Synthesis, characterization and antibacterial activity of thymol-loaded polylactic acid microparticles entrapped with essential oils of varying viscosity
Source abstract
Abstract
Double emulsion technique (W1/O/W2) was used to achieve PLA (polylactic acid)-based microparticles loaded with thymol (hydrophilic antibacterial active) with high encapsulation efficiency (> 90%) that was later released in water in controlled fashion. In order to enhance the release of thymol from semicrystalline slow degrading PLA matrix, pores were introduced into the particles by incorporating minute quantity of essential oils (EOs) such as castor, mustard, olive and coconut oils of varying viscosity (from 128 to 13 mPa S). Strikingly, it was found that the pore size of microparticles (pore size 1.2–0.53 µm and specific surface area 7.5–2.1 m2/g) has been influenced by the viscosity of EOs. The plausible mechanism of formation of pores using EOs was also explored. As expected, the release rate of thymol did get accelerate with the increase in pore density and its release mechanism can well be explained with the help of power law model. In addition to that, these porous particles were demonstrated to act as an effective carrier for continuous delivery of thymol with enhanced inhibitory activity probably due to synergistic action of EOs and thymol. Therefore, EOs employed here served dual purposes. These PLA-based microparticles composed of completely natural ingredients can be exploited as active food packaging material to prolong the shelf life of food.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Nanocomposite Films for Food Packaging · biodegradable polymer synthesis and properties · Advanced Drug Delivery Systems
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (62)
Show source-provided references
1. Tajkarimi MM, Ibrahim SA, Cliver DO (2010) Antimicrobial herb and spice compounds in food. Food Control 21(9):1199–121810.1016/j.foodcont.2010.02.003 ↗
2. Cammack R, Joannou CL, Cui X-Y, Torres Martinez C, Maraj SR, Hughes MN (1999) Nitrite and nitrosyl compounds in food preservation. Biochim Biophys Acta Bioenerg 1411(2):475–48810.1016/S0005-2728(99)00033-X ↗
3. Abdulmumeen HA, Risikat AN, Sururah AR (2012) Food: its preservatives, additives and applications. Int J Chem Biochem Sci 1:36–47
4. LaCoste A, Schaich KM, Zumbrunnen D, Yam KL (2005) Advancing controlled release packaging through smart blending. Packag Technol Sci 18(2):77–8710.1002/pts.675 ↗
5. Appendini P, Hotchkiss JH (2002) Review of antimicrobial food packaging. Innov Food Sci Emerg Technol 3(2):113–12610.1016/S1466-8564(02)00012-7 ↗
6. Wyrwa J, Barska A (2017) Innovations in the food packaging market: active packaging. Eur Food Res Technol 243(10):1681–169210.1007/s00217-017-2878-2 ↗
7. Chung Donghwan, Chikindas Michael L, Yam KL (2001) Inhibition of Saccharomyces cerevisiae by slow release of propyl paraben from a polymer coating. J Food Protect 64(9):1420–142410.4315/0362-028X-64.9.1420 ↗
8. Ha JU, Kim YM, Lee DS (2001) Multilayered antimicrobial polyethylene films applied to the packaging of ground beef. Packag Technol Sci 14(2):55–6210.1002/pts.537 ↗
9. Sharma GK, Madhura CV, Arya SS (1990) Interaction of plastic films with foods. II. Effect of polyethylene and polypropylene films on the stability of vegetable Oils. J Food Sci Technol 27:327–331
10. Scarfato P, Avallone E, Galdi MR, Di Maio L, Incarnato L (2017) Preparation, characterization, and oxygen scavenging capacity of biodegradable α-tocopherol/PLA microparticles for active food packaging applications. Polym Compos 38(5):981–98610.1002/pc.23661 ↗
11. Biswal AK, Usmani M, Ahammad SZ, Saha S (2018) Unveiling the slow release behavior of hollow particles with prolonged antibacterial activity. J Mater Sci 53(8):5942–5957. https://doi.org/10.1007/s10853-018-1991-310.1007/s10853-018-1991-3 ↗
