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Cyanogenic Glycosides
Published in Dongyou Liu, Handbook of Foodborne Diseases, 2018
With the glucoside of (R)-mandelonitrile, prunasin is a cyanogenic glycoside related to amygdalin. It is found in Prunus species (e.g., P. japonica or P. maximowiczii) and bitter almonds, as well as leaves and stems of Olinia ventosa, O. radiata, O. emarginata and O. rochetiana, Acacia greggii, and also dandelion coffee (a coffee substitute). Prunasin concentration in P. serotina roots appears to be influenced by species-specific adaptation, light and temperature conditions, ontogenetic shift, and interspecific plant-plant interactions.
Life-Threatening Cyanide Intoxication after Ingestion of Amygdalin in Prehospital Care
Published in Prehospital Emergency Care, 2022
Patrik Cmorej, Petr Bruthans, Jaroslav Halamka, Irena Voriskova, David Peran
After oral administration, amygdalin degrades in two different ways, in the small and large intestine. In the proximal jejunum, amygdalin is enzymatically hydrolyzed by β glucosidase to glucose and prunasin, which is transported unchanged into the bloodstream. Absorbed prunasin is excreted by the kidneys. Prunasin, which remains in the gastrointestinal tract, is degraded by β glucosidase to mandelonitrile. Mandelonitrile is a very unstable compound and therefore may be hydroxylated in the intestine to hydroxymandelonitrile, which passes through the intestinal wall, or may dissociate to benzaldehyde and cyanide, which is considered to be the active substance of amygdalin. In the large intestine, amygdalin is completely hydrolyzed by the intestinal microflora to benzaldehyde, glucose and cyanide. Cyanide easily passes through the intestinal wall into the bloodstream, where it reaches its maximum concentration in 1.5 to 2 hours. The toxic effect of amygdalin may be enhanced by concomitant administration of fruits and vegetables that contain β glucosidase (e.g. celery, carrots, peaches, beans). Oral intake of high doses of vitamin C (more than 3 g/day) promotes the hydrolysis of amygdalin in the intestine and potentiates side effects (1, 6).
Hepatoprotective effect of Xiayuxue decoction ethyl acetate fraction against carbon tetrachloride-induced liver fibrosis in mice via inducing apoptosis and suppressing activation of hepatic stellate cells
Published in Pharmaceutical Biology, 2020
Dingqi Zhang, Lijun Zhang, Gaofeng Chen, Ying Xu, Hailin Yang, Zhun Xiao, Jiamei Chen, Yongping Mu, Hua Zhang, Wei Liu, Ping Liu
The R. palmatum (batch number: 180223), P. persica Batsch (batch number: 180202), and E. sinensis (batch number: 180116) were purchased from Shanghai Kangqiao Chinese Medicine Tablet Co., Ltd. (Shanghai, China) and authenticated by associate professor Wei Liu, Institute of Liver Diseases, Shanghai University of Traditional Chinese Medicine. Amygdalin (Amy, 1), aloe-emodin (Alo, 9), rhein (Rhe, 10), emodin (Emo, 11), chrysophanol (Chr, 12) and physcion (Phy, 13) were purchased from Dalian Meilun Biotechnology Co., Ltd. (Dalian, China). Aloe-emodin-8-O-β-d-glucopyranoside (A-8-G, 3), rhein-8-O-β-d-glucopyranoside (R-8-G, 4), emodin-1-O-glucoside (E-1-G, 5), emodin-8-glucoside (E-8-G, 6), chrysophanol-8-O-β-d-glucopyranoside (C-8-G, 7) and chrysophanol-1-O-β-d-glucopyranoside (C-1-G, 8) were purchased from Chengdu Biopurify Phytochemicals Ltd. (Chengdu, China). Prunasin (Pru, 2) was obtained from Yuanye Biotech Company (Shanghai, China).