
50. Finkelstein, J. D. and Martin, J. J. (1984a) Inactivation of betaine-homocysteine methyltransferase by S-adenosylmethionine and S-adenosylhomocysteme. Biochem. Biophys. Res. Commun. 118: 14-19.
51. Finkelstein, J. D. and Martin, J. J. (1984b) Methionine metabolism in mammals: distribution of homocysteine between competitive pathways. J. Biol. Chem. 259: 9508-9513.
52. Finkelstein, J. D., Kyle, W. E., Kartin, J. J. and Pick, A. M. (1975a) Activation of cystathionine synthase by S-adenosylmethionine and S-adenosylethionine. Biochem. Biophys. Res. Commun. 66: 81-87.
53. Finkelstein, J. D., Kyle, W. E. and Martin, J. J. (1975b) Abnormal methionine adenosyitransferase in hypermethioninemia. Biochem. Biophys. Res. Commun. 66: 1491-1497.
54. Fraser, C. M., Gocayne, J. D., White, O., Adams, M. D., Clayton, R. A., Fleischmann, R. D., Bult, C. J., Kerlavage, A. R., Sutton, G., Kelley, J. M., Fritchman, J. L., Weidman, J. F., Small, K. V., Sandusky, M., Fuhrmann, J., Nguyen, D., Utterback, T. R., Saudek, D. M., Phillips, C. A., Merrick, J. M., Tomb, J-F., Dougherty, B. A., Bott, K. F., Hu, P-C., Lucier, T. S., Peterson, S. N., Smith, H. O., Hutchison, C. A., III and Venter, J. C. (1995) The minimal gene complement of Mycoplasma genitalium. Science 270: 397-403.
55. Frezza, M., Tritapepe, R., Pozzato, G. and Di Padova, C. (1988) Prevention by S-adenosylmethionine of estrogen-induced hepato biliary toxicity in women. Am. J. Gastroenterol. 83: 1098-1102.
56. Frezza, M., Surrenti, C., Manzillo, G., Fiaccadori, F., Bortolini, M. and Di Padova, C. (1990) Oral S-adenosylmethionine in the symptomatic treatment of intrahepatic cholestasis: a double-blind, placebo controlled study. Gastroenterology 99: 211-215.
57. Gahl, W. A., Finkelstein, J. D., Mullen, K. D., Bernardini, I., Martin, J. J., Backlund, P., Ishak, K. G., Hoofnagle, J. H. and Mudd, S. H. (1987) Hepatic methionine adenosyltransferase deficiency in a 31-year-old man. Am. J. Hum. Genet. 40: 39-49.
58. Garcia-Ruiz, C., Morales, A., Colell, A., Ballesta, A., Rodes, J., Kaplowitz, N. and Fernandez-Checa, J. C. (1995) Feeding S-adenosyl-L-methionine attenuates both ethanol-induced depletion of mitochondrial glutathione and mitochondrial dysfunction in periportal and perivenous rat hepatocytes. Hepatology 21: 207-214.
59. Gassó, M., Rubio, M., Varela-Moreiras, G., Cabré, M., Caballería, J., Alonso, E., Deulofeu, R., Camps, J., Giménez, A., Pajares, M. A., Parés, A., Mato, J. M. and Rodés, J. (1996) Effects of S-adenosylmethionine on lipid peroxidation and liver fibrogenesis in carbon tetrachloride-induced cirrhosis. J. Hepatol, in press.
60. Gaull, G. E. and Tallan, T. H. (1974) Methionine adenosyltransferase deficiency: new enzymatic defect associated with hypermethioninemia. Science 189: 59-60.
61. Gaull, G. E, Tallan, H. H., Lonsdale, D., Pryrembel, H., Schaffner, F. and von Bassewitz, D. B. (1981) Hypermethioninemia associated with methionine adenosyltransferase deficiency: clinical, morphological and biochemical observations on four patients. J. Pediatr. 98: 734-741.
62. Gil, B., Casado, M., Pajares, M. A., Boscá, L., Mato, J. M., Martín-Sanz, P. and Alvarez, L. (1996) Differential expresion pattern of S-adenosylmethionine synthetase isoenzymes during rat liver development. Hepatology 24: 876-881.
63. Gil, B., Pajares, M. A., Mato, J. M. and Alvarez, L. (1997) Glucocorticoid regulation of hepatic S-adenosylmethionine synthetase gene expression. Endocrinology, in press.
