Abstract
Stabilization of reactive organic species by encapsulation in self-assembly supramolecules is a popular technique. Citral, a common antimicrobial and flavor compound, is highly sensitive to oxidation, especially when exposed to elevated temperature and light. In this study we evaluated the encapsulation efficiency of citral in cyclodextrin-metal organic framework (CDMOF) to prevent oxidation, provide chemical stability, and control the release of citral for various industrial applications including packaging. Computational simulations indicated the formation of stable inclusion complex between CDMOF and citral with binding energy of the IC approximately − 3.89 kcal mol−1. We observed around 11.83% w/w inclusion of citral in CDMOF as measured using TGA. Host–guest interactions between CDMOF and citral were further elucidated using FTIR, DSC, and SEM. Encapsulation of CDMOF in citral offers higher temperature stability, and extended-release kinetics.
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References
Nagarajan, V., Kizhaeral, S.S., Subramanian, M., Rajendran, S., Ranjan, J.: Encapsulation of a volatile biomolecule (hexanal) in cyclodextrin metal–organic frameworks for slow release and its effect on preservation of mangoes. ACS Food Sci. Technol. 1(10), 1936–1944 (2021)
Sultana, A., Kathuria, A., Gaikwad, K.K.: Metal–organic frameworks for active food packaging: a review. Environ. Chem. Lett. 20, 1479–1495 (2022)
Kathuria, A., Abiad, M.G., Auras, R.: Deterioration of metal–organic framework crystal structure during fabrication of poly (l-lactic acid) mixed-matrix membranes. Polym. Int. 62(8), 1144–1151 (2013)
Chopra, S., Dhumal, S., Abeli, P., Beaudry, R., Almenar, E.: Metal-organic frameworks have utility in adsorption and release of ethylene and 1-methylcyclopropene in fresh produce packaging. Postharvest Biol. Technol. 130, 48–55 (2017)
Han, Y., Liu, W., Huang, J., Qiu, S., Zhong, H., Liu, D., Liu, J.: Cyclodextrin-based metal-organic frameworks (CD-MOFs) in pharmaceutics and biomedicine. Pharmaceutics 10(4), 271 (2018)
Farmer, E.E., Davoine, C.: Reactive electrophile species. Curr. Opin. Plant Biol. 10(4), 380–386 (2007)
LoPachin, R.M., Gavin, T.: Molecular mechanisms of aldehyde toxicity: a chemical perspective. Chem. Res. Toxicol. 27(7), 1081–1091 (2014)
Lehtonen, M., Kekäläinen, S., Nikkilä, I., Kilpeläinen, P., Tenkanen, M., Mikkonen, K.S.: Active food packaging through controlled in situ production and release of hexanal. Food Chem. 5, 100074 (2020)
Bertacche, V., Lorenzi, N., Nava, D., Pini, E., Sinico, C.: Host–guest interaction study of resveratrol with natural and modified cyclodextrins. J. Incl. Phenom. Macrocycl. Chem. 55, 279–287 (2006)
Galan, A., Ballester, P.: Stabilization of reactive species by supramolecular encapsulation. Chem. Soc. Rev. 45(6), 1720–1737 (2016)
Silva, C.D., Guterres, S.S., Weisheimer, V., Schapoval, E.E.: Antifungal activity of the lemongrass oil and citral against Candida spp. Braz. J. Infect. Dis. 12, 63–66 (2008)
Dai, J., Bai, M., Li, C., San Cheang, W., Cui, H., Lin, L.: Antibacterial properties of citral against Staphylococcus aureus: from membrane damage to metabolic inhibition. Food Biosci. 53, 102770 (2023)
Ding, B., Chen, H., Tan, J., Meng, Q., Zheng, P., Ma, P.A., Lin, J.: ZIF-8 nanoparticles evoke pyroptosis for high-efficiency cancer immunotherapy. Angew. Chem. 135(10), e202215307 (2023)
Ke, Q., Jing, P., Wan, Y., Xia, T., Zhang, L., Cao, X., Jiang, K.: Sulfonated vitamin K3 mediated bimetallic metal-organic framework for multistage augmented cancer therapy. J. Colloid Interface Sci. 654, 224–234 (2024)
Serrano, M., Martínez-Romero, D., Guillén, F., Valverde, J.M., Zapata, P.J., Castillo, S., Valero, D.: The addition of essential oils to MAP as a tool to maintain the overall quality of fruits. Trends Food Sci. 19(9), 464–471 (2008)
Navarro-Martínez, A., López-Gómez, A., Martínez-Hernández, G.B.: Potential of essential oils from active packaging to highly reduce ethylene biosynthesis in broccoli and apples. ACS Food Sci. Technol. 1(6), 1050–1058 (2021)
Rabbany, A.B.M.G., Mizutani, F.: Effect of essential oils on ethylene production and ACC content in apple fruit and peach seed tissues. J. Jpn. Soc. Hortic. Sci. 65(1), 7–13 (1996)
Wei, L., Chen, C., Wan, C., Chen, M., Chen, J.: Citral delays postharvest senescence of kiwifruit by enhancing antioxidant capacity under cold storage. J. Food Qual. 2021, 6684172 (2021)
Aytac, Z., Celebioglu, A., Yildiz, Z.I., Uyar, T.: Efficient encapsulation of citral in fast-dissolving polymer-free electrospun nanofibers of cyclodextrin inclusion complexes: high thermal stability, longer shelf-life, and enhanced water solubility of citral. Nanomaterials 8(10), 793 (2018)
