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Glucosinolates in the human diet. Bioavailability and implications for health

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Abstract

The glucosinolates are a large group of sulphur-containing glucosides found in brassica vegetables. After physical damage to the plant tissue, glucosinolates are broken down, by the endogenous enzyme myrosinase, releasing glucose and a complex variety of biologically active products. The most important and extensively studied of these compounds are the isothiocyanates. Glucosinolates can be degraded or leached from vegetable tissue during food processing, but thermal inactivation of myrosinase preserves some intact glucosinolates in cooked vegetables. Once ingested, any remaining intact glucosinolates may be broken down by plant myrosinase in the small intestine, or by bacterial myrosinase in the colon. Isothiocyanates are absorbed from the small bowel and colon, and the metabolites are detectable in human urine 2–3 h after consumption of brassica vegetables. Isothiocyanates are potent inducers of Phase II enzymes in vitro, and they have been shown to increase the metabolism and detoxification of chemical carcinogens in vitro and in animal models. Some of these compounds also inhibit mitosis and stimulate apoptosis in human tumour cells, in vitro and in vivo. This second effect raises the possibility that in addition to blocking DNA damage, isothiocyanates may selectively inhibit the growth of tumour cells even after initiation by chemical carcinogens. Epidemiological evidence supports the possibility that glucosinolate breakdown products derived from brassica vegetables may protect against human cancers, especially those of the gastrointestinal tract and lung. To define and exploit these potentially anticarcinogenic effects it is important to understand and manipulate glucosinolate chemistry and metabolism across the whole food-chain, from production and processing to consumption.

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References

  • Bird RP (1995) Role of aberrant crypt foci in understanding the pathogenesis of colon cancer. Cancer Lett. 93: 55-71.

    Article  PubMed  CAS  Google Scholar 

  • Chiao JW, Chung F, Krzeminski J, Amin S, Arshad R, Ahmed T & Conaway CC (2000) Modulation of growth of human prostate cancer cells by the N-acetylcysteine conjugate of phenethyl isothiocyanate. Int. J. Oncol. 16: 1215-1219.

    PubMed  CAS  Google Scholar 

  • Chung FL, Conaway CC, Rao CV & Reddy BS (2000) Chemoprevention of colonic aberrant crypt foci in Fischer rats by sulforaphane and phenethyl isothiocyanate. Carcinogenesis 21: 2287-2291.

    Article  PubMed  CAS  Google Scholar 

  • Combourieu B, Elfoul L, Delort AM & Rabot S (2001) Identification of new derivatives of sinigrin and glucotropaeolin produced by the human digestive microflora using (1)h nmr spectroscopy analysis of in vitro incubations. Drug Metab. Dispos. 29: 1440-1445.

    PubMed  CAS  Google Scholar 

  • Dekker M, R. Verkerk PR & Jongen WMF (2000) Predictive modelling of health aspects in the food production chain: A case study on glucosinolates in cabbage. Trends Food Sci. Tech. 11: 174-181.

    Article  CAS  Google Scholar 

  • Elfoul L, Rabot S, Khelifa N, Quinsac A, Duguay A & Rimbault A (2001) Formation of allyl isothiocyanate from sinigrin in the digestive tract of rats monoassociated with a human colonic strain of Bacteroides thetaiotaomicron. FEMS Microbiol. Lett. 197: 99-103.

    Article  PubMed  CAS  Google Scholar 

  • Fenwick GR, Griffiths NM & Heaney RK (1982) Bitterness in Brussels sprouts (Brassica oleraceaL. var gemmifera): The role of glucosinolates and their breakdown products. J. Sci. Food Agric. 34: 73-80.

    Google Scholar 

  • 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  PubMed  CAS  Google Scholar 

  • Gamet-Payrastre L, Li P, Lumeau S, Cassar G, Dupont MA, Chevolleau S, Gasc N, Tulliez J & Terce F (2000) Sulforaphane, a naturally occurring isothiocyanate, induces cell cycle arrest and apoptosis in HT29 human colon cancer cells. Cancer Res. 60: 1426-1433.

    PubMed  CAS  Google Scholar 

  • Getahun SM & Chung F-L (1999) Conversion of glucosinolates to isothiocyantes in humans after ingestion of cooked watercress. Cancer Epidemiol. Biomark. Prev. 8: 447-451.

    CAS  Google Scholar 

  • Hasegawa T, Nishino H & Iwashima A (1993) Isothiocyanates inhibit cell cycle progression of HeLa cells at G2/M phase. Anticancer Drugs 4: 273-279.

