Role of transmethylation reactions in alcoholic liver disease

World Journal of Gastroenterology

Volumn 13, Issue 37, 2007, Pages 4947-4954

  Kharbanda, Kusum K ^a,b  

^a VA Alcohol Research Center   (United States)

^b UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

Author keywords

Alcohol; Apoptosis; Betaine; Liver; Methyltransferases; S adenosylhomocysteine; Steatosis; Transmethylation

Indexed keywords

ALCOHOL; BETAINE; DNA METHYLTRANSFERASE; GLYCINE METHYLTRANSFERASE; HOMOCYSTEINE; METHIONINE; METHYLTRANSFERASE; PHOSPHATIDYLETHANOLAMINE METHYLTRANSFERASE; PROTEIN LEVO ISOASPARTATE METHYLTRANSFERASE; PROTEIN S ISOPRENYLCYSTEINE O METHYLTRANSFERASE; S ADENOSYLHOMOCYSTEINE; S ADENOSYLMETHIONINE; UNCLASSIFIED DRUG;

ALCOHOL ABUSE; ALCOHOL CONSUMPTION; ALCOHOL LIVER DISEASE; ALCOHOLIC FATTY LIVER; AMINO ACID METABOLISM; APOPTOSIS; ARTICLE; DRUG COST; DRUG EFFICACY; DRUG MECHANISM; DRUG SAFETY; ENZYME INHIBITION; HUMAN; LIPID STORAGE; LIVER INJURY; LIVER LEVEL; METHYLATION;

EID: 34848888039     PISSN: 10079327     EISSN: None     Source Type: Journal    
DOI: 10.3748/wjg.v13.i37.4947     Document Type: Article

References (75)

