Assessment of physicochemical characteristics and bioactive compounds of the essential oil of wild herbs aromatic from Andean region of South Perú

Avaliação das características físico-químicas e dos compostos bioativos do óleo essencial de ervas aromáticas silvestres da região andina do sul do Peru

Abstract

Essential oils are a subject of study due to the heterogeneity of their components, which vary according to the genus and species of the plant material. The objective of this study was the physicochemical characterization and bioactive components of the essential oil (EO) extracted from wild punamuña (Satureja Boliviana) and runtuhuayra (Clinopodium Weberbaueri (Mansf.) Govaerts) herbs from high Andean areas of southern Peru. The extraction of the EO from both species was carried out using the steam distillation technique, the density characterization using gravimetric methods and the acidity, peroxide index and refraction by analytical methods recommended by the Norma Tecnica Peruana (NTP). The bioactive compounds were quantified using gas chromatography coupled to a mass spectrometry detector (GC-MS). A better EO performance was obtained from punañuna 0.38% (w/w) compared to runtuhuayra 0.28% (w/w); In both samples, the density and refractive index were similar values (0.93-0.94) g/mL and (1.528-1.520) (p>0.05) respectively; However, the acid and peroxide index showed a significant difference between the samples studied (p<0.05). 37 bioactive compounds synthesized as secondary metabolites in Satureja Boliviana EO were identified, with the majority being monoterpenes (62%) highlighted by menthone, L-menthone, pulegone and 3-cyclohexen-1-one. 2-isopropyl-5-methyl, linalool, α-cadinene and α-cadinol; Meanwhile, in the EO of Clinopodium Weberbaueri, 28 compounds were detected and quantified, in which monoterpenes predominate (61%) made up of pulegone (45.67%); isomenthol (13.85%), menthone (6.05%), carvacrol (5.39%), and also D-limonene; o-cymene; 3-octanol; β-pinene and α-terpineol successively. This characterization of the EO of the aforementioned samples reveals recent a new additive or ingredient alternative for the industry due to its biological value associated with antioxidant, antimicrobial, anti-inflammatory activities and psychotherapeutics.

Keywords:
essential oils; bioactive compounds; monoterpenes; wild herbs

Resumo

Os óleos essenciais são objeto de estudo devido à heterogeneidade de seus componentes, que variam de acordo com o gênero e espécie do material vegetal. O objetivo deste estudo foi a caracterização físico-química e dos componentes bioativos do óleo essencial (OE) extraído das ervas silvestres punamuña (Satureja boliviana) e runtuhuayra (Clinopodium weberbaueri (Mansf.) Govaerts) das áreas alto-andinas do sul do Peru. A extração do OE de ambas as espécies foi realizada usando a técnica de destilação a vapor, a caracterização da densidade por métodos gravimétricos e a acidez, índice de peróxido e refração, por métodos analíticos recomendados pela norma técnica peruana (NTP). Os compostos bioativos foram quantificados por cromatografia gasosa acoplada a um detector de espectrometria de massa (GC-MS). Um melhor desempenho de OE foi obtido com punañuna 0,38% (m/m) em comparação com runtuhuayra 0,28% (m/m); Em ambas as amostras, a densidade e o índice de refração apresentaram valores semelhantes (0,93-0,94) g/mL e (1,528-1,520) (p>0,05), respectivamente. Porém, o índice de acidez e o peróxido apresentaram diferença significativa entre as amostras estudadas (p<0,05). Foram identificados 37 compostos bioativos sintetizados como metabólitos secundários no OE de Satureja boliviana, sendo a maioria monoterpenos (62%), com destaque para mentona, L-mentona, pulegona e 3-ciclohexeno-1-ona. Também foram encontrados 2-isopropil-5-metil, linalol, α-cadineno e α-cadinol. Enquanto isso, no OE de Clinopodium weberbaueri, foram detectados e quantificados 28 compostos, nos quais predominam os monoterpenos (61%) constituídos por pulegona (45,67%); isomentol (13,85%); mentona (6,05%), carvacrol (5,39%), e também D-limoneno, o-cimeno; 3-octanol; β-pineno e α-terpineol, sucessivamente. Esta recente caracterização do OE das amostras citadas revela uma nova alternativa de aditivo ou ingrediente para a indústria devido ao seu valor biológico associado a atividades antioxidantes, antimicrobianas, anti-inflamatórias e psicoterapêuticas.

