rccqf Revista Colombiana de Ciencias Químico - Farmacéuticas Rev. colomb. cienc. quim. farm. 0034-7418 Departamento de Farmácia, Facultad de Ciencias, Universidade Nacional da Colombia 10.15446/rcciquifa.v48n1.80067 Artículos de Revisión Essential oils as a source of bioactive molecules Aceites esenciales como fuentes de moléculas bioactivas León-Méndez Glicerio 1 2 * Pájaro-Castro Nerlis 3 Pájaro-Castro Enilson 3 Torrenegra-Alarcon Miladys 1 Herrera-Barros Adriana 4 Faculty of Health Science Corporación Universitaria Rafael Nuñez. Programa de Tecnología de Estética y Cosmetología (GITEC). Cartagena, Bolívar, Colombia. Corporación Universitaria Rafael Núñez Faculty of Health Science Corporación Universitaria Rafael Nuñez Cartagena Bolívar Colombia Doctorate student in Engineering University of Cartagena. Cartagena, Bolívar, Colombia. Universidad de Cartagena University of Cartagena Cartagena Bolívar Colombia Department of Medicine, School of Health Sciences, Medical and Pharmaceutical Sciences Group, University of Sucre, Sincelejo, Sucre 700003. Universidad de Sucre Department of Medicine Medical and Pharmaceutical Sciences Group University of Sucre Sincelejo Sucre Colombia Faculty of Engineering, University of Cartagena, Research in Multi-functional Nanomaterials Group, Cartagena, Bolívar 130015. Universidad de Cartagena Faculty of Engineering University of Cartagena Cartagena Bolívar Colombia Email : gleonm1@unicartagena.edu.co

Este es un artículo publicado en acceso abierto bajo una licencia Creative Commons

 Jan-Apr 2019 48 1 80 93 31 05 2018 26 11 2018 This is an open-access article distributed under the terms of the Creative Commons Attribution License SUMMARY

Nature gives us a large number of compounds with interesting biological properties, within them we have essential oils, which are an important source of new bioactive molecules, which can replace synthetic chemicals, since they are friendly to the environment and they are less toxic. Currently there are more than 20.000 publications in which essential oils are related to some biological activity, according to the search made in different databases until January 2018. This confirms the wide utility of essential oils as the main source of bioactive metabolites, which can be used in different areas of our life.

 RESUMEN

La naturaleza nos proporciona una gran cantidad de compuestos con interesantes propiedades biológicas, dentro de los cuales tenemos los aceites esenciales, los cuales son una fuente importante de nuevas moléculas bioactivas, que pueden reemplazar a los químicos sintéticos, ya que son amigables con el medio ambiente y son menos tóxicos. Actualmente existen más de 20.000 publicaciones en las que los aceites esenciales están relacionados con alguna actividad biológica, según la búsqueda realizada en diferentes bases de datos hasta enero de 2018. Esto confirma la amplia utilidad de los aceites esenciales como principal fuente de metabolitos bioactivos, que pueden ser utilizados en diferentes áreas de nuestra vida.

 <italic>Keywords:</italic> Natural products plants terpenes volatile compounds biological activity phenylpropanes <italic>Palabras clave:</italic> Productos naturales plantas terpenos compuestos volátiles actividad biológica fenipronanos INTRODUCTION

Essential oils (EOs) are complex mixtures of volatile organic compounds produced in the form of secondary metabolites in plants that can contain about 20-60 components in very different concentrations [1,2]. They are characterized because they contain two or three main components in relatively high concentrations (20-70%) compared to other components present in minimal amounts [3]. They may consist of monoterpenes, sesquiterpenes, and phenylpropanes, which may contain different functional groups (alkanes, alcohols, aldehydes, ketones, esters and acids) [1,2].

In nature, EOs plays an important role in the protection of plants such as antibacterial, antiviral, antifungal, insecticide and also against herbivores, reducing their appetite for these plants. They are also responsible for the characteristic smell of plants, which can attract some insects to favor the dispersal of pollen and seeds, or repel other undesirable ones [3]. Around 3000 of the essential oils are known and 10% of them having commercial importance in the cosmetic, food and pharmaceutical industries, and in agriculture [3,4]. Therefore, they are generally recognized as safe by the FDA (Food and Drug Administration). Its composition can vary considerably between species of aromatic plants and varieties and within the same variety of different geographical areas [1].

 METHODOLOGY

An exhaustive search was carried out in PubMed, Scopus, Google scholar and SciELO databases to find an article that related the different biological activities of essential oils and their components. The search was conducted until January 2018. A text-mining step was carried out in order to detect citation-associated relationships between essential oils and several biological activities. Taking into account the dates of publication and the country of origin.

