A New Canthinone-Type Alkaloid Isolated from Ailanthus altissima Swingle

• Main Authors: Hye Mi Kim, Jin Su Lee, Jurdas Sezirahiga, Jaeyoung Kwon, Miran Jeong, Dongho Lee, Jung-Hye Choi, Dae Sik Jang
• Format: Article
• Language: English
• Published: MDPI AG 2016-05-01
• Series: Molecules
• Subjects: Ailanthus altissima; simaroubaceae; canthinone type alkaloids; nitric oxide; inflammation
• Online Access: http://www.mdpi.com/1420-3049/21/5/642

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.