Palavras-chave:
óleos essenciais; compostos bioativos; monoterpenos; ervas silvestres

1. Introduction

Essential oils (EO) are complex substances composed of hundreds of components that can vary greatly in their composition depending on the extraction process by the producer or the origin of the plant (Sousa et al., 2023). The most widely used method for extracting essential oils is steam distillation due to its simplicity and low investment requirements. Due to the importance of this extractive method, technological updates today represent an immense opportunity (Machado et al., 2022).

EO are widely used in the food industry, as condiments and flavorings; also in the pharmaceutical, cosmetic and tobacco industries, such as perfumes and essences (Ochoa Pumaylle et al., 2012). In addition, several researches have revealed that some essential oils possess antibacterial, antifungal and antiviral activities because they are active against multiple DNA and RNA viruses, including herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2), it has also been treated against poliovirus, adenovirus, dengue virus type 2, yellow fever virus, influenza virus, respiratory syncytial virus, Zika virus, coronavirus, coxsackie virus B-1 (Wani et al., 2021; Azimi et al., 2018; Mesa et al., 2007), insecticide, antitoxic (Kahriman et al., 2011), and antioxidants, due to its high concentration of phenolic compounds (Yaldiz and Çamlica, 2017). The emergence of new drug-resistant virus strains that cause serious health problems, such as coronavirus disease 2019 (COVID-19), has prompted the search for new sources, making the study of essential oils relevant for their potential medicinal purposes.

Peru has an extensive floral biodiversity with 4,000 species of native plants registered, of which 1400 are native medicinal plants that were recorded around 1400, being used empirically for their therapeutic benefits in health care (Bussmann and Sharon, 2015). Within this context, the southern Andean region of Peru, precisely in the Apurimac region, at an altitude of 2000 to 4800 meters above sea level, abounds a variety of exotic medicinal plants that are usually used by the inhabitants as traditional medicine to relieve stomach and respiratory discomfort (Barrial-Lujan et al., 2023; Sotelo, 2014). Harvesting of punamuña (Satureja boliviana) and runtuwayra (Clinopodium weberbaueri (Mansf.)) plants from the high Andean area of the province of Andahuaylas in Peru is due to the need to incorporate these species into agroindustry processes, avoiding thus abandonment. devaluation and loss in its geographical environment. With the extraction, characterization of physicochemical properties and quantification of bioactive compounds from the essential oil of the aforementioned species, the aim is to reveal their functional value for food or pharmacological applications in the context of sustainable development.

2. Material and Methods

2.1. Plant materials

Essential oils are products extracted from different parts of plants, such as leaves, stems, roots, and bark (Machado et al., 2022), our study focused on the leaves of wild herbs andean.

The fresh leaves of Punamuña (Satureja Boliviana) and Runtuwayra (Clinopodium Weberbaueri (Mansf.) Govaerts) were collected from wild plants corresponding to the vegetation (foliation) period. The collection area is located at a latitude of 13°36’07.89’S and a longitude of 73°16’33.13’W, more than 3200 meters above sea level belonging to the province of Andahuaylas, Apurímac, Peru.

The essential oil was obtained by means of a steam entrainment distillation equipment. 2500 g of plant material was weighed and subjected to a tank supplying supersaturated water vapor at a pressure of 14 psi for 2 hours. The essential oil (EO) was separated from the water by settling connected to a siphon system and stored in dark-colored containers at room temperature (25 ± 0.6 °C) until analysis.

The essential oil yield (EOY) was calculated in relation to the mass of oil extracted and the mass of plants/leaves expressed in the Equation 1.

$\text{EOY}=\frac{m_{oil}}{m_{plant}}x100$ (1)

2.2. Physicochemical characteristics

The physicochemical characteristics were obtained following the instructions cited in the Peruvian Technical Standard (density, refractive index% and acidity). For the determination of the density, expressed in g/mL, the oils were calculated on a pycnometer at 20 °C as quoted in the Norma Técnica Peruana (NTP) 279 ISO (NTP, 2011a).

The acid value (AV) was measured expressed as a percentage of oleic acid, using the method recommended by NTP 319.085 (NTP, 1974a), it’s calculated with the Equation 2.

$\text{AV}\left(\text{\%}\right)=\frac{282\text{x V x N x}100}{\text{p}}$ (2)

Here: V = volume of potassium hydroxide (KOH) used (mL); N = Normality of KOH; P= weight of oil (g).

