Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C6H13NO3 |
Molecular Weight | 147.1723 |
Optical Activity | ( + ) |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1NCC[C@@H](O)[C@@H]1O
InChI
InChIKey=YZNNBIPIQWYLDM-HSUXUTPPSA-N
InChI=1S/C6H13NO3/c8-3-4-6(10)5(9)1-2-7-4/h4-10H,1-3H2/t4-,5-,6-/m1/s1
D-Fagomine (1,2-dideoxynojirimycin) is a six-membered ring iminocyclitol that was first isolated from seeds of buckwheat (Fagopyrum sculentum Moench, Polygonaceae) and is also present in other plant sources such as mulberry (Morus Alba, Moraceae) leaves and gogi (Lycium chinense) roots. D-fagomine is present in common buckwheat-based foodstuffs in amounts ranging from 1 to 25 mg/kg or mg/L, it is stable during boiling, baking, frying and fermentation, and it is biosynthesised upon sprouting. The estimated total intake of D-fagomine resulting from a diet that includes such foodstuffs would be between 3 and 17 mg per day (mean for both genders; range from P5 to P95). In animal studies D-Fagomine lowers postprandial blood glucose. D-fagomine agglutinated Enterobacteriaceae (Escherichia coli, Salmonella enterica serovar Typhimurium), while it did not show this effect on Bifidobacterium spp. or Lactobacillus spp. D-fagomine significantly inhibited the adhesion of Enterobacteriaceae and promoted the adhesion of Lactobacillus acidophilus to intestinal mucosa. D-Fagomine did not show any effect on bacterial cell viability. D-fagomine may be used as a dietary ingredient or functional food component to reduce the health risks associated with an excessive intake of fast-digestible carbohydrates, or an excess of potentially pathogenic bacteria.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0043152 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22017795 |
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Target ID: GO:0007155 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22017795 |
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Target ID: CHEMBL3114 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22017795 |
42.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Potentiation of glucose-induced insulin secretion by fagomine, a pseudo-sugar isolated from mulberry leaves. | 1998 Nov |
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Cytotoxicity and enzymatic activity inhibition in cell lines treated with novel iminosugar derivatives. | 2010 Feb |
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Determination of D-fagomine in buckwheat and mulberry by cation exchange HPLC/ESI-Q-MS. | 2012 Feb |
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D-Fagomine lowers postprandial blood glucose and modulates bacterial adhesion. | 2012 Jun |
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The presence of D-fagomine in the human diet from buckwheat-based foodstuffs. | 2013 Feb 15 |
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Effect of (D)-fagomine on excreted Enterobacteria and weight gain in rats fed a high-fat high-sucrose diet. | 2014 Apr |
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D-Fagomine attenuates metabolic alterations induced by a high-energy-dense diet in rats. | 2015 Aug |
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Fate of d-Fagomine after Oral Administration to Rats. | 2017 Jun 7 |
Patents
Sample Use Guides
Healthy Volunteers: evaluation of the effects of D-fagomine 30-40 mg on glycaemic response to sucrose (50 g).
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.
Route of Administration:
Oral
D-fagomine (0.14 mM) agglutinated 60 % of Enterobacteriaceae (Escherichia coli, Salmonella enterica serovar Typhimurium) populations (P < 0·01), while it did not show this effect on Bifidobacterium spp. or Lactobacillus spp. At the same concentration, d-fagomine significantly (P < 0·001) inhibited the adhesion of Enterobacteriaceae (95-99 % cells in the supernatant) and promoted the adhesion of Lactobacillus acidophilus (56 % cells in the supernatant) to intestinal mucosa. D-Fagomine did not show any effect on bacterial cell viability.
Fagomine at more than 1 mmol/L significantly potentiated insulin secretion in isolated rat pancreatic islets induced by 10 mmol/L glucose.
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1M10C1P4SM
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53185-12-9
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DTXSID10201243
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72259
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SUBSTANCE RECORD