Details of the antioxidant mechanism of hydroxycinnamic acids

https://doi.org/10.17221/611/2014-CJFSCitation:Shang Y.-., Liu B.-., Zhao M.-. (2015): Details of the antioxidant mechanism of hydroxycinnamic acids. Czech J. Food Sci., 33: 210-216.
download PDF
Antioxidant activities and free radical-mediated DNA strand breakages of five hydroxycinnamic acids were examined. Kinetic analysis of a stable galvinoxy (GO•)-scavenging reaction of hydroxycinnamic acids demonstrated that the molecular structure and the reaction medium were two important factors affecting the antioxidant mechanism and activity. In methanol, the kinetic process of the compounds, which have electron-donating groups (-OH, -OCH3) in the ortho- or para-position of 4-OH, was primarily governed by the sequential proton loss electron transfer (SPLET mechanism). While, in ethyl acetate, the reaction mechanism is predominantly direct hydrogen atom transfer (HAT mechanism). But for the compounds having only one hydroxyl, both in ethyl acetate and methanol, the reaction mechanism is only HAT. At the same time, the compound bearing o-diphenoxyl is not the most active one in our tested environment.
References:
Amorati Riccardo, Pedulli Gian Franco, Cabrini Luciana, Zambonin Laura, Landi Laura (2006): Solvent and pH Effects on the Antioxidant Activity of Caffeic and Other Phenolic Acids. Journal of Agricultural and Food Chemistry, 54, 2932-2937  https://doi.org/10.1021/jf053159+
 
Braekke Kristin, Harsem Nina K, Staff Anne C (2006): Oxidative Stress and Antioxidant Status in Fetal Circulation in Preeclampsia. Pediatric Research, 60, 560-564  https://doi.org/10.1203/01.pdr.0000242299.01219.6a
 
Allan Butterfield D. (2002): Amyloid β-peptide (1-42)-induced Oxidative Stress and Neurotoxicity: Implications for Neurodegeneration in Alzheimer's Disease Brain. A Review. Free Radical Research, 36, 1307-1313  https://doi.org/10.1080/1071576021000049890
 
Beltrán J.L., Sanli N., Fonrodona G., Barrón D., Özkan G., Barbosa J. (2003): Spectrophotometric, potentiometric and chromatographic pKa values of polyphenolic acids in water and acetonitrile–water media. Analytica Chimica Acta, 484, 253-264  https://doi.org/10.1016/S0003-2670(03)00334-9
 
Clifford Michael N (1999): Chlorogenic acids and other cinnamates - nature, occurrence and dietary burden. Journal of the Science of Food and Agriculture, 79, 362-372  https://doi.org/10.1002/(SICI)1097-0010(19990301)79:3<362::AID-JSFA256>3.0.CO;2-D
 
ERDEMGIL F, SANLI S, SANLI N, OZKAN G, BARBOSA J, GUITERAS J, BELTRAN J (2007): Determination of pKa values of some hydroxylated benzoic acids in methanol–water binary mixtures by LC methodology and potentiometry. Talanta, 72, 489-496  https://doi.org/10.1016/j.talanta.2006.11.007
 
Foti Mario C., Daquino Carmelo, Geraci Corrada (2004): Electron-Transfer Reaction of Cinnamic Acids and Their Methyl Esters with the DPPH Radical in Alcoholic Solutions. The Journal of Organic Chemistry, 69, 2309-2314  https://doi.org/10.1021/jo035758q
 
Halliwell Barry (2001): Role of Free Radicals in the Neurodegenerative Diseases. Drugs & Aging, 18, 685-716  https://doi.org/10.2165/00002512-200118090-00004
 
Herrmann Karl, Nagel Charles W. (1989): Occurrence and content of hydroxycinnamic and hydroxybenzoic acid compounds in foods. Critical Reviews in Food Science and Nutrition, 28, 315-347  https://doi.org/10.1080/10408398909527504
 
