苦参中芳基萘基异戊烯基黄酮和紫檀烷二苯乙烯类化合物的绝对构型和抗癌作用：可能涉及 Wnt 信号通路。
Absolute configuration and anti-cancer effect of prenylated flavonoids and flavonostilbenes from Sophora pachycarpa: Possible involvement of Wnt signaling pathway.
机构信息
Department of Pharmacognosy, School of Pharmacy, Mashhad University of Medical Sciences, Mashhad, Iran.
Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G.C., Evin, Tehran, Iran.
出版信息
Bioorg Chem. 2019 Apr;85:498-504. doi: 10.1016/j.bioorg.2019.01.051. Epub 2019 Feb 6.
A new prenylated flavonostilbene, namely, alopecurone P together with three known compounds sophoraflavanone G, 2-(4-hydroxyphenyl)-2,3-dihydrobenzo[b]furan-3,4,6-triol and alopecurone J were characterized from the roots of Sophora pachycarpa. The absolute configuration of alopecurones J and P were characterized by comparison of experimental electronic circular dichroism (ECD) spectroscopy and simulated data using time-dependent density functional theory (TDDFT) for possible stereoisomers. The cytotoxic properties of isolated compounds have also been evaluated on two breast cancer cell lines (MCF-7 and MDA-MB-231) and normal cell line (NIH/3T3) using AlamarBlue®, flowcytometry and western blot assays. Alopecurone J and P showed cytotoxic effect on MCF-7 cell line through Wnt signaling pathway. It seems that the presence of lavandulyl substitution in C-8 position of flavanone structure increased the cytotoxic effect.
从苦参根部分离得到一个新的苯丙素类化合物，即 alopecurone P，以及三个已知化合物 sophoraflavanone G、2-(4-羟基苯基)-2,3-二氢苯并[b]呋喃-3,4,6-三醇和 alopecurone J。通过比较实验电子圆二色性（ECD）光谱和使用时间相关密度泛函理论（TDDFT）模拟可能的立体异构体，对 alopecurones J 和 P 的绝对构型进行了表征。通过 AlamarBlue®、流式细胞术和 Western blot 分析，还评估了分离得到的化合物对两种乳腺癌细胞系（MCF-7 和 MDA-MB-231）和正常细胞系（NIH/3T3）的细胞毒性。alopecurone J 和 P 通过 Wnt 信号通路对 MCF-7 细胞系表现出细胞毒性作用。似乎在 flavanone 结构的 C-8 位置存在 lavandulyl 取代增加了细胞毒性作用。
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