Simultaneous determination of individual isothiocyanates in plant samples by HPLC-DAD-MS following SPE and derivatization with N-acetyl-l-cysteine - Publication - Bridge of Knowledge

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Simultaneous determination of individual isothiocyanates in plant samples by HPLC-DAD-MS following SPE and derivatization with N-acetyl-l-cysteine

Abstract

The procedure for the isothiocyanates (ITCs) determination that involves derivatization with N-acetyl-l-cysteine (NAC) and separation by HPLC was developed. Prior to derivatization, plant ITCs were isolated and purified using solid-phase extraction (SPE). The optimum conditions of derivatization are: 500 μL of isopropanolic eluate obtained by SPE combined with 500 μL of derivatizing reagent (0.2 M NAC and 0.2 M NaHCO3 in water) and reaction time of 1 h at 50 °C. The formed dithiocarbamates are directly analyzed by HPLC coupled with diode array detector and mass spectrometer if required. The method was validated for nine common natural ITCs. Calibration curves were linear (R2 ⩾ 0.991) within a wide range of concentrations and limits of detection were below 4.9 nmol/mL. The recoveries were in the range of 83.3–103.7%, with relative standard deviations <5.4%. The developed method has been successfully applied to determine ITCs in broccoli, white cabbage, garden cress, radish, horseradish and papaya.

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Category:
Articles
Type:
artykuł w czasopiśmie wyróżnionym w JCR
Published in:
FOOD CHEMISTRY no. 214, pages 587 - 596,
ISSN: 0308-8146
Language:
English
Publication year:
2017
Bibliographic description:
Pilipczuk T., Kusznierewicz B., Chmiel T., Przychodzeń W., Bartoszek-Pączkowska A.: Simultaneous determination of individual isothiocyanates in plant samples by HPLC-DAD-MS following SPE and derivatization with N-acetyl-l-cysteine// FOOD CHEMISTRY. -Vol. 214, (2017), s.587-596
DOI:
Digital Object Identifier (open in new tab) 10.1016/j.foodchem.2016.07.125
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  1. Agerbirk, N., De Nicola, G. R., Olsen, C. E., Müller, C., & Iori, R. (2015). Derivatization of isothiocyanates and their reactive adducts for chromatographic analysis. Phytochemistry, 118, 109-115. http://dx.doi.org/10.1016/j.phytochem.2015. 06.004. open in new tab
  2. Aires, A., Mota, V. R., Saavedra, M. J., Monteiro, A. A., Simões, M., Rosa, E. A. S., & Bennett, R. N. (2009). Initial in vitro evaluations of the antibacterial activities of glucosinolate enzymatic hydrolysis products against plant pathogenic bacteria. Journal of Applied Microbiology, 106(6), 2096-2105. http://dx.doi.org/10.1111/ j.1365-2672.2009.04181.x. open in new tab
  3. Aissani, N., Tedeschi, P., Maietti, A., Brandolini, V., Garau, V. L., & Caboni, P. (2013). Nematicidal activity of allylisothiocyanate from horseradish (Armoracia rusticana) roots against Meloidogyne incognita. Journal of Agricultural and Food Chemistry, 61(20), 4723-4727. http://dx.doi.org/10.1021/jf4008949. open in new tab