The peroxide value (PV) was determined by volumetric analysis; this consisted of measuring the ability of peroxides to oxidize KI iodide ions and produce iodine which was titrated with sodium thiosulfate. The unit of measurement of this component was expressed in milliequivalents of active oxygen per kg of fat (NTP, 2011b) It is calculated using the following the Equation 3:

$\text{PV}=\frac{VxNx1000}{\text{p}}$ (3)

Here: V = titrated sodium thiosulfate solution (mL); N = exact normality of the sodium thiosulfate solution used at 0.01 N; P = weight in grams of the sample.

The refractive index of essential oil was measured using the method recommended by NTP 319.075 (NTP, 1974b) and (Ochoa Pumaylle et al., 2012). In this analysis, the Ivymen System ABBE model RI-71 refractometer was used. whose principle is the relationship between air and the substance measured at 20 °C. The action of the drying agent was verified on the prepared sample through a series of modifications of the refractive index after each desiccation.

2.3. Detection and quantification of bioactive compounds

The bioactive compounds of the punamuña essential oil of (PEO) and runtuhuayra essential oil of (REO) were detected and quantified following the Ochoa procedure (Ochoa Pumaylle et al., 2012) with slight modification. Where 10 μL of essential oil was added to a vial, making up the volume with 10 mL of methanol, after homogenizing, it was transferred to a 1.5 mL vial for analysis. The chemical composition of the oil is used in a gas chromatograph (GC), model HP 6890N, coupled to 5975B Network System mass selective detector and an 7683B injector automatic, both from Agilent Technologies. The detector worked in a mass range of 40 to 500 uma, the interface and source temperatures were 260 °C and 130 °C respectively. An HP-5MS 5% Phenylmethylsiloxane column (30 m × 0.25 mm diameter × 0.5 µm thickness) was used. Helium was used as carrier gas with a flow of 1 mL/min at constant volume, Pressure 8.23 psi. The injection was carried out in a “split splitless” type injector at 260 °C. 1 µL of essential oil solution in methanol was injected and analyzed. The temperature of the GC oven was initially programmed at 60 °C and then to a final temperature of 260 °C at a rate of 5 °C/min. Running time 77.8 min. Compound identification was performed with system MSD Chem Station (Version D.02.00.275) computerized data; through the combined use of the NIST v 5.0 database.

2.4. Statistical analysis

The analytical results were reported in triplicate, whose statistical analysis was through a Completely Randomized Design (CRD); The analysis of variance was performed with 0.05 significance; When a significant difference was found, the mean comparison test was performed using the LSD-Fisher test. The data were processed with the help of Centurion statistical software version XVII.

3. Results

The yield of the essential oil obtained between the samples studied showed a statistically significant difference at a 95% confidence level, Satureja Boliviana being slightly better to Clinopodium Weberbaueri (Mansf.) Govaerts as seen in Table 1, the values of density (0.933-0.934 g/mL), acidity (3.319-4.300%), peroxide index (0.700-1.241 meq O₂) varied. /kg EO) and refraction (1.528-1.520); and in both cases the acidity and peroxide index showed a statistically significant difference (p<0.05). On the other hand, the density (0.933-0.934 g/mL) and the refractive index did not reveal a significant difference (p>0.05).

Table 1
Physicochemical property of essential oil of two wild herbs.

Characteristics	PEO			REO
	X̄	±	S	X̄	±	S
Yield (%)	0.38	±	0.050A	0,28	±	0.050B
Density (g/mL)	0.933	±	0.002A	0.934	±	0.005A
Acidity (% Oleic acid)	3.319	±	0.008A	4.300	±	0.026B
Peroxide index (meq O2/kg EO)	0.700	±	0.002A	1.241	±	0.006B
Refractive index	1.528	±	0.005A	1.520	±	0.008A

• Different letters in the same row indicate statistically significant differences between the samples studied, assessed through LSD-Fisher (α≤5%). X̄ = arithmetic mean; S = standard deviation; PEO = punañuma essential oil; REO = runtuhuayra essential oil.

Similarly, Table 2 shows the detection and quantification of 37 bioactive components, also known as secondary metabolites. In the case of essential oil extracted from Satureja Boliviana, the most outstanding components were: Menthone, L-Menthone, Pulegone y 3-Cyclohexen-1-one. 2-isopropyl-5-methyl, Linalool, α-Cadinene y α-Cadinol with a concentration ranging from 16.42; 19.49; 15.76; 15.75; 3.24; 2.90 and 1.8% respectively. Meanwhile, in REO those that stand out are: pulegone (45.67%), Isomenthol (13.85%), Menthone (6.05%), Phenol, 2-methyl-5-(1-methylethyl) (5.38%), carvacrol (5.39%) and Caryophyllene (3.82%), successively.

