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Chemical Compound Review

CHEBI:28657     (2S,3S,4S,5S,6R)-2,6- bis(hydroxymethyl)oxa...

Synonyms: AC1L9B4P, C08236, alpha-D-Mannoheptulopyranose, alpha-D-manno-hept-2-ulopyranose
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Disease relevance of MANNOHEPTULOSE

  • The potential of the naturally occurring sugar, mannoheptulose (which is purified from avocados and is assumed to be of low toxicity), as a cancer treatment is discussed [1].
  • After acute pancreatectomy (P) or mannoheptulose treatment [0.14 mmole per 100 gm body weight (Group M)], similar cholestatic effects were observed (-0.29 and -0.27 microliter per min per gm liver, respectively) [2].
  • Since administration of mannoheptulose induces temporary hyperglycemia, the present study was conducted to elucidate this phenomenon [3].
  • The presence of defective regulation of the glycolytic pathway by mannoheptulose in suckling and weanling rats may contribute to development of hyperinsulinemia in fa/fa rats [4].
  • Administration of mannoheptulose partially protected mice infected with Listeria monocytogenes against the lethal effect of a subsequent endotoxin challenge [5].

High impact information on MANNOHEPTULOSE

  • Because mannoheptulose, a specific HK inhibitor, blocks the severe repression triggered by 2-deoxyglucose and yet the phosphorylated products per se do not act as repression signals, we propose that HK may have dual functions and may act as a key sensor and signal transmitter of sugar repression in higher plants [6].
  • High Km glucose-phosphorylating (glucokinase) activities in a range of tumor cell lines and inhibition of rates of tumor growth by the specific enzyme inhibitor mannoheptulose [1].
  • Rates of growth of human tumors in experimental animals are dramatically reduced (by 65-79%) by a dose of 1.7 mg/g mannoheptulose daily for 5 days [1].
  • GKA1 increased the affinity of GK for the competitive inhibitor mannoheptulose but did not affect the affinity for the inhibitors palmitoyl-CoA and the endogenous 68-kDa regulator (GK regulatory protein [GKRP]), which bind to allosteric sites or to N-acetylglucosamine, which binds to the catalytic site [7].
  • This effect of glucose was counteracted by competitive inhibitors of glucokinase (5-thioglucose and mannoheptulose) but was unaffected by fructose analogs and may be due to changes in cell shape or conformation of the cytoskeleton that are secondary to glucose metabolism [8].

Biological context of MANNOHEPTULOSE


Anatomical context of MANNOHEPTULOSE


Associations of MANNOHEPTULOSE with other chemical compounds


Gene context of MANNOHEPTULOSE

  • (3) Mannoheptulose (5 mM) attenuated somatostatin and insulin secretion to 8.3 mM glucose, while it augmented glucagon output [15].
  • Furthermore, we show that mannoheptulose, a specific HXK inhibitor, restores germination of seeds grown in the presence of Man. We conclude that HXK is involved in the Man-mediated repression of germination of Arabidopsis seeds, possibly via energy depletion [22].
  • 4. Intramitochondrial succinyl-CoA content was lower in whole liver homogenates and in mitochondria isolated from animals treated with glucagon or mannoheptulose [23].
  • The glucokinase inhibitor mannoheptulose (20 mM) had no effect on its secretory action, while the protein kinase-C inhibitor staurosporine (20 nM) reduced secretion to MMSucc [24].
  • 6) These inhibitory effects of IL-1 were abolished if mannoheptulose was included during the 2-h incubation with 7 mM glucose plus 5.0 nM IL-1 [25].

