State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China.
Food Chem. 2012 Dec 1;135(3):1011-9. doi: 10.1016/j.foodchem.2012.05.074. Epub 2012 May 26.
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 radical-scavenging, 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.
设计并合成了 5 种 5-羟苯基菲作为“顺式构型固定”白藜芦醇类似物，它们在羟基的数量和位置上有所不同。通过铁还原抗氧化能力、2,2-二苯基-1-苦基肼自由基清除和 DNA 链断裂抑制试验研究了它们的抗氧化活性，分别对应于它们的供电子、氢转移和 DNA 保护能力。在上述试验中，它们的活性显著依赖于羟基的数量和位置，并且大多数比白藜芦醇更有效。值得注意的是，具有与白藜芦醇相同的羟基取代的化合物 9b（2,4,6-三羟基菲）优于参考化合物，突出了在多个芳环上延伸共轭的重要性。在不同的实验模型中获得了相似的活性序列，但明显的差异可能有助于深入了解抗氧化机制。基于这些结果，羟苯基菲可能被认为是一种新型的白藜芦醇导向抗氧化剂。
