Food Antioxidants: Chemical Insights at the Molecular Level

Annual Review of Food Science and Technology

Volumn 7, Issue , 2016, Pages 335-352

  Galano, Annia ^a   Mazzone, Gloria ^b   Alvarez Diduk, Ruslán ^a   Marino, Tiziana ^b   Alvarez Idaboy, J Raúl ^c   Russo, Nino ^b  

^a DEPARTAMENTO DE QUÍMICA   (Mexico)

^b UNIVERSITY OF CALABRIA   (Italy)

^c UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

Antioxidant properties; Density functional theory; Radical reactions; Reaction mechanisms; Scavenging ability

Indexed keywords

ANTIOXIDANTS; ATOMS; CHEMICAL BONDS; CHEMICAL COMPOUNDS; ELECTRON TRANSITIONS; ELECTRONS; FREE RADICAL REACTIONS; FREE RADICALS; IONIZATION POTENTIAL; REACTION KINETICS; RELIABILITY THEORY;

ADIABATIC IONIZATION POTENTIAL; ANTIOXIDANT PROPERTIES; BOND DISSOCIATION ENERGIES; ELECTRON-PROTON TRANSFERS; PROTON COUPLED ELECTRON TRANSFERS; RADICAL REACTIONS; REACTION MECHANISM; SCAVENGING ABILITY;

DENSITY FUNCTIONAL THEORY;

ANTIOXIDANT; CHELATING AGENT; FREE RADICAL; PROTON; SCAVENGER;

BIOCHEMISTRY; CHEMISTRY; CLASSIFICATION; ELECTRON TRANSPORT; FOOD; FOOD ANALYSIS; HUMAN; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; THERMODYNAMICS;

ANTIOXIDANTS; BIOCHEMICAL PROCESSES; CHELATING AGENTS; ELECTRON TRANSPORT; FOOD; FOOD ANALYSIS; FREE RADICAL SCAVENGERS; FREE RADICALS; HUMANS; OXIDATION-REDUCTION; OXIDATIVE STRESS; PROTONS; THERMODYNAMICS;

EID: 84959927105     PISSN: 19411413     EISSN: 19411421     Source Type: Journal    
DOI: 10.1146/annurev-food-041715-033206     Document Type: Review

References (106)

