β-Cyclodextrin-grafted TEMPO-oxidized cellulose nanofibers for sustained release of essential oil
Source abstract
Abstract
The present investigation deals with the development and characterization of a new controlled release packaging system for food. Novel sustained system was developed by direct grafting of beta-cyclodextrin (βCD) on the carboxyl groups of TEMPO-oxidized cellulose nanofibers (TEMPO-CNF) in aqueous solution and without using any spacer. Carvacrol, an aromatic essential oil component, was then entrapped in the ensued CD-grafted TEMPO-CNF. Successful functionalization of TEMPO-CNF was confirmed by conductometric titration, Fourier Transform Infrared Spectroscopy, and gravimetric analyses. The βCD-grafted TEMPO-CNF films exhibited sustained release of carvacrol over 150 h before reaching the equilibrium in water. Antimicrobial activity of carvacrol against Bacillus subtilis was increased (or improved by 47 h) from 3 h when using TEMPO-CNF to around (or against) 50 h when using CD-grafted TEMPO-CNF. These promising results pave the way for the development of new bio-based controlled release packaging materials with efficient antibacterial activity.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Advanced Cellulose Research Studies · Nanocomposite Films for Food Packaging · Electrospun Nanofibers in Biomedical Applications
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (51)
Show source-provided references
1. Horizon 2020 (2014–2015) Food Security, Sustainable Agriculture and Forestry, Marine, Maritime and Inland Water Research and the Bioeconomy, (commission, E., Ed.)
2. Han J (2000) Antimicrobial food packaging. Food Technol 54:56–65
3. Nobile M, Conte A (2013) Bio-based packaging materials for controlled release of active compounds, in packaging for food preservation. Springer, New York
4. Spaic M, Small DP, Cook JR, Wan W (2014) Characterization of anionic and cationic functionalized bacterial cellulose nanofibres for controlled release applications. Cellulose 21:1529–154010.1007/s10570-014-0174-x ↗
5. Lavoine N, Desloges I, Sillard C, Bras J (2014) Controlled release and long-term antibacterial activity of chlorhexidine digluconate through the nanoporous network of microfibrillated cellulose. Cellulose 21:4429–444210.1007/s10570-014-0392-2 ↗
6. Liu K, Chen L, Huang L, Ni Y, Sun B (2015) Enhancing antibacterium and strength of cellulosic paper by coating triclosan-loaded nanofibrillated cellulose (NFC). Carbohydr Polym 117:996–100110.1016/j.carbpol.2014.10.014 ↗
7. Marques HMC (2010) A review on cyclodextrin encapsulation of essential oils and volatiles. Flavour Fragrance J. 25:313–32610.1002/ffj.2019 ↗
8. Zhai F, Li D, Zhang C, Wang X, Li R (2008) Synthesis and characterization of polyoxometalates loaded starch nanocomplex and its antitumoral activity. Eur J Med Chem 43:1911–191710.1016/j.ejmech.2007.11.032 ↗
9. Bober P, Liu J, Mikkonen KS, Ihalainen P, Pesonen M, Plumed-Ferrer C, von Wright A, Lindfors T, Xu C, Latonen R-M (2014) Biocomposites of nanofibrillated cellulose, polypyrrole, and silver nanoparticles with electroconductive and antimicrobial properties. Biomacromolecules 15:3655–366310.1021/bm500939x ↗
10. Ferrocino I, Greppi A, La Storia A, Rantsiou K, Ercolini D, Cocolin L (2016) Impact of nisin-activated packaging on microbiota of beef burgers during storage. Appl Environ Microbiol 82:549–55910.1128/AEM.03093-15 ↗
11. Jebel SF, Almasi H (2016) Morphological, physical, antimicrobial and release properties of ZnO nanoparticles-loaded bacterial cellulose films. Carbohydr Polym 149:8–1910.1016/j.carbpol.2016.04.089 ↗
12. Auxier JA, Schilke KF, McGuire J (2014) Activity retention after nisin entrapment in a polyethylene oxide brush layer. J Food Prot 6:1624–162910.4315/0362-028X.JFP-14-042 ↗
13. Gao C, Yan T, Du J, He F, Luo H, Wan Y (2014) Introduction of broad spectrum antibacterial properties to bacterial cellulose nanofibers via immobilising ε-polylysine nanocoatings. Food Hydrocolloids 36:204–201110.1016/j.foodhyd.2013.09.015 ↗
