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Chemical Compound Review

Triolein     2,3-bis[[(Z)-octadec-9- enoyl]oxy]propyl...

Synonyms: Raoline, Olein, tri-Olein, Kaolube 190, AC1NUZLF, ...
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Disease relevance of Triolein


High impact information on Triolein


Chemical compound and disease context of Triolein


Biological context of Triolein

  • Thus, triolein is present in the bilayer in an orientation appropriate for enzymatic hydrolysis, with the second substrate (H2O) in close proximity to the hydrolytic site, and with a conformation that could explain, in part, enzymatic specificity for hydrolysis at the alpha position [13].
  • Similar kinetics has earlier been reported using phospholipid-emulsified triolein droplets (Borgström, B. (1980) Gastroenterology 78, 954-962) [14].
  • Enzyme activity was enhanced, 2.5-fold against trioleoylglycerol, concomitant with phosphorylation, with half-maximal effect within 30 sec, a rate of phosphorylation of the enzyme comparable to that obtained in vivo (Nilsson, N. O., Strålfors, P., Fredrikson, G., and Belfrage, P. (1980) FEBS Lett. 111, 125-130) [15].
  • To understand how apoA-I behaves at hydrophobic lipoprotein interfaces, the interfacial properties of apoA-I and an amphipathic alpha-helical consensus sequence peptide (CSP) were studied at the triolein/water (TO/W) interface [16].
  • Substrate specificity studies showed that ES-10 is also able to catalyze hydrolysis of triolein [17].

Anatomical context of Triolein


Associations of Triolein with other chemical compounds

  • Trypsin, chymotrypsin, lipolytic, lipase, and colipase activities were measured in fresh undiluted or diluted (1:4 and 1:16 with saline and T-tube bile) duodenal juice as well as after adding CaCl2, casein, triolein, or a chymotrypsin inhibitor [6].
  • Cosonicated mixtures of egg phosphatidylcholine and small amounts (less than 5% wt/wt) of triolein have been studied by 13C NMR spectroscopy [13].
  • Liposomes prepared from egg-yolk PC alone did not induce macrophage growth, but those prepared from mixtures of egg-yolk PC and cholesterol or cholesteryl esters other than cholesteryl oleate, or triglycerides other than triolein, enhanced 3H-TdR incorporation into macrophages [23].
  • No activity was found with any denatured PHA, oligomers of (R)-3HB with five or less 3HB units, poly(6-hydroxyhexanoate), substrates of lipases such as tributyrin or triolein, substrates for amidases/nitrilases, DNA, RNA, casein, N-alpha-benzoyl-l-arginine-4-nitranilide, or starch [24].
  • Lipolysis reactions were carried out on synthetic trioctanoin or triolein, which are homogenous, prochiral triglycerides, chosen as models for physiological lipase substrates [25].

Gene context of Triolein

  • In contrast, chimeric HL containing the LPL lid was more active against triolein (123% of the wild type) and less active against DOPC (23, 0, and 30%, respectively) than normal HL [26].
  • In contrast, dietary 18:1(n-9), i.e. triolein, had no inhibitory influence on the expression of SREBP-1 or FAS [27].
  • Fat malabsorption, assessed by the triolein breath test, was more common among patients with increased motilin and PYY [28].
  • The pH profile of human white adipose tissue triolein hydrolase activity was identical to that of HSL but differed from the ATGL profile [29].
  • The rates of LpL-catalyzed hydrolysis of trioleoylglycerol and DPPC were determined at pH 7.4 and 8.5 in the presence and absence of apoC-II [30].

