Abstract
Amygdalin is a cyanogenic glycoside found in pits and kernels of numerous plants especially from the family Rosaceae. Recently, in some countries, food supplements containing amygdalin have been offered for the use in the alternative cancer treatment. The effectivity of amygdalin in the antitumor therapy remained still questionable. Considering the potential toxicity of amygdalin, it is of a high importance to provide the information of its content in available food supplements. A fast hydrophilic interaction liquid chromatography-high performance liquid chromatography (HILIC-HPLC) method was developed for the analysis of amygdalin and 5-hydroxytryptamine (serotonin), using new Ascentis Express OH5 column (100 × 3.0 mm; 2.7 μm). Mobile phase composed of acetonitrile and 10 mM ammonium acetate pH 3.8, 90:10 (v/v) was used. The developed method was applied to the determination of amygdalin and serotonin in capsules containing apricot kernels and sea buckthorn berries as well as to the determination of amygdalin in apricot kernels and serotonin as a minority compound in sea buckthorn samples for food supplements. The method recovery was in the range 95.25–106.09 % for amygdalin and in the range 97.67–104.30 % for 5-hydroxytryptamine, respectively.
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References
American Cancer Society (1991) Unproven methods of cancer management. Laetrile CA Cancer J Clin 41:187–192
Baranowska I, Plonka J (2015) Simultaneous determination of biogenic amines and methylxanthines in foodstuff—sample preparation with HPLC-DAD-FL analysis. Food Anal Methods 8(4):963–972
Batool F, Shah AH, Ahmed SD, Haleem DJ (2009) Oral supplementation of Sea buckthorn (Hippophae rhamnoides L-spp. Turkestanica) fruit extract modifies haloperidol induced behavioral deficits and increases brain serotonin metabolism. J Food Drug Anal 17(4):257–263
Bell DS, Cramer H (2013) Retention and Selectivity of Polar Neutral Molecules in Hydrophilic Interaction Liquid Chromatography (HILIC), Reporter, Applications Newsletter 31.2., Sigma-Aldrich (visited 05/2015)
Bolarinwa IF, Orfila C, Morgan MRA (2014) Amygdalin content of seeds, kernels and food products commercially-available in the UK. Food Chem 152:133–139
Bolarinwa IF, Orfila C, Morgan MRA (2015) Determination of amygdalin in apple seeds, fresh apples and processed apple juices. Food Chem 170:437–442
Brad I, Vlasceanu GA, Brad IL, Manea S (2007) Characterization of Sea buckthorn fruits and copses in terms of serotonin and microelements. Innovative Romanian Food Biotechnology 1:24–30
Cabooter D, Fanigliulo A, Bellazzi G, Allieri B, Rottigni A, Desmet G (2010) Relationship between the particle size distribution of commercial fully porous and superficially porous high-performance liquid chromatography column packings and their chromatographic performance. J Chromatogr A 1217(45):7074–7081
Cao J, Murch SJ, O’Brien R, Saxena PK (2006) Rapid method for accurate analysis of melatonin, serotonin and auxin in plant samples using liquid chromatography-tandem mass spectrometry. J Chromatogr A 1134(1–2):333–337
Cheng YY, Yang CB, Zhao J, Tse HF, Rong JH (2015) Proteomic identification of calcium-binding chaperone calreticulin as a potential mediator for the neuroprotective and neuritogenic activities of fruit-derived glycoside amygdalin. J Nutr Biochem 26(2):146–154
De Benedetto GE, Fico D, Pennetta A, Malitesta C, Nicolardi G, Lofrumento DD et al (2014) A rapid and simple method for the determination of 3,4-dihydroxyphenylacetic acid, norepinephrine, dopamine, and serotonin in mouse brain homogenate by HPLC with fluorimetric detection. J Pharm Biomed Anal 98:266–270
European Pharmacopoeia (2015) 8th Edition. EDQM, Strasbourg Cedex
Fekete S, Olah E, Fekete J (2012) Fast liquid chromatography: the domination of core-shell and very fine particles. J Chromatogr A 1228:57–71
Gomez E, Burgos L, Soriano C, Marin J (1998) Amygdalin content in the seeds of several apricot cultivars. J Sci Food Agric 77(2):184–186
Gonzalez-Ruiz V, Olives AI, Martin MA (2015) Core-shell particles lead the way to renewing high-performance liquid chromatography. Trac-Trends Anal Chem 64:17–28
