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

Abstract

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.

• Authors: Ying Li, Mouming Zhao, Kirk L Parkin
• Journal: Journal of agricultural and food chemistry (J Agric Food Chem) Vol. 59 Issue 6 Pg. 2332-40 (Mar 23 2011) ISSN: 1520-5118 [Electronic] United States
• PMID: 21332190 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S.)

Chemical References

• Carbolines
• Plant Extracts
• Phenol
• NAD(P)H Dehydrogenase (Quinone)

Topics

• Animals
• Carbolines (chemistry, isolation & purification, pharmacology)
• Cell Line, Tumor
• Enzyme Activation (drug effects)
• Mice
• NAD(P)H Dehydrogenase (Quinone) (metabolism)
• Phenol (chemistry, isolation & purification, pharmacology)
• Plant Extracts (chemistry, isolation & purification, pharmacology)
• Soy Foods (analysis)