1. Mudd SH, Brosnan JT, Brosnan ME, Jacobs RL, Stabler SP, Allen RH, Vance DE, Wagner C. Methyl balance and transmethylation fluxes in humans. Am J Clin Nutr 2007; 85: 19-25
2. Schubert HL, Blumenthal RM, Cheng X. Many paths to methyltransfer: a chronicle of convergence. Trends Biochem Sci 2003; 28: 329-335
3. Finkelstein JD, Martin JJ. Methionine metabolism in mammals. Distribution of homocysteine between competing pathways. J Biol Chem 1984; 259: 9508-9513
4. Delgado-Reyes CV, Wallig MA, Garrow TA. Immunohistochemical detection of betaine-homocysteine S-methyltransferase in human, pig, and rat liver and kidney. Arch Biochem Biophys 2001; 393: 184-186
5. Barak AJ, Baker H, Tuma DJ. Influence of Ethanol on In-Vivo Levels of Hepatic Methylators Betaine and N5-Methyltetrahydrofolate in the Rat. IRCS Med Sci 1981; 9: 527-528
6. Barak AJ, Beckenhauer HC, Tuma DJ. Ethanol feeding inhibits the activity of N5-methyltetrahydrofolate-homocysteine methyltransferase in the rat. IRCS Med Sci 1985; 13: 760-761
7. Halsted CH, Villanueva J, Chandler CJ, Stabler SP, Allen RH, Muskhelishvili L, James SJ, Poirier L. Ethanol feeding of micropigs alters methionine metabolism and increases hepatocellular apoptosis and proliferation. Hepatology 1996; 23: 497-505
8. Trimble KC, Molloy AM, Scott JM, Weir DG. The effect of ethanol on one-carbon metabolism: increased methionine catabolism and lipotrope methyl-group wastage. Hepatology 1993; 18: 984-989
9. Barak AJ, Beckenhauer HC, Tuma DJ, Donohue TM. Adaptive increase in betaine-homocysteine methyltransferase activity maintains hepatic S-adenosylmethionine levels in ethanol-treated rats. IRCS Med Sci 1984; 12: 866-867
10. Barak AJ, Beckenhauer HC, Tuma DJ, Badakhsh S. Effects of prolonged ethanol feeding on methionine metabolism in rat liver. Biochem Cell Biol 1987; 65: 230-233
11. Lu SC, Huang ZZ, Yang H, Mato JM, Avila MA, Tsukamoto H. Changes in methionine adenosyltransferase and S-adenosylmethionine homeostasis in alcoholic rat liver. Am J Physiol Gastrointest Liver Physiol 2000; 279: G178-G185
12. Halsted CH, Villanueva JA, Devlin AM, Niemela O, Parkkila S, Garrow TA, Wallock LM, Shigenaga MK, Melnyk S, James SJ. Folate deficiency disturbs hepatic methionine metabolism and promotes liver injury in the ethanol-fed micropig. Proc Natl Acad Sci USA 2002; 99: 10072-10077
13. Cabrero C, Duce AM, Ortiz P, Alemany S, Mato JM. Specific loss of the high-molecular-weight form of S-adenosyl-L-methionine synthetase in human liver cirrhosis. Hepatology 1988; 8: 1530-1534
14. Duce AM, Ortiz P, Cabrero C, Mato JM. S-adenosyl-L-methionine synthetase and phospholipid methyltransferase are inhibited in human cirrhosis. Hepatology 1988; 8: 65-68
15. Barak AJ, Beckenhauer HC, Kharbanda KK, Tuma DJ. Chronic ethanol consumption increases homocysteine accumulation in hepatocytes. Alcohol 2001; 25: 77-81
16. Ji C, Kaplowitz N. Betaine decreases hyperhomocysteinemia, endoplasmic reticulum stress, and liver injury in alcohol-fed mice. Gastroenterology 2003; 124: 1488-1499
17. Barak AJ, Beckenhauer HC, Mailliard ME, Kharbanda KK, Tuma DJ. Betaine lowers elevated s-adenosylhomocysteine levels in hepatocytes from ethanol-fed rats. J Nutr 2003; 133: 2845-2848
18. Song Z, Zhou Z, Uriarte S, Wang L, Kang YJ, Chen T, Barve S, McClain CJ. S-adenosylhomocysteine sensitizes to TNF-alpha hepatotoxicity in mice and liver cells: a possible etiological factor in alcoholic liver disease. Hepatology 2004; 40: 989-997
