A New Canthinone-Type Alkaloid Isolated from Ailanthus altissima Swingle

  • Molecules. 2016 May 16;21(5):642. doi: 10.3390/molecules21050642.
Hye Mi Kim  1 ,  Jin Su Lee  2 ,  Jurdas Sezirahiga  3 ,  Jaeyoung Kwon  4 ,  Miran Jeong  5 ,  Dongho Lee  6 ,  Jung-Hye Choi  7  8 ,  Dae Sik Jang  9  10
Affiliations
  • 1. College of Pharmacy, Kyung Hee University, Seoul 130-701, Korea. [email protected].
  • 2. Department of Life & Nanopharmaceutical Sciences, Kyung Hee University, Seoul 130-701, Korea. [email protected].
  • 3. College of Pharmacy, Kyung Hee University, Seoul 130-701, Korea. [email protected].
  • 4. Department of Biosystems and Biotechnology, College of Life Sciences and Biotechnology, Korea University, Seoul 136-713, Korea. [email protected].
  • 5. Department of Life & Nanopharmaceutical Sciences, Kyung Hee University, Seoul 130-701, Korea. [email protected].
  • 6. Department of Biosystems and Biotechnology, College of Life Sciences and Biotechnology, Korea University, Seoul 136-713, Korea. [email protected].
  • 7. College of Pharmacy, Kyung Hee University, Seoul 130-701, Korea. [email protected].
  • 8. Department of Life & Nanopharmaceutical Sciences, Kyung Hee University, Seoul 130-701, Korea. [email protected].
  • 9. College of Pharmacy, Kyung Hee University, Seoul 130-701, Korea. [email protected].
  • 10. Department of Life & Nanopharmaceutical Sciences, Kyung Hee University, Seoul 130-701, Korea. [email protected].
PMID: 27196883 DOI: 10.3390/molecules21050642
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.

Keywords
Ailanthus altissima; canthinone type alkaloids; inflammation; nitric oxide; simaroubaceae.
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