These keywords were recognized through literature reviews using a wide variety of academic databases and search engines available online, such as GoPubmed (http://gopubmed.org/web/gopubmed/), pubGraph (http://datamining.cs.ucla.edu/cgi-bin/pubgraph.cgi), and Helioblast (http://helioblast.heliotext.com/) and the analysis of associations among these terms was done in the PubMed/Medline literature database was carried out using the Jaccard co-occurrence score, as a measure of the degree to which the two queries coincide among all publications. The information obtained was organized in order to identify the reported biological activity, the essential oil responsible for the activity and the biologically active concentration.

 RESULTS Bioactivity of essential oils

The EOs has a wide application in pharmacology (see figure 1), especially for their antimicrobial properties [5, 6], the hydrocarbon and oxygenated monoterpenes are able to destroy the cellular integrity and therefore inhibit respiration and transport of ions [7]. The terpenes; Pine, myrcene, limonene, Ocimene, linalool, and verbenum are related to the antimicrobial activity of the essential oil of Bidens pilosa [7]. Essential oils with an abundance of phenylpropanoids and phenols inhibit platelet aggregation. The α-terpineol has cytotoxic properties, D-limonene, anticancer in male rats [1], perillic alcohol used in the treatment of different types of cancer, which is found in Phase I and II clinical studies [8], antiseptic, anti-inflammatory, antioxidant, antifungal, anti-depressant, aphrodisiac and other properties present in a greater or lesser degree in all oils [1,3,9,10]. They are also used for their relaxing or stimulating effects on the Central Nervous System, bronchial, urinary infections and those caused by cuts and burns [3, 11].

Many studies carried out with essential oils have reported that they have a broad microbiological activity such as: antifungal [12], antibacterial [13-15], acaricide [16], insecticide [17,18], antimalarial [19], quorum sensing [20], and antiviral [21]. They also have properties such as: analgesics [7], antipyretics [22], anti-inflammatories [7,23], anticonvulsants [24], as an estrogenic agent [25], hepatoprotective [26], anticancer [27] and antimutagenic [28]. They are also used in the treatment of gastric ulcer and different types of cancer [3].

The EOs has shown antiviral activity against species of the Flavivirus genus. In fact, it has been shown that the EOs of Lippia origanoides, Oreganum vulgare, Lippia alba and Artemisia vulgaris have an antiviral effect against the yellow fever virus [29]. Nowadays, there are reports of the antiviral activity of essential oils against the dengue virus. Authors such as Pájaro-Castro et al. [30], Ocazionez et al. [31], Meneses et al. [32], Meneses et al. [33], Duschatzky et al. [34] and García et al. [35] has revealed the antiviral properties of these natural products. In the field of agriculture, EOs have been recognized for their repellent activity [36, 37], insecticide and fumigant [38-40]. Neiro et al., [1] reported more than 80 different essential oils families with repellent activity for arthropod species.

Taking into account that essential oils are complex mixtures of many molecules, it is important to establish if the biological activities identified in them are due to a single component or several of them, that is, if their biological effects are the result of a synergy of all the molecules or if they reflect only the main molecules present at the highest levels according to the gas chromatography analysis [1,2]. The studies found in the literature generally do not answer this question. In general, it is found that the main components reflect fairly well the biological characteristics of the essential oils from which they were isolated, and their effects depend only on their concentration when each component is analyzed independently or in some cases of the mixture. Therefore, it is possible that the activity of the main components is modulated by other molecules that are in lower concentration in the essential oil. In that sense, for biological purposes, it is more informative to study a complete essential oil instead of some of its components because the concept of synergy seems to be more significant [3].

In the search carried out using the keyword essential oils, 73814 articles were observed until 2018. An increase in the number of public articles was observed, being 929 in the year 1994, this value has been increased every year until 5853 in the year 2017 and 1524 until January 2018. The journals that have most published articles related to essential oils are: Food Chemistry (1746), Journal of Chromatography A. (1350), Industrial Crops and Products (1307) and Phytochemistry (1159).

When the search was carried out using the keywords essential oils and biological activity, 27.021 articles published up to 2018 were found, as well as an increase in the number of publications each year, being 319 for the year 1994 and 2656 for the year 2017, being 713 publications so far in 2018. Table 1 shows some of the essential oils with their concentrations reported with some biological activity worldwide. Taking into account the Jaccard co-occurrence e (-1.0), there is a clear association between the essential oils and the different biological activities reported. The main journals that have published an article with these two key words were: Food Chemistry (643), Industrial Crops and Products (625), Journal of Ethnopharmacology (549), Journal of Chromatography A (434), Food and Chemical Toxicology (375) and Phytochemistry (326).