1. Alberto ME, Russo N, Grand A, Galano A. 2013. A physicochemical examination of the free radical scavenging activity of Trolox: mechanism, kinetics and influence of the environment. Phys. Chem. Chem. Phys. 15(13):4642-50
2. Amíc A, Markovíc Z, Dimitríc Markovíc JM, Stepaníc V, Lucíc B, Amíc D. 2014. Towards an improved prediction of the free radical scavenging potency of flavonoids: the significance of double PCETmechanisms. Food Chem. 152:578-85
3. Angel LA, Ervin KM. 2004. Competitive threshold collision-induced dissociation: gas-phase acidity and O-H bond dissociation enthalpy of phenol. J. Phys. Chem. A 108:8346-52
4. Barzegar A. 2012. The role of electron-transfer and H-atom donation on the superb antioxidant activity and free radical reaction of curcumin. Food Chem. 135(3):1369-76
5. Caicedo C, Iuga C, Castañeda-Arriaga R, Alvarez-Idaboy JR. 2014. Antioxidant activity of selected natural polyphenolic compounds from soybean via peroxyl radical scavenging. RSC Adv. 4(73):38918-30
6. Cao L, Yu H, Shao S, Wang S, Guo Y. 2014. Evaluating the antioxidant capacity of polyphenols with an off-on fluorescence probe and the mechanism study. Anal. Methods 6(18):7149-53
7. Castañeda-Arriaga R, Alvarez-Idaboy JR. 2014. Lipoic acid and dihydrolipoic acid. A comprehensive theoretical study of their antioxidant activity supported by available experimental kinetic data. J. Chem. Inf. Model. 54(6):1642-52
8. Chaiyasit W, Elias RJ, McClements DJ, Decker EA. 2007. Role of physical structures in bulk oils on lipid oxidation. Crit. Rev. Food Sci. Nutr. 47(3):299-317
9. Chatgilialoglu C, D'Angelantonio M, Guerra M, Kaloudis P, Mulazzani QG. 2009. A reevaluation of the ambident reactivity of the guanine moiety towards hydroxyl radicals. Angew. Chem. Int. Ed. 48(12):2214-17
10. Cordova-GomezM, Galano A, Alvarez-Idaboy JR. 2013. Piceatannol, a better peroxyl radical scavenger than resveratrol. RSC Adv. 3(43):20209-18
11. Chiodo SG, Leopoldini M, Russo N, ToscanoM. 2010. The inactivation of lipid peroxide radical by quercetin. A theoretical insight. Phys. Chem. Chem. Phys. 12:7662-70
12. Danta CC, Piplani P. 2014. The discovery and development of new potential antioxidant agents for the treatment of neurodegenerative diseases. Expert Opin. Drug Discov. 9(10):1205-22
13. Dhiman SB, Kamat JP, Naik DB. 2009. Antioxidant activity and free radical scavenging reactions of hydroxybenzyl alcohols. Biochemical and pulse radiolysis studies. Chem. Biol. Interact. 182(2-3):119-27
14. Di Meo F, Lemaur V, Cornil J, Lazzaroni R, Duroux JL, Olivier Y, Trouillas P. 2013. Free radical scavenging by natural polyphenols: atom versus electron transfer. J. Phys. Chem. A 117(10):2082-92
15. DimitrícMarkovíc JM, Milenkovíc D, Amíc D, MojovícM, Pasti I, Markovíc ZS. 2014. The preferred radical scavenging mechanisms of fisetin and baicalein towards oxygen-centred radicals in polar protic and polar aprotic solvents. RSC Adv. 4(61):32228-36
16. DimitrícMarkovíc JM, MilenkovícD, AmícD, Popovíc-BijelícA, MojovícM, et al. 2014. Energy requirements of the reactions of kaempferol and selected radical species in different media: towards the prediction of the possible radical scavenging mechanisms. Struct. Chem. 25:1795-804
17. Dorovíc J, Dimitríc Markovíc JM, Stepaníc V, Begovíc N, Amíc D, Markovíc Z. 2014. Influence of different free radicals on scavenging potency of gallic acid. J. Mol. Model. 20(7):2345
18. Douki T, Cadet J. 1996. Peroxynitrite mediated oxidation of purine bases of nucleosides and isolated DNA. Free Radic. Res. 24(5):369-80
19. Estévez L, Otero N, Mosquera RA. 2010. A computational study on the acidity dependence of radicalscavenging mechanisms of anthocyanidins. J. Phys. Chem. B 114(29):9706-12
20. Everett SA, Kundu SC, Maddix S, Willson RL. 1995. Mechanisms of free-radical scavenging by the nutritional antioxidant carotene. Biochem. Soc. Trans. 23(2):230S
21. Farmanzadeh D, Najafi M. 2013. On the antioxidant activity of the tryptophan derivatives. Bull. Chem. Soc. Jpn. 86(9):1041-50
