Stability of flavonoids in the presence of riboflavin-photogenerated reactive oxygen species: a kinetic and mechanistic study on quercetin, morin and rutin. 2010

María P Montaña, and Walter A Massad, and Susana Criado, and Alicia Biasutti, and Norman A García
Area de Química Física-INQUISAL, Universidad Nacional de San Luis, San Luis, Argentina. mpaulina@unsl.edu.ar

Kinetic and mechanistic aspects on the stability of the flavones (FL) quercetin (Que), morin (Mor) and rutin (Rut), in methanolic solution and in the presence of reactive oxygen species (ROS) generated by visible light-promoted riboflavin (Rf, vitamin B(2)) photoirradiation were studied. The system was chosen as a model for the evaluation of the in vivo protective effect of biological targets by the flavones. The overall picture includes the vitamin as an endogenous natural photosensitizer. A systematic study on the effect of ROS on FL photostability shows that under work conditions Que is oxidized by singlet molecular oxygen (O(2)((1)Delta(g))), superoxide radical anion (O(2)(-)) and hydrogen peroxide; Mor is degraded by O(2)((1)Delta(g)) and O(2)(-) whereas Rut only reacts with O(2)((1)Delta(g)). Que and Rut, with an extremely poor overall rate constant, are mainly physical quenchers of O(2)((1)Delta(g)). Mor, with O(2)((1)Delta(g))-interception ability slightly lower than the recognized synthetic antioxidant trolox (Tx), behaves as a typical sacrificial scavenger provided that ca 80% of the collisions with O(2)((1)Delta(g)) cause its own degradation, whereas this parameter reaches around 50% in the case of Tx.

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D008027 Light That portion of the electromagnetic spectrum in the visible, ultraviolet, and infrared range. Light, Visible,Photoradiation,Radiation, Visible,Visible Radiation,Photoradiations,Radiations, Visible,Visible Light,Visible Radiations
D010777 Photochemistry A branch of physical chemistry which studies chemical reactions, isomerization and physical behavior that may occur under the influence of visible and/or ultraviolet light. Photochemistries
D011794 Quercetin A flavonol widely distributed in plants. It is an antioxidant, like many other phenolic heterocyclic compounds. Glycosylated forms include RUTIN and quercetrin. 3,3',4',5,7-Pentahydroxyflavone,Dikvertin
D005419 Flavonoids A group of phenyl benzopyrans named for having structures like FLAVONES. 2-Phenyl-Benzopyran,2-Phenyl-Chromene,Bioflavonoid,Bioflavonoids,Flavonoid,2-Phenyl-Benzopyrans,2-Phenyl-Chromenes,2 Phenyl Benzopyran,2 Phenyl Benzopyrans,2 Phenyl Chromene,2 Phenyl Chromenes
D012256 Riboflavin Nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables. The richest natural source is yeast. It occurs in the free form only in the retina of the eye, in whey, and in urine; its principal forms in tissues and cells are as FLAVIN MONONUCLEOTIDE and FLAVIN-ADENINE DINUCLEOTIDE. Vitamin B 2,Vitamin G,Vitamin B2
D012431 Rutin A flavonol glycoside found in many plants, including BUCKWHEAT; TOBACCO; FORSYTHIA; HYDRANGEA; VIOLA, etc. It has been used therapeutically to decrease capillary fragility. 3-Rhamnosyl-Glucosyl Quercetin,Quercetin-3-Rutinoside,Rutoside,Quercetin 3 Rutinoside,Quercetin, 3-Rhamnosyl-Glucosyl
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D017382 Reactive Oxygen Species Molecules or ions formed by the incomplete one-electron reduction of oxygen. These reactive oxygen intermediates include SINGLET OXYGEN; SUPEROXIDES; PEROXIDES; HYDROXYL RADICAL; and HYPOCHLOROUS ACID. They contribute to the microbicidal activity of PHAGOCYTES, regulation of SIGNAL TRANSDUCTION and GENE EXPRESSION, and the oxidative damage to NUCLEIC ACIDS; PROTEINS; and LIPIDS. Active Oxygen Species,Oxygen Radical,Oxygen Radicals,Pro-Oxidant,Reactive Oxygen Intermediates,Active Oxygen,Oxygen Species, Reactive,Pro-Oxidants,Oxygen, Active,Pro Oxidant,Pro Oxidants,Radical, Oxygen

Related Publications

María P Montaña, and Walter A Massad, and Susana Criado, and Alicia Biasutti, and Norman A García
January 2010, Photochemistry and photobiology,
María P Montaña, and Walter A Massad, and Susana Criado, and Alicia Biasutti, and Norman A García
June 2012, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology,
María P Montaña, and Walter A Massad, and Susana Criado, and Alicia Biasutti, and Norman A García
October 2014, Journal of agricultural and food chemistry,
María P Montaña, and Walter A Massad, and Susana Criado, and Alicia Biasutti, and Norman A García
January 2012, Analytical and bioanalytical chemistry,
María P Montaña, and Walter A Massad, and Susana Criado, and Alicia Biasutti, and Norman A García
January 2013, Photochemistry and photobiology,
María P Montaña, and Walter A Massad, and Susana Criado, and Alicia Biasutti, and Norman A García
August 2005, Journal of photochemistry and photobiology. B, Biology,
María P Montaña, and Walter A Massad, and Susana Criado, and Alicia Biasutti, and Norman A García
January 2000, Photochemistry and photobiology,
María P Montaña, and Walter A Massad, and Susana Criado, and Alicia Biasutti, and Norman A García
January 2013, PloS one,
María P Montaña, and Walter A Massad, and Susana Criado, and Alicia Biasutti, and Norman A García
January 1978, Farmatsiia,
María P Montaña, and Walter A Massad, and Susana Criado, and Alicia Biasutti, and Norman A García
August 2011, International journal of food sciences and nutrition,
Copied contents to your clipboard!