Biological activities reported for essential oils.

General considerations

According to the bibliographic search carried out, essential oils are an important and rich source of bioactive molecules, which can be used in different fields of pharmaceutical sciences. In fact, many of these studies are focused on evaluating the phytochemical profile of a particular essential oil. The main biological activity attributable to essential oils is the antioxidant activity with 17846 reports (24.2%) until January 2018. In these studies, this activity has been reported in more than 100 essential oils from different plant species.

Essential oils with their concentrations reported with some biological activity.

The second biological activity that has been most reported for essential oils is the antimicrobial activity with 8815 (11.9%), followed by insecticidal and repellent activity with 7827 (10.6%), and the least reported activities are anticancer, estrogen, hepatoprotective, anticonvulsant, antimutagenic, antiviral, antipyretic, acaricide, antinoceptive, antitripanosomal, anti-inflammatory activity, from major to minor.

The above indicates the great potential of essential oils as sources of bioactive molecules, however it is important to consider the complex chemical composition of these natural products, and the interaction of these to have a certain activity. So, the mechanism of action of essential oils is difficult to understand and in some cases is not completely elucidated. In fact, it has been reported that some essential oils have a synergistic effect [44-49]. An example of this is the use of essential oils in the development of biopesticides with different mechanisms of action and that often exhibit mutual synergistic relationships, which can be effective in preventing the development of populations of pathogens and resistant pests. However, it is important to establish relationships between individual substances in EOs and the effects of sublethal concentrations in white and non-white organisms [50]. In addition, essential oils are very useful, although it is a challenge to identify if a certain action is by individual components or by mixtures of them, as well as to elucidate their mechanism of action.

 CONCLUSIONS

In summary, EOs are an excellent source of metabolites with a wide range of bioactive molecules that can be used in different areas of our lives, because they have been shown to be safe for humans and the environment.

 ACKNOWLEDGMENTS

The authors thank at the University of Sucre, University of Cartagena and Center of Commerce and Services, Regional Bolivar, SENA

