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Chemical Compound Review

D3627_SIGMA     [2-hydroxy-3-[(E)-octadec-9- enoyl]oxy...

Synonyms: AC1O5H1C, 1,3-Diolein, 1331-02-8, 12776-09-9, 25637-84-7, ...
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Disease relevance of GLYCEROL DIOLEATE


High impact information on GLYCEROL DIOLEATE

  • These data correlate with the observations that PKC preparations from dorsal and ventral ectoderm differ, the dorsal PKC preparation being more susceptible to activation by TPA and diolein than is the ventral PKC preparation [2].
  • In the case of the organic amines, this stability order is identical to the earlier observed permeability sequence for protonated organic amines in glyceryl dioleate bilayers treated with valinomycin, nonactin, or gramicidin, and in bullfrog and rabbit gallbladder membranes [3].
  • Glyceryl dioleate had effects on myotubes similar to those of TPA but with a reduced efficacy [4].
  • Exposing primary cultures of cerebellar granule neurons to 100 nM phorbol 12-myristate 13-acetate (PMA) for 24 hr decreases the Ca2+/phosphatidylserine/diolein-dependent protein kinase C (PKC; ATP:protein phosphotransferase, EC by approximately 90% in the 100,000 x g supernatant and pellet fractions of neuronal culture homogenates [5].
  • These enzymes, designated type I, II, and III protein kinase C, all have a molecular weight of 82,000, undergo autophosphorylation in the presence of Ca2+, phosphatidylserine, and diolein, and bind [3H]phorbol 12,13-dibutyrate [6].

Biological context of GLYCEROL DIOLEATE


Anatomical context of GLYCEROL DIOLEATE


Associations of GLYCEROL DIOLEATE with other chemical compounds

  • These FGFs, like diolein (Lee, H., Ghose-Dastidar, J., Winawer, S., and Friedman, E. (1993) J. Biol. Chem., 268, 5255-5263), increased the cellular concentration of long-chain diacylglycerols within the same short time period as they increased pp57 tyrosine phosphorylation [8].
  • Here we show molecular mechanisms of functional coupling of the two kinases. gammaPKC directly associated with DGKgamma through its accessory domain (AD), depending on Ca(2+) as well as phosphatidylserine/diolein in vitro [17].
  • Maximum phosphate incorporation into CB9 in the presence of 1 mM Ca2+, 75 micrograms/ml of phosphatidylserine, 2.5 micrograms/ml of diolein, and 12.5 micrograms/ml of dithiothreitol was 0.53 mol/mol of CB9 in 5 min [18].
  • In extracts derived from cells treated with 1,25(OH)2D3, the protein kinase C-dependent phosphorylation of endogenous U937 substrates stimulated by calcium, phosphatidyl serine, and diolein was increased compared to that observed in vehicle-treated cells [19].
  • In contrast, replacement of diolein (1,2-dioleoylglycerol) with 13HODE-DAG (1-palmitoyl,2-13HODE-glycerol) in the incubation mixture exerted no effect on total basal PKC activity [20].