Hracsko Zsuzsanna, Orvos Hajnalka, Novak Zoltan, Pal Attila, Varga Ilona S. (2008): Evaluation of oxidative stress markers in neonates with intra-uterine growth retardation. Redox Report, 13, 11-16  https://doi.org/10.1179/135100008X259097
 
Kong Ling, Sun Zhen-Ling, Wang Lan-Fen, Zhang Hong-Yu, Yao Si-De (2004): Theoretical Elucidation of the Radical-Scavenging-Activity Difference of Hydroxycinnamic Acid Derivatives. Helvetica Chimica Acta, 87, 511-515  https://doi.org/10.1002/hlca.200490048
 
León-Carmona Jorge Rafael, Alvarez-Idaboy Juan Raúl, Galano Annia (2012): On the peroxyl scavenging activity of hydroxycinnamic acid derivatives: mechanisms, kinetics, and importance of the acid–base equilibrium. Physical Chemistry Chemical Physics, 14, 12534-  https://doi.org/10.1039/c2cp40651a
 
Lin Weizhen, Navaratnam Suppiah, Yao Side, Lin Nianyun (1998): Antioxidative properties of hydroxycinnamic acid derivatives and a phenylpropanoid glycoside. A pulse radiolysis study. Radiation Physics and Chemistry, 53, 425-430  https://doi.org/10.1016/S0969-806X(97)00318-6
 
Lithoxoidou Alexandra T., Bakalbassis Evangelos G. (2004): Liquid-phase theoretical antioxidant activity trend of some cinnamic acid antioxidants. Journal of the American Oil Chemists' Society, 81, 799-802  https://doi.org/10.1007/s11746-004-0981-9
 
Litwinienko Grzegorz, Ingold K. U. (2003): Abnormal Solvent Effects on Hydrogen Atom Abstractions. 1. The Reactions of Phenols with 2,2-Diphenyl-1-picrylhydrazyl (dpph ) in Alcohols. The Journal of Organic Chemistry, 68, 3433-3438  https://doi.org/10.1021/jo026917t
 
Litwinienko Grzegorz, Ingold K. U. (2004): Abnormal Solvent Effects on Hydrogen Atom Abstraction. 2. Resolution of the Curcumin Antioxidant Controversy. The Role of Sequential Proton Loss Electron Transfer. The Journal of Organic Chemistry, 69, 5888-5896  https://doi.org/10.1021/jo049254j
 
Litwinienko Grzegorz, Ingold K. U. (2007): Solvent Effects on the Rates and Mechanisms of Reaction of Phenols with Free Radicals. Accounts of Chemical Research, 40, 222-230  https://doi.org/10.1021/ar0682029
 
Mattila Pirjo, Hellström Jarkko (2007): Phenolic acids in potatoes, vegetables, and some of their products. Journal of Food Composition and Analysis, 20, 152-160  https://doi.org/10.1016/j.jfca.2006.05.007
 
Mattila Pirjo, Kumpulainen Jorma (2002): Determination of Free and Total Phenolic Acids in Plant-Derived Foods by HPLC with Diode-Array Detection. Journal of Agricultural and Food Chemistry, 50, 3660-3667  https://doi.org/10.1021/jf020028p
 
Moon Jae-Hak, Terao Junji (1998): Antioxidant Activity of Caffeic Acid and Dihydrocaffeic Acid in Lard and Human Low-Density Lipoprotein . Journal of Agricultural and Food Chemistry, 46, 5062-5065  https://doi.org/10.1021/jf9805799
 
Musialik Malgorzata, Litwinienko Grzegorz (2005): Scavenging of dpph Radicals by Vitamin E Is Accelerated by Its Partial Ionization:  the Role of Sequential Proton Loss Electron Transfer. Organic Letters, 7, 4951-4954  https://doi.org/10.1021/ol051962j
 
