amygdalin

Summary

Summary: A cyanogenic glycoside found in the seeds of Rosaceae.

Top Publications

  1. Hwang E, Lee S, Lee J, Hong S. Development of quantitative extraction method of amygdalin without enzymatic hydrolysis from tonin(Persicae Semen) by high performance liquid chromatography. Arch Pharm Res. 2002;25:453-6 pubmed
    Tonin(Persicae Semen) is the herb medicine that contains amygdalin as a major ingredient. Amygdalin in water is decomposed into benzaldehyde, HCN, and glucose by emulsin, a hydrolysis enzyme in tonin...
  2. Hu S, Yuan D, Diao G, Bi K, Kano Y. [Stuides on evaluation of Semen Armeniacae amarum]. Zhongguo Zhong Yao Za Zhi. 2002;27:736-9 pubmed
    To systematically evaluate the quality of Semen Armeniacae Amarum. The amygdalin content in the samples of Semen Armeniacae Amarum from different markets was analysed by HPLC...
  3. Lv W, Ding M, Zheng R. Isolation and quantitation of amygdalin in Apricot-kernel and Prunus Tomentosa Thunb. by HPLC with solid-phase extraction. J Chromatogr Sci. 2005;43:383-7 pubmed
    Apricot-kernel and Prunus Tomentosa Thunb. are traditional Chinese herb medicines that contain amygdalin as their major effective ingredient...
  4. Cho A, Yi K, Rhim J, Kim K, Park J, Keum E, et al. Detection of abnormally high amygdalin content in food by an enzyme immunoassay. Mol Cells. 2006;21:308-13 pubmed
    b>Amygdalin is a cyanogenic glycoside compound which is commonly found in the pits of many fruits and raw nuts...
  5. Joo W, Jeong J, Kim H, Lee Y, Lee J, Hong S. Prevention of epimerization and quantitative determination of amygdalin in Armeniacae Semen with Schizandrae Fructus solution. Arch Pharm Res. 2006;29:1096-101 pubmed
    Armeniacae Semen not only contains amygdalin, but emulsin also, which is an enzyme that hydrolyzes amygdalin. The extraction yield of amygdalin from Armeniacae Semen was low, due to the presence of emulsin, when extracted with water...
  6. Yang H, Chang H, Lee J, Kim Y, Kim H, Lee M, et al. Amygdalin suppresses lipopolysaccharide-induced expressions of cyclooxygenase-2 and inducible nitric oxide synthase in mouse BV2 microglial cells. Neurol Res. 2007;29 Suppl 1:S59-64 pubmed
    b>Amygdalin (D-mandelonitrile-beta-D-gentiobioside) is a cynogenic compound found in sweet and bitter almonds, Persicae semen and Armeniacae semen. Amygdalin has been used for the treatment of cancers and for the relief of the pain...
  7. Bromley J, Hughes B, Leong D, Buckley N. Life-threatening interaction between complementary medicines: cyanide toxicity following ingestion of amygdalin and vitamin C. Ann Pharmacother. 2005;39:1566-9 pubmed
    To describe a case of severe accidental cyanide poisoning following a single ingestion of amygdalin with therapeutic intent...
  8. Mirmiranpour H, Khaghani S, Zandieh A, Khalilzadeh O, Gerayesh Nejad S, Morteza A, et al. Amygdalin inhibits angiogenesis in the cultured endothelial cells of diabetic rats. Indian J Pathol Microbiol. 2012;55:211-4 pubmed publisher
    ..The aim of this study was to investigate for the first time the antiangiogenic effects of amygdalin on the cultured endothelial cells of diabetic rats...
  9. Jiagang D, Li C, Wang H, Hao E, Du Z, Bao C, et al. Amygdalin mediates relieved atherosclerosis in apolipoprotein E deficient mice through the induction of regulatory T cells. Biochem Biophys Res Commun. 2011;411:523-9 pubmed publisher
    ..Therefore, in this study, we aimed to investigate the therapeutic effect of amygdalin on atherosclerosis of apolipoprotein E deficient (ApoE(-/-)) mice, and to explore its immune regulatory function ..

