Essential oils are biosynthesized in the secondary metabolism of aromatic medicinal plants and stored in specific structures (Feijó et al.; Cunha., 2012). Many of them have different pharmacological properties due to the content of various bioactive compounds, some of which have potent antioxidant and anti-inflammatory effects (Avola., 2020; Ferreira, 2014).

Due to their physicochemical characteristics such as volatility and lipophilicity, the application of essential oils becomes limited, thus encapsulation systems that provide protection to these compounds can act by improving stability, dispersion and even the activity of essential oils (Asbahani et al., 2015). Among emulsions, nanoemulsions stand out for being systems with particle sizes between 20 and 100 nm, with greater stability to separation and coalescence than conventional emulsions (Mcclements, 2004).

The interest in investigating plants with anti-inflammatory and antioxidant activity lies in the fact that they have a wide application in various pathological processes. This research has opened multiple opportunities for therapeutic intervention (Ferreira, 2014).

Among the aromatic plants, Pimpinella anisum (anise) and Laurus nobilis (laurel) are widely used as condiments in domestic preparations, in folk medicine and by the food, cosmetics and pharmaceutical industries (Patrakar; Mansuriya; Patil, 2012; Tepe, 2015). They stand out for presenting biological activity, namely: antioxidant, antimicrobial, antifungal, anti-inflammatory and analgesic activities (Fernández et al., 2018; Ercin et al., 2022; Siriken et al., 2018; Mohammadi et al., 2015; Iannarelli, R. et al., 2018).

Essential oils (EOs), derived from various parts of aromatic plants, are composed of a wide range of volatile, low molecular weight secondary metabolites. These compounds have garnered significant scientific interest due to their multiple applications in the cosmetic, pharmaceutical, and food industries (Zengin et al., 2018; Dhara & Tripathi, 2013; Vasireddy et al., 2018; Khorshidian et al., 2018). Among the diverse biological properties attributed to these compounds, antioxidant activity stands out as one of the most relevant, representing a significant fraction of the chemical composition of EOs (Miguel, 2010).

The biological importance of natural antioxidants is intrinsically linked to their ability to counteract oxidative stress. This physiological imbalance occurs when there is a disruption in the pro-oxidant/antioxidant equilibrium, leading to an increased production of Reactive Oxygen Species (ROS) – such as alkoxyl (RO•), superoxide anion (O2•-), hydroxyl (HO•), and peroxyl (RO2•) radicals – and Reactive Nitrogen Species (RNS), such as nitric oxide (NO•) and peroxynitrite (ONOO−) (Poprac et al., 2017; Weidinger & Kozlov, 2015). Oxidative stress is implicated in the pathogenesis of various human diseases, including neurodegenerative disorders like Alzheimer’s and cancer (Poprac et al., 2017).

In this context, bioactive compounds present in condiment and aromatic plants are considered promising sources of natural antioxidants capable of preventing or mitigating damage induced by oxidative stress (Qasim Barkat & Khalid Mahmood, 2018). The antioxidant activity of many of these compounds, such as thymol, carvacrol, menthol, eucalyptol, and eugenol, is often related to the presence of hydroxyl groups in their chemical structures, which act as electron donors to neutralize free radicals (Zhang, 2005). Ongoing investigation into these compounds not only validates their traditional uses but also paves the way for the development of novel pharmaceutical, cosmetic, and food applications, offering a natural alternative to synthetic antioxidants, which may pose adverse health effects (Vital et al., 2016; Olmedo et al., 2013).

There are several studies in the literature that evaluate the possible synergistic interactions of essential oils in the effectiveness of their biological activities (Bassolé, 2012; Aumeeruddy-Elalfi et al, 2016). Bioproducts from the species studied have proven their antioxidant and anti-inflammatory actions, making them relevant in this study (Ru et al., 2022; Fadel, et al., 2020; Aumeeruddy-Elalfi, et al., 2016). In this context, the present work aimed to evaluate the chemical profile, anti-inflammatory and antioxidant activity of bioproducts produced from the crossed essential oil of Pimpinella anisum (anise) and Laurus nobilis (laurel).

