Improvement of Aroma and Shelf-Life of Non-alcoholic Beverages Through Cyclodextrins-Limonene Inclusion Complexes
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Limonene is a monoterpene flavor compound found in several beverages. However, it easily degrades by oxidation reactions at acidic environment contributing to an undesirable off-flavor. Encapsulation technologies can protect compounds from degradation. This work focuses on the effect of using complexes of limonene with α-, β-, and γ- and HP-β-cyclodextrins in non-alcoholic beverages to improve flavor and shelf-life stability due to the chemical structure of cyclodextrins. Spray-drying technology was applied to prepare different cyclodextrin/limonene forms, from which the most promising was selected and further applied in simulated lemon juice beverages. Different drying process conditions were tested, namely feed temperature (120, 160, and 180 °C) and setting of prior incubation (temperature, room and 50 °C; time, 0.17 and 24 h). An inlet temperature of 160 °C favored the encapsulation of limonene into resulting nano/microparticles. Moreover, incubation for 24 h enhanced limonene retention for all complexes, especially for β-cyclodextrin/limonene complexes, which achieved 66% of encapsulation efficiency and a 6.25 w/w of limonene load. The β-cyclodextrin/limonene particles which enabled higher load (160 °C, 24 h) presented particle size ranging between 1 and 3 μm and were chosen to undergo an accelerated aging process in a lemon juice beverage model. This study revealed that the limonene content decreased over time for model and supplemented juice, but decreased less when β-cyclodextrin/limonene particles were added. After 10 days, which mimics 9 months of storage, 40% of complexed limonene remained in the model beverage.
Keywordsα-Cyclodextrin β-Cyclodextrin γ-Cyclodextrin HP-β-cyclodextrin Limonene Spray-drying
This study was financially supported by ITQB/IBET, IST/iBB and SUMOL+COMPAL. Furthermore, this work acknowledges Fundação para a Ciência e Tecnologia (FCT) through PEst-OE/EQB/LA0004/2011, the financial support received from FCT through the doctoral (SFRH/BDE/51856/2012) fellowship and R&D units iNOVA4Health-UID/Multi/04462/2013 and GreenIT-UID/Multi/04551/2013, programs financially supported by FCT/Ministério da Educação e Ciência, through national funds and co-funded by FEDER under the PT2020 Partnership Agreement. Also acknowledged is the funding received from FCT (UID/BIO/04565/2013) and from Programa Operacional Regional de Lisboa 2020 (Project N.007317) in the framework of iBB activities.
Compliance with Ethical Standards
Conflict of Interests
The authors declare that they have no conflict of interests.
- Bakry, A. M., Abbas, S., Ali, B., Majeed, H., Abouelwafa, M. Y., Mousa, A., & Liang, L. (2016). Microencapsulation of oils: A comprehensive review of benefits, techniques, and applications. Comprehensive Reviews in Food Science and Food Safety, 15(1), 143–182. doi: 10.1111/1541-4337.12179.CrossRefGoogle Scholar
- Djordjevic, D., Cercaci, L., Alamed, J., McClements, D. J., & Decker, E. A. (2007). Chemical and physical stability of citral and limonene in sodium dodecyl sulfate-chitosan and gum arabic-stabilized oil-in-water emulsions. Journal of Agricultural and Food Chemistry, 55(9), 3585–3591. doi: 10.1021/jf063472r.CrossRefGoogle Scholar
- Hedges, A. (2009). Cyclodextrins: Properties and Applications. In Starch (pp. 833–851). doi: 10.1016/B978–0–12-746275-2.00022-7
- Huang, D., Ou, B., Hampsch-Woodill, M., Flanagan, J. A., & Deemer, E. K. (2002). Development and validation of oxygen radical absorbance capacity assay for lipophilic antioxidants using randomly methylated beta-cyclodextrin as the solubility enhancer. Journal of Agricultural and Food Chemistry, 50(7), 1815–1821. doi: 10.1021/jf0113732.CrossRefGoogle Scholar