More Information

Publications62

  1. Chang H, Shin M, Yang H, Lee J, Kim Y, Lee M, 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;29:1597-602 pubmed
    Prostate cancer is one of the most common non-skin cancers in men. Amygdalin is one of the nitrilosides, natural cyanide-containing substances abundant in the seeds of plants of the prunasin family that have been used to treat cancers ..
  2. Chen Y, Ma J, Wang F, Hu J, Cui A, Wei C, et al. Amygdalin induces apoptosis in human cervical cancer cell line HeLa cells. Immunopharmacol Immunotoxicol. 2013;35:43-51 pubmed publisher
    b>Amygdalin, a naturally occurring substance, has been suggested to be efficacious as an anticancer substance. The effect of amygdalin on cervical cancer cells has never been studied...
  3. Park H, Yoon S, Han L, Zheng L, Jung K, Uhm Y, et al. Amygdalin inhibits genes related to cell cycle in SNU-C4 human colon cancer cells. World J Gastroenterol. 2005;11:5156-61 pubmed
    ..We compared the gene expression profiles of SNU-C4 cells between amygdalin-treated (5 mg/mL, 24 h) and non-treated groups using cDNA microarray analysis...
  4. Zhou C, Chen K, Sun C, Chen Q, Zhang W, Li X. Determination of oleanolic acid, ursolic acid and amygdalin in the flower of Eriobotrya japonica Lindl. by HPLC. Biomed Chromatogr. 2007;21:755-61 pubmed
    ..and accurate HPLC methods were developed for the determination of oleanolic acid (OA), ursolic acid (UA) and amygdalin in loquat (Eriobotrya japonica Lindl...
  5. Vemula P, Li J, John G. Enzyme catalysis: tool to make and break amygdalin hydrogelators from renewable resources: a delivery model for hydrophobic drugs. J Am Chem Soc. 2006;128:8932-8 pubmed
    ..The present approach could have applications in developing cost-effective controlled drug delivery vehicles from renewable resources, with a potential impact on pharmaceutical research and molecular design and delivery strategies. ..
  6. Hwang H, Lee H, Kim C, Shim I, Hahm D. Inhibitory effect of amygdalin on lipopolysaccharide-inducible TNF-alpha and IL-1beta mRNA expression and carrageenan-induced rat arthritis. J Microbiol Biotechnol. 2008;18:1641-7 pubmed
    b>Amygdalin is a cyanogenic glycoside plant compound found in the seeds of rosaceous stone fruits...
  7. Soranzo N, Bufe B, Sabeti P, Wilson J, Weale M, Marguerie R, et al. Positive selection on a high-sensitivity allele of the human bitter-taste receptor TAS2R16. Curr Biol. 2005;15:1257-65 pubmed
    ..The G protein-coupled receptor encoded by TAS2R16 mediates response to salicin, amygdalin, and many bitter beta-glucopyranosides...
  8. Vemula P, John G. Crops: a green approach toward self-assembled soft materials. Acc Chem Res. 2008;41:769-82 pubmed publisher
    ..using the selectivity of enzyme catalysis yield amphiphilic products derived from biobased feedstock including amygdalin, trehalose, and vitamin C...
  9. Juengel E, Afschar M, Makarevic J, Rutz J, Tsaur I, Mani J, et al. Amygdalin blocks the in vitro adhesion and invasion of renal cell carcinoma cells by an integrin-dependent mechanism. Int J Mol Med. 2016;37:843-50 pubmed publisher
    Information about the natural compound amygdalin, which is employed as an antitumor agent, is sparse and thus its efficacy remains controversial...
  10. Uretsky S. Quackery. Spotting it and avoiding it. Diabetes Self Manag. 2002;19:35-6, 38-9 pubmed
  11. Tanaka R, Nitta A, Nagatsu A. Application of a quantitative 1H-NMR method for the determination of amygdalin in Persicae semen, Armeniacae semen, and Mume fructus. J Nat Med. 2014;68:225-30 pubmed publisher
    A quantitative (1)H-NMR method (qHNMR) was used to measure the amygdalin content of Persicae semen, Armeniacae semen, and Mume fructus, in each of which amygdalin constitutes a major component...
