Attainment and Characterization of Orange Essential Oil Obtained from Residues of Citrus sinensis 'Valencia'
DOI:
https://doi.org/10.33448/rsd-v11i9.31876Keywords:
Limonene; Orange Essential Oil; Hydrodistillation; Antimicrobial Action; Antioxidant activity.Abstract
The implementation of less aggressive alternatives to the environment, based on the reuse of residues, is increasingly necessary, and is a market trend. In this context, the present work aimed to extract and characterize the orange essential oil obtained from residues of Citrus sinensis 'Valencia' with a view to maximizing the yield of limonene, evaluating it in terms of its antimicrobial and antioxidant potential. Extraction was performed by hydrodistillation and soxhlet methods. Essential oil characterization was performed by gas chromatography with flame ionization detector (GC-FID) and the chemical structure of limonene was confirmed by mass spectrometry (GC-MS). The effect of variables on liquid-liquid extraction after hydrodistillation was evaluated from an experimental design, obtaining a higher global yield of limonene in the essential oil under conditions of 90 minutes and volumetric ratio 100:10 (solute:solvent). The essential oil obtained in the best process condition showed antimicrobial action against Staphylococcus aureus and Proteus mirabilis, with minimum inhibitory concentrations of 0.151 g∙mL-1 and 0.302 g∙mL-1, respectively, evaluated by the broth microdilution method. Moreover, the essential oil showed an antioxidant activity of 84.64 ± 2.35% for a concentration of 93.44 μg∙mL-1 and an IC50 of 24.72 μg∙mL-1, evaluated by the 2,2-diphenyl-1-Picrylhydrazyl (DPPH) free radical scavenging method. The results obtained allows to conclude that the extraction of orange essential oil from residues of Citrus sinensis 'Valencia' by the proposed route is feasible and that it has potential as an antimicrobial and antioxidant additive for future applications.
References
Azambuja, W. (2021). Limoneno. https://www.oleosessenciais.org/limoneno/.
Barros, C. B. (1986). Óleos Essenciais Cítricos do Brasil. (2a. Ed.). Campinas: Fundação Cargill, 1986.
Battista, F., Remelli, G. & Bolzonella, S. Z. E. D. (2020). Valorização de casca de laranja, recuperação de limoneno, ácido graxos voláteis e produção de biogás. ACS Quimica Sustentavel & Engenharia, 8(17), 6834-6843.
Bezić, N., Skočibušić, M., Dunkić, V. & Radonić, A. (2003). Composition and antimicrobial activity of Achillea clavennae L. essential oil. Phytotherapy Research, 17(9), 1037-1040. 10.1002/ptr.1290.
Bizzo, H. R., Hovell, A. M. C. & Rezende, C. M. (2009). Óleos essenciais no Brasil: aspectos gerais, desenvolvimento e perspectivas. Química Nova, 32, 588-594. 10.1590/S0100-40422009000300005.
Blažeković, B., Yang, W., Wang, Y., Li, C., Kindl, M., Pepeljnjak, S. & Vladimir-Knežević, S. (2018). Chemical composition, antimicrobial and antioxidant activities of essential oils of Lavandula × intermedia ‘Budrovka’ and L. angustifolia cultivated in Croatia. Industrial Crops and Products, 123, 173-182. 10.1016/j.indcrop.2018.06.041.
Boutekedjiret, C., Bentahar, F., Belabbes, R., Bessiere, J. M. (2003). Extraction of rosemary essential oil by steam distillation and hydrodistillation. Flavour and Fragrance Journal, 18(6), 481-484. 10.1002/ffj.1226.
Brand-Williams, W., Cuvelier, M. E. & Berset, C. (1995). Use of a free radical method to evaluate antioxidant activity. Food Science and Technology Lebensmittel-Wissenschaft & Technologie, 28(1), 25-30. 10.1016/S0023-6438(95)80008-5.
Campelo, L. M. L., Sá, C. G., Feitosa, C. M., Sousa, G. F. & Freitas, R. M. (2013). Constituintes químicos e estudos toxicológicos do óleo essencial extraído das folhas de Citrus limon Burn (Rutaceae). Revista Brasileira de Plantas Medicinais, 15(4), 708-716. 10.1590/S1516-05722013000500011.
Associação Nacional dos Exportadores de Sucos Cítricos - CITRUSBR. (2022). https://citrusbr.com/.
Clinical and Laboratory Standards Institute - CLSI. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically - CLSI document M07-A11 (ISBN 1-56238-837-1). (11a Ed). Pennsylvania: Clinical and Laboratory Standards Institute, 2018.
Colberg, J., Arat, S., Esguevillas, M. G., France, S., Huot, K., Kumar, R., Laity, D., Lall, M., Lee, J., Magano, J., Piper, J., Richardson, P., Roosen, P. & Watson, R. (2022). Pfizer’s Green Chemistry Program. https://communities.acs.org/t5/GCI-Nexus-Blog/Pfizer-s-Green-Chemistry-Program/ba-p/86557.