  4. Barillari, J., Iori, R., Broccoli, M., Pozzetti, L., Canistro, D., Sapone, A., ...
  5. Paolini, M. (2007). Glucoraphasatin and glucoraphenin, a redox pair of glucosinolates of brassicaceae, differently affect metabolizing enzymes in rats. Journal of Agricultural and Food Chemistry, 55(14), 5505-5511. http://dx.doi.org/10.1021/ jf070558r. open in new tab
  6. Bhat, V., Allan, K. M., & Rawal, V. H. (2011). Total synthesis of N-methylwelwitindolinone D isonitrile. Journal of the American Chemical Society, 133(15), 5798-5801. http://dx.doi.org/10.1021/Ja201834u. open in new tab
  7. Budnowski, J., Hanschen, F. S., Lehmann, C., Haack, M., Brigelius-Flohé, R., Kroh, L. W., ... Hanske, L. (2013). A derivatization method for the simultaneous detection of glucosinolates and isothiocyanates in biological samples. Analytical Biochemistry, 441(2), 199-207. http://dx.doi.org/10.1016/j.ab.2013.07.002. open in new tab
  8. Chen, C., & Ho, C. (1998). Thermal degradation of allyl isothiocyanate in aqueous solution. Journal of Agricultural and Food Chemistry, 46(1), 220-223. open in new tab
  9. Chiang, W. C. K., Pusateri, D. J., & Leitz, R. E. (1998). Gas chromatography/mass spectrometry method for the determination of sulforaphane and sulforaphane nitrile in broccoli. Journal of Agricultural and Food Chemistry, 46(97), 1018-1021. http://dx.doi.org/10.1021/jf970572b. open in new tab
  10. Chmiel, T., Abogado, D., & Wardencki, W. (2014). Optimization of capillary isotachophoretic method for determination of major macroelements in blue honeysuckle berries (Lonicera caerulea L.) and related products. Analytical and Bioanalytical Chemistry, 406(20), 4965-4986. http://dx.doi.org/10.1007/s00216- 014-7879-4. open in new tab
  11. Gupta, P., Wright, S. E., Kim, S. H., & Srivastava, S. K. (2014). Phenethyl isothiocyanate: A comprehensive review of anti-cancer mechanisms. Biochimica et Biophysica Acta -Reviews on Cancer, 1846(2), 405-424. http://dx. doi.org/10.1016/j.bbcan.2014.08.003. open in new tab
  12. Hanschen, F. S., Platz, S., Mewis, I., Schreiner, M., Rohn, S., & Kroh, L. W. (2012). Thermally induced degradation of sulfur-containing aliphatic glucosinolates in broccoli sprouts (Brassica oleracea var. Italica) and model systems. Journal of Agricultural and Food Chemistry, 60(9), 2231-2241. http://dx.doi.org/10.1021/ jf204830p. open in new tab
  13. Higdon, J. V., Delage, B., Williams, D. E., & Dashwood, R. H. (2009). Cruciferous vegetables and human cancer risk: Epidemiologic evidence and mechanistic basis. Pharmacological Research, 55(3), 224-236. http://dx.doi.org/10.1016/j. phrs.2007.01.009.Cruciferous. open in new tab
  14. Janobi, A. A., Al Mithen, R. F., Gasper, A. V., Shaw, P. N., Middleton, R. J., Ortori, C. A., & Barrett, D. A. (2006). Quantitative measurement of sulforaphane, iberin and their mercapturic acid pathway metabolites in human plasma and urine using liquid chromatography-tandem electrospray ionisation mass spectrometry. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, 844(2), 223-234. http://dx.doi.org/10.1016/j.jchromb.2006.07.007. open in new tab
  15. Jones, R. B., Frisina, C. L., Winkler, S., Imsic, M., & Tomkins, R. B. (2010). Cooking method significantly effects glucosinolate content and sulforaphane production open in new tab
  16. Fig. 4. The correlation between total ITC contents determined as ITC-NAC conju- gates and as BDTT for individual plant extracts. Pearson correlation coefficient is r = 0.996. in broccoli florets. Food Chemistry, 123(2), 237-242. http://dx.doi.org/10.1016/ j.foodchem.2010.04.016. open in new tab
  17. Kusznierewicz, B., Bą czek-Kwinta, R., Bartoszek, A., Piekarska, A., Huk, A., Manikowska, A., ... Konieczka, P. (2012). The dose-dependent influence of zinc and cadmium contamination of soil on their uptake and glucosinolate content in white cabbage (Brassica oleracea var. capitata f. alba). Environmental Toxicology and Chemistry, 31(11), 2482-2489. http://dx.doi.org/10.1002/ etc.1977. open in new tab
