Separation of Quercetin鈥檚 Biological Activity from Its Oxidative Property through Bioisosteric Replacement of the Catecholic Hydroxyl Groups with Fluorine Atoms
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- 作者：Suh Young Cho ; Mi Kyoung Kim ; Hyejung Mok ; Hyunah Choo ; Youhoon Chong
- 刊名：Journal of Agricultural and Food Chemistry
- 出版年：2012
- 出版时间：July 4, 2012
- 年：2012
- 卷：60
- 期：26
- 页码：6499-6506
- 全文大小：359K
- 年卷期：v.60,no.26(July 4, 2012)
- ISSN：1520-5118
文摘
An oxidative property has endowed quercetin with numerous biological benefits, and some of quercetin鈥檚 biological activities may be related, at least partly, to its antioxidant activity. On the other hand, the oxidative property and associated susceptibility to oxidative decomposition has hampered in-depth investigation of the biological targets as well as underlying mechanisms for quercetin鈥檚 biological activity. This study was undertaken to separate quercetin鈥檚 biological activities from its antioxidant properties through bioisosteric replacement of the phenolic hydroxyl groups. The novel quercetin derivative 3鈥?4鈥?difluoroquercetin (2), thus prepared, showed nonoxidizable property with no attenuation of biological activity. Rather, 2 showed a subtle but significant increase in biological activity compared with quercetin, which might be attributed to its lack of oxidative property. The nonoxidizable nature along with the potent biological activity of the quercetin mimic 2 suggests possible oxidation-independent mechanisms for the biological activities of the quercetin that do not require oxidative formation of the highly electrophilic metabolites.