Cho, Suh Young Kim, Mi Kyoung Mok, Hyejung Choo, Hyunah Chong, Youhoon 2024-01-20T14:31:12Z 2024-01-20T14:31:12Z 2021-09-05 2012-07-04 0021-8561 https://pubs.kist.re.kr/handle/201004/129073 An oxidative property has endowed quercetin with numerous biological benefits, and some of quercetin's 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's biological activity. This study was undertaken to separate quercetin's biological activities from its antioxidant properties through bioisosteric replacement of the phenolic hydroxyl groups. The novel quercetin derivative 3',4'-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. English AMER CHEMICAL SOC CELL-CULTURE MEDIA HYDROGEN-PEROXIDE ANTIOXIDANT ACTIVITY IN-VIVO METABOLISM ANTIBACTERIAL POLYPHENOLS PROOXIDANT GENERATION EXTRACTS Separation of Quercetin's Biological Activity from Its Oxidative Property through Bioisosteric Replacement of the Catecholic Hydroxyl Groups with Fluorine Atoms Article 10.1021/jf3018645 1 JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, v.60, no.26, pp.6499 - 6506 JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 60 26 6499 6506 scie scopus 000305863800006 2-s2.0-84863449358 Agriculture, Multidisciplinary Chemistry, Applied Food Science & Technology Agriculture Chemistry Food Science & Technology Article CELL-CULTURE MEDIA HYDROGEN-PEROXIDE ANTIOXIDANT ACTIVITY IN-VIVO METABOLISM ANTIBACTERIAL POLYPHENOLS PROOXIDANT GENERATION EXTRACTS quercetin oxidative property bioisostere antiproliferative effect antibacterial effect