Abstract
Biodegradable materials have attracted considerable attention to be applied in maintaining food quality and safety due to their ability of a sustained release of antimicrobial agents. In this study, cinnamon essential oil (CEO) loaded poly (ethylene glycol)-poly (ε-caprolactone) (PEG-PCL) micelles (CEO-micelles) were prepared for humidity-controlled CEO release and preservation of strawberry quality. The CEO-micelles with spherical shape and uniform size were obtained, and a high encapsulation rate (92.00 ± 1.77%) of CEO was achieved. X-ray diffraction demonstrated that the CEO was successfully encapsulated in PEG-PCL micelles. The release rate could be controlled by adjusting the relative humidity (RH) and 75% RH was favorable for CEO release from micelles (with 72% total amount release in 7 days). The encapsulation of CEO with high concentrations in PEG-PCL micelles reduced the cytotoxicity. Additionally, CEO-micelles exhibited high antifungal activity against Botrytis cinerea, the main pathogenic fungus of strawberry. Finally, the application of CEO-micelles to the preservation of strawberries had a positive effect on changes in decay rate, weight loss, firmness, color, and total soluble solids. These findings suggested that the CEO-micelles could be fabricated to humidity responsible nano-vesicles for preservation of fruit or vegetable with controllable release profile.
Similar content being viewed by others
Data Availability
All data generated or analyzed during this study are included in this published article and supplementary information files.
Abbreviations
- CEO-micelles:
-
Cinnamon essential oil loaded poly (ethylene glycol)-poly (ε-caprolactone) micelles
- EOs:
-
Essential oils
- CEO:
-
Cinnamon essential oil
- PEG-PCL:
-
Poly (ethylene glycol)-poly (ε-caprolactone)
- PEG:
-
Polyethylene glycol
- PCL:
-
Poly (ε-caprolactone)
- CCK-8:
-
Cell Counting Kit-8
- blank-micelles:
-
The micelles without CEO
- PDI:
-
Polydispersity index
- DLS:
-
Dynamic laser light scattering
- TEM:
-
Transmission electron microscopy
- XRD:
-
X-ray diffractometer
- EE%:
-
The encapsulation efficiency percentage
- HPLC:
-
High-performance liquid chromatography
- PDA:
-
Potato dextrose agar
- ITS:
-
Internal transcribed spacer
- N-J:
-
Neighbor-joining methods
- PET:
-
Polyethylene terephthalate
- CK:
-
Control
- CEO-2:
-
The ratio of CEO content to the volume of air in the clamshells (0.6 L) was 2 μL/L
- CEO-5:
-
The ratio of CEO content to the volume of air in the clamshells (0.6 L) was 5 μL/L
- CEO-10:
-
The ratio of CEO content to the volume of air in the clamshells (0.6 L) was 10 μL/L
- CEO-micelles-2:
-
CEO-micelles with the same amount of CEO as the CEO-2 treatment group
- CEO-micelles-5:
-
CEO-micelles with the same amount of CEO as the CEO-5 treatment group
- CEO-micelles-10:
-
CEO-micelles with the same amount of CEO as the CEO-10 treatment group
- TSS:
-
Total soluble solids
References
Akhavan, H. -R., Hosseini, F. -S., Amiri, S., & Radi, M. (2021). Cinnamaldehyde-loaded nanostructured lipid carriers extend the shelf life of date palm fruit. Food and Bioprocess Technology, 14(8), 1478–1489. https://doi.org/10.1007/s11947-021-02645-8