 REFERENCES 1. L. Neiro, J. Olivero, E. Stashenko. Repellent activity of essential oils: A review, Bioresour. Technol. 101(1), 372-378 (2010). Neiro L Olivero J Stashenko E Repellent activity of essential oils: A review Bioresour. Technol 101 1 372 378 2010 2. A. Martínez, Aceites esenciales. Universidad de Antioquia (2001). Available in: Available in: http://farmacia.udea.edu.co/~ff/esencias2001b.pdf , Accessed December 17, 2011. Martínez A Aceites esenciales Universidad de Antioquia 2001 Available in: http://farmacia.udea.edu.co/~ff/esencias2001b.pdf December 17, 2011 3. F. Bakkali, S. Averbeck, D. Averbeck, M. Idaomar, Biological effects of essential oils. A review, Food Chem. Toxicol ., 46(2), 446-475 (2008). Bakkali F Averbeck S Averbeck D Idaomar M Biological effects of essential oils. A review Food Chem. Toxicol 46 2 446 475 2008 4. G. Sacchetti, S. Maietti, M. Muzzoli, M. Scaglianti, S. Manfredini, M. Radice, R. Bruni, Comparative evaluation of 11 essential oils of different origin as functional antioxidants, antiradicals and antimicrobials in foods, Food Chem ., 91(4), 621-632 (2005). Sacchetti G Maietti S Muzzoli M Scaglianti M Manfredini S Radice M Bruni R Comparative evaluation of 11 essential oils of different origin as functional antioxidants, antiradicals and antimicrobials in foods Food Chem 91 4 621 632 2005 5. G. Lee, Y. Kim, H. Kim, L.R. Beuchat, J.H. Ryu, Antimicrobial activities of gaseous essential oils against Listeria monocytogenes on a laboratory medium and radish sprouts, Int. J. Food Microbiol ., 265, 49-54 (2018). Lee G Kim Y Kim H Beuchat L.R Ryu J.H Antimicrobial activities of gaseous essential oils against Listeria monocytogenes on a laboratory medium and radish sprouts Int. J. Food Microbiol 265,49 54 2018 6. J. Martínez, B. Sulbarán, J. Ojeda, A. Ferrer, R. Nava, Actividad antimicrobiana del aceite esencial de la mandarina, Rev. Fac. Agronom ., 20, 502-512 (2003). Martínez J Sulbarán B Ojeda J Ferrer A Nava R Actividad antimicrobiana del aceite esencial de la mandarina Rev. Fac. Agronom 20,502 512 2003 7. F. Deba, T. Xuan, M. Yasuda, S. Tawata, Chemical composition and antioxidant, antibacterial and antifungal activities of the essential oils from Bidens pilosa Linn. var. Radiata, Food Control, 19(4),346-352 (2008). Deba F Xuan T Yasuda M Tawata S Chemical composition and antioxidant, antibacterial and antifungal activities of the essential oils from Bidens pilosa Linn. var. Radiata Food Control 19 4 346 352 2008 8. H. Bailey, D. Levy, L. Harris, J. Schink, F. Foss, P. Beatty, S. Wadler, A Phase II Trial of Daily Perillyl ACLohol in Patients with Advanced Ovarian Cancer: Eastern Cooperative Oncology Group Study E2E96, Gynecol. Oncol ., 85(3), 464-468 (2002). Bailey H Levy D Harris L Schink J Foss F Beatty P Wadler S Phase A II Trial of Daily Perillyl ACLohol in Patients with Advanced Ovarian Cancer: Eastern Cooperative Oncology Group Study E2E96 Gynecol. Oncol 85 3 464 468 2002 9. M. Osorio-Fortich, G. Matiz-Melo, G. León-Méndez, D. López-Olivares, N. Pájaro-Castro, Evaluación de la acción antiséptica de un jabón líquido utilizando algunos aceites esenciales como agente activo, Rev. Colomb. Cienc. Quím. Farm ., 46(2),176-187 (2017). Osorio-Fortich M Matiz-Melo G León-Méndez G López-Olivares D Pájaro-Castro N Evaluación de la acción antiséptica de un jabón líquido utilizando algunos aceites esenciales como agente activo Rev. Colomb. Cienc. Quím. Farm 46 2 176 187 2017 10. G. León-Méndez, M. Osorio Fortich, M. Torrenegra-Alarcón, J. Gil, Extraction, characterization and antioxidant activity of essential oil from Plectranthus amboinicus L., Rev. Cubana Farm ., 49, 4 (2015). León-Méndez G Osorio Fortich M Torrenegra-Alarcón M Gil J Extraction, characterization and antioxidant activity of essential oil from Plectranthus amboinicus L Rev. Cubana Farm 49,4 2015 11. D. Marcano, M. Hasegawa, Aceites esenciales. En: "Fitoquímica orgánica". Editorial Torino. Segunda edición. Venezuela, Caracas, 2002, pp. 237-317. Marcano D Hasegawa M Aceites esenciales Fitoquímica orgánica Editorial Torino Segunda edición Venezuela, Caracas 2002 237 317 12. S. Juglal, R. Govinden, B. Odhav. Spice oils for the control of co-occurring