Chemical profile, chemical and biological activity of cross essential oil and oil-in-water (O/W) nanoemulsion of Pimpinella anisum (anise) and Laurus nobilis (laurel)
DOI:
https://doi.org/10.5902/2179460X88052Keywords:
Essential oil, Antioxidant, Anti-inflammatoryAbstract
This work aimed to evaluate the chemical profile and the anti-inflammatory and antioxidant activity of bioproducts produced from the cross essential oil of Pimpinella anisum (anise) and Laurus nobilis (bay laurel). For the extraction of EO, the hydrodistillation technique was performed using a modified Clevenger extractor system, and the nanoemulsions were formulated by the phase inversion method. The determination of total phenolic compounds was performed by the Folin-Ciocalteu method. Antioxidant activity was performed by the spectrophotometric method of hydroxyl radical elimination from salicylic acid. The anti-inflammatory activity was evaluated using the heat-induced protein denaturation method of albumin. The CFT determination yielded 54.27 and 1.71 mg EAT/g for cross-EO and EON, respectively. The cross-EO and its bioproducts showed antioxidant and anti-inflammatory activity with satisfactory values for Efficient Concentration (EC50). For the antioxidant capacity of EO, EON, EOM, EONM, EOB, and EONB, EC50 values of 9.72, 7.34, 3.09, 7.90, 111.02, and 12.30 were obtained, respectively. For the anti-inflammatory activity of EO, EON, EOM, EONM, EOB, and EONB, EC50 values of 12.02, 28.96, 4.39, 4.07, 4.27, and 2.99 mg/L were quantified, respectively. It can be stated that the cross-EO and its bioproducts showed satisfactory results, which evidenced the effectiveness of the synergistic properties and its biotechnological potential.
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Aala, J., Ahmadi, M., Golestan, L., Shahidi, S. A., & Shariatifar, N. (2023). Effect of multifactorial free and liposome-coated of bay laurel (Laurus nobilis) and rosemary (Salvia rosmarinus) extracts on the behavior of Listeria monocytogenes and Vibrio parahaemolyticus in silver carp (Hypophthalmichthys molitrix) stored at 4° C. Environmental Research, 216, 114478. doi: https://doi.org/10.1016/j.envres.2022.114478
Adams, R. P. (2017). Identification of essential oil components by gas chromatography/mass spectrometry. 5 online ed. Gruver, TX USA: Texensis Publishing. http://www.juniperus.org/uploads/2/2/6/3/22639912/bk4frontisbnpreface-contents5thedonline2017.pdf
Al-Mijalli, S. H., Mrabti, H. N., Ouassou, H., Flouchi, R., Abdallah, E. M., Sheikh, R. A., ... & Faouzi, M. E. A. (2022). Chemical composition, antioxidant, anti-diabetic, anti-acetylcholinesterase, anti-inflammatory, and antimicrobial properties of Arbutus unedo L. and Laurus nobilis L. essential oils. Life, 12(11), 1876. doi: https://doi.org/10.3390/life12111876
Aumeeruddy-Elalfi, Z., Gurib-Fakim, A., & Mahomoodally, M. F. (2016). Kinetic studies of tyrosinase inhibitory activity of 19 essential oils extracted from endemic and exotic medicinal plants. South African Journal of Botany, 103, 89-94. doi: https://doi.org/10.1016/j.sajb.2015.09.010
Avola, R., Granata, G., Geraci, C., Napoli, E., Graziano, A. C. E., & Cardile, V. (2020). Oregano (Origanum vulgare L.) essential oil provides anti-inflammatory activity and facilitates wound healing in a human keratinocytes cell model. Food and Chemical Toxicology, 144, 111586. doi: https://doi.org/10.1016/j.fct.2020.111586
Bassolé, I. H. N., & Juliani, H. R. (2012). Essential oils in combination and their antimicrobial properties. Molecules, 17(4), 3989-4006. doi: https://doi.org/10.3390/molecules17043989
Belasli, A., Ben Miri, Y., Aboudaou, M., Aït Ouahioune, L., Montañes, L., Ariño, A., & Djenane, D. (2020). Antifungal, antitoxigenic, and antioxidant activities of the essential oil from laurel (Laurus nobilis L.): Potential use as wheat preservative. Food science & nutrition, 8(9), 4717-4729. doi: https://doi.org/10.1002/fsn3.1650
Campos, M. G., Webby, R. F., Markham, K. R., Mitchell, K. A., & Da Cunha, A. P. (2003). Age-induced diminution of free radical scavenging capacity in bee pollens and the contribution of constituent flavonoids. Journal of agricultural and food chemistry, 51(3), 742-745. doi: https://doi.org/10.1021/jf0206466
da Cunha, A. P., Nogueira, M. T., & Roque, O. R. (2012). Plantas aromáticas e óleos essenciais: composição e aplicações. Lisboa (Portugal): Fundação Calouste Gulbenkian.