Alikhani, M., & Daraei Garmakhany, A. (2012). Effect of microencapsulated essential oils on storage life and quality of strawberry (Fragaria ananassa cv. Camarosa). Quality Assurance and Safety of Crops & Foods, 4(2), 106–112. https://doi.org/10.1111/j.1757-837X.2012.00128.x
Azouz, L., Dahmoune, F., Rezgui, F., & G’Sell, C. (2016). Full factorial design optimization of anti-inflammatory drug release by PCL-PEG-PCL microspheres. Materials Science & Engineering, C: Materials for Biological Applications, 58, 412–419. https://doi.org/10.1016/j.msec.2015.08.058
Bahrami, A., Delshadi, R., Assadpour, E., Jafari, S. M., & Williams, L. (2020). Antimicrobial-loaded nanocarriers for food packaging applications. Advances in Colloid and Interface Science, 278, 102140. https://doi.org/10.1016/j.cis.2020.102140
Balaguer, M. P., Borne, M., Chalier, P., Gontard, N., Morel, M. H., Peyron, S., Gavara, R., & Hernandez-Munoz, P. (2013). Retention and release of cinnamaldehyde from wheat protein matrices. Biomacromolecules, 14(5), 1493–1502. https://doi.org/10.1021/bm400158t
Behl, A., Parmar, V. S., Malhotra, S., & Chhillar, A. K. (2020). Biodegradable diblock copolymeric PEG-PCL nanoparticles: Synthesis, characterization and applications as anticancer drug delivery agents. Polymer. https://doi.org/10.1016/j.polymer.2020.122901
Chaudhari, A. K., Singh, V. K., Das, S., Deepika, Singh, B. K., & Dubey, N. K. (2020). Antimicrobial, aflatoxin b1 inhibitory and lipid oxidation suppressing potential of anethole-based chitosan nanoemulsion as novel preservative for protection of stored maize. Food and Bioprocess Technology, 13(8), 1462–1477. https://doi.org/10.1007/s11947-020-02479-w
Chu, Y., Gao, C., Liu, X., Zhang, N., Xu, T., Feng, X., Yang, Y., Shen, X., & Tang, X. (2020). Improvement of storage quality of strawberries by pullulan coatings incorporated with cinnamon essential oil nanoemulsion. Lwt. https://doi.org/10.1016/j.lwt.2020.109054
Clemente, I., Aznar, M., Silva, F., & Nerín, C. (2016). Antimicrobial properties and mode of action of mustard and cinnamon essential oils and their combination against foodborne bacteria. Innovative Food Science & Emerging Technologies, 36, 26–33. https://doi.org/10.1016/j.ifset.2016.05.013
Danafar, H., Davaran, S., Rostamizadeh, K., Valizadeh, H., & Hamidi, M. (2014). Biodegradable m-PEG/PCL core-shell micelles: Preparation and characterization as a sustained release formulation for curcumin. Advanced Pharmaceutical Bulletin, 4, 501–510. https://doi.org/10.1016/j.ijpharm.2020.119340
Das, S., Singh, V. K., Dwivedy, A. K., Chaudhari, A. K., & Dubey, N. K. (2021). Anethum graveolens essential oil encapsulation in chitosan nanomatrix: Investigations on in vitro release behavior, organoleptic attributes, and efficacy as potential delivery vehicles against biodeterioration of rice (Oryza sativa L.). Food and Bioprocess Technology, 14(5), 831–853. https://doi.org/10.1007/s11947-021-02589-z
Del Toro-Sánchez, C. L., Ayala-Zavala, J. F., Machi, L., Santacruz, H., Villegas-Ochoa, M. A., Alvarez-Parrilla, E., & González-Aguilar, G. A. (2010). Controlled release of antifungal volatiles of thyme essential oil from β-cyclodextrin capsules. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 67(3–4), 431–441. https://doi.org/10.1007/s10847-009-9726-3
Göktepe, S., Ocak, B., & Özdestan-Ocak, Ö. (2021). Physico-chemical, sensory, and antioxidant characteristics of olive paste enriched with microencapsulated thyme essential oil. Food and Bioprocess Technology, 14(11), 2032–2045. https://doi.org/10.1007/s11947-021-02707-x