2.1 Obtaining plant material

The aerial parts of Pimpinella anisum and leaves of Laurus nobilis used in this study were obtained from the federally certified distributor. After collection, the plant species were transported to the Laboratory for Research and Application of Essential Oils (LOEPAV/UFMA), where the leaves were weighed, crushed and stored for the extraction of essential oil from the plant.

2.2 Extraction of essential oils

For the extraction of the essential oil, the hydrodistillation technique was performed with a Clevenger glass extractor coupled to a round bottom flask coupled to a heating mantle as a source of heat. 100 g of each plant material were used, previously dried in a FANEM 520 convective air oven at 45°C, adding distilled water (1:10). Hydrodistillation was performed at 100°C for 3 h and the EO extract was collected. The EO was dried by percolation with anhydrous sodium sulfate (Na2SO4) and centrifuged. These operations were carried out in triplicate and the samples were stored in amber glass ampoules under refrigeration at 4°C before being submitted to analyses.

2.3 Chemical Profile

The identification of chemical constituents was performed by gas chromatography coupled to mass spectrometry (GC-MS), using a QP 2010 Plus model equipment (Shimadzu Corporation, Kyoto, Japan) operating with a fused silica capillary column (30 m × 0. 25 mm) with a DB-5 bonded phase (film thickness, 0.25 µm). Helium was used as a carrier gas with a flow rate of 1.0 mL/min. The injector and detector temperatures were 220 and 240 °C, respectively. The injection volume of the sample was 0.5 μL, diluted in hexane (1%) and injection volume partition ratio (split) of 1:100. The temperature ramp started at 60 °C, with an increase at a rate of 3 °C/min to 240 °C, followed by an increase of 10 °C/min until reaching 300 °C, with the final temperature maintained for 7 min. The column pressure was around 71.0 kPa. The mass spectrometer was operated with an ionization potential of 70 eV and an ion source temperature of 200 °C. Mass analysis was performed in full scan mode, ranging from 45 to 500 Da, with a sweep speed of 1000 Da/s and a scan interval of 0.5 fragments/s. Data were obtained and processed using Lab software Solutions LC/GC Workstation 2.72 (Shimadzu, Kyoto, Japan). The retention index of the compounds was calculated in relation to a homologous series of n-alkanes (nC 9 – nC 18), using the Van den Dool and Kratz equation (Van Den Dool & Kratz, 1963). The identification of the compounds was carried out by comparing the calculated retention indices with those described in the literature (Adams et al., 2017). Comparisons of the mass spectra obtained with those existing in the FFNSC 1.2, NIST107 and NIST21 libraries were also performed.

Quantitative analysis was performed by gas chromatography with flame ionization detector (GC-FID), using equipment model GC-2010 (Shimadzu Corporation, Kyoto, Japan), with identical experimental conditions to those used in the qualitative analysis, except for the temperature of the detector, which was 300°C. The relative percentages of each constituent were obtained by the area normalization method.

2.4 Formulation of nanoemulsions

The preparation of nanoemulsions was carried out according to the adapted methodologies described by Lima et al. (2020), Sugumar et al. (2014), Kubitschek et al. (2014) and Rodrigues et al. (2014).

The oil concentration (5% v/v) was fixed for the formulation. The required amounts of each oil phase constituent (oil+Tween20) were heated to 65 ± 5 °C. The aqueous phase was separately heated to 65 ± 5°C, gently added and mixed with the oil phase, providing a primary formulation, by the phase inversion method. Final homogenization was achieved using a magnetic stirrer, in which the formulation remained under constant agitation at 6000 rpm, until reaching a temperature reduction of 25 °C ± 2 °C.

To prove stability, the formulated nanoemulsion was submitted to different stress tests according to the methodology described by Shafiq et al., (2007). They were reassessed for phase separation by centrifugation. The heating cycle was performed by keeping the formulated nanoemulsion at 40 and 4 °C, alternating each temperature for 48 h. The cycle was repeated three times. This was done to verify the stability of the nanoemulsion at different temperatures. Frozen stress-thawing was performed by keeping the nanoemulsion alternately at -21 and 25 °C for 48 h at each temperature. The cycle was repeated twice. The experiment was carried out in triplicate.

