Disease relevance of Amygdaloside

• The hazards of amygdalin therapy were evidenced in several patients by symptoms of cyanide toxicity or by blood cyanide levels approaching the lethal range [1].
• Failure of amygdalin to arrest B16 melanoma and BW5147 AKR leukemia [2].
• Additionally, the analysed strains differ from related Vibrio species by the utilization of melibiose and production of acid from L-arabinose and amygdalin [3].
• Under acidic and neutral conditions, amygdalin exists only as the D-form; however, under basic conditions, it shows both the D- and L-forms with a concentration ratio of 1:1.3 (D-amygdalin/L-amygdalin) [4].
• A probable case of amygdalin-induced peripheral neuropathy in a vegetarian with vitamin B12 deficiency [5].

High impact information on Amygdaloside

• These findings seriously question the use of amygdalin in clinical medicine under any circumstances [6].
• The G protein-coupled receptor encoded by TAS2R16 mediates response to salicin, amygdalin, and many bitter beta-glucopyranosides. beta-glucopyranosides are ubiquitous in nature, with many having a highly toxic cyanogenic activity [7].
• We demonstrate that although the guinea pig liver cytosolic beta-glucosidase does not catalyze the hydrolysis of gentiobiose, it does hydrolyze, disaccharide-containing glycosides such as p-nitrophenyl-beta-D-gentiobioside (Glc beta 1----6Glc beta-pNP) and mandelonitrile-beta-D-gentiobioside (amygdalin) [8].
• In black cherry (Prunus serotina Ehrh.) macerates, the cyanogenic diglucoside (R)-amygdalin undergoes stepwise degradation to HCN catalyzed by amygdalin hydrolase (AH), prunasin hydrolase, and (R)-(+)-mandelonitrile lyase (MDL) [9].
• Regardless of the source of isolation, the strains exhibited variable reactions mainly for arginine dihydrolase, ornithine decarboxylase, and fermentation of sucrose, melibiose, amygdalin, and salicin [10].

Chemical compound and disease context of Amygdaloside

• Studies of amygdalin (laetrile) toxicity in rodents [6].
• Parenteral amygdalin was found to be ineffective in C57BL/6 mice with B16 melanoma and in AKR mice with BW5147 lymphatic leukemia, in doses ranging from 50 to 5000 mg/kg [2].
• These strains differ from other related Vibrio species by several phenotypic features, which include acetoin and indole production and utilization of amygdalin and D-mannitol [11].
• Life-threatening interaction between complementary medicines: cyanide toxicity following ingestion of amygdalin and vitamin C [12].
• In addition, hamster blood cyanide and thiocyanate concentrations were determined at 0.5, 1, 2, 3 and 4 hr after an oral dose of 0.44 mmol linamarin or amygdalin/kg body weight [13].

Biological context of Amygdaloside

• A series of aminoitriles have been synthesized and studied whose nonenzymatic dissociation with release of cyanide may be varied by modest alteration of their molecular structure from that obtained with nonenzymatic dissociation of amygdalin to that obtained from enzymatic dissociation of amygdalin by substantial quantities of beta-glucosidase [14].
• The pharmacokinetics of amygdalin [15].
• On the metabolism of amygdalin. 1. The LD50 and biochemical changes in rats [16].
• CONCLUSION: These results suggest that amygdalin have an anticancer effect via downregulation of cell cycle-related genes in SNU-C4 human colon cancer cells, and might be used for therapeutic anticancer drug [17].
• Amygdalin was detected only in the kernels, mainly in bitter genotypes [18].

Anatomical context of Amygdaloside

• The intestinal first pass metabolism of amygdalin has been investigated in rat small intestine in vitro [19].
• By the application of this method, a simple, fast and simultaneous quantitative determinations of amygdalin epimers in the crude drugs (Persicae Semen and Armeniacae Semen) and the Chinese herbal prescriptions (Keishi-bukuryo-gan and Mao-to) were achieved [20].
• Immunomodulatory effects of a set of amygdalin analogues on human keratinocyte cells [21].
• Studies on high-dose chemotherapy of amygdalin in murine P388 lymphocytic leukaemia and P815 mast cell leukaemia [22].
• At the end of the 2nd h, the highest amygdalin content was found in the large intestine (0.79 mg) [23].

Associations of Amygdaloside with other chemical compounds

• Two forms of the beta-glucosidase amygdalin hydrolase (AH I and II), which catalyze the hydrolysis of (R)-amygdalin to (R)-prunasin and D-glucose, have been purified over 200-fold from mature black cherry (Prunus serotina Ehrh.) seeds [24].
• Antitussive effects of L-ephedrine, amygdalin, and makyokansekito (Chinese traditional medicine) using a cough model induced by sulfur dioxide gas in mice [25].
• These include amygdalin (occurring widely in the Rosaceae), the aliphatic cyanogens linamarin and lotaustralin (widely occurring, especially in the Leguminosae), and dhurrin together with its epimer taxiphyllin (occurring in the genus SORGHUM) [26].
• High-dose ascorbic acid decreases detoxification of cyanide derived from amygdalin (laetrile): studies in guinea pigs [27].
• The cyanogenic glycoside, amygdalin (4), and its hydrolysis products, mandelonitrile (5) and benzaldehyde (6), were not active in the antioxidant or COX enzyme inhibitory assays at 80 microM concentrations [28].

Gene context of Amygdaloside

• Amygdalin binds to the CD4 receptor as suggested from molecular modeling studies [29].
• CASE SUMMARY: A 68-year-old patient with cancer presented to the emergency department shortly after her first dose (3 g) of amygdalin with a reduced Glasgow Coma Score, seizures, and severe lactic acidosis requiring intubation and ventilation [12].
• Cancer tissues contain the enzyme rhodanese in amounts comparable to that of liver and kidney and hence, cannot be attacked selectively by cyanide release through beta-glucosidase action on amygdalin [30].
• Amygdalin MF was evaluated alone and in combination with an activating agent, beta-glucosidase, against three transplantable rodent tumors; Ridgway osteogenic sarcoma, Lewis lung carcinoma, and P388 leukemia [31].
• The optimal reflux is 2.5 h and water bath temperature is 60 degrees C. The solid-phase extraction method using C18 and multiwalled carbon nanotube as adsorbents is established the pretreatment of reflux extract, and the result shows that the two adsorbents have greater adsorptive capacity for amygdalin and good separation effect [32].

Analytical, diagnostic and therapeutic context of Amygdaloside

• Inhibition of [32P]phosphate uptake and [3H]thymidine incorporation into DNA of tumors was also observed after treatment of rats with amygdalin [33].
• If amygdalin could be activated specifically at the tumour site, then malignant cells would be killed without the systemic toxicity usually associated with chemotherapy [34].
• 0. Furthermore, no metabolic activity of isolated rat livers toward amygdalin and prunasin was observed within two hours of recirculating perfusion [19].
• Results of HPLC, UV-Vis spectrophotometry, and mass spectrometry reconfirmed the identification of D-amygdalin and its epimer [4].
• To measure low plasma concentrations of amygdalin following oral administration a GC/MS assay was developed [35].

References