| 词条 | Mannoheptulose |
| 释义 |
| Watchedfields = changed | verifiedrevid = 443934920 | Name = D-Mannoheptulose | ImageFile = Mannoheptulose.svg | ImageSize = 200px | IUPACName = D-Manno-hept-2-ulose | OtherNames = |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo = 3615-44-9 | PubChem = 12600 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 12080 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = HSNZZMHEPUFJNZ-QMTIVRBISA-N | SMILES = O=C([C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO)CO | 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 |Section2={{Chembox Properties | C=7 | H=14 | O=7 | Appearance = | Density = 1.7 g cm−3 | MeltingPt = | BoilingPt = | Solubility = |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }}Mannoheptulose is a heptose, a monosaccharide with seven carbon atoms, and a ketose, with the characteristic carbonyl group of the carbohydrate present on a secondary carbon (functioning as a ketone group). The sugar alcohol form of mannoheptulose is known as perseitol.[1] Inhibition of hexokinasesMannoheptulose is a competitive and non-competitive inhibitor of both hexokinase and the related liver isozyme glucokinase.[2] [3][4] By blocking the enzyme hexokinase, it prevents glucose phosphorylation, the first step in the fundamental biochemical pathway of glycolysis. As a result, the breakdown of glucose is inhibited. Because of its inhibition of glycolysis in vitro, it has been investigated as a novel nutraceuticals for weight management for dogs.[5][6] However, while mannoheptulose is suggested to affect the energy balance of adult dogs, independent of dosage and physical activity, research disagrees whether it significantly alters energy expenditure in dogs. Inhibition of insulin secretionMannoheptulose has been reported to inhibit insulin secretion from pancreas.[7] 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. Natural occurrenceMannoheptulose is naturally occurring in alfalfa,[1] avocados.[8][1] fig,[1] and the primrose.[1] Heptoses can make up over a tenth of the tissue dry weight of the avocado tree.[1] Though the carbohydrate is thought to be produced during photosynthesis[8] the precise biological pathway for the synthesis of mannoheptulose was unknown as of 2002.[1] Like other sugars it is transported in the phloem.[8][1] References1. ^1 2 3 4 5 6 7 {{cite journal |last1=Liu |first1=Xuan |last2=Sievert |first2=James |last3=Arpaia |first3=Mary Lu |last4=Madore |first4=Monica A. |title=Postulated Physiological Roles of the Seven-carbon Sugars, Mannoheptulose, and Perseitol in Avocado |journal=Journal of the American Society for Horticultural Science |date=2002-01-01 |volume=127 |issue=1 |pages=108–114 |url=http://journal.ashspublications.org/content/127/1/108.abstract |accessdate=2018-06-26 |language=en |doi=10.21273/JASHS.127.1.108 }} {{Carbohydrates}}2. ^{{cite journal | author1=Sir Philip John Randle |author2=Haldane "Hal" G. Coore |authorlink1=Philip Randle |title=Inhibition of glucose phosphorylation by mannoheptulose |journal=Biochemical Journal |date=1 April 1964 |volume=91 |issue=1 |pages=56–59 |doi=10.1042/bj0910056 |pmid=5319361 |language=English |pmc=1202814}} 3. ^{{cite journal | author1=Olivier Scruel |author2=Chantal Vanhoutte |author3=Abdullah Sener |author4=Willy Jean Malaisse |title=Interference of D-mannoheptulose with D-glucose phosphorylation, metabolism and functional effects: Comparison between liver, parotid cells and pancreatic islets |journal=Molecular and Cellular Biochemistry |date=1998-10-01 |volume=187 |issue=1/2 |pages=113–120 |doi=10.1023/A:1006812300200 |pmid=9788748 |language=English}} 4. ^{{cite journal | last1 = Dai | first1 = N | last2 = Schaffer | first2 = A | last3 = Petreikov | first3 = M | last4 = Shahak | first4 = Y | last5 = Giller | first5 = Y | last6 = Ratner | first6 = K | last7 = Levine | first7 = A | last8 = Granot | first8 = D | title = Overexpression of Arabidopsis hexokinase in tomato plants inhibits growth, reduces photosynthesis, and induces rapid senescence | journal = The Plant Cell | volume = 11 | issue = 7 | pages = 1253–66 | year = 1999 | pmid = 10402427 | pmc = 144264 | doi=10.1105/tpc.11.7.1253}} 5. ^{{cite journal | last1 = McKnight | first1 = Leslie | last2 = Root-McCraig | first2 = Jared | last3 = Wright | first3 = David | last4 = Davenport | first4 = Gary | last5 = France | first5 = James | last6 = Shoveller | first6 = Anna Kate | title = Dietary Mannoheptulose Does Not Significantly Alter Daily Energy Expenditure in Adult Labrador Retrievers | journal = PLoS ONE | volume = 10 | issue = 12 | year = 2015 | pmc = 4684352 | doi = 10.1371/journal.pone.0143324 | pages=e0143324 | pmid=26656105}} 6. ^{{cite journal | last1 = McKnight | first1 = Leslie | last2 = Eyre | first2 = Ryan | last3 = Gooding | first3 = Margaret | last4 = Davenport | first4 = Gary | last5 = Shoveller | first5 = Anna Kate | title = Dietary Mannoheptulose Increases Fasting Serum Glucagon Like Peptide-1 and Post-Prandial Serum Ghrelin Concentrations in Adult Beagle Dogs | journal = Animals | volume = 5 | issue = 2 | year = 2015 | pmc = 4494402 | doi = 10.3390/ani5020365 | pages=442–454 | pmid=26479244}} 7. ^{{cite journal | last1 = Lucke | first1 = Christoph | last2 = Kagan | first2 = Avir | last3 = Adelman | first3 = Neil | last4 = Glick | first4 = Seymour | title = Effect of 2-Deoxy-D-Glucose and Mannoheptulose on the Insulin Response to Amino Acids in Rabbits | journal = Diabetes | volume = 21 | issue = 1 | year = 1972 | url = http://diabetes.diabetesjournals.org/content/21/1/1.short | doi = 10.2337/diab.21.1.1 | pmid = 5008084 | pages=1–5}} 8. ^1 2 {{cite journal |last1=Tesfay |first1=Samson Zeray |last2=Bertling |first2=Isa |last3=Bower |first3=John P. |editor1-last=Cowan |editor1-first=Ashton Keith |title=D-mannoheptulose and perseitol in 'Hass' avocado: Metabolism in seed and mesocarp tissue |journal=South African Journal of Botany |date=March 2012 |volume=79 |pages=159–165 |doi=10.1016/j.sajb.2011.10.006 |language=English }} 1 : Ketoheptoses |
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