  12. Yang D, Tong Y, Ma Z, Wang L, Dong M, Li Y, et al. [Simultaneous determination of ephedrine hydrochloride, D-pseudoephedrine and amygdalin in xiao'er pingchuan qutan granule by HPLC]. Zhongguo Zhong Yao Za Zhi. 2013;38:687-90 pubmed
    To establish an HPLC method for the determination of ephedrine hydrochloride, D-pseudo-ephedrine and amygdalin in Xiao'er Pingchuan Qutan granule. Pheny ether chromatographic column (4...
  13. Shu X, Tang Y, Jiang C, Shang E, Fan X, Ding A. Comparative analysis of the main bioactive components of San-ao decoction and its series of formulations. Molecules. 2012;17:12925-37 pubmed publisher
    ..applied for the simultaneous determination of seven main bioactive components including ephedrine (1), amygdalin (2), liquiritin (3), benzoic acid (4), isoliquiritin (5), formononetin (6) and glycyrrhizic acid (7) in San-ao ..
  14. Wang W, Shi X, Zhai L, Wang P, Peng X, Xu Y. [Influence of compatibility on content of berberine in Maxingganshi decoction]. Zhong Yao Cai. 2007;30:602-5 pubmed
    ..To set up the quantitative method of herberine in decoctions prepared from various combinations of Maxingganshi decotion by HPLC and to determine the change of general contents in different decoction...
  15. Barwina M, Wiergowski M, Sein Anand J. [Accidental poisoning with peach seeds used as anticancer therapy--report of two cases]. Przegl Lek. 2013;70:687-9 pubmed
    We described two cases of poisoning with amygdalin. Clinical signs presented by two females were mild and lasted up to 5 hours. The usage of amygdalin may be connected with serious side effects...
  16. Isoza T, Matano Y, Yamamoto K, Kosaka N, Tani T. Quantitative determination of amygdalin epimers by cyclodextrin-modified micellar electrokinetic chromatography. J Chromatogr A. 2001;923:249-54 pubmed
    A new capillary electrophoresis method was developed for the quantitative determination of the amygdalin epimers, amygdalin and neoamygdalin, which are biologically significant constituents in the crude drugs, namely Persicae Semen and ..
  17. Yi Y, Theis T, Young T. The effect of chlorination on organocyanide compounds. Water Environ Res. 2002;74:51-6 pubmed
    ..Four model compounds, acetonitrile, amygdalin, cyanocobalamin, and 2-acetoxy-3-butenenitrile, were selected and tested with varying chlorine dosages for ..
  18. Cho A, Shin K, Chung J, Oh S. A sensitive enzyme immunoassay for amygdalin in food extracts using a recombinant antibody. J Food Prot. 2008;71:2048-52 pubmed
    b>Amygdalin (laterile) is a cyanogenic glycoside commonly found in the pits of many fruits and raw nuts. When amygdalin-containing seeds are crushed and moistened, free cyanide is formed...
  19. Juengel E, Thomas A, Rutz J, Makarevic J, Tsaur I, Nelson K, et al. Amygdalin inhibits the growth of renal cell carcinoma cells in vitro. Int J Mol Med. 2016;37:526-32 pubmed publisher
    Although amygdalin is used by many cancer patients as an antitumor agent, there is a lack of information on the efficacy and toxicity of this natural compound...
  20. Brady C, Goszczynska T, Venter S, Cleenwerck I, De Vos P, Gitaitis R, et al. Pantoea allii sp. nov., isolated from onion plants and seed. Int J Syst Evol Microbiol. 2011;61:932-7 pubmed publisher
    ..for the differentiation of the isolates from their closest phylogenetic neighbours are production of acid from amygdalin and utilization of adonitol and sorbitol. A novel species, Pantoea allii sp. nov...
  21. John G, Shankar B, Jadhav S, Vemula P. Biorefinery: a design tool for molecular gelators. Langmuir. 2010;26:17843-51 pubmed publisher
    ..Amphiphiles based on naturally available raw materials such as amygdalin, vitamin C, cardanol, arjunolic acid, and trehalose that possess specific functionality were synthesized using ..