Cox, S. D., Mann, C. M., Markham, J. L., Bell, H. C., Gustafson, J. E., Warmington, J. R. & Wyllie, S. G. (2000). The mode of antimicrobial action of the essential oil of Melaleuca alternifolia (tea tree oil). Journal of Applied Microbiology, 88(1), 170-175. 10.1046/j.1365-2672.2000.00943.x.
Değirmenci, H. & Erkurt, H. (2020). Relationship between volatile components, antimicrobial and antioxidant properties of the essential oil, hydrosol and extracts of Citrus aurantium L. flowers. Journal of Infection and Public Health, 13(1), 58-67. 10.1016/j.jiph.2019.06.017.
De Moura, M. R. & Pires, V. G. A. (2017). Preparação de novos filmes poliméricos contendo nanoemulsões do óleo de melaleuca, copaíba e limão para aplicação como biomaterial. Química Nova, 40, 1-5. 10.21577/0100-4042.20160130.
Ehsani A., Alizadeh O., Hashemi M., Afshari A. & Aminzare M. (2017). Phytochemical, antioxidant and antibacterial properties of Melissa officinalis and Dracocephalum moldavica essential oils. Veterinary Research Forum, 8(3), 223-229.
Favela-Hernández, J. M. J., González-Santiago, O., Ramírez-Cabrera, M. A., Esquivel-Ferriño, P. C. & Camacho-Corona M. R. (2016). Chemistry and pharmacology of Citrus sinensis. Molecules, 21(2), 247. 10.3390/molecules21020247.
Ferronatto, A. N. & Rossi, R. C. (2018). Extração e aplicação do óleo essencial da casca da laranja como um ingrediente natural. Estudos Tecnológicos em Engenharia, 12(2), 78-93. 10.4013/ete.2018.122.05.
Flores, P. I. G., Bañuelos-Valenzuela, R., Delgadillo-Ruiz, L., Meza-López, C. & Echavarría-Cháirez, F. (2019). Actividad antibacteriana de cinco compuestos terpenoides: carvacrol, limoneno, linalool, α-terpineno y timol. Tropical and Subtropical Agroecosystems, 22(2), 241-248.
Fundo de Defesa da Citricultura - FUNDECITRUS. (2022). https://www.fundecitrus.com.br/.
Guo, Q., Liu, K., Deng, W., Zhong, B., Yang, W. & Chun, J. (2018). Chemical composition and antimicrobial activity of Gannan navel orange (Citrus sinensis Osbeck cv. Newhall) peel essential oils. Food science & nutrition, 6(6), 1431-1437. 10.1002/fsn3.688.
International Union of Pure and Applied Chemistry (IUPAC), Standard methods for the analysis of oils, fats and derivatives. (6a Ed). Oxford: Pergamon Press, 1979.
İşcan, G. (2017). Antibacterial and Anticandidal Activities of Common Essential Oil Constituents. Records of Natural Products, 11(4), 374-388.
Li, Z.-H., Cai, M., Liu, Y.-S., Sun, P.-L. & Luo, S.-L. (2019). Antibacterial Activity and Mechanisms of Essential Oil from Citrus medica L. var. sarcodactylis. Molecules, 24(8), 1577. 10.3390/molecules24081577.
Maia, A. J., Schwan-Estrada, K. R. F., Faria, C. M. D. R., Oliveira, J. S. B., Jardinetti, V. A. & Batista, B. N. (2014). Óleo essencial de alecrim no controle de doenças e na indução de resistência em videira. Pesquisa Agropecuária Brasileira, 49, 330-339. 10.1590/S0100-204X2014000500002.
Majnooni, M. B., Mansouri, K., Gholivand, M. B., Mostafaie, A., Mohammadi-Motlagh, H. R., Afnanzad, N. S., Abolghasemi. M. M. & Piriyaei, M. (2012). Chemical composition, cytotoxicity and antioxidant activities of the essential oil from the leaves of Citrus aurantium L. African Journal of Biotechnology, 11 (2), 498-503. 10.5897/AJB11.1449.
Maróstica Junior, M. R. Rocha e Silva, T. A. A., Franchi, G. C., Nowill, A., Pastore, G. M. & Hyslop, S. (2009). Antioxidant potential of aroma compounds obtained by limonene biotransformation of orange essential oil. Food Chemistry, 116(1), 8-12. 10.1016/j.foodchem.2009.01.084.
Nazzaro, F., Fratianni, F., De Martino, L., Coppola, R. & De Feo, V. (2013). Effect of Essential Oils on Pathogenic Bacteria. Pharmaceuticals, 6(12), 1451-1474. 10.3390/ph6121451.
Nellis, S. C., Correia, A. de F. K. & Spoto, M. H. F. (2017). Extração e quantificação de carotenoides em minitomate desidratado (Sweet Grape) através da aplicação de diferentes solventes. Brazilian Journal of Food Technology, 20. 10.1590/1981-6723.15616.
