In Vitro Antioxidant-Activity Evaluation of Gallic-Acid-Grafted Chitosan Conjugate Synthesized by Free-Radical-Induced Grafting Method

Journal of Agricultural and Food Chemistry

Volumn 64, Issue 29, 2016, Pages 5893-5900

  Hu, Qiaobin ^a   Wang, Taoran ^a   Zhou, Mingyong ^a   Xue, Jingyi ^a   Luo, Yangchao ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

antioxidant activity; chitosan; conjugate; free radical induced grafting method; gallic acid

Indexed keywords

AGENTS; ANTIOXIDANTS; ASCORBIC ACID; CHITIN; CHITOSAN; FOURIER TRANSFORM INFRARED SPECTROSCOPY; GRAFTING (CHEMICAL); ORGANIC ACIDS; X RAY DIFFRACTION;

2 ,2-DIPHENYL-1-PICRYLHYDRAZYL; ANTI-OXIDANT ACTIVITIES; CONJUGATE; EQUIVALENT CONCENTRATIONS; GALLIC ACIDS; GRAFTING METHOD; PHYSICOCHEMICAL PROPERTY; WATER-SOLUBLE CHITOSAN;

FREE RADICALS;

ANTIOXIDANT; CHITOSAN; FREE RADICAL; GALLIC ACID;

CHEMISTRY; GREEN CHEMISTRY; X RAY DIFFRACTION;

ANTIOXIDANTS; CHITOSAN; FREE RADICALS; GALLIC ACID; GREEN CHEMISTRY TECHNOLOGY; X-RAY DIFFRACTION;

EID: 84979752447     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/acs.jafc.6b02255     Document Type: Article

References (44)

