Mannoheptulose (BioDeep_00000397361)

Main id: BioDeep_00000020710

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(3S,4S,5R,6R)-1,3,4,5,6,7-hexahydroxyheptan-2-one

化学式: C7H14O7 (210.0739494)
中文名称: D-甘露庚酮糖, 甘露庚酮糖, D-甘露糖-2-庚糖
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C(C(C(C(C(C(=O)CO)O)O)O)O)O
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

描述信息

D-keto-manno-heptulose is the open chain form of D-manno-heptulose.
D-Mannoheptulose is a natural product found in Papaver somniferum with data available.
A 7-carbon keto sugar having the mannose configuration.
D-Mannoheptulose is a major non-structural carbohydrate in avocado. D-mannoheptulose is a specific inhibitor of D-glucose phosphorylation. D-Mannoheptulose can block insulin release and utilization of carbohydrate in rat[1][2][3].
D-Mannoheptulose is a major non-structural carbohydrate in avocado. D-mannoheptulose is a specific inhibitor of D-glucose phosphorylation. D-Mannoheptulose can block insulin release and utilization of carbohydrate in rat[1][2][3].

同义名列表

18 个代谢物同义名

(3S,4S,5R,6R)-1,3,4,5,6,7-hexahydroxyheptan-2-one; D-MANNO-HEPTULOSE [MI]; D-keto-manno-heptulose; MANNOHEPTULOSE, (+)-; D-manno-ketoheptose; D-manno-2-Heptulose; Mannoheptulose, D-; (+)-Mannoheptulose; D-manno-Heptulose; manno-2-Heptulose; D-Mannoheptulose; Mannoketoheptose; UNII-W19YH62373; Mannoheptulose; W19YH62373; AI3-61577; alpha-D-Mannoheptulopyranose; D-manno-2-Heptulose