64. Giudici, G. A., Le Grazie, C. and Di Paodva, C. (1992) The use of ademethionine (SAMe) in the treatment of cholestatic liver disorders. Metanalisis of clinical trials. In: Methionine Metabolism: Molecular Mechanism and Clinical Implications, pp. 67-79, Mato, J. M., Lieber, C., Kaplowitz, N. and Caballero, A. (eds.) CSIC Press, Madrid.
65. Hancock, R. L. (1966) S-Adenosylmethionine-synthesizing activity of normal and neoplasic mouse tissue. Cancer Res. 26: 2425-2430.
66. Herbst, R. S., Friedman, N., Darnell, J. E. and Babiss, L. E. (1989) Positive and negative regulatory elements in the mouse albumin enhancer. Proc. Natl. Acad. Sci. USA 86: 1553-1557.
67. Hirai, M., Iwamura, S., Varghese, G., Speisky, H. and Israel, Y. (1994) Reciprocal gamma-glutamyl transferase and cystathionase activity in guinea pig, rat and human liver. J. Hepatol. 21: 683-688.
68. Hoffman, J. L. (1983) Fractionation of methionine adenozyltransferase isozymes (rat liver). Meth. Enzymol. 94: 223-228.
69. Hoffman, J. L. and Sullivan, D. M. (1982) Differential properties and regulation of methionine adenosyltransferase isoforms from the rat. In: Biochemistry of S-Adenosylmethionine and Related Compounds, pp. 683-686, Usdin, E., Borchardt, R. I. and Creveling, C. R. (eds.) Pitman Press, Bath.
70. Horikawa, S. and Tsukada, K. (1991) Molecular cloning and nucleotide sequence of cDNA encoding the human liver S-adenosylmethionine synthetase. Biochem. Int. 25: 81-90.
71. Horikawa, S. and Tsukada, K. (1992) Molecular cloning and developmental expression of a human kidney S-adenosylmethionine synthetase. FEBS Lett. 312: 37-41.
72. Horikawa, S., Ishikawa, M., Ozasa, H. and Tsukada, K. (1989) Isolation of a cDNA encoding the rat liver S-adenosylmethionine synthetase. Eur. J. Biochem. 184: 497-501.
73. Horikawa, S., Sasuga, J., Shimizu, K., Ozasa, H. and Tsukada, K. (1990) Molecular cloning and nucleotide sequence of cDNA encoding the rat kidney S-adenosylmethionine synthetase. J. Biol. Chem. 265: 13683-13686.
74. Horikawa, S., Ozasa, H., Ota, K. and Tsukada, K. (1993) Immunohistochemistry analysis of rat S-adenosylmethionine synthetase isozymes in developmental liver. FEBS Lett. 330: 307-311.
75. Horowitz, J. H., Rypins, E. B., Henderson, J. M, Heymsfield, S. B., Moffitt, S. D., Hain, R. P. and Chawla, R. K. (1981) Evidence for impairment of transsulfuration pathway in cirrhosis. Gastroenterology 81: 668-675.
76. Imler, J. L, Lemaire, C, Wasylyk, C. and Wasylyk, B. (1987) Negative regulation contributes to tissue-specificity of the immunoglobulin heavy-chain enhancer. Mol. Cell. Biol. 7: 2558-2567.
77. Keating, J. N., Trimble, K. C., Mulcahy, F., Scott, J. M. and Weir, D. G. (1991) Evidence of brain methyltransferase inhibition and early involvement in HIV positive patients. Lancet 337: 935-939.
78. Kinsell, L. W., Harper, H. A., Marton, H. C., Michael, G. D. and Weiss, H. A. (1947) Rate of disappearance from plasma of intravenously administered methionine in patients with liver damage. Science 106: 589-590.
79. Kotb, M. and Geller, A. M. (1993) Methionine adenosyltransferase: structure and function. Pharmacol. Ther. 59: 125-143.
80. Kotb, M. and Kredich, N. M. (1985) S-Adenosylmethionine synthetase from human lymphocytes. Purification and characterization. J. Biol. Chem. 260: 3923-3930.
81. Kotb, M., Geller, A. M., Markham, G. D., Kredich, N. M., De la Rosa, J. and Beachey, E. H. (1990) Antigenic conservation of primary structural regions of S-adenosylmethionine synthetase. Biochim. Biophys. Acta 1040: 137-144.
