β-carboline derivatives and diphenols from soy sauce are in vitro quinone reductase (QR) inducers.

Department of Food Science, Babcock Hall, University of Wisconsin-Madison, 1605 Linden Drive, Madison, Wisconsin 53706, United States.

Journal of agricultural and food chemistry 2011 Mar 23

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A murine hepatoma (Hepa 1c1c7) cellular bioassay was used to guide the isolation of phase II enzyme inducers from fermented soy sauce, using quinone reductase (QR) as a biomarker. A crude ethyl acetate extract, accounting for 8.7% of nonsalt soluble solids of soy sauce, was found to double relative QR specific activity at 25 μg/mL (concentration required to double was defined as a "CD value"). Further silica gel column fractionation yielded 17 fractions, 16 of which exhibited CD values for QR induction of <100 μg/mL. The four most potent fractions were subfractionated by column and preparative thin layer chromatography, leading to the isolation and identification of two phenolic compounds (catechol and daidzein) and two β-carbolines (flazin and perlolyrin), with respective CD values of 8, 35, 42, and 2 μM. Western blots confirmed that the increases in QR activity corresponded to dose-dependent increases in cellular levels of NAD[P]H:quinone oxidoreductase 1 protein by these four QR inducers. To the authors' knowledge, this is the first report on the ability of β-carboline-derived alkaloids to induce phase II enzymes.

Citation

Ying Li, Mouming Zhao, Kirk L Parkin. β-carboline derivatives and diphenols from soy sauce are in vitro quinone reductase (QR) inducers. Journal of agricultural and food chemistry. 2011 Mar 23;59(6):2332-40