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

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13 Citations (Scopus)

Abstract

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
JournalMolecules
Volume21
Issue number5
DOIs
Publication statusPublished - 2016 May 1

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

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  • Cite this

    Kim, H. M., Lee, J. S., Sezirahiga, J., Kwon, J., Jeong, M., Lee, D., Choi, J. H., & Jang, D. S. (2016). A new canthinone-type alkaloid isolated from Ailanthus altissima Swingle. Molecules, 21(5), [642]. https://doi.org/10.3390/molecules21050642