de Lima, T. C. P., de Almeida, A. F., de Oliveira, E. C. P., Carrera Silva Júnior, J. O., Ribeiro Costa, R. M., Pena Matos, A., & Fonseca Gomes, M. R. (2020). Desenvolvimento de nanogel de copaifera reticulata sobre a lesão muscular em ratos usando fonoforese. Saúde e Pesquisa, 13(1). doi: 10.17765/2176-9206.2020v13n1p181-192
Dhara, L., & Tripathi, A. (2013). Antimicrobial activity of eugenol and cinnamaldehyde against extended spectrum beta-lactamase producing enterobacteriaceae by in vitro and molecular docking analysis. European Journal of Integrative Medicine, 5(6), 527–536. doi: https://doi.org/10.1016/j.eujim.2013.08.005
Dhifi, W., Bellili, S., Jazi, S., Nasr, S. B., El Beyrouthy, M., & Mnif, W. (2018). Phytochemical composition and antioxidant activity of Tunisian Laurus nobilis. Pak. J. Pharm. Sci, 31(6), 2397-2402. https://www.researchgate.net/profile/Wissem-Mnif/publication/328654107_Phytochemical_composition_and_antioxidant_activity_of_Tunisian_Laurus_nobilis/links/5bdab17aa6fdcc3a8db5112e/Phytochemical-composition-and-antioxidantactivity-of-Tunisian-Laurus-nobilis.pdf
El Asbahani, A., Miladi, K., Badri, W., Sala, M., Addi, E. A., Casabianca, H., ... & Elaissari, A. (2015). Essential oils: From extraction to encapsulation. International journal of pharmaceutics, 483(1-2), 220-243. doi: https://doi.org/10.1016/j.ijpharm.2014.12.069
Ercin, E., Kecel-Gunduz, S., Gok, B., Aydin, T., Budama-Kilinc, Y., & Kartal, M. (2022). Laurus nobilis L. essential oil-loaded PLGA as a nanoformulation candidate for cancer treatment. Molecules, 27(6), 1899. doi: https://doi.org/10.3390/molecules27061899
Fadel, H. H. M., El-Ghorab, A. H., Hussein, A. M., El-Massry, K. F., Lotfy, S. N., Ahmed, M. Y. S., & Soliman, T. N. (2020). Correlation between chemical composition and radical scavenging activity of 10 commercial essential oils: Impact of microencapsulation on functional properties of essential oils. Arabian Journal of Chemistry, 13(8), 6815-6827. doi: https://doi.org/10.1016/j.arabjc.2020.06.034
Feijó, A. M., Bueno, M. E. N., Ceolin, T., Linck, C. L., Schwartz, E., Lange, C., ... & Heiden, G. (2012). Plantas medicinais utilizadas por idosos com diagnóstico de Diabetes mellitus no tratamento dos sintomas da doença. Revista Brasileira de Plantas Medicinais, 14, 50-56. doi: https://doi.org/10.1590/S1516-05722012000100008
Ferreira, A. R. A. (2014). Uso de óleos essenciais como agentes terapêuticos (Doctoral dissertation, [sn]). http://hdl.handle.net/10284/4513
Fidan, H. et al. (2019). Composição química e atividade antimicrobiana dos óleos essenciais de Laurus nobilis L. da Bulgária. Moléculas, v. 24, n. 4, pág. 804. https://www1.ibb.unesp.br/Home/Departamentos/Botanica/RBPM-RevistaBrasileiradePlantasMedicinais/artigo10_v6_n2.pdf