12. Pawar PA, Aachal HP (2013) Biodegradable polymers in food packaging. Am J Eng Res 2(5):151–164
13. Atarés L, Chiralt A (2016) Essential oils as additives in biodegradable films and coatings for active food packaging. Trend Food Sci Technol 48:51–6210.1016/j.tifs.2015.12.001 ↗
14. Braga PC, Culici M, Alfieri M, Dal Sasso M (2008) Thymol inhibits Candida albicans biofilm formation and mature biofilm. Int J Antimicrob Agents 31(5):472–47710.1016/j.ijantimicag.2007.12.013 ↗
15. Alves-Silva JM, Dias dos Santos SM, Pintado ME, Pérez-Álvarez JA, Fernández-López J, Viuda-Martos M (2013) Chemical composition and in vitro antimicrobial, antifungal and antioxidant properties of essential oils obtained from some herbs widely used in Portugal. Food Control 32(2):371–37810.1016/j.foodcont.2012.12.022 ↗
16. Galotto MJ, de Dicastillo CL, Torres A, Guarda A (2016) Chapter 45—thymol: use in antimicrobial packaging A2—Barros-Velázquez, Jorge. Antimicrobial food packaging. Academic Press, San Diego, pp 553–56210.1016/B978-0-12-800723-5.00045-0 ↗
17. Ahmad A, Khan A, Akhtar F, Yousuf S, Xess I, Khan LA, Manzoor N (2011) Fungicidal activity of thymol and carvacrol by disrupting ergosterol biosynthesis and membrane integrity against Candida. Eur J Clin Microb Infect Dis 30(1):41–5010.1007/s10096-010-1050-8 ↗
18. Martins IM, Rodrigues SN, Barreiro MF, Rodrigues AE (2012) Release studies of thymol and p-cymene from polylactide microcapsules. Ind Eng Chem Res 51(35):11565–1157110.1021/ie301406f ↗
19. Lin K-H, Yeh S-Y, Lin M-Y, Shih M-C, Yang K-Tu, Hwang S-Y (2007) Major chemotypes and antioxidative activity of the leaf essential oils of Cinnamomum osmophloeum Kaneh. from a clonal orchard. Food Chem 105(1):133–13910.1016/j.foodchem.2007.03.051 ↗
20. Rowsni Asma Afroz, Islam Kamrul, Khan MM, Kabir MS (2014) Antimicrobial activity of essential oils against food-borne pathogenic bacteria. Int J Pharm Sci Res 32(5):4876–4879
21. Siddiqui Nazima, Ahmad Adeel (2013) A study on viscosity, surface tension and volume flow rate of some edible and medicinal oils. Int J Sci Environ Technol 2(6):1318–1326
22. Wu J, Liu H, Ge S, Wang S, Qin Z, Chen L, Zheng Q, Liu Q, Zhang Q (2015) The preparation, characterization, antimicrobial stability and in vitro release evaluation of fish gelatin films incorporated with cinnamon essential oil nanoliposomes. Food Hydrocolloids 43(Supplement C):427–43510.1016/j.foodhyd.2014.06.017 ↗
23. Biswal A.K., Usmani M., Ahammad S.Z., S. S (2017) Synergistic combinations of natural antimicrobials encapsulated in the porous PLGA particles and their application in food preservation. India Patent Application no. 201711035034
24. Moussaoui F, Alaoui T (2016) Evaluation of antibacterial activity and synergistic effect between antibiotic and the essential oils of some medicinal plants. Asian Pac J Trop Biomed 6(1):32–3710.1016/j.apjtb.2015.09.024 ↗
25. Liu S, Cai M, Deng R, Wang J, Liang R, Zhu J (2014) Fabrication of porous polymer microparticles with tunable pore size and density through the combination of phase separation and emulsion-solvent evaporation approach. Kor Aust Rheol J 26(1):63–7110.1007/s13367-014-0007-3 ↗
26. Crotts G, Park TG (1995) Preparation of porous and nonporous biodegradable polymeric hollow microspheres. J Control Release 35(2):91–10510.1016/0168-3659(95)00010-6 ↗
27. It was observed that PLA was not soluble in any of the essential oils because there was no change of PLA when it was placed in EOs
28. Batista MM, Guirardello R, Krähenbühl MA (2013) Determination of the solubility parameters of biodiesel from vegetable oils. Energy Fuels 27(12):7497–750910.1021/ef401690f ↗
