Comparison of the Bioactivity of Two Glucoraphanin Hydrolysis Products Found in Broccoli, Sulforaphane and Sulforaphane Nitrile

Epidemiological and laboratory studies suggest that dietary broccoli may prevent or delay a variety of cancers. Broccoli and other crucifers contain a relatively unique family of secondary metabolites called glucosinolates. Glucoraphanin, the major glucosinolate in broccoli, is hydrolyzed by an endo...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2001-12, Vol.49 (12), p.5743-5749
Main Authors: Matusheski, Nathan V, Jeffery, Elizabeth H
Format: Article
Language:English
Subjects:
Animals
Anticarcinogenic Agents - pharmacokinetics
Antioxidants
Biological and medical sciences
Brassica - chemistry
Colon - enzymology
General pharmacology
Glucose - analogs & derivatives
Glucose - metabolism
Glucose - pharmacokinetics
Glucosinolates
Glutathione Transferase - metabolism
Hydrolysis
Hydroquinones - pharmacology
Imidoesters - metabolism
Imidoesters - pharmacokinetics
Isothiocyanates
Liver - enzymology
Male
Medical sciences
NAD(P)H Dehydrogenase (Quinone) - metabolism
Nitriles - analysis
Pancreas - enzymology
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Rats
Rats, Inbred F344
Thiocyanates - analysis
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Summary:Epidemiological and laboratory studies suggest that dietary broccoli may prevent or delay a variety of cancers. Broccoli and other crucifers contain a relatively unique family of secondary metabolites called glucosinolates. Glucoraphanin, the major glucosinolate in broccoli, is hydrolyzed by an endogenous plant myrosinase to form either the potent anticarcinogen sulforaphane (SF) or sulforaphane nitrile (SF nitrile). The bioactivities of SF and SF nitrile were compared in rats and in mouse hepatoma cells. Male, 4-week-old, Fischer 344 rats were administered SF or SF nitrile (200, 500, or 1000 μmol/kg) by gavage daily for 5 days. Hepatic, colonic mucosal, and pancreatic quinone reductase and glutathione S-transferase activities were induced by high doses of SF, but not by SF nitrile. When Hepa 1c1c7 cells were exposed to increasing levels of each compound for 24 h, quinone reductase showed a 3-fold maximal induction over control at 2.5 μM SF and a 3.5-fold maximal induction over control at 2000 μM SF nitrile, the highest concentration tested. These results demonstrate that SF nitrile is substantially less potent than SF as an inducing agent of phase II detoxification enzymes. Therefore, glucoraphanin hydrolysis directed toward the production of SF rather than SF nitrile could increase the potential chemoprotective effects of broccoli. Keywords: Broccoli; glucosinolates; sulforaphane; sulforaphane nitrile; isothiocyanate; quinone reductase; glutathione S-transferase; Brassica oleracea
ISSN:0021-8561
1520-5118
DOI:10.1021/jf010809a