Sesquiterpene coumarins from Ferula szowitsiana and in vitro antileishmanial activity of 7-prenyloxycoumarins against promastigotes
Sesquiterpene coumarins from Ferula szowitsiana and in vitro antileishmanial activity of 7-prenyloxycoumarins against promastigotes
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DOI：
10.1016/j.phytochem.2006.11.002
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发表时间：
2007-02-01
期刊：
影响因子：
3.8
通讯作者：
Pizza, Cosimo
中科院分区：
文献类型：
--
作者：
Iranshahi, Mehrdad;Arfa, Peyman;Pizza, Cosimo
两个新的倍半萜香豆素类化合物，命名为szowitsiacoumarin A（1）和szowitsiacoumarin B（2），一种苯丙素衍生物2-表helmanticine（3），以及九个已知化合物，auraptene（4），umbelliprenin（5），galbanic acid（6），galbanate methyl（7），farnesiferol B（8），farnesiferol C（9），persicasulfide A（10），β-谷甾醇和豆甾醇是从阿魏（Ferulaszoivitsiana）的根中分离得到的。通过广泛的光谱方法，包括1D-（H-1和C-13）和2D-NMR实验（DQF-COSY，HSQC，HMBC和ROESY）以及HR-MALDI-MS分析，对这些化合物的结构进行了鉴定。由于2-epihelinanticine的构型以前仅被部分确定，因此在最近报道的J-基方法的基础上，对其四个立体中心进行了相对构型分析，除了作为主要组分的galbanic acid（6）外，还研究了异戊二烯化香豆素类化合物auraptene（4）和umbelliprenin（5）的抑制活性，和阿魏（伞形科）根的Me 2CO提取物对硕大利什曼原虫的前鞭毛体的作用。温育48小时后，伞形酮和金萝卜素显示出显著的活性，IC 50值分别为4.9 μ g/ml（13.3 μ M）和5.1 μ g/ml（17.1 μ M）。(c)2006爱思唯尔有限公司保留所有权利。
Two new sesquiterpene coumarins, named szowitsiacoumarin A (1) and szowitsiacoumarin B (2), and a phenylpropanoid derivative, 2-epihelmanticine (3), together with nine known compounds, auraptene (4), umbelliprenin (5), galbanic acid (6), methyl galbanate (7), farnesiferol B (8), farnesiferol C (9), persicasulfide A (10), beta-sitosterol and stigmasterol were isolated from the roots of Ferula szoivitsiana. The structures of these compounds were elucidated by extensive spectroscopic methods including 1D-(H-1 and C-13) and 2D-NMR experiments (DQF-COSY, HSQC, HMBC, and ROESY) as well as HR-MALDI-MS analysis. Since the configuration of 2-epihelinanticine was previously only partly determined, a relative configurational analysis of its four stereocenters was carried out on the basis of the recently reported J-based method.The inhibiting activity of prenylated coumarins, auraptene (4) and umbelliprenin (5), in addition to galbanic acid (6), as major component, and of the Me2CO extract of Ferula szowitsiana (Apiaceae) roots has been evaluated against promastigotes of Leishmania major. Umbelliprenin and auraptene showed significant activity with IC50 values of 4.9 mu g/ml (13.3 mu M) and 5.1 mu g/ml (17.1 mu M) after 48 h incubation, respectively. (c) 2006 Elsevier Ltd. All rights reserved.