Unexpected role of 5-OH in DPPH radical-scavenging activity of 4-thiaflavans. Revealed by theoretical calculations

Lan-Fen Wang; Hong-Yu Zhang

doi:10.1016/j.bmcl.2004.02.066

Unexpected role of 5-OH in DPPH radical-scavenging activity of 4-thiaflavans. Revealed by theoretical calculations

Bioorg Med Chem Lett. 2004 May 17;14(10):2609-11. doi: 10.1016/j.bmcl.2004.02.066.

Authors

Lan-Fen Wang¹, Hong-Yu Zhang

Affiliation

¹ Laboratory for Computational Biology and Shandong Provincial Research Center for Bioinformatic Engineering and Technique, Shandong University of Technology, Zibo 255049, PR China.

PMID: 15109662
DOI: 10.1016/j.bmcl.2004.02.066

Abstract

The O-H bond dissociation enthalpies (BDEs) of 4-thiaflavans were calculated by a combined density functional theory method (RO)B3LYP/6-311 + G(2d,2p)//AM1/AM1. The calculated BDEs not only gave a reasonable explanation on the DPPH radical-scavenging activity difference of 4-thiaflavans, but also revealed the unexpected role of 5-OH in enhancing the antioxidant activity of A-ring.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antioxidants / chemistry
Biphenyl Compounds
Flavonoids / chemistry*
Free Radical Scavengers / chemistry*
Hydroxyl Radical / chemistry*
Models, Theoretical
Picrates / chemistry
Structure-Activity Relationship
Thermodynamics

Substances

Antioxidants
Biphenyl Compounds
Flavonoids
Free Radical Scavengers
Picrates
Hydroxyl Radical
1,1-diphenyl-2-picrylhydrazyl