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Chemical Compound Review

AdoMet     [(3S)-3-amino-3-carboxy- propyl]-[[(2R,3S...

Synonyms: Ademetionine, SAMe, Sam-Sulfate, SAMe Rx-Mood, CHEBI:15414, ...
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Disease relevance of S-adenosylmethionine

  • After 10 min of ischemia beta-hydroxypalmitoyl-CoA and beta-hydroxystearoyl-CoA constituted at least 16% of the incremental long-chain acyl-CoA, whereas beta-hydroxypalmitoylcarnitine and b-hydroxystearoylcarnitine constituted 8% of the incremental long-chain acylcarnitine [1].
  • Prophylaxis of early ventricular fibrillation by inhibition of acylcarnitine accumulation [2].
  • Biochemical studies revealed hyperlysinemia, hypocarnitinemia, normal organic acid profile, and an unusual acylcarnitine species in both urine and blood [3].
  • This retrospective analysis examined the bile acylcarnitine profiles of 27 children with acute liver failure who underwent liver transplantation or died [4].
  • Analysis of subgroups of patients with cirrhosis showed that patients with alcohol-induced cirrhosis had an increase in the total plasma carnitine concentration (67.8 +/- 29.5 vs. 55.2 +/- 9.9 micromol/L in control subjects), resulting from increases in both the short-chain and long-chain acylcarnitine concentration [5].

Psychiatry related information on S-adenosylmethionine


High impact information on S-adenosylmethionine

  • Metabolic profiling of 36 acylcarnitine species by tandem mass spectrometry revealed a unique decrease in the concentration of one lipid-derived metabolite, beta-OH-butyrate, in muscle of MCD-overexpressing animals [7].
  • Carnitine and acylcarnitine metabolism during exercise in humans. Dependence on skeletal muscle metabolic state [8].
  • Abnormalities are consistent with specific disruption of fatty-acid oxidation caused by impaired entry of long-chain acylcarnitine esters into the mitochondria and failure of the mitochondrial respiratory chain at complex 11 [9].
  • Criteria for the unequivocal diagnosis of MCAD deficiency by acylcarnitine analysis are an elevated C8-acylcarnitine concentration (> 0.3 microM), a ratio of C8/C10 acylcarnitines of > 5, and lack of elevated species of chain length > C10 [10].
  • The incorporation of [14C] arachidonic acid into the phospholipids and acylcarnitine (acyl-Cn) of spur cells and normal RBCs was analyzed by a direct-phase high performance liquid chromatography column to separate both the phospholipids and acyl-Cn [11].

Chemical compound and disease context of S-adenosylmethionine


Biological context of S-adenosylmethionine


Anatomical context of S-adenosylmethionine


Associations of S-adenosylmethionine with other chemical compounds


Gene context of S-adenosylmethionine

  • Import of acylcarnitine into mitochondrial matrix through carnitine/acylcarnitine-translocase (CACT) is fundamental for lipid catabolism [32].
  • The introduction of mass spectrometry to analyze blood acylcarnitine profiles has revolutionized the diagnosis of fatty acid oxidation disorders including CPT II deficiency [33].
  • Our results demonstrate different tissue-specific long-chain acylcarnitine profiles in response to various stressors, which may be of importance with respect to the heterogeneous clinical manifestations of VLCAD deficiency in humans [34].
  • However, the results indicate that Wy-14,643 does not prevent methylation by decreasing either the availability of SAM or the activity of DNA MTase [35].
  • Their plasma acylcarnitine profiles suggested the presence of LCHAD deficiency by demonstrating highly elevated 3-hydroxyacyl carnitines by tandem mass spectrometry (MS/MS) [36].