mycotoxin-producing fungi, J. FoodProt ., 65(4), 683-687 (2002). Juglal S Govinden R Odhav B Spice oils for the control of co-occurring mycotoxin-producing fungi J. FoodProt 65 4 683 687 2002 13. M. Torrenegra-Alarcón, N. Pájaro-Castro, G. León-Méndez, Actividad antibacteriana in vitro de aceites esenciales de diferentes especies del género Citrus, Rev. Colomb. Cienc. Quim. Farm ., 46(2), 160-175 (2017). Torrenegra-Alarcón M Pájaro-Castro N León-Méndez G Actividad antibacteriana in vitro de aceites esenciales de diferentes especies del género Citrus Rev. Colomb. Cienc. Quim. Farm 46 2 160 175 2017 14. M. Torrenegra-Alarcón, C. Granados-Conde, M. Durán-Lengua, G. León-Méndez, X. Yáñez-Rueda, C. Martínez, N. Pájaro-Castro, The chemical composition and antibacterial activity of essential oil from Minthostachys mollis, Orinoquia 20(1), 69-74 (2016). Torrenegra-Alarcón M Granados-Conde C Durán-Lengua M León-Méndez G Yáñez-Rueda X Martínez C Pájaro-Castro N The chemical composition and antibacterial activity of essential oil from Minthostachys mollis Orinoquia 20 1 69 74 2016 15. G. Matiz-Melo, G. León-Méndez, M. Osorio Fortich, In vitro antibacterial activity of nineteen essential oils against acne-associated bacteria, Rev. Cubana Farm ., 49, 1 (2015). Matiz-Melo G León-Méndez G Osorio Fortich M In vitro antibacterial activity of nineteen essential oils against acne-associated bacteria Rev. Cubana Farm 49,1 2015 16. F.M. Ferreira, C.C. Delmonte, T.L.P. Novato, C.M.O. Monteiro, E. Daemon, F. M.P. Vilela, M.P.H. Amaral, Acaricidal activity of essential oil of Syzygium aromaticum, hydrolate and eugenol formulated or free on larvae and engorged females of Rhipicephalus microplus, Med. Vet. Entomol ., 32(1), 41-47 (2018). Ferreira F.M Delmonte C.C Novato T.L.P Monteiro C.M.O Daemon E Vilela F. M.P Amaral M.P.H Acaricidal activity of essential oil of Syzygium aromaticum, hydrolate and eugenol formulated or free on larvae and engorged females of Rhipicephalus microplus Med. Vet. Entomol 32 1 41 47 2018 17. A.K. Tripathi, V. Prajapati, N. Verma, J.R. Bahl, R. Bansal, S. Khanuja, S. Kumar, Bioactivities of the leaf essential oil of Curcuma longa (var. ch-66) on three species of stored-product beetles (Coleoptera), J. Econ. Entomol ., 95(1), 183-189 (2002). Tripathi A.K Prajapati V Verma N Bahl J.R Bansal R Khanuja S Kumar S Bioactivities of the leaf essential oil of Curcuma longa (var. ch-66) on three species of stored-product beetles (Coleoptera) J. Econ. Entomol 95 1 183 189 2002 18. E. Enan, Insecticidal activity of essential oils: octopaminergic sites of action, Comp. Biochem. Physiol. C Toxicol. Pharmacol ., 130(3), 325-337 (2001). Enan E Insecticidal activity of essential oils: octopaminergic sites of action Comp. Biochem. Physiol. C Toxicol. Pharmacol 130 3 325 337 2001 19. S. Kpoviessi, J. Bero, P. Agbani, F. Gbaguidi, B. Kpadonou-Kpoviessi, B. Sinsin, G. Accrombessi, M. Frédérich, M. Moudachirou, J. Quetin-Leclercq, Chemical composition, cytotoxicity and in vitro antitrypanosomal and antiplasmodial activity of the essential oils of four Cymbopogon species from Benin, J. Eth-nopharmacol., 151(1), 652-659 (2014). 151 20. J. Olivero-Verbel, N. Pájaro-Castro, E. Stashenko, Actividad antiquórum sensing de aceites esenciales aislados de diferentes especies del género Piper, Vitae, 18(1), 77-82 (2011). 18 21. P. Schnitzler, K. Schon, J. Reichling, Antiviral activity of Australian tea tree oil and Eucalyptus oil against herpes simplex virus in cell culture, Pharmazie, 56(4), 343-347 (2001). 56 22. R. Kumar, P. Om, K.P. Anil, K. Mahesh, A.I. Valary, S. Lech, Chemical composition and antiinflammatory, anti-nociceptive and antipyretic activity of rhizome essential oil of Globba sessiliflora Sims. collected from Garhwal region of Uttarakhand, Int. J. Herb. Med ., 8(1), 59-69 (2017). Kumar R Om P Anil K.P Mahesh K Valary A.I Lech S Chemical composition and antiinflammatory, anti-nociceptive and antipyretic activity of rhizome essential oil of Globba sessiliflora Sims. collected from Garhwal region of Uttarakhand Int. J. Herb. Med 8 1 59 69 2017 23. J. Grassmann, S. Hippeli, K. Dornisch, U. Rohnert, N. Beuscher, E.F. Elstner, Antioxidant properties of