82. Kunz, G. L., Hoffman, J. L., Chia, C. S. and Stremel, B. (1980) Separation of rat liver methionine adenosyltransferase isozymes by hydrophobic chromatography. Arch. Biochem. Biophys. 202: 565-572.
83. Kutzbach, C. and Stokstad, E. L. R. (1967) Feedback inhibition of methylene-tetrahydrofolate reductase in rat liver by S-adenosylmethionine. Biochim. Biophys. Acta 139: 217-220.
84. Kutzbach, C. and Stokstad, E. L. R. (1971) Mammalian methylentetrahydrofolate reductase: partial purification, properties and inhibition by S-adenosylmethionine. Biochim. Biophys. Acta 250: 459-477.
85. 4. Biochem. Pharmacol. 28: 2231-2235.
86. Liau, M. C., Lin, G. W. and Huribert, R. B. (1977) Partial purification and characterization of tumor and liver S-adenosylmethionine synthetases. Cancer Res. 37: 427-435.
87. Liau, M. C., Chang, C. F., Belanger, L. and Grenier, A. (1979) A correlation of isoenzyme patterns of S-adenosylmethionine synthetase with fetal stages and pathological states of the liver. Cancer Res. 39: 162-169.
88. Lieber, C. S. and Leo, M. A. (1992) Alcohol and the liver. In: Medical and Nutritional Complications of Alcoholism: Mechanisms and Management, Ch. 7, pp. 185-239, Lieber, C. S. (ed.) Plenum Press, New York.
89. Lieber, C. S., Jones, D. P. and De Carli, L. M. (1965) Effect of prolonged ethanol intake: production of fatty liver despite adequate diets. J. Clin. Invest. 44: 1009-1021.
90. Lieber, C. S., Casini, A., DeCarli, L. M., Kim, C., Lowe, N., Sasaki, R. and Leo, M. A. (1990) S-Adenosyl-L-methionine attenuates alcohol-induced liver injury in the baboon. Hepatology 11: 165-172.
91. Lieber, C. S., Robins, S. J. and Leo, M. A. (1994a) Hepatic phosphatidylethanolamine methyltransferase activity is decreased by ethanol and increased by phosphatidylcholine. Alcohol. Clin. Exp. Res. 18: 592-595.
92. Lieber, C. S., Robins, S. J., Li, J., DeCarli, L. M., Mak, K. M., Fasulo, J. M. and Leo, M. A. (1994b) Phosphatidylcholine protects against fibrosis and cirrhosis in the baboon. Gastroenterology 106: 152-159.
93. Liu, Y. H., Yang, N. Y. and Teng, C. T. (1993) COUP-TF acts as a competitive repressor for estrogen receptor-mediated activation of the mouse lactoferrin gene. Mol. Cell. Biol. 13: 1836-1846.
94. Lombardini, J. B., Chou, T. C. and Talalay, P. (1973) Regulatory properties of adenosine triphosphate-L-methionine S-adenosyltransferase of rat liver. Biochem. J. 135: 43-57.
95. Marchesini, G., Bugianesi, E., Bianchi, G., Fabbri, A., Marchi, E., Zoli, M. and Pisi, E. (1992) Defective methionine metabolism in cirrhosis: relation to severity of liver disease. Hepatology 16: 149-155.
96. Markham, G. D., DeParasis, J. and Gatmaitan, J. (1984) The sequence of met K, the structural gene for S-adenosylmethionine synthetase in Escherichia coli. J. Biol. Chem. 262: 5609-5615.
97. Martensson, J. and Meister, A. (1989) Mitochondrial damage in muscle occurs after marked depletion of glutathione and is prevented by giving glutathione monoester. Proc. Natl. Acad. Sci. USA 86: 471-475.
98. Martensson, J., Jain, A., Frayer, W. and Meister, A. (1989) Glutathione metabolism in the lung: inhibition of its synthesis leads to lamellar body and mitochondrial defects. Proc. Natl. Acad. Sci. USA 86: 5296-5300.
99. Martin-Duce, A., Ortiz, P., Cabrero, C. and Mato, J. M. (1988) S-Adensoyl-L-methionine synthetase and phospholipid methyltransferase are inhibited in human cirrhosis. Hepatology 8: 65-68.
