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Small Library of Triazolyl Polyphenols Correlating Antioxidant Activity and Stability with Number and Position of Hydroxyl Groups
ACS Combinatorial Science ( IF 3.903 ) Pub Date : 2018-10-29 00:00:00 , DOI: 10.1021/acscombsci.8b00118
M Angeles Bonache 1 , Silvia Moreno-Fernández 2 , Marta Miguel 2 , Beatriz Sabater-Muñoz 3, 4 , Rosario González-Muñiz 1
Affiliation  

Polyphenolic compounds have attracted much interest because of their antioxidant properties and multiple applications, from food or cosmetic preservatives to free radical scavengers as therapeutic agents. Inspired by common OH substitutions in natural products, here we describe a small library of 1,2,3-triazoles disubstituted with polyphenol groups at 1,4-positions, in an attempt to correlate the number and position of hydroxyl groups in the aromatic rings with the antioxidant activity. Some compounds from this library exhibit strong radical scavenging activities in the oxygen radical absorbance capacity assay, similar to or even higher than resveratrol and other well-kwon flavonoids. The antioxidant activity for selected compounds was confirmed in vitro through the 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) test and in vivo by a Saccharomyces cerevisiae model organism assay. The activity depends on the number and position of the hydroxyl groups, with compounds bearing a 2″5″-hydroxyl substituents on the phenyl ring at position 4 showing the best antioxidant values. The presence of two quinone-forming phenolic groups at the same molecule is behind the instability of some of these compounds in aqueous media.

中文翻译:

三唑基多酚的小文库与抗氧化剂的活性和稳定性与羟基的数量和位置相关

多酚化合物因其抗氧化性能和广泛应用而引起了广泛的兴趣,从食品或化妆品防腐剂到自由基清除剂作为治疗剂。受天然产物中常见OH取代的启发,在此我们描述了一个由1,4-位多酚基团双取代的1,2,3-三唑的小型文库,试图关联芳族环中羟基的数量和位置具有抗氧化活性。该库中的某些化合物在氧自由基吸收能力测定中显示出强大的自由基清除活性,与白藜芦醇和其他广为人知的类黄酮相似甚至更高。在体外确认了所选化合物的抗氧化活性通过2,2'- azinobis(3-乙基-6-磺酸盐)试验和体内酿酒酵母的模式生物测定法。活性取决于羟基的数目和位置,其中在位置4的苯环上带有2“ 5”-羟基取代基的化合物显示出最佳的抗氧化剂值。在同一分子中存在两个形成醌的酚基,这是其中一些化合物在水性介质中不稳定的原因。
更新日期:2018-10-29
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