Abstract
The current demand for new antimicrobial systems has stimulated research for the development of poly(lactic acid)/carvacrol (PLA/CAR)-based materials able to hinder the growth and spread of microorganisms. The eco-friendly characteristics of PLA and cytocompatibility make it very promising in the perspective of green chemistry applications as material for food and biomedical employments. The broad-spectrum biological and pharmacological properties of CAR, including antimicrobial activity, make it an interesting bioactive molecule that can be easily compounded with PLA by adopting the same techniques as those commonly used for PLA manufacturing. This review critically discusses the most common methods to incorporate CAR into a PLA matrix and their interference on the morphomechanical properties, release behavior, and antimicrobial activity of systems. The high potential of PLA/CAR materials in terms of chemical-physical and antimicrobial properties can be exploited for the future development of food packaging, coated medical devices, or drug delivery systems.
Similar content being viewed by others
References
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 Microbiol Infect Dis 30:41–50. https://doi.org/10.1007/s10096-010-1050-8
Altan A, Aytac Z, Uyar T (2018) Carvacrol loaded electrospun fibrous films from zein and poly(lactic acid) for active food packaging. Food Hydrocoll 81:48–59. https://doi.org/10.1016/j.foodhyd.2018.02.028
Andersen A (2006) Final report on the safety assessment of sodium p-chloro-m-cresol, p-chloro-m-cresol, chlorothymol, mixed cresols, m-cresol, o-cresol, p-cresol, isopropyl cresols, thymol, o-cymen-5-ol, and carvacrol. Int J Toxicol 25:29–127. https://doi.org/10.1080/10915810600716653
Armentano I, Fortunati E, Burgos N, Dominici F, Luzi F, Fiori S, Jiménez A, Yoon K, Ahn J, Kang S, Kenny JM (2015) Bio-based PLA_PHB plasticized blend films: processing and structural characterization. LWT Food Sci Technol 64:980–988. https://doi.org/10.1016/j.lwt.2015.06.032
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 43:149–154. https://doi.org/10.1111/j.1472-765X.2006.01938.x
Burgos N, Armentano I, Fortunati E, Dominici F, Luzi F, Fiori S, Cristofaro F, Visai L, Jiménez A, Kenny JM (2017) Functional properties of plasticized bio-based poly(pactic pcid)_poly(hydroxybutyrate) (PLA_PHB) films for active food packaging. Food Bioprocess Technol 10:770–780. https://doi.org/10.1007/s11947-016-1846-3
Burt S (2004) Essential oils: their antibacterial properties and potential applications in foods—a review. Int J Food Microbiol 94:223–253. https://doi.org/10.1016/j.ijfoodmicro.2004.03.022
Celebi H, Gunes E (2018) Combined effect of a plasticizer and carvacrol and thymol on the mechanical, thermal, morphological properties of poly(lactic acid). J Appl Polym Sci 135:45895. https://doi.org/10.1002/app.45895
Chaillot J, Tebbji F, Remmal A, Boone C, Brown GW, Bellaoui M, Sellam A (2015) The monoterpene carvacrol generates endoplasmic reticulum stress in the pathogenic fungus Candida albicans. Antimicrob Agents Chemother 59:4584–4592. https://doi.org/10.1128/AAC.00551-15
Fang S, Zhou Q, Hu Y, Liu F, Mei J, Xie J (2019) Antimicrobial carvacrol incorporated in flaxseed gum-sodium alginate active films to improve the quality attributes of chinese sea bass (Lateolabrax maculatus) during cold storage. Molecules 24:3292. https://doi.org/10.3390/molecules24183292
Frinè V-C, Hector A-P, Manuel N-DS, Estrella N-D, Antonio GJ (2019) Development and characterization of a biodegradable PLA food packaging hold monoterpene-cyclodextrin complexes against Alternaria alternata. Polymers (Basel) 11:1720. https://doi.org/10.3390/polym11101720
Gazzotti S, Todisco SA, Picozzi C, Ortenzi MA, Farina H, Lesma G, Silvani A (2019) Eugenol-grafted aliphatic polyesters: towards inherently antimicrobial PLA-based materials exploiting OCAs chemistry. Eur Polym J 114:369–379. https://doi.org/10.1016/j.eurpolymj.2019.03.001
Herrera N, Salaberria AM, Mathew AP, Oksman K (2016) Plasticized polylactic acid nanocomposite films with cellulose and chitin nanocrystals prepared using extrusion and compression molding with two cooling rates: effects on mechanical, thermal and optical properties. Compos Part A Appl Sci Manuf 83:89–97. https://doi.org/10.1016/j.compositesa.2015.05.024