Analytical, diagnostic and therapeutic context of GLYCEROL DIOLEATE


  1. Phosphorylation by protein kinase C and the responsiveness of Mg(2+)-ATPase to Ca2+ of myofibrils isolated from stunned and non-stunned porcine myocardium. Bezstarosti, K., Soei, L.K., Verdouw, P.D., Lamers, J.M. Mol. Cell. Biochem. (1997) [Pubmed]
  2. Protein kinase C and regulation of the local competence of Xenopus ectoderm. Otte, A.P., Kramer, I.M., Durston, A.J. Science (1991) [Pubmed]
  3. Cyclic polyether-protonated organic amine binding: significance in enzymatic and ion transport processes. Izatt, R.M., Izatt, N.E., Rossiter, B.E., Christensen, J.J., Haymore, B.L. Science (1978) [Pubmed]
  4. Agents that activate protein kinase C reduce acetylcholine sensitivity in cultured myotubes. Eusebi, F., Molinaro, M., Zani, B.M. J. Cell Biol. (1985) [Pubmed]
  5. Down-regulation of protein kinase C protects cerebellar granule neurons in primary culture from glutamate-induced neuronal death. Favaron, M., Manev, H., Siman, R., Bertolino, M., Szekely, A.M., DeErausquin, G., Guidotti, A., Costa, E. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  6. Isozymic forms of rat brain Ca2+-activated and phospholipid-dependent protein kinase. Huang, K.P., Nakabayashi, H., Huang, F.L. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  7. Tumor-promoting phorbol ester stimulates tyrosine phosphorylation in U-937 monocytes. Grunberger, G., Zick, Y., Taylor, S.I., Gorden, P. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  8. Signal transduction through extracellular signal-regulated kinase-like pp57 blocked in differentiated colon carcinoma cells having low levels of c-src kinase. Lee, H., Hsu, S., Winawer, S., Friedman, E. J. Biol. Chem. (1993) [Pubmed]
  9. Identification of a novel member of the carboxylesterase family that hydrolyzes triacylglycerol: a potential role in adipocyte lipolysis. Okazaki, H., Igarashi, M., Nishi, M., Tajima, M., Sekiya, M., Okazaki, S., Yahagi, N., Ohashi, K., Tsukamoto, K., Amemiya-Kudo, M., Matsuzaka, T., Shimano, H., Yamada, N., Aoki, J., Morikawa, R., Takanezawa, Y., Arai, H., Nagai, R., Kadowaki, T., Osuga, J., Ishibashi, S. Diabetes (2006) [Pubmed]
  10. Ca2+-independent activation of protease-activated kinase II by phospholipids/diolein and comparison with the Ca2+/phospholipid-dependent protein kinase. Gonzatti-Haces, M.I., Traugh, J.A. J. Biol. Chem. (1986) [Pubmed]
  11. Cellular mechanism of endothelin-1 release by angiotensin and vasopressin. Emori, T., Hirata, Y., Ohta, K., Kanno, K., Eguchi, S., Imai, T., Shichiri, M., Marumo, F. Hypertension (1991) [Pubmed]
  12. Differential effect of phorbol esters and interleukin-3 on protein kinase C isoform content and kinase activity in the FDC-P1 cell line. Ways, D.K., Qin, W., Riddle, R.S., Garris, T.D., Bennett, T.E., Steelman, L.S., McCubrey, J.A. Blood (1991) [Pubmed]
  13. Autophosphorylation of rat brain Ca2+-activated and phospholipid-dependent protein kinase. Huang, K.P., Chan, K.F., Singh, T.J., Nakabayashi, H., Huang, F.L. J. Biol. Chem. (1986) [Pubmed]
  14. Characterization of protein kinase C and its isoforms in human T lymphocytes. Beyers, A.D., Hanekom, C., Rheeder, A., Strachan, A.F., Wooten, M.W., Nel, A.E. J. Immunol. (1988) [Pubmed]
  15. Signal transduction through extracellular signal-regulated kinase-like pp57 blocked in differentiated cells having low protein kinase C beta activity. Lee, H., Ghose-Dastidar, J., Winawer, S., Friedman, E. J. Biol. Chem. (1993) [Pubmed]
  16. Evidence for the presence of CDP-ethanolamine: 1,2-diacyl-sn-glycerol ethanolaminephosphotransferase in rat central nervous system myelin. Wu, P.S., Ledeen, R.W. J. Neurochem. (1980) [Pubmed]
  17. Phosphorylation and Up-regulation of Diacylglycerol Kinase {gamma} via Its Interaction with Protein Kinase C{gamma}. Yamaguchi, Y., Shirai, Y., Matsubara, T., Sanse, K., Kuriyama, M., Oshiro, N., Yoshino, K., Yonezawa, K., Ono, Y., Saito, N. J. Biol. Chem. (2006) [Pubmed]
  18. Phosphorylation of a chromaffin granule-binding protein by protein kinase C. Summers, T.A., Creutz, C.E. J. Biol. Chem. (1985) [Pubmed]
  19. 1,25-Dihydroxyvitamin D3 enhances phorbol ester-stimulated differentiation and protein kinase C-dependent substrate phosphorylation activity in the U937 human monoblastoid cell. Ways, D.K., Dodd, R.C., Bennett, T.E., Gray, T.K., Earp, H.S. Endocrinology (1987) [Pubmed]
  20. Expression of protein kinase C isozymes in guinea pig epidermis: selective inhibition of PKC-beta activity by 13-hydroxyoctadecadienoic acid-containing diacylglycerol. Cho, Y., Ziboh, V.A. J. Lipid Res. (1994) [Pubmed]
  21. Partial purification and characterization of membrane-associated diacylglycerol kinase of Drosophila heads. Inoue, H., Yoshioka, T., Hotta, Y. Biochim. Biophys. Acta (1992) [Pubmed]
  22. Insulin receptors mediate growth effects in cultured fetal neurons. II. Activation of a protein kinase that phosphorylates ribosomal protein S6. Heidenreich, K.A., Toledo, S.P. Endocrinology (1989) [Pubmed]
  23. Protein kinase C isoenzymes in rat and human cardiovascular tissues. Erdbrügger, W., Keffel, J., Knocks, M., Otto, T., Philipp, T., Michel, M.C. Br. J. Pharmacol. (1997) [Pubmed]
  24. Regulation of erythrocyte Ca2+ pump activity by protein kinase C. Smallwood, J.I., Gügi, B., Rasmussen, H. J. Biol. Chem. (1988) [Pubmed]
  25. Activation of myelin protein kinase by diacylglycerol and 4 beta-phorbol 12-myristate 13-acetate. Murray, N., Steck, A.J. J. Neurochem. (1986) [Pubmed]
  26. Correlation between bilayer destabilization and activity enhancement by diacylglycerols in reconstituted Ca-ATPase vesicles. Cheng, K.H., Hui, S.W. Arch. Biochem. Biophys. (1986) [Pubmed]
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