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Sesquiterpene lactones from Sonchus palustris L. (Asteraceae, Cichorieae)
Phytochemistry ( IF 3.2 ) Pub Date : 2020-02-01 , DOI: 10.1016/j.phytochem.2019.112196 Oleksandr Shulha 1 , Serhat Sezai Çiçek 1 , Simona Piccolella 2 , Lucie Rárová 3 , Miroslav Strnad 3 , Frank Sönnichsen 4 , Severina Pacifico 2 , Christian Zidorn 1
Phytochemistry ( IF 3.2 ) Pub Date : 2020-02-01 , DOI: 10.1016/j.phytochem.2019.112196 Oleksandr Shulha 1 , Serhat Sezai Çiçek 1 , Simona Piccolella 2 , Lucie Rárová 3 , Miroslav Strnad 3 , Frank Sönnichsen 4 , Severina Pacifico 2 , Christian Zidorn 1
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Seven previously undescribed sesquiterpene lactones, three known sesquiterpene lactones (ixerin D, 15-p-hydroxyphenylacetyllactucin, and 15-p-hydroxyphenylacetyllactucin-8-sulfate), and two known quinic acid derivatives (3-O-feruloylquinic acid and 3,5-di-O-caffeoylquinic acid) were isolated from Sonchus palustris L. roots. Four formerly undescribed compounds were elucidated to be 3β,14-dihydroxycostunolide-3-O-β-D-glucopyranosyl-(2-O-p-hydroxyphenylacetyl)-14-O-p-hydroxyphenylacetate, 15-p-methoxyphenylacetyllactucin, 15-p-methoxyphenylacetyllactucin-8-sulfate, and 8-p-hydroxyphenylacetyllactucin-15-sulfate. Additionally, three undescribed conjugates of lactucin and a eudesmanolide type sesquiterpenic acid, sonchpalustrin, 4″-O-methylsonchpalustrin, and isosonchpalustrin, were characterized. The structures of the newly discovered natural products were elucidated using 1D and 2D NMR spectroscopy and UHPLC-HRMS. 15-p-Hydroxyphenylacetyllactucin and 15-p-methoxyphenylacetyllactucin showed significant in vitro cytotoxicity against CEM and BJ cells with IC50 values ranging from 3.9 to 9.8 μM. Compounds 3 and 4 showed also strong anti-inflammatory activity in vitro.
中文翻译：
来自 Sonchus palustris L.（菊科、菊科）的倍半萜内酯
七种先前未描述的倍半萜内酯、三种已知的倍半萜内酯（ixerin D、15-p-羟基苯基乙酰基乳蛋白和 15-p-羟基苯基乙酰基乳蛋白-8-硫酸盐）和两种已知的奎尼酸衍生物（3-O-阿魏酰奎宁酸和 3,5- di-O-caffeoylquinic acid) 是从 Sonchus palustris L. 根中分离出来的。四种以前未描述的化合物被阐明为 3β,14-dihydroxycostunolide-3-O-β-D-glupyranosyl-(2-Op-hydroxyphenylacetyl)-14-Op-hydroxyphenylacetate, 15-p-methoxyphenylacetyllactucin, 15-p-methoxyphenylacetyllactucin- 8-硫酸盐和 8-p-羟基苯基乙酰乳酪素-15-硫酸盐。此外，还表征了三种未描述的乳酸菌素和一种eudesmanolide 型倍半萜酸、sonchpalustrin、4″-O-methylsonchpalustrin 和isosonchpalustrin 的缀合物。使用一维和二维核磁共振光谱和 UHPLC-HRMS 阐明了新发现的天然产物的结构。15-p-Hydroxyphenylacetyllactucin 和 15-p-methoxyphenylacetyllactucin 对 CEM 和 BJ 细胞显示出显着的体外细胞毒性，IC50 值范围为 3.9 到 9.8 μM。化合物 3 和 4 在体外也显示出很强的抗炎活性。
更新日期：2020-02-01
中文翻译：
来自 Sonchus palustris L.（菊科、菊科）的倍半萜内酯
七种先前未描述的倍半萜内酯、三种已知的倍半萜内酯（ixerin D、15-p-羟基苯基乙酰基乳蛋白和 15-p-羟基苯基乙酰基乳蛋白-8-硫酸盐）和两种已知的奎尼酸衍生物（3-O-阿魏酰奎宁酸和 3,5- di-O-caffeoylquinic acid) 是从 Sonchus palustris L. 根中分离出来的。四种以前未描述的化合物被阐明为 3β,14-dihydroxycostunolide-3-O-β-D-glupyranosyl-(2-Op-hydroxyphenylacetyl)-14-Op-hydroxyphenylacetate, 15-p-methoxyphenylacetyllactucin, 15-p-methoxyphenylacetyllactucin- 8-硫酸盐和 8-p-羟基苯基乙酰乳酪素-15-硫酸盐。此外，还表征了三种未描述的乳酸菌素和一种eudesmanolide 型倍半萜酸、sonchpalustrin、4″-O-methylsonchpalustrin 和isosonchpalustrin 的缀合物。使用一维和二维核磁共振光谱和 UHPLC-HRMS 阐明了新发现的天然产物的结构。15-p-Hydroxyphenylacetyllactucin 和 15-p-methoxyphenylacetyllactucin 对 CEM 和 BJ 细胞显示出显着的体外细胞毒性，IC50 值范围为 3.9 到 9.8 μM。化合物 3 和 4 在体外也显示出很强的抗炎活性。
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