29. Lee WL, Wee P, Nugraha C, Loo SCJ (2013) Gastric-floating microcapsules provide controlled and sustained release of multiple cardiovascular drugs. J Mater Chem B 1(8):1090–109510.1039/C2TB00495J ↗
30. Udoh CE, Garbin V, Cabral JT (2016) Microporous polymer particles via phase inversion in microfluidics: impact of nonsolvent quality. Langmuir 32(32):8131–814010.1021/acs.langmuir.6b01799 ↗
31. Dubinsky S, Park JI, Gourevich I, Chan C, Deetz M, Kumacheva E (2009) Toward controlling the surface morphology of macroporous copolymer particles. Macromolecules 42(6):1990–199410.1021/ma802813v ↗
32. Kim MR, Lee S, Park J-K, Cho KY (2010) Golf ball-shaped PLGA microparticles with internal pores fabricated by simple O/W emulsion. Chem Commun 46(39):7433–743510.1039/c0cc01738h ↗
33. Mao S, Shi Y, Li L, Xu J, Schaper A, Kissel T (2008) Effects of process and formulation parameters on characteristics and internal morphology of poly(d, l-lactide-co-glycolide) microspheres formed by the solvent evaporation method. Eur J Pharm Biopharm 68(2):214–22310.1016/j.ejpb.2007.06.008 ↗
34. Shi X, Sun L, Jiang J, Zhang X, Ding W, Gan Z (2009) Biodegradable polymeric microcarriers with controllable porous structure for tissue engineering. Macromol Biosci 9(12):1211–121810.1002/mabi.200900224 ↗
35. Del Nobile MA, Conte A, Incoronato AL, Panza O (2008) Antimicrobial efficacy and release kinetics of thymol from zein films. J Food Eng 89(1):57–6310.1016/j.jfoodeng.2008.04.004 ↗
36. Cosentino S, Tuberoso CIG, Pisano B, Satta M, Mascia V, Arzedi E, Palmas F (1999) In-vitro antimicrobial activity and chemical composition of Sardinian Thymus essential oils. Lett Appl Microbiol 29(2):130–135. https://doi.org/10.1046/j.1472-765X.1999.00605.x10.1046/j.1472-765X.1999.00605.x ↗
37. Pilati F, Degli Esposti M, Bondi M, Iseppi R, Toselli M (2013) Designing of antibacterial plastics: thymol release from photocured thymol-doped acrylic resins. J Mater Sci 48(12):4378–4386. https://doi.org/10.1007/s10853-013-7253-510.1007/s10853-013-7253-5 ↗
38. Surnar B, Jayakannan M (2013) Stimuli-responsive poly(caprolactone) vesicles for dual drug delivery under the gastrointestinal tract. Biomacromolecules 14(12):4377–438710.1021/bm401323x ↗
39. Siepmann J, Peppas NA (2001) Modeling of drug release from delivery systems based on hydroxypropyl methylcellulose (HPMC). Adv Drug Deliv Rev 48(2):139–15710.1016/S0169-409X(01)00112-0 ↗
40. Sanson C, Schatz C, Le Meins J-F, Soum A, Thévenot J, Garanger E, Lecommandoux S (2010) A simple method to achieve high doxorubicin loading in biodegradable polymersomes. J Control Release 147(3):428–43510.1016/j.jconrel.2010.07.123 ↗
41. Lu L, Peter SJ, Lyman MD, Lai HL, Leite SM, Tamada JA, Vacanti JP, Langer R, Mikos AG (2000) In vitro degradation of porous poly(L-lactic acid) foams. Biomaterials 21(15):1595–160510.1016/S0142-9612(00)00048-X ↗
42. Liu D, Li H, Zhou G, Yuan M, Qin Y (2015) Biodegradable poly(lactic-acid)/poly(trimethylene-carbonate)/laponite composite film: development and application to the packaging of mushrooms (Agaricus bisporus). Polym Adv Technol 26(12):1600–160710.1002/pat.3587 ↗
43. Dasmahapatra AK, Nanavati H, Kumaraswamy G (2009) Polymer crystallization in the presence of “sticky” additives. J Chem Phys 131(7):074905-1–074905-1010.1063/1.3174449 ↗
44. Dong Y, Feng S-S (2007) In vitro and in vivo evaluation of methoxy polyethylene glycol–polylactide (MPEG–PLA) nanoparticles for small-molecule drug chemotherapy. Biomaterials 28(28):4154–416010.1016/j.biomaterials.2007.05.026 ↗
45. Mistry P, Mohapatra S, Gopinath T, Vogt FG, Suryanarayanan R (2015) Role of the strength of drug-polymer interactions on the molecular mobility and crystallization inhibition in ketoconazole solid dispersions. Mol Pharm 12(9):3339–335010.1021/acs.molpharmaceut.5b00333 ↗