    PubMed  CAS  Google Scholar 

  • Hecht SS, Trushin N, Rigotty J, Carmella SG, Borukhova A, Akerkar S & Rivenson A (1996) Complete inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced rat lung tumorigenesis and favorable modification of biomarkers by phenethyl isothiocyanate. Cancer Epidemiol. Biomarkers Prev. 5: 645-652.

    PubMed  CAS  Google Scholar 

  • Johnson I, Williamson G & Musk S (1994) Anticarcinogenic factors in plant foods: A new class of nutrients? Nutr. Res. Rev. 7: 175-204.

    Article  CAS  PubMed  Google Scholar 

  • Johnson IT (2001) Mechanisms and anticarcinogenic effects of dietrelated apoptosis in the intestinal mucosa. Nutr. Res. Rev. 14: 229-256.

    Article  PubMed  CAS  Google Scholar 

  • Kirlin WG, Cai J, DeLong MJ, Patten EJ & Jones DP (1999) Dietary compounds that induce cancer preventive phase 2 enzymes activate apoptosis at comparable doses in HT29 colon carcinoma cells. J. Nutr. 129: 1827-1835.

    PubMed  CAS  Google Scholar 

  • Krul C, Humblot C, Philippe C, Vermeulen M, Van Nuenen M, Havenaar R & Rabot S (2002) Metabolism of sinigrin (2-propenyl glucosinolate) by the human colonic microflora in a dynamic in vitro large-intestinal model. Carcinogenesis, 23: 1009-1016.

    Article  PubMed  CAS  Google Scholar 

  • Langer P, Michajlovskij N, Sedlak J & Kutka M (1971) Studies on the antithyroid activity of naturally occurring L-5-vinyl-2-thiooxazolidone in man. Endokrinologie, 57: 225-229.

    PubMed  CAS  Google Scholar 

  • Lin HJ, Probst-Hensch NM, Louie AD, Kau IH, Witte JS, Ingles SA, Frankl HD, Lee ER & Haile RW (1998) Glutathione transferase null genotype, broccoli, and lower prevalence of colorectal adenomas. Cancer Epidemiol. Biomarkers Prev. 7: 647-652.

    PubMed  CAS  Google Scholar 

  • London SJ, Yuan JM, Chung FL, Gao YT, Coetzee GA, Ross RK & YuMC (2000) Isothiocyanates, glutathione S-transferase M1 and T1 polymorphisms, and lung-cancer risk: a prospective study of men in Shanghai, China. Lancet 356: 724-729.

    Article  PubMed  CAS  Google Scholar 

  • Lund EK, Smith TK, Clarke RG & Johnson IT (2001) Cell death in the colorectal cancer cell line HT29 in response to glucosinolate metabolites. J. Sci. Food Agric. 81: 959-961.

    Article  CAS  Google Scholar 

  • Lund EK, Smith TK, Latham P, Clarke R & Johnson IT (2000). Influence of biologically active food constituents on apoptosis and cell cycle in colorectal epithelial cells. In: Johnson IT & Genwick GR (eds) Dietary Anticarcinogens and Antimutagens: Chemical and Biological Aspects, (pp. 333-337). Royal Society of Chemistry, Cambridge.

    Google Scholar 

  • 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 

  • Musk SR & Johnson IT (1993) Allyl isothiocyanate is selectively toxic to transformed cells of the human colorectal tumour line HT29. Carcinogenesis 14: 2079-2083.

    PubMed  CAS  Google Scholar 

  • Musk SR, Stephenson P, Smith TK, Stening P, Fyfe D & Johnson IT (1995). Selective toxicity of compounds naturally present in food toward the transformed phenotype of human colorectal cell line HT29. Nutr Cancer 24: 289-298.

    Article  PubMed  CAS  Google Scholar 

  • Nijhoff WA, Grubben MJ, Nagengast FM, Jansen JB, Verhagen H, van Poppel G & Peters WH (1995a) Effects of consumption 188 of Brussels sprouts on intestinal and lymphocytic glutathione S-transferases in humans. Carcinogenesis 16: 2125-2128.

    PubMed  CAS  Google Scholar 

  • Nijhoff WA, Mulder TP, Verhagen H, van Poppel G & Peters WH (1995b) Effects of consumption of brussels sprouts on plasma and urinary glutathione S-transferase class-alpha and-pi in humans. Carcinogenesis 16: 955-957.

    PubMed  CAS  Google Scholar 

  • Rabot S, Guerin C, Nugon-Baudon L & Szylit O (1995) Glucosinolate degradation by bacterial strains isolated from a human intestinal microflora. In Proc. 9th International Rapeseed Congress 1: 212-214.

