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Cited by 1,682Genomics, phytochemicals, and oxidative stressBioactive Compounds and Antitumor AgentsGlutathione Transferases and Polymorphisms

A major inducer of anticarcinogenic protective enzymes from broccoli: Isolation and elucidation of structure

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Zhang, Y, Talalay, P, Cho, C G, Posner, G H·1992·Proceedings of the National Academy of Sciences
DOI 10.1073/pnas.89.6.2399PMC PMC48665
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Abstract

Consumption of vegetables, especially crucifers, reduces the risk of developing cancer. Although the mechanisms of this protection are unclear, feeding of vegetables induces enzymes of xenobiotic metabolism and thereby accelerates the metabolic disposal of xenobiotics. Induction of phase II detoxication enzymes, such as quinone reductase [NAD(P)H:(quinone-acceptor) oxidoreductase, EC 1.6.99.2] and glutathione S-transferases (EC 2.5.1.18) in rodent tissues affords protection against carcinogens and other toxic electrophiles. To determine whether enzyme induction is responsible for the protective properties of vegetables in humans requires isolation of enzyme inducers from these sources. By monitoring quinone reductase induction in cultured murine hepatoma cells as the biological assay, we have isolated and identified (-)-1-isothiocyanato-(4R)-(methylsulfinyl)butane [CH3-SO-(CH2)4-NCS, sulforaphane] as a major and very potent phase II enzyme inducer in SAGA broccoli (Brassica oleracea italica). Sulforaphane is a monofunctional inducer, like other anticarcinogenic isothiocyanates, and induces phase II enzymes selectively without the induction of aryl hydrocarbon receptor-dependent cytochromes P-450 (phase I enzymes). To elucidate the structural features responsible for the high inducer potency of sulforaphane, we synthesized racemic sulforaphane and analogues differing in the oxidation state of sulfur and the number of methylene groups: CH3-SOm-(CH2)n-NCS, where m = 0, 1, or 2 and n = 3, 4, or 5, and measured their inducer potencies in murine hepatoma cells. Sulforaphane is the most potent inducer, and the presence of oxygen on sulfur enhances potency. Sulforaphane and its sulfide and sulfone analogues induced both quinone reductase and glutathione transferase activities in several mouse tissues. The induction of detoxication enzymes by sulforaphane may be a significant component of the anticarcinogenic action of broccoli.

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  1. [6]Williams, R. T. (1967) Fed. Proc. Fed. Am. Soc. Exp. Biol. 26, 1029-1039.
  2. [7]Miller, E. C. & Miller, J. A. (1985) in Bioactivation of Foreign Compounds, ed. Anders, M. W. (Academic, Orlando, FL), pp. 3-28.
  3. [20]Talalay, P., De Long, M. J. & Prochaska, H. J. (1988) Proc. Natl. Acad. Sci. USA 85, 8261–8265.
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  6. [23]De Long, M. J., Prochaska, H. J. & Talalay, P. (1986) Proc. Natl. Acad. Sci. USA 83, 787–791.
  7. [58]Conney, A. H., Pantuck, E. J., Hsiao, K.-C., Kuntzman, R., Alvares, A. P. & Kappas, A. (1977) Fed. Proc. Fed. Am. Soc. Exp. Biol. 36, 1647–1652.

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Authors
Zhang, Y., Talalay, P., Cho, C. G., & Posner, G. H.
Affiliations
Johns Hopkins University (US)
ORCID
Venue
Proceedings of the National Academy of Sciences
Publisher
National Academy of Sciences
Published
1992-03-15
Volume
89
Issue
6
Pages
2399-2403
ISSN
  • 0027-8424 (ISSN-L)
  • 1091-6490
DOI
10.1073/pnas.89.6.2399
PMC
PMC48665
OpenAlex
W1967077010
Cited by
1,682
References
19
Citations by year
2026: 19 · 2025: 37 · 2024: 39 · 2023: 41 · 2022: 38 · 2021: 51 · 2020: 51 · 2019: 57 · 2018: 67 · 2017: 60 · 2016: 73 · 2015: 72 · 2014: 73 · 2013: 73 · 2012: 82
FWCI
8.07
Type
journal article
Language
en
Open access
Locations
  • Proceedings of the National Academy of Sciences (publishedVersion)
  • PubMed Central (publishedVersion)
  • PubMed (publishedVersion)
Funders
  • American Institute for Cancer Research
  • Johns Hopkins University
  • National Institutes of Health (5p01ca044530-13)
  • National Cancer Institute (P01CA44530)
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Genomics, phytochemicals, and oxidative stress
  • Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Bioactive Compounds and Antitumor Agents
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Glutathione Transferases and Polymorphisms
Keywords
sulforaphane, broccoli, Brassica oleracea italica, quinone reductase, glutathione S-transferase, phase II enzyme induction, isothiocyanates, anticarcinogenic activity, structure-activity relationship, sulfur oxidation state, xenobiotic metabolism, cruciferous vegetables
MeSH terms
Animals, Antineoplastic Agents, Brassica, Cell Line, Chromatography, High Pressure Liquid, Enzyme Induction, Female, Glutathione Transferase, Liver Neoplasms, Experimental, Mice, Inbred Strains, Organ Specificity, Plant Extracts, Mass Spectrometry, Sulfides, Sulfones, Sulfoxides, Thiocyanates, Molecular Structure, NAD(P)H Dehydrogenase (Quinone), Isothiocyanates, Mice

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