Analytical, diagnostic and therapeutic context of S-adenosylmethionine

  • The concentrations of free, short-chain, and long-chain acylcarnitine were determined in 19 right ventricular endomyocardial biopsies and in serum from 14 patients after orthotopic heart transplantation and 3 nontransplanted control patients with normal cardiac function [25].
  • The aliphatic chain distribution of myocardial acylcarnitine molecular species identified by electrospray ionization mass spectroscopy was independently substantiated by sequential HPLC purification and capillary gas chromatography [37].
  • Free, acetyl-, medium- and long-chain acylcarnitine and total plasma carnitine concentrations were measured in eight continuous ambulatory peritoneal dialysis (CAPD) patients and eight age- and sex-matched healthy controls [38].
  • We report a novel mild variant of medium-chain acyl-CoA dehydrogenase deficiency (MCADD) diagnosed in four infants who, in neonatal screening, showed abnormal acylcarnitine profiles indicative of MCADD [39].
  • Our study adds a novel method to the diagnosis of PBD, which may also be of benefit for future neonatal mass screening programs based on acylcarnitine profiling [40].


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  2. Prophylaxis of early ventricular fibrillation by inhibition of acylcarnitine accumulation. Corr, P.B., Creer, M.H., Yamada, K.A., Saffitz, J.E., Sobel, B.E. J. Clin. Invest. (1989) [Pubmed]
  3. 2,4-Dienoyl-coenzyme A reductase deficiency: a possible new disorder of fatty acid oxidation. Roe, C.R., Millington, D.S., Norwood, D.L., Kodo, N., Sprecher, H., Mohammed, B.S., Nada, M., Schulz, H., McVie, R. J. Clin. Invest. (1990) [Pubmed]
  4. Abnormal concentrations of esterified carnitine in bile: a feature of pediatric acute liver failure with poor prognosis. Shneider, B.L., Rinaldo, P., Emre, S., Bucuvalas, J., Squires, R., Narkewicz, M., Gondolesi, G., Magid, M., Morotti, R., Hynan, L.S. Hepatology (2005) [Pubmed]
  5. Carnitine metabolism in patients with chronic liver disease. Krähenbühl, S., Reichen, J. Hepatology (1997) [Pubmed]
  6. Cerebrospinal fluid carnitine levels in patients with Alzheimer's disease. Rubio, J.C., de Bustos, F., Molina, J.A., Jiménez-Jiménez, F.J., Benito-León, J., Martín, M.A., Campos, Y., Ortí-Pareja, M., Cabrera-Valdivia, F., Arenas, J. J. Neurol. Sci. (1998) [Pubmed]
  7. Hepatic expression of malonyl-CoA decarboxylase reverses muscle, liver and whole-animal insulin resistance. An, J., Muoio, D.M., Shiota, M., Fujimoto, Y., Cline, G.W., Shulman, G.I., Koves, T.R., Stevens, R., Millington, D., Newgard, C.B. Nat. Med. (2004) [Pubmed]
  8. Carnitine and acylcarnitine metabolism during exercise in humans. Dependence on skeletal muscle metabolic state. Hiatt, W.R., Regensteiner, J.G., Wolfel, E.E., Ruff, L., Brass, E.P. J. Clin. Invest. (1989) [Pubmed]
  9. Impaired fatty acid oxidation in propofol infusion syndrome. Wolf, A., Weir, P., Segar, P., Stone, J., Shield, J. Lancet (2001) [Pubmed]
  10. Medium-chain acyl-CoA dehydrogenase (MCAD) deficiency: diagnosis by acylcarnitine analysis in blood. Van Hove, J.L., Zhang, W., Kahler, S.G., Roe, C.R., Chen, Y.T., Terada, N., Chace, D.H., Iafolla, A.K., Ding, J.H., Millington, D.S. Am. J. Hum. Genet. (1993) [Pubmed]
