Immobilization of caffeic acid on a polypropylene film: Synthesis and antioxidant properties

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 16, 2010, Pages 9228-9234

  Arrua, Dario ^a   Strumia, Miriam Cristina ^b   Nazareno, Mónica Azucena ^a  

^a UNIVERSIDAD NACIONAL DE SANTIAGO DEL ESTERO   (Argentina)

^b UNIVERSIDAD NACIONAL DE CÓRDOBA   (Argentina)

Author keywords

Active packaging; Antioxidant; Antiradical activity; Grafting; Polyphenols

Indexed keywords

ACTIVE PACKAGING; ANTIOXIDANT; ANTIRADICAL ACTIVITY; GRAFTING; POLYPHENOLS;

CHLORINE COMPOUNDS; FRUIT JUICES; GRAFTING (CHEMICAL); KETONES; LINOLEIC ACID; ORGANIC ACIDS; OXIDATION; PHENOLS; PLASTIC FILMS; POLYMERS; SYNTHESIS (CHEMICAL); THERMOPLASTICS;

POLYMERIC FILMS;

ANTIOXIDANT; CAFFEIC ACID; CAFFEIC ACID DERIVATIVE; POLYPROPYLENE;

ARTICLE; CHEMISTRY; INFRARED SPECTROSCOPY;

ANTIOXIDANTS; CAFFEIC ACIDS; POLYPROPYLENES; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 77956541120     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf101651y     Document Type: Article

References (33)