  22. Sánchez Pérez R, Jørgensen K, Olsen C, Dicenta F, Møller B. Bitterness in almonds. Plant Physiol. 2008;146:1040-52 pubmed publisher
    Bitterness in almond (Prunus dulcis) is determined by the content of the cyanogenic diglucoside amygdalin. The ability to synthesize and degrade prunasin and amygdalin in the almond kernel was studied throughout the growth season using ..
  23. Kang S, Jung H, Kim N, Shin D, Chung D. Micellar electrokinetic chromatography for the analysis of D-amygdalin and its epimer in apricot kernel. J Chromatogr A. 2000;866:253-9 pubmed
    We have developed a simple, rapid and reproducible method for the determination of D-amygdalin and its epimer by using micellar electrokinetic chromatography (MEKC)...
  24. Wagner B, Galey W. Kinetic analysis of hexose transport to determine the mechanism of amygdalin and prunasin absorption in the intestine. J Appl Toxicol. 2003;23:371-5 pubmed
    ..of the everted intestinal sac technique was utilized to study the transport of the cyanogenic glycoside amygdalin (D-mandelonitrile beta-D-gentiobioside) and its metabolite D-mandelontrile beta-D-glucoside (prunasin)...
  25. Hwang H, Kim P, Kim C, Lee H, Shim I, Yin C, et al. Antinociceptive effect of amygdalin isolated from Prunus armeniaca on formalin-induced pain in rats. Biol Pharm Bull. 2008;31:1559-64 pubmed
    b>Amygdalin is a plant glucoside isolated from the stones of rosaceous fruits, such as apricots, peaches, almond, cherries, and plums...
  26. Milazzo S, Lejeune S, Ernst E. Laetrile for cancer: a systematic review of the clinical evidence. Support Care Cancer. 2007;15:583-595 pubmed publisher
    ..Laetrile is also sometimes referred to as amygdalin, although the two are not the same...
  27. Miliauskas G, van Beek T, de Waard P, Venskutonis R, Sudhölter E. Comparison of analytical and semi-preparative columns for high-performance liquid chromatography-solid-phase extraction-nuclear magnetic resonance. J Chromatogr A. 2006;1112:276-84 pubmed
    ..For intermediately polar compounds (-2<logP<2) this has to be investigated per compound. ..
  28. Song S, Ma Q, Tang Q, Chen F, Xing X, Guo Y, et al. Stereoselective metabolism of amygdalin-based study of detoxification of Semen Armeniacae Amarum in the Herba Ephedrae-Semen Armeniacae Amarum herb pair. J Ethnopharmacol. 2016;179:356-66 pubmed publisher
    ..High performance liquid chromatography analysis of bioactive compounds (ephedrine, pseudoephedrine and amygdalin) in aqueous extracts and data from previous pharmacokinetic studies in rats were combined to explore the ..
  29. Yuan D, Sunouchi H, Sakurai T, Saito K, Kano Y. Pharmacological properties of traditional medicines (XXVII). Interaction between Ephedra Herb and Gypsum under hyperthermal conditions in rats. Biol Pharm Bull. 2002;25:872-4 pubmed
  30. Sánchez Pérez R, Belmonte F, Borch J, Dicenta F, Møller B, Jørgensen K. Prunasin hydrolases during fruit development in sweet and bitter almonds. Plant Physiol. 2012;158:1916-32 pubmed publisher
    b>Amygdalin is a cyanogenic diglucoside and constitutes the bitter component in bitter almond (Prunus dulcis). Amygdalin concentration increases in the course of fruit formation. The monoglucoside prunasin is the precursor of amygdalin...
  31. Perez J. Amygdalin analogs for the treatment of psoriasis. Future Med Chem. 2013;5:799-808 pubmed publisher
    ..Among them, inhibitors of JAK3, inhibitors of PDE 4 and amygdalin analogs...
  32. Guo J, Wu W, Sheng M, Yang S, Tan J. Amygdalin inhibits renal fibrosis in chronic kidney disease. Mol Med Rep. 2013;7:1453-7 pubmed publisher
    Renal interstitial fibrosis is a common outcome of chronic renal diseases. Amygdalin is one of a number of nitrilosides, the natural cyanide?containing substances abundant in the seeds of plants of the prunasin family that are used to ..