    Google Scholar 

  • Rouzard G, Duncan AJ, Rabot S, Ratcliffe B, Durao S, Garrido S & Young S (2000) Factors influencing the release of cancerprotective isothiocyanates in the digestive tract of rats following consumption of glucosinolate-rich brassica vegetables. In: Johnson IT & Fenwick GR (eds) Dietary Anticarcinogens and Antimutagens: Chemical and Biological Aspects (pp. 92-95). Royal Society of Chemistry, Cambridge.

    Google Scholar 

  • Shapiro TA, Fahey JW, Wade KL, Stephenson KK & Talalay P (1998) Human metabolism and excretion of cancer chemoprotective glucosinolates and isothiocyanates of cruciferous vegetables. Cancer Epidemiol. Biomarkers Prev. 7: 1091-1100.

    PubMed  CAS  Google Scholar 

  • Smith TK, Clarke R, Scott J & Johnson IT (2000) Raw Brussels sprouts block mitosis in colorectal cancer cells (HT29) and induce apoptosis in rat colonic mucosal crypts in vivo. In: Johnson IT & Fenwick GR (eds) Dietary Anticarcinogens and Antimutagens: Chemical and Biological Aspects. Royal Society of Chemistry, Cambridge.

    Google Scholar 

  • Smith TK, Lund EK & Johnson IT (1998) Inhibition of dimethylhydrazine-induced aberrant crypt foci and induction of apoptosis in rat colon following oral administration of the glucosinolate sinigrin. Carcinogenesis, 19: 267-273.

    Article  PubMed  CAS  Google Scholar 

  • Steinkellner H, Hietsch G, Sreerama L, Haidinger G, Gsur A, Kundi M & Knasmuller S. (2000) Induction of glutathione-S-transferase in humans by vegetable diets. In: IT Johnson & GR Fenwick (eds) Dietary Anticarcinogens and Antimutagens: Chemical and Biological Aspects (pp. 193-198). Royal Society of Chemistry, Cambridge.

    Google Scholar 

  • van Doorn HE, van der Kruk GC, van Holst G-J, Raaijmakers-Ruijs NCME, Postma E, Groeneweg B & Jongen WHF (1998) The glucosinolates sinigrin and progoitrin are important determinants for taste preference and bitterness of Brussels sprouts. J. Sci. Food Agric. 78: 30-38.

    Article  CAS  Google Scholar 

  • van Poppel G, Verhoeven DT, Verhagen H & Goldbohm RA (1999) Brassica vegetables and cancer prevention. Epidemiology and mechanisms. Adv. Exp. Med. Biol. 472: 159-168.

    PubMed  CAS  Google Scholar 

  • Verkerk R, Jongen W & Dekker M (2001) Post-harvest increase of indolyl glucosinolates in response to chopping and storage of Bassica vegtables. J. Sci. Food Agric. 81: 953-958.

    Article  CAS  Google Scholar 

  • Xu K & Thornalley PJ (1999) Inhibition of leukaemia growth and apoptosis induced by phenetyl isothiocyanate and cysteine conjugate. Brit. J. Cancer 81: 574-575.

    Google Scholar 

  • Xu K & Thornalley PJ (2000) Studies on the mechanism of the inhibition of human leukaemia cell growth by dietary isothiocyanates and their cysteine adducts in vitro. Biochem. Pharmacol. 60: 221-231.

    Article  PubMed  CAS  Google Scholar 

  • Yu R, Jiao JJ, Duh JL, Tan TH & Kong AN (1996) Phenethyl isothiocyanate, a natural chemopreventive agent, activates c-Jun N-terminal kinase 1. Cancer Res. 56: 2954-2959.

    PubMed  CAS  Google Scholar 

  • Yu R, Mandlekar S, Harvey KJ, Ucker DS & Kong AN (1998) Chemopreventive isothiocyanates induce apoptosis and caspase-3-like protease activity. Cancer Res. 58: 402-408.

    PubMed  CAS  Google Scholar 

  • Zhao B, Seow A, Lee EJ, Poh WT, Teh M, Eng P, Wang YT, Tan WC, Yu MC & Lee HP (2001) Dietary Isothiocyanates, Glutathione S-transferase-M1,-T1 Polymorphisms and Lung Cancer Risk among Chinese Women in Singapore. Cancer Epidemiol. Biomarkers Prev. 10: 1063-1067.

    PubMed  CAS  Google Scholar 

  • Zsolnai T (1971) Antimicrobial effects of thiocyanates, isothiocyanates and potential isothiocyanate forming substances. Arzneimittelforschung 21: 121-127.

    PubMed  CAS  Google Scholar 

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Johnson, I. Glucosinolates in the human diet. Bioavailability and implications for health. Phytochemistry Reviews 1, 183–188 (2002). https://doi.org/10.1023/A:1022507300374

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  • DOI: https://doi.org/10.1023/A:1022507300374