1. Catalá, R.; Gavara, R. From the passive protection to the active defense of the packed foods. New Packages; Arbor CLXVIII; 2001; Vol. 661, pp 109-127.
2. Costamagna, V.; Wunderlin, D.; Larrañ aga, M.; Mondragó n, I.;Strumia, M. Surface functionalization of polyolefin films via the ultraviolet-induced photografting of acrylic acid: topographical characterization and ability for binding antifungal agents. J. Appl. Polym. Sci. 2006, 102, 2254-2263.
3. Costamagna, V.; Strumia, M.; López-Gonzá lez, M.; Riande, E. Gas transport in surface-modified low-density polyethylene films with acrylic acid as a grafting agent. J. Polym. Sci., Part B: Polym. Phys. 2006, 44, 2828-2840.
4. Costamagna, V.; Strumia, M.; López-Gonzá lez, M.; Riande, E. Gas transport in surface grafted polypropylene films with poly-(acrylic acid) chains. J. Polym. Sci., Part B: Polym. Phys. 2007, 45, 2421-2431.
5. Esumi, K.; Houdatsu, H.; Yoshimura, T. Antioxidant action by gold-Pamam dendrimer nanocomposites. Langmuir 2004, 20, 2536-2538.
6. Yu, R.; Mandlekar, S.; Kong, A. T. Molecular mechanisms of butylated hydroxylanisole-induced toxicity: induction of apoptosis through direct release of cytochrome c. Mol. Pharmacol. 2000, 58 (2), 431-437.
7. Kim, D. O.; Lee, C. Y. Comprehensive study on vitamin C equivalent antioxidant capacity (VCEAC) of various polyphenolics in scavenging a free radical and its structural relationship. Crit. Rev.Food Sci. Nutr. 2004, 44, 253-273.
8. Kim, D. O.; Lee, K. W.; Lee H. J.; Lee, C. Y. Vitamin C equivalent antioxidant capacity (VCEAC) of phenolic phytochemicals. J. Agric. Food Chem. 2002, 50, 3713-3717.
9. Chen, J. H.; Ho, C. T. Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds. J. Agric. Food Chem. 1997, 45, 2374-2378.
10. Chaillou, L.; Nazareno, M. New method to determine antioxidant activity of polyphenols. J. Agric. Food Chem. 2006, 54, 8397-8402.
11. Nerí́n, C.; Tovar, L.; Djenane, D.; Camo, J.; Salafranca, J. S.; Beltrán, J. A.; Roncalés, P. Stabilization of beef meat by a new active packaging containing natural antioxidants. J. Agric. Food Chem. 2006, 54, 7840-7846.
12. Arefev, D. V.; Belostotskaya, I. S.; Voleva, V. B.; Domnina, N. S.; Komissarova, N. L.; Sergeeva, O. Y.; Khrustaleva, R. S. Hybrid macromolecular antioxidants based on hydrophilic polymers and sterically hindered phenols. Russ. Chem. Bull.Int. Ed. 2007, 56, 781-790.
13. Curcio, M.; Puoci, F.; Iemma, F.; Parisi, O. I.; Cirillo, G.; Spizzirri,U. G.; Picci, N. Covalent insertion of antioxidant molecules on chitosan by a free radical grafting procedure. J. Agric. Food Chem. 2009, 57, 5933-5938.
14. Gao, X.; Hu, G.; Qian, Z.; Ding, Y.; Zhang, S.; Wang, D.; Yang, M.Immobilization of antioxidant on nanosilica and the antioxidative behavior in low density polyethylene. Polymer 2007, 48, 7309-7315.
15. Maeda, S.; Nonaka, T.; Ogata, T.; Kurihara, S. Synthesis of macroreticular copolymer beads having various phenolic erivatives immobilized via different bond and their radical scavenging activity.J. Appl. Polym. Sci. 2006, 102, 4791-4800. (Pubitemid 44784141)
16. Puoci, F.; Iemma, F.; Curcio, M.; Parisi, O. I.; Cirillo, G.; Spizzirri, U. G.; Picci, N. Synthesis of methacrylic-ferulic acid copolymer with antioxidant properties by single-step free radical polymerization. J. Agric. Food Chem. 2008, 56, 10646-10650.
17. Singleton, V.; Rossi, J. Colorimetry of total phenolics with phosphomolybdic-phosphotungstic acid reagents. Am. J. Enol. Vitic. 1995, 16, 144-158.
18. Brand-Williams, W.; Cuvelier, M. E.; Berset, E. Use of a free radical method to evaluate antioxidant activity. Lebensm.-Wiss. Technol. 1995, 28, 25-30.
19. Ozgen, M.; Reese, R. N.; Tulio, A. Z., Jr.; Scheerens, J. C.; Miller, A. R. Modified 2,2-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) method to measure antioxidant capacity of selected small fruits and comparison to ferric reducing antioxidant power (FRAP) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) methods. J. Agric. Food Chem. 2006 54, 1151-1157.
20. Burda, S.; Oleszek, W. Antioxidant and antiradical activities of flavonoids. J. Agric. Food Chem. 2001, 49, 2774-2779.
21. Savina, I.; Galaev, I.; Mattiasson, B. Anion-exchange supermacroporous monolithic matrices with grafted polymer brushes of N,Ndimethylaminoethyl- methacrylate. J. Chromatogr., A 2005, 1092, 199-205.
22. Tazuke, S.; Matoba, T.; Kimura, H.; Okada, T. A novel modification of polymer surfaces by photografting. In ACS Symposium Series 121: Modification of Polymers; American Chemical Society:Washington, DC, 1980; pp 217-241. (Pubitemid 10488837)
23. Lu, F.; Ralph, J. Facile synthesis of 4-hydroxycinnamyl p-coumarates. J. Agric. Food Chem. 1998, 46, 2911-2913.
24. Latha, G. M.; Srinivas, P.; Muralikrishna, G. Purification and characterization of ferulic acid esterase from malted finger millet (Eleusine coracana, Indaf-15). J. Agric. Food Chem. 2007, 55, 9704-9712.
25. Bergenudd, H.; Eriksson, P.; DeArmitt, C.; Stenberg, B.; Malmstrom Jonsson, E. Synthesis and evaluation of hyperbranched phenolic antioxidants of three different generations. Polym. Degrad. Stab. 2002, 76, 503-509.
26. Ou, S.; Li, A.; Yang, A.Astudy on synthesis of starch ferulate and its biological properties. Food Chem. 2001, 74, 91-95.
27. Nagaoka, T.; Banskota, A. H.; Tezuka, Y.; Saiki, I.; Kadota, S. Selective antiproliferative activity of caffeic acid phenethyl ester analogues on highly liver-metastatic murine colon 26-L5 carcinoma cell line. Biorg. Med. Chem. 2002, 10, 3351-3359.
28. Singleton, V. L.; Orthofer, R.; Lamuela-Raventos, R. M. Analysis of total phenols and other oxidation substrates and antioxidants by means of Folin-Ciocalteu reagent. Methods Enzymol. 1999, 299,152-178.
29. Yu, L.; Perret, J.; Harris, M.; Wilson, J.; Haley, S. Antioxidant properties of bran extracts from " Akron" wheat grown at different locations. J. Agric. Food Chem. 2003, 51, 1566-1570.
30. Pé rez, D. D.; Leigthon, F.; Aspee, A.; Aliaga, C.; Lissi, E. A. A comparison of methods employed to evaluate antioxidant capabilities. Biol. Res. 2000, 33, 71-77.
31. Chaillou, L. L.; Nazareno, M. A. Bioactivity of propolis from Santiago del Estero, Argentina, related to their chemical composition. LWT - Food Sci. Technol. 2009, 42, 1422-1427.
32. Özkan, M.; Kirca, A.; Cemeroglu, B. Effects of hydrogen peroxide on the stability of ascorbic acid during storage of various fruit juices.Food Chem. 2004, 88, 591-597.
33. Laranjinha, J.; Cadenas, E. Continuous-flow EPR measurements. Redox cycles of caffeic acid, α-tocopherol, and ascorbate: implications for protection of low-density lipoproteins against oxidation. IUBMB Life 1999, 48, 57-65.