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Molecules 2016, 21(5), 642;

A New Canthinone-Type Alkaloid Isolated from Ailanthus altissima Swingle

College of Pharmacy, Kyung Hee University, Seoul 130-701, Korea
Department of Life & Nanopharmaceutical Sciences, Kyung Hee University, Seoul 130-701, Korea
Department of Biosystems and Biotechnology, College of Life Sciences and Biotechnology, Korea University, Seoul 136-713, Korea
Author to whom correspondence should be addressed.
Academic Editor: Isabel C. F. R. Ferreira
Received: 16 March 2016 / Revised: 11 May 2016 / Accepted: 12 May 2016 / Published: 16 May 2016
(This article belongs to the Collection Bioactive Compounds)
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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 (26). Moreover, four phenyl propanoids (710), 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. View Full-Text
Keywords: Ailanthus altissima; simaroubaceae; canthinone type alkaloids; nitric oxide; inflammation Ailanthus altissima; simaroubaceae; canthinone type alkaloids; nitric oxide; inflammation

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Kim, H.M.; Lee, J.S.; Sezirahiga, J.; Kwon, J.; Jeong, M.; Lee, D.; Choi, J.-H.; Jang, D.S. A New Canthinone-Type Alkaloid Isolated from Ailanthus altissima Swingle. Molecules 2016, 21, 642.

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