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Chemical Compound Review

Gulitol     (2R,3S,4S,5S)-hexane- 1,2,3,4,5,6-hexol

Synonyms: D-Gulitol, L-Glucitol, L-Sorbitol, AG-K-71750, CHEBI:28789, ...
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Disease relevance of sorbitol


Psychiatry related information on sorbitol

  • We next evaluated the effect of sorbitol treatment on five psychomotor performances tests in cirrhotic patients [5].
  • These pain thresholds did not correlate with blood or nerve glucose or sorbitol levels, but both correlated with plasma insulin level in STZ-normoglycemic rats, and low-dose insulin replacement normalized the pressure threshold without affecting blood glucose level [6].
  • Further investigation is needed to determine the pathophysiological significance of this novel finding of elevated sorbitol concentration in the CSF of patients with mood disorders [7].
  • An investigation was undertaken to determine if sorbitol catharsis enhanced the antidotal efficacy of activated charcoal [8].
  • When the reaction time was prolonged to 24 h and the crude product was acetylated, 1,2,3,4,5-penta-O-acetyl-6-deoxy-6-iodo-D-glucitol and D-glucitol hexaacetate were isolated in 50 and 26% yields, respectively [9].

High impact information on sorbitol

  • Significantly, cells expressing ERK2 with the docking motif mutation were resistant to sorbitol-induced apoptosis [10].
  • Infected and uninfected erythrocytes were then separated by a new procedure involving equilibrium density sedimentation on a Percoll gradient containing sorbitol [11].
  • RNA interference (RNAi) demonstrates that MEKK3 and the scaffold protein are required for p38 activation in response to sorbitol-induced hyperosmolarity [12].
  • Through its ability to bind actin, relocalize to Rac-containing membrane ruffles and its obligate requirement for p38 activation in response to sorbitol, we have termed this protein osmosensing scaffold for MEKK3 (OSM) [12].
  • FRET identifies a cytoplasmic complex of the MEKK3 scaffold protein that is recruited to dynamic actin structures in response to sorbitol treatment [12].

Chemical compound and disease context of sorbitol

  • By supplementing the diets with 1.0% myoinositol, the difference in nerve myoinositol in normal and diabetic rats on day 14 was abolished; on this diet the development of impaired MNCV in the diabetics was moderated or totally prevented, despite persistent hyperglycemia and elevated nerve sorbitol and fructose concentrations [13].
  • These observations suggest that insulin deficiency and hyperglycemia cause reversible paranodal swelling, and ultimately poorly reversible axo-glial dysjunction, via the myo-inositol-related (Na,K)-ATPase defect rather than by the osmotic effects of sorbitol accumulation within nerve fibers [14].
  • With moderate (serum Na 159 +/- 3 meq/liter) hypernatremia, more modest but significant increases in the concentrations of each of these osmoles except betaine and sorbitol were noted [15].
  • Osmoprotective activity for Escherichia coli in mammalian renal inner medulla and urine. Correlation of glycine and proline betaines and sorbitol with response to osmotic loads [4].
  • In streptozotocin-treated rats with varying degrees of diabetes sorbitol levels in the lens, sciatic nerve, and RBC were elevated in proportion to the degree of hyperglycemia [16].

Biological context of sorbitol


Anatomical context of sorbitol

  • To test this hypothesis we examined the association between PKC activity, (Na,K)-ATPase activity, and sorbitol, myoinositol, and InsP levels in cultured bovine retinal capillary endothelial cells, a cell type prominently involved in diabetic retinopathy [22].
  • The mean percentage of sorbitol absorbed in the small intestine was significantly higher in pure sorbitol doses than in those containing maltitol and Lycasin 80/55 (79% +/- 4% vs. 64% +/- 4% and 64% +/- 5%, mean +/- SEM) [23].
  • Hepatic vein catheterization showed that the hepatic extraction of sorbitol was always much higher than the extraction of indocyanine green; there was no evidence for extrahepatic, extrarenal sorbitol elimination [24].
  • In summary, the data demonstrate that, by the use of repeated injections of an iron sorbitol complex, it is possible to isolate a fraction highly enriched in hydrolytic enzymes (60 times over the homogenate) and in well preserved lysosomes emanating almost entirely from liver parenchymal cells [25].
  • Agents inhibiting cell surface movements at the free edges of marginal epithelial cells (cytochalasin, azide, sorbitol, low temperature) prevented adhesion of particles to these edges [26].

