Characterization of tanshinones with quinone reductase induction activity from Radix Salvia miltiorrhiza by liquid chromatography/tandem mass spectrometry
- 10 August 2009
- journal article
- research article
- Published by Wiley in Rapid Communications in Mass Spectrometry
- Vol. 23 (18), 2857-2866
- https://doi.org/10.1002/rcm.4195
Abstract
Quinone reductase (QR) induction is a reliable biomarker of phase II enzyme induction. In this study, glutathione (GSH) was employed and a liquid chromatography/tandem mass spectrometry (LC/MS/MS) method was introduced to reveal the chemical constituents with QR activity from the ethyl acetate extract of roots Salvia miltiorrhiza (‘Danshen’) and nine tanshinones (9, 13, 17‐19, 21, 24–26), which could conjugate with GSH, were characterized by LC/MS/MS and considered to have QR activities. Then, thirteen tanshinones, including six compounds (17, 18, 21, 24–26) of the above nine tanshinones, were isolated to conduct QR induction evaluation, and it was found that miltirone and its derivatives (18, 20, 24, 26) exhibited significant activities. The GSH conjugate abilities of the isolated tanshinones were also examined; this showed that compounds 18, 20, 24 and 26 had good conjugating abilities with GSH. Compared with the in vitro bioactivity screening results, this proved that conjugate ability is related with QR activity, so an LC/MS/MS method can be applied to find more active compounds. Copyright © 2009 John Wiley & Sons, Ltd.Keywords
This publication has 19 references indexed in Scilit:
- Angelica sinensis and Its Alkylphthalides Induce the Detoxification Enzyme NAD(P)H: Quinone Oxidoreductase 1 by Alkylating Keap1Chemical Research in Toxicology, 2008
- Mechanism of action of isothiocyanates: the induction of ARE-regulated genes is associated with activation of ERK and JNK and the phosphorylation and nuclear translocation of Nrf2Molecular Cancer Therapeutics, 2006
- Quinone Reductase Induction as a Biomarker for Cancer ChemopreventionJournal of Natural Products, 2006
- Screening Method for the Discovery of Potential Cancer Chemoprevention Agents Based on Mass Spectrometric Detection of Alkylated Keap1Analytical Chemistry, 2005
- Transcription Factor Nrf2 Coordinately Regulates a Group of Oxidative Stress-inducible Genes in MacrophagesJournal of Biological Chemistry, 2000
- Diterpenoids from Salvia miltiorrhizaPhytochemistry, 2000
- Diterpenoids from Salvia miltiorrhizaPhytochemistry, 1991
- Abietane type diterpenoids from Salvia miltiorrhizaPhytochemistry, 1989
- Isolation and Bioactivity of New TanshinonesJournal of Natural Products, 1987
- Increase of NAD(P)H:quinone reductase by dietary antioxidants: possible role in protection against carcinogenesis and toxicity.Proceedings of the National Academy of Sciences of the United States of America, 1980