DOI: https://doi.org/10.14710/jksa.27.9.409-418

Synthesis of Sulfonated Chitosan as An Active Agent of Antibacterial Packaging for Fish Fillets

1Chemistry Department, Faculty of Sciences and Mathematics, Diponegoro University, Jl. Prof. Soedarto, SH., Tembalang, Semarang, Indonesia

2 National Environmental Public Health Laboratory, Ministry of Health, Salatiga, Indonesia

Received: 30 May 2024; Revised: 20 Aug 2024; Accepted: 26 Aug 2024; Published: 30 Sep 2024.
Open Access Copyright 2024 Jurnal Kimia Sains dan Aplikasi under http://creativecommons.org/licenses/by-sa/4.0.

Citation Format:
Cover Image
Abstract

Modifying chitosan by increasing its hydrophilic properties through sulfonation reactions will increase its solubility in water and antibacterial activity and expand the application of chitosan. This study aims to determine the antibacterial activity of sulfonated chitosan film applied as fish fillet packaging using the total plate count method. Sulfonated chitosan in this study was successfully synthesized by reacting chitosan with 1,3-propane sultone. Sulfonated chitosan products were characterized using FTIR and UV-Vis spectrophotometers, while antibacterial activity was measured using the disc diffusion method. The optimum temperature for sulfonated chitosan synthesis was 60°C (SCS60). The resulting SCS 60 was a yellowish-white solid soluble in water with a yield of 61.46% and a degree of substitution of 33%. The diameters of the SCS 60 inhibition zone against E. coli and S. aureus isolates were 7 and 10 mm, respectively. SCS60-gelatin film is elastic (elongation 272%) and more hydrophobic with a contact angle of 90.12° compared to chitosan-gelatin film (62.8°). SCC60-gelatin film was able to suppress bacterial growth in fish fillets by up to 0.3 × 104 cfu/g compared to unpackaged fish (30 × 104 cfu/g). Sulfonated chitosan has the potential to be an antibacterial food packaging material.

Fulltext View|Download
Keywords: Chitosan; sulfonated chitosan; antibacterial; fillet fish; 1,3-propane sultone
Funding: Penelitian Madya Sumber Dana Selain APBN FSM UNDIP under contract 20/UN7.F8/HK/II/2024

Article Metrics:

