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 journalArticle

11 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

Fingerprint

Ailanthus
alkaloids
Alkaloids
Nitric Oxide
Nuclear magnetic resonance
nitric oxide
Lignans
nuclear magnetic resonance
Circular Dichroism
Inhibitory Concentration 50
Lipopolysaccharides
Fatty Acids
fatty acids
stems
dichroism
isolation
configurations
cells
electronics

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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

A new canthinone-type alkaloid isolated from Ailanthus altissima Swingle. / Kim, Hye Mi; Lee, Jin Su; Sezirahiga, Jurdas; Kwon, Jaeyoung; Jeong, Miran; Lee, Dongho; Choi, Jung Hye; Jang, Dae Sik.

In: Molecules, Vol. 21, No. 5, 642, 01.05.2016.

Research output: Contribution to journalArticle

Kim, HM, Lee, JS, Sezirahiga, J, Kwon, J, Jeong, M, Lee, D, Choi, JH & Jang, DS 2016, 'A new canthinone-type alkaloid isolated from Ailanthus altissima Swingle', Molecules, vol. 21, no. 5, 642. https://doi.org/10.3390/molecules21050642
Kim, Hye Mi ; Lee, Jin Su ; Sezirahiga, Jurdas ; Kwon, Jaeyoung ; Jeong, Miran ; Lee, Dongho ; Choi, Jung Hye ; Jang, Dae Sik. / A new canthinone-type alkaloid isolated from Ailanthus altissima Swingle. In: Molecules. 2016 ; Vol. 21, No. 5.
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