Granata, G., Stracquadanio, S., Leonardi, M., Napoli, E., Consoli, G. M. L., Cafiso, V., Stefani, S., & Geraci, C. (2018). Essential oils encapsulated in polymer-based nanocapsules as potential candidates for application in food preservation. Food Chemistry, 269, 286–292. https://doi.org/10.1016/j.foodchem.2018.06.140
Hemmatkhah, F., Zeynali, F., & Almasi, H. (2020). Encapsulated cumin seed essential oil-loaded active papers: Characterization and evaluation of the effect on quality attributes of beef hamburger. Food and Bioprocess Technology, 13(3), 533–547. https://doi.org/10.1007/s11947-020-02418-9
Kamaruzzaman, M., Hao, F., Wu, M., & Li, G. (2018). Gray mold of strawberry (Fragaria ananassa) caused by a rare pink-colored isolate of Botrytis cinerea in China. Australasian Plant Pathology, 47(6), 587–589. https://doi.org/10.1007/s13313-018-0593-5
Kujur, A., Kumar, A., Singh, P. P., & Prakash, B. (2021). Fabrication, characterization, and antifungal assessment of jasmine essential oil-loaded chitosan nanomatrix against Aspergillus flavus in food system. Food and Bioprocess Technology, 14(3), 554–571. https://doi.org/10.1007/s11947-021-02592-4
Lee, J. S., Choi, I., & Han, J. (2021). Mathematical modeling of cinnamon (Cinnamomum verum) bark oil release from agar/PVA biocomposite film for antimicrobial food packaging: The effects of temperature and relative humidity. Food Chemistry, 363, 130306. https://doi.org/10.1016/j.foodchem.2021.130306
Lin, Y., Huang, R., Sun, X., Yu, X., Xiao, Y., Wang, L., Hu, W., & Zhong, T. (2021). The p-anisaldehyde/β-cyclodextrin inclusion complexes as fumigation agent for control of postharvest decay and quality of strawberry. Food Control. https://doi.org/10.1016/j.foodcont.2021.108346
Liu, L., Wang, P., Qu, C., Wei, Z. Y., & Qi, M. (2010). Synthesis, characterization and crystallization of poly (ethylene glycol)-b-poly(ε-caprolactone). Advanced Materials Research, 152–153, 1665–1668. https://doi.org/10.1016/j.polymer.2003.09.012
Llana-Ruiz-Cabello, M., Pichardo, S., Maisanaba, S., Puerto, M., Prieto, A. I., Gutierrez-Praena, D., Jos, A., & Camean, A. M. (2015). In vitro toxicological evaluation of essential oils and their main compounds used in active food packaging: A review. Food and Chemical Toxicology, 81, 9–27. https://doi.org/10.1016/j.fct.2015.03.030
Manso, S., Cacho-Nerin, F., Becerril, R., & Nerín, C. (2013). Combined analytical and microbiological tools to study the effect on Aspergillus flavus of cinnamon essential oil contained in food packaging. Food Control, 30(2), 370–378. https://doi.org/10.1016/j.foodcont.2012.07.018
Mascheroni, E., 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(10), 1582–1591. https://doi.org/10.1016/j.foodcont.2011.03.014
Min, T., Sun, X., Yuan, Z., Zhou, L., Jiao, X., Zha, J., Zhu, Z., & Wen, Y. (2021). Novel antimicrobial packaging film based on porous poly (lactic acid) nanofiber and polymeric coating for humidity-controlled release of thyme essential oil. Lwt. https://doi.org/10.1016/j.lwt.2020.110034
Mitcham, E. (2007). Quality of berry associated with preharvest and postharvest conditions. In Y. Zhao (Ed.), Berry fruit (pp. 213–214). CRC Press, Boca Raton.