Table 2
Quantification of chemical compounds of essential oil of two wild herbs.

N°	Name of compounds	Molecular formular	Molecular weight	R.T.	PEO			REO
					X̄	±	S	X̄	±	S
1	1-Octen-3-ol	C8H16O	128.21	8.38	0.233	±	0.001	nd
2	β-Pinene	C10H16	136.23	8.43	0.124	±	0.001	0.233	±	0.002
3	β.-Myrcene	C10H16	136.23	8.76	nd			0.342	±	0.002
4	3-Octanol	C8H18O	130.23	8.84	0.161	±	0.001	nd
5	Benzene, 1-methoxy-4-methyl	C8H10O	122.16	9.70	nd			0.534	±	0.016
6	o-Cymene	C10H14	134.22	9.89	nd			1.23	±	0.013
7	D-Limonene	C10H16	136.23	9.93	0.190	±	0.00	0.58	±	0.015
8	Eucalyptol	C10H18O	154.25	10.09	0.961	±	0.004	nd
9	γ-Terpinene	C10H16	136.23	10.87	0.141	±	0.00	nd
10	Linalool	C10H18O	154.25	12.02	3.247	±	0.006	nd
11	Octen-3-yl acetate	C10H18O2	170.25	12.26	0.297	±	0.015	nd
12	Camphor	C10H16O	152.23	13.38	0.114	±	0.015	nd
13	Terrein	C8H10O3	154.16	13.62	nd			1.203	±	0.012
14	Menthone	C10H18O	154.25	13.92	16.419	±	0.018	6.05	±	0.03
15	Isomenthol	C10H20O	156.26	14.26	nd			13.85	±	0.07
16	L-Menthone	C10H18O	154.25	14.25	19.495	±	0.057	nd
17	Isopulegol	C10H18O	154.25	14.36	nd			0.709	±	0.04
18	p-Menthone	C10H20	140.27	14.56	2.094	±	0.007	nd
19	α-Terpineol	C10H18O	154.25	14.95	0.182	±	0.002	0.16	±	0.001
20	Pulegone	C10H16O	152.23	16.24	15.757	±	0.001	45.67	±	0.16
21	3-Cyclohexen-1-one. 2-isopropyl-5-methyl	C10H16O	152.23	16.76	15.753	±	0.023	0.938	±	0.07
22	Thymol	C10H14O	150.22	17.53	1.617	±	0.197	0.37	±	0.001
23	3-Methyl-4-isopropylphenol	C10H14O	150.22	17.74	1.184	±	0.017	nd
24	Phenol, 2-methyl-5-(1-methylethyl)-	C10H14O	150.22	18.01	nd			3.291	±	0.02
25	2,4-Cycloheptadien-1-one, 2,6,6-trimethyl-	C10H14O	150.22	18.05	0.647	±	0.012	0.17	±	0.01
26	Propanoic acid, 2-methyl-, 4-methylphenyl	C10H20O2	172.26	18.39	nd			0.181	±	0.11
27	β-Bourbonene	C15H24	204.35	19.49	1.357	±	0.005	nd
28	3-Allyl-6-methoxyphenol	C10H12O2	164.20	19.80	nd			0.140	±	0.11
29	Carvacrol	C10H14O	150.22	20.19	nd			5.39	±	0.02
30	Butanoic acid, 2-methyl-, phenylmethyl ester	C12H16O2	192.25	20.62	nd			0.278	±	0.01
31	p-Tolyl pivalate	C12H16O2	192.25	21.16	nd			0.561	±	0.01
32	Caryophyllene	C15H24	204.36	21.52	0.160	±	0.002	3.82	±	0.01
33	3.5-Octadiene. 4.5-diethyl-	C12H22	166.30	21.87	4.448	±	0.015	nd
34	γ-Muurolene	C15H24	204.35	23.13	0.374	±	0.031	nd
35	1,6-Cyclodecadiene, 1-methyl-5-methylene-8-	C15H24	204.35	23.26	0.490	±	0.015	nd
36	Bicyclogermacrene	C15H24	204.35	23.71	0.430	±	0.001	nd
37	γ-Elemene	C15H24	204.35	23.94	nd			2.85	±	0.01
38	Naphthalene, 1,2,4a,5,6,8a-hexahydro-4,7-dimethyl-1	C15H24	204.35	24.29	3.054	±	0.002	nd
39	β-Cadinene	C15H28	208.38	24.41	0.710	±	0.003	nd
40	α-Cadinene	C15H24	204.35	24.49	2.900	±	0.004	nd
41	1,6,10-Dodecatrien-3-ol, 3,7,11-trimethyl-	C15H26O	222.37	24.89	0.221	±	0.003	nd
42	1H-Cycloprop[e]azulene, 1a,2,3,5,6,7,7a,7b-octahydro-1,1,4,7-tetramethyl	C15H24	204.35	26.01	0.368	±	0.039	nd
43	Caryophyllene oxide	C15H24O	220.35	26.14	0.462	±	0.116	3.818	±	0.01
44	1H-Cycloprop[e]azulen-4-ol, decahydro-1,1,4,7-tetramethyl	C15H26O	222.37	26.35	0.578	±	0.002	0.743	±	0.002
45	trans-Edulan	C13H20O	192.29	26.45	0.188	±	0.012	nd
46	Naphthalene, 1,2,3,4,4a,7-hexahydro-1,6-dimethyl-4	C15H24	204.35	27.25	0.613	±	0.121	0.131	±	0.020
47	Cyclododecyne	C12H20	164.29	27.30	0.124	±	0.101	0.743	±	0.004
48	Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene	C15H24	204.35	27.48	1.515	±	0.051	0.496	±	0.001
49	Tr- c-lo[3.3.1.1(3,7)]decane,	C10H15NO2	181.23	27.67	0.231	±	0.001	nd
50	α-Cadinol	C15H26O	222.37	28.39	1.858	±	0.007	0.171	±	0.003

