Fagomine - CAS 53185-12-9
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Not Intended for Therapeutic Use. For research use only.
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Fagomine is an iminosugar originally isolated from seeds of buckwheat (Fagopyrum sculentum Moench). It presents in the human diet and is now available as a pure crystalline product.
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1.D-Fagomine attenuates metabolic alterations induced by a high-energy-dense diet in rats.
Molinar-Toribio E1, Pérez-Jiménez J, Ramos-Romero S, Gómez L, Taltavull N, Nogués MR, Adeva A, Jáuregui O, Joglar J, Clapés P, Torres JL. Food Funct. 2015 Aug;6(8):2614-9. doi: 10.1039/c5fo00591d. Epub 2015 Jul 1.
d-Fagomine is a natural iminosugar that counteracts the short-term effects of a high-energy-dense diet on body weight, fasting blood glucose levels and the proportion of gut Enterobacteriales. This suggests that supplementation with d-fagomine for longer periods may delay the onset of other factors related to metabolic syndrome. Here we evaluate the effects of d-fagomine dietary supplementation on relevant metabolic hormones and lipid peroxidation. Adult Sprague-Dawley rats were fed a high-fat high-sucrose diet supplemented or not with d-fagomine (0.065% w/w) for 9 weeks. Weight gain, plasma triglycerides, glucose, insulin, glucagon, ghrelin, leptin, and urine F2-isoprostanes were evaluated. d-Fagomine attenuated the changes induced by the high-energy-dense diet in triglycerides and all the hormones tested. These results suggest that d-fagomine may help to avert the complications associated with unhealthy eating by counteracting the effects of high-energy-dense diets during the early stages of the development of metabolic disorders.
2.Effect of (D)-fagomine on excreted Enterobacteria and weight gain in rats fed a high-fat high-sucrose diet.
Ramos-Romero S1, Molinar-Toribio E, Gómez L, Pérez-Jiménez J, Casado M, Clapés P, Piña B, Torres JL. Obesity (Silver Spring). 2014 Apr;22(4):976-9. doi: 10.1002/oby.20640. Epub 2013 Dec 4.
OBJECTIVE: Becoming overweight has been related to elevated levels of Enterobacteriales in the gut. d-Fagomine is an iminosugar that has been shown to selectively agglutinate Enterobacteriales in vitro. The goal of this work is to establish whether d-fagomine exerts a similar effect in vivo and whether this has any downstream consequences on weight gain.
3.A concise synthesis of N-substituted fagomine derivatives and the systematic exploration of their α-glycosidase inhibition.
Jiang FX1, Liu QZ1, Zhao D2, Luo CT1, Guo CP1, Ye WC3, Luo C2, Chen H4. Eur J Med Chem. 2014 Apr 22;77:211-22. doi: 10.1016/j.ejmech.2014.03.004. Epub 2014 Mar 3.
A novel and concise scheme has been developed successfully for the syntheses of N-substituted fagomine derivatives. The transformation of lactone (2) to 1,5-diol (3) was carried on with high yield (93-95%). The cyclization of 4 to 5 is a high stereoselective reaction (de value > 98%). It is disclosed that bulky substituent at N atom of the piperidine decreases the inhibition activity except those substituents having the ability of solvation or forming disulfide bond with M444 at the active site of α-glycosidase, which enhance the interaction with enzyme. Compounds with S-configuration at C-3 show greater activity than those with R-configuration. The structure-activity relationship study is also supported by molecular docking analysis.
4.Asymmetric syntheses of (-)-3-epi-Fagomine, (2R,3S,4R)-dihydroxypipecolic acid, and several polyhydroxylated homopipecolic acids.
Csatayová K1, Davies SG, Fletcher AM, Ford JG, Klauber DJ, Roberts PM, Thomson JE. J Org Chem. 2014 Nov 21;79(22):10932-44. doi: 10.1021/jo501952t. Epub 2014 Oct 30.
A range of enantiopure polyhydroxylated piperidines, including (2R,3S,4R)-dihydroxypipecolic acid, (-)-3-epi-fagomine, (2S,3S,4R)-dihydroxyhomopipecolic acid, (2S,3R,4R)-dihydroxyhomopipecolic acid, and two trihydroxy-substituted homopipecolic acids, have been prepared using diastereoselective olefinic oxidations of a range of enantiopure tetrahydropyridines as the key step. The requisite substrates were readily prepared from tert-butyl sorbate using our diastereoselective hydroamination or aminohydroxylation protocols followed by ring-closing metathesis. After diastereoselective olefinic oxidation of the resultant enantiopure tetrahydropyridines and deprotection, enantiopure polyhydroxylated piperidines were isolated as single diastereoisomers (>99:1 dr) in good overall yield.
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CAS 53185-12-9 Fagomine

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