Nakanishi Ikuo, Fukuhara Kiyoshi, Shimada Tomokazu, Ohkubo Kei, Iizuka Yuko, Inami Keiko, Mochizuki Masataka, Urano Shiro, Itoh Shinobu, Miyata Naoki, Fukuzumi Shunichi (): Effects of magnesium ion on kinetic stability and spin distribution of phenoxyl radical derived from a vitamin E analogue: mechanistic insight into antioxidative hydrogen-transfer reaction of vitamin EElectronic supplementary information available: calculated spin density distributions and dependence of kHT on [Mg2+] for hydrogen transfer. See http://www.rsc.org/suppdata/p2/b2/b205380b/. Journal of the Chemical Society, Perkin Transactions 2, , 1520-1524  https://doi.org/10.1039/b205380b
 
Pan Jing-Xi, Wang Wen-Feng, Lin Wei-Zhen, Lu Chang-Yuan, Han Zhen-Hui, Yao Si-De, Lin Nian-Yun (1999): Interaction of hydroxycinnamic acid derivatives with the Cl 3 COO radical: A pulse radiolysis study. Free Radical Research, 30, 241-245  https://doi.org/10.1080/10715769900300261
 
Pino Eduardo, Campos Ana M., López-Alarcón Camilo, Aspée Alexis, Lissi Eduardo (2006): Free radical scavenging capacity of hydroxycinnamic acids and related compounds. Journal of Physical Organic Chemistry, 19, 759-764  https://doi.org/10.1002/poc.1071
 
Pulido Raquel, Bravo Laura, Saura-Calixto Fulgencio (2000): Antioxidant Activity of Dietary Polyphenols As Determined by a Modified Ferric Reducing/Antioxidant Power Assay. Journal of Agricultural and Food Chemistry, 48, 3396-3402  https://doi.org/10.1021/jf9913458
 
Qian Yi-Ping, Shang Ya-Jing, Teng Qing-Feng, Chang Jin, Fan Gui-Juan, Wei Xia, Li Ran-Ran, Li Hong-Ping, Yao Xiao-Jun, Dai Fang, Zhou Bo (2011): Hydroxychalcones as potent antioxidants: Structure–activity relationship analysis and mechanism considerations. Food Chemistry, 126, 241-248  https://doi.org/10.1016/j.foodchem.2010.11.011
 
Rahman Arshad, Fazal Fabeha, Greensill Julie, Ainley K., Parish J.H., Hadi S.M. (1992): Strand scission in DNA induced by dietary flavonoids: role of Cu(I) and oxygen free radicals and biological consequences of scission. Molecular and Cellular Biochemistry, 111, -  https://doi.org/10.1007/BF00229567
 
Ray Paresh Chandra, Munichandraiah N., Das Puspendu Kumar (1996): Dissociation constants of some substituted cinnamic acids in protic solvents: measurements by hyper-Rayleigh scattering and potentiometric techniques. Chemical Physics, 211, 499-505  https://doi.org/10.1016/0301-0104(96)00204-2
 
Shang Ya-Jing, Qian Yi-Ping, Liu Xiao-Da, Dai Fang, Shang Xian-Ling, Jia Wen-Qiang, Liu Qiang, Fang Jian-Guo, Zhou Bo (2009): Radical-Scavenging Activity and Mechanism of Resveratrol-Oriented Analogues: Influence of the Solvent, Radical, and Substitution. The Journal of Organic Chemistry, 74, 5025-5031  https://doi.org/10.1021/jo9007095
 
Watanabe Akira, Noguchi Noriko, Fujisawa Akio, Kodama Tatsuhiko, Tamura Kunio, Cynshi Osamu, Niki Etsuo (2000): Stability and Reactivity of Aryloxyl Radicals Derived from a Novel Antioxidant BO-653 and Related Compounds. Effects of Substituent and Side Chain in Solution and Membranes. Journal of the American Chemical Society, 122, 5438-5442  https://doi.org/10.1021/ja9942080
 
van Wenum Ewelina, Jurczakowski Rafal, Litwinienko Grzegorz (2013): Media Effects on the Mechanism of Antioxidant Action of Silybin and 2,3-Dehydrosilybin: Role of the Enol Group. The Journal of Organic Chemistry, 78, 9102-9112  https://doi.org/10.1021/jo401296k
 
