Anti-Tmv Isoquinoline Alkaloids from The Whole Plants of Thalictrum glandulosissimum,Heterocycles

当前位置： X-MOL 学术 › Heterocycles › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Anti-Tmv Isoquinoline Alkaloids from The Whole Plants of Thalictrum glandulosissimum
Heterocycles ( IF 0.8 ) Pub Date : 2019-01-01 , DOI: 10.3987/com-19-14142
Chun-Man Song , Qiu-Fen Hu , Guang-Hui Kong , Yu-Ping Wu , Eric Yin , Bradley Liu , Zhen-Yuan Xia , Hai-Tao Huang , Guang-Yu Yang

Three new (1-3), together with three known (4-6) isoquinoline alkaloids were isolated from the whole plants of Thalictrum glandulosissimum. Their structures were elucidated by spectroscopic methods, including extensive 1H, 13C, and 2D-NMR techniques. Compounds 1-6 were evaluated for their anti-tobacco mosaic virus (Anti-TMV) activity. The results revealed that compounds 2, 3 and 4 showed potential anti-TMV activities with inhibition rates of (35.6±3.5)%, (36.2%±3.8)%, (46.3%±3.2)%, at the concentration of 20 μM, respectively. These rates are higher than that of positive control. Thalictrum is a genus of herbaceous perennial flowering plants in the Ranunculaceae (buttercup) family native mostly to temperate regions.1 Various species from the genus Thalictrum have been used for centuries as herbal medicines especially in Russia, Japan and China.2,3 This genus is well known for its diverse pharmacological activities, including anti-tumor, anti-virus, anti-microbial, anti-tuberculosis, anti-inflammatory, anti-malarial activities, and the like.3,4 T. glandulosissimum is a low-growing perennial herb plant belong to Thalictrum genus. It is of 60 85 cm in height, grown in meadow slopes, alpine meadows and river banks at cold plateau in Yunnan province, P. R. China.1 The whole plants of T. glandulosissimum are used to treat some diseases, such as enteritis, dysentery, jaundice and throat by Bai nationality people in Yunnan Province of China.5 Due to their versatile medicinal traditional uses, an increasing number of phytochemical studies have been carried out on this plant, and lot of bioactive natural products, especially some structural biodiversity alkaloids, have been reported.6-9 Therefore, in the course of identifying bioactive compounds from local plants, we now reinvestigated the chemical constituents of the whole plant of T. glandulosissimum collected in Lijiang Prefecture, Yunnan Province. As a results, three new (1-3), together with three known isoquinoline alkaloids (4-6) were isolated in this work. This paper describes the elucidation of the structures of these compounds and a preliminary evaluation of their anti-tobacco mosaic virus (anti-TMV) activity. Figure 1. The isoquinoline alkaloids from the whole plants of T. glandulosissimum A 95% aq. ethanol extract prepared from whole plants of T. glandulosissimum was partitioned between EtOAc and 3% tartaric acid. The aqueous layer was adjusted to pH 9.0 with saturated Na2CO3 aq. and extracted with EtOAc again. The EtOAc-soluble alkaloidal materials were subjected repeatedly to column chromatography on silica gel and preparative HPLC to afford three new isoquinoline alkaloids, 1-(6-methoxy-7-prenylisoquinolin-1-yl)ethanone (1), 1-(6-hydroxy-7-prenylisoquinolin-1-yl)ethanone (2) and 1-(2,2-dimethyl-2H-pyrano[2,3-g]isoquinolin-6-yl)ethanone (3), together with three known isoquinoline alkaloids (4-6). The structures of the compounds 1-6 were shown in Figure 1, and the 1H and 13C NMR data of 1-3 were listed in Table 1. The known compounds, compared with literature, were identified as linearisine (4),10 rugosinone (5),11 and thaliracebine (6).12 Figure 2. Key HMBC ( ) and 1H-1H COSY ( ) correlations of compounds 1-3 Compound 1 was obtained as a yellow gum and assigned the molecular formula C17H19NNaO2 from its HRESIMS at m/z 292.1318 [M+Na]+ (calcd 292.1314). The IR absorption bands indicated the presence of carbonyl (1662 cm-1), and aromatic ring (1614, 1573, and 1442 cm-1) groups. UV absorptions at 222, 268, 302, and 341 nm suggested a conjugated aromatic ring system. Its 1H, 13C, and DEPT NMR data N

更新日期：2019-01-01

点击分享查看原文

点击收藏

阅读更多本刊新发论文本刊介绍/投稿指南