• Where: R.T. = retention time; X̄ = arithmetic mean; S = standard deviation; nd = not detected; PEO = punañuma essential oil; REO = runtuhuayra essential oil.

The compounds detected in the PEO that are recorded in Table 2 are also classified into Monoterpene hydrocarbons that represent 14%, Oxygenated monoterpenes 49%, Sesquiterpene hydrocarbons 19%, Oxygenated sesquiterpenes 11% and Other unidentified compounds 8%. Likewise, the bioactives of REO are classified as Monoterpene Hydrocarbons up to 14%, Oxygenated Monoterpenes 46%, Sesquiterpene Hydrocarbons 11%, Oxygenated Sesquiterpenes 29% and Other unidentified compounds 7%. In this sense, both plants studied synthesize high concentrations of monoterpenes, so they would be associated with exerting a series of effects directly relevant to neurocognitive and anti-inflammatory function (Kennedy et al., 2018). Monoterpenes have also been shown to exert chemopreventive and chemotherapeutic activities in breast tumor models and may therefore represent a new class of therapeutic agents (Shuaib et al., 2016); and although this group of plants is low in sesquiterpenes, they would also be associated with pharmacological properties, that is, antioxidant, antimicrobial, antifungal, antiviral and pesticide activities (Dhingra and Chopra, 2023). Consequently, the essential oil extracted from both the Bolivian Satureja plant and Clinopodium Weberbaueri could be very useful as an ingredient and/or food additive.

4. Discussion

Studies indicate that the extraction yield of essential oils varies with each species of aromatic plants, with the majority ranging between 0.2 and 2% (Chacón et al., 2011). Our results, the values determined were 0.38% and 0.28% w/w on a wet weight for PEO and REO, respectively; being higher than the yields of essential oils of Muña 0.19% w/w (Cano, 2007). Yields of 0.40% and 0.59% w/w, were obtained in mint and eucalyptus samples (Afzal et al., 2017) in the orégano 1,30% v/w (Albado Plaus et al., 2001) being the same method of extraction,. However, expressing our result on a dry basis, we obtained 2.71% and 1.86% w/w in PEO and REO and it is superior to other satureja species that were isolated by hydrodistillation; as is the case of the leaves of Satureja macrostema, they reported a yield on a dry basis of 0.8% (w/w) (Barrientos Ramírez et al., 2023); Likewise, S. mutica, S. macrantha and S. intermedia obtained yields of 2.31%, 1.48% and 1.45% (w/w), based on dry weights, respectively (Sefidkon and Jamzad, 2005). Variations in the extraction yield of essential oils depend precisely on the type of plant species, the different sections of the plant, the size of the raw material used in the process, as well as the pressure, time and temperature conditions or methods used (Tembe et al., 2018; Quoc, 2022).

