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Journal of Analysis and Testing

, Volume 3, Issue 4, pp 313–321 | Cite as

Quantification of Total Glucosinolates and Isothiocyanates for Common Brassicaceous Vegetables Consumed in the US Market Using Cyclocondensation and Thiocyanate Ion Measurement Methods

  • Jianghao Sun
  • Pei ChenEmail author
Original Paper
First Online:
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Abstract

Glucosinolates are a group of important sulfur and nitrogen containing plant secondary metabolites found in Brassicaceous vegetables that are associated with many health benefits. There is a growing interest in assessing dietary glucosinolates and their degradation products’ isothiocyanates exposure to humans. Determination of glucosinolates in plants is a very challenging task. In this study, the total glucosinolates from 22 commonly consumed Brassicaceous vegetables in the US market were determined by employing 1,2-benzenedithiol cyclocondensation for the determination of isothiocyanates (ITCs) from non-indole glucosinolates and a colorimetric method for the determination of thiocyanate ion (SCN−) from indole glucosinolates. The total glucosinolates were determined from the sum of these two methods. In the 22 investigated vegetables, the highest level of total ITCs was found in horse radish (5189.0 ± 544.8 nmol/g dry weight) and the highest level of total SCN− level was found in brussel sprouts (1294.0 ± 141.6 nmol/g dry weight). The total glucosinolates ranged from 18.6 ± 3.2 to 2271.2 ± 215.3 nmol/g dry weight. The total glucosinolate and ITC data are necessary for the USDA glucosinolates database and important for establishing the relationship of glucosinolates to human nutrition.

Keywords

Glucosinolate Isothiocyanate Thiocyanate ion Brassicaceous vegetables 
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Notes

Acknowledgements

This research is supported by the Agricultural Research Service of the US Department of Agriculture, an Interagency Agreement with the Office of Dietary Supplements at the National Institutes of Health.

Supplementary material

41664_2019_114_MOESM1_ESM.docx (80 kb)
Supplementary material 1 (DOCX 80 kb)

