Journal Article

7-Methylsulfinylheptyl and 8-methylsulfinyloctyl isothiocyanates from watercress are potent inducers of phase II enzymes

Peter Rose, Kathy Faulkner, Gary Williamson and Richard Mithen

in Carcinogenesis

Volume 21, issue 11, pages 1983-1988
Published in print November 2000 | ISSN: 0143-3334
Published online November 2000 | e-ISSN: 1460-2180 | DOI:
7-Methylsulfinylheptyl and 8-methylsulfinyloctyl isothiocyanates from watercress are potent inducers of phase II enzymes

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Watercress is an exceptionally rich dietary source of β-phenylethyl isothiocyanate (PEITC). This compound inhibits phase I enzymes, which are responsible for the activation of many carcinogens in animals, and induces phase II enzymes, which are associated with enhanced excretion of carcinogens. In this study, we show that watercress extracts are potent inducers of quinone reductase (QR) in murine hepatoma Hepa 1c1c7 cells, a widely adopted assay for measuring phase II enzyme induction. However, contrary to expectations, this induction was not associated with PEITC (which is rapidly lost to the atmosphere upon tissue disruption due to its volatility) or a naturally occurring PEITC–glutathione conjugate, but with 7-methylsulfinyheptyl and 8-methylsulfinyloctyl isothiocyanates (ITCs). While it was confirmed that PEITC does induce QR (5 μM required for a two-fold induction in QR), 7-methylsulfinyheptyl and 8-methylsulfinyloctyl ITCs were more potent inducers (0.2 μM and 0.5 μM, respectively, required for a two-fold induction in QR). Thus, while watercress contains three times more phenylethyl glucosinolate than methylsulfinylalkyl glucosinolates, ITCs derived from methylsulfinylalkyl glucosinolates may be more important phase II enzyme inducers than PEITC, having 10 - to 25-fold greater potency. Analysis of urine by liquid chromatography–mass spectroscopy (LC-MS) following consumption of watercress demonstrated the presence of N-acetylcysteine conjugates of 7-methylsulfinylheptyl, 8-methylsulfinyloctyl ITCs and PEITC, indicating that these ITCs are taken up by the gut and metabolized in the body. Watercress may have exceptionally good anticarcinogenic potential, as it combines a potent inhibitor of phase I enzymes (PEITC) with at least three inducers of phase II enzymes (PEITC, 7-methylsulfinylheptyl ITC and 8-methylsulfinyloctyl ITC). The study also demonstrates the application of LC-MS for the detection of complex glucosinolate-derived metabolites in plant extracts and urine.

Keywords: AMSHC, N-Acetyl-S-(N-methylsulfinylheptylthiocarbomyl)-L-cysteine; AMSOC, N-Acetyl-S-(N-methylsulfinyloctylthiocarbomyl)-L-cysteine; APCC, N-Acetyl-S-(N-β-phenylethylthiocarbomyl)-L-cysteine; ITC, isothiocyanate; NKK, 4-(methylnitroamino)-1-(3-pyridyl)-1-butanone; NNAL, 4(methylnitrosamino)-1-(3-pyridyl)-1-butanol; NNAL-Gluc, 4-(methylnitrosamino)-1-(3-pyridyl)but-1-yl]-β-omega-D-glucuronic acid; PEITC, β-phenylethyl isothiocyanate; PTCG, S-(N-β-phenylethylthiocarbomyl) glutathione; QR, quinone reductase; SIM, single ion monitoring.

Journal Article.  4360 words.  Illustrated.

Subjects: Clinical Cytogenetics and Molecular Genetics

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