19. Kharbanda KK, Mailliard ME, Baldwin CR, Beckenhauer HC, Sorrell MF, Tuma DJ. Betaine attenuates alcoholic steatosis by restoring phosphatidylcholine generation via the phosphatidylethanolamine methyltransferase pathway. J Hepatol 2007; 46: 314-321
20. Choi SW, Stickel F, Baik HW, Kim YI, Seitz HK, Mason JB. Chronic alcohol consumption induces genomic but not p53-specific DNA hypomethylation in rat colon. J Nutr 1999; 129: 1945-1950
21. Ubeda N, Alonso-Aperte E, Varela-Moreiras G. Acute valproate administration impairs methionine metabolism in rats. J Nutr 2002; 132: 2737-2742
22. Lu SC, Alvarez L, Huang ZZ, Chen L, An W, Corrales FJ, Avila MA, Kanel G, Mato JM. Methionine adenosyltransferase 1A knockout mice are predisposed to liver injury and exhibit increased expression of genes involved in proliferation. Proc Natl Acad Sci USA 2001; 98: 5560-5565
23. Esfandiari F, Villanueva JA, Wong DH, French SW, Halsted CH. Chronic ethanol feeding and folate deficiency activate hepatic endoplasmic reticulum stress pathway in micropigs. Am J Physiol Gastrointest Liver Physiol 2005; 289: G54-G63
24. Clarke S, Banfield K. S-adenosylmethionine-dependent methyltransferases. In: Carmel R, Jacobsen DW, eds. Homocysteine in health and disease. Cambridge: Cambridge University Press, 2001: 63-78
25. Barak AJ, Beckenhauer HC, Junnila M, Tuma DJ. Dietary betaine promotes generation of hepatic S-adenosylmethionine and protects the liver from ethanol-induced fatty infiltration. Alcohol Clin Exp Res 1993; 17: 552-555
26. Ji C, Deng Q, Kaplowitz N. Role of TNF-alpha in ethanol-induced hyperhomocysteinemia and murine alcoholic liver injury. Hepatology 2004; 40: 442-451
27. Pajares MA, Perez-Sala D. Betaine homocysteine S-methyltransferase: just a regulator of homocysteine metabolism? Cell Mol Life Sci 2006; 63: 2792-2803
28. Noga AA, Stead LM, Zhao Y, Brosnan ME, Brosnan JT, Vance DE. Plasma homocysteine is regulated by phospholipid methylation. J Biol Chem 2003; 278: 5952-5955
29. Kennedy EP, Weiss SB. The function of cytidine coenzymes in the biosynthesis of phospholipides. J Biol Chem 1956; 222: 193-214
30. Nishimaki-Mogami T, Yao Z, Fujimori K. Inhibition of phosphatidylcholine synthesis via the phosphatidylethanolamine methylation pathway impairs incorporation of bulk lipids into VLDL in cultured rat hepatocytes. J Lipid Res 2002; 43: 1035-1045
31. Noga AA, Zhao Y, Vance DE. An unexpected requirement for phosphatidylethanolamine N-methyltransferase in the secretion of very low density lipoproteins. J Biol Chem 2002; 277: 42358-42365
32. Zhu X, Song J, Mar MH, Edwards LJ, Zeisel SH. Phosphatidylethanolamine N-methyltransferase (PEMT) knockout mice have hepatic steatosis and abnormal hepatic choline metabolite concentrations despite ingesting a recommended dietary intake of choline. Biochem J 2003; 370: 987-993
33. Venkatesan S, Ward RJ, Peters TJ. Effect of chronic ethanol feeding on the hepatic secretion of very-low-density lipoproteins. Biochim Biophys Acta 1988; 960: 61-66
34. Lieber CS, Robins SJ, Leo MA. Hepatic phosphatidylethanolamine methyltransferase activity is decreased by ethanol and increased by phosphatidylcholine. Alcohol Clin Exp Res 1994; 18: 592-595
35. Hoffman DR, Harting JA, Cornatzer WE. Microsomal phosphatidylethanolamine methyltransferase: inhibition by S-adenosylhomocysteine. Lipids 1981; 16: 561-567
36. Kharbanda KK, Rogers DD 2nd, Mailliard ME, Siford GL, Barak AJ, Beckenhauer HC, Sorrell MF, Tuma DJ. A comparison of the effects of betaine and S-adenosylmethionine on ethanol-induced changes in methionine metabolism and steatosis in rat hepatocytes. J Nutr 2005; 135: 519-524