Figueredo, G., Özcan, M. M., Chalard, P., Özcan, M. M., Uslu, N., & Al Juhaimi, F. (2020). Chemical composition of essential oil of anise (Pimpinella anisum), cumin (Cuminum cyminum), fennel (Foeniculum vulgare) and parsley (Petroselinum crispum Mill.) seeds. J. Agroaliment. Pro-cesses Technol, 26(1), 01-05. https://journal-of-agroalimentary.ro/admin/articole/79799L1_Guilles_Figueredo_2020_26(1)_1-5.pdf
Goudjil, M. B., Ladjel, S., Bencheikh, S. E., Zighmi, S., & Hamada, D. (2015). Study of the chemical composition, antibacterial and antioxidant activities of the essential oil extracted from the leaves of Algerian Laurus nobilis Lauraceae. Journal of Chemical and Pharmaceutical Research, 7(1), 379-385. https://www.researchgate.net/profile/Mohamed-Goudjil-2/publication/271643791_Study_of_the_chemical_composition_antibacterial_and_antioxidant_activities_of_the_essential_oil_extracted_from_the_leaves_of_Algerian_Laurus_nobilis_Lauraceae/links/54ce4dd00cf29ca810fb8c8a/Study-of-the-chemical-composition-antibacterial-and-antioxidant-activities-of-theessential-oil-extracted-from-the-leaves-of-Algerian-Laurus-nobilis-Lauraceae.pdf
Iannarelli, R., Marinelli, O., Morelli, M. B., Santoni, G., Amantini, C., Nabissi, M., & Maggi, F. (2018). Aniseed (Pimpinella anisum L.) essential oil reduces pro-inflammatory cytokines and stimulates mucus secretion in primary airway bronchial and tracheal epithelial cell lines. Industrial crops and products, 114, 81-86. doi: https://doi.org/10.1016/j.indcrop.2018.01.076
Jonville, M. C., Kodja, H., Strasberg, D., Pichette, A., Ollivier, E., Frédérich, M., ... & Legault, J. (2011). Antiplasmodial, anti-inflammatory and cytotoxic activities of various plant extracts from the Mascarene Archipelago. Journal of ethnopharmacology, 136(3), 525-531. doi: https://doi.org/10.1016/j.jep.2010.06.013
Khorshidian, N., Yousefi, M., Khanniri, E., & Mortazavian, A. M. (2018). Potential application of essential oils as antimicrobial preservatives in cheese. Innovative Food Science & Emerging Technologies, 45, 62–72. doi: https://doi.org/10.1016/j.ifset.2017.09.020
Kubitschek-KM, A. R. J., & Zero, J. M. (2014). Development of jojoba oil (Simmondsia chinensis (Link) CK Schneid.) based nanoemulsions. Lat. Am. J. Pharm, 33(3), 459-63. https://www2.unifap.br/quimica/files/2020/02/Development-of-Jojoba-Oil-Simmondsia-chinensis-Link-C.K.-Schneid.-Based.pdf
Martins, T. G. T., Rosa, P. V. S., de Araújo Neto, A. P., Carvalho, A. M. A. S., da Silva Silveira, L., Neves, I. R., ... & Mouchrek Filho, V. E. (2021). Chemical profile, bactericidal in vitro potential and toxicity against Artemia salina Leach of essential oils obtained from natural condiments. Research, Society and Development, 10(2), e58310212898-e58310212898. doi: https://doi.org/10.33448/rsd-v10i2.12898
McClements, D. J. (2004). Food emulsions: principles, practices, and techniques. Florida (USA): CRC press.