Mutlu-Ingok, A., Devecioglu, D., Dikmetas, D. N., Karbancioglu-Guler, F., & Capanoglu, E. (2020). Antibacterial, antifungal, antimycotoxigenic, and antioxidant activities of essential oils: An updated review. Molecules. https://doi.org/10.3390/molecules25204711
Nowicka, A., Kucharska, A. Z., Sokol-Letowska, A., & Fecka, I. (2019). Comparison of polyphenol content and antioxidant capacity of strawberry fruit from 90 cultivars of Fragariaxananassa Duch. Food Chemistry, 270, 32–46. https://doi.org/10.1016/j.foodchem.2018.07.015
Ocal, H., Arica-Yegin, B., Vural, I., Goracinova, K., & Calis, S. (2014). 5-Fluorouracil-loaded PLA/PLGA PEG-PPG-PEG polymeric nanoparticles: Formulation, in vitro characterization and cell culture studies. Drug Development and Industrial Pharmacy, 40(4), 560–567. https://doi.org/10.3109/03639045.2013.775581
Paris, M. J., Ramírez-Corona, N., Palou, E., & López-Malo, A. (2020). Modelling release mechanisms of cinnamon (Cinnamomum zeylanicum) essential oil encapsulated in alginate beads during vapor-phase application. Journal of Food Engineering. https://doi.org/10.1016/j.jfoodeng.2020.110024
Peretto, G., Du, W.-X., Avena-Bustillos, R. J., Sarreal, S. B. L., Hua, S. S. T., Sambo, P., & McHugh, T. H. (2014). Increasing strawberry shelf-life with carvacrol and methyl cinnamate antimicrobial vapors released from edible films. Postharvest Biology and Technology, 89, 11–18. https://doi.org/10.1016/j.postharvbio.2013.11.003
Pinilla, C. M. B., Reque, P. M., & Brandelli, A. (2020). Effect of oleic acid, cholesterol, and octadecylamine on membrane stability of freeze-dried liposomes encapsulating natural antimicrobials. Food and Bioprocess Technology, 13(4), 599–610. https://doi.org/10.1007/s11947-020-02419-8
Plati, F., & Paraskevopoulou, A. (2022). Micro- and nano-encapsulation as tools for essential oils advantages’ exploitation in food applications: The case of oregano essential oil. Food and Bioprocess Technology, 15(5), 949–977. https://doi.org/10.1007/s11947-021-02746-4
Prakash, B., Kujur, A., Yadav, A., Kumar, A., Singh, P. P., & Dubey, N. K. (2018). Nanoencapsulation: An efficient technology to boost the antimicrobial potential of plant essential oils in food system. Food Control, 89, 1–11. https://doi.org/10.1016/j.foodcont.2018.01.018
Radi, M., Ahmadi, H., & Amiri, S. (2022). Effect of cinnamon essential oil-loaded nanostructured lipid carriers (NLC) against Penicillium citrinum and Penicillium expansum involved in tangerine decay. Food and Bioprocess Technology, 15(2), 306–318. https://doi.org/10.1007/s11947-021-02737-5
Romanazzi, G., Smilanick, J. L., Feliziani, E., & Droby, S. (2016). Integrated management of postharvest gray mold on fruit crops. Postharvest Biology and Technology, 113, 69–76. https://doi.org/10.1016/j.postharvbio.2015.11.003
Sharma, S., Barkauskaite, S., Jaiswal, A. K., & Jaiswal, S. (2021). Essential oils as additives in active food packaging. Food Chemistry, 343, 128403. https://doi.org/10.1016/j.foodchem.2020.128403
Suksiriworapong, J., Sripha, K., Kreuter, J., & Junyaprasert, V. B. (2012). Functionalized (poly (varepsilon-caprolactone))(2)-poly (ethylene glycol) nanoparticles with grafting nicotinic acid as drug carriers. International Journal of Pharmaceutics, 423(2), 562–570. https://doi.org/10.1016/j.ijpharm.2011.11.033
Thonggoom, O., Punrattanasin, N., Srisawang, N., Promawan, N., & Thonggoom, R. (2016). In vitro controlled release of clove essential oil in self-assembly of amphiphilic polyethylene glycol-block-polycaprolactone. Journal of Microencapsulation, 33(3), 239–248. https://doi.org/10.3109/02652048.2016.1156173
Tyrrell, Z. L., Shen, Y., & Radosz, M. (2011). Near-critical fluid micellization for high and efficient drug loading: Encapsulation of paclitaxel into PEG-b-PCL micelles. The Journal of Physical Chemistry C, 115(24), 11951–11956. https://doi.org/10.1021/jp202335r
