A Comparative Study of The Chemical Composition and Antioxidant Capacity of The Essential Oils From Three Species of Mentha Cultivated in Morocco.

© 2024 Journal of Pharmacy & Pharmacognosy Research, 12 (6), 1021-1039, 2024
ISSN 0719-4250
https://jppres.com
DOI: https://doi.org/10.56499/jppres23.1897_12.6.1021
Original Article
A comparative study of the chemical composition and antioxidant

capacity of the essential oils from three species of Mentha
cultivated in Morocco
[Estudio comparativo de la composición química y la actividad antioxidante de los aceites esenciales de tres especies de
Mentha cultivadas en Marruecos]
Arrahmouni Rayan1, Ouazzani Chadia1*, Er-Ramly Azzedine2, Moustaghfir Abdellah2, Benchama Zakaria3,
Elamrani Abdelaziz3, Benkhouili Fatima Zahra4, El-Guourrami Otman5, Dami Abdallah1, Balouch Lhousaine1
1Laboratory of Biochemistry and Molecular Biology, Faculty of Medicine and Pharmacy, Mohammed V University in Rabat, Morocco.
2Laboratory of Odontological Biomaterials and Nanotechnology, Faculty of Dental Medicine, Mohammed V University in Rabat, Morocco.
3Laboratory of Organic Synthesis, Extraction and Valorization, Faculty of Sciences Ain Chock, Hassan II University of Casablanca, Morocco.
4Laboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, Mohammed V University in Rabat, Morocco.
5Laboratory of Analytical Chemistry, Faculty of Medicine and Pharmacy, Mohammed V University in Rabat, Morocco.
*E-mail: [email protected]
Abstract
Context: Mentha species are well known for their health benefits. Products extracted from aromatic plants of this genus (Mentha) are increasingly being
studied for their active constituents in order to replace synthetic products that are harmful to health.
Aims: To determine the chemical composition, physicochemical parameters, and antioxidant properties of essential oils of M. spicata, M. piperita, and M.
pulegium. These plants were collected from three different geographical areas in the Rabat-Sale-Kenitra region of Morocco, with an additional focus on
analyzing the fluctuation of their chemical composition based on their locations.
Methods: Essential oils obtained through hydrodistillation of the fresh aerial parts of the plants were analyzed via gas chromatography and gas
chromatography-mass spectrometry. The antioxidant capacity was measured by several chemical tests: DPPH, ABTS, and FRAP.
Results: Multiple major components were identified, showcasing variations in composition between species as well as between plants of the same species. M.
spicata was characterized by carvone, piperitone, 1,3,8-p-menthatriene; while M. piperita features linalool, D-carvone, 1,3,8-p-menthatriene; and M. pulegium
had a single major component which is pulegone. To the best of our knowledge, it is assumed that a new set of chemotypes may be defined based on the
geographical regions studied. The examined essential oils demonstrated notable antioxidant efficacy.
Conclusions: These findings suggest the potential use of extracts from these plants as an alternative to synthetic chemical products. Therefore, they could find
applications in complementary medicine as well as in the pharmaceutical and food industries.
Keywords: antioxidant capacity; chemical composition; essential oils; Mentha piperita; Mentha pulegium; Mentha spicata.
Resumen
Contexto: Las especies de Mentha son bien conocidas por sus beneficios para la salud. Los productos extraídos de las plantas aromáticas de este género
(Mentha) son cada vez más estudiados por sus constituyentes activos con el fin de sustituir los productos sintéticos perjudiciales para la salud.
Objetivos: Determinar la composición química, los parámetros fisicoquímicos y las propiedades antioxidantes de los aceites esenciales de M. spicata, M.
piperita y M. pulegium. Estas plantas se recolectaron en tres zonas geográficas diferentes de la región marroquí de Rabat-Sale-Kenitra, con el objetivo
adicional de analizar la fluctuación de su composición química en función de su ubicación.
Métodos: Los aceites esenciales obtenidos por hidrodestilación de las partes aéreas frescas de las plantas se analizaron mediante cromatografía de gases y
cromatografía de gases-espectrometría de masas. La capacidad antioxidante se midió mediante varias pruebas químicas: DPPH, ABTS y FRAP.
Resultados: Se identificaron múltiples componentes principales, mostrando variaciones en la composición entre especies, así como entre plantas de la
misma especie. M. spicata se caracterizaba por carvona, piperitona, 1,3,8-p-menthatrieno; mientras que M. piperita presenta linalol, D-carvona, 1,3,8-p-
menthatrieno; y M. pulegium tenía un único componente principal que es la pulegona. Hasta donde sabemos, se supone que puede definirse un nuevo
conjunto de quimiotipos en función de las regiones geográficas estudiadas. Los aceites esenciales examinados demostraron una notable eficacia
antioxidante.
Conclusiones: Estos hallazgos sugieren el uso potencial de los extractos de estas plantas como alternativa a los productos químicos sintéticos. Por lo tanto,
podrían encontrar aplicaciones en medicina complementaria, así como en las industrias farmacéutica y alimentaria.
Palabras Clave: aceites esenciales; capacidad antioxidante; composición química; Mentha piperita; Mentha pulegium; Mentha spicata.
ARTICLE INFO AUTHOR INFO

