Three lignans and one coumarinolignoid with quinone reductase activity from Eurycorymbus cavaleriei

Zhongjun Ma*, Xiaoyu Zhang, Lin Cheng, Peng Zhang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

Four compounds, including one new lignan cavaol H (1), one new coumarinolignoid 5′-hydroxycleomiscosin B (4) and two known lignans (2-3) were isolated from the 95% ethanol extract of the twigs of Eurycorymbus cavaleriei. Their structures were established on the basis of various spectroscopic analyses including 1D-(1H, 13C, and DEPT) and 2D-NMR (COSY, HMQC, and HMBC). The absolute stereochemistry of the two known lignans was firstly reported in this article by 1H NMR studies on Mosher's ester derivatives. In the present study, quinone reductase induction activities of compounds 1-4 were assayed, compound 4 showed moderate quinone reductase induction with concentration to double the enzyme activity (CD) of 10.5 ± 0.8 μg/mL. Then we established LC-MS-MS analysis of glutathione (GSH) incubation with compound 4 to explain whether compound 4 induced quinone reductase through alkylating of the sulfhydryl groups of Keap1. Reconstructed selected ion chromatogram (SIC) of m/z 706 after compound 4 incubation with GSH was different from that with Tris-HCl buffer solution, which meant the quinone reductase induction activity of compound 4 attributed to alkylating the sulfhydryl groups of Keap1.

Original languageEnglish (US)
Pages (from-to)320-326
Number of pages7
JournalFitoterapia
Volume80
Issue number6
DOIs
StatePublished - Sep 2009
Externally publishedYes

Keywords

  • Coumarinolignoid
  • GSH conjugate
  • Lignan
  • Quinone reductase induction activity

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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