Article Info
Section: Research Articles
Language : EN
Recent articles
Synthesis of Sulfonated Chitosan as An Active Agent of Antibacterial Packaging for Fish Fillets Development of the Diffusive Gradient in Thin Film (DGT) Method with CaO/Biochar Binding Agent from Eggshells and Rice Straw Waste for Determining the Concentration of Phosphate Design and In-silico Study of ¹³¹Iodium Radiolabeled of Thiourea derivatives for Breast Cancer Treatment More recent articles
Most cited articles
Sintesis Metil Eugenol dan Benzil Eugenol dari Minyak Daun Cengkeh New Chemicals and Routes for the Preparation of Gelatin/HA Composites using the Wet Precipitation Method Pengaruh Diameter Kanal Pelet Katalis Zeolit Aktif dan Ni-Zeolit terhadap Pirolisis Limbah Batang Pohon Sagu (Metroxylonsp.) Isolation of Flavonoid Compounds from Eceng Gondok (Eichhornia crassipes) and Antioxidant Tests with DPPH (1,1-Diphenyl-2-Picrylhydrazyl) Method Biolubrication Synthesis Made from Used Cooking Oil and Bayah Natural Zeolite Catalyst More cited articles
  1. M. S. Alamri, Akram A. A. Qasem, Abdellatif A. Mohamed, Shahzad Hussain, Mohamed A. Ibraheem, Ghalia Shamlan, Hesham A. Alqah, Ali S. Qasha, Food packaging’s materials: A food safety perspective, Saudi Journal of Biological Sciences, 28, 8, (2021), 4490-4499 https://doi.org/10.1016/j.sjbs.2021.04.047
  2. Shraddha Karanth, Shuyi Feng, Debasmita Patra, Abani K. Pradhan, Linking microbial contamination to food spoilage and food waste: the role of smart packaging, spoilage risk assessments, and date labeling, Frontiers in Microbiology, 14, (2023), 1198124 https://doi.org/10.3389/fmicb.2023.1198124
  3. Jiaqi Lan, Shuo Yang, Yu Wang, Nan Guo, Xu Liu, Ketong Zhu, Pingsheng Gong, Shaowu Lv, Evaluation of Microbial Contamination in Cold Dishes and Prevalence of Foodborne Pathogens in Jilin Province, Journal of Food Protection, 85, 5, (2022), 728-734 https://doi.org/10.4315/JFP-21-328
  4. Tobi Fadiji, Mahdi Rashvand, Michael O. Daramola, Samuel A. Iwarere, A Review on Antimicrobial Packaging for Extending the Shelf Life of Food, Processes, 11, 2, (2023), 590 https://doi.org/10.3390/pr11020590
  5. Omar M. Khubiev, Anton R. Egorov, Anatoly A. Kirichuk, Victor N. Khrustalev, Alexander G. Tskhovrebov, Andreii S. Kritchenkov, Chitosan-Based Antibacterial Films for Biomedical and Food Applications, International Journal of Molecular Sciences, 24, 13, (2023), 10738 https://doi.org/10.3390/ijms241310738
  6. P. Fernández-Saiz, G. Sánchez, C. Soler, J. M. Lagaron, M. J. Ocio, Chitosan films for the microbiological preservation of refrigerated sole and hake fillets, Food Control, 34, 1, (2013), 61-68 https://doi.org/10.1016/j.foodcont.2013.03.047
  7. Rika Silvia, Sari Wahyu Waryani, Farida Hanum, Pemanfaatan kitosan dari cangkang rajungan (Portonus sanginolentus L.) sebagai pengawet ikan kembung (Rastrelliger sp) dan ikan lele (Clarias Batrachus), Jurnal Teknik Kimia USU, 3, 4, (2014), 18-24 https://doi.org/10.32734/jtk.v3i4.1651
  8. Mamiek Mardyaningsih, Aloysius Leki, Oktovianus D. Rerung, Pembuatan Kitosan dari Kulit dan Kepala Udang Laut Perairan Kupang Sebagai Pengawet Ikan Teri Segar, Jurnal Rekayasa Proses, 8, 2, (2016), 69-75
  9. C. O. Mohan, C. N. Ravishankar, K. V. Lalitha, T. K. Srinivasa Gopal, Effect of chitosan edible coating on the quality of double filleted Indian oil sardine (Sardinella longiceps) during chilled storage, Food Hydrocolloids, 26, 1, (2012), 167-174 https://doi.org/10.1016/j.foodhyd.2011.05.005
  10. Franklin Bonilla, Alexander Chouljenko, Vondel Reyes, Peter J. Bechtel, Joan M. King, Subramaniam Sathivel, Impact of chitosan application technique on refrigerated catfish fillet quality, LWT, 90, (2018), 277-282 https://doi.org/10.1016/j.lwt.2017.12.010
  11. Cai-Ling Ke, Fu-Sheng Deng, Chih-Yu Chuang, Ching-Hsuan Lin, Antimicrobial Actions and Applications of Chitosan, Polymers, 13, 6, (2021), 904 https://doi.org/10.3390/polym13060904
