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Determination of Goitrogenic Metabolites in the Serum of Male Wistar Rat Fed Structurally Different Glucosinolates

  • Choi, Eun-Ji (Department of Food and Nutrition, Seoul National University) ;
  • Zhang, Ping (Department of Food and Nutrition, Seoul National University) ;
  • Kwon, Hoonjeong (Department of Food and Nutrition, Seoul National University)
  • Received : 2014.06.11
  • Accepted : 2014.06.28
  • Published : 2014.06.30

Abstract

Glucosinolates (GLSs) are abundant in cruciferous vegetables and reported to have anti thyroidal effects. Four GLSs (sinigrin, progoitrin, glucoerucin, and glucotropaeolin) were administered orally to rats, and the breakdown products of GLSs (GLS-BPs: thiocyanate ions, cyanide ions, organic isothiocyanates, organic nitriles, and organic thiocyanates) were measured in serum. Thiocyanate ions were measured by colorimetric method, and cyanide ions were measured with CI-GC-MS. Organic isothiocyanates and their metabolites were measured with the cyclocondensation assay. Organic nitriles and organic thiocyanates were measured with EI-GC-MS. In all treatment groups except for progoitrin, thiocyanate ions were the highest among the five GLS-BPs. In the progoitrin treated group, a high concentration of organic isothiocyanates (goitrin) was detected. In the glucoerucin treated group, a relatively low amount of goitrogenic substances was observed. The metabolism to thiocyanate ions happened within five hours of the administration, and the distribution of GLSs varied with the side chain. GLSs with side chains that can form stable carbocation seemed to facilitate the degradation reaction and produce a large amount of goitrogenic thiocyanate ions. Because goitrogenic metabolites can be formed without myrosinase, the inactivation of myrosinase during cooking would have no effect on the anti-nutritional effect of GLSs in cruciferous vegetables.