Analytical, diagnostic and therapeutic context of MANNOHEPTULOSE


  1. High Km glucose-phosphorylating (glucokinase) activities in a range of tumor cell lines and inhibition of rates of tumor growth by the specific enzyme inhibitor mannoheptulose. Board, M., Colquhoun, A., Newsholme, E.A. Cancer Res. (1995) [Pubmed]
  2. Diabetes-induced cholestasis in the rat: possible role of hyperglycemia and hypoinsulinemia. Garcia-Marin, J.J., Villanueva, G.R., Esteller, A. Hepatology (1988) [Pubmed]
  3. Gluconeogenic response to mannoheptulose in the rat. Klain, G.J., Meikle, A.W., O'Barr, T.P. J. Nutr. (1976) [Pubmed]
  4. Identification of biochemical defects in pancreatic islets of fa/fa rats: a developmental study. Kibenge, M.T., Chan, C.B. Obes. Res. (1995) [Pubmed]
  5. Endotoxin shock and tumour necrosis factor release in mannoheptulose-treated mice. Choy, Y.M., Cheng, C.P., Luey, L.U., Loh, S.C., Fung, K.P., Lee, C.Y. Cancer Lett. (1987) [Pubmed]
  6. Sugar sensing in higher plants. Jang, J.C., Sheen, J. Plant Cell (1994) [Pubmed]
  7. Stimulation of hepatocyte glucose metabolism by novel small molecule glucokinase activators. Brocklehurst, K.J., Payne, V.A., Davies, R.A., Carroll, D., Vertigan, H.L., Wightman, H.J., Aiston, S., Waddell, I.D., Leighton, B., Coghlan, M.P., Agius, L. Diabetes (2004) [Pubmed]
  8. Subcellular localization, mobility, and kinetic activity of glucokinase in glucose-responsive insulin-secreting cells. Stubbs, M., Aiston, S., Agius, L. Diabetes (2000) [Pubmed]
  9. Stimulation of insulin secretion from isolated rat islets by SaRI 59-801. Hanson, R.L., Isaacson, C.M., Boyajy, L.D. Diabetes (1985) [Pubmed]
  10. Signals derived from glucose metabolism are required for glucose regulation of pancreatic islet GLUT2 mRNA and protein. Ferrer, J., Gomis, R., Fernández Alvarez, J., Casamitjana, R., Vilardell, E. Diabetes (1993) [Pubmed]
  11. Investigation of the mechanism by which glucose analogues cause translocation of glucokinase in hepatocytes: evidence for two glucose binding sites. Agius, L., Stubbs, M. Biochem. J. (2000) [Pubmed]
  12. Metabolism-independent sugar effects on gene transcription: the role of 3-o-methylglucose. Minn, A.H., Couto, F.M., Shalev, A. Biochemistry (2006) [Pubmed]
  13. Stimulation of the electron transport chain in mitochondria isolated from rats treated with mannoheptulose or glucagon. Brand, M.D., D'Alessandri, L., Reis, H.M., Hafner, R.P. Arch. Biochem. Biophys. (1990) [Pubmed]
  14. Choline turnover in phosphatidylcholine of pancreatic islets. Implications for CDP-choline pathway. Hoffman, J.M., Laychock, S.G. Diabetes (1988) [Pubmed]
  15. Pancreatic D-cell recognition of D-glucose: studies with D-glucose, D-glyceraldehyde, dihydroxyacetone, D-mannoheptulose, D-fructose, D-galactose, and D-ribose. Hermansen, K. Diabetes (1981) [Pubmed]
  16. Pathways of glucose regulation of monosaccharide transport in grape cells. Conde, C., Agasse, A., Glissant, D., Tavares, R., Gerós, H., Delrot, S. Plant Physiol. (2006) [Pubmed]
  17. Tissue-specific effects of starvation and refeeding on the disposal of oral [1-14C]triolein in the rat during lactation and on removal of litter. Oller do Nascimento, C.M., Williamson, D.H. Biochem. J. (1988) [Pubmed]
  18. Glucose regulates acetyl-CoA carboxylase gene expression in a pancreatic beta-cell line (INS-1). Brun, T., Roche, E., Kim, K.H., Prentki, M. J. Biol. Chem. (1993) [Pubmed]
  19. Influence of pyruvic acid methyl ester on rat pancreatic islets. Effects on insulin secretion, phosphoinositide hydrolysis, and sensitization of the beta cell. Zawalich, W.S., Zawalich, K.C. J. Biol. Chem. (1997) [Pubmed]
  20. Lactate production in pancreatic islets. Tamarit-Rodriguez, J., Idahl, L.A., Giné, E., Alcazar, O., Sehlin, J. Diabetes (1998) [Pubmed]
  21. Glucose stimulates glucagon release in single rat alpha-cells by mechanisms that mirror the stimulus-secretion coupling in beta-cells. Olsen, H.L., Theander, S., Bokvist, K., Buschard, K., Wollheim, C.B., Gromada, J. Endocrinology (2005) [Pubmed]
  22. Mannose inhibits Arabidopsis germination via a hexokinase-mediated step. Pego, J.V., Weisbeek, P.J., Smeekens, S.C. Plant Physiol. (1999) [Pubmed]
  23. Treatment of rats with glucagon or mannoheptulose increases mitochondrial 3-hydroxy-3-methylglutaryl-CoA synthase activity and decreases succinyl-CoA content in liver. Quant, P.A., Tubbs, P.K., Brand, M.D. Biochem. J. (1989) [Pubmed]
  24. Biochemical mechanisms involved in monomethyl succinate-induced insulin secretion. Zawalich, W.S., Zawalich, K.C. Endocrinology (1992) [Pubmed]
  25. Interleukin-1 alpha exerts glucose-dependent stimulatory and inhibitory effects on islet cell phosphoinositide hydrolysis and insulin secretion. Zawalich, W.S., Zawalich, K.C., Rasmussen, H. Endocrinology (1989) [Pubmed]
  26. Subcellular distribution and kinetic properties of cytosolic and non-cytosolic hexokinases in maize seedling roots: implications for hexose phosphorylation. da-Silva, W.S., Rezende, G.L., Galina, A. J. Exp. Bot. (2001) [Pubmed]
  27. Dissociation between pancreatic islet blood flow and insulin release in the rat. Jansson, L. Acta Physiol. Scand. (1985) [Pubmed]
  28. Pancreatic fate of D-[3H] mannoheptulose. Malaisse, W.J., Doherty, M., Kadiata, M.M., Ladriere, L., Malaisse-Lagae, F. Cell Biochem. Funct. (2001) [Pubmed]
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