Sun, Y., Guo, D., Hua, Z., Sun, H., Zheng, Z., Xia, X., Shi, C.: Attenuation of multiple Vibrio parahaemolyticus virulence factors by citral. Front. Microbiol. 10, 894 (2019)
Maksimowski, P., Rumianowski, T.: Properties of the gamma-cyclodextrin/CL-20 system. Cent. Eur. J. Energ Mater. 13(1), 217–229 (2016)
Kathuria, A., El Badawy, A., Al Ghamdi, S., Hamachi, L.S., Kivy, M.B.: Environmentally benign bioderived, biocompatible, thermally stable MOFs suitable for food contact applications. Trends Food Sci. 138, 323–338 (2023)
Kathuria, A., Lee, Y.S., Shin, J., Kivy, M.: Crystalline γ-cyclodextrin metal organic framework nano-containers for encapsulation of benzaldehyde and their host–guest interactions. J. Incl. Phenom. Macrocycl. Chem. 102(9–10), 781–790 (2022)
Kathuria, A., Pauwels, A.K., Buntinx, M., Shin, J., Harding, T.: Inclusion of ethanol in a nano-porous, bio-based metal organic framework. J. Incl. Phenom. Macrocycl. Chem. 95, 91–98 (2019)
Hanwell, M.D., Curtis, D.E., Lonie, D.C., Vandermeersch, T., Zurek, E., Hutchison, G.R.: Avogadro: an advanced semantic chemical editor, visualization, and analysis platform. J. Cheminform. 4, 17 (2012)
Morris, G.M., Huey, R., Lindstrom, W., Sanner, M.F., Belew, R.K., Goodsell, D.S., Olson, A.J.: Auto dock 4 and auto dock tools 4: automated docking with selective receptor flexibility. J. Comput. Chem. 30, 2785–2791 (2010)
Trott, O., Olson, A.J.: AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization and multithreading. J. Comput. Chem. 31, 455–461 (2010)
Thompson, M.A.: Molecular docking using ArgusLab, an efficient shape-based search algorithm and the a score scoring function. ACS Meeting, Philadelphia (2004)
Momma, K., Izumi, F.: VESTA 3 for three-dimensional visualization of crystal, volumetric and morphology data. J. Appl. Crystallogr. 44, 1272–1276 (2011)
Zhang, B., Huang, J., Liu, K., Zhou, Z., Jiang, L., Shen, Y., Zhao, D.: Biocompatible cyclodextrin-based metal-organic frameworks for long-term sustained release of fragrances. Ind. Eng. Chem. Res. 58, 19767–19777 (2019)
Kathuria, A., Harding, T., Auras, R., Kivy, M.B.: Encapsulation of hexanal in bio-based cyclodextrin metal organic framework for extended release. J. Incl. Phenom. Macrocycl. Chem. 101, 121–130 (2021)
He, Y., Zhang, W., Guo, T., Zhang, G., Qin, W., Zhang, L., Wang, C., Zhu, W., Yang, M., Hu, X., Singh, V., Wu, L., Gref, R., Zhang, J.: Drug nanoclusters formed in confined nano-cages of CD-MOF: dramatic enhancement of solubility and bioavailability of azilsartan. Acta Pharm. Sin. B 9, 97–106 (2019)
Aoun, M., Chater, M., Marecot, P., Especel, C., Citral, L.G.: hydrogenation over Pt-M/CeO2 catalysts (M = Zn, Zr). In: Studies in surface science and catalysis, pp. 237–240. Elsevier, Amsterdam (2010)
Zhu, G., Feng, N., Xiao, Z., Zhou, R., Niu, Y.: Production and pyrolysis characteristics of citral–monochlorotriazinyl-β-cyclodextrin inclusion complex. J. Therm. Anal. Calorim. 120, 1811–1817 (2015)
Dreier, L.B., Bonn, M., Backus, E.H.: Hydration and orientation of carbonyl groups in oppositely charged lipid monolayers on water. J. Phys. Chem. B 123(5), 1085–1089 (2019)
Nie, B., Stutzman, J., Xie, A.: A vibrational spectral maker for probing the hydrogen-bonding status of protonated Asp and Glu residues. Biophys. J. 88(4), 2833–2847 (2005)
Zhang, D.C., Liu, J., Wang, C., Liu, Y., Wang, J.H., Han, X.: Application of metal-organic frameworks in the purification of indoor hexanal: experiments and DFT calculations. Build. Environ. 182, 107095 (2020)
Al-Ghamdi, S., Kathuria, A., Abiad, M., Auras, R.: Synthesis of nanoporous carbohydrate metal-organic framework and encapsulation of acetaldehyde. J. Cryst. Growth 451, 72–78 (2016)
Ficarra, R., Ficarra, P., Di Bella, M.R., Raneri, D., Tommasini, S., Calabro, M.L., Gamberini, M.C., Rustichelli, C.: Study of β-blockers/β-cyclodextrins inclusion complex by NMR, DSC, X-ray and SEM investigation. J. Pharm. Biomed. Anal. 23(1), 33–40 (2000)
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The authors conceptualized the study together. AK coordinated various experimental tasks and oversaw the manuscript. LK, KRG, and AEB helped with the analysis and manuscript writing. MK led computational studies, host-guest interactions, XRD, SEM and writing.
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Kathuria, A., Kumar, L., Gaikwad, K.K. et al. Micro-encapsulation of citral using edible γ-cyclodextrin metal organic framework. J Incl Phenom Macrocycl Chem 104, 99–108 (2024). https://doi.org/10.1007/s10847-024-01220-w
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DOI: https://doi.org/10.1007/s10847-024-01220-w