Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity, Team: Medicinal Chemistry and Natural Products, Faculty of Sciences, University of Monastir, Monastir, Tunisia.
Bioorg Med Chem Lett. 2013 Jul 15;23(14):4248-52. doi: 10.1016/j.bmcl.2013.04.081. Epub 2013 May 6.
A phytochemical investigation of the roots of Ferula lutea (Poir.) Maire led to the isolation of new dihydrofuranocoumarins as two inseparable isomers, (-)-5-hydroxyprantschimgin 1 and (-)-5-hydroxydeltoin 2, together with eight known compounds, (-)-prantschimgin 3, (-)-deltoin 4, psoralen 5, xanthotoxin 6, umbelliferone 7, caffeic acid 8, β-sitosterol 9 and stigmasterol 10. Their structures were elucidated on the basis of extensive spectroscopic methods, including 1D and 2D NMR experiments and mass spectroscopy analysis, as well as by comparison with literature data. The anti-acetylcholinesterase and cytotoxic effects of the isolates and antioxidant activities of the mixture (1+2) were also evaluated in this work. Results showed that the mixture (1+2) has the most cytotoxic activity with IC50 values 0.29±0.05 and 1.61±0.57μM against the cell lines HT-29 and HCT 116, respectively. The greatest acetylcholinesterase inhibitory activity (IC50=0.76±0.03) was exhibited by the xanthotoxin 6. In addition, the mixture (1+2) was investigated for its antioxidant activity and showed IC50 values 18.56, 13.06, 7.59, and 4.81μM towards DPPH free radical scavenging, ABTS radical monocation, singlet oxygen and hydrogen peroxide, respectively.
从 Ferula lutea (Poir.) Maire 的根部分离得到两个不可分离的异构体，(-)-5-羟基普拉嗪 1 和 (-)-5-羟基去氧补骨脂素 2，以及另外 8 个已知化合物，(-)-普拉嗪 3、(-)-去氧补骨脂素 4、补骨脂素 5、花椒毒素 6、伞形酮 7、咖啡酸 8、β-谷甾醇 9 和豆甾醇 10。基于广泛的光谱方法，包括 1D 和 2D NMR 实验和质谱分析，并与文献数据进行比较，确定了它们的结构。还评估了这些分离物的抗乙酰胆碱酯酶和细胞毒性作用以及混合物（1+2）的抗氧化活性。结果表明，混合物（1+2）对 HT-29 和 HCT 116 细胞系的 IC50 值分别为 0.29±0.05 和 1.61±0.57μM，具有最强的细胞毒性活性。花椒毒素 6 表现出最强的乙酰胆碱酯酶抑制活性（IC50=0.76±0.03）。此外，还研究了混合物（1+2）的抗氧化活性，其对 DPPH 自由基清除、ABTS 自由基阳离子、单线态氧和过氧化氢的 IC50 值分别为 18.56、13.06、7.59 和 4.81μM。