Inkinen S, Hakkarainen M, Albertsson AC, Södergård A (2011) From lactic acid to poly(lactic acid) (PLA): characterization and analysis of PLA and its precursors. Biomacromolecules 12:523–532. https://doi.org/10.1021/bm101302t
Inouye S, Takizawa T, Yamaguchi H (2001) Antibacterial activity of essential oils and their major constituents against respiratory tract pathogens by gaseous contact. J Antimicrob Chemother 47:565–573. https://doi.org/10.1093/jac/47.5.565
Kachur K, Suntres Z (2019) The antibacterial properties of phenolic isomers, carvacrol and thymol. Crit Rev Food Sci Nutr:1–12. https://doi.org/10.1080/10408398.2019.1675585
Krepker M, Prinz-Setter O, Shemesh R, Vaxman A, Alperstein D, Segal E (2018) Antimicrobial carvacrol-containing polypropylene films: composition, structure and function. Polymers (Basel) 10. https://doi.org/10.3390/polym10010079
Lambert RJW, Skandamis PN, Coote PJ, Nychas G-JE (2001) A study of the minimum inhibitory concentration and mode of action of oregano essential oil, thymol and carvacrol. J Appl Microbiol 91:453–462. https://doi.org/10.1046/j.1365-2672.2001.01428.x
Liu D, Li H, Jiang L, Chuan Y, Yuan M, Chen H (2016) Characterization of active packaging films made from poly(lactic acid)/poly(trimethylene carbonate) incorporated with oregano essential oil. Molecules 21:695. https://doi.org/10.3390/molecules21060695
Lopes MS, Jardini AL, Filho RM (2012) Poly (lactic acid) production for tissue engineering applications. Procedia Eng 42:1402–1413. https://doi.org/10.1016/j.proeng.2012.07.534
Luzi F, Dominici F, Armentano I, Fortunati E, Burgos N, Fiori S, Jiménez A, Kenny JM, Torre L (2019) Combined effect of cellulose nanocrystals, carvacrol and oligomeric lactic acid in PLA_PHB polymeric films. Carbohydr Polym 223:115131. https://doi.org/10.1016/j.carbpol.2019.115131
Maio A, Fucarino R, Khatibi R, Rosselli S, Bruno M, Scaffaro R (2015) A novel approach to prevent graphene oxide re-aggregation during the melt compounding with polymers. Compos Sci Technol 119:131–137. https://doi.org/10.1016/j.compscitech.2015.10.006
Maio A, Giallombardo D, Scaffaro R, Palumbo Piccionello A, Pibiri I (2016) Synthesis of a fluorinated graphene oxide-silica nanohybrid: improving oxygen affinity. RSC Adv 6:46037–46047. https://doi.org/10.1039/c6ra02585d
Maio A, Scaffaro R, Lentini L, Palumbo Piccionello A, Pibiri I (2018) Perfluorocarbons–graphene oxide nanoplatforms as biocompatible oxygen reservoirs. Chem Eng J 334:54–65. https://doi.org/10.1016/j.cej.2017.10.032
Mandras N, Nostro A, Roana J, Scalas D, Banche G, Ghisetti V, Del Re S, Fucale G, Cuffini AM, Tullio V (2016) Liquid and vapour-phase antifungal activities of essential oils against Candida albicans and non-albicans Candida. BMC Complement Altern Med 16:330. https://doi.org/10.1186/s12906-016-1316-5
Marchese A, Arciola CR, Coppo E, Barbieri R, Barreca D, Chebaibi S, Sobarzo-Sánchez E, Nabavi SF, Nabavi SM, Daglia M (2018) The natural plant compound carvacrol as an antimicrobial and anti-biofilm agent: mechanisms, synergies and bio-inspired anti-infective materials. Biofouling 34:630–656. https://doi.org/10.1080/08927014.2018.1480756
Marini E, Di Giulio M, Ginestra G, Magi G, Di Lodovico S, Marino A, Facinelli B, Cellini L, Nostro A (2019) Efficacy of carvacrol against resistant rapidly growing mycobacteria in the planktonic and biofilm growth mode. PLoS One 14. https://doi.org/10.1371/journal.pone.0219038
Martínez-Sanz M, Bilbao-Sainz C, Du W-X, Chiou B-S, Williams TG, Wood DF, Imam SH, Orts WJ, Lopez-Rubio A, Lagaron JM (2015) Antimicrobial poly(lactic acid)-based nanofibres developed by solution blow spinning. J Nanosci Nanotechnol 15:616–627. https://doi.org/10.1166/jnn.2015.9160
Nampoothiri KM, Nair NR, John RP (2010) An overview of the recent developments in polylactide (PLA) research. Bioresour Technol 101:8493–8501. https://doi.org/10.1016/j.biortech.2010.05.092
Nostro A, Papalia T (2012) Antimicrobial activity of carvacrol: current progress and future prospectives. Recent Pat Antiinfect Drug Discov 7:28–35. https://doi.org/10.2174/157489112799829684