  18. Kusznierewicz, B., Bartoszek, A., Wolska, L., Drzewiecki, J., Gorinstein, S., & Namieśnik, J. (2008). Partial characterization of white cabbages (Brassica oleracea var. capitata f. alba) from different regions by glucosinolates, bioactive compounds, total antioxidant activities and proteins. LWT -Food Science and Technology, 41(1), 1-9. http://dx.doi.org/10.1016/j.lwt.2007.02.007. open in new tab
  19. Lai, K.-C., Huang, A.-C., Hsu, S.-C., Kuo, C.-L., Yang, J.-S., Wu, S.-H., & Chung, J.-G. (2010). Benzyl isothiocyanate (BITC) inhibits migration and invasion of human colon cancer HT29 cells by inhibiting matrix metalloproteinase-2/-9 and urokinase plasminogen (uPA) through PKC and MAPK signaling pathway. Journal of Agricultural and Food Chemistry, 58, 2935-2942. http://dx.doi.org/ 10.1021/jf9036694. open in new tab
  20. Li, N., Tu, M. S., Jiang, B., Wang, X., & Tu, S. J. (2013). Domino [3+2+1] heterocyclization of isothiocyanates with aryl amidines leading to polysubstituted 1,3,5-triazine derivatives. Tetrahedron Letters, 54(13), 1743-1746. http://dx.doi.org/10.1016/j.tetlet.2013.01.086. open in new tab
  21. Mathiselvam, M., Loganathan, D., & Varghese, B. (2013). Synthesis and characterization of thiourea-and urea-linked glycolipids as low-molecular- weight hydrogelators. RSC Advances, 3(34), 14528. http://dx.doi.org/10.1039/ c3ra42041h. open in new tab
  22. Matich, A. J., McKenzie, M. J., Lill, R. E., Brummell, D. A., McGhie, T. K., Chen, R. K. Y., & Rowan, D. D. (2012). Selenoglucosinolates and their metabolites produced in Brassica spp. fertilised with sodium selenate. Phytochemistry, 75, 140-152. http://dx.doi.org/10.1016/j.phytochem.2011.11.021. open in new tab
  23. Matusheski, N. V., Swarup, R., Juvik, J. A., Mithen, R., Bennett, M., & Jeffery, E. H. (2006). Epithiospecifier protein from broccoli (Brassica oleracea L. ssp. italica) inhibits formation of the anticancer agent sulforaphane. Journal of Agricultural and Food Chemistry, 54(6), 2069-2076. http://dx.doi.org/10.1021/jf0525277. open in new tab
  24. Mithen, R. F., Armah, C., & Traka, M. (2011). Vegetables, whole grains, and their derivatives in cancer prevention. In Cancer (pp. 1-30). http://dx.doi.org/10. 1007/978-90-481-9800-9. open in new tab
  25. Montaut, S., Barillari, J., Iori, R., & Rollin, P. (2010). Glucoraphasatin: Chemistry, occurrence, and biological properties. Phytochemistry, 71(1), 6-12. http://dx.doi. org/10.1016/j.phytochem.2009.09.021. open in new tab
  26. Navarro, S. L., Li, F., & Lampe, J. W. (2011). Mechanisms of action of isothiocyanates in cancer chemoprevention: An update. Food & Function, 2(10), 579-587. http:// dx.doi.org/10.1039/c1fo10114e. open in new tab
  27. Oliviero, T., Verkerk, R., Vermeulen, M., & Dekker, M. (2014). In vivo formation and bioavailability of isothiocyanates from glucosinolates in broccoli as affected by processing conditions. Molecular Nutrition and Food Research, 58(7), 1447-1456. http://dx.doi.org/10.1002/mnfr.201300894. open in new tab
  28. Pandurangan, K., Kitchen, J. A., McCabe, T., & Gunnlaugsson, T. (2013). Hydrogen bonding interactions and supramolecular networks of pyridine-aryl based thiosemicarbazides and their Zn(II) complexes. CrystEngComm, 15(7), 1421. http://dx.doi.org/10.1039/c2ce26718g. open in new tab
  29. Piekarska, A., Kołodziejski, D., Pilipczuk, T., Bodnar, M., Konieczka, P., Kusznierewicz, B., ... Bartoszek, A. (2014). The influence of selenium addition during germination of Brassica seeds on health-promoting potential of sprouts. International Journal of Food Sciences and Nutrition, 65(6), 692-702. http://dx. doi.org/10.3109/09637486.2014.917148. open in new tab
  30. Pilipczuk, T., Dawidowska, N., Kusznierewicz, B., Namieśnik, J., & Bartoszek, A. (2015). Simultaneous determination of indolic compounds in plant extracts by solid-phase extraction and high-performance liquid chromatography with UV and fluorescence detection. Food Analytical Methods, 8(9), 2169-2177. http://dx. doi.org/10.1007/s12161-015-0106-x. open in new tab
  31. Pilipczuk, T., Piekarska, A., Kusznierewicz, B., Bartoszek, A., & Namieśnik, J. (2013). Biofumigacja jako przyjazna środowisku technologia ochrony roślin. Analityka Nauka i Praktyka, 1, 36-46.