100. Mato, J. M. and Alemany, S. (1983) What is the function of phospholipid methylation? Biochem. J. 213: 1-10.
101. Mato, J. M., Alvarez, L., Corrales, F. and Pajares, M. A. (1994) S-adenosylmethionine and the liver. In: The Liver Biology and Pathobiology, 3rd edn., pp. 461-470, Arias, I. M., Boyer, J. L., Fausto, N., Jakoby, W. B. and Schaachter, D. A. (eds.) Raven Press, New York.
102. Matsumoto, C., Suma, Y. and Tsukada, K. (1984) The alpha-form of S-adenosylmethionine synthetase isozymes from liver is principally functional. J. Biochem. 95: 1223-1226.
103. McCormick, D. B. and Munro, H. N. (1994) Liver in relation to water-soluble vitamins. In: The Liver: Biology and Pathobiology, Ch. 32, pp. 563-583, Arias, I. M., Boyer, J. L., Fausto, N., Jakoby, W. B., Schachter, D. and Shafritz, D. A. (eds.) Raven Press Ltd., New York.
104. Meister, A. and Anderson, M. E. (1983) Glutathione. Annu. Rev. Biochem. 52: 711-760.
105. Mesa, M. L., Carrizosa, R., Martínez-Honduvilla, C., Benito, M. and Fabregat, I. (1996) Changes in rat liver gene expression induced by thioacetamide: protective role of S-adenosyl-L-methionine by a glutathione-dependent mechanism. Hepatology 23: 600-606.
106. Mietus-Snyder, M., Sladek, F. M., Ginsburg, G. S., Kuo, C. F., Ledias, J. A. A., Darnell, J. E. and Karathanasis, S. K. (1992) Antagonism between apolipoprotein A1 regulatory protein, Ear 3/COUP-TF, and hepatocyte nuclear factor 4 modulates apolipoprotein CIII gene expression in liver and intestinal cells. Mol. Cell. Biol. 12: 1708-1718.
107. Miller, J. W., Nadeau, M. R., Smith, J., Smith, D. and Selhub, J. (1994) Folate-deficiency-induced homocysteinemia in rats: disruption of S-adenosylmethionine's co-ordinate regulation of homocysteine metabolism. Biochem. J. 298: 415-419.
108. Mingorance, J., Alvarez, L, Sanchez-Góngora, E., Mato, J. M. and Pajares, M. A. (1996) Site-directed mutagenesis of rat liver S-adenosylmethionine synthetase. Identification of a cysteine residue critical for the oligomeric state. Biochem. J. 315: 761-766.
109. Mitsui, K., Teraoka, H. and Tsukada, K. (1988) Complete purification and immunochemical analysis of S-adenosylmethionine synthetase from bovine brain. J. Biol. Chem. 263: 11211-11216.
110. Mudd, S. H. and Cantoni, G. L. (1958) Activation of methionine tor transmethylation. III. The methionine-activating enzyme of Baker's yeast. J. Biol. Chem. 231: 481-492.
111. Mudd, S. H. and Poole, J. R. (1975) Labile methyl balances for normal humans on various dietary regimens. Metabolism 24: 721-735.
112. Mudd, S. H., Ebert, M. H. and Scriver, C. R. (1980) Labile methyl group balances in the human: the role of sarcosine. Metabolism 29: 707-720.
113. Muglia, L. and Rothman-Denes, L. B. (1986) Cell type-specific negative regulatory element in the control region of the rat alpha-fetoprotein gene. Proc. Natl. Acad. Sci. USA 83: 7653-7657.
114. Newberne, P. M. and Rogers, A. E. (1986) Labile methyl groups and the promotion of cancer. Annu. Rev. Nutr. 6: 407-432.
115. Nir, U., Walker, M. D. and Rutter, W. J. (1986) Regulation of rat insulin gene expression: evidence for negative regulation in non pancreatic cells. Proc. Natl. Acad. Sci. USA 83: 3180-3184.
116. Okada, G., Watanabe, Y. and Tsukada, K. (1980) Changes in patterns of S-adenosylmethionine synthetases in fetal and postnatal rat liver. Cancer Res. 40: 2895-2897.
117. Okada, G., Teraoka, H. and Tsukada, K. (1981) Multiple species of mammalian S-adenosylmethionme synthetase. Partial purification and characterization. Biochemistry 20: 934-940.
118. Osada, J., Aylagas, J., Sanchez-Vegazo, I., Gea, T., Millan, I. and Palacios-Alaiz, E. (1986) Effect of S-adenosyl-L-methionine on thioacetamide-induced liver damage in rats. Toxicol. Lett. 32: 97-106.