Analytical, diagnostic and therapeutic context of Triolein


  1. Triolein breath test: a sensitive and specific test for fat malabsorption. Newcomer, A.D., Hofmann, A.F., DiMagno, E.P., Thomas, P.J., Carlson, G.L. Gastroenterology (1979) [Pubmed]
  2. Two-stage triolein breath test differentiates pancreatic insufficiency from other causes of malabsorption. Goff, J.S. Gastroenterology (1982) [Pubmed]
  3. Pulmonary neutral fat embolism in dogs. Jacobovitz-Derks, D., Derks, C.M. Am. J. Pathol. (1979) [Pubmed]
  4. Cloning and characterization of the acid lipase from castor beans. Eastmond, P.J. J. Biol. Chem. (2004) [Pubmed]
  5. Genetic control of macrophage functions. I. Polygenic regulation of phagocytosis stimulation produced by Glyceryl Trioleate. Mouton, D., Bouthillier, Y., Feingold, N., Feingold, J., Decreusefond, C., Stiffel, C., Biozzi, G. J. Exp. Med. (1975) [Pubmed]
  6. How to protect human pancreatic enzyme activities in frozen duodenal juice. Kelly, D.G., Sternby, B., DiMagno, E.P. Gastroenterology (1991) [Pubmed]
  7. Mechanism of increase in steatorrhea with calcium and magnesium in exocrine pancreatic insufficiency: an animal model. Graham, D.Y., Sackman, J.W. Gastroenterology (1982) [Pubmed]
  8. Diagnosis and differentiation of fat malabsorption in children using 13C-labeled lipids: trioctanoin, triolein, and palmitic acid breath tests. Watkins, J.B., Klein, P.D., Schoeller, D.A., Kirschner, B.S., Park, R., Perman, J.A. Gastroenterology (1982) [Pubmed]
  9. Inhibition of purified human postheparin lipoprotein lipase by beta-adrenergic blockers in vitro. Kihara, S., Kubo, M., Ikeda, N., Yokoyama, S., Matsuzawa, Y., Tarui, S., Yamamoto, A., Hostetler, K.Y. Biochem. Pharmacol. (1989) [Pubmed]
  10. Screening of environmental DNA libraries for the presence of genes conferring lipolytic activity on Escherichia coli. Henne, A., Schmitz, R.A., Bömeke, M., Gottschalk, G., Daniel, R. Appl. Environ. Microbiol. (2000) [Pubmed]
  11. Biodiesel production from triolein and short chain alcohols through biocatalysis. Salis, A., Pinna, M., Monduzzi, M., Solinas, V. J. Biotechnol. (2005) [Pubmed]
  12. Identification and kinetic study of tyrosinase inhibitors found in sake lees. Jeon, H.J., Noda, M., Maruyama, M., Matoba, Y., Kumagai, T., Sugiyama, M. J. Agric. Food Chem. (2006) [Pubmed]
  13. Solubilization and localization of triolein in phosphatidylcholine bilayers: a 13C NMR study. Hamilton, J.A., Small, D.M. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  14. Product activation of pancreatic lipase. Lipolytic enzymes as probes for lipid/water interfaces. Wieloch, T., Borgström, B., Piéroni, G., Pattus, F., Verger, R. J. Biol. Chem. (1982) [Pubmed]
  15. Phosphorylation of hormone-sensitive lipase by cyclic AMP-dependent protein kinase. Strålfors, P., Belfrage, P. J. Biol. Chem. (1983) [Pubmed]
  16. The interfacial properties of ApoA-I and an amphipathic alpha-helix consensus peptide of exchangeable apolipoproteins at the triolein/water interface. Wang, L., Atkinson, D., Small, D.M. J. Biol. Chem. (2005) [Pubmed]
  17. Isolation and characterization of a microsomal acid retinyl ester hydrolase. Linke, T., Dawson, H., Harrison, E.H. J. Biol. Chem. (2005) [Pubmed]
  18. Modulation of hepatic ferrochelatase activity by dietary manipulation of mitochondrial phospholipid fatty acyl groups. Kools, A.M., Straka, J.G., Hill, H.D., Whitmer, D.I., Holman, R.T., Bloomer, J.R. Hepatology (1989) [Pubmed]