Associations of sorbitol with other chemical compounds


Gene context of sorbitol

  • Aldose reductase (AR2), a putative "hypertonicity stress protein" whose gene is induced by hyperosmolarity, protects renal medullary cells against the interstitial hyperosmolarity of antidiuresis by catalyzing the synthesis of millimolar concentrations of intracellular sorbitol from glucose [32].
  • Similarly, the presence of a membrane stabilizer (sorbitol) or the loss of phosphatidylinositol-specific phospholipase C (PLC1) protects Ume3p from oxidative-stress-induced degradation [33].
  • Here, we have found that ERK5 is required for mediating the survival of fibroblasts under basal conditions and in response to sorbitol treatment [34].
  • In examining the protein kinase components of mitogen-activated protein (MAP) kinase (MAPK) cascades that regulate the c-Jun N-terminal kinase (JNK) in Drosophila S2 cells, we previously found that distinct upstream kinases were involved in responses to sorbitol and lipopolysaccharide [35].
  • Sorbitol-stimulated JNK activity could be resolved into three peaks by fast protein liquid chromatography on a Mono Q column [36].

Analytical, diagnostic and therapeutic context of sorbitol


  1. Sorbitol, phosphoinositides, and sodium-potassium-ATPase in the pathogenesis of diabetic complications. Greene, D.A., Lattimer, S.A., Sima, A.A. N. Engl. J. Med. (1987) [Pubmed]
  2. Regeneration and repair of myelinated fibers in sural-nerve biopsy specimens from patients with diabetic neuropathy treated with sorbinil. Sima, A.A., Bril, V., Nathaniel, V., McEwen, T.A., Brown, M.B., Lattimer, S.A., Greene, D.A. N. Engl. J. Med. (1988) [Pubmed]
  3. The treatment of pulmonary edema in the absence of renal function. A role for sorbitol and furosemide. Anderson, C.C., Shahvari, M.B., Zimmerman, J.E. JAMA (1979) [Pubmed]
  4. Osmoprotective activity for Escherichia coli in mammalian renal inner medulla and urine. Correlation of glycine and proline betaines and sorbitol with response to osmotic loads. Chambers, S.T., Kunin, C.M. J. Clin. Invest. (1987) [Pubmed]
  5. Effect of sorbitol on psychomotor function: its use in alcoholic cirrhosis. McClain, C.J., Kromhout, J.P., Zieve, L., Duane, W.C. Arch. Intern. Med. (1981) [Pubmed]
  6. Mechanical hyperalgesia correlates with insulin deficiency in normoglycemic streptozotocin-treated rats. Romanovsky, D., Cruz, N.F., Dienel, G.A., Dobretsov, M. Neurobiol. Dis. (2006) [Pubmed]
  7. Elevated sorbitol concentration in the cerebrospinal fluid of patients with mood disorders. Regenold, W.T., Kling, M.A., Hauser, P. Psychoneuroendocrinology (2000) [Pubmed]
  8. Sorbitol catharsis does not enhance efficacy of charcoal in a simulated acetaminophen overdose. McNamara, R.M., Aaron, C.K., Gemborys, M., Davidheiser, S. Annals of emergency medicine. (1988) [Pubmed]
  9. Peracetylated 1,6-dibromo-D-glucitol as efficient precursor of 1,6-diiodo and some mono-, disubstituted and heterocyclic D-glucitol derivatives. Halila, S., Benazza, M., Demailly, G. Carbohydr. Res. (2003) [Pubmed]
  10. The PHD domain of MEKK1 acts as an E3 ubiquitin ligase and mediates ubiquitination and degradation of ERK1/2. Lu, Z., Xu, S., Joazeiro, C., Cobb, M.H., Hunter, T. Mol. Cell (2002) [Pubmed]
