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Chemical Compound Review

amygdalin     (2R)-2-phenyl-2-[3,4,5- trihydroxy-6-[[3,4...

Synonyms: D-Amygdalin, Vitamin B17, CPD-1125, AC1LCV2Y, NSC15780, ...
 
 
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Disease relevance of Amygdaloside

 

High impact information on Amygdaloside

 

Chemical compound and disease context of Amygdaloside

 

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

 

Associations of Amygdaloside with other chemical compounds

 

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

  1. A clinical trial of amygdalin (Laetrile) in the treatment of human cancer. Moertel, C.G., Fleming, T.R., Rubin, J., Kvols, L.K., Sarna, G., Koch, R., Currie, V.E., Young, C.W., Jones, S.E., Davignon, J.P. N. Engl. J. Med. (1982) [Pubmed]
  2. Failure of amygdalin to arrest B16 melanoma and BW5147 AKR leukemia. Hill, G.J., Shine, T.E., Hill, H.Z., Miller, C. Cancer Res. (1976) [Pubmed]
  3. Vibrio rotiferianus sp. nov., isolated from cultures of the rotifer Brachionus plicatilis. Gomez-Gil, B., Thompson, F.L., Thompson, C.C., Swings, J. Int. J. Syst. Evol. Microbiol. (2003) [Pubmed]
  4. Micellar electrokinetic chromatography for the analysis of D-amygdalin and its epimer in apricot kernel. Kang, S.H., Jung, H., Kim, N., Shin, D.H., Chung, D.S. Journal of chromatography. A. (2000) [Pubmed]
  5. A probable case of amygdalin-induced peripheral neuropathy in a vegetarian with vitamin B12 deficiency. Chan, T.Y. Therapeutic drug monitoring. (2006) [Pubmed]
  6. Studies of amygdalin (laetrile) toxicity in rodents. Khandekar, J.D., Edelman, H. JAMA (1979) [Pubmed]
  7. Positive selection on a high-sensitivity allele of the human bitter-taste receptor TAS2R16. Soranzo, N., Bufe, B., Sabeti, P.C., Wilson, J.F., Weale, M.E., Marguerie, R., Meyerhof, W., Goldstein, D.B. Curr. Biol. (2005) [Pubmed]
  8. Exolytic hydrolysis of toxic plant glucosides by guinea pig liver cytosolic beta-glucosidase. Gopalan, V., Pastuszyn, A., Galey, W.R., Glew, R.H. J. Biol. Chem. (1992) [Pubmed]
  9. Temporal and spatial expression of amygdalin hydrolase and (R)-(+)-mandelonitrile lyase in black cherry seeds. Zheng, L., Poulton, J.E. Plant Physiol. (1995) [Pubmed]
  10. Comparison of the taxonomy, serology, drug resistance transfer, and virulence of Citrobacter freundii strains from mammals and poikilothermic hosts. Toranzo, A.E., Cutrín, J.M., Roberson, B.S., Núñez, S., Abell, J.M., Hetrick, F.M., Baya, A.M. Appl. Environ. Microbiol. (1994) [Pubmed]
  11. Vibrio pacinii sp. nov., from cultured aquatic organisms. Gomez-Gil, B., Thompson, F.L., Thompson, C.C., Swings, J. Int. J. Syst. Evol. Microbiol. (2003) [Pubmed]
  12. Life-threatening interaction between complementary medicines: cyanide toxicity following ingestion of amygdalin and vitamin C. Bromley, J., Hughes, B.G., Leong, D.C., Buckley, N.A. The Annals of pharmacotherapy. (2005) [Pubmed]
  13. Comparative metabolism of linamarin and amygdalin in hamsters. Frakes, R.A., Sharma, R.P., Willhite, C.C. Food Chem. Toxicol. (1986) [Pubmed]
  14. Liberation of cyanide from alpha-aminonitriles relative to amygdalin. Winstead, M.B., Ciccarelli, C.A., Winchell, H.S. J. Pharmacol. Exp. Ther. (1978) [Pubmed]
  15. The pharmacokinetics of amygdalin. Rauws, A.G., Olling, M., Timmerman, A. Arch. Toxicol. (1982) [Pubmed]
  16. On the metabolism of amygdalin. 1. The LD50 and biochemical changes in rats. Adewusi, S.R., Oke, O.L. Can. J. Physiol. Pharmacol. (1985) [Pubmed]
  17. Amygdalin inhibits genes related to cell cycle in SNU-C4 human colon cancer cells. Park, H.J., Yoon, S.H., Han, L.S., Zheng, L.T., Jung, K.H., Uhm, Y.K., Lee, J.H., Jeong, J.S., Joo, W.S., Yim, S.V., Chung, J.H., Hong, S.P. World J. Gastroenterol. (2005) [Pubmed]