数据库引用编号

12 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

14 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Donald K Ingram, Paul J Pistell, Zhong Q Wang, Yongmei Yu, Stefan Massimino, Gary M Davenport, Michael Hayek, George S Roth. Characterization and Mechanisms of Action of Avocado Extract Enriched in Mannoheptulose as a Candidate Calorie Restriction Mimetic. Journal of agricultural and food chemistry. 2021 Jul; 69(26):7367-7376. doi: 10.1021/acs.jafc.1c01995. [PMID: 34170139]
  • L L McKnight, J France, D Wright, G Davenport, A K Shoveller. Dietary mannoheptulose does not alter glucose or lipid metabolism in adult Labrador Retrievers. Journal of animal physiology and animal nutrition. 2018 Feb; 102(1):e122-e131. doi: 10.1111/jpn.12713. [PMID: 28444793]
  • Hiroki Teraoku, Sigurd Lenzen. Dynamics of Insulin Secretion from EndoC-βH1 β-Cell Pseudoislets in Response to Glucose and Other Nutrient and Nonnutrient Secretagogues. Journal of diabetes research. 2017; 2017(?):2309630. doi: 10.1155/2017/2309630. [PMID: 29201919]
  • Sayuan Liang, Karim Louchami, Hauke Kolster, Anna Jacobsen, Ying Zhang, Julian Thimm, Abdullah Sener, Joachim Thiem, Willy Malaisse, Tom Dresselaers, Uwe Himmelreich. In vivo and ex vivo 19-fluorine magnetic resonance imaging and spectroscopy of beta-cells and pancreatic islets using GLUT-2 specific contrast agents. Contrast media & molecular imaging. 2016 11; 11(6):506-513. doi: 10.1002/cmmi.1712. [PMID: 27624753]
  • Hyun-Woo Ju, Eun-Ji Koh, Sun-Hee Kim, Kang-Il Kim, Hojoung Lee, Suk-Whan Hong. Glucosamine causes overproduction of reactive oxygen species, leading to repression of hypocotyl elongation through a hexokinase-mediated mechanism in Arabidopsis. Journal of plant physiology. 2009 Jan; 166(2):203-12. doi: 10.1016/j.jplph.2008.04.001. [PMID: 18541338]
  • M M Wamelink, D E Smith, E E Jansen, N M Verhoeven, E A Struys, C Jakobs. Detection of transaldolase deficiency by quantification of novel seven-carbon chain carbohydrate biomarkers in urine. Journal of inherited metabolic disease. 2007 Oct; 30(5):735-42. doi: 10.1007/s10545-007-0590-2. [PMID: 17603756]
  • Nathalie Kappler-Tanudyaya, Heike Schmitt, Nils Tippkötter, Lina Meyer, Sigurd Lenzen, Roland Ulber. Combination of biotransformation and chromatography for the isolation and purification of mannoheptulose. Biotechnology journal. 2007 Jun; 2(6):692-9. doi: 10.1002/biot.200700004. [PMID: 17492712]
  • Molly T Kibenge, Catherine B Chan. The effects of high-fat diet on exercise-induced changes in metabolic parameters in Zucker fa/fa rats. Metabolism: clinical and experimental. 2002 Jun; 51(6):708-15. doi: 10.1053/meta.2002.32727. [PMID: 12037723]
  • L Crenier, P Courtois, W J Malaisse. Uptake of tritiated D-mannoheptulose by liver, pancreatic exocrine and endocrine cells. International journal of molecular medicine. 2001 Aug; 8(2):155-7. doi: 10.3892/ijmm.8.2.155. [PMID: 11445866]
  • A Sener, B Bessieres, P Courtois, L Ladriere, K Louchami, H Jijakli, W J Malaisse. Uptake of 1-deoxy-1-[125I]iodo-D-mannoheptulose by different cell types: in vitro and in vivo experiments. International journal of molecular medicine. 2001 May; 7(5):495-500. doi: 10.3892/ijmm.7.5.495. [PMID: 11295110]
  • W J Malaisse. On the track to the beta-cell. Diabetologia. 2001 Apr; 44(4):393-406. doi: 10.1007/s001250051635. [PMID: 11357468]
  • A Sener, L Ladriere, C Benito, R Gomis, F Malaisse-Lagae, W J Malaisse. D-mannoheptulose uptake and its metabolic and secretory effects in human pancreatic islets. International journal of molecular medicine. 2000 Dec; 6(6):617-20. doi: 10.3892/ijmm.6.6.617. [PMID: 11078819]
  • V Leclercq-Meyer, M M Kadiata, W J Malaisse. Effects of D-mannoheptulose and its hexaacetate ester on hormonal secretion from the perfused pancreas. International journal of molecular medicine. 2000 Aug; 6(2):143-52. doi: 10.3892/ijmm.6.2.143. [PMID: 10891557]
