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Chemical Compound Review

AC1L459O     (2-hydroxy-3-octanoyloxy- propyl) octanoate

Synonyms: 1,3-Dogl, 1,3-Dcg, 1429-66-9, 36354-80-0, EINECS 252-992-1, ...
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Disease relevance of Dioctanoylglycerol

  • Here, we show that treatment of choriocarcinoma cells with activators of protein kinase C, such as phorbol myristate acetate (PMA) and dioctanoylglycerol, increases accumulation of the mRNAs for both subunits of hCG by 3-4-fold [1].
  • Dioctanoylglycerol, a synthetic diacylglycerol, stimulated [14C]choline uptake in cultured human neuroblastoma (LA-N-2) cells [2].
  • Activators of protein kinase C, such as tetradecanoylphorbol acetate (TPA) and dioctanoylglycerol (DG), caused a 3-4-fold accumulation of LDH A subunit mRNA in rat C6 glioma cells [3].

High impact information on Dioctanoylglycerol

  • Exposure to the synthetic diacylglycerol (DAG), dioctanoylglycerol, also inhibits AVP-stimulated AC activity; therefore, inhibition by EGF is due to activation of protein kinase C. Thus, in cultured rat inner medullary collecting duct cells, cAMP and DAG function as mutually inhibitory second messengers with each impairing formation of the other [4].
  • BisPA formation is rapid (15 s) and transient (peaks at 2-10 min) and is also induced by other stimuli capable of raising DG and activating PLD simultaneously, e.g. endothelin, lysophosphatidic acid, fetal calf serum, phorbol ester, dioctanoylglycerol or bacterial PLC [5].
  • Like PKC itself, these peptides also recognize other PKC activators, including dioctanoylglycerol and teleocidin B-4, and exhibit an ability to differentiate phorbol ester from its C-4 epimer [6].
  • The synthetic diacylglycerols 1,2-dihexanoylglycerol and 1,2-dioctanoylglycerol enhanced light-induced stomatal opening in Commelina communis and induced stomatal opening under darkness, whereas an isomer with no known second-messenger role, 1,3-dioctanoylglycerol, did not affect stomatal responses [7].
  • Treatment of intact cells with isoproterenol, forskolin, or cAMP analogues to stimulate cAMP-dependent protein kinase (PKA) or with phorbol ester or dioctanoylglycerol to stimulate Ca2+/phospholipid-dependent protein kinase (PKC) produced activation of membrane PTPase complex without a change in its size [8].

Biological context of Dioctanoylglycerol

  • In synergy with subthreshold gamma-thrombin or collagen, exogenous diC8 reconstituted platelet activation [9].
  • The changes in both mobility and amino-terminal phosphorylation can be reproduced by known activators of protein kinase C (4 alpha-phorbol 12 beta-myristate, dioctanoylglycerol), suggesting that this signal transduction pathway (or related pathways) mediates at least part of these events [10].
  • Regulation of myocardial contraction by diacylglycerol was investigated in the present study by releasing the diacylglycerol analogue dioctanoylglycerol (diC8) within adult rat ventricular myocytes by using a light-sensitive caged compound [11].
  • Exposure of cells to 100 nM 12-O-tetradecanoylphorbol-13-acetate for 15 min increased the phosphorylation of PKC by 5-fold in the particulate fraction, while treatment with 100 microM dioctanoylglycerol enhanced phosphorylation of PKC only by 2-fold [12].
  • Using phorbol esters to (i) activate the enzyme and (ii) to down-regulate it, we report that differential activation (translocation) of PKC alpha is associated with AA release in MDCK cells and that specific down-regulation of PKC alpha is associated with a loss of AA release in response to stimulation with dioctanoylglycerol and phorbol ester [13].

Anatomical context of Dioctanoylglycerol

  • The data provide evidence that diacylglycerol can induce a strong positive inotropic effect in mammalian ventricular muscle, possibly by activating protein kinase C. By contrast, perfusion of diC8 extracellularly onto myocytes caused a 42 +/- 2% decline in twitch amplitude, in accordance with previous reports [11].
  • Phorbol ester and dioctanoylglycerol stimulate membrane association of protein kinase C and have a negative inotropic effect mediated by changes in cytosolic Ca2+ in adult rat cardiac myocytes [14].
  • This postulate is based on the stimulatory effect of agents that can mimic the activity of endogenous diacylglycerol (PMA and other biologically active phorbol compounds, mezerein, and L-alpha-1,2 dioctanoylglycerol) and inositol trisphosphate (ionomycin) on Mo3e expression by U-937 and HL-60 cells [15].
  • Phorbol diesters and dioctanoylglycerol stimulate accumulation of both diacylglycerols and alkylacylglycerols in human neutrophils [16].
  • In kinetic studies, EA 1 expression was seen as early as 1 h in diOG- and PMA-activated T cells [17].

