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, 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.
Highlights
Ailanthus altissima Swingle (Simaroubaceae), the tree-of-heaven, has been used to treat diarrhea, dysentery, heat ailments, epilepsy, asthma, ophthalmic diseases, and it has been used as an astringent
It was reported that a decoction of A. altissima decreased the production of inflammatory cytokines, TNF, IL-6 and IL-8 as well as NF-κB activation on the phorbol 12-myristate 13-acetate and calcium ionophore A23187 (PMACI)-stimulated human mast cell line, HMC-1 [3]
Dulbecco’s modified Eagle’s minimum essential medium (DMEM), fetal bovine serum (FBS), penicillin, and streptomycin were obtained from Life Technologies Inc. (Grand Island, NY, USA)
Summary
Ailanthus altissima Swingle (Simaroubaceae), the tree-of-heaven, has been used to treat diarrhea, dysentery, heat ailments, epilepsy, asthma, ophthalmic diseases, and it has been used as an astringent. Previous phytochemical investigations of A. altissima revealed the presence of alkaloids, terpenoids, steroids, and flavonoids [5]. Among these compounds, quassinoids and indole and β-carboline alkaloids are common major constituents of A. altissima [6,7,8]. Indole and β-carboline alkaloids have shown inhibitory activity on cyclic adenosine monophosphate (cAMP) phosphodiesterase [12]. Most β-carboline and canthin-6-one alkaloids [13], leishmanicidal activity [14], and gastro-protective effects [15].
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