mannoheptulose

D-Mannoheptulose
Names
	IUPAC name D-Manno-hept-2-ulose
Identifiers
CAS Registry Number	3615-44-9
ChemSpider	12080
	InChI InChI=1S/C7H14O7/c8-1-3(10)5(12)7(14)6(13)4(11)2-9/h3,5-10,12-14H,1-2H2/t3-,5-,6-,7+/m1/s1 ; Key: HSNZZMHEPUFJNZ-QMTIVRBISA-N ; InChI=1S/C7H14O7/c8-1-3(10)5(12)7(14)6(13)4(11)2-9/h3,5-10,12-14H,1-2H2/t3-,5-,6-,7+/m1/s1 ;
Jmol-3D images	Image
PubChem	12600
	SMILES O=C([C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO)CO ;
Properties
Molecular formula	C7H14O7
Molar mass	210.18 g·mol−1
Density	1.7 g cm−3
	Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references

マンノヘプツロース

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/05/24 22:26:20」(JST)

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Mannoheptulose is a hexokinase inhibitor. It is a heptose, a monosaccharide with seven carbon atoms. By blocking the enzyme hexokinase, it prevents glucose phosphorylation. As a result, the breakdown of glucose is inhibited. It is found as D-mannoheptulose in avocados.^[1]

Mannoheptulose has been reported to inhibit insulin secretion from pancreas.^[2] This inhibition occurs because when mannoheptulose is present the glycolysis is inhibited (because there is no production of glucose-6-P) therefore no increase in ATP concentration which is required to close the KATP channel in the beta cells of the pancreas causing a diminution of calcium entry and insulin secretion.

References

^ Dai, N; Schaffer, A; Petreikov, M; Shahak, Y; Giller, Y; Ratner, K; Levine, A; Granot, D (1999). "Overexpression of Arabidopsis hexokinase in tomato plants inhibits growth, reduces photosynthesis, and induces rapid senescence". The Plant cell 11 (7): 1253–66. doi:10.1105/tpc.11.7.1253. PMC 144264. PMID 10402427.
^ Lucke, Christoph; Kagan, Avir; Adelman, Neil; Glick, Seymour (1972). "Effect of 2-Deoxy-D-Glucose and Mannoheptulose on the Insulin Response to Amino Acids in Rabbits". Diabetes 21 (1).

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English Journal

Physiological characterization of the human EndoC-βH1 β-cell line.

Gurgul-Convey E1, Kaminski MT1, Lenzen S2.
Biochemical and biophysical research communications.Biochem Biophys Res Commun.2015 Aug 14;464(1):13-9. doi: 10.1016/j.bbrc.2015.05.072. Epub 2015 May 28.
In the new human EndoC-βH1 β-cell line, a detailed analysis of the physiological characteristics was performed. This new human β-cell line expressed all target structures on the gene and protein level, which are crucial for physiological function and insulin secretion induced by glucose and other
PMID 26028562

Dietary Mannoheptulose Increases Fasting Serum Glucagon Like Peptide-1 and Post-Prandial Serum Ghrelin Concentrations in Adult Beagle Dogs.

McKnight LL1, Eyre R2, Gooding MA3, Davenport GM4, Shoveller AK5,6.
Animals : an open access journal from MDPI.Animals (Basel).2015 Jun 16;5(2):442-54. doi: 10.3390/ani5020365.
There is a growing interest in the use of nutraceuticals for weight management in companion animals. The purpose of this study was to determine the effects of mannoheptulose (MH), a sugar in avocados that inhibits glycolysis, on energy metabolism in adult Beagle dogs. The study was a double-blind, r
PMID 26479244

Antioxidant compounds in the seaweed Gelidiella acerosa protects human Peripheral Blood Mononuclear Cells against TCDD induced toxicity.

Ilavarasi K1, Chermakani P, Arif Nisha S, Sheeja Malar D, Pandima Devi K.
Drug and chemical toxicology.Drug Chem Toxicol.2015 Apr;38(2):133-44. doi: 10.3109/01480545.2014.919582. Epub 2014 May 21.
2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) is a persistent environmental toxin formed as an unintentional by-product of incomplete combustion. Several therapeutic approaches have evolved to combat its toxicity since it elicits immunotoxicity, neurotoxicity, hepatotoxicity, carcinogenicity and lethal
PMID 24844840

Japanese Journal

Effect of 3-O-Methylglucose on Insulin Secretion in the Perfused Dog and Rat Pancreas

LINDSKOG Stefan,HERMANSEN Kjeld,AHREN Bo
Pancreas 16(4), 511-514, 1998-05-01
NAID 10016409184

Involvement of Blood Glucose in the Dimethylthiourea-Induced Protection against Alloxan-Induced Diabetes.

Masukawa Tohru,Nakanishi Kunio
The Japanese Journal of Pharmacology 66(1), 159-161, 1994
… Mannoheptulose, an antagonist of glucose action at pancreatic β-cells, when given 24 min after DMTU and 6 min before alloxan, eliminated the DMTU-induced protection. …
NAID 130000840656

Protection against Alloxan-Induced Diabetes by Diethyldithiocarbamate and Disulfiram in Mice.

Masukawa Tohru,Nakanishi Kunio
The Japanese Journal of Pharmacology 64(3), 141-146, 1994
… Mannoheptulose, an antagonist of glucose action at pancreatic β-cells, when given 24 min after DEDC and 6 min before alloxan, eliminated the DEDC-induced protection. …
NAID 130000840513

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[1] Dai, N; Schaffer, A; Petreikov, M; Shahak, Y; Giller, Y; Ratner, K; Levine, A; Granot, D (1999). "Overexpression of Arabidopsis hexokinase in tomato plants inhibits growth, reduces photosynthesis, and induces rapid senescence". The Plant cell 11 (7): 1253–66. doi:10.1105/tpc.11.7.1253. PMC 144264. PMID 10402427.

[2] Lucke, Christoph; Kagan, Avir; Adelman, Neil; Glick, Seymour (1972). "Effect of 2-Deoxy-D-Glucose and Mannoheptulose on the Insulin Response to Amino Acids in Rabbits". Diabetes 21 (1).

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