O'Bryan, C. A., Crandall, P. G., Chalova, V. I. & Ricke, S. C. (2008). Orange essential oils antimicrobial activities against Salmonella spp. Journal of Food Science, 73(6), 264-267. 10.1111/j.1750-3841.2008.00790.x.
Ozturk, B., Winterburn, J. & Conzalez-Miquel, M. (2019). Orange peel waste valorisation through limonene extraction using bio-based solvents. Biochemical Engineering Journal, 151. 10.1016/j.bej.2019.107298.
Pires, T, Ribeiro, M. G. & Machado, A. (2018). Extração do R-(+)-limoneno a partir das cascas de laranja: avaliação e otimização da verdura dos processos de extração tradicionais. Química Nova, 41, 355-365. 10.21577/0100-4042.20170139.
PuBChem - Open Chemistry Database. Limonene. https://pubchem.ncbi.nlm.nih.gov/compound/Limonene.
Raut, J. S. & Karuppayil, S. M. (2014). A status review on the medicinal properties of essential oils. Industrial Crops and Products, 62, 250-264. 10.1016/j.indcrop.2014.05.055.
Reynertson, K. A., Basile, M. J. & Kennelly, E. J. (2005). Antioxidant potential of seven myrtaceous fruits. Ethnobotany Research and Applications, 3, 25-36.
Siddiqui, S. A., Pahmeyer, M. J., Assadpour, E. & Jafari, S. M. (2022). Extraction and purification of d-limonene from orange peel wastes: Recent advances. Industrial Crops and Products, 177, 114484. 10.1016/j.indcrop.2021.114484.
Sigma Aldrich. (2022). GC Analise of Lemon Essential Oil on SLB. https://www.sigmaaldrich.com/BR/pt/technical-documents/protocol/analytical-chemistry/gas-chromatography/gc-analysis-of-lemon-essential-oil-slb.
Silva, R. S., Ribeiro, C. M. R., Borges, M. N. & Blois, G. S. (2009). Óleo essencial de limão no ensino da cromatografia em camada delgada. Química Nova, 32, 2234-2237. 10.1590/S0100-40422009000800042.
Simonetti, E., Ethur, M. E., Castro, L. C., Kauffmann, C., Giacomin, A. C., Ledur, A., Arossi, K., Pacheco, L. A., Goettert, M. I., Faleiro, D. & Freitas, E. M. (2016). Avaliação da atividade antimicrobiana de extratos de Eugenia anomala e Psidium salutare (Myrtaceae) frente à Escherichia coli e Listeria monocytogenes. Revista Brasileira de Plantas Medicinais, 18, 9-18. 10.1590/1983-084X/15_005.
Sun, J. (2007). D-Limonene: safety and clinical applications. Alternative Medicine Review, 12(3).
Swamy, M. K., Akhtar, M. S. & Sinniah, U. R. (2016). Antimicrobial Properties of Plant Essential Oils against Human Pathogens and Their Mode of Action: An Updated Review. Evidence-Based Complementary and Alternative Medicine, 2016, 1-21. 10.1155/2016/3012462.
Torres-Alvarez, C., González, A. N., Rodríguez, J., Castillo, S., Leos-Rivas, C. & Báez-González, J. G. (2017). Chemical composition, antimicrobial, and antioxidant activities of orange essential oil and its concentrated oils. CyTA-Journal of Food, 15(1), 129-135. 10.1080/19476337.2016.1220021.
Vitti, A. M. S. & Brito, J. O. (2003). Óleo essencial de eucalipto. Documentos florestais, 17, 1-26.
Yang, C., Chen, H., Chen, H., Zhong, B., Luo, X. & Chun, J. (2017). Antioxidant and Anticancer Activities of Essential Oil from Gannan Navel Orange Peel. Molecules, 22(8), 1391. 10.3390/molecules22081391.
Zeferino, R. C. F. (2021). Síntese de acetato de geranila e acetato de nerila via catálise heterogênea com resina de troca iônica e caracterização dos ésteres para potenciais aplicações como aditivos antimicrobianos. (Tese de Doutorado em Engenharia Química, Universidade Federal de Santa Catarina, Florianópolis, Santa Catarina, Brasil).
Zhang, M. L., Tao, N. G. & Liu, Y. J., (2009). Chemical composition and antimicrobial activities of essential oil from the peel of bingtang sweet orange (Citrus sinensis Osbeck). International Journal Of Food Science & Technology, 44(7), 1281-1285. 10.1111/j.1365-2621.2009.01947.x.
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2022 Vinícius Tres Orso; Wellyngton Luiz Rodrigues; Jéssica Dalla Cort; Micheli Zanetti; Gustavo Lopes Colpani; Rubieli Carla Frezza Zeferino
This work is licensed under a Creative Commons Attribution 4.0 International License.
Authors who publish with this journal agree to the following terms:
1) Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
2) Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
3) Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work.