1. Kean, T.; Thanou, M. Biodegradation, biodistribution and toxicity of chitosan Adv. Drug Delivery Rev. 2010, 62, 3-11 10.1016/j.addr.2009.09.004
2. Xia, W.; Liu, P.; Zhang, J.; Chen, J. Biological activities of chitosan and chitooligosaccharides Food Hydrocolloids 2011, 25, 170-179 10.1016/j.foodhyd.2010.03.003
3. Rinaudo, M. Chitin and chitosan: properties and applications Prog. Polym. Sci. 2006, 31, 603-632 10.1016/j.progpolymsci.2006.06.001
4. Kim, H.; Tator, C. H.; Shoichet, M. S. Chitosan implants in the rat spinal cord: biocompatibility and biodegradation J. Biomed. Mater. Res., Part A 2011, 97, 395-404 10.1002/jbm.a.33070
5. Yue, L.; Zhang, L.; Zhong, H. Carboxymethyl chitosan: A new water soluble binder for Si anode of Li-ion batteries J. Power Sources 2014, 247, 327-331 10.1016/j.jpowsour.2013.08.073
6. Ma, Q.; Lin, Z.-H.; Yang, N.; Li, Y.; Su, X.-G. A novel carboxymethyl chitosan-quantum dot-based intracellular probe for Zn 2+ ion sensing in prostate cancer cells Acta Biomater. 2014, 10, 868-874 10.1016/j.actbio.2013.10.039
7. Mukhopadhyay, P.; Sarkar, K.; Bhattacharya, S.; Bhattacharyya, A.; Mishra, R.; Kundu, P. pH sensitive N-succinyl chitosan grafted polyacrylamide hydrogel for oral insulin delivery Carbohydr. Polym. 2014, 112, 627-637 10.1016/j.carbpol.2014.06.045
8. Dadhich, P.; Das, B.; Dhara, S. Microwave assisted rapid synthesis of N-methylene phosphonic chitosan via Mannich-type reaction Carbohydr. Polym. 2015, 133, 345-352 10.1016/j.carbpol.2015.06.105
9. Hu, B.; Wang, Y.; Xie, M.; Hu, G.; Ma, F.; Zeng, X. Polymer nanoparticles composed with gallic acid grafted chitosan and bioactive peptides combined antioxidant, anticancer activities and improved delivery property for labile polyphenols J. Funct. Foods 2015, 15, 593-603 10.1016/j.jff.2015.04.009
10. Liu, J.; Lu, J. F.; Kan, J.; Jin, C. H. Synthesis of chitosan-gallic acid conjugate: structure characterization and in vitro anti-diabetic potential Int. J. Biol. Macromol. 2013, 62, 321-329 10.1016/j.ijbiomac.2013.09.032
11. Liu, J.; Wen, X. Y.; Lu, J. F.; Kan, J.; Jin, C. H. Free radical mediated grafting of chitosan with caffeic and ferulic acids: structures and antioxidant activity Int. J. Biol. Macromol. 2014, 65, 97-106 10.1016/j.ijbiomac.2014.01.021
12. Cirillo, G.; Curcio, M.; Vittorio, O.; Iemma, F.; Restuccia, D.; Spizzirri, U. G.; Puoci, F.; Picci, N. Polyphenol conjugates and human health: a perspective review Crit. Rev. Food Sci. Nutr. 2016, 56, 326-337 10.1080/10408398.2012.752342
13. Xiao, J.; Kai, G. A review of dietary polyphenol-plasma protein interactions: Characterization, influence on the bioactivity, and structure-affinity relationship Crit. Rev. Food Sci. Nutr. 2012, 52, 85-101 10.1080/10408398.2010.499017
14. Pasanphan, W.; Chirachanchai, S. Conjugation of gallic acid onto chitosan: An approach for green and water-based antioxidant Carbohydr. Polym. 2008, 72, 169-177 10.1016/j.carbpol.2007.08.002
15. Božič, M.; Gorgieva, S.; Kokol, V. Laccase-mediated functionalization of chitosan by caffeic and gallic acids for modulating antioxidant and antimicrobial properties Carbohydr. Polym. 2012, 87, 2388-2398 10.1016/j.carbpol.2011.11.006
16. Wu, X.-f.; Liu, W.; Lu, M.; Chen, J.-w. Synthesis of Chitosan-g-(salicylic acid) Chinese Journal of Synthetic Chemistry 2005, 13, 461
17. Jung, B.-O.; Chung, S.-J.; Lee, S. B. Preparation and characterization of eugenol-grafted chitosan hydrogels and their antioxidant activities J. Appl. Polym. Sci. 2006, 99, 3500-3506 10.1002/app.22974
18. Cho, Y.-S.; Kim, S.-K.; Ahn, C.-B.; Je, J.-Y. Preparation, characterization, and antioxidant properties of gallic acid-grafted-chitosans Carbohydr. Polym. 2011, 83, 1617-1622 10.1016/j.carbpol.2010.10.019
19. Senevirathne, M.; Jeon, Y.-J.; Kim, Y.-T.; Park, P.-J.; Jung, W.-K.; Ahn, C.-B.; Je, J.-Y. Prevention of oxidative stress in Chang liver cells by gallic acid-grafted-chitosans Carbohydr. Polym. 2012, 87, 876-880 10.1016/j.carbpol.2011.08.080
20. 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 10.1021/jf900778u
21. Nurmi, K.; Ossipov, V.; Haukioja, E.; Pihlaja, K. Variation of total phenolic content and individual low-molecular-weight phenolics in foliage of mountain birch trees (Betula pubescens ssp. tortuosa) J. Chem. Ecol. 1996, 22, 2023-2040 10.1007/BF02040093
22. Dudonne, S.; Vitrac, X.; Coutiere, P.; Woillez, M.; Mérillon, J.-M. Comparative study of antioxidant properties and total phenolic content of 30 plant extracts of industrial interest using DPPH, ABTS, FRAP, SOD, and ORAC assays J. Agric. Food Chem. 2009, 57, 1768-1774 10.1021/jf803011r
23. Xie, M.; Hu, B.; Wang, Y.; Zeng, X. Grafting of gallic acid onto chitosan enhances antioxidant activities and alters rheological properties of the copolymer J. Agric. Food Chem. 2014, 62, 9128-9136 10.1021/jf503207s