essential oils. Possible explanations for their antiin-flammatory effects, Arzneimittelforschung, 50(2), 135-139 (2000). Grassmann J Hippeli S Dornisch K Rohnert U Beuscher N Elstner E.F Antioxidant properties of essential oils. Possible explanations for their antiin-flammatory effects Arzneimittelforschung 50 2 135 139 2000 24. M. Sayyah, J. Valizadeh, M. Kamalinejad, Anticonvulsant activity of the leaf essential oil of Laurus nobil against pentylenetetrazole and maximal electros-hock-induced seizures, Phytomedicine, 9(3), 212-216 (2002). Sayyah M Valizadeh J Kamalinejad M Anticonvulsant activity of the leaf essential oil of Laurus nobil against pentylenetetrazole and maximal electros-hock-induced seizures Phytomedicine 9 3 212 216 2002 25. N. Tabanca, S.I. Khan, E. Bedir, S. Annavarapu, K. Willett, I.A. Khan, N. Kirimer, K.H. Baser, Estrogenic activity of isolated compounds and essential oils of Pimpinella species from Turkey, evaluated using a recombinant yeast screen, Planta Med ., 70(8), 728-735 (2004). Tabanca N Khan S.I Bedir E Annavarapu S Willett K Khan I.A Kirimer N Baser K.H Estrogenic activity of isolated compounds and essential oils of Pimpinella species from Turkey, evaluated using a recombinant yeast screen Planta Med 70 8 728 735 2004 26. K. Bellassoued, A. Ben Hsouna, K. Athmouni, J. van Pelt, F. Makni Ayadi, T. Rebai, A. Elfeki, Protective effects of Mentha piperita L. leaf essential oil against CCl4 induced hepatic oxidative damage and renal failure in rats, Lipids Health Dis ., 17(1), 9 (2018). Bellassoued K Ben Hsouna A Athmouni K van Pelt J Makni Ayadi F Rebai T Elfeki A Protective effects of Mentha piperita L. leaf essential oil against CCl4 induced hepatic oxidative damage and renal failure in rats Lipids Health Dis 17 1 9 9 2018 27. L. Pudziuvelyte, M. Stankevicius, A. Maruska, V. Petrikaite, O. Ragazinskiene, G. Draksiene, J. Bernatoniene, Chemical composition and anticancer activity of Elsholtzia ciliata essential oils and extracts prepared by different methods, Ind. Crops Prod ., 107, 90-96 (2017). Pudziuvelyte L Stankevicius M Maruska A Petrikaite V Ragazinskiene O Draksiene G Bernatoniene J Chemical composition and anticancer activity of Elsholtzia ciliata essential oils and extracts prepared by different methods Ind. Crops Prod 107,90 96 2017 28. J.D. Toscano-Garibay, M. Arriaga-Alba, J. Sánchez-Navarrete, M. Mendoza-García, J.J. Flores-Estrada, M.A. Moreno-Eutimio, J.J. Espinosa-Aguirre, M. González-Ávila, N.J. Ruiz-Pérez, Antimutagenic and antioxidant activity of the essential oils of Citrus sinensis and Citrus latifolia, Sci. Rep ., 7, 11479 (2017). Toscano-Garibay J.D Arriaga-Alba M Sánchez-Navarrete J Mendoza-García M Flores J.J Moreno-Eutimio M.A Espinosa-Aguirre J.J González-Ávila M Ruiz-Pérez N.J Antimutagenic and antioxidant activity of the essential oils of Citrus sinensis and Citrus latifolia Sci. Rep 7,11479 11479 2017 29. R. Meneses, R. Ocazionez, J. Martínez, Inhibitory effect of essential oils obtained from plants grown in Colombia on yellow fever virus replication in vitro, Ann. Clin. Microbiol. Antimicrob ., 8, 8 (2009). Meneses R Ocazionez R Martínez J Inhibitory effect of essential oils obtained from plants grown in Colombia on yellow fever virus replication in vitro Ann. Clin. Microbiol. Antimicrob 8,8 2009 30. N. Pájaro-Castro, M. Flechas, R. Ocazionez, E. Stashenko, J. Olivero-Verbel, Potential interaction of components from essential oils with dengue virus proteins, Blacpma, 14(3),141-155 (2015). Pájaro-Castro N Flechas M Ocazionez R Stashenko E Olivero-Verbel J Potential interaction of components from essential oils with dengue virus proteins Blacpma 14 3 141 155 2015 31. R. Ocazionez, R. Meneses, F. Torres, E. Stashenko, Virucidal activity of Colombian Lippia essential oils on dengue virus replication in vitro, Mem. Inst. Oswaldo Cruz (Rio de Janeiro), 105(3), 304-309 (2010). Ocazionez R Meneses R Torres F Stashenko E Virucidal activity of Colombian Lippia essential oils on dengue virus replication in vitro Mem. Inst. Oswaldo Cruz (Rio de Janeiro) 105 3 304 309 2010 32. R. Meneses, F. Torres, E. Stashenko, R. Ocazionez, Aceites esenciales de plantas colombianas inactivan el virus del