  33. Li X, Shi F, Zhang R, Sun C, Gong C, Jian L, et al. Pharmacokinetics, Safety, and Tolerability of Amygdalin and Paeoniflorin After Single and Multiple Intravenous Infusions of Huoxue-Tongluo Lyophilized Powder for Injection in Healthy Chinese Volunteers. Clin Ther. 2016;38:327-37 pubmed publisher
    ..b>Amygdalin (AD) and paeoniflorin (PF) are 2 typical bioactive components in HTLPI and were selected as indicators for this ..
  34. Perez J, Filizola M, Corcho F. Docking of peptide-T onto the D1 domain of the CD4 receptor. J Biomol Struct Dyn. 2000;17:725-33 pubmed
    ..These studies provide an improved description of the ligand-receptor pharmacophore. ..
  35. Cervellati C, Paetz C, Dondini L, Tartarini S, Bassi D, Schneider B, et al. A qNMR approach for bitterness phenotyping and QTL identification in an F1 apricot progeny. J Biotechnol. 2012;159:312-9 pubmed publisher
    In apricot the bitter flavor of seeds is determined by the amount of amygdalin, a cyanogenic glucoside whose cleavage by endogenous enzymes, upon seed crushing, releases toxic hydrogen cyanide...
  36. Barthet V, Bacala R. Development of optimized extraction methodology for cyanogenic glycosides from flaxseed (Linum usitatissimum). J AOAC Int. 2010;93:478-84 pubmed
    ..Extracts were stable for up to 1 week at room temperature and at least 2 weeks when refrigerated or frozen. ..
  37. Baroni A, Paoletti I, Greco R, Satriano R, Ruocco E, Tufano M, et al. Immunomodulatory effects of a set of amygdalin analogues on human keratinocyte cells. Exp Dermatol. 2005;14:854-9 pubmed
    ..Using computational methods, the natural product amygdalin was identified as peptidomimetic of PT. However, amygdalin exhibits a toxic profile due to its cyanide group...
  38. Moyad M. Results and lessons from clinical trials using dietary supplements for cancer: direct and indirect investigations. Semin Urol Oncol. 2001;19:232-46 pubmed
    ..In addition, indirect trials for other conditions (cardiovascular) may provide future insight into possible results for future cancer prevention trials. ..
  39. Seeram N, Cichewicz R, Chandra A, Nair M. Cyclooxygenase inhibitory and antioxidant compounds from crabapple fruits. J Agric Food Chem. 2003;51:1948-51 pubmed
    ..x Indian Summer yielded (+)-catechin (1), (-)-epicatechin (2), cyanidin-3-O-beta-galactopyranoside (3), and amygdalin (4)...
  40. Jose D, Elstner M, Schiller A. Allosteric indicator displacement enzyme assay for a cyanogenic glycoside. Chemistry. 2013;19:14451-7 pubmed publisher
    ..Herein, we report a chemical biosensor for the selective detection of the cyanogenic glycoside amygdalin in aqueous solution...
  41. Chan T. A probable case of amygdalin-induced peripheral neuropathy in a vegetarian with vitamin B12 deficiency. Ther Drug Monit. 2006;28:140-1 pubmed
  42. Bacala R, Barthet V. Development of extraction and gas chromatography analytical methodology for cyanogenic glycosides in flaxseed (Linum usitatissimum). J AOAC Int. 2007;90:153-61 pubmed
    ..Recoveries were as low as 82%, indicating that optimized extraction methodology is critical for the accuracy of results. ..
  43. Liu L, Duan J, Tang Y, Guo J, Yang N, Ma H, et al. Taoren-Honghua herb pair and its main components promoting blood circulation through influencing on hemorheology, plasma coagulation and platelet aggregation. J Ethnopharmacol. 2012;139:381-7 pubmed publisher
    ..This paper investigated the effects of TH and its main components amygdalin and hydroxysafflor yellow A (HSYA) on hemorheological disorders of blood stasis in rats...
  44. Du Q, Jerz G, Ha Y, Li L, Xu Y, Zhang Q, et al. Semi-industrial isolation of salicin and amygdalin from plant extracts using slow rotary counter-current chromatography. J Chromatogr A. 2005;1074:43-6 pubmed
    Salicin in the bark extract of Salix alba and amygdalin in the fruit extract of Semen armeniacae were each separated by slow rotary counter-current chromatography (SRCCC). The apparatus was equipped with a 40-L column made of 17 mm i.d...
