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Preparation of two sets of 5,6,7-trioxygenated dihydroflavonol derivatives as free radical scavengers and neuronal cell protectors to oxidative damage.

Abstract：

:An unusual class of 5,6,7-trioxygenated dihydroflavonols (3a-e and 4a-j) were designed and prepared. Their antioxidative properties were assessed by examining their capacities in several in vitro models, including superoxide anion and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, rat liver homogenate lipid peroxidation inhibition, PC12 cells protection from oxidative damage, and xanthine oxidase inhibition. These dihydroflavonols displayed positive quenching abilities towards O(2)(-) and DPPH free radicals, in which the majority exhibited superior antioxidant properties to Vitamin C. cis-Configurated compound (+/-)-3e demonstrated remarkable inhibition to LPO with an IC(50) value of 1.9+/-0.3 microM, which was apparently stronger than that of quercetin (IC(50)=6.0+/-0.4 microM). trans-Configurated dihydroflavonol (+/-)-4h exhibited significant protective effect on PC12 cells against oxidative damage with an EC(50) value of 41.5+/-5.3 microM, more effective compared to that of quercetin (EC(50)=81.8+/-8.7 microM). The 6-OH-5,7-dimethoxy analogue (+/-)-3d showed significant inhibition of xanthine oxidase with an IC(50) value of 16.0+/-0.8 microM, which is superior to that of allopurinol (IC(50)=23.5+/-2.0 microM). In addition to the hypothesized action mechanism of the bio-active compounds, 3D modeling was used to analyze the relationship between the minimized-energy structures and antioxidant activities.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Gong J,Huang K,Wang F,Yang L,Feng Y,Li H,Li X,Zeng S,Wu X,Stöckigt J,Zhao Y,Qu J

doi

10.1016/j.bmc.2009.03.032

subject

Has Abstract

pub_date

2009-05-01 00:00:00

pages

3414-25

issue

9

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(09)00269-7

journal_volume

17

pub_type

杂志文章

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