Guiochon G, Gritti F (2011) Shell particles, trials, tribulations and triumphs. J Chromatogr A 1218(15):1915–1938
Hemstrom P, Irgum K (2006) Hydrophilic interaction chromatography. J Sep Sci 29(12):1784–1821
Hirowatari Y, Hara K, Kamihata H, Iwasaka T, Takahashi H (2004) High-performance liquid chromatographic method with column-switching and post-column reaction for determination of serotonin levels in platelet-poor plasma. Clin Biochem 37(3):191–197
Huang X, Mazza G (2011) Simultaneous analysis of serotonin, melatonin, piceid and resveratrol in fruits using liquid chromatography tandem mass spectrometry. J Chromatogr A 1218(25):3890–3899
Jandera P (2008) Stationary phases for hydrophilic interaction chromatography, their characterization and implementation into multidimensional chromatography concepts. J Sep Sci 31(9):1421–1437
Kennedy D (1977) Laetrile: The Commissioner's Decision. Federal Register. Docket No. 77-22310
Lv WF, Ding MY, Zheng R (2005) Isolation and quantitation of amygdalin in Apricot-kernel and Prunus Tomentosa Thunb. by HPLC with solid-phase extraction. J Chromatogr Sci 43(7):383–387
McCalley DV, Neue UD (2008) Estimation of the extent of the water-rich layer associated with the silica surface in hydrophilic interaction chromatography. J Chromatogr A 1192(2):225–229
Milazzo S, Lejeune S, Ernst E (2007) Laetrile for cancer: a systematic review of the clinical evidence. Support Care Cancer 15(6):583–595
Mirmiranpour H, Khaghani S, Zandieh A, Khalilzadeh OO, Gerayesh-Nejad S, Morteza A et al (2012) Amygdalin inhibits angiogenesis in the cultured endothelial cells of diabetic rats. Indian J Pathol Microbiol 55(2):211–214
Pratuangdejkul J, Nosoongnoen W, Guerin GA, Loric S, Conti M, Launay JM et al (2006) Conformational dependence of serotonin theoretical pK(a) prediction. Chem Phys Lett 420(4–6):538–544
Regalado EL, Schafer W, McClain R, Welch CJ (2013) Chromatographic resolution of closely related species: separation of warfarin and hydroxylated isomers. J Chromatogr A 1314:266–275
Sanchez AC, Friedlander G, Fekete S, Anspach J, Guillarme D, Chitty M et al (2013) Pushing the performance limits of reversed-phase ultra high performance liquid chromatography with 1.3 mu m core-shell particles. J Chromatogr A 1311:90–97
Song ZQ, Xu XH (2014) Advanced research on anti-tumor effects of amygdalin. J Cancer Res Ther 10(5):3–7
Soukup J, Jandera P (2014) Adsorption of water from aqueous acetonitrile on silica-based stationary phases in aqueous normal-phase liquid chromatography. J Chromatogr A 1374:102–111
Suchard JR, Wallace KL, Gerkin RD (1998) Acute cyanide toxicity caused by apricot kernel ingestion. Ann Emerg Med 32(6):742–744
Syrigos KN, Rowlinson-Busza G, Epenetos AA (1998) In vitro cytotoxicity following specific activation of amygdalin by beta-glucosidase conjugated to a bladder cancer-associated monoclonal antibody. Int J Cancer 78(6):712–719
Tekes K (2008) HPLC determination of serotonin and its metabolites from human platelet-rich plasma; shift to 5-hydroxytryptophol formation following alcohol consumption. J Chromatogr Sci 46(2):169–173
The International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use (ICH). (2003). (Accessed 07/2015) http://www.ich.org/fileadmin/Public_Web_Site/ICH_Products/Guidelines/Quality/Q1A_R2/Step4/Q1A_R2__Guideline.pdf
Yildirim AN, Akinci-Yildirim F, Polat M, San B, Sesli Y (2014) Amygdalin content in kernels of several almond cultivars grown in Turkey. Hortscience 49(10):1268–1270
Acknowledgments
The authors would like to acknowledge the financial support of the project GAČR no. 15-10781S. Martina Parmová would like to acknowledge the financial support of specific research, no. SVV 260 184. The authors would like to gratefully acknowledge Lucie Nováková for the idea to use Ascentis Express OH5 column for the simultaneous determination of serotonin and amygdalin.
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Havlíková, L., Parmová, M., Chocholouš, P. et al. Sensitive Monitoring of Amygdalin and 5-Hydroxytryptamine in Food Supplements Using HILIC OH5 Chromatography. Food Anal. Methods 9, 1849–1856 (2016). https://doi.org/10.1007/s12161-015-0362-9
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DOI: https://doi.org/10.1007/s12161-015-0362-9