  19. Effect of lipid particle size on association of apolipoproteins with lipid. Tajima, S., Yokoyama, S., Yamamoto, A. J. Biol. Chem. (1983) [Pubmed]
  20. Hepatic retinol metabolism. Distribution of retinoids, enzymes, and binding proteins in isolated rat liver cells. Blomhoff, R., Rasmussen, M., Nilsson, A., Norum, K.R., Berg, T., Blaner, W.S., Kato, M., Mertz, J.R., Goodman, D.S., Eriksson, U. J. Biol. Chem. (1985) [Pubmed]
  21. Lipoprotein biosynthesis in the larvae of the tobacco hornworm, Manduca sexta. Prasad, S.V., Fernando-Warnakulasuriya, G.J., Sumida, M., Law, J.H., Wells, M.A. J. Biol. Chem. (1986) [Pubmed]
  22. Coenzyme A-independent monoacylglycerol acyltransferase from rat intestinal mucosa. Tsujita, T., Miyazaki, T., Tabei, R., Okuda, H. J. Biol. Chem. (1996) [Pubmed]
  23. Induction of macrophage growth by lipids. Yui, S., Yamazaki, M. J. Immunol. (1986) [Pubmed]
  24. A new type of thermoalkalophilic hydrolase of Paucimonas lemoignei with high specificity for amorphous polyesters of short chain-length hydroxyalkanoic acids. Handrick, R., Reinhardt, S., Focarete, M.L., Scandola, M., Adamus, G., Kowalczuk, M., Jendrossek, D. J. Biol. Chem. (2001) [Pubmed]
  25. Stereoselectivity of lipases. II. Stereoselective hydrolysis of triglycerides by gastric and pancreatic lipases. Rogalska, E., Ransac, S., Verger, R. J. Biol. Chem. (1990) [Pubmed]
  26. Human hepatic and lipoprotein lipase: the loop covering the catalytic site mediates lipase substrate specificity. Dugi, K.A., Dichek, H.L., Santamarina-Fojo, S. J. Biol. Chem. (1995) [Pubmed]
  27. Sterol regulatory element binding protein-1 expression is suppressed by dietary polyunsaturated fatty acids. A mechanism for the coordinate suppression of lipogenic genes by polyunsaturated fats. Xu, J., Nakamura, M.T., Cho, H.P., Clarke, S.D. J. Biol. Chem. (1999) [Pubmed]
  28. Gastrointestinal regulatory peptides in systemic sclerosis. Akesson, A., Ekman, R. Arthritis Rheum. (1993) [Pubmed]
  29. Human adipose triglyceride lipase (PNPLA2) is not regulated by obesity and exhibits low in vitro triglyceride hydrolase activity. Mairal, A., Langin, D., Arner, P., Hoffstedt, J. Diabetologia (2006) [Pubmed]
  30. Lipoprotein lipase-catalyzed hydrolysis of phosphatidylcholine of guinea pig very low density lipoproteins and discoidal complexes of phospholipid and apolipoprotein: effect of apolipoprotein C-II on the catalytic mechanism. Shirai, K., Fitzharris, T.J., Shinomiya, M., Muntz, H.G., Harmony, J.A., Jackson, R.L., Quinn, D.M. J. Lipid Res. (1983) [Pubmed]
  31. Triolein breath test. Pedersen, N.T. Gastroenterology (1980) [Pubmed]
  32. Idiopathic chylopericardium: 131-I-triolein scan for noninvasive diagnosis. Savran, S.V., Ratshin, R.A., Shirley, J.H., Naguwa, S.M., Goodman, L. Ann. Intern. Med. (1975) [Pubmed]
  33. Acceleration of platelet aggregability due to modulation of native LDL. Kanazawa, T., Kaneko, H., Uemura, T., Konta, Y., Onodera, K., Metoki, H., Oike, Y. Circ. Res. (1990) [Pubmed]
  34. Cloning, expression, and fatty acid regulation of the human delta-5 desaturase. Cho, H.P., Nakamura, M., Clarke, S.D. J. Biol. Chem. (1999) [Pubmed]
  35. Evidence for a dual mechanism of lipolysis activation by epinephrine in rat adipose tissue. Wise, L.S., Jungas, R.L. J. Biol. Chem. (1978) [Pubmed]
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