Kim Hye Mi, Lee Jin Su, Sezirahiga Jurdas, Kwon Jaeyoung, Jeong Miran, Lee Dongho, Choi Jung-Hye, Jang Dae Sik
College of Pharmacy, Kyung Hee University, Seoul 130-701, Korea.
Department of Life & Nanopharmaceutical Sciences, Kyung Hee University, Seoul 130-701, Korea.
Molecules. 2016 May 16;21(5):642. doi: 10.3390/molecules21050642.
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.
对臭椿茎皮化学成分的当前研究已分离出六种喹啉酮类生物碱，包括一种新化合物，(R)-5-(1-羟乙基)-喹啉-6-酮(1)，以及五种已知化合物(2-6)。此外，在本研究的同一过程中还分离出四种苯丙素类化合物(7-10)、两种木脂素(11和12)、两种三萜类化合物(13和14)和一种具有已知化学结构的脂肪酸(15)。通过物理性质（熔点、比旋光度）和光谱数据（¹H-NMR、(13)C-NMR、二维NMR和高分辨直接分析实时质谱）解析阐明了新化合物的结构，并通过电子圆二色光谱(ECD)数据和量子化学计算确定了其绝对构型。在RAW 264.7细胞中，对分离出的化合物针对脂多糖(LPS)诱导的促炎介质一氧化氮(NO)的炎症活性进行了筛选。在这些分离出的化合物中，六种化合物对NO生成表现出显著抑制作用,IC50值在5.92±0.9至15.09±1.8μM范围内。