  11. Abnormal phospholipid metabolism in spur cell anemia: decreased fatty acid incorporation into phosphatidylethanolamine and increased incorporation into acylcarnitine in spur cell anemia erythrocytes. Allen, D.W., Manning, N. Blood (1994) [Pubmed]
  12. High doses of L-carnitine in acute myocardial infarction: metabolic and antiarrhythmic effects. Rizzon, P., Biasco, G., Di Biase, M., Boscia, F., Rizzo, U., Minafra, F., Bortone, A., Siliprandi, N., Procopio, A., Bagiella, E. Eur. Heart J. (1989) [Pubmed]
  13. Altered interactions between lipogenesis and fatty acid oxidation in regenerating rat liver. Schofield, P.S., Sugden, M.C., Corstorphine, C.G., Zammit, V.A. Biochem. J. (1987) [Pubmed]
  14. Isolated mitochondrial myopathy associated with muscle coenzyme Q10 deficiency. Lalani, S.R., Vladutiu, G.D., Plunkett, K., Lotze, T.E., Adesina, A.M., Scaglia, F. Arch. Neurol. (2005) [Pubmed]
  15. Inborn errors of metabolism diagnosed in sudden death cases by acylcarnitine analysis of postmortem bile. Rashed, M.S., Ozand, P.T., Bennett, M.J., Barnard, J.J., Govindaraju, D.R., Rinaldo, P. Clin. Chem. (1995) [Pubmed]
  16. Renal handling of carnitine in children with carnitine deficiency and hyperammonemia associated with valproate therapy. Matsuda, I., Ohtani, Y., Ninomiya, N. J. Pediatr. (1986) [Pubmed]
  17. Insights into cephamycin biosynthesis: the crystal structure of CmcI from Streptomyces clavuligerus. Oster, L.M., Lester, D.R., Terwisscha van Scheltinga, A., Svenda, M., van Lun, M., Généreux, C., Andersson, I. J. Mol. Biol. (2006) [Pubmed]
  18. Supplemental carnitine and exercise. Brass, E.P. Am. J. Clin. Nutr. (2000) [Pubmed]
  19. Strategy for the isolation, derivatization, chromatographic separation, and detection of carnitine and acylcarnitines. Minkler, P.E., Ingalls, S.T., Hoppel, C.L. Anal. Chem. (2005) [Pubmed]
  20. Rapid switch of hepatic fatty acid metabolism from oxidation to esterification during diurnal feeding of meal-fed rats correlates with changes in the properties of acetyl-CoA carboxylase, but not of carnitine palmitoyltransferase I. Moir, A.M., Zammit, V.A. Biochem. J. (1993) [Pubmed]
  21. Influences of silicates and carnitine-silicate mixtures on the inhibition of aggregation of erythrocytes elicited by the presence of fibrinogen. Ramsohoye, P., Fritz, I.B. J. Cell. Physiol. (1995) [Pubmed]
  22. Inhibition of gap junctional conductance by long-chain acylcarnitines and their preferential accumulation in junctional sarcolemma during hypoxia. Wu, J., McHowat, J., Saffitz, J.E., Yamada, K.A., Corr, P.B. Circ. Res. (1993) [Pubmed]
  23. Regulation of the long-chain carnitine acyltransferases. Brady, P.S., Ramsay, R.R., Brady, L.J. FASEB J. (1993) [Pubmed]
  24. Short-chain acyl-CoA dehydrogenase deficiency: a cause of ophthalmoplegia and multicore myopathy. Tein, I., Haslam, R.H., Rhead, W.J., Bennett, M.J., Becker, L.E., Vockley, J. Neurology (1999) [Pubmed]
  25. Correlation between long-chain acylcarnitine in serum and myocardium after heart transplantation in humans. Olbrich, H.G., Evangeliou, A., Tabatabaei, S.B., Cieslinski, G., Hartmann, A., Beyersdorf, F., Hermann, G., Böhles, H. Am. J. Clin. Nutr. (1994) [Pubmed]
  26. Phytanic acid and pristanic acid are oxidized by sequential peroxisomal and mitochondrial reactions in cultured fibroblasts. Verhoeven, N.M., Roe, D.S., Kok, R.M., Wanders, R.J., Jakobs, C., Roe, C.R. J. Lipid Res. (1998) [Pubmed]