dengue y el virus de la fiebre amarilla, Rev. Univ. Ind. Santander Salud, 41, 236-243 (2009). Meneses R Torres F Stashenko E Ocazionez R Aceites esenciales de plantas colombianas inactivan el virus del dengue y el virus de la fiebre amarilla Rev. Univ. Ind. Santander Salud 41,236 243 2009 33. R. Meneses, F. Torres, E. Stashenko, R. Ocazionez, Essentials oils from seven aromatic plants grown in Colombia: Chemical composition, cytotoxicity and in vitro virucidal effect on the dengue virus, Int. J. Essent. Oil Ther ., 3, 1-7 (2009). Meneses R Torres F Stashenko E Ocazionez R Essentials oils from seven aromatic plants grown in Colombia: Chemical composition, cytotoxicity and in vitro virucidal effect on the dengue virus Int. J. Essent. Oil Ther 3,1 7 2009 34. C. Duschatzky, M. Possetto, L. Talarico, C. García, F. Michis, N. Almeida, M. Lampasona, C. Schuff, E. Damonte, Evaluation of chemical and antiviral properties of essential oils from South American plants, Antivir. Chem. Chemother ., 16(4), 247-251 (2005). Duschatzky C Possetto M Talarico L García C Michis F Almeida N Lampasona M Schuff C Damonte E Evaluation of chemical and antiviral properties of essential oils from South American plants Antivir. Chem. Chemother 16 4 247 251 2005 35. C.C. García, L. Talarico, N. Almeida, S. Colombres, C. Duschatzky, E.B. Damonte, Virucidal Activity of Essential Oils from Aromatic Plants of San Luis, Argentina, Phytother. Res ., 17(9), 1073-1075 (2003). García C.C Talarico L Almeida N Colombres S Duschatzky C Damonte E.B Virucidal Activity of Essential Oils from Aromatic Plants of San Luis, Argentina Phytother. Res 17 9 1073 1075 2003 36. N. Pájaro-Castro, K. Caballero-Gallardo, J. Olivero-Verbel, Neurotoxic Effects of Linalool and β-Pinene on Tribolium castaneum Herbst, Molecules, 22, 2052 (2017). Pájaro-Castro N Caballero-Gallardo K Olivero-Verbel J Neurotoxic Effects of Linalool and β-Pinene on Tribolium castaneum Herbst Molecules 22,2052 2052 2017 37. K. Caballero-Gallardo, N. Pino-Benitez, N. Pájaro-Castro, E. Stashenko, J. Olivero-Verbel, Plants cultivated in Choco, Colombia, as source of repellents against Tribolium castaneum (Herbst), J. Asia Pac. Entomol ., 17(4), 753-759 (2014). Caballero-Gallardo K Pino-Benitez N Pájaro-Castro N Stashenko E Olivero-Verbel J Plants cultivated in Choco, Colombia, as source of repellents against Tribolium castaneum (Herbst) J. Asia Pac. Entomol 17 4 753 759 2014 38. A. Nascimento, C. Camara, M. Moraes, Actividad fumigante de los aceites esenciales de Schinus terebinthifolius y sus componentes seleccionados frente a Rhyzopertha dominica, Rev. Fac. Nac. Agronom. (Medellín), 71(1), 8359-8366 (2018). Nascimento A Camara C Moraes M Actividad fumigante de los aceites esenciales de Schinus terebinthifolius y sus componentes seleccionados frente a Rhyzopertha dominica Rev. Fac. Nac. Agronom. (Medellín) 71 1 8359 8366 2018 39. J. Sriti Eljazi, O. Bachrouch, N. Salem, K. Msaada, J. Aouini, M. Hammami, E. Boushih, M. Abderraba, F. Liman, J. Mediouni., Chemical composition and insecticidal activity of essential oil from Coriander fruit against Tribolium castae-num, Sitophilus oryzae, and Lasioderma serricorne, Int. J. Food Prop ., 1, 13 (2018). Sriti Eljazi J Bachrouch O Salem N Msaada K Aouini J Hammami M Boushih E Abderraba M Liman F Mediouni J Chemical composition and insecticidal activity of essential oil from Coriander fruit against Tribolium castae-num, Sitophilus oryzae, and Lasioderma serricorne Int. J. Food Prop 1,13 2018 40. R. Hernandez-Lambraño, N. Pájaro-Castro, K. Caballero-Gallardo, E. Stashenko, J. Olivero-Verbel, Essential oils from plants of the genus Cymbopogon as natural insecticides to control stored product pests, J. Stored Prod. Res ., 62, 81-83 (2015). Hernandez-Lambraño R Pájaro-Castro N Caballero-Gallardo K Stashenko E Olivero-Verbel J Essential oils from plants of the genus Cymbopogon as natural insecticides to control stored product pests J. Stored Prod. Res 62,81 83 2015 41. K. Caballero-Gallardo, J. Olivero-Verbel, E. Stashenko, Repellent Activity of Essential Oils and Some of Their Individual Constituents against Tribolium cas-taneum Herbst, J Agric. Food Chem ., 59(5), 1690-1696 (2011). Caballero-Gallardo