Unraveling the Antioxidant Activity of 2R,3R-dihydroquercetin

Abstract

It has been reported that in an oxidative environment, the flavonoid 2R,3R-dihydroquercetin (2R,3R-DHQ) oxidizes into a product that rearranges to form quercetin. As quercetin is a very potent antioxidant, much better than 2R,3R-DHQ, this would be an intriguing form of targeting the antioxidant quercetin. The aim of the present study is to further elaborate on this targeting. We can confirm the previous observation that 2R,3R-DHQ is oxidized by horseradish peroxidase (HRP), with H2O2 as the oxidant. However, HPLC analysis revealed that no quercetin was formed, but instead an unstable oxidation product. The inclusion of glutathione (GSH) during the oxidation process resulted in the formation of a 2R,3R-DHQ-GSH adduct, as was identified using HPLC with IT-TOF/MS detection. GSH adducts appeared on the B-ring of the 2R,3R-DHQ quinone, indicating that during oxidation, the B-ring is oxidized from a catechol to form a quinone group. Ascorbate could reduce the quinone back to 2R,3R-DHQ. No 2S,3R-DHQ was detected after the reduction by ascorbate, indicating that a possible epimerization of 2R,3R-DHQ quinone to 2S,3R-DHQ quinone does not occur. The fact that no epimerization of the oxidized product of 2R,3R-DHQ is observed, and that GSH adducts the oxidized product of 2R,3R-DHQ on the B-ring, led us to conclude that the redox-modulating activity of 2R,3R-DHQ quinone resides in its B-ring. This could be confirmed by chemical calculation. Apparently, the administration of 2R,3R-DHQ in an oxidative environment does not result in ‘biotargeting’ quercetin.

Diastereomers of Spheroidal Form and Commercially Available Taxifolin Samples

“…They are characterized by similar spectral parameters. The UV-spectra profiles of both compounds are characterized by a maximum at 289 nm, which correlates with previously published spectral data of taxifolin [51,52]. The mass spectra of the diastereomers obtained during electrospray ionization show the molecular ion peak at m/z 304 and an intense quasi-molecular ion peak at m/z 303.…”

Tea-Derived Polyphenols Enhance Drought Resistance of Tea Plants (Camellia sinensis) by Alleviating Jasmonate–Isoleucine Pathway and Flavonoid Metabolism Flow

“…Extracts of flavonoids and flavonols from plants are widely used in medicine and are good in vitro antioxidants [44]. The antioxidant capacity of phloretin [45], eriodictyol [46], dihydroquercetin [47], etc., has been verified. CHS is the first key enzyme in the flavonoid metabolic pathway, and drought stress induced significant up-regulation of the CHS gene in thick-headed amaranth.…”