Separation of Quercetin's Biological Activity from Its Oxidative Property through Bioisosteric Replacement of the Catecholic Hydroxyl Groups with Fluorine Atoms

Authors
Cho, Suh YoungKim, Mi KyoungMok, HyejungChoo, HyunahChong, Youhoon
Issue Date
2012-07-04
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, v.60, no.26, pp.6499 - 6506
Abstract
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.
Keywords
CELL-CULTURE MEDIA; HYDROGEN-PEROXIDE; ANTIOXIDANT ACTIVITY; IN-VIVO; METABOLISM; ANTIBACTERIAL; POLYPHENOLS; PROOXIDANT; GENERATION; EXTRACTS; CELL-CULTURE MEDIA; HYDROGEN-PEROXIDE; ANTIOXIDANT ACTIVITY; IN-VIVO; METABOLISM; ANTIBACTERIAL; POLYPHENOLS; PROOXIDANT; GENERATION; EXTRACTS; quercetin; oxidative property; bioisostere; antiproliferative effect; antibacterial effect
ISSN
0021-8561
URI
https://pubs.kist.re.kr/handle/201004/129073
DOI
10.1021/jf3018645
Appears in Collections:
KIST Article > 2012
Files in This Item:
There are no files associated with this item.
Export
RIS (EndNote)
XLS (Excel)
XML

qrcode

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

BROWSE