  32. Psurski, M., Piguła, M., Ciekot, J., Winiarski, Ł., Wietrzyk, J., & Oleksyszyn, J. (2012). Convenient syntheses of novel 1-isothiocyano-alkylphosphonate diphenyl ester derivatives with potential biological activity. Tetrahedron Letters, 53(44), 5845-5847. http://dx.doi.org/10.1016/j.tetlet.2012.08.037. open in new tab
  33. Rungapamestry, V., Duncan, A. J., Fuller, Z., & Ratcliffe, B. (2006). Changes in glucosinolate concentrations, myrosinase activity, and production of metabolites of glucosinolates in cabbage (Brassica oleracea var. capitata) cooked for different durations. Journal of Agricultural and Food Chemistry, 54 (20), 7628-7634. http://dx.doi.org/10.1021/jf0607314. open in new tab
  34. Shapiro, T. A., Fahey, J. W., Wade, K. L., Stephenson, K. K., & Talalay, P. (2001). Chemoprotective glucosinolates and ssothiocyanates of broccoli sprouts. Cancer Epidimiology Biomarkers & Prevention, 10(5), 501-508. open in new tab
  35. Smith, C. D., Baxendale, I. R., Tranmer, G. K., Baumann, M., Smith, S. C., Lewthwaite, R. A., & Ley, S. V. (2007). Tagged phosphine reagents to assist reaction work-up by phase-switched scavenging using a modular flow reactor. Organic & Biomolecular Chemistry, 5(10), 1562-1568. http://dx.doi.org/10.1039/b703033a. open in new tab
  36. Trott, D., Lepage, J., & Hebert, V. R. (2012). Assessing natural isothiocyanate air emissions after field incorporation of mustard cover crop. Bulletin of Environmental Contamination and Toxicology, 88(3), 482-485. http://dx.doi.org/ 10.1007/s00128-011-0506-6. open in new tab
  37. Vermeulen, M., Zwanenburg, B., Chittenden, G. J. F., & Verhagen, H. (2003). Synthesis of isothiocyanate-derived mercapturic acids. European Journal of Medicinal Chemistry, 38(7-8), 729-737. http://dx.doi.org/10.1016/S0223-5234 (03)00141-7. open in new tab
  38. Wesseling, C., McConnell, R., Partanen, T., & Hogstedt, C. (1997). Agricultural pesticide use in developing countries: Health effects and research needs. International Journal of Health Services, 27, 273-308. open in new tab
  39. Wilson, E. A., Ennahar, S., Zhao, M., Bergaentzle, M., Marchioni, E., & Bindler, F. (2011). Simultaneous determination of various isothiocyanates by RP-LC following precolumn derivatization with mercaptoethanol. Chromatographia, 73(SUPPL. 1). http://dx.doi.org/10.1007/s10337-010-1878-1. open in new tab
  40. Wittstock, U., & Burow, M. (2007). Tipping the scales -specifier proteins in glucosinolate hydrolysis. IUBMB Life, 59(12), 744-751. http://dx.doi.org/ 10.1080/15216540701736277. open in new tab
  41. Xian, L., & Kushad, M. M. (2004). Correlation of glucosinolate content to myrosinase activity in horseradish (Armoracia rusticana). Journal of Agricultural and Food Chemistry, 52(23), 6950-6955. http://dx.doi.org/10.1021/jf0401827. open in new tab
  42. Zhang, Y. S., Kolm, R. H., Mannervik, B., & Talalay, P. (1995). Reversible conjugation of isothiocyanates with glutathione catalyzed by human glutathione transferases. Biochemical and Biophysical Research Communications, 206(2), 748-755. http://dx.doi.org/10.1006/bbrc.1995.1106. open in new tab
  43. Zhang, Y., Wade, K. L., Prestera, T., & Talalay, P. (1996). Quantitative determination of isothiocyanates, dithiocarbamates, carbon disulfide, and related thiocarbonyl compounds by cyclocondensation with 1,2-benzenedithiol. Analytical Biochemistry, 239(2), 160-167. http://dx.doi.org/10.1006/abio.1996.0311. open in new tab
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