Received: November 21, 2023. ORCID: 0009-0003-7821-0112 (AR) 0000-0001-7610-789X (MA)
Accepted: March 17, 2024. 0000-0002-9927-8947 (OC) 0000-0002-6908-843X (EA)
Available Online: May 31, 2024. 0000-0002-7235-2887 (ERA) 0009-0001-0096-4083 (DA)
Rayan et al. Chemical composition and antioxidant capacity of Mentha essential oils from Morocco
Abbreviations: ABTS: 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid); A.F.N.O.R: the standards organization of France; BHA:
butylated hydroxyanisole; BHT: butylated hydroxytoluene); DMSO: dimethylsulfoxide; DPPH: 2,2-diphenyl 1-picrylhydrazyl; EOs:
essential oils; FID: flame ionization detector; FRAP: ferric reducing antioxidant power assay; IC50: Inhibitory concentration of 50%; GC: gas
chromatography; GC-MS: gas chromatography-mass spectrometry; RI: retention index.
INTRODUCTION al., 2001). These environmental factors and plant

characteristics are important criteria for studying the
Mentha is a plant that is indigenous to the Mediter- activity of essential oils.
ranean region. It is cultivated worldwide for its di-
verse applications. It belongs to the Lamiaceae family The purpose was to evaluate the chemical compo-
and has a variety of species, which are widely distrib- sition by gas chromatography (GC) and gas chroma-
uted and cultivated in temperate tropical regions tography-mass spectrometry (GC-MS) of M. spicata,
(Fazili et al., 2020). It is extensively used in Mediter- M. piperita and M. pulegium, and analyze their variabil-
ranean regions as a food flavoring and for therapeutic ities according to three different geographical areas in
purposes to treat common colds, stomachaches, hem- the Rabat-Sale-Kenitra region. In addition, the aim
orrhoids, and upper respiratory tract infections (Ta- was to evaluate the physicochemical parameters and
waha et al., 2007). Nowadays, it is considered to be an antioxidant capacity of these EOs.
industrial product, with its essential oils being used in
the pharmaceutical, food, beverage, confectionery, MATERIAL AND METHODS
toothpaste, mouth freshener, and cosmetics industries
(Alsaraf et al., 2021). Chemicals and reagents
Mentha spicata (spearmint), Mentha pulegium (pen- The chemicals and reagents used in this investiga-
nyroyal mint), and Mentha piperita (peppermint) are tion included 2,2-diphenyl-1-picrylhydrazyl (DPPH),
the most important aromatic medicinal plants within 2,2'-azino-bis acid (ABTS), Ferric reducing antioxidant
this genus. The extracts derived from these plants power assay (FRAP), dimethyl sulfoxide (DMSO),
have been extensively studied for their antibacterial, quercetin, catechin, and ascorbic acid, all obtained
antifungal, anti-inflammatory, and antioxidant prop- from Sigma-Aldrich (St. Louis, MO, USA). Addition-
erties (Arrahmouni et al., 2023; Boukhobza, 2020; ally, potassium ferricyanide (K3Fe (CN)6), phosphate
Chraibi et al., 2016). buffer, trichloroacetic acid, potassium persulfate, an-
hydrous sodium sulfate, and methanol were acquired
M. spicata, M. pulegium and M. piperita essential
from COGELAB (Morocco).
oils (EOs) are diverse mixtures of phenolics, tannins,
terpenes, terpenoids, quinones, coumarins, flavo- Plant material
noids, alkaloids and sterols (Ait-Sidi-Brahimet al.,
2019; El-Gharbaouiet al., 2017). Studies have shown The three mint varieties: M. spicata, M. piperita and
that M. pulegium has highly efficacious antifungal M. pulegium were collected from three different areas
activity against Candida albicans, inhibiting biofilm in the Rabat-Sale-Kenitra region. Samples from the
formation, growth, transition, and the expression of Akkari area (34˚00΄29″N 6˚51΄19″W) were collected
