Characterization of bioactive thiophenes from the dichloromethane extract of Echinops grijisii as Michael addition acceptors

Xiaoyu Zhang, Zhongjun Ma*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Scopus citations


Michael addition acceptors are considered as biologically active molecules, which regulate many signal pathways in cells. In the present study, it was demonstrated that the dichloromethane extract of Echinops grijisii had phase II detoxifying enzyme-inducing and nuclear factor-κB (NF-κB)-inhibiting activities, which might be attributed to the modification of key cysteine residues in Keap1 and NF-κB by Michael addition acceptors in it. To screen these Michael addition acceptors, glutathione (GSH) was employed, and a simple liquid chromatography-tandem mass spectrometry screening method was established to investigate the formation of GSH conjugates. Three thiophenes, 5-(penta-1,3-diynyl)-2-(3,4-diacetoxybut-1-ynyl)-thiophene (6), 2-(penta-1,3-diynyl)-5-(4-hydroxybut-1-ynyl)-thiophene (7), and 2-(penta-1,3-diynyl)-5-(3,4-dihydroxybut-1-ynyl)-thiophene (8) were demonstrated to react with GSH. Then NAD(P)H/quinone oxidoreductase1(NQO1) induction assay and an ultrafiltration mass spectrometric screening method were performed to investigate whether the above three compounds had NQO1-inducing and NF-κB (p65) alkylating activities. The result indicated that compounds 6-8, which had a common structural moiety, a penta-1,3-diynyl group, had strong NQO1-inducing activities, and compounds 7 and 8 could effectively alkylate the cysteine residues in NF-κB (p65).

Original languageEnglish (US)
Pages (from-to)1975-1984
Number of pages10
JournalAnalytical and Bioanalytical Chemistry
Issue number5
StatePublished - Jul 2010
Externally publishedYes


  • Dichloromethane extract of Echinops grijisii
  • Glutathione
  • LC-MS screening
  • Michael addition acceptors
  • Thiophenes

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry


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