A quantum chemical explanation of the antioxidant activity of flavonoids

Chemical Research in Toxicology
S A van AckerA Bast

Abstract

Flavonoids are a group of naturally occurring antioxidants, which over the past years have gained tremendous interest because of their possible therapeutic applicability. The mechanism of their antioxidant activity has been extensively studied over several decades. However, there is still much confusion about the molecular mechanism of radical scavenging and the relationship between structure and activity. Therefore, we have calculated the heat of formation and the geometry of both the parent compound and the corresponding radical using the ab initio program GAMESS. We have compared their differences in energy in order to gain insight into the stability of the radical and the ease with which it is formed. We have also investigated the spin density of the radical, to determine the delocalization possibilities. These calculated data were compared with experimental data from ESR (hyperfine coupling constants) and electrochemical oxidation (Ep/2) and were found to be in good agreement. By comparing the geometries of several flavonoids, we were able to explain the structural dependency of the antioxidant action of these compounds. The extremely good antioxidant activity of the flavonols could be explained by the formation of an intr...Continue Reading

References

Jan 1, 1991·Free Radical Biology & Medicine·G SichelR P Bonomo
Apr 1, 1986·Journal of Computational Chemistry·Scott J WeinerDavid A Case

❮ Previous
Next ❯

Citations

Oct 17, 2013·The International Journal of Biochemistry & Cell Biology·Divyashree RavishankarHelen M I Osborn
May 18, 2004·Journal of the American Society for Mass Spectrometry·Hugo F P MartinsM Natália D S Cordeiro
Jul 16, 2003·European Journal of Pharmacology·M Francisca Molina-JimenezJuana Benedi
Nov 28, 2002·Pharmacology & Therapeutics·Bent H Havsteen
Jan 23, 1999·Free Radical Biology & Medicine·E J LienR Wang
Jan 29, 2003·The Journal of Nutritional Biochemistry·Kelly E. HeimDennis J. Bobilya
Sep 1, 2001·Environmental Toxicology and Pharmacology·C G HeijnenA Bast
Oct 25, 2008·Critical Reviews in Food Science and Nutrition·Gregory Tucker, Kevin Robards
Feb 3, 1998·Critical Reviews in Food Science and Nutrition·D A BalentineL C Bouwens
Feb 3, 1998·Critical Reviews in Food Science and Nutrition·S A WisemanB Frei
Jun 21, 2002·Annals of the New York Academy of Sciences·Wolf Bors, Christa Michel
Feb 24, 2001·Drug Metabolism and Drug Interactions·G GalatiP J O'Brien
Apr 14, 2010·International Journal of Molecular Sciences·Heidi Halbwirth
Jun 19, 2010·International Journal of Molecular Sciences·Santiago Aparicio
Oct 25, 2002·Redox Report : Communications in Free Radical Research·L RackovaM Majekova
Apr 17, 2001·Biochemical and Biophysical Research Communications·A Sekher PannalaC A Rice-Evans
Aug 24, 2011·Evidence-based Complementary and Alternative Medicine : ECAM·Rashmi C VinayakAnil Chatterji
May 6, 2014·Molecular Diversity·Chang Ling ZhaoKang Ru Miao
Apr 8, 2006·Journal of Molecular Modeling·Karen C WeberAlbérico B F da Silva
Jul 27, 2007·Cardiovascular Toxicology·Aalt BastWim J F Van der Vijgh
Apr 25, 2012·Journal of Molecular Modeling·Anna P S MendesAlbérico B F da Silva
Jun 2, 2012·TheScientificWorldJournal·Edyta Kostrzewa-Susłow, Tomasz Janeczko
Nov 16, 2001·Analytical Sciences : the International Journal of the Japan Society for Analytical Chemistry·B YangF Kusu
Jan 27, 2009·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Milan NagyJuraj Krajcovic
May 18, 2011·European Journal of Pharmaceutics and Biopharmaceutics : Official Journal of Arbeitsgemeinschaft Für Pharmazeutische Verfahrenstechnik E.V·Ivana BrzonovaGeorg M Guebitz
Jun 9, 2015·Journal of Nutritional Science and Vitaminology·Chieko ShiotaTakeshi Nikawa

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.