K Olivero-Verbel J Stashenko E Repellent Activity of Essential Oils and Some of Their Individual Constituents against Tribolium cas-taneum Herbst J Agric. Food Chem 59 5 1690 1696 2011 42. W. Wanzala, A. Hassanali, W. Mukabana, W. Takken, Repellent Activities of Essential Oils of Some Plants Used Traditionally to Control the Brown Ear Tick, Rhipicephalus appendiculatus, J. Parasitol. Res ., 2014, 434-506 (2014). Wanzala W Hassanali A Mukabana W Takken W Repellent Activities of Essential Oils of Some Plants Used Traditionally to Control the Brown Ear Tick, Rhipicephalus appendiculatus J. Parasitol. Res 2014,434 506 2014 43. A.M.D. Nascimento, T.D.S. Maia, T.E.S. Soares, L.R.A. Meneses, R. Scher, E.V. Costa, S.C.H. Cavlacanti, R. La Corte, Repellency and Larvicidal Activity of Essential oils from Xylopia laevigata, Xylopia frutescens, Lippia pedunculosa, and Their Individual Compounds against Aedes aegypti Linnaeus, Neotrop. Entomol ., 46(2), 223-230 (2017). Nascimento A.M.D Maia T.D.S Soares T.E.S Meneses L.R.A Scher R Costa E.V Cavlacanti S.C.H La Corte R Repellency and Larvicidal Activity of Essential oils from Xylopia laevigata, Xylopia frutescens, Lippia pedunculosa, and Their Individual Compounds against Aedes aegypti Linnaeus Neotrop. Entomol 46 2 223 230 2017 44. J. Rivera, P. Crandall, C. O'Bryan, S. Ricke, Essential oils as antimicrobials in food systems. A review, Food Control, 54, 111-119 (2015). Rivera J Crandall P O'Bryan C Ricke S Essential oils as antimicrobials in food systems. A review Food Control 54,111 119 2015 45. C. Granados, Y. Yáñez, G. Santafé, Evaluación de la actividad antioxidante del aceite esencial foliar de Calycolpus moritzianus y Minthostachys mollis de Norte de Santander, Bistua, Rev. Fac. Cienc. Bas ., 10(1), 12-23 (2012). Granados C Yáñez Y Santafé G Evaluación de la actividad antioxidante del aceite esencial foliar de Calycolpus moritzianus y Minthostachys mollis de Norte de Santander, Bistua Rev. Fac. Cienc. Bas 10 1 12 23 2012 46. G. León, M.R. Osorio, S.R. Martínez, Comparación de dos métodos de extracción del aceite esencial de Citrus Sinensis L., Rev. Cubana Farm ., 49(4), 742-750 (2015). León G Osorio M.R Martínez S.R Comparación de dos métodos de extracción del aceite esencial de Citrus Sinensis L Rev. Cubana Farm 49 4 742 750 2015 47. G.E. Matiz-Melo, K.F. Fuentes-López, G. León-Méndez, Microencapsulación de aceite esencial de tomillo (Thymus vulgaris) en matrices poliméricas de almidón de ñame (Dioscorea rotundata) modificado, Rev. Colomb. Cienc. Quím. Farm ., 44(2), 189-207 (2015). Matiz-Melo G.E Fuentes-López K.F León-Méndez G Microencapsulación de aceite esencial de tomillo (Thymus vulgaris) en matrices poliméricas de almidón de ñame (Dioscorea rotundata) modificado Rev. Colomb. Cienc. Quím. Farm 44 2 189 207 2015 48. M. Torrenegra, G. Matiz, G. León, J. Gil, Actividad antibacteriana in vitro de aceites esenciales frente a microorganismos implicados en el acné, Rev. Cubana Farm., 49(3), 512-523 (2015). Torrenegra M Matiz G León G Gil J Actividad antibacteriana in vitro de aceites esenciales frente a microorganismos implicados en el acné Rev. Cubana Farm 49 3 512 523 2015 49. M. Torrenegra, C. Granados, M. Osorio, G. León, Method comparison of hydrodistillation microwave radiation-assisted (MWHD) front hydrodistillation (HD) in the extraction of essential oil of Minthostachys mollis, Inf. Tecnol ., 26(1), 117-122 (2015). Torrenegra M Granados C Osorio M León G Method comparison of hydrodistillation microwave radiation-assisted (MWHD) front hydrodistillation (HD) in the extraction of essential oil of Minthostachys mollis Inf. Tecnol 26 1 117 122 2015 50. R. Pavela, G. Benelli, Essential Oils as Ecofriendly Biopesticides ? Challenges and Constraints, Trends Plant Sci ., 21(12), 1000-1007 (2016). Pavela R Benelli G Essential Oils as Ecofriendly Biopesticides ? Challenges and Constraints Trends Plant Sci 21 12 1000 1007 2016

No potential conflict of interest was reported by the authors.

G. León-Méndez, N. Pájaro-Castro, E. Pájaro-Castro, M. Torrenegra-Alarcón, A. Herrera-Barros, Essential oils as a source of bioactive molecules, Rev. Colomb. Cienc. Quím. Farm., 48(1), 80-93 (2019).