Tetrahydroprotoberberine N-oxides from Chelidonium majus and their inhibitory effects on NO production in RAW 264.7 cells

Thi Phuong Linh Le, Jin Woo Lee, Jun Gu Kim, Jae Sang Han, Haeun Kwon, Dongho Lee, Mi Kyeong Lee, Bang Yeon Hwang

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)


Two new tetrahydroprotoberberine N-oxides, 7R,14S-cis-tetrahydrocoptisine N-oxide (1) and 7R,14R-trans-tetrahydrocoptisine N-oxide (2) along with fourteen known compounds (3–16) were isolated from the aerial parts of Chelidonium majus. Their structures were elucidated by spectroscopic and spectrometric methods, such as 1D and 2D-NMR (HSQC, HMBC, NOESY) and HRESIMS. The absolute configurations of 1 and 2 were established by comparison of their experimental and calculated ECD data. All isolates were evaluated for their inhibitory effects on the nitric oxide production in LPS-induced RAW 264.7 macrophages, and compounds 2, 6–10, 13, and 15 showed significant inhibitory effects with the IC50 values ranging from 1.1–31.9 μM.

Original languageEnglish
Pages (from-to)38-42
Number of pages5
JournalPhytochemistry Letters
Publication statusPublished - 2021 Feb

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MIST) (No. 2020R1A2C1008406), the Medical Research Center Program (MRC, 2017R1A5A2015541 ) through the National Research Foundation of Korea , and by the Korea Basic Science Institute under the R&D program (Project No. C030440) supervised by the Ministry of Science and ICT.

Publisher Copyright:
© 2020 Phytochemical Society of Europe


  • Chelidonium majus
  • Nitric oxide, tetrahydrocoptisine N-oxide
  • Papaveraceae

ASJC Scopus subject areas

  • Biotechnology
  • Biochemistry
  • Agronomy and Crop Science
  • Plant Science


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