References

  1. 1.
    Clarke DB. Glucosinolates, structures and analysis in food. Anal Methods UK. 2010;2(4):310–25.  https://doi.org/10.1039/B9ay00280d.CrossRefGoogle Scholar
  2. 2.
    Zhang Y. Cancer-preventive isothiocyanates: measurement of human exposure and mechanism of action. Mutat Res. 2004;555(1–2):173–90.  https://doi.org/10.1016/j.mrfmmm.2004.04.017.CrossRefPubMedGoogle Scholar
  3. 3.
    Veeranki OL, Bhattacharya A, Tang L, Marshall JR, Zhang Y. Cruciferous vegetables, isothiocyanates, and prevention of bladder cancer. Curr Pharmacol Rep. 2015;1(4):272–82.  https://doi.org/10.1007/s40495-015-0024-z.CrossRefPubMedPubMedCentralGoogle Scholar
  4. 4.
    Bianchini F, Vainio H. Isothiocyanates in cancer prevention. Drug Metab Rev. 2004;36(3–4):655–67.  https://doi.org/10.1081/DMR-200033468.CrossRefPubMedGoogle Scholar
  5. 5.
    Abbaoui B, Telu KH, Lucas CR, Thomas-Ahner JM, Schwartz SJ, Clinton SK, et al. The impact of cruciferous vegetable isothiocyanates on histone acetylation and histone phosphorylation in bladder cancer. J Proteomics. 2017;156:94–103.  https://doi.org/10.1016/j.jprot.2017.01.013.CrossRefPubMedPubMedCentralGoogle Scholar
  6. 6.
    Tortorella SM, Royce SG, Licciardi PV, Karagiannis TC. Dietary sulforaphane in cancer chemoprevention: the role of epigenetic regulation and HDAC inhibition. Antioxid Redox Signal. 2015;22(16):1382–424.  https://doi.org/10.1089/ars.2014.6097.CrossRefPubMedPubMedCentralGoogle Scholar
  7. 7.
    Singh SV, Singh K. Cancer chemoprevention with dietary isothiocyanates mature for clinical translational research. Carcinogenesis. 2012;33(10):1833–42.  https://doi.org/10.1093/carcin/bgs216.CrossRefPubMedPubMedCentralGoogle Scholar
  8. 8.
    Kumar G, Tuli HS, Mittal S, Shandilya JK, Tiwari A, Sandhu SS. Isothiocyanates: a class of bioactive metabolites with chemopreventive potential. Tumour Biol J Int Soc Oncodevelop Biol Med. 2015;36(6):4005–16.  https://doi.org/10.1007/s13277-015-3391-5.CrossRefGoogle Scholar
  9. 9.
    Higdon JV, Delage B, Williams DE, Dashwood RH. Cruciferous vegetables and human cancer risk: epidemiologic evidence and mechanistic basis. Pharmacol Res. 2007;55(3):224–36.  https://doi.org/10.1016/j.phrs.2007.01.009.CrossRefPubMedPubMedCentralGoogle Scholar
  10. 10.
    Gupta P, Kim B, Kim SH, Srivastava SK. Molecular targets of isothiocyanates in cancer: recent advances. Mol Nutr Food Res. 2014;58(8):1685–707.  https://doi.org/10.1002/mnfr.201300684.CrossRefPubMedPubMedCentralGoogle Scholar
  11. 11.
    Bayat Mokhtari R, Baluch N, Homayouni TS, Morgatskaya E, Kumar S, Kazemi P, et al. The role of Sulforaphane in cancer chemoprevention and health benefits: a mini-review. J Cell Commun Signal. 2017.  https://doi.org/10.1007/s12079-017-0401-y.CrossRefPubMedPubMedCentralGoogle Scholar
  12. 12.
    Palaniswamy UR, McAvoy RJ, Bible BB, Stuart JD. Ontogenic variations of ascorbic acid and phenethyl isothiocyanate concentrations in watercress (Nasturtium officinale R. Br.) leaves. J Agric Food Chem. 2003;51(18):5504–9.  https://doi.org/10.1021/jf034268w.CrossRefPubMedGoogle Scholar
  13. 13.
    Chung FL, Morse MA, Eklind KI, Lewis J. Quantitation of human uptake of the anticarcinogen phenethyl isothiocyanate after a watercress meal. Cancer Epidemiol Biomark Prev. 1992;1(5):383–8.Google Scholar
  14. 14.
    Chung FL, Jiao D, Getahun SM, Yu MC. A urinary biomarker for uptake of dietary isothiocyanates in humans. Cancer Epidemiol Biomark Prev. 1998;7(2):103–8.Google Scholar
  15. 15.
    Thies W. Quantitative gas–liquid chromatography of glucosinolates on a microliter scale. Fett Wiss Technol. 1976;78(6):231–4.  https://doi.org/10.1002/lipi.19760780604.CrossRefGoogle Scholar
  16. 16.
    Kiddle G, Bennett RN, Botting NP, Davidson NE, Robertson AA, Wallsgrove RM. High-performance liquid chromatographic separation of natural and synthetic desulphoglucosinolates and their chemical validation by UV, NMR and chemical ionisation-MS methods. Phytochem Anal. 2001;12(4):226–42.  https://doi.org/10.1002/pca.589.CrossRefPubMedGoogle Scholar
  17. 17.
    Tian Q, Rosselot RA, Schwartz SJ. Quantitative determination of intact glucosinolates in broccoli, broccoli sprouts, Brussels sprouts, and cauliflower by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry. Anal Biochem. 2005;343(1):93–9.  https://doi.org/10.1016/j.ab.2005.04.045.CrossRefPubMedGoogle Scholar
