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Synthesis and antioxidant activity of hydroxylated phenanthrenes as cis-restricted resveratrol analogues

Abstract:
   Five hydroxylated phenanthrenes as "cis-configuration-fixed" resveratrol analogues differing in the number and position of the hydroxyl groups were designed and synthesized. Their antioxidant activity was studied by ferric reducing antioxidant power, 2,2-diphenyl-1-picrylhydrazyl free radicalscavenging, and DNA strand breakage-inhibiting assays, corresponding to their electron-donating, hydrogen-transfer and DNA-protecting abilities, respectively. In the above assays, their activity depends significantly on the number and position of the hydroxyl groups, and most of them are more effective than resveratrol. Noticeably, compound 9b (2,4,6-trihydroxyl phenanthrene) with the same hydroxyl group substitutions as resveratrol, is superior to the reference compound, highlighting the importance of extension of the conjugation over multiple aromatic-rings. Similar activity sequences were obtained in different experimental models, but the appreciable differences could contribute detailed insights into antioxidant mechanisms. Based on these results, the hydroxylated phenanthrenes may be considered as a novel type of resveratrol-directed antioxidants.

Research highlights

► “cis-configuration-fixed” resveratrol analogues were designed and synthesized.
► Antioxidant activity of hydroxylated phenanthrenes were studied by different methods.
► This work highlights importance of the conjugation extension in antioxidant activity.

感语：
         惭愧，博士期间的第一篇论文，也是唯一一篇论文。投稿至今刚刚好，一整年。文章数据大概做了一年。老板一直拖着没发。开始动笔到完稿，差不多小半年，那个折腾。被老板骂了无数次，该改了大家4次，可见当初自己写的多差。到了最后，踩着文章的点毕业。收到接受函大家是5月下旬。共投了三个杂志。漫长的等待真是煎熬。确实磨练了心智，是这篇文章带来的最大收获。这里面没有计算的能容，这部分方向也是我们课题组扫尾作了。其他的工作多了点计算，不过都为发表。和大家一块分享心情，分享收获。仅此也纪念，处女座投稿一周年！感谢我的朋友与导师！

      

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