Evaluation of the structure-activity relationship of flavonoids as antioxidants and toxicants of zebrafish larvae

Food Chemistry
Yau-Hung ChenTzenge-Lien Shih

Abstract

The antioxidant ability of an array of commercially available flavonoids was evaluated on the larvae of the zebrafish model organism, in order to find flavonoids with lower toxicities and higher radical oxygen-scavenging properties than flavone. Among the flavonoids tested, chrysin and morin possessed higher reactive oxygen species (ROS)-scavenging rates (-99% and -101%, respectively) and lower toxicity (LD(50)>100 ppm). Zebrafish fins in the UVB+chrysin group were 6.30 times more likely to grow to normal fin size than those in the UVB-only control group, while zebrafish fins in the UVB+morin group were 11.9 times more likely to grow to normal fin size than those in the UVB-only control group. These results were analysed by the QSAR method and were in accordance with predicted values. A new 4'-fluoroflavone was synthesised. The ROS-scavenging rate of 4'-fluoroflavone was -54%, which corresponds well with the predicted value (-48%). We propose that a combination of QSAR prediction and the zebrafish model organism is efficient for evaluating new flavonoids.

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Citations

Apr 16, 2014·Luminescence : the Journal of Biological and Chemical Luminescence·Paweł BerczyńskiRahmiye Ertan
Jul 30, 2014·Journal of Receptor and Signal Transduction Research·Thangaraj Sindhu, Pappu Srinivasan
Jul 30, 2015·Evidence-based Complementary and Alternative Medicine : ECAM·Nadia FerlazzoMichele Navarra
Jan 18, 2015·Toxicology Letters·Eshvendar Reddy KasalaChandana C Barua
Oct 30, 2016·Toxicological Sciences : an Official Journal of the Society of Toxicology·Sean M BugelRobert L Tanguay
Feb 20, 2016·Nutrients·Deepak Kumar SemwalAlvaro Viljoen
Jul 11, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tzenge-Lien ShihYau-Hung Chen
Oct 30, 2014·Journal of Toxicologic Pathology·Chien-Chung ChengYau-Hung Chen
Jul 17, 2020·Environmental Science and Pollution Research International·Mahsan BeyramiEhsan Oskoueian
Feb 23, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Szabolcs MayerLászló Hazai
Jan 7, 2020·Journal of Nutritional Science and Vitaminology·Lu WangWenbin Dong
Apr 6, 2019·Evidence-based Complementary and Alternative Medicine : ECAM·Akinola Adekoya AlafiatayoNoor Azmi Shaharuddin
Jan 28, 2020·Current Organic Synthesis·Pone K Boniface, Ferreira I Elizabeth
Dec 10, 2016·Journal of Agricultural and Food Chemistry·Jiang LiuWenyu Yang

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