14. Abdulkhani A, Hosseinzadeh J, Ashori A, Esmaeeli H (2015) Evaluation of the antibacterial activity of cellulose nanofibers/polylactic acid composites coated with ethanolic extract of propolis. Polym Compos10.1002/pc.23554 ↗
15. Mascheroni EG, Guillard V, Gastaldi E, Gontard N, Chalier P (2011) Anti-microbial effectiveness of relative humidity-controlled carvacrol release from wheat gluten/montmorillonite coated papers. Food Control 22:1582–159110.1016/j.foodcont.2011.03.014 ↗
16. Johansson C, Bras J, Mondragon I, Nechita P, Plackett D, Simon P, Svetec DG, Virtanen S, Baschetti MG, Breen C, Clegg F, Aucejo S (2012) Renewable fibers and bio-based materials for packaging applications–a review of recent developments. BioResources 7(2):2506–255210.15376/biores.7.2.2506-2552 ↗
17. Lavoine N, Desloges I, Dufresne A, Bras J (2012) Microfibrillated cellulose - Its barrier properties and applications in cellulosic materials: a review. Carbohydr Polym 90:735–76410.1016/j.carbpol.2012.05.026 ↗
18. Turbak AF, Snyder FW, Sandberg KR (1983) Microfibrillated cellulose, a new cellulose product: properties, uses, and commercial potential. J Appl Polym Sci 37:815–827
19. Syverud K, Stenius P (2009) Strength and barrier properties of MFC films. Cellulose 16:75–8510.1007/s10570-008-9244-2 ↗
20. Siró I, Plackett D (2010) Microfibrillated cellulose and new nanocomposite materials: a review. Cellulose 17:459–49410.1007/s10570-010-9405-y ↗
21. Isogai A, Saito T, Fukuzumi H (2011) TEMPO-oxidized cellulose nanofibers. Nanoscale 3:71–8510.1039/C0NR00583E ↗
22. Saito T, Kimura S, Nishiyama Y, Isogai A (2007) Cellulose nanofibers prepared by TEMPO-mediated oxidation of native cellulose. Biomacromolecules 8:2485–249110.1021/bm0703970 ↗
23. Del Valle EM (2004) Cyclodextrins and their uses: a review. Process Biochem 39:1033–104610.1016/S0032-9592(03)00258-9 ↗
24. Kayaci F, Uyar T (2011) Solid inclusion complexes of vanillin with cyclodextrins: their formation, characterization, and high-temperature stability. J Agric Food Chem 59:11772–1177810.1021/jf202915c ↗
25. Wang J, Cao Y, Sun B, Wang C (2011) Physicochemical and release characterisation of garlic oil-β-cyclodextrin inclusion complexes. Food Chem 127:1680–168510.1016/j.foodchem.2011.02.036 ↗
26. Thayyath SA, Jayachandran N, Peethambaran LD (2015) Synthesis, characterization and in vitro cytotoxicity analysis of a novel cellulose based drug carrier for the controlled delivery of 5-fluorouracil, an anticancer drug. Appl Surf Sci 355:64–7310.1016/j.apsusc.2015.07.077 ↗
27. Lavoine N, Givord C, Tabary N, Desloges I, Martel B, Bras J (2014) Elaboration of a new antibacterial bio-nano-material for food-packaging by synergistic action of cyclodextrin and microfibrillated cellulose. Innov Food Sci Emerg Technol 26:330–34010.1016/j.ifset.2014.06.006 ↗
28. Zhang LZ, Zhou JP, Zhang LN (2013) Structure and properties of β-cyclodextrin/cellulose hydrogels prepared in NaOH/urea aqueous solution. Carbohydr Polym 94:386–39310.1016/j.carbpol.2012.12.077 ↗
29. Lee MH, Yoon KJ, Ko SW (2000) Grafting onto cotton fiber with acryl amidomethylated β-cyclodextrin and its application. J Appl Polym Sci 78:1986–199110.1002/1097-4628(20001209)78:11<1986::AID-APP190>3.0.CO;2-7 ↗
30. Martel B, Weltrowski M, Ruffin D, Morcellet M (2002) Poly carboxylic acids as crosslinking agents for grafting cyclodextrins onto cotton and wool fabrics: study of the process parameters. J Appl Polym Sci 83:1449–145610.1002/app.2306 ↗
31. Chao D, Li-Ying Q, Guang-Lei Z, Bei-Hai H, Hui-Ning X (2014) Preparation of antimicrobial cellulose fibers by grafting β-cyclodextrin and inclusion with antibiotics. Mater Lett 124:181–18310.1016/j.matlet.2014.03.091 ↗
32. Lavoine N, Desloges I, Bras J (2014) Microfibrillated cellulose coatings as new release systems for active packaging. Carbohydr Polym 103:528–53710.1016/j.carbpol.2013.12.035 ↗
