Next Article in Journal
MASM, a Matrine Derivative, Offers Radioprotection by Modulating Lethal Total-Body Irradiation-Induced Multiple Signaling Pathways in Wistar Rats
Next Article in Special Issue
Phenolic Profile and Antioxidant Potential of Leaves from Selected Cotoneaster Medik. Species
Previous Article in Journal
Reversible Immobilization of Lipases on Heterofunctional Octyl-Amino Agarose Beads Prevents Enzyme Desorption
Previous Article in Special Issue
Protective Effects of Dihydromyricetin against •OH-Induced Mesenchymal Stem Cells Damage and Mechanistic Chemistry
Article Menu
Issue 5 (May) cover image

Export Article

Open AccessArticle
Molecules 2016, 21(5), 642; doi:10.3390/molecules21050642

A New Canthinone-Type Alkaloid Isolated from Ailanthus altissima Swingle

1
College of Pharmacy, Kyung Hee University, Seoul 130-701, Korea
2
Department of Life & Nanopharmaceutical Sciences, Kyung Hee University, Seoul 130-701, Korea
3
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)
View Full-Text   |   Download PDF [963 KB, uploaded 16 May 2016]   |  

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 (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
Figures

Figure 1

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).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top