  45. Zhu K, Sun X, Chang X, Qin J, Lv X, Wang Z, et al. [Pharmacokinetics of Guizhi Fuling capsule in Beagle dogs]. Zhongguo Zhong Yao Za Zhi. 2011;36:1015-8 pubmed
    ..43, 1.32 h. The AUC(0-t) of all components were related to dose. The pharmacokinetic course of peoniflorin, albiflorin and amygdaloside can be described by two-compartment model, and these components have high expose. ..
  46. Blaheta R, Nelson K, Haferkamp A, Juengel E. Amygdalin, quackery or cure?. Phytomedicine. 2016;23:367-76 pubmed publisher
    The cyanogenic diglucoside, amygdalin, has gained high popularity among cancer patients together with, or in place of, conventional therapy. Still, evidence based research on amygdalin is sparse and its benefit controversial...
  47. Yamshanov V, Kovan ko E, Pustovalov Y. Effects of Amygdaline from Apricot Kernel on Transplanted Tumors in Mice. Bull Exp Biol Med. 2016;160:712-4 pubmed publisher
    ..It was hypothesized that the antitumor effect of amygdaline on Ehrlich carcinoma and LYO-1 lymphosarcoma was associated with the presence of bacterial genome in the tumor. ..
  48. Kwon H, Lee J, Hong S. Improvement of the extraction efficiency of D-amygdalin from Armeniacae Semen powder through inactivating emulsin and suppressing the epimerization of D-amygdalin. Arch Pharm Res. 2010;33:81-6 pubmed publisher
    Armeniacae Semen contains not only amygdalin but also emulsin, which is an enzyme that hydrolyzes amygdalin. This hydrolysis reaction has been a major problem associated with the water extraction of Armeniacae Semen powder...
  49. Lee J, Zhang G, Wood E, Rogel Castillo C, Mitchell A. Quantification of amygdalin in nonbitter, semibitter, and bitter almonds (Prunus dulcis) by UHPLC-(ESI)QqQ MS/MS. J Agric Food Chem. 2013;61:7754-9 pubmed publisher
    b>Amygdalin is a cynaogenic diglucoside responsible for the bitterness of almonds. Almonds display three flavor phenotypes, nonbitter, semibitter, and bitter...
  50. Wright G, Mustard J, Simcock N, Ross Taylor A, McNicholas L, Popescu A, et al. Parallel reinforcement pathways for conditioned food aversions in the honeybee. Curr Biol. 2010;20:2234-40 pubmed publisher
    ..This second pathway may represent an ancient mechanism for food aversion learning conserved across animal lineages. ..
  51. Araya E, Rodriguez A, Rubio J, Spada A, Joglar J, Llebaria A, et al. Synthesis and evaluation of diverse analogs of amygdalin as potential peptidomimetics of peptide T. Bioorg Med Chem Lett. 2005;15:1493-6 pubmed
    ..In this direction, in a recent computational study the natural product amygdalin was identified as a prospective peptidomimetic of the peptide and later proved to exhibit a similar chemotactic ..
  52. Shaik N, Misra A, Singh S, Fatangare A, Ramakumar S, Rawal S, et al. Functional characterization, homology modeling and docking studies of ?-glucosidase responsible for bioactivation of cyanogenic hydroxynitrile glucosides from Leucaena leucocephala (subabul). Mol Biol Rep. 2013;40:1351-63 pubmed publisher
    ..Also, the enzyme hydrolyzed amygdalin, a hydroxynitrile glycoside and a few of the tested flavonoid and isoflavonoid glucosides...
  53. Hwang E, Lee J, Lee Y, Hong S. Reverse-phase HPLC separation of D-amygdalin and neoamygdalin and optimum conditions for inhibition of racemization of amygdalin. Chem Pharm Bull (Tokyo). 2002;50:1373-5 pubmed
    In boiling aqueous solution, D-amygdalin usually begins to convert into neoamygdalin in 3 min and more than 30% of the initial D-amygdalin is found as neoamygdalin after 30 min...