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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
Structure of D-Fagomine

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

HIDE SMILES / InChI

Molecular Formula C6H13NO3
Molecular Weight 147.1723
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Originator

Curator's Comment: reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/22017795

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
42.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Fate of d-Fagomine after Oral Administration to Rats.
2017-06-07
D-Fagomine attenuates metabolic alterations induced by a high-energy-dense diet in rats.
2015-08
Effect of (D)-fagomine on excreted Enterobacteria and weight gain in rats fed a high-fat high-sucrose diet.
2014-04
The presence of D-fagomine in the human diet from buckwheat-based foodstuffs.
2013-02-15
D-Fagomine lowers postprandial blood glucose and modulates bacterial adhesion.
2012-06
Determination of D-fagomine in buckwheat and mulberry by cation exchange HPLC/ESI-Q-MS.
2012-02
Cytotoxicity and enzymatic activity inhibition in cell lines treated with novel iminosugar derivatives.
2010-02
Potentiation of glucose-induced insulin secretion by fagomine, a pseudo-sugar isolated from mulberry leaves.
1998-11
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:40:55 GMT 2025
Edited
by admin
on Mon Mar 31 21:40:55 GMT 2025
Record UNII
1M10C1P4SM
Record Status Validated (UNII)
Record Version
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Name Type Language
FAGOMINE, (+)-
Preferred Name English
D-Fagomine
Common Name English
3,4-Piperidinediol, 2-(hydroxymethyl)-, (2R,3R,4R)-
Systematic Name English
FAGOMINE, (D)-
Common Name English
Fagomine
Common Name English
(2R,3R,4R)-2-(Hydroxymethyl)-3,4-piperidinediol
Systematic Name English
Code System Code Type Description
FDA UNII
1M10C1P4SM
Created by admin on Mon Mar 31 21:40:55 GMT 2025 , Edited by admin on Mon Mar 31 21:40:55 GMT 2025
PRIMARY
CAS
53185-12-9
Created by admin on Mon Mar 31 21:40:55 GMT 2025 , Edited by admin on Mon Mar 31 21:40:55 GMT 2025
PRIMARY
EPA CompTox
DTXSID10201243
Created by admin on Mon Mar 31 21:40:55 GMT 2025 , Edited by admin on Mon Mar 31 21:40:55 GMT 2025
PRIMARY
PUBCHEM
72259
Created by admin on Mon Mar 31 21:40:55 GMT 2025 , Edited by admin on Mon Mar 31 21:40:55 GMT 2025
PRIMARY