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Chemical Compound Review

Monoolein     2,3-dihydroxypropyl (Z)-octadec-9-enoate

Synonyms: Olicine, Peceol, Supeol, Oleoylglycerol, mono-olein, ...
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High impact information on Adchem GMO

  • In addition, MGAT activity was proportional to the level of MGAT1 protein expressed, and the amount of diacylglycerol produced depended on the concentration of either of its substrates, oleoyl-CoA or monooleoylglycerol [1].
  • Based on the hydrolysis of specific monooleoylglycerol isomers, it was estimated that the 1(3)-ester bonds of the acylglycerols were hydrolyzed 3- to 4-fold faster than the 2-ester bonds [2].
  • 4. This protein was further purified by hydrophobic chromatography on ethyl agarose; it was eluted with a micellar solution of sodium taurodeoxycholate, oleic acid, and monooleoylglycerol at pH 6 [3].
  • Monooleoylglycerol caused a decrease in fluorescence from tryptophan-214 when measured at 350 nm while oleic acid had no effect on fluorescence at this wavelength and did not compete with monooleoylglycerol [4].
  • The concentration-dependence of MAGL activity with monooleoylglycerol, the preferred substrate showed kinetics typical of an interfacial lipolytic enzyme displaying optimal activity on emulsified substrate particles; apparent Km values were 0.27 mM and 0.49 mM for the sn-1(3)- and sn-2-isomers respectively [5].

Biological context of Adchem GMO


Anatomical context of Adchem GMO

  • Temperature-dependent structural changes in planar bilayer membranes formed from glycerol monooleate (GMO) dispersed in various n-alkane solvents (C12-C17) have been studied using precise measurements of specific geometric capacitance (Cg) [8].
  • Influence of monooleoylglycerol on islet cell phosphoinositide hydrolysis and insulin secretion [9].
  • It was calculated that the esterases account for approx. 2/3 of the monooleoylglycerol hydrolase activity in epithelial cells [10].
  • The carboxylesterase (carboxylic-ester hydrolase, EC and monoacylglycerol lipase (glycerol-monoester acylhydrolase, EC activities, measured against ethyl butyrate and emulsified monooleoylglycerol respectively, were determined for chicken liver microsomes and highly purified chicken liver carboxylesterase [11].
  • A significant lower mdr-1 mRNA and PGP protein expression within Caco-2 cells was observed following 1 and 7 days treatment with Peceol 0.1% to 1.0% (v/v) compared to nontreated controls [12].

Associations of Adchem GMO with other chemical compounds


Gene context of Adchem GMO

  • Presence of double bond in acyl chain, as exemplified by monooleoylglycerol or mono-11-eicosenoin, further enhanced the conversion by GPI-PLD [18].
  • Activity was low with the 1(3)- and sn-2-ether analogs of monooleoylglycerol, supporting the conclusion that the cells express the hepatic isoenzyme of MGAT [19].
  • PURPOSE: To study the effects of two lipid excipients, Peceol and Gelucire 44/14 on the in vitro pancreatic lipase activity [20].
  • It was found that TAG molecules with very short acyl chains (triacetin) can hydrate the head groups of the lipid and do not affect the critical packing parameter (CPP) of the amphiphile; therefore, they do not affect the self-assembly of the GMO in water, and the mesophase remains lamellar or cubic [17].

