Effect of resveratrol and its hydroxylated analogues on proliferation and apoptosis oftwo cervix cancer derived cancer cell lines. The role of mitochondrial superoxidedismutase

The Open Bioactive Compounds Journal Pub Date : 2013-07-01 DOI:10.2174/1874847320130701002

H. Piotrowska, M. Kucińska, M. Wierzchowski, Urszula Kazmierczak-Majchrzak, M. Murias

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Abstract

The naturally occurring polyphenol resveratrol (3,4',5-trihydroxy-stilbene, 3,4',5-THS, RES) has been shown as a chemopreventive and proapototic agent. Resveratrol is extensively metabolized by CYP450 enzymes. The monohy- droxylation of resveratrol is catalyzed by CYP1B1 to form 3,3',4',5-THS (piceatannol), a metabolite with higher antican- cer activity and stronger antioxidant properties. It was hypothesized that RES analogues (HHRAs) possessing more than 3 hydroxyl groups may act stronger against cancer cells than RES due to reactive oxygen species formed in redox-cycling reactions. In order to investigate a structure-activity relationship between pro/antioxidant properties and cytotoxicity, the HHRAs with at least 2 phenolic groups in neighborhood- 3,4,4',5-HS and 3,3',4,4',5,5'-HS were synthesized. In the present study we tested this hypothesis in a cell culture model using HeLa and C33A cancer cell lines. The results of our experi- ments support a hypothesis that MnSOD overexpressing HeLa cells are much more resistant to superoxide generating HHRAs than C33A cells.

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白藜芦醇及其羟基化类似物对两种宫颈癌源性癌细胞增殖和凋亡的影响。线粒体超氧化物歧化酶的作用

天然存在的多酚白藜芦醇(3,4'，5-三羟基苯乙烯，3,4'，5-THS, RES)已被证明是一种化学预防和促凋亡剂。白藜芦醇被CYP450酶广泛代谢。白藜芦醇的单羟基化反应由CYP1B1催化生成3,3'，4'，5-THS (picetanol)，这是一种具有较高抗癌活性和较强抗氧化性能的代谢物。据推测，具有3个以上羟基的RES类似物(HHRAs)可能比RES对癌细胞的作用更强，这是由于氧化还原循环反应中形成的活性氧。为了研究抗氧化性能与细胞毒性之间的构效关系，合成了邻域- 3,4,4'，5- hs和3,3'，4,4'，5,5'- hs中含有至少2个酚基团的HHRAs。在本研究中，我们在使用HeLa和C33A癌细胞系的细胞培养模型中验证了这一假设。我们的实验结果支持了一种假设，即MnSOD过表达的HeLa细胞比C33A细胞更能抵抗产生超氧化物的HHRAs。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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The Open Bioactive Compounds Journal

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