22. Fifen JJ, NsangouM, Dhaouadi Z, Motapon O, Jaidane N. 2011. Solvent effects on the antioxidant activity of 3, 4-dihydroxyphenylpyruvic acid: DFT and TD-DFT studies. Comput. Theor. Chem. 966(1-3):232-43
23. Focsan AL, Pan S, Kispert LD. 2014. Electrochemical study of astaxanthin and astaxanthin n-octanoic monoester and diester: tendency to form radicals. J. Phys. Chem. B 118(9):2331-39
24. Galano A. 2011. On the direct scavenging activity of melatonin towards hydroxyl and a series of peroxyl radicals. Phys. Chem. Chem. Phys. 13(15):7178-88
25. Galano A, Alvarez-Idaboy JR. 2011. Glutathione: mechanism and kinetics of its non-enzymatic defense action against free radicals. RSC Adv. 1(9):1763-71
26. Galano A, Alvarez-Idaboy JR. 2013. A computationalmethodology for accurate predictions of rate constants in solution: application to the assessment of primary antioxidant activity. J. Comput. Chem. 34(28):2430-45
27. Galano A, Alvarez-Idaboy JR, Francisco-Márquez M. 2011a. Physicochemical insights on the free radical scavenging activity of sesamol: importance of the acid/base equilibrium. J. Phys. Chem. B 115(44):13101-9
28. Galano A, Francisco-Márquez M, Alvarez-Idaboy JR. 2011b. Mechanism and kinetics studies on the antioxidant activity of sinapinic acid. Phys. Chem. Chem. Phys. 13(23):11199-205
29. Galano A, Francisco Marquez M, Pérez-González A. 2014a. Ellagic acid: an unusually versatile protector against oxidative stress. Chem. Res. Toxicol. 27(5):904-18
30. Galano A, León-Carmona JR, Alvarez-Idaboy JR. 2012. Influence of the environment on the protective effects of guaiacol derivatives against oxidative stress: mechanisms, kinetics, and relative antioxidant activity. J. Phys. Chem. B 116(24):7129-37
31. Galano A, Martínez A. 2012. Capsaicin, a tasty free radical scavenger: mechanism of action and kinetics. J. Phys. Chem. B 116(3):1200-8
32. Galano A, Medina ME, Tan DX, Reiter RJ. 2014b. Melatonin and its metabolites as copper chelating agents and their role in inhibiting oxidative stress: a physicochemical analysis. J. Pineal Res. 58(1):107-16
33. Galano A, Pérez-González A. 2012. On the free radical scavenging mechanism of protocatechuic acid, regeneration of the catechol group in aqueous solution. Theor. Chem. Acc. 131(9):1-13
34. Galano A, Vargas R, Martínez A. 2010. Carotenoids can act as antioxidants by oxidizing the superoxide radical anion. Phys. Chem. Chem. Phys. 12(1):193-200
35. Hanthorn JJ, Amorati R, Valgimigli L, Pratt DA. 2012. The reactivity of air-stable pyridine-and pyrimidinecontaining diarylamine antioxidants. J. Org. Chem. 77(16):6895-907
36. Hill TJ, Land EJ, McGarvey DJ, SchalchW, Tinkler JH, Truscott TG. 1995. Interactions between carotenoids and the CCl3O2 radical. J. Am. Chem. Soc. 117(32):8322-26
37. Iuga C, Alvarez-Idaboy JR, Russo N. 2012. Antioxidant activity of trans-resveratrol toward hydroxyl and hydroperoxyl radicals: a quantum chemical and computational kinetics study. J. Org. Chem. 77(8):3868-77
38. Joshi R, Gangabhagirathi R, Venu S, Adhikari S, Mukherjee T. 2012. Antioxidant activity and free radical scavenging reactions of gentisic acid: in-vitro and pulse radiolysis studies. Free Radic. Res. 46(1):11-20
39. Koppal T, Drake J, Yatin S, Jordan B, Varadarajan S, et al. 1999. Peroxynitrite-induced alterations in synaptosomalmembrane proteins: insight into oxidative stress in Alzheimer's disease. J. Neurochem. 72(1):310-17
40. Lengyel J, Rimarcík J, Vagánek A, Klein E. 2013. On the radical scavenging activity of isoflavones: thermodynamics of O-H bond cleavage. Phys. Chem. Chem. Phys. 15(26):10895-903
41. León-Carmona JR, Alvarez-Idaboy JR, GalanoA. 2012. Onthe peroxyl scavenging activity of hydroxycinnamic acid derivatives: mechanisms, kinetics, and importance of the acid-base equilibrium. Phys. Chem. Chem. Phys. 14(36):12534-43
42. León-Carmona JR, Galano A. 2011. Is caffeine a good scavenger of oxygenated free radicals? J. Phys. Chem. B 115(15):4538-46
43. Leopoldini M, Chiodo SG, Russo N, ToscanoM. 2011a. Detailed investigation of the OH radical quenching by natural antioxidant caffeic acid studied by quantum mechanical models. J. Chem. Theory Comput. 7:4218-33