  12. Khaled M. El-Khawas, Bassam H. Mashat, Osama A. Attala, Gehan M. A. Kassem, Control of Salmonella and Escherichia coli in chilled chicken fillets using chitosan and lactic acid, CyTA - Journal of Food, 18, 1, (2020), 445-450 https://doi.org/10.1080/19476337.2020.1772887
  13. E. Latou, S. F. Mexis, A. V. Badeka, S. Kontakos, M. G. Kontominas, Combined effect of chitosan and modified atmosphere packaging for shelf life extension of chicken breast fillets, LWT - Food Science and Technology, 55, 1, (2014), 263-268 https://doi.org/10.1016/j.lwt.2013.09.010
  14. Vangelis Economou, Anestis Tsitsos, Alexandros Theodoridis, Ioannis Ambrosiadis, Georgios Arsenos, Effects of Chitosan Coatings on Controlling Listeria monocytogenes and Methicillin-Resistant Staphylococcus aureus in Beef and Mutton Cuts, Applied Sciences, 12, 22, (2022), 11345 https://doi.org/10.3390/app122211345
  15. M. Yildirim‐Aksoy, B.H. Beck, Antimicrobial activity of chitosan and a chitosan oligomer against bacterial pathogens of warmwater fish, Journal of Applied Microbiology, 122, 6, (2017), 1570-1578 https://doi.org/10.1111/jam.13460
  16. Juan D. Giraldo, Bernabé L. Rivas, Direct ionization and solubility of chitosan in aqueous solutions with acetic acid, Polymer Bulletin, 78, 3, (2021), 1465-1488 https://doi.org/10.1007/s00289-020-03172-w
  17. Nurul Liyana Lukman Hekiem, Aliza Aini Md Ralib, Maziati Akmal Mohd Hatta, Farah B. Ahmad, Anis Nurashikin Nordin, Rosminazuin Ab Rahim, Nor Farahidah Za'bah, Effect of chitosan dissolved in different acetic acid concentration towards VOC sensing performance of quartz crystal microbalance overlay with chitosan, Materials Letters, 291, (2021), 129524 https://doi.org/10.1016/j.matlet.2021.129524
  18. Julia Menegotto Frick Pavoni, Cláudia Leites Luchese, Isabel Cristina Tessaro, Impact of acid type for chitosan dissolution on the characteristics and biodegradability of cornstarch/chitosan based films, International Journal of Biological Macromolecules, 138, (2019), 693-703 https://doi.org/10.1016/j.ijbiomac.2019.07.089
  19. Jie Xu, Kun Liu, Wei Chang, Bor-Sen Chiou, Maoshen Chen, Fei Liu, Regulating the Physicochemical Properties of Chitosan Films through Concentration and Neutralization, Foods, 11, 11, (2022), 1657 https://doi.org/10.3390/foods11111657
  20. Luqing Cui, Shanshan Gao, Xiaoming Song, Lianqing Huang, Hehe Dong, Jinling Liu, Fushan Chen, Shitao Yu, Preparation and characterization of chitosan membranes, RSC Advances, 8, 50, (2018), 28433-28439 https://doi.org/10.1039/C8RA05526B
  21. Roberto Casalini, Filippo Ghisoni, Lorenzo Bonetti, Andrea Fiorati, Luigi De Nardo, Development of acid-free chitosan films in food coating applications: Provolone cheese as a case study, Carbohydrate Polymers, 331, (2024), 121842 https://doi.org/10.1016/j.carbpol.2024.121842
  22. Riccardo Toscani, Chitosan Film Formulations for Food Packaging: A Comparative Study of Acidic and Acid-Free Films, School of Industrial and Information Engineering, Politecnico di Milano, 2023
  23. Jianlong Wang, Shuting Zhuang, Chitosan-based materials: Preparation, modification and application, Journal of Cleaner Production, 355, (2022), 131825 https://doi.org/10.1016/j.jclepro.2022.131825
  24. Meenakshi Yadav, Babita Kaushik, Gyaneshwar K. Rao, Chandra Mohan Srivastava, Dipti Vaya, Advances and challenges in the use of chitosan and its derivatives in biomedical fields: A review, Carbohydrate Polymer Technologies and Applications, 5, (2023), 100323 https://doi.org/10.1016/j.carpta.2023.100323
  25. Suryani Suryani, Anis Yohana Chaerunisaa, I Made Joni, Ruslin Ruslin, Vica Aspadiah, Anton Anton, Ari Sartinah, La Ode Ahmad Nur Ramadhan, The Chemical Modification to Improve Solubility of Chitosan and Its Derivatives Application, Preparation Method, Toxicity as a Nanoparticles, Nanotechnology, Science Applications, 17, (2024), 41-57 https://doi.org/10.2147/NSA.S450026