virulence-related genes (Benzaid et al., 2019). Other during July 2022, while samples from Sidi Ayach
studies highlighted the bactericidal power of M. spi- (34˚19΄59″N 6˚27΄26″W) and Ain Atiq (33˚53΄38″N
cata and M. piperita, and the possibility of using their 6˚58΄00″W) areas were collected during October-
EOs as natural antibiotics (Ben Lagha et al., 2020; Ra- November 2022. Botanical identification of the plant
sooli et al., 2009). The antioxidant properties of EOs material was conducted at the Department of Botany,
and their constituents have been widely studied by Faculty of Sciences and Techniques of Errachidia
several researchers, who have revealed that these EOs (FSTE). The extraction of EOs was carried out using
can be used as natural antioxidants to replace butylat- the leaves of M. spicata and M. piperita, as for M.
ed hydroxytoluene (BHT) and butylated hydroxyani- pulegium, the aerial floral parts were used.
sole (BHA) and other synthetic conservants that are
known to pose risks to human health (Kahl and Kap- Extraction
pus, 1993; Ouedrhiri et al., 2021; Singh et al., 2015). A total of 500 g of each botanical material under-
However, the composition of the extracted prod- went hydrodistillation in 1 L of distilled water for a
ucts (EOs) can be altered by several factors influenc- duration of 3 h utilizing a Clevenger-type apparatus
ing the plant, such as climate, soil composition, plant as per the guidelines outlined in the European Phar-
organ, age, and stage of the vegetation cycle, as well macopoeia (Council of Europe, 2007). Subsequently,
as by different species and chemotypes, and the EO the EOs obtained were dried using anhydrous sodi-
extraction technique (Elbouny et al., 2022; Palá-Paúl et um sulfate and preserved in light-proof bottles at a
temperature of 4 ± 1°C until further use.
https://jppres.com J Pharm Pharmacogn Res (2024) 12(6): 1022
Gas chromatography (GC) and gas chromatography- µM). The mixture was vortexed and incubated at
mass spectrometry (GC-MS) analysis room temperature for 20 min. The absorbance of the
samples was measured at 517 nm against a control. A
GC and GC-MS were used to analyze the essential
control was also prepared using DMSO and DPPH
oil that was obtained.
solution. Quercetin served as a standard antioxidant,
GC following the same conditions as the EOs (Sahin et al.,
2004). The test was conducted in triplicate, and the
GC analyses were performed using a Shimadzu percentage of inhibition was calculated using the
GC-2010 Plus gas chromatograph equipped with a following equation [1].
flame ionization detector (FID) and a DB-5 capillary
Acontrol - Asample
column (30 m × 0.25 mm i.d., film thickness 0.25 μm Inhibition (%) =
Acontrol)
*100 [1]
SGE Ltd). The oven temperature was programmed to
Where: Acontrol: Absorbance of the mixture containing the DPPH solu-
increase from 60°C to 200°C, 3°C.min-1, followed by
tion with the DMSO used to solubilise the samples. Asample: Absorbance
an isothermal hold for 5 minutes. of the mixture containing the DPPH solution and the sample.
The injector and detector temperatures were set at The results were expressed as an inhibitory con-
280°C and 300°C, respectively. The carrier gas, nitro- centration of 50% DPPH (IC50) using the regression
gen, was adjusted to achieve a linear velocity of 30 equation obtained by plotting the concentration as a
cm/s. Sample injection was performed using a split function of the percentage of inhibition.
sampling technique with a ratio of 1:50. The injection
volume was 0.2 μL of a pentane-volatile solution (1:1). FRAP test
GC-MS This assay is based on the reduction of ferric iron

