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Chemical Compound Review

Myriocin     (E,2S,3S,4R)-2-amino-3,4- dihydroxy-2...

Synonyms: ISP-I, ISP-1, CHEMBL55076, M1177_SIGMA, CHEBI:582124, ...
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Disease relevance of Myriocin

  • Myriocin is an inhibitor of SPT and suppresses replication of the hepatitis C virus (HCV) replicon [1].
  • Male Balb/c mice, weighing 22 g were injected intraperitoneally with myriocin at 0, 0.1, 0.3, and 1.0 mg kg(-1) body weight daily for 5 days [2].
  • Results suggest that the mechanisms by which myriocin and silymarin protect renal cells are different, and silymarin potentially prevents fumonisin B1-induced toxicity by modulating TNFalpha expression or signals downstream of the inhibition of ceramide synthase [3].
  • FTY720, a synthetic myriocin analogue derived from culture filtrates of Isaria sinclairii, is a novel immunosuppressant that in experimental animals and nonhuman primates produces lymphocytopenia and prolongs allograft survival in dose-dependent fashion [4].

High impact information on Myriocin


Biological context of Myriocin


Anatomical context of Myriocin

  • ISP-1/myriocin is a potent inhibitor of sphingolipid biosynthesis and induces severe growth defects in eukaryotic cells because of the sphingolipid deprivation [13].
  • In L6 skeletal myoblasts induced to differentiate by Arg8-vasopressin treatment, a short-lived lowering of ceramide levels was observed, followed by a long-lasting elevation that was prevented by inhibitors of the de novo synthesis pathway, fumonisin B1 and myriocin [14].
  • BACKGROUND: Myriocin is a natural product that potently induces apoptosis of a murine cytotoxic T lymphocyte cell line (CTLL-2) and inhibits a serine palmitoyltransferase (SPT) activity that has been detected in cell extracts and is thought to initiate sphingolipid biosynthesis [15].
  • In Jurkat cells PDT-induced intracellular sphinganine accumulation, DEVDase activation, PARP cleavage, and apoptosis were suppressed by the de novo sphingolipid synthesis inhibitor ISP-1 (Myriocin) [16].
  • Finally, treatment of L. mexicana promastigotes with myriocin, an inhibitor of sphingolipid biosynthesis, demonstrated that ongoing sphingolipid biosynthesis is not required for the plasma-membrane transport of either gp63 or the GIPLs and that DRMs persist even when cellular levels of the major sphingolipid are depleted by 70% [17].

Associations of Myriocin with other chemical compounds


Gene context of Myriocin


Analytical, diagnostic and therapeutic context of Myriocin

  • Guided by these results, affinity chromatography matrices were prepared and two specific myriocin-binding proteins were isolated from CTLL-2 lysates [15].
  • To further test the ability of MALDI TOF-MS to quantify changes in phospholipid (PL) metabolic pathways, myriocin, an inhibitor of SM synthesis, was added to the cells [25].
  • Myriocin treatment resulted in significant reductions in both plasma SM and GSL concentration of 42% and 25%, as assessed by enzymatic and HPLC methods, respectively [26].
  • Immunosuppressive activities of those myriocin analogs on mouse allogeneic mixed lymphocyte reaction were examined, and Z-14-deoxomyriocin was found to show the most potent activity among them [27].
  • The mice were pretreated daily with intraperitoneal injection of 1.0 mg/kg myriocin 30 min before subcutaneous injections of 2.25 mg/kg of FB(1) for 3 days [28].