  26. Weixiang Liu, Yukun Qin, Pengcheng Li, Design of Chitosan Sterilization Agents by a Structure Combination Strategy and Their Potential Application in Crop Protection, Molecules, 26, 11, (2021), 3250 https://doi.org/10.3390/molecules26113250
  27. Xiaoxiang Han, Zhehao Zheng, Chen Yu, Yunli Deng, Qing Ye, Fuge Niu, Qing Chen, Weichun Pan, Yanbo Wang, Preparation, characterization and antibacterial activity of new ionized chitosan, Carbohydrate Polymers, 290, (2022), 119490 https://doi.org/10.1016/j.carbpol.2022.119490
  28. Lin Wang, Yu Pang, Zhongwen Su, Meihua Xin, Mingchun Li, Yangfan Mao, Synthesis of N-isonicotinic sulfonate chitosan and its antibiofilm activity against E. coli and S. aureus, Carbohydrate Research, 542, (2024), 109194 https://doi.org/10.1016/j.carres.2024.109194
  29. Zhimin Sun, Changgu Shi, Xiangyang Wang, Qiang Fang, Jianying Huang, Synthesis, characterization, and antimicrobial activities of sulfonated chitosan, Carbohydrate Polymers, 155, (2017), 321-328 https://doi.org/10.1016/j.carbpol.2016.08.069
  30. Chee-Shan Chen, Wan-Yu Liau, Guo-Jane Tsai, Antibacterial Effects of N-Sulfonated and N-Sulfobenzoyl Chitosan and Application to Oyster Preservation, Journal of Food Protection, 61, 9, (1998), 1124-1128 https://doi.org/10.4315/0362-028X-61.9.1124
  31. Han-Fen Huang, Chien-Fang Peng, Antibacterial and antifungal activity of alkylsulfonated chitosan, Biomarkers and Genomic Medicine, 7, 2, (2015), 83-86 https://doi.org/10.1016/j.bgm.2014.09.001
  32. Jianying Huang, Yuhong Liu, Lijun Yang, Fengyan Zhou, Synthesis of sulfonated chitosan and its antibiofilm formation activity against E. coli and S. aureus, International Journal of Biological Macromolecules, 129, (2019), 980-988 https://doi.org/10.1016/j.ijbiomac.2019.02.079
  33. George A. F. Roberts, Julian G. Domszy, Determination of the viscometric constants for chitosan, International Journal of Biological Macromolecules, 4, 6, (1982), 374-377 https://doi.org/10.1016/0141-8130(82)90074-5
  34. Shobhan Sabnis, Lawrence H. Block, Improved infrared spectroscopic method for the analysis of degree of N-deacetylation of chitosan, Polymer Bulletin, 39, (1997), 67-71 https://doi.org/10.1007/s002890050121
  35. S. Bagheri-Khoulenjani, S. M. Taghizadeh, H. Mirzadeh, An investigation on the short-term biodegradability of chitosan with various molecular weights and degrees of deacetylation, Carbohydrate Polymers, 78, 4, (2009), 773-778 https://doi.org/10.1016/j.carbpol.2009.06.020
  36. Eli Rohaeti, Anna Rakhmawati, Application of Terminalia catappa in Preparation of Silver Nanoparticles to Develop Antibacterial Nylon, Oriental Journal of Chemistry, 33, 6, (2017), 2905-2912 http://dx.doi.org/10.13005/ojc/330625
  37. Jan Hudzicki, Kirby-Bauer Disk Diffusion Susceptibility Test Protocol, American Society for Microbiology, 15, 1, (2009), 1-23
  38. Shun-Hsien Chang, Ying-Ju Chen, Hsiang-Jung Tseng, Hsin-I Hsiao, Huey-Jine Chai, Kuo-Chung Shang, Chorng-Liang Pan, Guo-Jane Tsai, Antibacterial Activity of Chitosan–Polylactate Fabricated Plastic Film and Its Application on the Preservation of Fish Fillet, Polymers, 13, 5, (2021), 696 https://doi.org/10.3390/polym13050696
  39. Ramón Román-Doval, Sandra P. Torres-Arellanes, Aldo Y. Tenorio-Barajas, Alejandro Gómez-Sánchez, Anai A. Valencia-Lazcano, Chitosan: Properties and Its Application in Agriculture in Context of Molecular Weight, Polymers, 15, 13, (2023), 2867 https://doi.org/10.3390/polym15132867
  40. Casper Van Poucke, Aurèle Vandeputte, Sven Mangelinckx, Christian V. Stevens, Green mechanochemical synthesis of water-soluble N-sulfonated chitosan, Green Chemistry, 25, 11, (2023), 4271-4281 https://doi.org/10.1039/D3GC00549F
  41. T. M. Tamer, A. M. Omer, M. M. Sabet, M. Elsayed Youssef, A. I. Hashem, M. S. Mohy Eldin, Development of polyelectrolyte sulfonated chitosan-alginate as an alternative methanol fuel cell membrane, Desalination and Water Treatment, 227, (2021), 132-148 https://doi.org/10.5004/dwt.2021.27290