Zhu Hongping, Zhao Hongwei, Zhang Zhaoxia, Wang Wenfeng, Yao Side (2006): Laser flash photolysis study on antioxidant properties of hydroxycinnamic acid derivatives. Radiation and Environmental Biophysics, 45, 73-77  https://doi.org/10.1007/s00411-006-0041-8
 
Amorati Riccardo, Pedulli Gian Franco, Cabrini Luciana, Zambonin Laura, Landi Laura (2006): Solvent and pH Effects on the Antioxidant Activity of Caffeic and Other Phenolic Acids. Journal of Agricultural and Food Chemistry, 54, 2932-2937  https://doi.org/10.1021/jf053159+
 
Braekke Kristin, Harsem Nina K, Staff Anne C (2006): Oxidative Stress and Antioxidant Status in Fetal Circulation in Preeclampsia. Pediatric Research, 60, 560-564  https://doi.org/10.1203/01.pdr.0000242299.01219.6a
 
Allan Butterfield D. (2002): Amyloid β-peptide (1-42)-induced Oxidative Stress and Neurotoxicity: Implications for Neurodegeneration in Alzheimer's Disease Brain. A Review. Free Radical Research, 36, 1307-1313  https://doi.org/10.1080/1071576021000049890
 
Beltrán J.L., Sanli N., Fonrodona G., Barrón D., Özkan G., Barbosa J. (2003): Spectrophotometric, potentiometric and chromatographic pKa values of polyphenolic acids in water and acetonitrile–water media. Analytica Chimica Acta, 484, 253-264  https://doi.org/10.1016/S0003-2670(03)00334-9
 
Clifford Michael N (1999): Chlorogenic acids and other cinnamates - nature, occurrence and dietary burden. Journal of the Science of Food and Agriculture, 79, 362-372  https://doi.org/10.1002/(SICI)1097-0010(19990301)79:3<362::AID-JSFA256>3.0.CO;2-D
 
ERDEMGIL F, SANLI S, SANLI N, OZKAN G, BARBOSA J, GUITERAS J, BELTRAN J (2007): Determination of pKa values of some hydroxylated benzoic acids in methanol–water binary mixtures by LC methodology and potentiometry. Talanta, 72, 489-496  https://doi.org/10.1016/j.talanta.2006.11.007
 
Foti Mario C., Daquino Carmelo, Geraci Corrada (2004): Electron-Transfer Reaction of Cinnamic Acids and Their Methyl Esters with the DPPH Radical in Alcoholic Solutions. The Journal of Organic Chemistry, 69, 2309-2314  https://doi.org/10.1021/jo035758q
 
Halliwell Barry (2001): Role of Free Radicals in the Neurodegenerative Diseases. Drugs & Aging, 18, 685-716  https://doi.org/10.2165/00002512-200118090-00004
 
Herrmann Karl, Nagel Charles W. (1989): Occurrence and content of hydroxycinnamic and hydroxybenzoic acid compounds in foods. Critical Reviews in Food Science and Nutrition, 28, 315-347  https://doi.org/10.1080/10408398909527504
 
Hracsko Zsuzsanna, Orvos Hajnalka, Novak Zoltan, Pal Attila, Varga Ilona S. (2008): Evaluation of oxidative stress markers in neonates with intra-uterine growth retardation. Redox Report, 13, 11-16  https://doi.org/10.1179/135100008X259097
 
Kong Ling, Sun Zhen-Ling, Wang Lan-Fen, Zhang Hong-Yu, Yao Si-De (2004): Theoretical Elucidation of the Radical-Scavenging-Activity Difference of Hydroxycinnamic Acid Derivatives. Helvetica Chimica Acta, 87, 511-515  https://doi.org/10.1002/hlca.200490048
 