(Fe3+) to ferrous iron (Fe2+). The FRAP reagent and
The GC-MS unit utilized a Shimadzu GC-2010 gas concentrations of EOs were prepared. To perform the
chromatograph, equipped with a BP-5 capillary col- assay, 0.2 mL of each sample, 2.5 mL of phosphate
umn (30 m × 0.25 mm i.d., film thickness 0.25 μm; buffer (0.2 M and pH = 6.6), and 2.5 mL of 1% (w/v)
SGE, Ltd.), and interfaced with a Shimadzu QP2010 potassium ferricyanide complex (K3Fe (CN)6) were
Plus mass spectrometer (software version 2.50 SU1). mixed and incubated at 50°C for 20 min. After adding
The oven temperature was programmed following 2.5 mL trichloroacetic acid at 10%, absorbance was
the described parameters for GC analysis. The trans- measured at 700 nm (Oyaizu, 1986). The test was car-
fer line temperature was set at 300°C, ion source tem- ried out in triplicate. The results were obtained by
perature at 200°C, and the carrier gas (helium) adjust- plotting the concentration as a function of the absorb-
ed to a linear velocity of 36.5 cm/s. The split ratio was ance of the sample. The effective concentration of 50%
1:40, ionization energy was at 70 eV, the scan range Fe3+ to Fe2+ (EC50) was obtained by exploiting the re-
was from 40 to 400 m/z, and the scan time was 1 s. gression equation obtained. Consequently, the results
Component identification was achieved by com- obtained were compared with those of the catechin,
paring their retention indices relative to C9-C20n which were taken as reference standards.
alkanes on the DB-5 column (Adams, 2007), further
confirmed through a comparison of recorded mass ABTS test
spectra with those available in a computer library The antioxidant capacity of EOs was also assessed
(Shimadzu corporation library and NIST05 data- by ABTS. The ABTS reagent was prepared 16 h before
base/ChemStation data system), as well as from a the manipulation by mixing 10 mL of a 7 mM meth-
home-made library. The latter was constructed based anolic solution of ABTS and 10 mL of a 70 mM meth-
on analyses of reference oils, laboratory-synthesized anolic solution of potassium persulfate. This solution
components, commercially available standards, and was then diluted with methanol until an absorbance
other literature data (Elouaddari et al., 2019; Laseve, between 0.700 and 0.734 nm was obtained. Successive
1996). concentrations of extracts were prepared in DMSO
and mixed with the reagent. After incubation for 1
Antioxidant capacity min at room temperature, absorbance was registered
at 734 nm (Pukalskas et al., 2002). The test was per-
DPPH test formed in triplicate, and the percentage inhibition
The test is based on DPPH free radical scavenging. was calculated using the equation [1], as the DPPH
The EO samples were solubilized in DMSO, and suc- test. The results were expressed as an inhibitory con-
cessive dilutions were prepared from the initial ex- centration of 50% ABTS (IC50) using the regression
tract. Subsequently, 50 µL of each EO dilution was equation obtained by plotting the concentration as a
mixed with 2 mL of methanolic DPPH solution (60 function of the percentage of inhibition. In addition,

the results obtained were compared with those of Statistical analysis

ascorbic acid, which was taken as a reference stand-
The experiments were performed in triplicate, and
ard.
the results were presented as the mean ± standard
deviation (SD). Statistical analysis and mean compari-
Analytical study of EO
sons were conducted using GraphPad Prism v8 soft-
ware, utilizing one-way analysis of variance
Organoleptic properties of EOs
(ANOVA) followed by the Tukey test. Statistical sig-
The various organoleptic characteristics (flavor, nificance was considered for p-values less than 0.05.
color, and odor) of different varieties of EOs were
evaluated. RESULTS
Measurement of physicochemical parameters Organoleptic properties of EOs

The analyses were carried out in accordance with Odor, color, and flavor were evaluated. The results
AFNOR standards (AFNOR, 1998) as physical charac- are shown in Table 1.
teristics: density, refractive index, rotatory power, and
chemical characteristics: acid value, ester value, sa- Variation in physicochemical parameters
ponification value, and peroxide value. The test was
evaluated in triplicate, and the results were presented The results of the physicochemical parameters are
as mean ± standard deviation. presented in Table 2.
Table 1. Organoleptic characteristics of the EOs studied.
Sample Origin Odor Color Flavor
M. spicata Ak + Yellow Minty +

SA ++ Yellow Minty +
AA + Yellow Minty +
M. piperita Ak ++ Yellow Minty ++

SA ++ Yellow Minty++
AA ++ Translucent Minty++
M. pulegium Ak +++ Green-yellow Minty +++
SA +++ Green-yellow Minty +++
AA +++ Green-yellow Minty +++

Ak: Akkari; SA: Sidi Ayach; AA: AinAtiq.
Table 2. Yield and physicochemical parameters of Mentha species EOs.
D AV SV EV PV
Origin Y% RI RP
(g/mL) (mg KOH/g) (mg KOH/g) (mg KOH/g) (mg Eq 02/g)
M. spicata
Akkari 1.10 0.892 ± 0.02a 1.478 ± 0.04a -59 ± 0.04a 1.30 ± 0.19a 112.20 ± 0.45a 110.90 ± 0.89a 0.739 ± 0.02a
Sidi Ayach 0.63 0.865 ± 0.01a 1.478 ± 0.10a -68 ± 0.12b 0.09 ± 0.02b 84.15 ± 0.32b 84.06 ± 0.68b 0.459 ± 0.06b
Ain Atiq 0.63 0.878 ± 0.03 a