  • A Galina, W S da Silva. Hexokinase activity alters sugar-nucleotide formation in maize root homogenates. Phytochemistry. 2000 Jan; 53(1):29-37. doi: 10.1016/s0031-9422(99)00456-2. [PMID: 10656404]
  • J V Pego, P J Weisbeek, S C Smeekens. Mannose inhibits Arabidopsis germination via a hexokinase-mediated step. Plant physiology. 1999 Mar; 119(3):1017-23. doi: 10.1104/pp.119.3.1017. [PMID: 10069839]
  • A M Brown, D Wiggins, G F Gibbons. Glucose phosphorylation is essential for the turnover of neutral lipid and the second stage assembly of triacylglycerol-rich ApoB-containing lipoproteins in primary hepatocyte cultures. Arteriosclerosis, thrombosis, and vascular biology. 1999 Feb; 19(2):321-9. doi: 10.1161/01.atv.19.2.321. [PMID: 9974414]
  • L Ladrière, M M Kadiata, O Kirk, W J Malaisse. Stimulation by hexose esters of lactate production by rat erythrocytes: insensitivity to 3-O-methyl-D-glucose and inhibition by 2-deoxy-D-glucose and its tetraacetic ester. Molecular and cellular biochemistry. 1998 Jun; 183(1-2):175-82. doi: 10.1023/a:1006838425328. [PMID: 9655194]
  • W J Malaisse, M M Kadiata, O Scruel, A Sener. Esterification of D-mannoheptulose confers to the heptose inhibitory action on D-glucose metabolism in parotid cells. Biochemistry and molecular biology international. 1998 Mar; 44(3):625-33. doi: 10.1080/15216549800201662. [PMID: 9556224]
  • M Hulstijn, J López-Soriano, F J López-Soriano, J M Argilés. Lipogenesis in rat tissues following carbohydrate refeeding: spleen lipogenesis is modulated by insulin. Molecular and cellular biochemistry. 1997 Oct; 175(1-2):149-52. doi: 10.1023/a:1006848015161. [PMID: 9350046]
  • H Jijakli, O Kirk, W J Malaisse. Cationic and secretory effects of 6-O-acetyl-D-glucose in rat pancreatic islets. Biochemistry and molecular biology international. 1997 Oct; 43(2):233-40. doi: 10.1080/15216549700204011. [PMID: 9350330]
  • M Silverman, L Ho. Kinetic characterization of Na+/D-mannose cotransport in dog kidney: comparison with Na+/D-glucose cotransport. Biochimica et biophysica acta. 1993 Nov; 1153(1):34-42. doi: 10.1016/0005-2736(93)90273-3. [PMID: 8241248]
  • T Fushiki, A Kojima, T Imoto, K Inoue, E Sugimoto. An extract of Gymnema sylvestre leaves and purified gymnemic acid inhibits glucose-stimulated gastric inhibitory peptide secretion in rats. The Journal of nutrition. 1992 Dec; 122(12):2367-73. doi: 10.1093/jn/122.12.2367. [PMID: 1453221]
  • S Lenzen, M Mirzaie-Petri. Inhibition of aconitase by alloxan and the differential modes of protection of glucose, 3-O-methylglucose, and mannoheptulose. Naunyn-Schmiedeberg's archives of pharmacology. 1992 Nov; 346(5):532-6. doi: 10.1007/bf00169009. [PMID: 1470224]
  • J Turk, M Mueller, A Bohrer, S Ramanadham. Arachidonic acid metabolism in isolated pancreatic islets. VI. Carbohydrate insulin secretagogues must be metabolized to induce eicosanoid release. Biochimica et biophysica acta. 1992 May; 1125(3):280-91. doi: 10.1016/0005-2760(92)90057-3. [PMID: 1596516]
  • D M Hargrove, N Skrepnik, C H Lang, G J Bagby, J J Spitzer. Role of insulin in the blunted glucose metabolic response of septic rats to epinephrine. Metabolism: clinical and experimental. 1990 Nov; 39(11):1180-5. doi: 10.1016/0026-0495(90)90091-p. [PMID: 1978224]
  • J R Aprille, G Rohweder-Dunn, W A Brennan, R T Kelley, M T Nosek. Mitochondrial function after acute alteration of the endogenous insulin-to-glucagon ratio. Biochemical and biophysical research communications. 1987 Jan; 142(2):315-21. doi: 10.1016/0006-291x(87)90275-0. [PMID: 3028411]
  • M Dunlop, P A Woodman, R G Larkins. Time-course of altered islet phospholipids and of calcium binding and ionophoretic properties of islet lipids following glucose stimulation. Biochimica et biophysica acta. 1986 Aug; 860(2):376-82. doi: 10.1016/0005-2736(86)90534-1. [PMID: 3091072]
  • P C Tullson, J R Aprille. Increased adenine nucleotides in liver mitochondria after mannoheptulose injection in vivo. Archives of biochemistry and biophysics. 1986 May; 246(2):611-6. doi: 10.1016/0003-9861(86)90316-4. [PMID: 3518632]
