A New Canthinone-Type Alkaloid Isolated from Ailanthus altissima Swingle.

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, (13)C-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.

DOI: 10.3390/molecules21050642

Extracted Key Phrases

6 Figures and Tables

Cite this paper

@article{Kim2016ANC, title={A New Canthinone-Type Alkaloid Isolated from Ailanthus altissima Swingle.}, author={Hye Mi Kim and Jin Su Lee and Jurdas Sezirahiga and Jaeyoung Kwon and Miran Jeong and Dongho Lee and Jung-Hye Choi and Dae Sik Jang}, journal={Molecules}, year={2016}, volume={21 5} }