37. Li Z, Agellon LB, Allen TM, Umeda M, Jewell L, Mason A, Vance DE. The ratio of phosphatidylcholine to phosphatidylethanolamine influences membrane integrity and steatohepatitis. Cell Metab 2006; 3: 321-331
38. Rando RR. Chemical biology of isoprenylation/methylation. Biochem Soc Trans 1996; 24: 682-687
39. Bergo MO, Leung GK, Ambroziak P, Otto JC, Casey PJ, Young SG. Targeted inactivation of the isoprenylcysteine carboxyl methyltransferase gene causes mislocalization of K-Ras in mammalian cells. J Biol Chem 2000; 275: 17605-17610
40. Ratter F, Gassner C, Shatrov V, Lehmann V. Modulation of tumor necrosis factor-alpha-mediated cytotoxicity by changes of the cellular methylation state: mechanism and in vivo relevance. Int Immunol 1999; 11: 519-527
41. Kramer K, Harrington EO, Lu Q, Bellas R, Newton J, Sheahan KL, Rounds S. Isoprenylcysteine carboxyl methyltransferase activity modulates endothelial cell apoptosis. Mol Biol Cell 2003; 14: 848-857
42. Perez-Sala D, Gilbert BA, Rando RR, Canada FJ. Analogs of farnesylcysteine induce apoptosis in HL-60 cells. FEBS Lett 1998; 426: 319-324
43. Zhao Z, Kapoian T, Shepard M, Lianos EA. Adenosine-induced apoptosis in glomerular mesangial cells. Kidney Int 2002; 61: 1276-1285
44. Dawicki DD, Chatterjee D, Wyche J, Rounds S. Extracellular ATP and adenosine cause apoptosis of pulmonary artery endothelial cells. Am J Physiol 1997; 273: L485-L494
45. Bergo MO, Leung GK, Ambroziak P, Otto JC, Casey PJ, Gomes AQ, Seabra MC, Young SG. Isoprenylcysteine carboxyl methyltransferase deficiency in mice. J Biol Chem 2001; 276: 5841-5845
46. Lin X, Jung J, Kang D, Xu B, Zaret KS, Zoghbi H. Prenylcysteine carboxylmethyltransferase is essential for the earliest stages of liver development in mice. Gastroenterology 2002; 123: 345-351
47. Benedetti A, Marucci L. The significance of apoptosis in the liver. Liver 1999; 19: 453-463
48. Higuchi H, Kurose I, Kato S, Miura S, Ishii H. Ethanol-induced apoptosis and oxidative stress in hepatocytes. Alcohol Clin Exp Res 1996; 20: 340A-346A
49. Nanji AA. Apoptosis and alcoholic liver disease. Semin Liver Dis 1998; 18: 187-190
50. Casey CA, Nanji A, Cederbaum AI, Adachi M, Takahashi T. Alcoholic liver disease and apoptosis. Alcohol Clin Exp Res 2001; 25: 49S-53S
51. Deaciuc IV, D'Souza NB, de Villiers WJ, Burikhanov R, Sarphie TG, Hill DB, McClain CJ. Inhibition of caspases in vivo protects the rat liver against alcohol-induced sensitization to bacterial lipopolysaccharide. Alcohol Clin Exp Res 2001; 25: 935-943
52. Ji C, Kaplowitz N. Hyperhomocysteinemia, endoplasmic reticulum stress, and alcoholic liver injury. World J Gastroenterol 2004; 10: 1699-1708
53. Kharbanda KK, Rogers DD 2nd, Mailliard ME, Siford GL, Barak AJ, Beckenhauer HC, Sorrell MF, Tuma DJ. Role of elevated S-adenosylhomocysteine in rat hepatocyte apoptosis: protection by betaine. Biochem Pharmacol 2005; 70: 1883-1890
54. Craig SA. Betaine in human nutrition. Am J Clin Nutr 2004; 80: 539-549
55. Garrow TA. Purification, kinetic properties, and cDNA cloning of mammalian betaine-homocysteine methyltransferase. J Biol Chem 1996; 271: 22831-22838
56. Reif S, Aeed H, Shilo Y, Reich R, Kloog Y, Kweon YO, Bruck R. Treatment of thioacetamide-induced liver cirrhosis by the Ras antagonist, farnesylthiosalicylic acid. J Hepatol 2004; 41: 235-241
57. Thakur V, Pritchard MT, McMullen MR, Wang Q, Nagy LE. Chronic ethanol feeding increases activation of NADPH oxidase by lipopolysaccharide in rat Kupffer cells: role of increased reactive oxygen in LPS-stimulated ERK1/2 activation and TNF-alpha production. J Leukoc Biol 2006; 79: 1348-1356