119. Pajares, M. A., Corrales, F., Ochoa, P. and Mato, J. M. (1991) The role of cysteine 150 in the structure and activity of rat liver S-adenosyl-L-methionine synthetase. Biochem. J. 274: 225-229.
120. Pajares, M. A., Corrales, F., Durán, C., Mato, J. M. and Alvarez, L. (1992a) How is rat liver S-adenosylmethionine synthetase regulated? FEBS Lett. 309: 1-4.
121. Pajares, M. A., Durán, C., Corrales, F., Pliego, M. M. and Mato, J. M. (1992b) Modulation of rat liver S-adenosylmethionine synthetase activity by glutathione. J. Biol. Chem. 267: 17589-17605.
122. Pajares, M. A., Durán, C., Corrales, F. and Mato, J. M. (1994) Protein kinase C phosphorylation of rat liver S-adenosylmethionine synthetase: dissociation and production of an active monomer. Biochem. J. 303: 949-955.
123. Pajares, M. A., Alvarez, L., Gil-Perez, B., Martinez-Chantar, M. L., Mingorance, J., Sánchez-Góngora, E., Deigner, P., Avila, M. and Mato, J. M. (1996) S-Adenosylmethionine synthetase: a target enzyme to develop drugs against oxidative stress. In: Methionine Metabolism: Molecular Mechanism and Clinical Implications, Mato, J. M. and Caballero, A. (eds.) CSIC Press, Madrid, pp. 1-10.
124. Pan, F. and Tarver, H. (1967) Effects of diet and other factors on methionine adenosyltransferase levels in rat liver. J. Nutr. 92: 274-280.
125. Pan, F., Chang, G. G., Lee, S. C. and Tang, M. S. (1968a) Induction of methionine adenosyltransferase in rat liver by corticosteroids. Proc. Soc. Exp. Biol. Med. 128: 611-616.
126. Pan, F., Lee, S. C., Chang, G. G. and Sing-Pie, C. (1968b) Gonadal hormones in the regulation of methionine adenosyltransferase levels in rat liver. Proc. Soc. Exp. Biol. Med. 129: 161-165.
127. Paredes, S. R., Kozicki, P. A. and Batlle, A. M. (1985) S-Adenosyl-L-methionine a counter to lead intoxication? Comp. Biochem. Physiol. 82: 751-757.
128. Pascale, R., Daino, L., Garcea, R., Frassetto, S. and Ruggiu, M. E. (1989) Inhibition by ethanol of rat liver plasma membrane (Na+,K+) ATPase. Protective effect of S-adenosyl-L-methionine, L-methionine and N-acetylcysteine. Toxicol. Appl. Pharmacol. 97: 216-229.
129. Ponsoda, X., Jover, R., Gomez-Lechon, M. J., Fabra, R., Trullenque, R. and Castell, J. V. (1991) Intracellular glutathione in human hepatocytes incubated with S-adenosyl-L-methionine and GSH-depleting drugs. Toxicology 70: 293-302.
130. Razin, A. and Riggs, A. D. (1980) DNA methylation and gene function. Science 210: 604-609.
131. Reue, K., Leff, T. and Breslow, J. L. (1988) Human apolipoprotein CIII gene expression is regulated by positive and negative cisacting elements and tissue-specific protein factors. J. Biol. Chem. 263: 6857-6864.
132. Sakata, S. F., Shelly, L. L., Ruppert, S., Schutz, G. and Chou, J. Y. (1993) Cloning and expression of murine S-adenosylmethionine synthetase. J. Biol. Chem. 268: 13978-13986.
133. Sánchez-Góngora, E., Pastorino, J. G., Alvarez, L., Pajares, M. A., García, C., Viña, J., Mato, J. M. and Farber, J. L. (1996) Increased sensitivity to oxidative injury in CHO cells stably transfected with rat liver S-adenosylmethionine synthetase cDNA. Biochem. J., 319: 767-773.
134. Satischandran, C., Taylor, J. C. and Markham, G. D. (1990) Novel Escherichia coli K-12 mutants impaired in S-adenosylmethionine synthesis. J. Bacteriol. 172: 4489-4496.
135. Schuller, A., Solis-Herruzo, J. A., Moscat, J., Fernandez-Checa, J. C. and Municio, A. M. (1986) The fluidity of liver plasma membranes from patients with different types of liver injury. Hepatology 6: 714-717.