Venkatraman, S. S., Jie, P., Min, F., Freddy, B. Y., & Leong-Huat, G. (2005). Micelle-like nanoparticles of PLA-PEG-PLA triblock copolymer as chemotherapeutic carrier. International Journal of Pharmaceutics, 298(1), 219–232. https://doi.org/10.1016/j.ijpharm.2005.03.023
Viacava, G. E., Cenci, M. P., & Ansorena, M. R. (2022). Effect of chitosan edible coatings incorporated with free or microencapsulated thyme essential oil on quality characteristics of fresh-cut carrot slices. Food and Bioprocess Technology, 15(4), 768–784. https://doi.org/10.1007/s11947-022-02783-7
Wang, C., Liang, J., Deng, X., Long, C., Xie, C., Chen, X., Zhang, L., Guo, Q., Wang, Y., Wang, Y., Luo, F., & Qian, Z. (2013). Synthesis, characterization, and application of amino-terminated poly (ethylene glycol)-block-poly (epsilon-caprolactone) copolymer for paclitaxel. Journal of Nanoscience and Nanotechnology, 13(1), 68–76. https://doi.org/10.1166/jnn.2013.6695
Xiao, N. Y., Zhang, X. Q., Ma, X. Y., Luo, W. H., Li, H. Q., Zeng, Q. Y., Zhong, L., & Zhao, W. H. (2020). Construction of EVA/chitosan based PEG-PCL micelles nanocomposite films with controlled release of iprodione and its application in pre-harvest treatment of grapes. Food Chemistry, 331, 127277. https://doi.org/10.1016/j.foodchem.2020.127277
Xiao, Z., Jia, S., Bao, H., Niu, Y., Ke, Q., & Kou, X. (2021). Protection of agarwood essential oil aroma by nanocellulose-graft-polylactic acid. International Journal of Biological Macromolecules, 183, 743–752. https://doi.org/10.1016/j.ijbiomac.2021.04.097
Yang, F. -L., Li, X. -G., Zhu, F., & Lei, C. -L. (2009). Structural characterization of nanoparticles loaded with garlic essential oil and their insecticidal activity against Tribolium castaneum (Herbst) (Coleoptera: Tenebrionidae). Journal of Agricultural and Food Chemistry, 57(21), 10156–10162. https://doi.org/10.1021/jf9023118
Yin, H., Wang, C., Yue, J., Deng, Y., Jiao, S., Zhao, Y., Zhou, J., & Cao, T. (2021). Optimization and characterization of 1,8-cineole/hydroxypropyl-β-cyclodextrin inclusion complex and study of its release kinetics. Food Hydrocolloids. https://doi.org/10.1016/j.foodhyd.2020.106159
Acknowledgements
We appreciated the generous help from Nanjing Forestry University Engineering Center and Advanced Analysis and Testing Center.
Funding
This study was funded by the Independent Innovation Project of Jiangsu Province Academy of Agricultural Sciences (CX(21)3030), the National Key R&D Program of China (2019YFD1002300), Science and Technology Key R&D Program of Shaanxi Province (NO. 2021SF-339), and Science and Technology Key R&D Program of Xianyang (NO. 2021ZDYF-SF-0030).
Author information
Authors and Affiliations
Contributions
Yali Luo: data curation; investigation; validation; writing—original draft. Xuemei Ge: conceptualization, manuscript revision, funding acquisition. Wen Shen: conceptualization, manuscript revision, funding acquisition. Tingting Li: conceptualization, manuscript revision, funding acquisition. Shuangfeng Guo: data curation, investigation, writing—review and editing. Jingyi Su: data curation, investigation. Zhaoxin Cao: data curation, investigation. Zhiming Liu: data curation, investigation. Shang Wu: data curation, investigation. Yueyang Mao: data curation, investigation. Yan Zheng: writing—review and editing.
Corresponding authors
Ethics declarations
Competing Interests
The authors declare no competing interests.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
Springer Nature or its licensor holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Luo, Y., Su, J., Guo, S. et al. Preparation of Humidity-Responsive Cinnamon Essential Oil Nanomicelles and its Effect on Postharvest Quality of Strawberries. Food Bioprocess Technol 15, 2723–2736 (2022). https://doi.org/10.1007/s11947-022-02906-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11947-022-02906-0