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三羟异黄酮从鱼藤(Roxb.)本斯和他们的癌症化学预防活性和体外抗增殖作用。

Three isoflavones from Derris scandens (Roxb.) Benth and their cancer chemopreventive activity and in vitro antiproliferative effects.

机构信息

Faculty of Pharmacy, Meijo University, Tempaku, Nagoya, 468-8503, Japan.

Faculty of Pharmacy, Meijo University, Tempaku, Nagoya, 468-8503, Japan; Department of Physiology, School of Medicine, Aichi Medical University, 1-1 Yazakokarimata, Nagakute, Aichi, 480‒1195, Japan.

出版信息

Phytochemistry. 2020 Jul;175:112376. doi: 10.1016/j.phytochem.2020.112376. Epub 2020 Apr 15.

Abstract

Three undescribed isoflavones, derriscandenon A, B, and C, together with seven known isoflavones were isolated and structurally characterized during a study of the chemical constituents in the leaves of Derris scandens (Roxb.) Benth (Leguminosae, Fabaceae) collected in Bangladesh. The inhibitory activity of the compounds against activation of Epstein-Barr virus antigen (EBV-EA) by 12-O-tetradecanoylphorbo-13-acetate (TPA) was measured to identify possible chemopreventive agents. Mild inhibitory effects (IC 278-290 mol ratio/32 pmol TPA) against EBV-EA induction compared with curcumin (IC 341 mol ratio/32 pmol TPA) were observed for four known compounds (lupalbigenin, isopalbigenin, glyurallin, and isangustone A). Next, we focused on antitumor effects and investigated cell viability, cell proliferation, and mitochondria membrane potential by using an MTT assay, a live cell monitoring system, and fluorescence staining. Of the seven isoflavones tested for cell viability, a dose-dependent decrease in cell viability was observed for four isoflavones (derriscandenon B and C, derrubone, and glyurallin) in KB cells and two compounds (derriscandenon B and isochandaisone) in NALM6-MSH+ cells. In addition, the proliferation of KB cells was significantly inhibited by these four compounds at a concentration of 5 μM. The mitochondria membrane potentials of KB cells treated with derriscandenon C, derrubone, and glyurallin at the IC concentration were decreased by about 55%, whereas undescribed compound derriscandenon B had no effect. Our results show that some of the compounds isolated from D. scandens may be suitable as seed compounds for cancer prevention and therapy.

摘要

三种未被描述的异黄酮,即 derriscandenon A、B 和 C,以及七种已知的异黄酮,在对孟加拉国采集的 privet(豆科、蝶形花科)叶片中的化学成分进行研究时被分离并进行了结构鉴定。为了寻找可能的化学预防剂,测量了这些化合物对 12-O-十四烷酰佛波醇-13-乙酸酯(TPA)激活 Epstein-Barr 病毒抗原(EBV-EA)的抑制活性。与姜黄素(IC 341 mol ratio/32 pmol TPA)相比,四种已知化合物(lupalbigenin、isopalbigenin、glyurallin 和 isangustone A)对 EBV-EA 诱导的抑制作用较弱(IC 278-290 mol ratio/32 pmol TPA)。接下来,我们将重点放在抗肿瘤作用上,并通过 MTT 测定、活细胞监测系统和荧光染色来研究细胞活力、细胞增殖和线粒体膜电位。在对七种异黄酮进行细胞活力测试中,在 KB 细胞中,四种异黄酮(derriscandenon B 和 C、derrubone 和 glyurallin)和在 NALM6-MSH+细胞中两种化合物(derriscandenon B 和 isochandaisone)的细胞活力呈剂量依赖性下降。此外,在 5 μM 浓度下,这四种化合物显著抑制了 KB 细胞的增殖。在 IC 浓度下,KB 细胞中 derriscandenon C、derrubone 和 glyurallin 的线粒体膜电位降低了约 55%,而未被描述的化合物 derriscandenon B 则没有影响。我们的结果表明,从 privet 中分离得到的一些化合物可能适合作为癌症预防和治疗的起始化合物。

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