| Identification | Back Directory | [Name]
taxiphyllin | [CAS]
21401-21-8 | [Synonyms]
taxiphyllin
(2R)-Taxiphyllin
(R)-4-hydroxymandelonitrileβ-D-glucoside
(2R)-(β-D-Glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile
Benzeneacetonitrile, α-(β-D-glucopyranosyloxy)-4-hydroxy-, (αR)-
(2R)-2-(4-hydroxyphenyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile | [Molecular Formula]
C14H17NO7 | [MDL Number]
MFCD20260892 | [MOL File]
21401-21-8.mol | [Molecular Weight]
311.29 |
| Chemical Properties | Back Directory | [InChI]
InChI=1/C14H17NO7/c15-5-9(7-1-3-8(17)4-2-7)21-14-13(20)12(19)11(18)10(6-16)22-14/h1-4,9-14,16-20H,6H2/t9-,10+,11+,12-,13+,14?/s3 | [InChIKey]
NVLTYOJHPBMILU-JNKDTEACNA-N | [SMILES]
C(#N)[C@@H](C1=CC=C(O)C=C1)OC1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 |&1:2,12,14,16,18,r| |
| Hazard Information | Back Directory | [Uses]
Taxiphyllin (2R-Taxiphyllin) is a plant cyanogenic glycoside, which exhibits inhibitory activity for tyrosinase[2]. Taxiphyllin exhibits cytotoxicity in BRL-3A cellls with an IC50 of 18.75 μm[3] and antimicrobial activities against Staphylococcus aureus with an EC50 of 0.96 μM[4]. | [Definition]
ChEBI: (R)-4-hydroxymandelonitrile beta-D-glucoside is a beta-D-glucoside consisting of (R)-prunasin carrying a hydroxy substituent at position 4 on the phenyl ring. It is a beta-D-glucoside and a nitrile. It is functionally related to a (R)-prunasin. | [References]
[1] Yang CJ, et al. Two new cyanogenic glucosides from the leaves of Hydrangea macrophylla. Molecules. 2012;17(5):5396-5403. DOI:10.3390/molecules17055396
[2] Wu B. Tyrosinase inhibitors from terrestrial and marine resources. Curr Top Med Chem. 2014;14(12):1425-49. DOI:10.2174/1568026614666140523115357
[3] Yi JJ, et al., Characterisation and in vitro cytotoxicity of toxic and degradation compounds in bamboo shoots (Dendrocalamus Sinicus) during traditional fermentation. Int J of Food Sci Tech. 2020
[4] Oueslati MH, et al., Phytochemical constituents from Salsola tetrandra. J Nat Prod. 2006 Sep;69(9):1366-9. DOI:10.1021/np060222w |
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