46. Lin Y, Zhang K-Y, Dong Z-M, Dong L-S, Li Y-S (2007) Study of hydrogen-bonded blend of polylactide with biodegradable hyperbranched poly(ester amide). Macromolecules 40(17):6257–626710.1021/ma070989a ↗
47. Kumar Singla R, Maiti SN, Ghosh AK (2016) Fabrication of super tough poly(lactic acid)/ethylene-co-vinyl-acetate blends via a melt recirculation approach: static-short term mechanical and morphological interpretation. RSC Adv 6(18):14580–1458810.1039/C5RA24897C ↗
48. Chadha R, Kapoor VK, Kumar A (2006) Analytical techniques used to characterize drug–polyvinyl-pyrrolidone systems in solid and liquid states: an overview. J Sci Industr Res 65:459–469
49. Coughlan DC, Corrigan OI (2006) Drug–polymer interactions and their effect on thermoresponsive poly(N-isopropylacrylamide) drug delivery systems. Int J Pharm 313(1):163–17410.1016/j.ijpharm.2006.02.005 ↗
50. Lambert RJW, Skandamis PN, Coote PJ, Nychas GJE (2001) A study of the minimum inhibitory concentration and mode of action of oregano essential oil, thymol and carvacrol. J Appl Microbiol 91(3):453–46210.1046/j.1365-2672.2001.01428.x ↗
51. Friedman Mendel, Henika Philip R, Mandrell RE (2002) Bactericidal Activities of Plant Essential Oils and Some of Their Isolated Constituents against Campylobacter jejuni, Escherichia coli, Listeria monocytogenes, and Salmonella enterica. J Food Protect 65(10):1545–156010.4315/0362-028X-65.10.1545 ↗
52. Falcone PM, Mastromatteo M, Nobile MAD, Corbo MR, Sinigaglia M (2007) Evaluating in vitro antimicrobial activity of thymol toward hygiene-indicating and pathogenic bacteria. J Food Protect 70(2):425–43110.4315/0362-028X-70.2.425 ↗
53. Hyldgaard M, Mygind T, Meyer R (2012) Essential oils in food preservation: mode of action, synergies, and interactions with food matrix components. Front Microbiol 3(12):1–12
54. Kubo A, Lunde CS, Kubo I (1995) Antimicrobial activity of the olive oil flavor compounds. J Agric Food Chem 43(6):1629–163310.1021/jf00054a040 ↗
55. Janakat S, Al-Nabulsi AAR, Allehdan S, Olaimat AN, Holley RA (2015) Antimicrobial activity of amurca (olive oil lees) extract against selected foodborne pathogens. Food Sci Technol 35:259–26510.1590/1678-457X.6508 ↗
56. Pereira JA, Pereira APG, Ferreira ICFR, Valentão P, Andrade PB, Seabra R, Estevinho L, Bento A (2006) Table olives from Portugal: phenolic compounds, antioxidant potential, and antimicrobial activity. J Agric Food Chem 54(22):8425–843110.1021/jf061769j ↗
57. Shofran BG, Purrington ST, Breidt F, Fleming HP (1998) Antimicrobial properties of sinigrin and its hydrolysis products. J Food Sci 63(4):621–62410.1111/j.1365-2621.1998.tb15798.x ↗
58. Turgis M, Han J, Caillet S, Lacroix M (2009) Antimicrobial activity of mustard essential oil against Escherichia coli O157:H7 and Salmonella typhi. Food Control 20(12):1073–107910.1016/j.foodcont.2009.02.001 ↗
59. Wilson R, van Schie BJ, Howes D (1998) Overview of the preparation, use and biological studies on polyglycerol polyricinoleate (PGPR). Food Chem Toxicol 36(9):711–71810.1016/S0278-6915(98)00057-X ↗
60. Abbaspourrad A, Carroll NJ, Kim S-H, Weitz DA (2013) Surface functionalized hydrophobic porous particles toward water treatment application. Adv Mater 25(23):3215–322110.1002/adma.201300656 ↗
61. Al-Mamun MA, Akter Z, Uddin MJ, Ferdaus KMKB, Hoque KMF, Ferdousi Z, Reza MA (2016) Characterization and evaluation of antibacterial and antiproliferative activities of crude protein extracts isolated from the seed of Ricinus communis in Bangladesh. BMC Complement Altern Med 16(1):211-1–211-10
62. Ogbolu DO, Oni AA, Daini OA, Oloko AP (2007) In vitro antimicrobial properties of coconut oil on Candida Species in Ibadan, Nigeria. J Med Food 10(2):384–38710.1089/jmf.2006.1209 ↗