136. Scott, J. M., Dinn, J., Wilson, P. and Weir, D. G. (1981) Pathogenesis of subacute combined degeneration: a result of methyl group deficiency. Lancet ii: 334-337.
137. Selhub, J., Jacques, P. F., Bostom, A. G., D'Agostino, R. B., Wilson, P. W. F., Belanger, A. J., O'Learly, D. H., Wolf, P. A., Schaefer, E. J. and Rosenberg, I. H. (1995) Plasma homocysteine and extracranial carotid stenosis in the framingham heart study. N. Engl. J. Med. 332: 286-291.
138. Shou, L., Pan, F. and Chin, S. P. (1969) Pancreatic hormones and hepatic methionine adenosyltransferase in the rat. Proc. Soc. Exp. Biol. Med. 131: 1012-1018.
139. Sladek, F. M. and Darnell, J. E. (1992) Mechanisms of liver-specific gene expression. Curr. Opin. Genet. Dev. 2: 256-259.
140. Slater, T. F. (1984) Free-radical mechanisms in tissue injury. Biochem. J. 222: 1-15.
141. Staal, C. V., Hansen, T. N., Hanson, I. C. and Shearer, W. T. (1992) Glutathione deficiency and human immunodeficiency virus infection. Lancet 339: 909-912.
142. Stramentinoli, G., Gulano, M. and Ideo, G. (1978) Protective role of S-adenosyl-L-methionine on liver damage induced by D-galactosamine in rats. Biochem. Pharmacol. 27: 1431-1433.
143. Stramentinoli, G., Pezzoli,C. and Galli-Kienle,M. (1979) Protective role of S-adenosyl-L-methionine against acetaminophen induced mortality and hepatotoxicity in mice. Biochem. Pharmacol. 28: 3567-3571.
144. Stramentinoli, G., Di Padova, C., Gualano, M., Rovagnati, P. and Galli-Kienle, M. (1981) Ethynylestradiol-induced impairment of bile secretion in the rat: protective effects of S-adenosyl-L-methionine and its implication in estrogen metabolism. GastroenterologySO: 154-158.
145. Sullivan, D. M. and Huffman, J. L. (1983) Fractionation and kinetic properties of rat liver and kidney methionine adenosyltransferase isozymes. Biochemistry 22: 1636-1641.
146. Suma, Y., Yamanaka,Y. and Tsukada, K. (1983) Synthesis of Sadenosylmethionine synthetase isozymes from rat and mouse livers. Immunochemical studies. Biochim. Biophys. Acta 755: 287-292.
147. Surtees, R., Hyland, K. and Smith, I. (1990) Central nervous system methyl-group metabolism in children with neurological complications of HIV infection. Lancet 335: 619-621.
148. Surtees, R., Leonard, J. and Austin, S. (1991) Association of demyelination with deficiency of cerebrospinal-fluid S-adenosylmethionine in inborn errors of methyl-transfer pathway. Lancet 338: 1550-1554.
149. Tabor, H., Rosenthal, S. M. and Tabor, C. W. (1958) The biosynthesis of spermidine and spermine from putrescine and methionine. J. Biol. Chem. 233: 907-914.
150. Takusagawa, F., Kamitori, S., Misaki, S. and Markham, G. D. (1996) Crystal structure of S-adenosylmethionine synthetase. J. Biol. Chem. 271: 136-147.
151. Thomas, D. and Surdin-Kerjan, Y. (1987) SAM1, the structural gene for one of the S-adenosylmethionine synthetases in Saccharomyces cerevisiae. Sequence and expression. J. Biol. Chem. 262: 16704-16709.
152. Thomas, D. and Surdin-Kerjan, Y. (1991) The synthesis of the two S-adenosyl-methionine synthetases is differently regulated in Saccharomyces cerevisiae. Mol. Gen. Genet. 226: 224-232.
153. Thomas, D., Rothstein, R., Rosenberg, N. and Surdin-Kerjan, Y. (1988) SAM2 encodes the second methionine S-adenosyltransferase in Saccharomyces cerevisiae: physiology and regulation of both enzymes. Mol. Cell. Biol. 8: 5132-5139.
154. Tilghman, S. H. (1993) DNA methylation: a phoenix rises. Proc. Natl. Acad. Sci. USA 90: 8761-8762.
155. Traver, J., Varela, I. and Mato, J. M. (1984) Effect of exogenous S-adenosylmethionine on phosphatidylcholine synthesis by isolated rat hepatocytes. Biochem. Pharmacol. 33: 1562-1564.