  18. Relationship between cyanogenic compounds in kernels, leaves, and roots of sweet and bitter kernelled almonds. Dicenta, F., Martínez-Gómez, P., Grané, N., Martín, M.L., León, A., Cánovas, J.A., Berenguer, V. J. Agric. Food Chem. (2002) [Pubmed]
  19. Intestinal first pass metabolism of amygdalin in the rat in vitro. Strugala, G.J., Rauws, A.G., Elbers, R. Biochem. Pharmacol. (1986) [Pubmed]
  20. Quantitative determination of amygdalin epimers by cyclodextrin-modified micellar electrokinetic chromatography. Isoza, T., Matano, Y., Yamamoto, K., Kosaka, N., Tani, T. Journal of chromatography. A. (2001) [Pubmed]
  21. Immunomodulatory effects of a set of amygdalin analogues on human keratinocyte cells. Baroni, A., Paoletti, I., Greco, R., Satriano, R.A., Ruocco, E., Tufano, M.A., Perez, J.J. Exp. Dermatol. (2005) [Pubmed]
  22. Studies on high-dose chemotherapy of amygdalin in murine P388 lymphocytic leukaemia and P815 mast cell leukaemia. Chitnis, M.P., Adwankar, M.K., Amonkar, A.J. J. Cancer Res. Clin. Oncol. (1985) [Pubmed]
  23. On the metabolism of amygdalin. 2. The distribution of beta-glucosidase activity and orally administered amygdalin in rats. Adewusi, S.R., Oke, O.L. Can. J. Physiol. Pharmacol. (1985) [Pubmed]
  24. Comparison of kinetic and molecular properties of two forms of amygdalin hydrolase from black cherry (Prunus serotina Ehrh.) seeds. Kuroki, G.W., Poulton, J.E. Arch. Biochem. Biophys. (1986) [Pubmed]
  25. Antitussive effects of L-ephedrine, amygdalin, and makyokansekito (Chinese traditional medicine) using a cough model induced by sulfur dioxide gas in mice. Miyagoshi, M., Amagaya, S., Ogihara, Y. Planta Med. (1986) [Pubmed]
  26. The metabolism of a natural product: lessons learned from cyanogenic glycosides. Conn, E.E. Planta Med. (1991) [Pubmed]
  27. High-dose ascorbic acid decreases detoxification of cyanide derived from amygdalin (laetrile): studies in guinea pigs. Basu, T.K. Can. J. Physiol. Pharmacol. (1983) [Pubmed]
  28. Cyclooxygenase inhibitory and antioxidant compounds from crabapple fruits. Seeram, N.P., Cichewicz, R.H., Chandra, A., Nair, M.G. J. Agric. Food Chem. (2003) [Pubmed]
  29. Amygdalin binds to the CD4 receptor as suggested from molecular modeling studies. Llorens, O., Filizola, M., Spisani, S., Marastoni, M., Herranz, C., Perez, J.J. Bioorg. Med. Chem. Lett. (1998) [Pubmed]
  30. The case against laetrile: the fraudulent cancer remedy. Greenberg, D.M. Cancer (1980) [Pubmed]
  31. Experimental studies of the antitumor activity of amygdalin MF (NSC-15780) alone and in combination with beta-glucosidase (NSC-128056). Laster, W.R., Schabel, F.M. Cancer chemotherapy reports. Part 1. (1975) [Pubmed]
  32. Isolation and quantitation of amygdalin in Apricot-kernel and Prunus Tomentosa Thunb. by HPLC with solid-phase extraction. Lv, W.F., Ding, M.Y., Zheng, R. Journal of chromatographic science. (2005) [Pubmed]
  33. Effects of cyanate, thiocyanate, and amygdalin on metabolite uptake in normal and neoplastic tissues of the rat. Lea, M.A., Koch, M.R. J. Natl. Cancer Inst. (1979) [Pubmed]
  34. In vitro cytotoxicity following specific activation of amygdalin by beta-glucosidase conjugated to a bladder cancer-associated monoclonal antibody. Syrigos, K.N., Rowlinson-Busza, G., Epenetos, A.A. Int. J. Cancer (1998) [Pubmed]
  35. Pharmacology of amygdalin (laetrile) in cancer patients. Ames, M.M., Moyer, T.P., Kovach, J.S., Moertel, C.G., Rubin, J. Cancer Chemother. Pharmacol. (1981) [Pubmed]
 
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