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Chemical Compound Review

glucosamine     (3R,4R,5S,6R)-3-amino-6...

Synonyms: chitosamine, D-glucosamine, CHEMBL493287, SureCN167831, AG-B-75130, ...
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Disease relevance of glucosamine


Psychiatry related information on glucosamine


High impact information on glucosamine


Chemical compound and disease context of glucosamine


Biological context of glucosamine

  • The cells of each subpopulation differed in associative behavior measured by cell aggregation and stationary culture assays and in glycoproteins that contain glucosamine [19].
  • We also manually searched review articles, manuscripts, and supplements from rheumatology and OA journals and sought unpublished data by contacting content experts, study authors, and manufacturers of glucosamine or chondroitin [20].
  • In vivo glucosamine infusion induces insulin resistance in normoglycemic but not in hyperglycemic conscious rats [21].
  • We conclude that (a) heparin's anti-inflammatory effects are mainly mediated by blocking P- and L-selectin-initiated cell adhesion; (b) the sulfate groups at C6 on the glucosamine residues play a critical role in selectin inhibition; and (c) some non-anticoagulant forms of heparin retain anti-inflammatory activity [22].
  • METHODS: Crypt cell proliferation rate (CCPR) was measured using vincristine arrest and mucus synthesis by incorporation of radiolabeled N-acetyl glucosamine in colonoscopic biopsy specimens cultured with and without PNA [23].

Anatomical context of glucosamine

  • By the use of an M6 monoclonal antibody, which crossreacts with 20 different M protein types, and antibodies to the N-acetyl glucosamine determinant of the cell wall, we have been able to identify the M protein molecules released from the streptococcal cell wall with muralytic enzymes, particularly group C phage-associated lysin [24].
  • A faster eluting, neuraminidase-sensitive, fraction was observed on Sephadex chromatography of the trophoblast spectra when D-glucosamine was used as precursor [25].
  • B2cAMP also stimulated mucosal uptake of glucosamine into the intracellular pool and markedly enhanced specific activity of mucosa galactosyltransferase, an enzyme involved in glycoprotein synthesis [26].
  • Thy-1 and a number of other proteins are anchored to the outer hemi-leaflet of membranes by a glycolipid moiety containing ethanolamine phosphate, mannose, glucosamine, and phosphatidylinositol [27].
  • Glycolipids synthesized in a cell-free system prepared from the free-living protozoan Paramecium primaurelia and labelled with [3H]mannose and [3H]glucosamine using GDP-[3H]mannose and UDP-[3H]N-acetyl glucosamine, respectively, were identified and structurally characterized as glycosylinositol-phosphoceramides (GIP-ceramides) [28].