  18. 18.
    Mohn T, Cutting B, Ernst B, Hamburger M. Extraction and analysis of intact glucosinolates—a validated pressurized liquid extraction/liquid chromatography-mass spectrometry protocol for Isatis tinctoria, and qualitative analysis of other cruciferous plants. J Chromatogr A. 2007;1166(1–2):142–51.  https://doi.org/10.1016/j.chroma.2007.08.028.CrossRefPubMedGoogle Scholar
  19. 19.
    Forster N, Ulrichs C, Schreiner M, Muller CT, Mewis I. Development of a reliable extraction and quantification method for glucosinolates in Moringa oleifera. Food Chem. 2015;166:456–64.  https://doi.org/10.1016/j.foodchem.2014.06.043.CrossRefPubMedGoogle Scholar
  20. 20.
    Ares AM, Nozal MJ, Bernal JL, Bernal J. Optimized extraction, separation and quantification of 12 intact glucosinolates in broccoli leaves. Food Chem. 2014;152:66–74.  https://doi.org/10.1016/j.foodchem.2013.11.125.CrossRefPubMedGoogle Scholar
  21. 21.
    Wu XL, Sun JH, Haytowitz DB, Harnly JM, Chen P, Pehrsson PR. Challenges of developing a valid dietary glucosinolate database. J Food Compos Anal. 2017;64:78–84.  https://doi.org/10.1016/j.jfca.2017.07.014.CrossRefGoogle Scholar
  22. 22.
    Sun J, Zhang M, Chen P. GLS-finder: a platform for fast profiling of glucosinolates in Brassica vegetables. J Agric Food Chem. 2016;64(21):4407–15.  https://doi.org/10.1021/acs.jafc.6b01277.CrossRefPubMedGoogle Scholar
  23. 23.
    Zhang Y, Cho CG, Posner GH, Talalay P. Spectroscopic quantitation of organic isothiocyanates by cyclocondensation with vicinal dithiols. Anal Biochem. 1992;205(1):100–7.CrossRefGoogle Scholar
  24. 24.
    Jiao D, Yu MC, Hankin JH, Low SH, Chung FL. Total isothiocyanate contents in cooked vegetables frequently consumed in Singapore. J Agric Food Chem. 1998;46(3):1055–8.  https://doi.org/10.1021/Jf9706989.CrossRefGoogle Scholar
  25. 25.
    Agerbirk N, De Vos M, Kim JH, Jander G. Indole glucosinolate breakdown and its biological effects. Phytochem Rev. 2009;8(1):101–20.  https://doi.org/10.1007/s11101-008-9098-0.CrossRefGoogle Scholar
  26. 26.
    Carlson DG, Daxenbichler ME, Vanetten CH, Tookey HL. Glucosinolates in crucifer vegetables—turnips and rutabagas. J Agric Food Chem. 1981;29(6):1235–9.  https://doi.org/10.1021/Jf00108a034.CrossRefPubMedGoogle Scholar
  27. 27.
    Carlson DG, Daxenbichler ME, Vanetten CH, Kwolek WF, Williams PH. Glucosinolates in crucifer vegetables—broccoli, brussels-sprouts, cauliflower, collards, kale, mustard greens, and kohlrabi. J Am Soc Hortic Sci. 1987;112(1):173–8.Google Scholar
  28. 28.
    Zhang Y, Wade KL, Prestera T, Talalay P. Quantitative determination of isothiocyanates, dithiocarbamates, carbon disulfide, and related thiocarbonyl compounds by cyclocondensation with 1,2-benzenedithiol. Anal Biochem. 1996;239(2):160–7.  https://doi.org/10.1006/abio.1996.0311.CrossRefPubMedGoogle Scholar
  29. 29.
    Thibaud JL, Wary C, Moullec S, Azzabou N, Le Guiner C, Garcia L, et al. Quantitative NMR 1H imaging and 31P spectroscopy evaluation of locoregional high venous pressure rAAV8-U7-ESE6-ESE8 exon-skipping therapy in the GRMD. Hum Gene Ther. 2012;23(10):A58–9.Google Scholar
  30. 30.
    Sun J, Kou L, Geng P, Huang H, Yang T, Luo Y, et al. Metabolomic assessment reveals an elevated level of glucosinolate content in CaCl(2) treated broccoli microgreens. J Agric Food Chem. 2015;63(6):1863–8.  https://doi.org/10.1021/jf504710r.CrossRefPubMedGoogle Scholar
  31. 31.
    Tang L, Paonessa JD, Zhang YS, Arnbrosone CB, McCann SE. Total isothiocyanate yield from raw cruciferous vegetables commonly consumed in the United States. J Funct Foods. 2013;5(4):1996–2001.  https://doi.org/10.1016/j.jff.2013.07.011.CrossRefPubMedPubMedCentralGoogle Scholar
  32. 32.
    Brown PD, Tokuhisa JG, Reichelt M, Gershenzon J. Variation of glucosinolate accumulation among different organs and developmental stages of Arabidopsis thaliana. Phytochemistry. 2003;62(3):471–81.  https://doi.org/10.1016/s0031-9422(02)00549-6.CrossRefPubMedGoogle Scholar

Copyright information

© The Nonferrous Metals Society of China 2019

Authors and Affiliations

  1. 1.Agricultural Research Service, Beltsville Human Nutrition Research Center, Methods and Application of Food Composition LaboratoryUS Department of AgricultureBeltsvilleUSA

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