Analytical, diagnostic and therapeutic context of Adchem GMO


  1. Identification of a gene encoding MGAT1, a monoacylglycerol acyltransferase. Yen, C.L., Stone, S.J., Cases, S., Zhou, P., Farese, R.V. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  2. Positional specificity of hormone-sensitive lipase from rat adipose tissue. Fredrikson, G., Belfrage, P. J. Biol. Chem. (1983) [Pubmed]
  3. Purification and characterization of rat lingual lipase. Field, R.B., Scow, R.O. J. Biol. Chem. (1983) [Pubmed]
  4. Monoacylglycerol binding to human serum albumin: evidence that monooleoylglycerol binds at the dansylsarcosine site. Thumser, A.E., Buckland, A.G., Wilton, D.C. J. Lipid Res. (1998) [Pubmed]
  5. Purification and properties of a monoacylglycerol lipase in human erythrocytes. Somma-Delpéro, C., Valette, A., Lepetit-Thévenin, J., Nobili, O., Boyer, J., Vérine, A. Biochem. J. (1995) [Pubmed]
  6. Membrane proteins in human erythrocytes during cell fusion induced by oleoylglycerol. Quirk, S.J., Ahkong, Q.F., Botham, G.M., Vos, J., Lucy, J.A. Biochem. J. (1978) [Pubmed]
  7. Lipid-based delivery systems for improving the bioavailability and lymphatic transport of a poorly water-soluble LTB4 inhibitor. Hauss, D.J., Fogal, S.E., Ficorilli, J.V., Price, C.A., Roy, T., Jayaraj, A.A., Keirns, J.J. Journal of pharmaceutical sciences. (1998) [Pubmed]
  8. Phase transitions in planar bilayer membranes. White, S.H. Biophys. J. (1975) [Pubmed]
  9. Influence of monooleoylglycerol on islet cell phosphoinositide hydrolysis and insulin secretion. Zawalich, W.S., Zawalich, K.C. Mol. Cell. Endocrinol. (1990) [Pubmed]
  10. Partial purification and properties of monoacylglycerol lipase and two esterases from isolated rat small intestinal epithelial cells. De Jong, B.J., Kalkman, C., Hülsmann, W.C. Biochim. Biophys. Acta (1978) [Pubmed]
  11. The relationship between the carboxylesterase and monoacylglycerol lipase activities of chicken liver microsomes. Keough, D.T., de Jersey, J., Zerner, B. Biochim. Biophys. Acta (1985) [Pubmed]
  12. Potential mechanisms by which Peceol increases the gastrointestinal absorption of amphotericin B. Risovic, V., Sachs-Barrable, K., Boyd, M., Wasan, K.M. Drug development and industrial pharmacy. (2004) [Pubmed]
  13. Hydrolysis of tri- and monoacylglycerol by lipoprotein lipase: evidence for a common active site. Twu, J.S., Nilsson-Ehle, P., Schotz, M.C. Biochemistry (1976) [Pubmed]
  14. Solubilization of ubiquinone-10 in the lamellar and bicontinuous cubic phases of aqueous monoolein. Barauskas, J., Razumas, V., Nylander, T. Chem. Phys. Lipids (1999) [Pubmed]
  15. Influence of staurosporine, nitrendipine and monooleoylglycerol on interleukin-1-induced insulin secretion and phosphoinositide hydrolysis. Zawalich, W.S., Zawalich, K.C. Mol. Cell. Endocrinol. (1991) [Pubmed]
  16. Enhanced lutein bioavailability by lyso-phosphatidylcholine in rats. Lakshminarayana, R., Raju, M., Krishnakantha, T.P., Baskaran, V. Mol. Cell. Biochem. (2006) [Pubmed]
  17. Transitions induced by solubilized fat into reverse hexagonal mesophases. Amar-Yuli, I., Garti, N. Colloids and surfaces. B, Biointerfaces. (2005) [Pubmed]
  18. Regulation of brain glycosylphosphatidylinositol-specific phospholipase D by natural amphiphiles. Lee, J.Y., Lee, H.J., Kim, M.R., Myung, P.K., Sok, D.E. Neurochem. Res. (1999) [Pubmed]
  19. Hepatic monoacylglycerol acyltransferase activity in HA1 and HA7 hepatoma/hepatocyte hybrid cells: regulation by insulin and dexamethasone and by cell density. Coleman, R.A. Biochim. Biophys. Acta (1993) [Pubmed]
  20. Effect of lipid excipients on in vitro pancreatic lipase activity. Subramanian, R., Wasan, K.M. Drug development and industrial pharmacy. (2003) [Pubmed]
  21. Fourier-transform infrared spectroscopy study of dioleoylphosphatidylcholine and monooleoylglycerol in lamellar and cubic liquid crystals. Nilsson, A., Holmgren, A., Lindblom, G. Biochemistry (1991) [Pubmed]
  22. Are monoglyceride-lipase, triglyceride-lipase and phospholipase A of rat liver microsomes distinct protein entities? Colbeau, A., Ngo-Tri, H., Chabert, J., Vignais, P.M. Biochimie (1977) [Pubmed]
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