  11. Knob-positive and knob-negative Plasmodium falciparum differ in expression of a strain-specific malarial antigen on the surface of infected erythrocytes. Aley, S.B., Sherwood, J.A., Howard, R.J. J. Exp. Med. (1984) [Pubmed]
  12. Rac-MEKK3-MKK3 scaffolding for p38 MAPK activation during hyperosmotic shock. Uhlik, M.T., Abell, A.N., Johnson, N.L., Sun, W., Cuevas, B.D., Lobel-Rice, K.E., Horne, E.A., Dell'Acqua, M.L., Johnson, G.L. Nat. Cell Biol. (2003) [Pubmed]
  13. Effects of insulin and dietary myoinositol on impaired peripheral motor nerve conduction velocity in acute streptozotocin diabetes. Greene, D.A., De Jesus, P.V., Winegrad, A.I. J. Clin. Invest. (1975) [Pubmed]
  14. Role of sorbitol accumulation and myo-inositol depletion in paranodal swelling of large myelinated nerve fibers in the insulin-deficient spontaneously diabetic bio-breeding rat. Reversal by insulin replacement, an aldose reductase inhibitor, and myo-inositol. Greene, D.A., Chakrabarti, S., Lattimer, S.A., Sima, A.A. J. Clin. Invest. (1987) [Pubmed]
  15. Effects of hypernatremia on organic brain osmoles. Lien, Y.H., Shapiro, J.I., Chan, L. J. Clin. Invest. (1990) [Pubmed]
  16. Red blood cell sorbitol as an indicator of polyol pathway activity. Inhibition by sorbinil in insulin-dependent diabetic subjects. Malone, J.I., Leavengood, H., Peterson, M.J., O'Brien, M.M., Page, M.G., Aldinger, C.E. Diabetes (1984) [Pubmed]
  17. The linked roles of nitric oxide, aldose reductase and, (Na+,K+)-ATPase in the slowing of nerve conduction in the streptozotocin diabetic rat. Stevens, M.J., Dananberg, J., Feldman, E.L., Lattimer, S.A., Kamijo, M., Thomas, T.P., Shindo, H., Sima, A.A., Greene, D.A. J. Clin. Invest. (1994) [Pubmed]
  18. Sorbitol, osmoregulation, and the complications of diabetes. Burg, M.B., Kador, P.F. J. Clin. Invest. (1988) [Pubmed]
  19. Sorbitol dehydrogenase is a zinc enzyme. Jeffery, J., Chesters, J., Mills, C., Sadler, P.J., Jörnvall, H. EMBO J. (1984) [Pubmed]
  20. The UDP-Glc:Glycoprotein glucosyltransferase is essential for Schizosaccharomyces pombe viability under conditions of extreme endoplasmic reticulum stress. Fanchiotti, S., Fernández, F., D'Alessio, C., Parodi, A.J. J. Cell Biol. (1998) [Pubmed]
  21. Activation of protein kinase C by elevation of glucose concentration: proposal for a mechanism in the development of diabetic vascular complications. Lee, T.S., Saltsman, K.A., Ohashi, H., King, G.L. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  22. Differential regulation of protein kinase C and (Na,K)-adenosine triphosphatase activities by elevated glucose levels in retinal capillary endothelial cells. Lee, T.S., MacGregor, L.C., Fluharty, S.J., King, G.L. J. Clin. Invest. (1989) [Pubmed]
  23. Digestion and absorption in the human intestine of three sugar alcohols. Beaugerie, L., Flourié, B., Marteau, P., Pellier, P., Franchisseur, C., Rambaud, J.C. Gastroenterology (1990) [Pubmed]
  24. Steady-state extrarenal sorbitol clearance as a measure of hepatic plasma flow. Zeeh, J., Lange, H., Bosch, J., Pohl, S., Loesgen, H., Eggers, R., Navasa, M., Chesta, J., Bircher, J. Gastroenterology (1988) [Pubmed]
  25. Isolation of liver lysosomes by iron loading. Ultrastructural characterization. Glaumann, H., Jansson, H., Arborgh, B., Ericsson, J.L. J. Cell Biol. (1975) [Pubmed]
