A New Canthinone-Type Alkaloid Isolated from Ailanthus altissima Swingle

Abstract

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 ( 1 H-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 IC 50 values in the range of 5.92˘0.9 to 15.09˘1.8 µM.

LC‐HRMS for the Identification of β‐Carboline and Canthinone Alkaloids Isolated from Natural Sources

“…10-Hydroxy-antirhine N- 11-Hydroxycanthin-6-one-N-oxide Simaroubaceae: Simarouba berteroana Krug & Urban [25] 9-Hydroxycanthin-6-one-N-oxide Simaroubaceae: S. berteroana [25] (R)-5-(1-Hydroxyethyl)canthine-6-one Simaroubaceae: Ailanthus altissima Swingle [18] 10-hydroxy-iso-deppeaninol Rubiaceae: Psychotria prunifolia (Kunth) Steyerm. [29] 1-Hydroxy-11methoxycanthin-6-one Simaroubaceae: Eurycoma longifolia Jack [24] 10-Hydroxy-9methoxycanthin-6-one Simaroubaceae: E. longifolia [21,24] 11-Hydroxy-1methoxycanthin-6-one Simaroubaceae: E. longifolia [21] 11-Hydroxy-10methoxycanthin-6-one Simaroubaceae: E. longifolia [24] 5-Hydroxy-…”

Anti-Inflammatory Activity and ROS Regulation Effect of Sinapaldehyde in LPS-Stimulated RAW 264.7 Macrophages

“…Sinapaldehyde (SNAH) is a methoxyphenol found in several plants such as Senra incan [ 21 ], Ailanthus altissima Swingle [ 22 ], Eucalyptus globulus [ 23 ], Oryza sativa [ 24 ], Dendropanax dentiger [ 25 ], and Populus tomentosa [ 26 ]. It was reported that SNAH exerts antibacterial activities against oral pathogenic bacteria, including Streptococcus pyogenes , Streptococcus mitis , and Streptococcus mutans [ 27 ].…”

…Fell Upas Sits, the Hydra-Tree of Death †, or the Phytotoxicity of Trees

“…The tissues of various Ailanthus species contain a large number of biologically active compounds, such as alkaloids, terpenoids, steroids, flavonoids, and volatile oils—about 200 in total [37]. Studies periodically discover new ones, for example, in the A. altissima bark [161] or fruits [162]. Among them, the quassinoids stand out and represent highly oxygenated degraded triterpenes with a bitter taste, which can be found only in the Simaroubaceae family.…”