58. Winter-Vann AM, Baron RA, Wong W, dela Cruz J, York JD, Gooden DM, Bergo MO, Young SG, Toone EJ, Casey PJ. A small-molecule inhibitor of isoprenylcysteine carboxyl methyltransferase with antitumor activity in cancer cells. Proc Natl Acad Sci USA 2005; 102: 4336-4341
59. Attwood JT, Yung RL, Richardson BC. DNA methylation and the regulation of gene transcription. Cell Mol Life Sci 2002; 59: 241-257
60. Shimizu T, Matsuoka Y, Shirasawa T. Biological significance of isoaspartate and its repair system. Biol Pharm Bull 2005; 28: 1590-1596
61. Kim E, Lowenson JD, MacLaren DC, Clarke S, Young SG. Deficiency of a protein-repair enzyme results in the accumulation of altered proteins, retardation of growth, and fatal seizures in mice. Proc Natl Acad Sci USA 1997; 94: 6132-6137
62. Johnson BA, Langmack EL, Aswad DW. Partial repair of deamidation-damaged calmodulin by protein carboxyl methyltransferase. J Biol Chem 1987; 262: 12283-12287
63. Lanthier J, Bouthillier A, Lapointe M, Demeule M, Beliveau R, Desrosiers RR. Down-regulation of protein L-isoaspartyl methyltransferase in human epileptic hippocampus contributes to generation of damaged tubulin. J Neurochem 2002; 83: 581-591
64. Ingrosso D, D'angelo S, di Carlo E, Perna AF, Zappia V, Galletti P. Increased methyl esterification of altered aspartyl residues in erythrocyte membrane proteins in response to oxidative stress. Eur J Biochem 2000; 267: 4397-4405
65. D'Angelo S, Ingrosso D, Perfetto B, Baroni A, Zappia M, Lobianco LL, Tufano MA, Galletti P. UVA irradiation induces L-isoaspartyl formation in melanoma cell proteins. Free Radic Biol Med 2001; 31: 1-9
66. Kharbanda KK, Mailliard ME, Baldwin CR, Sorrell MF, Tuma DJ. Accumulation of proteins bearing atypical isoaspartyl residues in livers of alcohol-fed rats is prevented by betaine administration: effects on protein-L-isoaspartyl methyltransferase activity. J Hepatol 2007; 46: 1119-1125
67. Miyakawa H, Liu J, Noguchi O, Marumo F, Sato C. Effect of alcohol drinking on gene expression of hepatic O6-methylguanine DNA methyltransferase in chronic liver diseases. Alcohol Clin Exp Res 1996; 20: 297A-300A
68. Shukla SD, Aroor AR. Epigenetic effects of ethanol on liver and gastrointestinal injury. World J Gastroenterol 2006; 12: 5265-5271
69. Wagner C, Decha-Umphai W, Corbin J. Phosphorylation modulates the activity of glycine N-methyltransferase, a folate binding protein. In vitro phosphorylation is inhibited by the natural folate ligand. J Biol Chem 1989; 264: 9638-9642
70. Schalinske KL, Nieman KM. Disruption of methyl group metabolism by ethanol. Nutr Rev 2005; 63: 387-391
71. Villanueva JA, Halsted CH. Hepatic transmethylation reactions in micropigs with alcoholic liver disease. Hepatology 2004; 39: 1303-1310
72. Junnila M, Barak AJ, Beckenhauer HC, Rahko T. Betaine reduces hepatic lipidosis induced by carbon tetrachloride in Sprague-Dawley rats. Vet Hum Toxicol 1998; 40: 263-266
73. Abdelmalek MF, Angulo P, Jorgensen RA, Sylvestre PB, Lindor KD. Betaine, a promising new agent for patients with nonalcoholic steatohepatitis: results of a pilot study. Am Gastroenterol 2001; 96: 2711-2717
74. Miglio F, Rovati LC, Santoro A, Setnikar I. Efficacy and safety of oral betaine glucuronate in non-alcoholic steatohepatitis. A double-blind, randomized, parallel-group, placebo-controlled prospective clinical study. Arzneimittelforschung 2000; 50: 722-727
75. Mukherjee S, Bernard T, Schafer D, Barak AJ, Sorrell MF, Tuma DJ. Impact of betaine on hepatic fibrosis and homocysteine in non-alcoholic steatohepatitis-A prospective cohort study. Hepatology 2005; 42: 610A