2.5 Microencapsulation

The encapsulation test followed the methodology described by Dubey et al. (2009). Reagents of sodium alginate, anhydrous calcium chloride, the EO and NOE under study, distilled water and tween 80 surfactant were used for the synthesis of alginate microparticles. For the synthesis of encapsulated EO and NOE particles, 60 g of sodium alginate solution (3.5% w/v) were mixed with 15 g of tween 80 and 25 µL of essential oil. The mixture was homogenized at 10,000 rpm and then dropped onto a CaCl2 solution to harden the particles via crosslinking.

2.6 Biofilm

The preparation of biofilms followed the method developed by Zactiti & Kieckbusch (2006), according to the casting technique, which consists of preparing a filmogenic solution and applying it to a support. The formulation consists of 30g of sodium alginate in 1000 mL of distilled water under constant mechanical agitation at 1000 rpm. Then the glycerol is added, keeping the mixture under mechanical agitation for 30 minutes at room temperature. After this period, the essential oil or nanoemulsion at 2% of the total composition is slowly added, keeping the filmogenic solution at 45 °C for 30 minutes under mechanical agitation at 1000 rpm. At the end of this procedure, it was poured into a 15.0 cm diameter petri dish and placed in an oven for solvent evaporation (casting) at a temperature of 45 °C for 24 h. After drying the films, they were left in a desiccator for 24 hours.

2.7 Total Phenolics

The determination of the total phenolic compounds of the crossed essential oil and nanoemulsion was performed by the Folin-Ciocalteu spectrophotometric method (Waterhouse, 2002). 5 mg of samples diluted in 1 mL of ethanol were used. To this solution, 7 mL of distilled water, 800 μL of Folin-Ciocalteu reagent and 2.0 mL of 20% sodium carbonate were added. After two hours, the reading was performed in a UV-VIS spectrophotometer at a length of 760 nm. The standard curve was expressed in milligrams equivalent to grams (mg EAT/g) of tannic acid.

2.8 Evaluation of antioxidant activity

Antioxidant activity was determined by the spectrophotometric method of eliminating hydroxyl radicals from salicylic acid, according to the methods described by Smirnoff & Cumbes (1989).

Essential oil solutions (10-100 mg/L) in 0.2% DMSO, biofilms (10-100 mg/L) and nanoemulsions (no dilution) were prepared. In these solutions, 2 mL of distilled water, 1 mL of salicylic acid (9 mM), 1 mL of ferrous sulfate (9 mM) and 1 mL of hydrogen peroxide (9 mM) were added. Ascorbic acid was used as a positive standard. The reaction mixture was incubated for 60 min at 37 °C in a water bath; after incubation, the absorbance of the mixtures was measured at 510 nm in a UV/VIS spectrophotometer.

The scavenging of hydroxyl radicals was expressed in percentage and the 50% Efficient Concentration (EC50/IC50) capable of inhibiting 50%, respectively, of the scavenging was expressed in mg/L.

2.9 Anti-inflammatory activity by albumin protein denaturation

The anti-inflammatory activity was evaluated by the albumin protein denaturation method by thermal degradation (Padmanabhan & Jangle, 2012).

The reaction mixture (4000 µL) consisted of 1000 µL of different concentrations of essential oils (100-500 mg/L) diluted in PBS, biofilms (10-100 mg/L) and nanoemulsions (without prior dilution in solvent) and 3000 µL of a solution to 10% albumin diluted in PBS and incubated at (37±1) °C for 15 minutes. Denaturation was induced by keeping the reaction mixture at 70°C in a water bath for 10 minutes. After cooling, absorbance was measured at 660 nm in a UV/VIS spectrophotometer. Inhibition of protein denaturation was expressed in percentage and the 50% Efficient Concentration (EC50 /IC50) capable of inhibiting 50% of denaturation was expressed in mg/L.

3.1 Chemical profile

The analysis of the chemical constituents of the cross-EO extraction of Laurus nobilis and Pimpinella anisum plants performed in GC/SM equipment are shown in Table 1.