The REO and PEO had similar density values (0.93) g/mL (p>0.05) and were relatively similar to the Malaga (Málaga, 2014) 0.955 g/mL in Clinopodium Bolivianum essential oil; values between 0.90-0.94 g/mL in Minthostachys mollis (Humani, 2015), and other 0.9047 g/mL in EO of Satureja brevicalyx (Carhuapoma, 2007), in EO of Ceratonia siliqua pulp and seed – 0.833 and 0.91 g/mL, respectively (Ouis and Hariri, 2018). In general, the determination of density sometimes makes it possible to make certain deductions about the composition of essences. Thus, essential oils with densities of less than 1 g/mL are rich in hydrocarbons, alcohols, esters and ketones (Humani, 2015); and it is presumed that it has less content of phenols or their derivatives and certain aromatic esters that make these values lower than those determined in this study.

Regarding the acidity and peroxide index, they showed a significant difference between the samples studied (p<0.05), where the acidity of REO and PEO fluctuated between (3.319 - 4.300% oleic acid), being higher than those reported from Huamani for Mínthostachys mollis (1.626 to 1.711), also higher than the OE of fresh withered fruits and dried leaves which was 1.8, 1.8 and 1.6, respectively (Humani, 2015). The acidity index gives an idea of the free acid content of essential oils. The acid number is an important parameter that indicates the age, quality, edibility and suitability of essential oils (Shuaib et al., 2016). the variations in the acidity of EO, on the one hand, denote the altitudinal variations in which the plants were grown (Humani, 2015). and the peroxide index for the studied samples fluctuates between (0.700 - 1.241 meq O2/kg AE), these values were lower than the samples of three species of mint Mentha spicata that ranged between 12 and 21.6 m Eq O2/kg (Zekri et al., 2023). Variations in some physicochemical properties between the plant species and even within the same region are strongly and directly affected by extraction techniques, climatic conditions, plant varieties, regions, harvest periods, genotype, type of material and chemical composition (Quoc, 2022).

The refractive index is a physical property that is frequently used to test the purity of oils. The lower the refractive index, the better the quality of the essential oil (Coulibaly et al., 2023). The samples studied did not show a significant difference (p>0.05); Thus, for Satureja boliviana and Clinopodium Weberbaueri the refractive index was 1.528 and 1.520 respectively. This value was similar to the values reported for essential oils extracted from Piper aduncum Linnaeus 1.5349 (Diaz, 2018), valúe of 1,4745 a 1,4769 in Minthostachys mollis (Humani, 2015), In some aromatic Origanum vulgare plants (1.4774) (Albado Plaus et al., 2001); Lippia alba (1,4916); Luma apiculata (1,4774) (Carhuapoma et al., 2009). The essential oil studied could be considered of good quality in terms of purity. A low refractive index of an essential oil indicates its low refraction of light, which could favor its use in cosmetic products (Gurav et al., 2021).

The bioactive compounds of the essential oil of Satureja boliviana and their relative quantities, by the analysis of Gas Chromatography, presented in Table 2. Monoterpenes account for 62% of the relative composition, of which five constitute monoterpene hydrocarbons (30%) and eighteen oxygenated compounds (37%), quantitatively representing the largest proportion of essential oil. The majority component of monoterpenes was Menthone (16.42%); Pulegone (15.75%); L-Menthone (19.49%) and Linalool (3.24%) successively, and in addition D-Limonene; o-Cymene; Eucalyptol; β-Pinene; γ-Terpinene; Naphthalene about 2%. These major compounds have high biological value that would be related to the regulation of allergic inflammation of the respiratory tract (Su and Lin, 2022), antidepressant effects (Xue et al., 2015). In this same sample, sesquiterpenes represent 30% classified into sesquiterene hydrocarbons and oxygenated sesquiterpenes of 19% and 11% respectively; which are made up of Caryophyllene; β-Bourbonene; γ-Muurolene; Bicyclogermacrene; β-Cadinene; α-Cadinene; Caryophyllene oxide; 1H-Cycloprop-4; Bicyclo and α-Cadinol. These data are consistent with the essential oil composition of Satureja brevicalyx, Satureja boliviana and Peruvian Satureja reported by Carhuapoma et al. (2009), Viturro et al., (2000) and Senatore. (1998). In EO of Ocimum americanum L. they found Linalool (0.7%); α-terpineol (1.7%); β-elemene (0.2%); Caryophyllene oxide (0.3%) (Coulibaly et al., 2023) being similar to our results. oxygenated monoterpenes (74.8%), sesquiterpene hydrocarbons (16%), monoterpene hydrocarbons (4.1%) and oxygenated sesquiterpenes (1.5%). In samples of Bolivian Satureja (Lamiaceae), oxygenated monoterpenes consisting of pulegone (27.2%), linalool (20.3%), menthone (11.1%), isomenthone (8.3%), cis-isopulego (2.7%), trans-isopulego (0.9%), carvacrol (0.6%), thymol (0.6%) and α-terpineol (0.5%) stood out (Salcedo and Alonso, 2021). In vitro research has shown that Satureja boliviana could suppress the overall effects of vesicular stomatitis virus (VSV), hepatitis B, and herpes simplex virus type 1 (HSV-1) (Ejaz et al., 2023).