  27. Properties of purified carnitine acyltransferases of mouse liver peroxisomes. Farrell, S.O., Fiol, C.J., Reddy, J.K., Bieber, L.L. J. Biol. Chem. (1984) [Pubmed]
  28. Quantitation of acyl-CoA and acylcarnitine esters accumulated during abnormal mitochondrial fatty acid oxidation. Kler, R.S., Jackson, S., Bartlett, K., Bindoff, L.A., Eaton, S., Pourfarzam, M., Frerman, F.E., Goodman, S.I., Watmough, N.J., Turnbull, D.M. J. Biol. Chem. (1991) [Pubmed]
  29. Amphipathic lipid metabolites and their relation to arrhythmogenesis in the ischemic heart. DaTorre, S.D., Creer, M.H., Pogwizd, S.M., Corr, P.B. J. Mol. Cell. Cardiol. (1991) [Pubmed]
  30. Long-chain acyl-CoA and acylcarnitine hydrolase activities in normal and ischemic rabbit heart. Moore, K.H., Bonema, J.D., Solomon, F.J. J. Mol. Cell. Cardiol. (1984) [Pubmed]
  31. Effect of carnitine on lipid metabolism in the neonate. II. Carnitine addition to lipid infusion during prolonged total parenteral nutrition. Orzali, A., Maetzke, G., Donzelli, F., Rubaltelli, F.F. J. Pediatr. (1984) [Pubmed]
  32. Differential carnitine/acylcarnitine translocase expression defines distinct metabolic signatures in skeletal muscle cells. Peluso, G., Petillo, O., Margarucci, S., Grippo, P., Melone, M.A., Tuccillo, F., Calvani, M. J. Cell. Physiol. (2005) [Pubmed]
  33. Carnitine palmitoyltransferase II deficiency: a clinical, biochemical, and molecular review. Sigauke, E., Rakheja, D., Kitson, K., Bennett, M.J. Lab. Invest. (2003) [Pubmed]
  34. Tissue carnitine homeostasis in very-long-chain acyl-CoA dehydrogenase-deficient mice. Spiekerkoetter, U., Tokunaga, C., Wendel, U., Mayatepek, E., Ijlst, L., Vaz, F.M., van Vlies, N., Overmars, H., Duran, M., Wijburg, F.A., Wanders, R.J., Strauss, A.W. Pediatr. Res. (2005) [Pubmed]
  35. Wy-14,643-induced hypomethylation of the c-myc gene in mouse liver. Ge, R., Wang, W., Kramer, P.M., Yang, S., Tao, L., Pereira, M.A. Toxicol. Sci. (2001) [Pubmed]
  36. Identification of novel mutations of the HADHA and HADHB genes in patients with mitochondrial trifunctional protein deficiency. Choi, J.H., Yoon, H.R., Kim, G.H., Park, S.J., Shin, Y.L., Yoo, H.W. Int. J. Mol. Med. (2007) [Pubmed]
  37. Accumulation of unsaturated acylcarnitine molecular species during acute myocardial ischemia: metabolic compartmentalization of products of fatty acyl chain elongation in the acylcarnitine pool. Ford, D.A., Han, X., Horner, C.C., Gross, R.W. Biochemistry (1996) [Pubmed]
  38. Free and esterified carnitine in continuous ambulatory peritoneal dialysis patients. Constantin-Teodosiu, D., Kirby, D.P., Short, A.H., Burden, R.P., Morgan, A.G., Greenhaff, P.L. Kidney Int. (1996) [Pubmed]
  39. Molecular and functional characterisation of mild MCAD deficiency. Zschocke, J., Schulze, A., Lindner, M., Fiesel, S., Olgemöller, K., Hoffmann, G.F., Penzien, J., Ruiter, J.P., Wanders, R.J., Mayatepek, E. Hum. Genet. (2001) [Pubmed]
  40. Characteristic acylcarnitine profiles in inherited defects of peroxisome biogenesis: a novel tool for screening diagnosis using tandem mass spectrometry. Rizzo, C., Boenzi, S., Wanders, R.J., Duran, M., Caruso, U., Dionisi-Vici, C. Pediatr. Res. (2003) [Pubmed]
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