  1. Serine palmitoyltransferase inhibitor suppresses HCV replication in a mouse model. Umehara, T., Sudoh, M., Yasui, F., Matsuda, C., Hayashi, Y., Chayama, K., Kohara, M. Biochem. Biophys. Res. Commun. (2006) [Pubmed]
  2. Inhibition of serine palmitoyltransferase by myriocin, a natural mycotoxin, causes induction of c-myc in mouse liver. He, Q., Johnson, V.J., Osuchowski, M.F., Sharma, R.P. Mycopathologia (2004) [Pubmed]
  3. Pharmacological antagonism of fumonisin B1 cytotoxicity in porcine renal epithelial cells (LLC-PK1): a model for reducing fumonisin-induced nephrotoxicity in vivo. He, Q., Riley, R.T., Sharma, R.P. Pharmacol. Toxicol. (2002) [Pubmed]
  4. FTY720: from bench to bedside. Kahan, B.D. Transplant. Proc. (2004) [Pubmed]
  5. Lipid remodeling leads to the introduction and exchange of defined ceramides on GPI proteins in the ER and Golgi of Saccharomyces cerevisiae. Reggiori, F., Canivenc-Gansel, E., Conzelmann, A. EMBO J. (1997) [Pubmed]
  6. Ceramide synthesis enhances transport of GPI-anchored proteins to the Golgi apparatus in yeast. Horvath, A., Sütterlin, C., Manning-Krieg, U., Movva, N.R., Riezman, H. EMBO J. (1994) [Pubmed]
  7. A novel role for sphingolipid intermediates in activation-induced cell death in T cells. Solomon, J.C., Sharma, K., Wei, L.X., Fujita, T., Shi, Y.F. Cell Death Differ. (2003) [Pubmed]
  8. FTY720 Ameliorates Th1-Mediated Colitis in Mice by Directly Affecting the Functional Activity of CD4+CD25+ Regulatory T Cells. Daniel, C., Sartory, N., Zahn, N., Geisslinger, G., Radeke, H.H., Stein, J.M. J. Immunol. (2007) [Pubmed]
  9. Ceramide-mediated macroautophagy involves inhibition of protein kinase B and up-regulation of beclin 1. Scarlatti, F., Bauvy, C., Ventruti, A., Sala, G., Cluzeaud, F., Vandewalle, A., Ghidoni, R., Codogno, P. J. Biol. Chem. (2004) [Pubmed]
  10. Mitochondrial ceramide increases in UV-irradiated HeLa cells and is mainly derived from hydrolysis of sphingomyelin. Dai, Q., Liu, J., Chen, J., Durrant, D., McIntyre, T.M., Lee, R.M. Oncogene (2004) [Pubmed]
  11. Curcumin mediates ceramide generation via the de novo pathway in colon cancer cells. Moussavi, M., Assi, K., Gómez-Muñoz, A., Salh, B. Carcinogenesis (2006) [Pubmed]
  12. Reactions of serine palmitoyltransferase with serine and molecular mechanisms of the actions of serine derivatives as inhibitors. Ikushiro, H., Hayashi, H., Kagamiyama, H. Biochemistry (2004) [Pubmed]
  13. Disturbance of sphingolipid biosynthesis abrogates the signaling of Mss4, phosphatidylinositol-4-phosphate 5-kinase, in yeast. Kobayashi, T., Takematsu, H., Yamaji, T., Hiramoto, S., Kozutsumi, Y. J. Biol. Chem. (2005) [Pubmed]
  14. Inhibition of de novo ceramide synthesis upregulates phospholipase D and enhances myogenic differentiation. Mebarek, S., Komati, H., Naro, F., Zeiller, C., Alvisi, M., Lagarde, M., Prigent, A.F., Némoz, G. J. Cell. Sci. (2007) [Pubmed]
  15. The identification of myriocin-binding proteins. Chen, J.K., Lane, W.S., Schreiber, S.L. Chem. Biol. (1999) [Pubmed]
  16. A role for the de novo sphingolipids in apoptosis of photosensitized cells. Wispriyono, B., Schmelz, E., Pelayo, H., Hanada, K., Separovic, D. Exp. Cell Res. (2002) [Pubmed]