Associations of Dioctanoylglycerol with other chemical compounds


Gene context of Dioctanoylglycerol

  • Furthermore, treatment of adipocytes with dioctanoylglycerol, which activates ERK, increases lipolysis, although MEK inhibitors decrease dioctanoylglycerol-stimulated activation of lipolysis [22].
  • In contrast, the sustained phase of the response to AVP and OT was abolished by removal of Ca2+e. The effect of dioctanoylglycerol, which elicits a sustained progressive increase in ACTH release, but no initial spike phase, was also greatly inhibited by Ca2+e removal; no greater effect was observed when Ca2+i was depleted [23].
  • Bath application of dioctanoylglycerol (diC8), a diacylglycerol (DAG) analogue which is capable of directly activating PKC, caused a gradual decline in peak ICa (50.4 +/- 6.2 %, n = 5) and increased the rate of current decay [24].
  • Our results demonstrate that both ET-1 and intracellularly photoreleased diC8 increase ICa by a PKC-mediated pathway, which is in direct contrast to the PKC-independent inhibition of ICa produced by bath-applied diC8 [24].
  • Our observations demonstrate that a physiologic regulator of PKC, diC8, and cell surface crosslinking of the CD2 and CD3 antigen, promote gene expression in normal human quiescent T-cells independently of accessory cells, and that CsA prevents gene expression via a direct effect on T-cells [25].