  42. Tan Wang, Yue Zhou, Weiguo Xie, Lingyun Chen, Hua Zheng, Lihong Fan, Preparation and anticoagulant activity of N-succinyl chitosan sulfates, International Journal of Biological Macromolecules, 51, 5, (2012), 808-814 https://doi.org/10.1016/j.ijbiomac.2012.07.029
  43. Syang-Peng Rwei, Chia-Chun Lien, Synthesis and viscoelastic characterization of sulfonated chitosan solutions, Colloid and Polymer Science, 292, 4, (2014), 785-795 https://doi.org/10.1007/s00396-013-3115-6
  44. Anton R. Egorov, Anatoly A. Kirichuk, Vasili V. Rubanik, Vasili V. Rubanik, Alexander G. Tskhovrebov, Andreii S. Kritchenkov, Chitosan and Its Derivatives: Preparation and Antibacterial Properties, Materials, 16, 18, (2023), 6076 https://doi.org/10.3390/ma16186076
  45. Zhaodong Wang, Liuchun Zheng, Chuncheng Li, Shaohua Wu, Yaonan Xiao, Preparation and antimicrobial activity of sulfopropyl chitosan in an ionic liquid aqueous solution, Journal of Applied Polymer Science, 134, 26, (2017), 44989 https://doi.org/10.1002/app.44989
  46. Anna Guarnieri, Micaela Triunfo, Carmen Scieuzo, Dolores Ianniciello, Elena Tafi, Thomas Hahn, Susanne Zibek, Rosanna Salvia, Angela De Bonis, Patrizia Falabella, Antimicrobial properties of chitosan from different developmental stages of the bioconverter insect Hermetia illucens, Scientific Reports, 12, (2022), 8084 https://doi.org/10.1038/s41598-022-12150-3
  47. Dazhong Yan, Yanzhen Li, Yinling Liu, Na Li, Xue Zhang, Chen Yan, Antimicrobial Properties of Chitosan and Chitosan Derivatives in the Treatment of Enteric Infections, Molecules, 26, 23, (2021), 7136 https://doi.org/10.3390/molecules26237136
  48. Sara gamil Abd-elnaeem, Azza Ibrahim Hafez, kamel M. El-Khatib, Heba Abdallah Mohamed, Mai Mohamed Kamal El Din Fouad, Ehab Abadir, Parameters Affecting Synthesis of Sulfonated Chitosan Membrane for Proton Exchange Membrane in Fuel Cells, Egyptian Journal of Chemistry, 67, 5, (2024), 191-204 https://doi.org/10.21608/ejchem.2023.230907.8651
  49. Hongxia Wang, Fuyuan Ding, Liang Ma, Yuhao Zhang, Edible films from chitosan-gelatin: Physical properties and food packaging application, Food Bioscience, 40, (2021), 100871 https://doi.org/10.1016/j.fbio.2020.100871
  50. Abdolreza Farhadian, Mikhail A. Varfolomeev, Alireza Shaabani, Saeed Nasiri, Iskander Vakhitov, Yulia F. Zaripova, Vladimir V. Yarkovoi, Aleksander V. Sukhov, Sulfonated chitosan as green and high cloud point kinetic methane hydrate and corrosion inhibitor: Experimental and theoretical studies, Carbohydrate Polymers, 236, (2020), 116035 https://doi.org/10.1016/j.carbpol.2020.116035
  51. Xin Li, Fenghong Li, Xuan Zhang, Weiyuan Tang, Mingzheng Huang, Qun Huang, Zongcai Tu, Interaction mechanisms of edible film ingredients and their effects on food quality, Current Research in Food Science, 8, (2024), 100696 https://doi.org/10.1016/j.crfs.2024.100696
  52. Marina Ramos, Arantzazu Valdés, Ana Beltrán, María Carmen Garrigós, Gelatin-Based Films and Coatings for Food Packaging Applications, Coatings, 6, 4, (2016), 41 https://doi.org/10.3390/coatings6040041
  53. Yanan Lu, Qijun Luo, Yuchan Chu, Ningping Tao, Shanggui Deng, Li Wang, Li Li, Application of Gelatin in Food Packaging: A Review, Polymers, 14, 3, (2022), 436 https://doi.org/10.3390/polym14030436
  54. Weiping Ban, Jianguo Song, Dimitris S. Argyropoulos, Lucian A. Lucia, Influence of Natural Biomaterials on the Elastic Properties of Starch-Derived Films: An Optimization Study, Industrial & Engineering Chemistry Research, 45, 2, (2006), 627-633 https://doi.org/10.1021/ie050219s
  55. Natalia Wrońska, Nadia Katir, Marta Nowak-Lange, Abdelkrim El Kadib, Katarzyna Lisowska, Biodegradable Chitosan-Based Films as an Alternative to Plastic Packaging, Foods, 12, 18, (2023), 3519 https://doi.org/10.3390/foods12183519

Last update:

No citation recorded.

Last update: 2024-10-29 17:08:47

No citation recorded.