33. Arrebola ML, Navarro MC, Jiménez J, Ocaña FA (1994) Yield and composition of the essential oil of Thymus serpylloides subsp. serpylloides. Phytochemistry 36:67–7210.1016/S0031-9422(00)97014-6 ↗
34. Arunasree KM (2010) Anti-proliferative effects of carvacrol on a human metastatic breast cancer cell line, MDA-MB 231. Phytomedicine 17:581–58810.1016/j.phymed.2009.12.008 ↗
35. Liang WZ, Chou CT, Lu T, Chi CC, Tseng LL, Pan CC, Lin KL, Kuo CC, Jan CR (2013) The mechanism of carvacrol-evoked [Ca2+]i rises and non-Ca2+-triggered cell death in OC2 human oral cancer cells. Toxicology 303:152–16110.1016/j.tox.2012.10.026 ↗
36. Hotta M, Nakata R, Katsukawa M, Hori K, Takahashi S, Inoue H (2010) Carvacrol, a component of thyme oil, activates PPARalpha and gamma and suppresses COX-2 expression. J Lipid Res 51:132–13910.1194/jlr.M900255-JLR200 ↗
37. Obaidat MM, Frank JF (2009) Inactivation of Salmonella and Escherichia coli O157:h7 on sliced and whole tomatoes by allyl isothiocyanate, carvacrol, and cinnamaldehyde in vapor phase. J Food Prot 72:315–32410.4315/0362-028X-72.2.315 ↗
38. Upadhyay A, Johny AK, Amalaradjou MA, Ananda BS, Kim KS, Venkitanarayanan K (2012) Plant-derived antimicrobials reduce Listeria monocytogenes virulence factors in vitro, and down-regulate expression of virulence genes. Int J Food Microbiol 15:88–9410.1016/j.ijfoodmicro.2012.04.018 ↗
39. Marcos-Arias C, Eraso E, Madariaga L, Quindós G (2011) In vitro activities of natural products against oral Candida isolates from denture wearers. BMC Complement Altern Med. 11:11910.1186/1472-6882-11-119 ↗
40. El Babili F, Bouajila J, Souchard JP, Bertrand C, Bellvert F, Fouraste I, Moulis C, Valentin A (2011) Oregano: chemical analysis and evaluation of its antimalarial, antioxidant, and cytotoxic activities. J Food Sci 76:512–51810.1111/j.1750-3841.2011.02109.x ↗
41. Karpouhtsis I, Pardali E, Feggou E, Kokkini S, Scouras ZG, Mavragani-Tsipidou P (1998) Insecticidal and genotoxic activities of oregano essential oils. J Agric Food Chem 46:1111–111510.1021/jf970822o ↗
42. US Food and Drug administration. (2014) Food additives permitted for direct addition to food for human consumption, Code of Federal Regulations Title 21 3
43. Council European Parliament (2004) Regulation (EC) no 1935/2004 on materials and articles intended to come into contact with food and repealing Directives 80/590/EEC and 89/109/EEC. Off J Eur Union 338:4–17
44. Orelma H, Filpponen I, Johansson L-S, Osterberg M, Rojas OJ, Laine J (2012) Surface functionalized nanofibrillar cellulose (NFC) film as a platform for immunoassays and diagnostics. Biointerphases 7:6110.1007/s13758-012-0061-7 ↗
45. Cusola O, Tabary N, Bras J (2010) Functionalization of several cellulosic supports for the prolonged release of antibacterial agents. In 13èmes journées du Club Français des Cyclodextrines (POSTER)
46. Cusola O, Tabary N, Belgacem MN, Bras J (2013) Cyclodextrin functionalization of several cellulosic substrates for prolonged release of antibacterial agents. J Appl Polym Sci 129:604–61310.1002/app.38748 ↗
47. Lavoine N, Desloges I, Bras J (2014) Microfibrillated cellulose coatings as new release systems for active packaging. Carbohydr Polym 103:528–53710.1016/j.carbpol.2013.12.035 ↗
48. Missoum K, Bras J, Belgacem M (2012) Organization of aliphatic chains grafted on nanofibrillated cellulose and influence on final properties. Cellulose 19:1957–197310.1007/s10570-012-9780-7 ↗
49. Chalier P, Ben Arfa A, Preziosi-Belloy L, Gontard N (2007) Carvacrol losses from soy protein coated papers as a function of drying conditions. J Appl Polym Sci 106:611–62010.1002/app.26662 ↗
50. Ben Arfa A, Combes S, Preziosi-Belloy L, Gontard N, Chalier P (2006) Antimicrobial activity of carvacrol related to its chemical structure. Lett Appl Microbiol 43:149–15410.1111/j.1472-765X.2006.01938.x ↗
51. Nostro A, Papalia T (2012) Antimicrobial activity of carvacrol: current progress and future prospectives. Recent Pat Anti-Infect Drug Discovery 7:28–3510.2174/157489112799829684 ↗