  17. Intracellular trafficking of glycosylphosphatidylinositol (GPI)-anchored proteins and free GPIs in Leishmania mexicana. Ralton, J.E., Mullin, K.A., McConville, M.J. Biochem. J. (2002) [Pubmed]
  18. Biochemical mechanisms of the generation of endogenous long chain ceramide in response to exogenous short chain ceramide in the A549 human lung adenocarcinoma cell line. Role for endogenous ceramide in mediating the action of exogenous ceramide. Ogretmen, B., Pettus, B.J., Rossi, M.J., Wood, R., Usta, J., Szulc, Z., Bielawska, A., Obeid, L.M., Hannun, Y.A. J. Biol. Chem. (2002) [Pubmed]
  19. Effect of myriocin on plasma sphingolipid metabolism and atherosclerosis in apoE-deficient mice. Hojjati, M.R., Li, Z., Zhou, H., Tang, S., Huan, C., Ooi, E., Lu, S., Jiang, X.C. J. Biol. Chem. (2005) [Pubmed]
  20. Ceramide signaling in fenretinide-induced endothelial cell apoptosis. Erdreich-Epstein, A., Tran, L.B., Bowman, N.N., Wang, H., Cabot, M.C., Durden, D.L., Vlckova, J., Reynolds, C.P., Stins, M.F., Groshen, S., Millard, M. J. Biol. Chem. (2002) [Pubmed]
  21. Inhibition of ceramide-redox signaling pathway blocks glomerular injury in hyperhomocysteinemic rats. Yi, F., Zhang, A.Y., Li, N., Muh, R.W., Fillet, M., Renert, A.F., Li, P.L. Kidney Int. (2006) [Pubmed]
  22. Involvement of endogenous ceramide in the inhibition of telomerase activity and induction of morphologic differentiation in response to all-trans-retinoic acid in human neuroblastoma cells. Kraveka, J.M., Li, L., Bielawski, J., Obeid, L.M., Ogretmen, B. Arch. Biochem. Biophys. (2003) [Pubmed]
  23. Aromatase inhibition by 15-deoxy-prostaglandin J(2) (15-dPGJ(2)) and N-(4-hydroxyphenyl)-retinamide (4HPR) is associated with enhanced ceramide production. Andrews, W.J., Winnett, G., Rehman, F., Shanmugasundaram, P., Hagen, D., Schrey, M.P. J. Steroid Biochem. Mol. Biol. (2005) [Pubmed]
  24. Loss of sphingosine kinase-1 activates the intrinsic pathway of programmed cell death: modulation of sphingolipid levels and the induction of apoptosis. Taha, T.A., Kitatani, K., El-Alwani, M., Bielawski, J., Hannun, Y.A., Obeid, L.M. FASEB J. (2006) [Pubmed]
  25. In vitro and in situ tracking of choline-phospholipid biogenesis by MALDI TOF-MS. Estrada, R., Borchman, D., Reddan, J., Hitt, A., Yappert, M.C. Anal. Chem. (2006) [Pubmed]
  26. Inhibition of atherosclerosis by the serine palmitoyl transferase inhibitor myriocin is associated with reduced plasma glycosphingolipid concentration. Glaros, E.N., Kim, W.S., Wu, B.J., Suarna, C., Quinn, C.M., Rye, K.A., Stocker, R., Jessup, W., Garner, B. Biochem. Pharmacol. (2007) [Pubmed]
  27. Syntheses, immunosuppressive activity, and structure-activity relationships of myriocin analogs, 2-epi-myriocin, 14-deoxomyriocin, Z-14-deoxyomyriocin, and nor-deoxomyriocins. Yoshikawa, M., Yokokawa, Y., Okuno, Y., Yagi, N., Murakami, N. Chem. Pharm. Bull. (1995) [Pubmed]
  28. Myriocin prevents fumonisin B1-induced sphingoid base accumulation in mice liver without ameliorating hepatotoxicity. He, Q., Riley, R.T., Sharma, R.P. Food Chem. Toxicol. (2005) [Pubmed]
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