Keywords

References

  1. Fahey, J.W., Zalcmann, A.T. and Talalay, P. (2001) The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochemistry, 56, 5-51. https://doi.org/10.1016/S0031-9422(00)00316-2
  2. Fenwick, G.R. Heaney, R.K., Mullin, W.J. and Vanetten, C.H. (1982) Glucosinolates and their breakdown products in food and food plants. Crit. Rev. Food Sci. Nutr., 18, 123-201. https://doi.org/10.1080/10408398209527361
  3. Shapiro, T.A., Fahey, J.W., Wade, K.L., Stephenson, K.K. and Talalay, P. (2001) Chemoprotective glucosinolates and isothiocyanates of broccoli sprouts metabolism and excretion in humans. Cancer Epidemiol. Biomarkers Prev., 10, 501-508.
  4. Maskell, I. and Smithard, R. (1994) Degradation of glucosinolates during in vitro incubations of rapeseed meal with myrosinase (EC 3.2.3.1) and with pepsin (EC 3.4.23.1)-hydrochloric acid, and contents of porcine small intestine and caecum. Br. J. Nutr., 72, 455-466. https://doi.org/10.1079/BJN19940047
  5. Mennicke, W., Kral, T., Krumbiegel, G. and Rittmann, N. (1987) Determination of N-acetyl-S-(N-alkylthiocarbamoyl)-L-cysteine, a principal metabolite of alkyl isothiocyanates, in rat urine. J. Chromatogr. B Biomed. Sci. Appl., 414, 19-24. https://doi.org/10.1016/0378-4347(87)80020-8
  6. Slominski, B., Campbell, L. and Stanger, N. (1987) Influence of cecectomy and dietary antibiotics on the fate of ingested intact glucosinolates in poultry. Can. J. Anim. Sci., 67, 1117-1124. https://doi.org/10.4141/cjas87-117
  7. Slominski, B.A., Campbell, L.D. and Stanger, N.E. (1988) Extent of hydrolysis in the intestinal tract and potential absorption of intact glucosinolates in laying hens. J. Sci. Food Agric., 42, 305-314. https://doi.org/10.1002/jsfa.2740420404
  8. Holst, B. and Williamson, G. (2004) A critical review of the bioavailability of glucosinolates and related compounds. Nat. Prod. Rep., 21, 425-447. https://doi.org/10.1039/b204039p
  9. Heaney, R.K. and Fenwick, G.R. (1995) Natural toxins and protective factors in Brassica species, including rapeseed. Nat. Toxins, 3, 233-237. https://doi.org/10.1002/nt.2620030412
  10. Erdogan, M.F. (2003) Thiocyanate overload and thyroid disease. Biofactors, 19, 107-111. https://doi.org/10.1002/biof.5520190302
  11. Song, L., Iori, R. and Thornalley, P.J. (2006) Purification of major glucosinolates from Brassicaceae seeds and preparation of isothiocyanate and amine metabolites. J. Sci. Food Agric., 86, 1271-1280. https://doi.org/10.1002/jsfa.2488
  12. Rochfort, S., Caridi, D., Stinton, M., Trenerry, C. and Jones, R. (2006) The isolation and purification of glucoraphanin from broccoli seeds by solid phase extraction and preparative high performance liquid chromatography. J. Chromatogr. A, 1120, 205-210. https://doi.org/10.1016/j.chroma.2006.01.046
  13. Visentin, M., Tava, A., Iori, R. and Palmieri, S. (1992) Isolation and identification of trans-4-(methylthio)-3-butenyl glucosinolate from radish roots (Raphanus sativus L.). J. Agric. Food Chem., 40, 1687-1691. https://doi.org/10.1021/jf00021a041
  14. ISO norm. (1992) Rapeseed- Determination of glucosinolate content-Part 1: Method using high-performance liquid chromatography. I.S.O., ISO 9167-1, 1-9.
  15. van Staden, J. and Botha, A. (2000) Spectrophotometric determination of thiocyanate by sequential injection analysis. Anal. Chim. Acta, 403, 279-286. https://doi.org/10.1016/S0003-2670(99)00651-0
  16. Shim, K.H., Kang, K.S., Ahn, C.W. and Seo, K.I. (1993) Quantitative analysis of glucosinolates and thermal degradation product of indole glucosinolates in radish. J. Korean Agric. Chem. Soc., 36, 23-28.
  17. Bhandari, R.K., Oda, R.P., Youso, S.L., Petrikovics, I., Bebarta, V.S., Rockwood, G.A. and Logue, B.A. (2012) Simultaneous determination of cyanide and thiocyanate in plasma by chemical ionization gas chromatography massspectrometry (CI-GC-MS). Anal. Bioanal. Chem., 404, 2287-2294. https://doi.org/10.1007/s00216-012-6360-5
  18. Zhang, Y. (2012) The 1, 2-benzenedithiole-based cyclocondensation assay: a valuable tool for the measurement of chemopreventive isothiocyanates. Crit. Rev. Food Sci. Nutr., 52, 525-532. https://doi.org/10.1080/10408398.2010.503288
  19. Ye, L., Dinkova-Kostova, A.T., Wade, K.L., Zhang, Y., Shapiro, T.A. and Talalay, P. (2002) Quantitative determination of dithiocarbamates in human plasma, serum, erythrocytes and urine: pharmacokinetics of broccoli sprout isothiocyanates in humans. Clin. Chim. Acta, 316, 43-53. https://doi.org/10.1016/S0009-8981(01)00727-6
  20. McGregor, D. (1978) Thiocyanate ion, a hydrolysis product of glucosinolates from rape and mustard seed. Can. J. Plant Sci., 58, 795-800. https://doi.org/10.4141/cjps78-118
  21. Brusewitz, G., Cameron, B.D., Chasseaud, L.F., Gorler, K., Hawkins, D.R., Koch, H. and Mennicke, W.H. (1977) The metabolism of benzyl isothiocyanate and its cysteine conjugate. Biochem. J., 162, 99-107. https://doi.org/10.1042/bj1620099
  22. Chung, F.L., Morse, M.A. and Eklind, K.I. (1992) New potential chemopreventive agents for lung carcinogenesis of tobaccospecific nitrosamine. Cancer Res., 52, S2719-2722.
  23. Silver, E., Kuttab, S.H., Hasan, T. and Hassan, M. (1982) Structural considerations in the metabolism of nitriles to cyanide in vivo. Drug Metab. Dispos., 10, 495-498.
  24. Stea, K. (1952) The Effect of Thyroxine Administration on the Formation of Thiocyanate from Acetonitrile in Mice. Acta Pharmacol. Toxicol., 8, 263-270.
  25. Hideo, O. and Casida, J.E. (1971) Glutathione S-transferases liberate hydrogen cyanide from organic thiocyanates. Biochem. Pharmacol., 20, 1708-1711. https://doi.org/10.1016/0006-2952(71)90303-0
  26. Kjaer, A., Christensen, B. and Hansen, S. (1959) Isothiocyanates. 34. The absolute configuration of (-)-5-vinyl-2-oxazolidinethione (goitrin) and its glucosidic progenitor (progoitrin). Acta Chem. Scand., 13, 144-150. https://doi.org/10.3891/acta.chem.scand.13-0144
  27. Nishie, K. and Daxenbichler, E. (1982) Hepatic effects of Rgoitrin in sprague-dawley rats. Food Chem. Toxicol., 20, 279-287. https://doi.org/10.1016/S0278-6915(82)80294-9
  28. Fenwick, G. and Heaney, R. (1983) Glucosinolates and their breakdown products in cruciferous crops, foods and feedingstuffs. Food Chem., 11, 249-271. https://doi.org/10.1016/0308-8146(83)90074-2
  29. Griffiths, D.W., Deighton, N., Birch, A.E., Patrian, B., Baur, R. and Stadler, E. (2001) Identification of glucosinolates on the leaf surface of plants from the Cruciferae and other closely related species. Phytochemistry, 57, 693-700. https://doi.org/10.1016/S0031-9422(01)00138-8
  30. Park, H.U. (2012) Degradation patterns of glucosinolates in cruciferous vegetables under food processing conditions. Master's thesis, Department of Food and Nutrition, The graduate school, Seoul National University.

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