24. Woranuch, S.; Yoksan, R. Preparation, characterization and antioxidant property of water-soluble ferulic acid grafted chitosan Carbohydr. Polym. 2013, 96, 495-502 10.1016/j.carbpol.2013.04.006
25. Zulueta, A.; Esteve, M. J.; Frígola, A. ORAC and TEAC assays comparison to measure the antioxidant capacity of food products Food Chem. 2009, 114, 310-316 10.1016/j.foodchem.2008.09.033
26. Lee, D. S.; Woo, J. Y.; Ahn, C. B.; Je, J. Y. Chitosan-hydroxycinnamic acid conjugates: preparation, antioxidant and antimicrobial activity Food Chem. 2014, 148, 97-104 10.1016/j.foodchem.2013.10.019
27. Mohammed-Ziegler, I.; Billes, F. Vibrational spectroscopic calculations on pyrogallol and gallic acid J. Mol. Struct.: THEOCHEM 2002, 618, 259-265 10.1016/S0166-1280(02)00547-X
28. Liu, J.; Lu, J. F.; Kan, J.; Tang, Y. Q.; Jin, C. H. Preparation, characterization and antioxidant activity of phenolic acids grafted carboxymethyl chitosan Int. J. Biol. Macromol. 2013, 62, 85-93 10.1016/j.ijbiomac.2013.08.040
29. Liu, Y.; Zhang, B.; Javvaji, V.; Kim, E.; Lee, M. E.; Raghavan, S. R.; Wang, Q.; Payne, G. F. Tyrosinase-mediated grafting and crosslinking of natural phenols confers functional properties to chitosan Biochem. Eng. J. 2014, 89, 21-27 10.1016/j.bej.2013.11.016
30. Zhang, H.; Li, S.; White, C. J. B.; Ning, X.; Nie, H.; Zhu, L. Studies on electrospun nylon-6/chitosan complex nanofiber interactions Electrochim. Acta 2009, 54, 5739-5745 10.1016/j.electacta.2009.05.021
31. Zhu, Q.-L.; Zhou, Y.; Guan, M.; Zhou, X.-F.; Liu, Y.; Chen, W.-L.; Zhang, C.-G.; Yuan, Z.-Q.; Liu, C.; Zhu, A.-J.; Yang, S.-D.; Zhang, X.-N. Low-density lipoprotein-coupled N-succinyl chitosan nanoparticles co-delivering siRNA and doxorubicin for hepatocyte-targeted therapy Biomaterials 2014, 35, 5965-5976 10.1016/j.biomaterials.2014.03.088
32. Qi, L.; Xu, Z.; Jiang, X.; Hu, C.; Zou, X. Preparation and antibacterial activity of chitosan nanoparticles Carbohydr. Res. 2004, 339, 2693-2700 10.1016/j.carres.2004.09.007
33. Pasanphan, W.; Buettner, G. R.; Chirachanchai, S. Chitosan conjugated with deoxycholic acid and gallic acid: A novel biopolymer-based additive antioxidant for polyethylene J. Appl. Polym. Sci. 2008, 109, 38-46 10.1002/app.27953
34. OSAWA, R.; WALSH, T. P. Detection of bacterial gallate decarboxylation by visual color discrimination J. Gen. Appl. Microbiol. 1995, 41, 165-170 10.2323/jgam.41.165
35. Valko, M.; Rhodes, C.; Moncol, J.; Izakovic, M.; Mazur, M. Free radicals, metals and antioxidants in oxidative stress-induced cancer Chem.-Biol. Interact. 2006, 160, 1-40 10.1016/j.cbi.2005.12.009
36. Pasanphan, W.; Buettner, G. R.; Chirachanchai, S. Chitosan gallate as a novel potential polysaccharide antioxidant: an EPR study Carbohydr. Res. 2010, 345, 132-40 10.1016/j.carres.2009.09.038
37. Božič, M.; Štrancar, J.; Kokol, V. Laccase-initiated reaction between phenolic acids and chitosan React. Funct. Polym. 2013, 73, 1377-1383 10.1016/j.reactfunctpolym.2013.01.005
38. Pasanphan, W.; Buettner, G. R.; Chirachanchai, S. Chitosan conjugated with deoxycholic acid and gallic acid: A novel biopolymer-based additive antioxidant for polyethylene J. Appl. Polym. Sci. 2008, 109, 38-46 10.1002/app.27953
39. Zhu, W.; Zhang, Z. Preparation and characterization of catechin-grafted chitosan with antioxidant and antidiabetic potential Int. J. Biol. Macromol. 2014, 70, 150-155 10.1016/j.ijbiomac.2014.06.047
40. Yu, S.-H.; Mi, F.-L.; Pang, J.-C.; Jiang, S.-C.; Kuo, T.-H.; Wu, S.-J.; Shyu, S.-S. Preparation and characterization of radical and pH-responsive chitosan-gallic acid conjugate drug carriers Carbohydr. Polym. 2011, 84, 794-802 10.1016/j.carbpol.2010.04.035
41. Aljawish, A.; Chevalot, I.; Piffaut, B.; Rondeau-Mouro, C.; Girardin, M.; Jasniewski, J.; Scher, J.; Muniglia, L. Functionalization of chitosan by laccase-catalyzed oxidation of ferulic acid and ethyl ferulate under heterogeneous reaction conditions Carbohydr. Polym. 2012, 87, 537-544 10.1016/j.carbpol.2011.08.016
42. Thaipong, K.; Boonprakob, U.; Crosby, K.; Cisneros-Zevallos, L.; Byrne, D. H. Comparison of ABTS, DPPH, FRAP, and ORAC assays for estimating antioxidant activity from guava fruit extracts J. Food Compos. Anal. 2006, 19, 669-675 10.1016/j.jfca.2006.01.003
43. Casettari, L.; Gennari, L.; Angelino, D.; Ninfali, P.; Castagnino, E. ORAC of chitosan and its derivatives Food Hydrocolloids 2012, 28, 243-247 10.1016/j.foodhyd.2012.01.005
44. Lee, D. S.; Eom, S. H.; Kim, Y. M.; Kim, H. S.; Yim, M. J.; Lee, S. H.; Kim, D. H.; Je, J. Y. Antibacterial and synergic effects of gallic acid-grafted-chitosan with beta-lactams against methicillin-resistant Staphylococcus aureus (MRSA) Can. J. Microbiol. 2014, 60, 629-638 10.1139/cjm-2014-0286