León-Carmona Jorge Rafael, Alvarez-Idaboy Juan Raúl, Galano Annia (2012): On the peroxyl scavenging activity of hydroxycinnamic acid derivatives: mechanisms, kinetics, and importance of the acid–base equilibrium. Physical Chemistry Chemical Physics, 14, 12534-  https://doi.org/10.1039/c2cp40651a
 
Lin Weizhen, Navaratnam Suppiah, Yao Side, Lin Nianyun (1998): Antioxidative properties of hydroxycinnamic acid derivatives and a phenylpropanoid glycoside. A pulse radiolysis study. Radiation Physics and Chemistry, 53, 425-430  https://doi.org/10.1016/S0969-806X(97)00318-6
 
Lithoxoidou Alexandra T., Bakalbassis Evangelos G. (2004): Liquid-phase theoretical antioxidant activity trend of some cinnamic acid antioxidants. Journal of the American Oil Chemists' Society, 81, 799-802  https://doi.org/10.1007/s11746-004-0981-9
 
Litwinienko Grzegorz, Ingold K. U. (2003): Abnormal Solvent Effects on Hydrogen Atom Abstractions. 1. The Reactions of Phenols with 2,2-Diphenyl-1-picrylhydrazyl (dpph ) in Alcohols. The Journal of Organic Chemistry, 68, 3433-3438  https://doi.org/10.1021/jo026917t
 
Litwinienko Grzegorz, Ingold K. U. (2004): Abnormal Solvent Effects on Hydrogen Atom Abstraction. 2. Resolution of the Curcumin Antioxidant Controversy. The Role of Sequential Proton Loss Electron Transfer. The Journal of Organic Chemistry, 69, 5888-5896  https://doi.org/10.1021/jo049254j
 
Litwinienko Grzegorz, Ingold K. U. (2007): Solvent Effects on the Rates and Mechanisms of Reaction of Phenols with Free Radicals. Accounts of Chemical Research, 40, 222-230  https://doi.org/10.1021/ar0682029
 
Mattila Pirjo, Hellström Jarkko (2007): Phenolic acids in potatoes, vegetables, and some of their products. Journal of Food Composition and Analysis, 20, 152-160  https://doi.org/10.1016/j.jfca.2006.05.007
 
Mattila Pirjo, Kumpulainen Jorma (2002): Determination of Free and Total Phenolic Acids in Plant-Derived Foods by HPLC with Diode-Array Detection. Journal of Agricultural and Food Chemistry, 50, 3660-3667  https://doi.org/10.1021/jf020028p
 
Moon Jae-Hak, Terao Junji (1998): Antioxidant Activity of Caffeic Acid and Dihydrocaffeic Acid in Lard and Human Low-Density Lipoprotein . Journal of Agricultural and Food Chemistry, 46, 5062-5065  https://doi.org/10.1021/jf9805799
 
Musialik Malgorzata, Litwinienko Grzegorz (2005): Scavenging of dpph Radicals by Vitamin E Is Accelerated by Its Partial Ionization:  the Role of Sequential Proton Loss Electron Transfer. Organic Letters, 7, 4951-4954  https://doi.org/10.1021/ol051962j
 
Nakanishi Ikuo, Fukuhara Kiyoshi, Shimada Tomokazu, Ohkubo Kei, Iizuka Yuko, Inami Keiko, Mochizuki Masataka, Urano Shiro, Itoh Shinobu, Miyata Naoki, Fukuzumi Shunichi (): Effects of magnesium ion on kinetic stability and spin distribution of phenoxyl radical derived from a vitamin E analogue: mechanistic insight into antioxidative hydrogen-transfer reaction of vitamin EElectronic supplementary information available: calculated spin density distributions and dependence of kHT on [Mg2+] for hydrogen transfer. See http://www.rsc.org/suppdata/p2/b2/b205380b/. Journal of the Chemical Society, Perkin Transactions 2, , 1520-1524  https://doi.org/10.1039/b205380b
 
