Skip to main content
SpringerLink
Log in

Analysis of the isothiocyanates present in three Chinese Brassica vegetable seeds and their potential anticancer bioactivities

  • Original Paper
  • Published:
European Food Research and Technology Aims and scope Submit manuscript

Abstract

Epidemiological studies give evidence that high dietary intake of cruciferous vegetables has been associated with lower risk of cancer, this activity due to their content in glucosinolates (GL), which upon myrosinase hydrolysis release the corresponding isothiocyanates (ITCs). In this study, the isothiocyanates contents and the anticancer activity of ethyl acetate extracts from three kinds of Chinese Brassica vegetable seeds have been examined and analyzed. A correlation was found between the potency of anticancer activity and the amount of isothiocyanates in their extracts. Extracts followed by GC–MS analysis revealed that 3-BITC (3-butenyl isothiocyanate) was mainly found in Chinese kale contained 77.58 ± 7.28 mg/g (dry weight); AITC (allyl isothiocyanate), 3-BITC and iberverin were the predominant isothiocyanates in Oxheart cabbage contained 33.57 ± 3.94, 26.50 ± 1.92 and 22.77 ± 0.00 mg/g, respectively; 3-BITC and sulforaphane were found as the major isothiocyanates in broccoli contained 138.52 ± 3.42 and 49.77 ± 0.18 mg/g, respectively. The amount of total isothiocyanates in broccoli was twice higher than that in other two species. The anticancer activity of broccoli was the highest, and the IC50 value of the extract inhibiting on the growth of A549, LAC, HELA and HepG2 were 14.38 ± 0.35, 10.38 ± 0.34, 19.45 ± 1.72 and 26.75 ± 0.82 mg/g, respectively. The extracts of Chinese Brassica vegetable seeds have the potential in inducing cancer cells apoptosis by morphology observation. The results of this study got a new kind of Brassica vegetable seeds that could produce high content of isothiocyanates, which is important to preparation of anticancer food additives.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

Abbreviations

ITCs:

Isothiocyanates

MTT:

3-[4, 5-Dimethylthiazol-2-yl]-2, 5-diphenyltetrazolium bromide

DMSO:

Dimethyl sulphoxide

HepG2 :

Human hepatocellular liver carcinoma cell

A549 and LAC:

Human lung carcinoma cell

HELA:

Human cervical carcinoma cell

AITC:

Allyl isothiocyanate

3-BITC:

3-Butenyl isothiocyanate

References

  1. Doll R, Peto R (1981) The causes of cancer: quantitative estimates of avoidable risks of cancer in the United States today. J Natl Cancer Inst 66:1191–1193

    CAS  Google Scholar 

  2. Steinmetz KA, Potter JD (1991) Vegetables, fruit and cancer. I. Epidemiology. Cancer Causes Control 2:325–357

    Article  CAS  Google Scholar 

  3. Stoewsand GS, Anderson JL, Munson L (1988) Protective effect of dietary Brussels sprouts against mammary carcinogenesis in Sprague–Dawley rats. Cancer Lett 39:199–207

    Article  CAS  Google Scholar 

  4. Verhoeven DTH, Goldbohm RA, van Poppel G, Verhagen H, van den Brandt PA (1996) Epidemiological studies on brassica vegetables and cancer risk. Cancer Epidem Biomar 5:733–748

    CAS  Google Scholar 

  5. Williamson G, Faulkner K, Plumb GW (1998) Glucosinolates and phenolics as antioxidants from plant foods. Eur J Cancer Prev 7:17–21

    CAS  Google Scholar 

  6. Steinkellner H, Rabot S, Freywald C, Nobis E, Scharf G, Chabicovsky M, Knasmüller S, Kassie F (2001) Effects of cruciferous vegetables and their constituents on drug metabolizing enzymes involved in the bioactivation of DNA-reactive dietary carcinogens. Mutat Res 480–481:285–297

    Google Scholar 

  7. Mithen RF, Dekker M, Verkerk R, Rabot S, Johnson IT (2000) The nutritional significance, biosynthesis and bioavailability of glucosinolates in human foods. J Sci Food Agric 80:967–984

    Article  CAS  Google Scholar 

  8. Duncan AJ, Milne JA (1989) Glucosinolates. Aspect Appl Biol 19:75–92

    Google Scholar 

  9. Zhang Y, Talalay P (1994) Anticarcinogenic activities of organic isothiocyanates: chemistry and mechanisms. Cancer Res 54:1976–1981

    Google Scholar 

  10. Hecht SS (1995) Chemoprevention by isothiocyanates. J Cell Biochem Suppl 22:195–209

    Article  CAS  Google Scholar 

  11. Hecht SS (1999) Chemoprevention of cancer by isothiocyanates, modifiers of carcinogen metabolism. J Nutr 129:768–774

    Google Scholar 

  12. Conaway CC, Yang YM, Chung FL (2002) Isothiocyanates as cancer chemopreventive agents: their biological activities and metabolism in rodents and humans. Curr Drug Metab 3:233–255

    Article  CAS  Google Scholar 

  13. Troncoso R, Espinoza C, Sánchez-Estrada A, Tiznado ME, Garcí Hugo S (2005) Analysis of the isothiocyanates present in cabbage leaves extract and their potential application to control Alternaria rot in bell peppers. Food Res Int 38:701–708

    Article  CAS  Google Scholar 

  14. Wang Z, Zhou J, Ju Y, Zhang H, Liu M, Li X (2001) Effects of two saponins extracted from the Polygonatum zanlanscianse on the human leukemia (HL-60) cells. Biol Pharm Bull 24:159–162

