三叶草叶间苯二酚和烷基苯醌衍生物的细胞毒性和抗炎作用

M. Shahinozzaman, T. Ishii, M. Halim, M. Hossain, M. Islam, S. Tawata
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引用次数: 11

摘要

紫荆属药用植物传统上用于治疗各种人类疾病,包括炎症和癌症。本研究旨在对三叶草叶中细胞毒和抗炎化合物进行纯化和鉴定。生物测定引导色谱分析得到3种化合物,2-甲基-5-(8z -十六烷基)间苯二酚(1),5-(8z -十七烷基)间苯二酚(2)和ardisiaquinone A(3),而液相色谱-电喷雾电离-质谱化学分析显示,在细胞毒性70%甲醇提取物中存在多种间苯二酚和烷基苯醌衍生物。其中1-3的化学结构通过1H NMR(核磁共振)、13C NMR和电喷雾电离质谱等波谱方法得到证实。化合物1和2均为首次从三叶草中分离得到,3个化合物对肿瘤细胞系和卤虾均表现出剂量效应。其中化合物2对癌细胞的IC50值最高(8.8 ~ 25.7 μM),对卤虾的IC50值最高(5.1 μM)。化合物1 ~ 3通过抑制RAW 264.7细胞中蛋白质变性(IC50值为5.8 ~ 9.6 μM)、环氧合酶-2活性(IC50值为34.5 ~ 60.1 μM)和亚硝酸盐形成而具有抗炎作用。本研究中显示的1-3的细胞毒性和抗炎活性值得进一步研究,以考虑其作为候选药物或开发抗癌和抗炎药物的适用性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Cytotoxic and anti-inflammatory resorcinol and alkylbenzoquinone derivatives from the leaves of Ardisia sieboldii
Abstract Medicinal plants belonging to the genus Ardisia are traditionally used to cure various human diseases including inflammation and cancer. This study aimed to purify and characterize cytotoxic and anti-inflammatory compounds from Ardisia sieboldii leaves. Bioassay-guided chromatographic analyses yielded three compounds, 2-methyl-5-(8Z-heptadecenyl) resorcinol (1), 5-(8Z-heptadecenyl) resorcinol (2), and ardisiaquinone A (3), whereas liquid chromatography–electrospray ionisation–mass spectrometry chemical profiling revealed the presence of diverse resorcinol and alkylbenzoquinone derivatives in cytotoxic 70% methanol extracts. Chemical structures of 1–3 were confirmed by spectroscopic methods including 1H NMR (nuclear magnetic resonance), 13C NMR, and electrospray ionisation–mass spectrometry. Compounds 1 and 2 were purified from A. sieboldii for the first time, and all three compounds showed cytotoxicity against a panel of cancer cell lines and brine shrimps in a dose-response manner. Among them, compound 2 exhibited the highest cytotoxicity on cancer cells (IC50 values of 8.8–25.7 μM) as well as on brine shrimps (IC50 value of 5.1 μM). Compounds 1–3 exhibited anti-inflammatory effects through inhibiting protein denaturation (IC50 values of 5.8–9.6 μM), cyclooxygenase-2 activity (IC50 values of 34.5–60.1 μM), and nitrite formation in RAW 264.7 cells. Cytotoxic and anti-inflammatory activities of 1–3 demonstrated in this study deserve further investigation for considering their suitability as candidates or leads to develop anticancer and anti-inflammatory drugs.
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