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从泡桐果实中分离得到的新型环状 C-香叶基黄酮及其对三种癌细胞系的抗增殖作用。

New cyclic C-geranylflavanones isolated from Paulownia fortunei fruits with their anti-proliferative effects on three cancer cell lines.

机构信息

School of Parmacy and Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, NHC Key Laboratory of Biotechnology Drugs (Shandong Academy of Medical Sciences), Key Lab for Rare & Uncommon Diseases of Shandong Province, Jinan 250117, China; Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, 24 Tong Jia Xiang, 210009 Nanjing, China.

School of Parmacy and Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, NHC Key Laboratory of Biotechnology Drugs (Shandong Academy of Medical Sciences), Key Lab for Rare & Uncommon Diseases of Shandong Province, Jinan 250117, China.

出版信息

Fitoterapia. 2023 Jul;168:105542. doi: 10.1016/j.fitote.2023.105542. Epub 2023 May 11.

DOI:10.1016/j.fitote.2023.105542
PMID:37172633
Abstract

Seven new C-geranylated flavanones, fortunones F - L (1-7), were isolated from the fresh mature fruits of Paulownia fortunei (Seem.) Hemsl. Their structures were determined by extensive spectroscopic data interpretation (UV, IR, HRMS, NMR, and CD). These new isolated compounds were all with a cyclic side chain modified from the geranyl group. Among them, compounds 1-3 all possessed a dicyclic geranyl modification, which was described firstly for Paulownia C-geranylated flavonoids. All the isolated compounds were subjected to the cytotoxic assay on human lung cancer cell A549, mouse prostate cancer cell RM1 and human bladder cancer cell T24, respectively. Results indicated A549 cell line was more sensitive to C-geranylated flavanones than the other two cancer cell lines and compounds 1, 7 and 8 exhibited potential anti-tumor effects (IC ˂ 10 μM). Further research revealed the effective C-geranylated flavanones could exert their anti-proliferative activity on A549 cells by inducing apoptosis and blocking cells in G1 phase.

摘要

从泡桐(Paulownia fortunei (Seem.) Hemsl.)新鲜成熟果实中分离得到了 7 种新的 C-香叶基化二氢黄酮,分别命名为 fortunones F-L(1-7)。通过广泛的光谱数据分析(UV、IR、HRMS、NMR 和 CD)确定了它们的结构。这些新分离的化合物都具有香叶基环侧链修饰。其中,化合物 1-3 均具有双环香叶基修饰,这是首次在泡桐 C-香叶基化黄酮中描述的。对所有分离得到的化合物进行了人肺癌细胞 A549、小鼠前列腺癌细胞 RM1 和人膀胱癌细胞 T24 的细胞毒性测定。结果表明,C-香叶基化二氢黄酮对 A549 细胞系的敏感性高于其他两种癌细胞系,化合物 1、7 和 8 表现出潜在的抗肿瘤作用(IC<10 μM)。进一步的研究表明,有效的 C-香叶基化二氢黄酮可以通过诱导细胞凋亡和阻止细胞进入 G1 期来发挥其对 A549 细胞的抗增殖活性。

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