Selected anthraquinones as potential free radical scavengers and P-glycoprotein inhibitors

Organic & Biomolecular Chemistry
Svetlana JeremićZoran Marković

Abstract

Disruption of homeostasis can increase the amount of free radicals formed during metabolic processes. This phenomenon known as oxidative stress can have numerous negative outcomes. The role of dietary antioxidants is to help the prevention of oxidative stress. We investigated free radical scavenging capacity of six structurally similar anthraquinones (alizarin, purpurin, chrysophanol, emodin, aloe-emodin and 1,3,8-trihydroxyanthraquinone) for inactivating a set of ten hydroxy and peroxy free radicals. The antioxidant capacity of anthraquinones was estimated by considering Gibbs free energy of three studied reaction mechanisms: hydrogen atom transfer (HAT), single-electron transfer followed by proton transfer (SET-PT) and sequential proton loss electron transfer (SPLET). The geometry of all participants in chemical reactions was optimized using the M06-2X/6-311++G(d,p) level of theory. Benzene, pentyl ethanoate, dimethyl sulfoxide and water were used to investigate the impact of solvent polarity on the thermodynamic feasibility of antiradical reactions. It was found that HAT and SPLET mechanisms are operative and competitive, while the SET-PT mechanism is not thermodynamically plausible. Among the studied anthraquinones, AL and ...Continue Reading

References

Jan 1, 1992·Critical Reviews in Food Science and Nutrition·F Shahidi, P K Wanasundara
Feb 1, 1969·The Journal of Histochemistry and Cytochemistry : Official Journal of the Histochemistry Society·H PuchtlerM S Terry
Feb 1, 1996·Journal of Molecular Graphics·W HumphreyK Schulten
Jun 1, 1996·European Journal of Cancer : Official Journal for European Organization for Research and Treatment of Cancer (EORTC) [and] European Association for Cancer Research (EACR)·U A Germann
Oct 4, 2002·Nutrition·Yun-Zhong FangGuoyao Wu
Apr 20, 2004·CNS Drugs·Lesley J Scott, David P Figgitt
Jul 29, 2004·Chemical Society Reviews·Ester S B FerreiraAnita Quye
Nov 5, 2004·The Journal of Biological Chemistry·Marcus PickhardtEckhard Mandelkow
Jul 20, 2005·Journal of Clinical Pharmacology·Vera S Donnenberg, Albert D Donnenberg
Sep 19, 2006·The International Journal of Biochemistry & Cell Biology·Marian ValkoJoshua Telser
Mar 11, 2008·Cardiovascular Pathology : the Official Journal of the Society for Cardiovascular Pathology·Gregory A FishbeinMichael C Fishbein
Nov 27, 2008·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Kaoru InoueAkiyoshi Nishikawa
Jan 23, 2009·BMC Structural Biology·Jean-Paul BeckerMartine Prévost
Mar 17, 2009·Biochimica Et Biophysica Acta·King Leung Fung, Michael M Gottesman
Apr 29, 2009·Journal of Computational Chemistry·Garrett M MorrisArthur J Olson
Oct 27, 2009·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Prabhjit KaurSatwinderjeet Kaur
Oct 16, 2010·Journal of the Science of Food and Agriculture·Fátima Paiva-MartinsMaria P M Marques
Jan 14, 2011·Journal of Molecular Modeling·Zoran S MarkovićNenad Filipović
Jul 7, 2011·PLoS Computational Biology·Elena DolghihMatthew P Jacobson
Nov 29, 2011·Drug Discovery Today·Lei ChenTingjun Hou
Jul 1, 2010·Pharmacognosy Reviews·V LoboN Chandra
Mar 14, 2012·Journal of Orthopaedic Research : Official Publication of the Orthopaedic Research Society·Caterina FotiaNicola Baldini
Aug 17, 2012·Organic & Biomolecular Chemistry·José M RiveraJean C Rivera-Ríos
Jan 24, 2013·Journal of Clinical Biochemistry and Nutrition·Yasukazu YoshidaMototada Shichiri
Feb 28, 2013·Food Chemistry·Zoran MarkovićDragan Amić
May 24, 2013·Physical Chemistry Chemical Physics : PCCP·Jozef LengyelErik Klein
Jun 28, 2013·Journal of Chemical Information and Modeling·Ricardo J FerreiraDaniel J V A dos Santos
Jun 27, 2014·Journal of Molecular Modeling·Jelena ĐorovićZoran Marković

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Citations

Jun 15, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Guglielmina FroldiMargherita Grison
Dec 13, 2019·BMC Complementary and Alternative Medicine·Woo NamMendel Friedman
Aug 3, 2019·The Journal of Pharmacy and Pharmacology·Long XieXiaofang Li
Jan 9, 2021·Journal of Cellular Biochemistry·Wojciech TrybusGrzegorz Król

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Methods Mentioned

BETA
SPLET

Software Mentioned

SET
BIOVIA Discovery Studio
Gaussian
SPLET
AutoDockTools
VMD
AutoDock

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