    Article  CAS  Google Scholar 

  15. Tai KW, Chou MY, Hu CC, Yang JJ, Chang YC (2000) Induction of apoptosis in KB cells by pingyangmycin. Oral Oncol 36:242–247

    Article  CAS  Google Scholar 

  16. Fahey JW, Zalcmann AT, Talalay P (2001) The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochemistry 56:5–51

    Article  CAS  Google Scholar 

  17. Kjaer A, Ohashi M, Wilson JM, Djerassi C (1963) Mass spectra of isothiocyanates. Acta Chem Scand 17:2143–2154

    Article  CAS  Google Scholar 

  18. Fisher M, Golden NH, Katzman DK, Kreipe RE, Rees J, Schebendach J, Sigman G, Ammerman S, Hoberman HM (1995) Eating disorders in adolescents: a background paper. J Adolesc Health 16:420–437

    Article  CAS  Google Scholar 

  19. Fenwick GR, Heaney RK, Mullin WJ (1983) Glucosinolates and their breakdown products in food and food plants. Crit Rev Food Sci Nutr 18:123–201

    Article  CAS  Google Scholar 

  20. Kushad MM, Brown AF, Kurilieh AC, Juvik JA, Klein BP, Wallig MA, Jefery EH (1999) Variation of glueosinolates in vegetable crops of Brassica oleracea. J Agric Food Chem 47:1541–1548

    Article  CAS  Google Scholar 

  21. Rosa EAS, Heaney RK, Fenwick GR, Portas CAM (1997) Glucosinolates in crop plants. Horticultural reviews 19:99–215

    CAS  Google Scholar 

  22. Wu X, Kassie F, Mersch-Sundermann V (2005) Induction of apoptosis in tumor cells by naturally occurring sulfur-containing compounds. Mutat Res 589:81–102

    Article  CAS  Google Scholar 

  23. Zhang Y (2004) Cancer-preventive isothiocyanates: measurement of human exposure and mechanism of action. Mutat Res 555:173–190

    CAS  Google Scholar 

  24. Tookey HL, Daxenbichler ME, VanEtten CH, Kwolek WF, Williams PH (1980) Cabbage glucosinolates: correspondence of patterns in seeds and leafy heads. J Am Soc Hortic Aci 105:714–717

    CAS  Google Scholar 

  25. Buttery RG, Guadagni DG, Ling LC, Seifert RM, Lipton W (1976) Additional volatile components of cabbage, broccoli and cauliflower. J Agric Food Chem 24:829–832

    Article  CAS  Google Scholar 

  26. VanEtten CH, Daxenbichler ME, Williams PH, Kwolek WF (1976) Glucosinolates and derived products in cruciferous vegetables. Analysis of the edible part from twenty-two varieties of cabbage. J Agric Food Chem 24:452–455

    Article  CAS  Google Scholar 

  27. Charron CS, Sams CE (1999) Inhibition of Pythium ultimum and Rhizoctonia solani by shredded leaves of brassica species. J Am Soc Hortic Sci 124:462–467

    CAS  Google Scholar 

  28. Kushad MM, Cloyd R, Babadoost M (2004) Distribution of glucosinolates in ornamental cabbage and kale cultivars. Sci Hortic 101:215–221

    Article  CAS  Google Scholar 

  29. Bennett RN, Mellon FA, Botting NP, Eagles J, Rosa EA, Williamson G (2002) Identification of the major glucosinolate (4-mercaptobutyl glucosinolate) in leaves of Eruca sativa L. (salad rocket). Phytochemistry 61:25–30

    Article  CAS  Google Scholar 

  30. Zhang Y, Talalay P, Cho CG, Posner GH (1992) A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure. Proc Natl Acad Sci USA 89:2399–2403

    Article  CAS  Google Scholar 

  31. Zhang Y, Kensler TW, Cho CG, Posner GH, Talalay P (1994) Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates. Proc Natl Acad Sci USA 91:3147–3150

    Article  CAS  Google Scholar 

  32. Matsui TA, Murata H, Sakabe T, Sowa Y, Horie N, Nakanishi R, Sakai T, Kubo T (2007) Sulforaphane induces cell cycle arrest and apoptosis in murine osteosarcoma cells in vitro and inhibits tumor growth in vivo. Oncol Rep 18:1263–1268

    CAS  Google Scholar 

  33. Pledgie-Tracy A, Sobolewski MD, Davidson NE (2007) Sulforaphane induces cell type specific apoptosis in human breast cancer cell lines. Mol Cancer Ther 6:1013–1021

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. College of Food Science and Biotechnology Engineering, Zhejiang Gongshang University, Hangzhou, Zhejiang, People’s Republic of China

    Nan Wang, Lianqing Shen, Xiangyang Wang, Kuiwu Wang & Mingfeng Xu

  2. South China Botanical Garden, Chinese Academy of Sciences (SCBG, CAS), Guangzhou, People’s Republic of China

    Shengxiang Qiu & Jing Hao

Authors
  1. Nan Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Lianqing Shen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Shengxiang Qiu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Xiangyang Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Kuiwu Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Jing Hao
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Mingfeng Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Lianqing Shen.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wang, N., Shen, L., Qiu, S. et al. Analysis of the isothiocyanates present in three Chinese Brassica vegetable seeds and their potential anticancer bioactivities. Eur Food Res Technol 231, 951–958 (2010). https://doi.org/10.1007/s00217-010-1348-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00217-010-1348-x

Keywords

Search

Navigation