Amygdalin
Amygdalin is a glucoside found in stone fruits and apples that exhibits antinociceptive, analgesic, and anticancer chemotherapeutic activities. In animal models, amygdalin decreases formalin-induced pain. Amygdalin inhibits viability of leukemia cells and induces apoptosis in prostate cancer cells, increasing levels of Bax and decreasing levels of Bcl-2; in vivo, amygdalin induces apoptosis and inhibits tumor xenograft growth.
References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18838454
Cas No. |
29883-15-6 |
---|---|
Purity |
≥98% |
Formula |
C20H27NO11 |
Formula Wt. |
457.43 |
Chemical Name |
[(6-O-β-D-glucopyranosyl-beta-D-gluco-pyranosyl- β-D-gluco-pyranosyl)oxy]-benzeneacetonitrile |
IUPAC Name |
2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile |
Synonym |
Amygdaloside |
Melting Point |
210ªC-215°C |
Solubility |
Soluble in hot water (0.1g/mL) or alcohol (1g/900mL). |
Appearance |
White to off white powder |
Chen Y, Ma J, Wang F, et al. Amygdalin induces apoptosis in human cervical cancer cell line HeLa cells. Immunopharmacol Immunotoxicol. 2013 Feb;35(1):43-51. PMID: 23137229.
Hwang HJ, Kim P, Kim CJ, et al. Antinociceptive effect of amygdalin isolated from Prunus armeniaca on formalin-induced pain in rats. Biol Pharm Bull. 2008 Aug;31(8):1559-64. PMID: 18670089.
Chang HK, Shin MS, Yang HY, et al. Amygdalin induces apoptosis through regulation of Bax and Bcl-2 expressions in human DU145 and LNCaP prostate cancer cells. Biol Pharm Bull. 2006 Aug;29(8):1597-602. PMID: 16880611.