Analytical, diagnostic and therapeutic context of Dioctanoylglycerol


  1. Cyclic AMP and phorbol esters interact synergistically to regulate expression of the chorionic gonadotropin genes. Andersen, B., Milsted, A., Kennedy, G., Nilson, J.H. J. Biol. Chem. (1988) [Pubmed]
  2. Dioctanoylglycerol stimulates accumulation of [methyl-14C]choline and its incorporation into acetylcholine and phosphatidylcholine in a human cholinergic neuroblastoma cell line. Slack, B.E., Richardson, U.I., Nitsch, R.M., Wurtman, R.J. Brain Res. (1992) [Pubmed]
  3. Transcriptional regulation of the lactate dehydrogenase A subunit gene by the phorbol ester 12-O-tetradecanoylphorbol-13-acetate. Huang, D., Jungmann, R.A. Mol. Cell. Endocrinol. (1995) [Pubmed]
  4. Cyclic adenosine monophosphate and diacylglycerol. Mutually inhibitory second messengers in cultured rat inner medullary collecting duct cells. Teitelbaum, I. J. Clin. Invest. (1990) [Pubmed]
  5. Rapid attenuation of receptor-induced diacylglycerol and phosphatidic acid by phospholipase D-mediated transphosphatidylation: formation of bisphosphatidic acid. van Blitterswijk, W.J., Hilkmann, H. EMBO J. (1993) [Pubmed]
  6. Identification, activity, and structural studies of peptides incorporating the phorbol ester-binding domain of protein kinase C. Wender, P.A., Irie, K., Miller, B.L. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  7. Diacylglycerols induce both ion pumping in patch-clamped guard-cell protoplasts and opening of intact stomata. Lee, Y., Assmann, S.M. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  8. Activation of membrane protein-tyrosine phosphatase involving cAMP- and Ca2+/phospholipid-dependent protein kinases. Brautigan, D.L., Pinault, F.M. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  9. Delayed accumulation of diacylglycerol in platelets as a mechanism for regulation of onset of aggregation and secretion. Werner, M.H., Hannun, Y.A. Blood (1991) [Pubmed]
  10. Alterations of the lymphocyte-specific protein tyrosine kinase (p56lck) during T-cell activation. Veillette, A., Horak, I.D., Horak, E.M., Bookman, M.A., Bolen, J.B. Mol. Cell. Biol. (1988) [Pubmed]
  11. Positive inotropy mediated by diacylglycerol in rat ventricular myocytes. Pi, Y., Sreekumar, R., Huang, X., Walker, J.W. Circ. Res. (1997) [Pubmed]
  12. Tumor promoter 12-O-tetradecanoylphorbol-13-acetate and sn-1,2-dioctanoylglycerol increase the phosphorylation of protein kinase C in cells. Molina, C.A., Ashendel, C.L. Cancer Res. (1991) [Pubmed]
  13. Differential activation of protein kinase C alpha is associated with arachidonate release in Madin-Darby canine kidney cells. Godson, C., Weiss, B.A., Insel, P.A. J. Biol. Chem. (1990) [Pubmed]
  14. Phorbol ester and dioctanoylglycerol stimulate membrane association of protein kinase C and have a negative inotropic effect mediated by changes in cytosolic Ca2+ in adult rat cardiac myocytes. Capogrossi, M.C., Kaku, T., Filburn, C.R., Pelto, D.J., Hansford, R.G., Spurgeon, H.A., Lakatta, E.G. Circ. Res. (1990) [Pubmed]
  15. Regulation of human monocyte surface antigen expression. I. Up-modulation of Mo3e antigen expression on U-937 and HL-60 cells stimulated by pharmacologic activators of protein kinase C. Todd, R.F., Bury, M.J., Alvarez, P.A., Brott, D.A., Liu, D.Y. Blood (1986) [Pubmed]
  16. Phorbol diesters and dioctanoylglycerol stimulate accumulation of both diacylglycerols and alkylacylglycerols in human neutrophils. Rider, L.G., Dougherty, R.W., Niedel, J.E. J. Immunol. (1988) [Pubmed]
  17. The 28-kDa/32-kDa activation antigen EA 1. Further characterization and signal requirements for its expression. Bjorndahl, J.M., Nakamura, S., Hara, T., Jung, L.K., Fu, S.M. J. Immunol. (1988) [Pubmed]
  18. Protein kinase C is not necessary for peptide-induced suppression of M current or for desensitization of the peptide receptors. Bosma, M.M., Hille, B. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  19. Activation signals in human lymphocytes. Incorporation of polyunsaturated fatty acids into plasma membrane phospholipids regulates IL-2 synthesis via sustained activation of protein kinase C. Szamel, M., Rehermann, B., Krebs, B., Kurrle, R., Resch, K. J. Immunol. (1989) [Pubmed]
  20. Exogenous sn-1,2-diacylglycerols containing saturated fatty acids function as bioregulators of protein kinase C in human platelets. Lapetina, E.G., Reep, B., Ganong, B.R., Bell, R.M. J. Biol. Chem. (1985) [Pubmed]
  21. Protein kinase C as a mediator of high density lipoprotein receptor-dependent efflux of intracellular cholesterol. Mendez, A.J., Oram, J.F., Bierman, E.L. J. Biol. Chem. (1991) [Pubmed]
  22. Stimulation of lipolysis and hormone-sensitive lipase via the extracellular signal-regulated kinase pathway. Greenberg, A.S., Shen, W.J., Muliro, K., Patel, S., Souza, S.C., Roth, R.A., Kraemer, F.B. J. Biol. Chem. (2001) [Pubmed]
  23. Roles of intracellular and extracellular calcium in the kinetic profile of adrenocorticotropin secretion by perifused rat anterior pituitary cells. II. Arginine vasopressin, oxytocin, and angiotensin-II stimulation. Won, J.G., Oki, Y., Orth, D.N. Endocrinology (1990) [Pubmed]
  24. Endothelin-1 and photoreleased diacylglycerol increase L-type Ca2+ current by activation of protein kinase C in rat ventricular myocytes. He, J.Q., Pi, Y., Walker, J.W., Kamp, T.J. J. Physiol. (Lond.) (2000) [Pubmed]
  25. Physiologic signaling in normal human T-cells: mRNA phenotyping by northern blot analysis and reverse transcription-polymerase chain reaction. Wieder, K.J., Walz, G., Zanker, B., Sehajpal, P., Sharma, V.K., Skolnik, E., Strom, T.B., Suthanthiran, M. Cell. Immunol. (1990) [Pubmed]
  26. CDw17: a neutrophil glycolipid antigen regulated by activation. Symington, F.W. J. Immunol. (1989) [Pubmed]
  27. Activation of protein kinase C induces neurofilament fragmentation, hyperphosphorylation of perikaryal neurofilaments and proximal dendritic swellings in cultured motor neurons. Doroudchi, M.M., Durham, H.D. J. Neuropathol. Exp. Neurol. (1996) [Pubmed]
  28. Role for PKC in the adenosine-induced decrease in shortening velocity of rat ventricular myocytes. Lester, J.W., Hofmann, P.A. Am. J. Physiol. Heart Circ. Physiol. (2000) [Pubmed]
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