A new canthinone-type alkaloid isolated from Ailanthus altissima Swingle

Hye Mi Kim, Jin Su Lee, Jurdas Sezirahiga, Jaeyoung Kwon, Miran Jeong, Dongho Lee, Jung Hye Choi, Dae Sik Jang

Research output: Contribution to journalArticlepeer-review

38 Citations (Scopus)


The present investigation of the chemical constituents of the stem barks of Ailanthus altissima has resulted in the isolation of six canthinone-type alkaloids, including a new compound, (R)-5-(1-hydroxyethyl)-canthine-6-one (1), and five known compounds (2-6). Moreover, four phenyl propanoids (7-10), two lignans (11 and 12), two triterpenoids (13 and 14) and a fatty acid (15) having previously known chemical structures were isolated during the same course of this study. The structure of the new compound was elucidated by physical (m.p., [α]D) and spectroscopic data (1H-NMR, 13C-NMR, 2D NMR, and HR-DART-MS) interpretation and its absolute configuration was determined by electronic circular dichroism (ECD) data and quantum chemical calculations. The inflammatory activities of the isolates were screened on lipopolysaccharide (LPS)-induced nitric oxide (NO), a proinflammatory mediator, in RAW 264.7 cells. Among these isolated compounds, six compounds exhibited significant inhibition of NO production, with IC50 values in the range of 5.92 ± 0.9 to 15.09 ± 1.8 μM.

Original languageEnglish
Article number642
Issue number5
Publication statusPublished - 2016 May 1

Bibliographical note

Funding Information:
This work was supported by the Bio-Synergy Research Project (NRF-2014M3A9C4066594) of the Ministry of Science, ICT, and Future Planning through the National Research Foundation and by High Value-added Food Technology Development Program, Korea Institute of Planning and Evaluation for Technology in Food, Agriculture, Forestry, and Fisheries (113036-04-1-HD020).

Publisher Copyright:
© 2016 by the authors; licensee MDPI.


  • Ailanthus altissima
  • Canthinone type alkaloids
  • Inflammation
  • Nitric oxide
  • Simaroubaceae

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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