  26. Contact inhibition of phagocytosis in epithelial sheets: alterations of cell surface properties induced by cell-cell contacts. Vasiliev, J.M., Gelfand, I.M., Domnina, L.V., Zacharova, O.S., Ljubimov, A.V. Proc. Natl. Acad. Sci. U.S.A. (1975) [Pubmed]
  27. Diabetic cataracts and flavonoids. Varma, S.D., Mizuno, A., Kinoshita, J.H. Science (1977) [Pubmed]
  28. Vascular dysfunction induced by elevated glucose levels in rats is mediated by vascular endothelial growth factor. Tilton, R.G., Kawamura, T., Chang, K.C., Ido, Y., Bjercke, R.J., Stephan, C.C., Brock, T.A., Williamson, J.R. J. Clin. Invest. (1997) [Pubmed]
  29. An ABA and GA modulated gene expressed in the barley embryo encodes an aldose reductase related protein. Bartels, D., Engelhardt, K., Roncarati, R., Schneider, K., Rotter, M., Salamini, F. EMBO J. (1991) [Pubmed]
  30. Regulation of carbohydrate metabolism by 2,5-anhydro-D-mannitol. Riquelme, P.T., Wernette-Hammond, M.E., Kneer, N.M., Lardy, H.A. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  31. Modulation of renal-specific oxidoreductase/myo-inositol oxygenase by high-glucose ambience. Nayak, B., Xie, P., Akagi, S., Yang, Q., Sun, L., Wada, J., Thakur, A., Danesh, F.R., Chugh, S.S., Kanwar, Y.S. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  32. Altered aldose reductase gene regulation in cultured human retinal pigment epithelial cells. Henry, D.N., Del Monte, M., Greene, D.A., Killen, P.D. J. Clin. Invest. (1993) [Pubmed]
  33. Oxidative stress-induced destruction of the yeast C-type cyclin Ume3p requires phosphatidylinositol-specific phospholipase C and the 26S proteasome. Cooper, K.F., Mallory, M.J., Strich, R. Mol. Cell. Biol. (1999) [Pubmed]
  34. Activation of extracellular signal-regulated protein kinase 5 downregulates FasL upon osmotic stress. Wang, X., Finegan, K.G., Robinson, A.C., Knowles, L., Khosravi-Far, R., Hinchliffe, K.A., Boot-Handford, R.P., Tournier, C. Cell Death Differ. (2006) [Pubmed]
  35. Characterization of OSR1, a member of the mammalian Ste20p/germinal center kinase subfamily. Chen, W., Yazicioglu, M., Cobb, M.H. J. Biol. Chem. (2004) [Pubmed]
  36. Cellular stresses differentially activate c-Jun N-terminal protein kinases and extracellular signal-regulated protein kinases in cultured ventricular myocytes. Bogoyevitch, M.A., Ketterman, A.J., Sugden, P.H. J. Biol. Chem. (1995) [Pubmed]
  37. Characterization of specific pancreatic polypeptide receptors on basolateral membranes of the canine small intestine. Gilbert, W.R., Frank, B.H., Gavin, J.R., Gingerich, R.L. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  38. Purification of vacuoles from Neurospora crassa. Vaughn, L.E., Davis, R.H. Mol. Cell. Biol. (1981) [Pubmed]
  39. Red cell sorbitol: an indicator of diabetic control. Malone, J.I., Knox, G., Benford, S., Tedesco, T.A. Diabetes (1980) [Pubmed]
  40. Action of sorbinil in diabetic peripheral nerve. Relationship of polyol (sorbitol) pathway inhibition to a myo-inositol-mediated defect in sodium-potassium ATPase activity. Greene, D.A., Lattimer, S.A. Diabetes (1984) [Pubmed]
  41. Na+-K+-ATPase pumping activity is not directly linked to myo-inositol levels after sorbinil treatment in lenses of diabetic rats. Yeh, L.A., Rafford, C.E., Goddu, K.J., Ashton, M.A., Beyer, T.A., Hutson, N.J. Diabetes (1987) [Pubmed]
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