Nostro A, Blanco AR, Cannatelli MA, Enea V, Flamini G, Morelli I, Roccaro AS, Alonzo V (2004) Susceptibility of methicillin-resistant staphylococci to oregano essential oil, carvacrol and thymol. FEMS Microbiol Lett 230:191–195. https://doi.org/10.1016/S0378-1097(03)00890-5
Nostro A, Roccaro AS, Bisignano G, Marino A, Cannatelli MA, Pizzimenti FC, Cioni PL, Procopio F, Blanco AR (2007) Effects of oregano, carvacrol and thymol on Staphylococcus aureus and Staphylococcus epidermidis biofilms. J Med Microbiol 56:519–523. https://doi.org/10.1099/jmm.0.46804-0
Nostro A, Marino A, Blanco AR, Cellini L, Di Giulio M, Pizzimenti F, Roccaro AS, Bisignano G (2009) In vitro activity of carvacrol against staphylococcal preformed biofilm by liquid and vapour contact. J Med Microbiol 58:791–797. https://doi.org/10.1099/jmm.0.009274-0
Nostro A, Scaffaro R, Ginestra G, D’Arrigo M, Botta L, Marino A, Bisignano G (2010) Control of biofilm formation by poly-ethylene-co-vinyl acetate films incorporating nisin. Appl Microbiol Biotechnol 87:729–737. https://doi.org/10.1007/s00253-010-2598-z
Nostro A, Scaffaro R, D’Arrigo M, Botta L, Filocamo A, Marino A, Bisignano G (2012) Study on carvacrol and cinnamaldehyde polymeric films: mechanical properties, release kinetics and antibacterial and antibiofilm activities. Appl Microbiol Biotechnol 96:1029–1038. https://doi.org/10.1007/s00253-012-4091-3
Nostro A, Scaffaro R, Botta L, Filocamo A, Marino A, Bisignano G (2015) Effect of temperature on the release of carvacrol and cinnamaldehyde incorporated into polymeric systems to control growth and biofilms of Escherichia coli and Staphylococcus aureus. Biofouling 31:639–649. https://doi.org/10.1080/08927014.2015.1079703
Persico P, Ambrogi V, Carfagna C, Cerruti P, Ferrocino I, Mauriello G (2009) Nanocomposite polymer films containing carvacrol for antimicrobial active packaging. Polym Eng Sci 49:1447–1455. https://doi.org/10.1002/pen.21191
Raouche S, Mauricio-Iglesias M, Peyron S, Guillard V, Gontard N (2011) Combined effect of high pressure treatment and anti-microbial bio-sourced materials on microorganisms’ growth in model food during storage. Innov Food Sci Emerg Technol 12:426–434. https://doi.org/10.1016/j.ifset.2011.06.012
Rasal RM, Janorkar AV, Hirt DE (2010) Poly(lactic acid) modifications. Prog Polym Sci 35:338–356. https://doi.org/10.1016/j.progpolymsci.2009.12.003
Requena R, Vargas M, Chiralt A (2018) Obtaining antimicrobial bilayer starch and polyester-blend films with carvacrol. Food Hydrocoll 83:118–133. https://doi.org/10.1016/j.foodhyd.2018.04.045
Scaffaro R, Lopresti F (2018) Processing, structure, property relationships and release kinetics of electrospun PLA/carvacrol membranes. Eur Polym J 100C:165–171. https://doi.org/10.1016/j.eurpolymj.2018.01.035
Scaffaro R, Maio A (2017) A green method to prepare nanosilica modified graphene oxide to inhibit nanoparticles re-aggregation during melt processing. Chem Eng J 308:1034–1037. https://doi.org/10.1016/j.cej.2016.09.131
Scaffaro R, Maio A (2019a) Optimization of two-step techniques engineered for the preparation of polyamide 6 graphene oxide nanocomposites. Compos Part B Eng 165:55–64. https://doi.org/10.1016/j.compositesb.2018.11.107
Scaffaro R, Maio A (2019b) Integrated ternary bionanocomposites with superior mechanical performance via the synergistic role of graphene and plasma treated carbon nanotubes. Compos Part B Eng 168:550–559. https://doi.org/10.1016/j.compositesb.2019.03.076
Scaffaro R, Botta L, Lopresti F, Maio A, Sutera F (2016) Polysaccharide nanocrystals as fillers for PLA based nanocomposites. Cellulose. 24:447–478. https://doi.org/10.1007/s10570-016-1143-3
Scaffaro R, Botta L, Maio A, Gallo G (2017a) PLA graphene nanoplatelets nanocomposites: physical properties and release kinetics of an antimicrobial agent. Compos Part B Eng 109:138–146. https://doi.org/10.1016/j.compositesb.2016.10.058
Scaffaro R, Lopresti F, Maio A, Sutera F, Botta L (2017b) Development of polymeric functionally graded scaffold: a brief review. J Appl Biomater Funct Mater 15:107–121. https://doi.org/10.5301/jabfm.5000332
