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Chemical Compound Review

Macrofusine     (2S)-2-[[ (5S,6R,7R,9R,11S,16R,18S,19S) -19...

Synonyms: LS-1, fumonisin b1, CHEMBL91690, CCRIS 4433, HSDB 7077, ...
 
 
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Disease relevance of HSDB 7077

 

High impact information on HSDB 7077

  • An obligatory role for ceramide synthase was defined, since its natural specific inhibitor, fumonisin B1, blocked daunorubicin-induced ceramide elevation and apoptosis [5].
  • Addition of exogenous ceramide, to circumvent the FB1 block, restored GP-2 and Na/K-ATPase sorting to the apical and basal-lateral membranes, respectively [6].
  • To examine this apparent inter-relationship between sorting of GlcCer, GP-2 and Na/K-ATPase, sphingolipid synthesis was inhibited in clone II/G cells with the fungal metabolite, Fumonisin B1 (FB1) [6].
  • In the presence of FB1, GP-2 and Na/K-ATPase are delivered to both apical and basal-lateral membranes, similar to clone II/J cells; FB1 had no effect on sorting of E-cadherin to the basal-lateral membrane of II/G cells [6].
  • Significantly, we discovered that fumonisin B1 (FB1) treatment of Arabidopsis triggered the depletion of extracellular ATP that preceded cell death and that exogenous ATP rescues Arabidopsis from FB1-induced death [7].
 

Chemical compound and disease context of HSDB 7077

 

Biological context of HSDB 7077

 

Anatomical context of HSDB 7077

 

Associations of HSDB 7077 with other chemical compounds

  • In a previous study we observed that long term (5 days) incubation with fumonisin B1 (FB1), an inhibitor of acylation of sphingoid long chain bases to (dihydro)ceramide, resulted in morphological and biochemical changes in 3T3 fibroblasts (Meivar-Levy, I., Sabanay, H., Bershadsky, A. D., and Futerman, A. H. (1997) J. Biol. Chem. 272, 1558-1564) [23].
  • Also, the activity was not inhibited in vitro and in cells by fumonisin B1, an inhibitor of the CoA-dependent ceramide synthase [24].
  • A specific inhibitor of ceramide synthase, fumonisin B1, had no effect on daunorubicin induced NFkappaB activation at a range of concentrations previously reported to block apoptosis induced by this drug [25].
  • However, disruption of lipid rafts by removal of cholesterol did not cause surface missorting of PLAP and NTR-PLAP, and the altered surface sorting of these proteins after Fumonisin B1 treatment did not correlate with reduced levels in Triton X-100 -insoluble fractions [26].
  • Moreover, eluted LASS5-HA was highly selective toward palmitoyl-CoA as acyl donor and was inhibited by the (dihydro)ceramide synthase inhibitor, fumonisin B1 [27].
 

Gene context of HSDB 7077

  • Upstream of growth and differentiation factor 1 (uog1), a mammalian homolog of the yeast longevity assurance gene 1 (LAG1), regulates N-stearoyl-sphinganine (C18-(dihydro)ceramide) synthesis in a fumonisin B1-independent manner in mammalian cells [28].
  • Here we report the cloning and characterization of the yeast gene YPC1 (YBR183w) by screening Saccharomyces cerevisiae genes whose overexpression bestows resistance to fumonisin B1 [29].
  • Based on these data, LAG1 and LAC1 are the first genes to be identified that are required for the fumonisin B1-sensitive and acyl-CoA-dependent ceramide synthase reaction [30].
  • Overexpression of YDC1p had no reverse activity in non-stressed yeast cells, but like YPC1p suppressed the inhibition of growth by fumonisin B1 albeit more modestly [31].
  • Moreover, western blot analysis showed that fumonisin B1 was not able to decrease the overexpression of P-gp induced by DOX [32].
 

Analytical, diagnostic and therapeutic context of HSDB 7077

References

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  14. gamma-Tocopherol or combinations of vitamin E forms induce cell death in human prostate cancer cells by interrupting sphingolipid synthesis. Jiang, Q., Wong, J., Fyrst, H., Saba, J.D., Ames, B.N. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
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  19. Cell membrane GM1 ganglioside is a functional coreceptor for fibroblast growth factor 2. Rusnati, M., Urbinati, C., Tanghetti, E., Dell'Era, P., Lortat-Jacob, H., Presta, M. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
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  21. The role of sphingolipids in the maintenance of fibroblast morphology. The inhibition of protrusional activity, cell spreading, and cytokinesis induced by fumonisin B1 can be reversed by ganglioside GM3. Meivar-Levy, I., Sabanay, H., Bershadsky, A.D., Futerman, A.H. J. Biol. Chem. (1997) [Pubmed]
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  26. Detergent-insoluble GPI-anchored proteins are apically sorted in fischer rat thyroid cells, but interference with cholesterol or sphingolipids differentially affects detergent insolubility and apical sorting. Lipardi, C., Nitsch, L., Zurzolo, C. Mol. Biol. Cell (2000) [Pubmed]
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  28. Upstream of growth and differentiation factor 1 (uog1), a mammalian homolog of the yeast longevity assurance gene 1 (LAG1), regulates N-stearoyl-sphinganine (C18-(dihydro)ceramide) synthesis in a fumonisin B1-independent manner in mammalian cells. Venkataraman, K., Riebeling, C., Bodennec, J., Riezman, H., Allegood, J.C., Sullards, M.C., Merrill, A.H., Futerman, A.H. J. Biol. Chem. (2002) [Pubmed]
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  32. P-glycoprotein (ABCB1) but not multidrug resistance-associated protein 1 (ABCC1) is induced by doxorubicin in primary cultures of rat astrocytes. Mercier, C., Declèves, X., Masseguin, C., Fragner, P., Tardy, M., Roux, F., Gabrion, J., Scherrmann, J.M. J. Neurochem. (2003) [Pubmed]
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