Associations of glucosamine with other chemical compounds


Gene context of glucosamine


Analytical, diagnostic and therapeutic context of glucosamine


  1. A novel role for 3-O-sulfated heparan sulfate in herpes simplex virus 1 entry. Shukla, D., Liu, J., Blaiklock, P., Shworak, N.W., Bai, X., Esko, J.D., Cohen, G.H., Eisenberg, R.J., Rosenberg, R.D., Spear, P.G. Cell (1999) [Pubmed]
  2. Symbiotic host-specificity of Rhizobium meliloti is determined by a sulphated and acylated glucosamine oligosaccharide signal. Lerouge, P., Roche, P., Faucher, C., Maillet, F., Truchet, G., Promé, J.C., Dénarié, J. Nature (1990) [Pubmed]
  3. Efficacy of glucosamine and chondroitin for treatment of osteoarthritis. Donohoe, M. JAMA (2000) [Pubmed]
  4. Hyperglycemia inhibits endothelial nitric oxide synthase activity by posttranslational modification at the Akt site. Du, X.L., Edelstein, D., Dimmeler, S., Ju, Q., Sui, C., Brownlee, M. J. Clin. Invest. (2001) [Pubmed]
  5. Glucosamine induces insulin resistance in vivo by affecting GLUT 4 translocation in skeletal muscle. Implications for glucose toxicity. Baron, A.D., Zhu, J.S., Zhu, J.H., Weldon, H., Maianu, L., Garvey, W.T. J. Clin. Invest. (1995) [Pubmed]
  6. Cultured fibroblasts in Huntington's disease. II. Effects of glucosamine. Archer, F.J., Mancall, E.L. Arch. Neurol. (1983) [Pubmed]
  7. Differential mechanisms of feeding modulation induced by amino sugars in rats. Okabe, Y., Sakata, T., Fujimoto, K., Kurata, K., Yoshimatsu, H., Ueda, K. Proc. Soc. Exp. Biol. Med. (1988) [Pubmed]
  8. Prevalence of and factors associated with glucosamine use in Canada. Hopman, W.M., Towheed, T.E., Gao, Y., Berger, C., Joseph, L., Vik, S.A., Hanley, D.A., Carran, J., Anastassiades, T. Osteoarthr. Cartil. (2006) [Pubmed]
  9. Development of a simple analytical methodology for determination of glucosamine release from modified release matrix tablets. Wu, Y., Hussain, M., Fassihi, R. Journal of pharmaceutical and biomedical analysis. (2005) [Pubmed]
  10. Comparative structural studies of urinary glycosaminoglycans in the Hurler and Hunter syndromes. Ramage, P., Cunningham, W.L. Biochim. Biophys. Acta (1975) [Pubmed]
  11. Order out of chaos: assembly of ligand binding sites in heparan sulfate. Esko, J.D., Selleck, S.B. Annu. Rev. Biochem. (2002) [Pubmed]
  12. Molecular basis of symbiotic host specificity in Rhizobium meliloti: nodH and nodPQ genes encode the sulfation of lipo-oligosaccharide signals. Roche, P., Debellé, F., Maillet, F., Lerouge, P., Faucher, C., Truchet, G., Dénarié, J., Promé, J.C. Cell (1991) [Pubmed]
  13. A nutrient-sensing pathway regulates leptin gene expression in muscle and fat. Wang, J., Liu, R., Hawkins, M., Barzilai, N., Rossetti, L. Nature (1998) [Pubmed]
  14. Genetic evidence for transmembrane acetylation by lysosomes. Bame, K.J., Rome, L.H. Science (1986) [Pubmed]
  15. The Vibrio cholerae chitin utilization program. Meibom, K.L., Li, X.B., Nielsen, A.T., Wu, C.Y., Roseman, S., Schoolnik, G.K. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  16. Loss of melanogenic properties in tyrosinases induced by glucosylation inhibitors within malignant melanoma cells. Imokawa, G., Mishima, Y. Cancer Res. (1982) [Pubmed]
  17. Gram-negative endotoxin: an extraordinary lipid with profound effects on eukaryotic signal transduction. Raetz, C.R., Ulevitch, R.J., Wright, S.D., Sibley, C.H., Ding, A., Nathan, C.F. FASEB J. (1991) [Pubmed]
  18. The inhibition of thymidine metabolism in tumor cells treated with D-glucosamine. Friedman, S.J., Trotter, C.D., Kimball, T., Skehan, P.J. Cancer Res. (1977) [Pubmed]
  19. Cells isolated from the embryonic neural retina differ in behavior in vitro and membrane structure. Sheffield, J.B., Pressman, D., Lynch, M. Science (1980) [Pubmed]
  20. Glucosamine and chondroitin for treatment of osteoarthritis: a systematic quality assessment and meta-analysis. McAlindon, T.E., LaValley, M.P., Gulin, J.P., Felson, D.T. JAMA (2000) [Pubmed]
  21. In vivo glucosamine infusion induces insulin resistance in normoglycemic but not in hyperglycemic conscious rats. Rossetti, L., Hawkins, M., Chen, W., Gindi, J., Barzilai, N. J. Clin. Invest. (1995) [Pubmed]
