Prunasin
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Prunasin
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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 | |
| Other names (R)-Prunasin D-Prunasin D-Mandelonitrile-β-D-glucoside | |
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ChemSpider |
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ECHA InfoCard | 100.002.489 |
EC Number | 202-738-0 |
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| Properties | |
Chemical formula | C14H17NO6 |
Molar mass | 7002295291000000000♠295.291 g·mol−1 |
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 glycoside related to amygdalin. Chemically, it is the glucoside of (R)-mandelonitrile.
Contents
1 Natural occurrences
2 Toxicity
3 Metabolism
4 References
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] and in Acacia greggii.
It is also found in dandelion coffee, a coffee substitute.
Sambunigrin, a diastereomer of prunasin derived from (S)-mandelonitrile instead of it the (R)-isomer, has been isolated from leaves of the elder tree (Sambucus nigra)[3]
Toxicity[edit]
Prunasin is hydrolyzed to produce hydrogen cyanide. Plants containing prunasin may therefore be toxic to animals, particularly ruminants.[4]
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]
^ 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..mw-parser-output cite.citationfont-style:inherit.mw-parser-output .citation qquotes:"""""""'""'".mw-parser-output .citation .cs1-lock-free abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-subscription abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registrationcolor:#555.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration spanborder-bottom:1px dotted;cursor:help.mw-parser-output .cs1-ws-icon abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center.mw-parser-output code.cs1-codecolor:inherit;background:inherit;border:inherit;padding:inherit.mw-parser-output .cs1-hidden-errordisplay:none;font-size:100%.mw-parser-output .cs1-visible-errorfont-size:100%.mw-parser-output .cs1-maintdisplay:none;color:#33aa33;margin-left:0.3em.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-formatfont-size:95%.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-leftpadding-left:0.2em.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-rightpadding-right:0.2em
^ 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.
^ Andrew Pengelly (2004), The Constituents of Medicinal Plants (2nd ed.), Allen & Unwin, pp. 44–45, ISBN 978-1-74114-052-1
^ Peter R. Cheeke (1989). Toxicants of Plant Origin: Glycosides. 2. CRC Press. p. 137.
Categories:
- Cyanogenic glycosides
- Alkaloids found in Fabaceae
- Plant toxins
- Glucosides
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