Miguel, M. G. (2010). Antioxidant and anti-inflammatory activities of essential oils: a short review. Molecules, 15(12), 9252-9287. doi: https://doi.org/10.3390/molecules15129252
Mohammadi, S. (2015). The Evaluation of the Analgesic Effects and Acute Toxicity of Methanol Extract of Pimpinella anisum. L in Male Wistar Rats. Journal of Babol University of Medical Sciences, 17(5), 59-65. https://www.researchgate.net/publication/281708623_The_Evaluation_of_the_Analgesic_Effects_and_Acute_Toxicity_of_Methanol_Extract_of_Pimpinella_anisumL_in_Male_Wistar_Rats#full-text
Mssillou, I., Agour, A., El Ghouizi, A., Hamamouch, N., Lyoussi, B., & Derwich, E. (2020). Chemical composition, antioxidant activity, and antifungal effects of essential oil from Laurus nobilis L. flowers growing in Morocco. Journal of Food Quality, 2020(1), 8819311. doi: https://doi.org/10.1155/2020/8819311
Olmedo, R. H., Nepote, V., & Grosso, N. R. (2013). Preservation of sensory and chemical properties in flavoured cheese prepared with cream cheese base using oregano and rosemary essential oils. LWT - Food Science and Technology, 53(2), 409–417. doi: https://doi.org/10.1016/j.lwt.2013.04.007
Ouis, N., & Hariri, A. (2021). Chemical analysis, antioxidant and antibacterial activities of Aniseeds essential oil. Agriculturae Conspectus Scientificus, 86(4), 337-348. https://hrcak.srce.hr/267393
Padmanabhan, P., & Jangle, S. N. (2012). Evaluation of in-vitro anti-inflammatory activity of herbal preparation, a combination of four medicinal plants. International journal of basic and applied medical sciences, 2(1), 109-116. http://cibtech.org/J-MEDICAL-SCIENCES/PUBLICATIONS/2012/JMS-02-01-PDF/22%20JMS%2043%20Preeti%20Padmanabhan.pdf
Patrakar, R., Mansuriya, M., & Patil, P. (2012). Phytochemical and pharmacological review on Laurus nobilis. International journal of pharmaceutical and chemical sciences, 1(2), 595-602. https://api.semanticscholar.org/CorpusID:25417289
Peixoto, L. R., Rosalen, P. L., Ferreira, G. L. S., Freires, I. A., de Carvalho, F. G., Castellano, L. R., & de Castro, R. D. (2017). Antifungal activity, mode of action and anti-biofilm effects of Laurus nobilis Linnaeus essential oil against Candida spp. Archives of oral biology, 73, 179-185. doi: https://doi.org/10.1016/j.archoralbio.2016.10.013
Poprac, P., Jomova, K., Simunkova, M., Kollar, V., Rhodes, C. J., & Valko, M. (2017). Targeting free radicals in oxidative stress-related human diseases. Trends in Pharmacological Sciences, 38(7), 592–607.https://www.cell.com/trends/pharmacological-sciences/abstract/S0165-6147(17)30097-4
Qasim Barkat, M., & Khalid Mahmood, H. (2018). Phytochemical and antioxidant screening of Zingiber officinale, Piper nigrum, Rutag raveolanes, and Carum carvi and their effect on gastrointestinal tract activity. Matrix Science Medica, 2(1), 09–13. doi: http://doi.org/10.26480/MSM.01.2018.09.13
Rebey, I., Bourgou, S., Ben Kaab, S., Aidi Wannes, W., Ksouri, R., Saidani Tounsi, M., & Fauconnier, M. L. (2020). On the effect of initial drying techniques on essential oil composition, phenolic compound and antioxidant properties of anise (Pimpinella anisum L.) seeds. Journal of Food Measurement and Characterization, 14, 220-228. doi: https://doi.org/10.1007/s11694-019-00284-4
Rego, E. A. (2012). Avaliação da actividade anti-inflamatória de plantas dos açores (Master’s thesis, Universidade dos Acores (Portugal)). https://www.proquest.com/openview/36d21f1367aac329137c644cdd42649b/1?pq-origsite=gscholar&cbl=2026366&diss=y
Rodrigues, E. D. C., Ferreira, A. M., Vilhena, J. C., Almeida, F. B., Cruz, R. A., Florentino, A. C., ... & Fernandes, C. P. (2014). Development of a larvicidal nanoemulsion with Copaiba (Copaifera duckei) oleoresin. Revista Brasileira de Farmacognosia, 24, 699-705. doi: https://doi.org/10.1016/j.bjp.2014.10.013