As for Clinopodium Weberbaueri (Mansf.) Govaerts essential oil, 61% monoterpenes were also quantified, of which three form monoterpene hydrocarbons (14.3%) and six oxygenated compounds (46.7%), in this sample Pulegone (45.67%) stands out; Isomenthol (13.85%); Menthone (6.05%); and Carvacrol (5.39%) and also D-Limonene; o-Cymene; 3-Octanol; β-Pinene and α-Terpineol about 1.3%. These compounds would be associated with pharmacological properties, antioxidant, antimicrobial, anti-food, antifungal, antiviral and pesticide activities (Dhingra and Chopra, 2023), possible anti-inflammatory, antiviral and immunomodulatory properties and in the control of hypertension (Razzaq et al., 2023; Javed et al., 2021). By contrast, sesquiterpenes reflect the 32.1% that are classified into sesquiterpene hydrocarbons (10.7%) and oxygenated sesquiterpenes (21.4%), which are made up of Caryophyllene; γ-Elemene; Caryophyllene oxide; 1H-Cycloprop4* and α-Cadinol. This sample is relatively superior to Clinopodium vulgare L Carvacrol (3.3%); Pulegone (0.1%); (-pinene (2.1%) (Kiliç et al., 2017). Besides the results obtained revealed that the group of sesquiterpenes that appear in the EA (in small amounts). Significant variations in the chemical profile of M. arvensis L. EO were observed: e.g., menthol, p-menthone, isomenthone, and neomenthol from the aerial parts of M. arvensis L. from India account for 71.40%, 8.04%, 5.42%, and 3.18%, respectively (Pandey et al., 2003), while the EC of leaves of M. arvensis L. from the southeastern region of Macedonia contained menthol (32.47%), imenthonone (15.97%), 1,8-cineole (5.4%) and neomenthol (5.24%) (Mihajlov et al., 2019). These significant variations of chemical compounds are also influenced by factors such as the plant's stage of development, variety, geographic origin, part of the plant used, age, season, and plant condition at the time of harvest, as well as the method of extraction, conditions of analysis, and solvent used (Quoc, 2022). To complement the chemical composition, reference literature was consulted, as shown in Table 3, in which it is possible to infer similarity with the compounds reported by other authors.

Table 3
Chemical compounds of essential oil found in Satureja species studied in different regions of the world.