  • L Jansson. Dissociation between pancreatic islet blood flow and insulin release in the rat. Acta physiologica Scandinavica. 1985 Jun; 124(2):223-8. doi: 10.1111/j.1748-1716.1985.tb07655.x. [PMID: 3893043]
  • R L Hanson, C M Isaacson, L D Boyajy. Stimulation of insulin secretion from isolated rat islets by SaRI 59-801. Diabetes. 1985 Jun; 34(6):548-52. doi: 10.2337/diab.34.6.548. [PMID: 3924691]
  • T Fontela, O García-Hermida, M C García-Fernández, J Gómez-Acebo. Incorporation of (U-14C)-glucose into glycogen in normal rat pancreatic islets. Revista espanola de fisiologia. 1984 Mar; 40(1):77-81. doi: NULL. [PMID: 6379781]
  • R J Wood, L H Allen. Evidence for insulin involvement in arginine- and glucose-induced hypercalciuria in the rat. The Journal of nutrition. 1983 Aug; 113(8):1561-7. doi: 10.1093/jn/113.8.1561. [PMID: 6348222]
  • L Boquist, A M Bäckman, C Strömberg. Hyperglycemia produced in mice by administration of acetazolamide and diphenylhydantoin. European journal of pharmacology. 1980 Jun; 64(4):325-32. doi: 10.1016/0014-2999(80)90240-x. [PMID: 6993214]
  • L Boquist. Effects of D-mannoheptulose on blood glucose and alloxan sensitivity in mice. Acta endocrinologica. 1980 May; 94(1):84-8. doi: 10.1530/acta.0.0940084. [PMID: 6992491]
  • A F Raonimalala, A Digaud, P Fournier. [Action of soluble carbohydrates from avocado (Persea gratissima Gaertner) fruit on utilization of calcium in the rat]. Annales de la nutrition et de l'alimentation. 1980; 34(4):735-44. doi: NULL. [PMID: 7224495]
  • L Boquist. p-Hydroxymercuribenzoate-induced hyperglycemia: influence of pre- and post-treatment with L-leucine, tolbutamide, D-mannoheptulose, insulin and alloxan. Journal of endocrinological investigation. 1979 Oct; 2(4):413-7. doi: 10.1007/bf03349342. [PMID: 395187]
  • G Klöppel, G Bommer, E Ruttmann, H J Schäfer. Qualitative and semiquantitative calcium cytochemistry in B cells of mice treated with cyproheptadine and mannoheptulose. Acta endocrinologica. 1978 Apr; 87(4):786-98. doi: 10.1530/acta.0.0870786. [PMID: 347854]
  • J E Eigenmann, M Francke-Mäder, J Zapf, E R Froesch. Non-suppressible insulin-like activity during acute metabolic and endocrine changes in dogs. Acta endocrinologica. 1977 Jul; 85(3):571-8. doi: 10.1530/acta.0.0850571. [PMID: 577341]
  • C W Schauberger, R L Thies, L J Fischer. Mechanism of protection from alloxan diabetes provided by n-butanol. The Journal of pharmacology and experimental therapeutics. 1977 May; 201(2):450-5. doi: . [PMID: 323464]
  • O P Ganda, A A Rossini, A A Like. Studies on streptozotocin diabetes. Diabetes. 1976 Jul; 25(7):595-603. doi: 10.2337/diab.25.7.595. [PMID: 132382]
  • S J Ashcroft, J R Crossley, P C Crossley. The effect of N-acylglucosamines on the biosynthesis and secretion of insulin in the rat. The Biochemical journal. 1976 Mar; 154(3):701-7. doi: 10.1042/bj1540701. [PMID: 782447]
  • G J Klain, A W Meikle, T P O'Barr. Gluconeogenic response to mannoheptulose in the rat. The Journal of nutrition. 1976 Jan; 106(1):68-72. doi: 10.1093/jn/106.1.68. [PMID: 173818]
  • C J Smith, L L Baranowski-Kish. The response of chickens to D-mannoheptulose: feeding behavior and blood glucose. Poultry science. 1976 Jan; 55(1):444-7. doi: 10.3382/ps.0550444. [PMID: 935007]
  • C Berne. The metabolism of lipids in mouse pancreatic islets. The biosynthesis of triacylglycerols and phospholipids. The Biochemical journal. 1975 Dec; 152(3):667-73. doi: 10.1042/bj1520667. [PMID: 819002]
  • S J Ashcroft, J R Crossley. The effects of glucose, N-acetylglucosamine, glyceraldehyde and other sugars on insulin release in vivo. Diabetologia. 1975 Aug; 11(4):279-84. doi: 10.1007/bf00422392. [PMID: 1205021]
  • K Doi. [Studies on the mechanism of the diabetogenic activity of streptozotocin and on the ability of compounds to block the diabetogenic activity of streptozotocin (author's transl)]. Nihon Naibunpi Gakkai zasshi. 1975 Mar; 51(3):129-47. doi: 10.1507/endocrine1927.51.3_129. [PMID: 169168]