| 词条 | Prunasin |
| 释义 |
| ImageFile = Prunasin.svg | ImageSize = 200px | ImageAlt = Chemical structure of prunasin | IUPACName = (2R)-2-Phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile | OtherNames = (R)-Prunasin D-Prunasin D-Mandelonitrile-β-D-glucoside |Section1={{Chembox Identifiers | CASNo = 99-18-3 | PubChem = 119033 | EINECS = 202-738-0 | ChemSpiderID = 106360 | SMILES = C1=CC=C(C=C1)[C@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O | InChI = 1/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+/m0/s1 | InChIKey = ZKSZEJFBGODIJW-GMDXDWKABY | StdInChI = 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+/m0/s1 | StdInChIKey = ZKSZEJFBGODIJW-GMDXDWKASA-N | RTECS = | MeSHName = | ChEBI = 17396 | KEGG = C00844 |Section2={{Chembox Properties | C=14 | H=17 | N=1 | O=6 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} Prunasin is a cyanogenic glycoside related to amygdalin. Chemically, it is the glucoside of (R)-mandelonitrile. Natural occurrencesPrunasin 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] ToxicityPrunasin is hydrolyzed to produce hydrogen cyanide. Plants containing prunasin may therefore be toxic to animals, particularly ruminants.[4] MetabolismPrunasin 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. References1. ^{{Cite journal|doi=10.1104/pp.111.192021|pmid=22353576|title=Prunasin Hydrolases during Fruit Development in Sweet and Bitter Almonds|year=2012|last1=Sanchez-Perez|first1=R.|last2=Belmonte|first2=F. S.|last3=Borch|first3=J.|last4=Dicenta|first4=F.|last5=Møller|first5=B. L.|last6=Jørgensen|first6=K.|journal=Plant Physiology|volume=158|issue=4|pages=1916–32|pmc=3320195}} 2. ^{{cite journal|doi=10.1016/0031-9422(93)80024-M|title=Occurrence of the cyanogenic glucoside prunasin and II corresponding mandelic acid amide glucoside in Olinia species (oliniaceae)|year=1993|last1=Nahrstedt|first1=Adolf|last2=Rockenbach|first2=Jürgen|journal=Phytochemistry|volume=34|issue=2|pages=433}} 3. ^{{citation | author=Andrew Pengelly | title=The Constituents of Medicinal Plants | edition=2nd | year=2004 | publisher=Allen & Unwin | pages=44–45 | isbn=978-1-74114-052-1}} 4. ^{{Cite book | title = Toxicants of Plant Origin: Glycosides | author = Peter R. Cheeke | volume = 2 | page = 137 | publisher = CRC Press | date = 1989}} 4 : Cyanogenic glycosides|Alkaloids found in Fabaceae|Plant toxins|Glucosides |
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