Ru, Q., Hu, Q., Dai, C., Zhang, X., & Wang, Y. (2022). Formulation of Laurus nobilis essential oil nanoemulsion system and its application in fresh-cut muskmelons. Coatings, 12(2), 159. doi: https://doi.org/10.3390/coatings12020159
Séfora-Sousa, M., & Angelis-Pereira, D. (2013). Mecanismos moleculares de ação antiinflamatória e antioxidante de polifenóis de uvas e vinho tinto na aterosclerose. Revista Brasileira de Plantas Medicinais, 15, 617-626. doi: https://doi.org/10.1590/S1516-05722013000400020
Shafiq, S., Shakeel, F., Talegaonkar, S., Ahmad, F. J., Khar, R. K., & Ali, M. (2007). Development and bioavailability assessment of ramipril nanoemulsion formulation. European journal of pharmaceutics and biopharmaceutics, 66(2), 227-243. doi: https://doi.org/10.1016/j.ejpb.2006.10.014
Sırıken, B., Yavuz, C., & Güler, A. (2018). Antibacterial Activity of Laurus nobilis: A review of literature. Medical Science and Discovery, 5(11), 374-379. doi: https://doi.org/10.17546/msd.482929
Smirnoff, N., & Cumbes, Q. J. (1989). Hydroxyl radical scavenging activity of compatible solutes. Phytochemistry, 28(4), 1057-1060. doi: https://doi.org/10.1016/0031-9422(89)80182-7
Sugumar, S., Clarke, S. K., Nirmala, M. J., Tyagi, B. K., Mukherjee, A., & Chandrasekaran, N. (2014). Nanoemulsion of eucalyptus oil and its larvicidal activity against Culex quinquefasciatus. Bulletin of entomological research, 104(3), 393-402. doi: https://doi.org/10.1017/S0007485313000710
Tepe, A. S., & Tepe, B. (2015). Traditional use, biological activity potential and toxicity of Pimpinella species. Industrial Crops and Products, 69, 153-166. doi: https://doi.org/10.1016/j.indcrop.2015.01.069
Van Den Dool, H. A. N. D., & Kratz, P. D. (1963). A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. Journal of chromatography. https://worldveg.tind.io/record/1766/
Vasireddy, L., Bingle, L. E. H., & Davies, M. S. (2018). Antimicrobial activity of essential oils against multidrug-resistant clinical isolates of the Burkholderia cepacia complex. PLOS ONE, 13(8), e0201835. doi: https://doi.org/10.1371/journal.pone.0201835
Vital, A. C. P., Guerrero, A., Monteschio, J. D. O., Valero, M. V., Carvalho, C. B., De Abreu Filho, B. A., Madrona, G. S., & Do Prado, I. N. (2016). Effect of edible and active coating (with rosemary and oregano essential oils) on beef characteristics and consumer acceptability. PLOS ONE, 11(8), e0160535. doi: https://doi.org/10.1371/journal.pone.0160535
Waterhouse, A. L. (2002). Determination of total phenolics. Current protocols in food analytical chemistry, 6(1), I1-1. https://www.researchgate.net/profile/Roberto-Molteni/post/Does_Folin-Ciocalteu_total_phenolic_compound_analysis_include_tannins/attachment/5eaadefff155db0001f88a68/AS%3A886026180521987%401588256511570/download/totalphenolsmethods.pdf
Weidinger, A., & Kozlov, A. V. (2015). Biological activities of reactive oxygen and nitrogen species: Oxidative stress versus signal transduction. Biomolecules, 5(2), 472–484. doi: https://doi.org/10.3390/biom5020472
Zactiti, E. M., & Kieckbusch, T. G. (2006). Potassium sorbate permeability in biodegradable alginate films: Effect of the antimicrobial agent concentration and crosslinking degree. Journal of Food Engineering, 77(3), 462-467. doi: https://doi.org/10.1016/j.jfoodeng.2005.07.015
Zengin, G., Senkardes, I., Mollica, A., Picot-Allain, C. M. N., Bulut, G., Dogan, A., & Mahomoodally, M. F. (2018). New insights into the in vitro biological effects, in silico docking, and chemical profile of clary sage (Salvia sclarea L.). Computational Biology and Chemistry, 75, 111–119. doi: https://doi.org/10.1016/j.compbiolchem.2018.05.005
Zhang, H.-Y. (2005). Structure-activity relationships and rational design strategies for radicalscavenging antioxidants. Current Computer-Aided Drug Design, 1(3), 257–273. https://www.benthamdirect.com/content/journals/cad/10.2174/1573409054367691
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