Species	Country	Main components (%)	References
Satureja boliviana	Peru	Menthone (54.11), isomenthone (15.12), carvacrol (6.76), isopulegone (5.45), 1.8-cineole (4.20), pulegone (2.22), p-cymene (1.84), linalool (1.77)	Velasco-Negueruela et al. (1994)
Satureja boliviana	Peru	Isomenthone (29.0), menthone (12.6), pulegone (12.6), thyrnol (6.8), p-cymene (4.3), 1.8-cineole (4.2), isopulegone (4.1), bicyclogermacrene (3.0), linalool (3.0)	Vila et al. (1996)
Satureja boliviana	Bolivia	Isornenthone (27.0), pulegone (20.0), thymol (14.7), 1.8-cineole (9.8), p-cymene (5.4), spathulenol (2.3)	Vila et al. (1996)
Satureja boliviana	Peru	Isomenthone (29.7), menthone (24.2), pulegone (10.7), cis-dihydrocarvon (6.3), thymol (4.5), 1.8-cineole (4.0), p-cymene (3.4), linalool (3.1)	Senatore et al. (1998)
Satureja brevicalix	Peru	Menthone (37.5), isomenthone (25.2), pulegone (8.4), cis-dihydrocarvone (5.0), linalool (3.6), 1.8-cineole (2.8), p-cymene (2.3)	Senatore et al. (1998)
Satureja boliviana	Argentina	γ-Terpinene (15.4), trans-caryophyllene (10.20), germacrene D, bicyclogermacrene (8.3), 1.8-cineole (7.4). linalool (4.8), trans-pinan-2-ol (3.9), trans-β-ocimene (3.4), δ- cadinene (2.80), p-cymene (2.80)	Viturro et al. (2000)
Satureja Mutica	Azarbaijan	Thymol (62.6), p-cymene (9.4), methyl thymol (5.4), carvacrol (6.6), γ-terpinene (3.4), α-copaene (1.7), caryophyllene oxide (1.6)	Gohari et al. (2009)
Satureja atropatana	Azarbaijan	Thymol (62.1), p-cymene (6.1), spathulenol (5.2), γ-terpinene (3.3), carvacrol (1.5), hexadecanoic acid (1.4)	Gohari et al. (2009)
Satureja bachtiarica	Iran	Thymol (65.1), γ-terpinene (15.0), β-caryophyllene (4.85), p-cymene (4.4), linalool (3.5), borneol (3.05), α-terpipene (1.1)	Moein et al. (2012)
Satureja incana	Peru	Germacrene D (25.91), caryofileno (22.10), α-ocimene (12.62), 4(8)-p-menthone (6.73), bicyclogermacrene (4.12), humulene (3.95), caryophyllene oxide (3.08), limonene (2.44)	Ricaldi Sarapura and Martínez Martínez (2014)
Satureja briquetti	Morocco	Borneol (27.64), β-bisabolene (9.58), α-pinene (6.97), linalool (6.77), camphene (5.72), α-longipinene (4.24), camphor (3.57), cis-α-bisabolene (3.47), β-pinene (3.25)	Jennan et al. (2018)
Satureja atlantica	Morocco	Piperitenone oxide (24.27), limonene (20.57), pulegone (16.88), cis-piperitone oxide (15.55), menthalone (6.84), borneol (1.83)	Jennan et al. (2018)
Satureja Alpina	Morocco	Pulegone (87.74), α-pinene (2.50), menthone (1.69), trans-isopulegone (1.39), limonene (1.13)	Jennan et al. (2018)

Finally, it should be noted that the essential oil extracted from the leaves of Satureja boliviana, being formed by monoterpenes, would be associated with exerting a series of effects directly relevant to neurocognitive and anti-inflammatory function (Kennedy et al., 2018), In the case of menthone, it was associated with the regulation of allergic inflammation of the airways (Su and Lin, 2022). Studies reveal that L-Menthone has an antidepressant effect, test carried out in mice exposed to chronic unpredictable mild stress by regulating inflammasome 3 (NLRP3) (Xue et al., 2015), Linalool and β-pinene appear as a promising bioactive compound in the therapeutic arsenal, capable of treating depressive disorders, as it interacts positively with a variety of pathophysiological factors, and as well as the regulation of the gut microbiota, with contributions on depressive symptoms (Santos et al., 2022). In Clinopodium Weberbaueri (Mansf.) Govaerts essential oil, the main compounds would be associated with pharmacological properties, i.e. antioxidant, antimicrobial, anti-food, antifungal, antiviral and pesticide activities (Dhingra and Chopra, 2023). Just like the pulegone demonstrated its use as a potential candidate in the control of hypertension (Razzaq et al., 2023), another study, isomenthol exhibited several biological activities, making it a potential candidate for use in food preservation and pharmaceuticals. Carvacrol, as a potent antioxidant and immunomodulator, could enhance host cellular immunity against infections, published studies plausibly suggest possible anti-inflammatory, antiviral, and immunomodulatory properties that could be an important therapeutic candidate for COVID-19 (Javed et al., 2021).

In this sense, the essential oils extracted from the species PEO and REO, by distillation by steam dragging were acceptable compared to other species of Satureja, showing physicochemical properties in both species with quality ranges of essential oils for their subsequent industrial scaling and their bioactive components would be associated with antifungal activities. antiviral, antiviral and immunomodulatory, making Andean plants a potential candidate that could be used in the pharmaceutical industry or in the production of functional foods promoting the achievement of the Sustainable Development Goals.

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Publication Dates

• Publication in this collection
  15 Nov 2024
• Date of issue
  2024

History

• Received
  01 May 2024
• Accepted
  28 Aug 2024