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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H25NO10
Molecular Weight 427.4025
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VICIANIN

SMILES

O[C@H]1CO[C@@H](OC[C@H]2O[C@@H](O[C@@H](C#N)C3=CC=CC=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H]1O

InChI

InChIKey=YYYCJNDALLBNEG-GNRUMFBNSA-N
InChI=1S/C19H25NO10/c20-6-11(9-4-2-1-3-5-9)29-19-17(26)15(24)14(23)12(30-19)8-28-18-16(25)13(22)10(21)7-27-18/h1-5,10-19,21-26H,7-8H2/t10-,11-,12+,13-,14+,15-,16+,17+,18-,19+/m0/s1

HIDE SMILES / InChI

Molecular Formula C19H25NO10
Molecular Weight 427.4025
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Vicianin (mandelonitrile beta-vicianoside 6-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside) is a cyanogenic glycoside containing unusual disaccharide vicianose, composed of glucose and arabinose. Vicianin was first isolated and identified from Vicia Angustifolia seeds in 1906. It was later found in a number of fern species. Vicianin hydrolase catalyzes the hydrolysis of Vicianin into mandelonitrile and a disaccharide vicianose. The physiological and toxicological properties of this compound have not been evaluated in humans.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Rats were treated with vicianin 23.5 mg/100 g diet.
Route of Administration: Oral
In Vitro Use Guide
beta-Vicianosidase activity for Vicianin hydrolase was measured with the natural substrate vicianin. Enzyme activity was determined by measuring the liberation of aglycones from each glycoside. Each reaction mixture (50 mkl) contained 10mM substrate, 20mM citrate buffer (pH 6.0) and 10 mkl of the enzyme solution. A mixture without the enzyme was pre-incubated at 37C, and the reaction was started by adding the enzyme and stopped by the addition of 50 mkl of 1M Na2CO3. To determine the activity of a reaction mixture with vicianin, amygdalin and prunasin, each 20 ml of reaction mixture was subjected to HPLC, and benzaldehyde, which is a product of mandelonitrile liberated from the substrates, was detected at 250 nm. One unit was defined as the amount of enzyme liberating 1 mkmol benzaldehyde/min under the assay conditions. In the reactions with pNP b-glycosides, the activity was determined spectrophotometrically by measuring the liberated p-nitrophenol at 405 nm. For the reactions with furcatin, 20 mkl of reaction mixture was subjected to HPLC, and p-allylphenol (retention time, 7.6 min) liberated from the substrate was detected at 277 nm.
Substance Class Chemical
Record UNII
CQU61CXY3D
Record Status Validated (UNII)
Record Version