- Koontz, J. L., Marcy, J. E., O’Keefe, S. F., & Duncan, S. E. (2009). Cyclodextrin inclusion complex formation and solid-state characterization of the natural antioxidants alpha-tocopherol and quercetin. Journal of Agricultural and Food Chemistry, 57(4), 1162–1171. doi: 10.1021/jf802823q.CrossRefGoogle Scholar
- Lund, B., & Baird-Parker, T. C. (2000). Microbiological safety and quality of food (Vol. 1). BOOK, Springer Science & Business Media.Google Scholar
- Mortensen, A., Aguilar, F., Crebelli, R., Di Domenico, A., Dusemund, B., Frutos, M. J., et al. (2016) .Re-Reevaluation of β-cyclodextrin (E 459) as a food additive. EFSA Journal, 14(12). doi: 10.2903/j.efsa.2016.4628
- Mourtzinos, I., Makris, D. P., Yannakopoulou, K., Kalogeropoulos, N., Michali, I., & Karathanos, V. T. (2008). Thermal stability of anthocyanin extract of Hibiscus sabdariffa L. in the presence of β-cyclodextrin. Journal of Agricultural and Food Chemistry, 56(21), 10303–10310. doi: 10.1021/jf801389j.CrossRefGoogle Scholar
- Navarro, P., Nicolas, T. S., Gabaldon, J. A., Mercader-Ros, M. T., Calín-Sanchez, Á., Carbonell-Barrachina, Á. A., & Pérez-López, A. J. (2011). Effects of cyclodextrin type on vitamin C, antioxidant activity, and sensory attributes of a mandarin juice enriched with pomegranate and goji berries. Journal of Food Science, 76(5). doi: 10.1111/j.1750-3841.2011.02176.x.
- Nisperos-Carriedo, M. O., & Shaw, P. E. (1990). Volatile flavor components of fresh and processed orange juices. Food Technology, 44(4), 134–138 http://cat.inist.fr/?aModele=afficheN&cpsidt=6896454. Accessed 7 January 2017.Google Scholar
- Samperio, C., Boyer, R., Eigel, W. N., Holland, K. W., McKinney, J. S., O’Keefe, S. F., et al. (2010). Enhancement of plant essential oils’ aqueous solubility and stability using alpha and beta cyclodextrin. Journal of Agricultural and Food Chemistry, 58(24), 12950–12956. doi: 10.1021/jf103275a.CrossRefGoogle Scholar
- Unlusayin, M., Hadaruga, N. G., Rusu, G., Gruia, A. T., Paunescu, V., & Hadaruga, D. I. (2016). Nano-encapsulation competitiveness of omega-3 fatty acids and correlations of thermal analysis and Karl Fischer water titration for European anchovy (Engraulis encrasicolus L.) oil/beta-cyclodextrin complexes. LWT - Food Science and Technology (Vol. 68). Elsevier Ltd. doi: 10.1016/j.lwt.2015.12.017
- Waalkens-Berendsen, D. H., Smits-van Prooije, A. E., & Bär, A. (1998a). Embryotoxicity and teratogenicity study with γ-cyclodextrin in rabbits. Regulatory Toxicology and Pharmacology, 27(2), 172–177.Google Scholar
- Waalkens-Berendsen, D. H., Verhagen, F. J. J., & Bär, A. (1998b). Embryotoxicity and teratogenicity study with γ-cyclodextrin in rats. Regulatory Toxicology and Pharmacology, 27(2), 166–171.Google Scholar
- Yamamoto, C., Furuta, T., & Loon, T. (2011). Molecular encapsulation of citral or d -limonene flavor by spray drying. In Proceedings of the 11th International Congress on Engineering and Food (pp. 7–8). Athens, Greece.Google Scholar
- Yamamoto, C., Neoh, T. L., Honbou, H., Yoshii, H., & Furuta, T. (2012). Kinetic analysis and evaluation of controlled release of d-limonene encapsulated in spray-dried cyclodextrin powder under linearly ramped humidity. Drying Technology, 30(11–12), 1283–1291. doi: 10.1080/07373937.2012.681089.CrossRefGoogle Scholar
- Yuliani, S., Torley, P. J., D’Arcy, B., Nicholson, T., & Bhandari, B. (2006). Extrusion of mixtures of starch and D-limonene encapsulated with beta-cyclodextrin: Flavour retention and physical properties. Food Research International, 39(3), 318–331. doi: 10.1016/j.foodres.2005.08.005.CrossRefGoogle Scholar