Prunasin
Appearance
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Names | |
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IUPAC name
(2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
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Other names
(R)-Prunasin
D-Prunasin D-Mandelonitrile-beta-D-glucoside | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.002.489 |
EC Number |
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KEGG | |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C14H17NO6 | |
Molar mass | 295.29 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Prunasin is a cyanogenic glucoside related to amygdalin.
Natural occurrences
Prunasin is found in species in the genus Prunus such as Prunus japonica or P. maximowiczii and in bitter almonds.[1] It is also found in leaves and stems of Olinia ventosa, O. radiata, O. emarginata and O. rochetiana[2] or in Acacia greggii.
It is also found in dandelion coffee, a coffee substitute.
Metabolism
Prunasin beta-glucosidase is an enzyme that uses (R)-prunasin and H2O to produce D-glucose and mandelonitrile.
Amygdalin beta-glucosidase is an enzyme that uses (R)-amygdalin and H2O to produce (R)-prunasin and D-glucose.
References
- ^ Sanchez-Perez, R.; Belmonte, F. S.; Borch, J.; Dicenta, F.; Møller, B. L.; Jørgensen, K. (2012). "Prunasin Hydrolases during Fruit Development in Sweet and Bitter Almonds". Plant Physiology. 158 (4): 1916–32. doi:10.1104/pp.111.192021. PMC 3320195. PMID 22353576.
- ^ Nahrstedt, Adolf; Rockenbach, Jürgen (1993). "Occurrence of the cyanogenic glucoside prunasin and II corresponding mandelic acid amide glucoside in Olinia species (oliniaceae)". Phytochemistry. 34 (2): 433. doi:10.1016/0031-9422(93)80024-M.