156. Trimble, K., Molloy, A. M., Scott, J. and Weir, D. G. (1993) The effect of ethanol on one-carbon metabolism: increased methionine catabolism and lipotrope methyl-group wastage. Hepatology 18: 984-989.
157. Tronche, F. and Yaniv, M. (1992) HNF-1, a homeoprotein member of the hepatic transcription regulatory network. Bioessays 14: 579-587.
158. Truss, M. and Beato, M. (1993) Steroid hormone receptors: interaction with deoxyribonucleic acid and transcription factors. Endocr. Rev. 14: 459-479.
159. Tsukada, K., Yamano, H., Abe, T. and Okada, G. (1980) Ethionineinduced changes in the activities of S-adenosylmethionine synthetase isozymes from rat liver. Biochem. Biophys. Res. Commun. 95: 1160-1167.
160. Ubagai, T., Lei, K. J., Huang, S., Mudd, S. H., Levy, H. L. and Chou, J. Y. (1994) Disorders of transsulfuration. In: The Metabolic Basis of Inherited Diseases, pp. 1279-1327, Scriver, C. R., Beaudet, R., Charles, W. S. and Valle, D. (eds.) McGraw-Hill, Inc., New York.
161. Ubagai, T., Lei, K. J., Huang, S., Mudd, S. H., Levy, H. L. and Chou, J. Y. (1995) Molecular mechanisms of an inborn error of methionine pathway: methionine adenosyltransferase deficiency. J. Clin. Invest. 96: 1943-1947.
162. Vara, E., Arias-Diaz, J., Garcia, C., Villa, N., Simon, C., Ortiz, P. and Balibrea, J. L. (1994) S-Adenosyl-L-methionine might protect transplanted hepatocytes against the toxic effects of cytokines. Transplant. Proc. 26: 3363-3365.
163. Varela-Moreiras, G., Alonso-Aperte, E., Rubio, M., Gassó, M., Deulofeu, R., Alvarez, L., Caballería, J., Rodés, J. and Mato, J. M. (1995) Carbon tetrachloride-induced hepatic injury is associated with global DNA hypomethylation and homocysteinemia: effect of S-adenosylmethionine treatment. Hepatology 22: 1310-1315.
164. Vendemiale, G., Altomare, E., Trizio, T., Le Grazie, C., Di Padova, C., Salerno, M. T., Carrieri, V. and Albano, O. (1989) Effect of oral S-adenosyl-L-methionine on hepatic glutathione in patients with liver disease. Scand. J. Gastroenterol. 24: 407-415.
165. Villa, J. G., Almar, M. M., Collado, P. S., Lamazares, E. and Gonzalez-Gallego, J. (1993) Impairment of bile secretion induced by exhaustive exercise in the rat. Int. J. Sports Med. 14: 179-184.
166. Wainfan, E., Dizik, M., Slender, M. and Christman, J. K. (1991) Rapid appearance of hypomethylated DNA in liver of rats fed cancer promoting, methyl deficient diets. Carcinogenesis 12: 1307-1312.
167. 12-induced neuropathy in the pig. J. Neurochem. 51: 1949-1952.
168. Wu, G. and Thompson, J. R. (1989) Is methionine transaminated in skeletal muscle? Biochem. J. 257: 281-284.
169. Wu, J., Söderbergh, H., Karlsson, K. and Danielsson, A. (1996) Protective effect of S-adenosyl-L-methionine on bromobenzene-and D-galactosamine-induced toxicity to isolated rat hepatocytes. Hepatology 23: 359-365.
170. Xanthopoulos, K. G. and Mirkovitch, J. (1993) Gene regulation in rodent hepatocytes during development, differentiation and disease. Eur. J. Biochem. 216: 353-360.
171. Yasuda, H., Izumi, N., Shimada, O., Kobayakawa, T. and Nakanishi, T. (1980) The protective effect of tinoridine against carbon tetrachloride hepatotoxicity. Toxicol. Appl. Pharmacol. 52: 407-413.
172. Zaret, K. S. (1994) Genetic control of hepatocyte differentiation. In: The Liver Biology and Pathobiology, 3rd edn., pp. 53-68, Arias, I. M., Boyer, J. L., Fausto, N., Jakoby, W. B. and Schaachter, D. A. (eds.) Raven Press, New York.