44. Leopoldini M, Marino T, Russo N, Toscano M. 2004a. Antioxidant properties of phenolic compounds: Hatom versus electron transfer mechanism. J. Phys. Chem. A 108:4916-22
45. Leopoldini M, Prieto Pitarch I, Russo N, Toscano M. 2004b. Structure, conformation, and electronic properties of apigenin, luteolin, and taxifolin antioxidants. A first principle theoretical study. J. Phys. Chem. A 108:92-96
46. Leopoldini M, Rondinelli F, Russo N, Toscano M. 2010. Pyranoanthocyanins: a theoretical investigation on their antioxidant activity. J. Agric. Food Chem. 58:8862-71
47. Leopoldini M, Russo N, Chiodo SG, ToscanoM. 2006. Iron chelation by the powerful antioxidant flavonoid quercetin. J. Agric. Food Chem. 54:6343-51
48. Leopoldini M, Russo N, ToscanoM. 2007. A comparative study of the antioxidant power of flavonoid catechin and its planar analogue. J. Agric. Food Chem. 55:7944-49
49. Leopoldini M, Russo N, Toscano M. 2011b. The molecular basis of working mechanism of natural polyphenolic antioxidants. Food Chem. 125:288-306
50. Li M, Liu W, Peng C, Ren Q, Lu W, Deng W. 2013. A DFT study on reaction of eupatilin with hydroxyl radical in solution. Int. J. Quantum Chem. 113(7):966-74
51. Liebler DC, McClure TD. 1996. Antioxidant reactions of carotene: identification of carotenoid-radical adducts. Chem. Res. Toxicol. 9(1):8-11
52. Lipert RJ, Colson SD. 1990. Accurate ionization potentials of phenol and phenol-(H2O) from the electric field dependence of the pump-probe photoionization threshold. J. Chem. Phys. 92:3240-41
53. Litwinienko G, Ingold KU. 2003. Abnormal solvent effects on hydrogen atom abstractions. 1. The reactions of phenols with 2, 2-diphenyl-1-picrylhydrazyl (dpph) in alcohols. J. Org. Chem. 68(9):3433-38
54. Litwinienko G, Ingold KU. 2004. Abnormal solvent effects on hydrogen atom abstraction. 2. Resolution of the curcumin antioxidant controversy. The role of sequential proton loss electron transfer. J. Org. Chem. 69(18):5888-96
55. LucariniM, Pedulli GF. 2010. Free radical intermediates in the inhibition of the autoxidation reaction. Chem. Soc. Rev. 39:2106-19
56. Marino T, Galano A, Russo N. 2014. Radical scavenging ability of gallic acid toward OH and OOH radicals. Reactionmechanism and rate constants from the density functional theory. J. Phys. Chem. B118(35):10380-89
57. Markovíc Z, Amíc D, Milenkovíc D, Dimitríc-Markovíc JM, Markovíc S. 2013a. Examination of the chemical behavior of the quercetin radical cation towards some bases. Phys. Chem. Chem. Phys. 15(19):7370-78
58. MarkovícZ, CrossedD, Signorovíc J, DekícM, RadulovícM, et al. 2013b. DFTstudy of free radical scavenging activity of erodiol. Chem. Pap. 67(11):1453-61
59. Markovíc ZS, Markovíc S, Dimitríc Markovíc JM, Milenkovíc D. 2012a. Structure and reactivity of baicalein radical cation. Int. J. Quantum Chem. 112(8):2009-17
60. Markovíc Z, Milenkovíc D, Orovíc J, DimitrícMarkovíc JM, Stepaníc V, et al. 2012b. Free radical scavenging activity of morin 2--O-phenoxide anion. Food Chem. 135(3):2070-77
61. Marrazzo G, Barbagallo I, Galvano F, MalaguarneraM, Gazzolo D, et al. 2014. Role of dietary and endogenous antioxidants in diabetes. Crit. Rev. Food Sci. Nutr. 54(12):1599-616
62. Martínez A, Galano A, Vargas R. 2011. Free radical scavenger properties of mangostin: thermodynamics and kinetics of HAT and RAF mechanisms. J. Phys. Chem. B 115(43):12591-98
63. Martínez A, Hernández-Marin E, Galano A. 2012. Xanthones as antioxidants: a theoretical study on the thermodynamics and kinetics of the single electron transfer mechanism. Food Funct. 3(4):442-50
64. Mayer JM, Hrovat DA, Thomas JL, Borden WT. 2002. Proton-coupled electron transfer versus hydrogen atom transfer in benzyl/toluene, methoxyl/methanol, and phenoxyl/phenol self-exchange reactions. J. Am. Chem. Soc. 124(37):11142-47
65. Mazzone G, Malaj N, Galano A, Russo N, Toscano M. 2015. Antioxidant properties of several coumarinchalcone hybrids from theoretical insights. RSC Adv. 5:565-75