  22. Heparin's anti-inflammatory effects require glucosamine 6-O-sulfation and are mediated by blockade of L- and P-selectins. Wang, L., Brown, J.R., Varki, A., Esko, J.D. J. Clin. Invest. (2002) [Pubmed]
  23. Peanut lectin stimulates proliferation in colonic explants from patients with inflammatory bowel disease and colon polyps. Ryder, S.D., Parker, N., Ecclestone, D., Haqqani, M.T., Rhodes, J.M. Gastroenterology (1994) [Pubmed]
  24. Size variation of the M protein in group A streptococci. Fischetti, V.A., Jones, K.F., Scott, J.R. J. Exp. Med. (1985) [Pubmed]
  25. Increased sialylation of surface glycopeptides of human trophoblast compared with fetal cells from the same conceptus. Whyte, A., Loke, Y.W. J. Exp. Med. (1978) [Pubmed]
  26. Stimulation of colonic glycoprotein synthesis by dibutyryl cyclic AMP and theophylline. LaMont, J.T., Ventola, A. Gastroenterology (1977) [Pubmed]
  27. Dynamics and longevity of the glycolipid-anchored membrane protein, Thy-1. Lemansky, P., Fatemi, S.H., Gorican, B., Meyale, S., Rossero, R., Tartakoff, A.M. J. Cell Biol. (1990) [Pubmed]
  28. Glycosylinositol-phosphoceramide in the free-living protozoan Paramecium primaurelia: modification of core glycans by mannosyl phosphate. Azzouz, N., Striepen, B., Gerold, P., Capdeville, Y., Schwarz, R.T. EMBO J. (1995) [Pubmed]
  29. The effect of select nutrients on serum high-density lipoprotein cholesterol and apolipoprotein A-I levels. Mooradian, A.D., Haas, M.J., Wong, N.C. Endocr. Rev. (2006) [Pubmed]
  30. Sera from patients with poststreptococcal glomerulonephritis contain antibodies to glomerular heparan sulfate proteoglycan. Fillit, H., Damle, S.P., Gregory, J.D., Volin, C., Poon-King, T., Zabriskie, J. J. Exp. Med. (1985) [Pubmed]
  31. Effects of D-glucosamine and 6-azauridine on nucleotide contents, 5-fluorouridine uptake, and cytotoxicity in TA3 mammary tumor cells. Holstege, A., Keppler, D. J. Natl. Cancer Inst. (1986) [Pubmed]
  32. Effects of chronic ethanol administration on hepatic glycoprotein secretion in the rat. Sorrell, M.F., Nauss, J.M., Donohue, T.M., Tuma, D.J. Gastroenterology (1983) [Pubmed]
  33. Role of the endoplasmic reticulum in the synthesis of reserve proteins and the kinetics of their transport to protein bodies in developing pea cotyledons. Chrispeels, M.J., Higgins, T.J., Craig, S., Spencer, D. J. Cell Biol. (1982) [Pubmed]
  34. High glucose-induced transforming growth factor beta1 production is mediated by the hexosamine pathway in porcine glomerular mesangial cells. Kolm-Litty, V., Sauer, U., Nerlich, A., Lehmann, R., Schleicher, E.D. J. Clin. Invest. (1998) [Pubmed]
  35. Mannose-binding lectin recognizes peptidoglycan via the N-acetyl glucosamine moiety, and inhibits ligand-induced proinflammatory effect and promotes chemokine production by macrophages. Nadesalingam, J., Dodds, A.W., Reid, K.B., Palaniyar, N. J. Immunol. (2005) [Pubmed]
  36. Heparan sulfate synthesized by mouse embryonic stem cells deficient in NDST1 and NDST2 is 6-O-sulfated but contains no N-sulfate groups. Holmborn, K., Ledin, J., Smeds, E., Eriksson, I., Kusche-Gullberg, M., Kjellén, L. J. Biol. Chem. (2004) [Pubmed]
  37. Characterization and dynamics of O-linked glycosylation of human cytokeratin 8 and 18. Chou, C.F., Smith, A.J., Omary, M.B. J. Biol. Chem. (1992) [Pubmed]
  38. Saccharomyces cerevisiae GNA1, an essential gene encoding a novel acetyltransferase involved in UDP-N-acetylglucosamine synthesis. Mio, T., Yamada-Okabe, T., Arisawa, M., Yamada-Okabe, H. J. Biol. Chem. (1999) [Pubmed]
  39. Long-term effects of glucosamine sulphate on osteoarthritis progression: a randomised, placebo-controlled clinical trial. Reginster, J.Y., Deroisy, R., Rovati, L.C., Lee, R.L., Lejeune, E., Bruyere, O., Giacovelli, G., Henrotin, Y., Dacre, J.E., Gossett, C. Lancet (2001) [Pubmed]
  40. Polyvalent dendrimer glucosamine conjugates prevent scar tissue formation. Shaunak, S., Thomas, S., Gianasi, E., Godwin, A., Jones, E., Teo, I., Mireskandari, K., Luthert, P., Duncan, R., Patterson, S., Khaw, P., Brocchini, S. Nat. Biotechnol. (2004) [Pubmed]
  41. Uncouplers of oxidative phosphorylation promote derepression of the hexose transport system in cultures of hamster cells. Kalckar, H.M., Christopher, C.W., Ullrey, D. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
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