Prunasin

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Prunasin
Chemical structure of prunasin
Names
IUPAC name
(2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
Other names
(R)-Prunasin
D-Prunasin
D-Mandelonitrile-beta-D-glucoside
Identifiers
99-18-3
3D model (Jmol) Interactive image
ChEBI CHEBI:17396
ChemSpider 106360
ECHA InfoCard 100.002.489
EC Number 202-738-0
KEGG C00844
PubChem 119033
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).
Infobox references

Prunasin is a cyanogenic glucoside related to amygdalin.

Natural occurrences[edit]

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[edit]

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[edit]

  1. ^ 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 3320195Freely accessible. PMID 22353576. 
  2. ^ 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.