66. Mazzone G, Malaj N, Russo N, Toscano M. 2013a. Density functional study of the antioxidant activity of some recently synthesized resveratrol analogues. Food Chem. 141:2017-24
67. Mazzone G, Toscano M, Russo N. 2013b. Density functional predictions of antioxidant activity and UV spectral features of nasutin A, isonasutin, ellagic acid, and one of its possible derivatives. J. Agric. Food Chem. 61:9650-57
68. Medina ME, Galano A, Alvarez-Idaboy JR. 2014a. Theoretical study on the peroxyl radicals scavenging activity of esculetin and its regeneration in aqueous solution. Phys. Chem. Chem. Phys. 16(3):1197-207
69. Medina ME, Iuga C, Alvarez-Idaboy JR. 2013. Antioxidant activity of propyl gallate in aqueous and lipid media: a theoretical study. Phys. Chem. Chem. Phys. 15(31):13137-46
70. MedinaME, IugaC, Álvarez-Idaboy JR. 2014b. Antioxidant activity of fraxetin and its regeneration in aqueous media. A density functional theory study. RSC Adv. 4(95):52920-32
71. Mendoza-Wilson AM, Castro-Arredondo SI, Balandrán-Quintana RR. 2014. Computational study of the structure-free radical scavenging relationship of procyanidins. Food Chem. 161:155-61
72. Mikulski D, Eder K, Molski M. 2014. Quantum-chemical study on relationship between structure and antioxidant properties of hepatoprotective compounds occurring in Cynara scolymus and Silybum marianum. J. Theor. Comput. Chem. 13(1):1450004
73. Mortensen A, Skibsted LH, Sampson J, Rice-Evans C, Everett SA. 1997. Comparative mechanisms and rates of free radical scavenging by carotenoid antioxidants. FEBS Lett. 418(1-2):91-97
74. Musialik M, Kuzmicz R, Pawlowski TS, Litwinienko G. 2009. Acidity of hydroxyl groups: an overlooked influence on antiradical properties of flavonoids. J. Org. Chem. 74(7):2699-709
75. Musialik M, Litwinienko G. 2005. Scavenging of DPPH radicals by vitamin E is accelerated by its partial ionization: the role of sequential proton loss electron transfer. Org. Lett. 7(22):4951-54
76. Nakanishi I, Kawashima T, Ohkubo K, Kanazawa H, Inami K, et al. 2005. Electron-transfer mechanism in radical-scavenging reactions by a vitamin E model in a protic medium. Org. Biomol. Chem. 3(4):626-29
77. Nakanishi I, Ohkubo K, Miyazaki K, HakamataW, Urano S, et al. 2004. A planar catechin analogue having a more negative oxidation potential than (+)-catechin as an electron transfer antioxidant against a peroxyl radical. Chem. Res. Toxicol. 17(1):26-31
78. Nakanishi I, Shimada T, Ohkubo K, Manda S, Shimizu T, et al. 2007. Involvement of electron transfer in the radical-scavenging reaction of resveratrol. Chem. Lett. 36(10):1276-77
79. Nakayama T, Uno B. 2010. Quinone-hydroquinone conjugated redox reaction involving proton-coupled electron transfer plays an important role in scavenging superoxide by polyphenolic antioxidants. Chem. Lett. 39(3):162-64
80. Neta P, Huie RE, Mosseri S, Shastri LV, Mittal JP, et al. 1989. Rate constants for reduction of substitutedmethylperoxyl radicals by ascorbate ions and N, N, N-, N-,-tetramethyl-p-phenylenediamine. J. Phys. Chem. 93(10):4099-104
81. Ouchi A, Nagaoka SI, Abe K, Mukai K. 2009. Kinetic study of the aroxyl radical-scavenging reaction of tocopherol in methanol solution: notable effect of the alkali and alkaline earth metal salts on the reaction rates. J. Phys. Chem. B 113(40):13322-31
82. Panchal RG, Reid SP, Tran JP, Bergeron AA, Wells J, et al. 2012. Identification of an antioxidant smallmolecule with broad-spectrum antiviral activity. Antivir. Res. 93(1):23-29
83. Parhiz H, Roohbakhsh A, Soltani F, Rezaee R, Iranshahi M. 2015. Antioxidant and anti-inflammatory properties of the citrus flavonoids hesperidin and hesperetin: an updated review of their molecular mechanisms and experimental models. Phytother. Res. 29(3):323-31
84. Pérez-González A, Galano A. 2012. On the outstanding antioxidant capacity of edaravone derivatives through single electron transfer reactions. J. Phys. Chem. B 116(3):1180-88