Scaffaro R, Lopresti F, Sutera A, Botta L, Fontana RM, Gallo G (2017c) Plasma modified PLA electrospun membranes for actinorhodin production intensification in Streptomyces coelicolor A3(2) immobilized-cell cultivations. Colloids Surf B: Biointerfaces 157:233–241. https://doi.org/10.1016/j.colsurfb.2017.05.060
Scaffaro R, Gulino FE, Lopresti F (2018a) Structure–property relationship and controlled drug release from multiphasic electrospun carvacrol-embedded polylactic acid/polyethylene glycol and polylactic acid/polyethylene oxide nanofiber mats. J Ind Text. https://doi.org/10.1177/1528083718801359
Scaffaro R, Lopresti F, D’Arrigo M, Marino A, Nostro A (2018b) Efficacy of poly(lactic acid)/carvacrol electrospun membranes against Staphylococcus aureus and Candida albicans in single and mixed cultures. Appl Microbiol Biotechnol 102:4171–4181. https://doi.org/10.1007/s00253-018-8879-7
Scaffaro R, Lopresti F, Marino A, Nostro A (2018c) Antimicrobial additives for poly(lactic acid) materials and their applications: current state and perspectives. Appl Microbiol Biotechnol 102:7739–7756. https://doi.org/10.1007/s00253-018-9220-1
Scaffaro R, Maio A, Lo Re G, Parisi A, Busacca A (2018d) Advanced piezoresistive sensor achieved by amphiphilic nanointerfaces of graphene oxide and biodegradable polymer blends. Compos Sci Technol 156:166–176. https://doi.org/10.1016/j.compscitech.2018.01.008
Scaffaro R, Sutera F, Botta L (2018f) Biopolymeric bilayer films produced by co-extrusion film blowing. Polym Test 65:35–43. https://doi.org/10.1016/j.polymertesting.2017.11.010
Scaffaro R, Maio A, Botta L, Gulino EF, Gulli D (2019a) Tunable release of chlorhexidine from polycaprolactone-based filaments containing graphene nanoplatelets. Eur Polym J 110:221–232. https://doi.org/10.1016/j.eurpolymj.2018.11.031
Scaffaro R, Maio A, Lopresti F (2019b) Effect of graphene and fabrication technique on the release kinetics of carvacrol from polylactic acid. Compos Sci Technol 169:60–69. https://doi.org/10.1016/j.compscitech.2018.11.003
Scaffaro R, Maio A, Sutera F, Gulino EF, Morreale M (2019c) Degradation and recycling of films based on biodegradable polymers: a short review. Polymers (Basel):11. https://doi.org/10.3390/polym11040651
Sharifi-Rad M, Varoni EM, Iriti M, Martorell M, Setzer WN, del Mar CM, Salehi B, Soltani-Nejad A, Rajabi S, Tajbakhsh M, Sharifi-Rad J (2018) Carvacrol and human health: a comprehensive review. Phyther Res 32:1675–1687. https://doi.org/10.1002/ptr.6103
Suntres ZE, Coccimiglio J, Alipour M (2015) The bioactivity and toxicological actions of carvacrol. Crit Rev Food Sci Nutr 55:304–318. https://doi.org/10.1080/10408398.2011.653458
Tawakkal ISMA, Cran MJ, Miltz J, Bigger SW (2014) A review of poly(lactic acid)-based materials for antimicrobial packaging. J Food Sci 79:R1477–R1490. https://doi.org/10.1111/1750-3841.12534
Van de Velde K, Kiekens P (2002) Biopolymers: overview of several properties and consequences on their applications. Polym Test 21:433–442. https://doi.org/10.1016/S0142-9418(01)00107-6
Yang C, Tang H, Wang Y, Liu Y, Wang J, Shi W, Li L (2019) Development of PLA-PBSA based biodegradable active film and its application to salmon slices. Food Packag Shelf Life 22:100393. https://doi.org/10.1016/j.fpsl.2019.100393
Zodrow KR, Schiffman JD, Elimelech M (2012) Biodegradable polymer (PLGA) coatings featuring cinnamaldehyde and carvacrol mitigate biofilm formation. Langmuir 28:13993–13999. https://doi.org/10.1021/la303286v
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
This article does not contain any studies with human participants or animals performed by any of the authors.
Conflict of interest
The authors declare that they have no conflict of interest.
Additional information
Publisher’s note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Scaffaro, R., Maio, A. & Nostro, A. Poly(lactic acid)/carvacrol-based materials: preparation, physicochemical properties, and antimicrobial activity. Appl Microbiol Biotechnol 104, 1823–1835 (2020). https://doi.org/10.1007/s00253-019-10337-9
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00253-019-10337-9