Details
| Stereochemistry | EPIMERIC |
| Molecular Formula | C14H17NO6 |
| Molecular Weight | 295.2879 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1O[C@@H](OC(C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI
InChIKey=ZKSZEJFBGODIJW-MXNNCRBYSA-N
InChI=1S/C14H17NO6/c15-6-9(8-4-2-1-3-5-8)20-14-13(19)12(18)11(17)10(7-16)21-14/h1-5,9-14,16-19H,7H2/t9?,10-,11-,12+,13-,14-/m1/s1
| Molecular Formula | C14H17NO6 |
| Molecular Weight | 295.2879 |
| Charge | 0 |
| Count |
|
| Stereochemistry | EPIMERIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 6 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Metabolites of amygdalin under simulated human digestive fluids. | 2010-12 |
|
| [Effect of processing on metabolism of amygdalin from bitter almond in rat]. | 2010-10 |
|
| DNA polymerases as potential therapeutic targets for cancers deficient in the DNA mismatch repair proteins MSH2 or MLH1. | 2010-03-16 |
|
| Tissue and cellular localization of individual beta-glycosidases using a substrate-specific sugar reducing assay. | 2009-12 |
|
| 3-O-methylfunicone, a selective inhibitor of mammalian Y-family DNA polymerases from an Australian sea salt fungal strain. | 2009-11-23 |
|
| Generation of primary amide glucosides from cyanogenic glucosides. | 2009-02 |
|
| Analysis of cyanogens with resorcinol and picrate. | 2008-11 |
|
| A new ferulic acid ester and other constituents from Dracocephalum peregrinum. | 2008-10 |
|
| Inhibitory effect of amygdalin on lipopolysaccharide-inducible TNF-alpha and IL-1beta mRNA expression and carrageenan-induced rat arthritis. | 2008-10 |
|
| A pseudo-beta-glucosidase in Arabidopsis thaliana: correction by site-directed mutagenesis, heterologous expression, purification, and characterization. | 2008-08 |
|
| Frequency and distribution of cyanogenic glycosides in Eucalyptus L'Hérit. | 2008-06 |
|
| Heterocyclic compounds from Chrysanthemum coronarium L. and their inhibitory activity on hACAT-1, hACAT-2, and LDL-oxidation. | 2008-05 |
|
| Larvae of the fall webworm, Hyphantria cunea, inhibit cyanogenesis in Prunus serotina. | 2008-03 |
|
| Bitterness in almonds. | 2008-03 |
|
| Two new maltol glycosides and cyanogenic glycosides from Elsholtzia rugulosa Hemsl. | 2008-01 |
|
| Ontogenetic and temporal trajectories of chemical defence in a cyanogenic eucalypt. | 2007-10 |
|
| Amygdalin induces apoptosis through regulation of Bax and Bcl-2 expressions in human DU145 and LNCaP prostate cancer cells. | 2006-08 |
|
| An HPLC/MS method for identifying major constituents in the hypocholesterolemic extracts of Chinese medicine formula 'Xue-Fu-Zhu-Yu decoction'. | 2006-08 |
|
| Absorption of toxic beta-glucosides produced by plants and their effect on tissue trehalases from insects. | 2006-03 |
|
| Cyanogenic glycosides from the rare Australian endemic rainforest tree Clerodendrum grayi (Lamiaceae). | 2006-01 |
|
| Purification and characterization of an intracellular beta-glucosidase from the methylotrophic yeast Pichia pastoris. | 2005-12 |
|
| Two new dammarane triterpenoids from Kageneckia angustifolia D. Don. | 2005-11 |
|
| Kinetics of the natural evolution of hydrogen cyanide in plants in neotropical Pteridium arachnoideum and its ecological significance. | 2005-02 |
|
| Cyanogenic glucosides in grapevine: polymorphism, identification and developmental patterns. | 2005-01 |
|
| The role of carboxyl, guanidine and imidazole groups in catalysis by a midgut trehalase purified from an insect larvae. | 2004-10 |
|
| Kinetic analysis of hexose transport to determine the mechanism of amygdalin and prunasin absorption in the intestine. | 2003-09-17 |
|
| Cyanogenic Eucalyptus nobilis is polymorphic for both prunasin and specific beta-glucosidases. | 2003-07 |
|
| Purification and characterization of vanilla bean (Vanilla planifolia Andrews) beta-D-glucosidase. | 2003-05-07 |
|
| Anti-tumor promoting effect of glycosides from Prunus persica seeds. | 2003-02 |
|
| Chromatographic determination of cyanoglycosides prunasin and amygdalin in plant extracts using a porous graphitic carbon column. | 2002-11-20 |
|
| A new acylated triterpene from the roots of Chaenomeles japonica. | 2002-08 |
|
| Investigation of the microheterogeneity and aglycone specificity-conferring residues of black cherry prunasin hydrolases. | 2002-07 |
|
| Cyanogenesis in glucosinolate-producing plants: Carica papaya and Carica quercifolia. | 2002-06 |
|
| Cucurbitacin F in seeds of Kageneckia angustifolia (Rosaceae). | 2002-04-03 |
|
| Pharmaco-toxicological study of Kageneckia oblonga, Rosaceae. | 2002-04-03 |
|
| Relationship between cyanogenic compounds in kernels, leaves, and roots of sweet and bitter kernelled almonds. | 2002-03-27 |
|
| New cyanogenic and alkyl glycoside constituents from Phyllagathis rotundifolia. | 2002-02 |
|
| DNA polymerase beta mediates protection of mammalian cells against ganciclovir-induced cytotoxicity and DNA breakage. | 2001-10-15 |
|
| Vicianin, prunasin, and beta-cyanoalanine in common vetch seed as sources of urinary thiocyanate in the rat. | 2001-10 |
|
| Purification and characterization of a beta-glucosidase from Citrus sinensis var. Valencia fruit tissue. | 2001-09 |
|
| Natural glycosides containing allopyranose from the passion fruit plant and circular dichroism of benzaldehyde cyanohydrin glycosides. | 2001-07-12 |
Patents
Sample Use Guides
Prunasin was dissolved in DMSO, and 4 ul of the dissolved sample was mixed with 16 uL of each enzyme (final, 0.05 unit) in 50mM Tris-HCl (pH 7.5) containing 0.1mM EDTA, 1mM dithiothreitol, and 50% glycerol, and then kept at 0C for 10 min. 8 uL of each of the preincubated solutions was added to 16 uL of enzyme standard reaction mixtures, and then enzyme activities were measured.
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
4J1L0618WK
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| Record Status |
Validated (UNII)
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| Record Version |
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