Pan Jing-Xi, Wang Wen-Feng, Lin Wei-Zhen, Lu Chang-Yuan, Han Zhen-Hui, Yao Si-De, Lin Nian-Yun (1999): Interaction of hydroxycinnamic acid derivatives with the Cl 3 COO radical: A pulse radiolysis study. Free Radical Research, 30, 241-245  https://doi.org/10.1080/10715769900300261
 
Pino Eduardo, Campos Ana M., López-Alarcón Camilo, Aspée Alexis, Lissi Eduardo (2006): Free radical scavenging capacity of hydroxycinnamic acids and related compounds. Journal of Physical Organic Chemistry, 19, 759-764  https://doi.org/10.1002/poc.1071
 
Pulido Raquel, Bravo Laura, Saura-Calixto Fulgencio (2000): Antioxidant Activity of Dietary Polyphenols As Determined by a Modified Ferric Reducing/Antioxidant Power Assay. Journal of Agricultural and Food Chemistry, 48, 3396-3402  https://doi.org/10.1021/jf9913458
 
Qian Yi-Ping, Shang Ya-Jing, Teng Qing-Feng, Chang Jin, Fan Gui-Juan, Wei Xia, Li Ran-Ran, Li Hong-Ping, Yao Xiao-Jun, Dai Fang, Zhou Bo (2011): Hydroxychalcones as potent antioxidants: Structure–activity relationship analysis and mechanism considerations. Food Chemistry, 126, 241-248  https://doi.org/10.1016/j.foodchem.2010.11.011
 
Rahman Arshad, Fazal Fabeha, Greensill Julie, Ainley K., Parish J.H., Hadi S.M. (1992): Strand scission in DNA induced by dietary flavonoids: role of Cu(I) and oxygen free radicals and biological consequences of scission. Molecular and Cellular Biochemistry, 111, -  https://doi.org/10.1007/BF00229567
 
Ray Paresh Chandra, Munichandraiah N., Das Puspendu Kumar (1996): Dissociation constants of some substituted cinnamic acids in protic solvents: measurements by hyper-Rayleigh scattering and potentiometric techniques. Chemical Physics, 211, 499-505  https://doi.org/10.1016/0301-0104(96)00204-2
 
Shang Ya-Jing, Qian Yi-Ping, Liu Xiao-Da, Dai Fang, Shang Xian-Ling, Jia Wen-Qiang, Liu Qiang, Fang Jian-Guo, Zhou Bo (2009): Radical-Scavenging Activity and Mechanism of Resveratrol-Oriented Analogues: Influence of the Solvent, Radical, and Substitution. The Journal of Organic Chemistry, 74, 5025-5031  https://doi.org/10.1021/jo9007095
 
Watanabe Akira, Noguchi Noriko, Fujisawa Akio, Kodama Tatsuhiko, Tamura Kunio, Cynshi Osamu, Niki Etsuo (2000): Stability and Reactivity of Aryloxyl Radicals Derived from a Novel Antioxidant BO-653 and Related Compounds. Effects of Substituent and Side Chain in Solution and Membranes. Journal of the American Chemical Society, 122, 5438-5442  https://doi.org/10.1021/ja9942080
 
van Wenum Ewelina, Jurczakowski Rafal, Litwinienko Grzegorz (2013): Media Effects on the Mechanism of Antioxidant Action of Silybin and 2,3-Dehydrosilybin: Role of the Enol Group. The Journal of Organic Chemistry, 78, 9102-9112  https://doi.org/10.1021/jo401296k
 
Zhu Hongping, Zhao Hongwei, Zhang Zhaoxia, Wang Wenfeng, Yao Side (2006): Laser flash photolysis study on antioxidant properties of hydroxycinnamic acid derivatives. Radiation and Environmental Biophysics, 45, 73-77  https://doi.org/10.1007/s00411-006-0041-8
 
download PDF

© 2020 Czech Academy of Agricultural Sciences | Prohlášení o přístupnosti