85. Pérez-González A, Galano A, Alvarez-Idaboy JR. 2014. Dihydroxybenzoic acids as free radical scavengers: mechanisms, kinetics, and trends in activity. New J. Chem. 38(6):2639-52
86. Praveena R, Sadasivam K, Deepha V, Sivakumar R. 2014. Antioxidant potential of orientin: a combined experimental and DFT approach. J. Mol. Struct. 1061(1):114-23
87. Primikyri A, Mazzone G, Lekka C, Tzakos AG, Russo N, Gerothanassis IP. 2015. Understanding zinc(II) chelation with quercetin and luteolin: a combinedNMRand theoretical study. J. Phys. Chem. B 119:83-95
88. PryorWA. 1986. Oxy-radicals and related species: their formation, lifetimes, and reactions. Annu. Rev. Physiol. 48:657-67
89. Pryor WA. 1988. Why is the hydroxyl radical the only radical that commonly adds to DNA Hypothesis: It has a rare combination of high electrophilicity, high thermochemical reactivity, and a mode of production that can occur near DNA. Free Radic. Biol. Med. 4(4):219-23
90. Prütz WA, Mönig H, Butler J, Land EJ. 1985. Reactions of nitrogen dioxide in aqueous model systems: oxidation of tyrosine units in peptides and proteins. Arch. Biochem. Biophys. 243(1):125-34
91. Radi R, Peluffo G, Alvarez MN, Naviliat M, Cayota A. 2001. Unraveling peroxynitrite formation in biological systems. Free Radic. Biol. Med. 30(5):463-88
92. Roleira FMF, Tavares-Da-Silva EJ, Varela CL, Costa SC, Silva T, et al. 2015. Plant derived and dietary phenolic antioxidants: anticancer properties. Food Chem. 183:235-58
93. Sakurai K, Sasabe H, Koga T, Konishi T. 2004. Mechanism of hydroxyl radical scavenging by rebamipide: identification ofmono-hydroxylated rebamipide as amajor reaction product. Free Radic. Res. 38(5):487-94
94. Sayre LM, Perry G, Smith MA. 2008. Oxidative stress and neurotoxicity. Chem. Res. Toxicol. 21(1):172-88
95. Sirjoosingh A, Hammes-Schiffer S. 2011. Proton-coupled electron transfer versus hydrogen atom transfer: generation of charge-localized diabatic states. J. Phys. Chem. A 115(11):2367-77
96. Squadrito GL, Pryor WA. 1998. Oxidative chemistry of nitric oxide: the roles of superoxide, peroxynitrite, and carbon dioxide. Free Radic. Biol. Med. 25(4-5):392-403
97. Sueishi Y, Hori M, Kita M, Kotake Y. 2011. Nitric oxide (NO) scavenging capacity of natural antioxidants. Food Chem. 129(3):866-70
98. Sunkireddy P, Jha SN, Kanwar JR, Yadav SC. 2013. Natural antioxidant biomolecules promises future nanomedicine based therapy for cataract. Colloids Surf. B 112:554-62
99. Tinkel J, Hassanain H, Khouri SJ. 2012. Cardiovascular antioxidant therapy: a review of supplements, pharmacotherapies, and mechanisms. Cardiol. Rev. 20(2):77-83
100. Tishchenko O, Truhlar DG, Ceulemans A, Minh TN. 2008. A unified perspective on the hydrogen atom transfer and proton-coupled electron transfer mechanisms in terms of topographic features of the ground and excited potential energy surfaces as exemplified by the reaction between phenol and radicals. J. Am. Chem. Soc. 130(22):7000-10
101. Vijayalaxmi, Reiter RJ, Tan DX, Herman TS, Thomas CR Jr. 2004. Melatonin as a radioprotective agent: a review. Int. J. Radiat. Oncol. 59(3):639-53
102. Vysakh A, RatheeshM, Rajmohanan TP, Pramod C, Premlal S, et al. 2014. Polyphenolics isolated from virgin coconut oil inhibits adjuvant induced arthritis in rats through antioxidant and anti-inflammatory action. Int. Immunopharmacol. 20(1):124-30
103. Weinstein J, Bielski BHJ. 1979. Kinetics of the interaction of HO2 and O2 radicals with hydrogen peroxide. The Haber-Weiss reaction. J. Am. Chem. Soc. 101(1):58-62
104. Widsten P, CruzCD, Fletcher GC, Pajak MA, McGhieTK. 2014. Tannins and extracts of fruit byproducts: antibacterial activity against foodborne bacteria and antioxidant capacity. J. Agric. Food Chem. 62(46):11146-56
105. Xue Y, Zheng Y, An L, Zhang L, Qian Y, et al. 2012. A theoretical study of the structure-radical scavenging activity of hydroxychalcones. Comput. Theor. Chem. 982:74-83
106. Yan XT, Lee SH, Li W, Sun YN, Yang SY, et al. 2014. Evaluation of the antioxidant and anti-osteoporosis activities of chemical constituents of the fruits of Prunus mume. Food Chem. 156:408-15