Table 1 – Chemical composition of cross-EO from Laurus nobilis and Pimpinella anisum

Source: Autorship (2024)

In this study, 10 compounds were identified in the cross-EO sample, the major constituent being (E) -anethole with 74.21%, followed by 1,8-cineole with 20.14%. Studies report 1,8-cineol as the major constituent of L. nobilis, as Mssillou et al. (2020) who identified 25 compounds in flowers of L. nobilis grown in Morocco, quantifying 45.01% of 1,8-cineole. Like Fidan et al. (2019) who identified 38 constituents in the fruits, branches and leaves of L. nobilis cultivated in Bulgaria, quantified 33.3%, 48.5% and 41.0% of 1,8-cineole, respectively. On the other hand, some studies in the literature indicate (E) -anethole as the main component of Pimpinella anisum, as Figueredo et al. (2020), who, analyzing the chemical profile of some plants, identified 18 constituents in the Pimpinella anisum, quantifying 93% of (E) -anethole.

These differences may be due to the harvest time and local, climatic, and seasonal factors, as well as the storage time of the medicinal plant used (Mssillou et al., 2020)

3.2 Total Phenolics

In this study we report the chemical composition as well as the antioxidant and anti-inflammatory activity of the cross essential oil and its bioproducts. The chromatographic analysis revealed a diversity of volatile compounds in the cross- EO, such compounds are responsible for the biological activity of the plants.

Based on the obtained results, the nanoemulsion presented stability and biotechnological potential. It was possible to conclude that the crossed EO and its bioproducts have antioxidant and anti-inflammatory potential.

The mechanisms involved remain complex and poorly understood, as the EO contains a mixture of several dozen chemical constituents of various structures and modes of action that can interact to reduce or increase its effectiveness. This study, unprecedented for this combination, brings new scientific evidence, however, to fully evaluate the potential applications of cross-essential EO and its bioproducts, it is necessary to carry out studies on its toxicological effects to verify its safety.

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Authorship contributions

1 – Renato Barros Pereira

Graduated in Industrial Chemistry from the Federal University of Maranhão

https://orcid.org/0000-0002-0457-914X • renato.pereira@discente.ufma.br

Contribution: Conceptualization, Data curation, Formal Analysis, Investigation,

Methodology, Resources, Software, Visualization, Writing– original draft, Writing – review editing

2 – Thamires de Jesus Teles Ribeiro

Undergraduate student in Industrial Chemistry at the Federal University of Maranhão

https://orcid.org/0000-0003-1495-9282 • thamiresbelle@gmail.com

Contribution: Conceptualization, Data curation, Formal Analysis, Investigation,

Methodology, Resources, Software, Visualization, Writing– original draft, Writing – review editing

3 – Américo Pinheiro Neto

Graduating in Industrial Chemistry from the Federal University of Maranhão

https://orcid.org/0009-0005-6095-0336 • americo.pn@discente.ufma.br

Contribution: Conceptualization, Data curation, Formal Analysis, Investigation,

Methodology, Resources, Software, Visualization, Writing– original draft, Writing – review editing

4 – Victor Elias Mouchrek Filho

PhD in Chemistry from the University of São Paulo

https://orcid.org/0000-0003-2855-7292 • victor.mouchrek@ufma.br

Contribution: Funding acquisition, Project administration

5 – Gustavo Oliveira Everton

PhD in Chemistry from the Federal University of Maranhão

https://orcid.org/0000-0002-0457-914X • gustavooliveiraeverton@gmail.com

Contribution: Conceptualization, Data, Curation, Formal Analysis, Funding, Investigation,

Methodology, Project administration, Resources, Software, Supervision, Validation, Visualization, Writing – original draft, Writing – review editing

How to quote this article

Pereira, R. B., Ribeiro, T. J. T., Pinheiro Neto, A., Mouchrek Filho, V. E., & Everton, G. O. (2026). 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). Ciência e Natura, 48, e88052. DOI: 10.5902/2179460X88052. Available in: https://doi.org/10.5902/2179460X88052