1.462 ± 0.02 a
-44 ± 0.22 c
0.09 ± 0.01 b
56.10 ± 0.07 c
56.01 ± 0.33 c
0.520 ± 0.03c
M. piperita
Akkari 0.50 0.929 ± 0.07a 1.460 ± 0.05 a -17 ± 0.07 a 1.20 ± 0.03 a 56.10 ± 0.09 a 54.90 ± 0.10 a 1.33 ± 0.10 a
Sidi Ayach 0.15 0.931 ± 0.03a 1.469 ± 0.01 a -26 ± 0.05b 0.65 ± 0.03b 56.10 ± 0.11 a 55.45 ± 0.07b 1.23 ± 0.09 a
Ain Atiq 0.15 0.909 ± 0.01 a

1.461 ± 0.02 a
-21 ± 0.01 c
0.60 ± 0.03 b
78.54 ± 0.10 b
77.94 ± 0.10 c
1.45 ± 0.07 a
M. pulegium
Akkari 1.75 0.938 ± 0.11a 1.485 ± 0.07a +21 ± 0.54a 2.36 ± 0.15 a 14.02 ± 0.8a 11.66 ± 0.35a 8.02 ± 0.10a
Sidi Ayach 1.47 0.954 ± 0.10a 1.486 ± 0.04a +21 ± 0.23a 2.00 ± 0.13a 42.07 ± 0.34b 40.07 ± 0.67 b 5.44 ± 0.13b
Ain Atiq 0.80 0.925 ± 0.09 a

1.485 ± 0.02 a
+16 ± 0.29 b
1.12 ± 0.17 b
22.44 ± 0.045 c
20.03 ± 0.57 c
5.00 ± 0.23b
Y: Yield; D: Density; RI: Refractive index; RP: Rotating power; AV: Acid value; SV: Saponification value; EV: Ester value; PV: Peroxide value. Results were expressed as mean ±
standard deviation (n = 3). Values in the same column with different superscript letters indicate significant differences (p<0.05).

Ain Atiq area

Chemical composition
Table 5 lists the retention indices and percentage
Akkari area composition of the identified compounds in the M.
spicata, M. piperita and M. pulegium EOs collected in
Table 3 presents the retention indices and percent-
the Ain Atiq area.
age composition of the identified compounds in the
EOs of M. spicata, M. piperita, and M. pulegium, respec- The chemical analysis of the EOs of M. spicata re-
tively, collected from the Akkari area. vealed 17 components representing 100% of the EO.
The major components were piperitone (77.84%),
Regarding M. spicata, significant variations in
5methyl-hexanoic acid (5.61%), benzene acetaldehyde
chemical composition were observed among plant
(2.69%), citronellol (2.49%) and maltol (2.29%)(Table
populations. Fifteen compounds, constituting 100% of
5, Fig. 3A).
the oil, were identified. The primary constituents
included carvone (58.16%), limonene (22.4%), 1,8- Regarding M. piperita, 24 components were identi-
cineole (6.84%), and β-myrcene (3.51%). The chroma- fied; they amount to 100% of the EOs. The most im-
togram in Fig. 1 illustrates the GC-MS analysis (Fig. portant constituents are as follows: 1,3,8-ρ-mentha-
1A). triene (56.34%), 2-(1E)-propenyl-phenol (13.96%), cis-
piperitol (8.19%), (E)-α-damascone (3.95%), trans-ρ-
A total of 25 constituents representing 98.59% of
menth-6-en-2,8-diol (1.95%) and pulegone (1.28%)
the total EOs of M. piperita were identified. The main
(Table 5, Fig. 3B).
components were linalool (59.34%), linalool acetate
(12.59%), α-terpineol (6.93%), 1,8-cineole (3.57%), 1- The results drawn from M. pulegium showed 20
tetradecene (3.49%), and geraniol (2.48%) (Table 3, constituents representing 100% of the EOs. A signifi-
Fig. 1B). cant proportion of pulegone (75.34%) was observed.
Other components were identified with lower per-
Regarding M. pulegium, 28 constituents represent-
centages, namely terpineol (7.06%), mentho thiophene
ing 99.75% of the total EOs were identified. The main
(4.94%), 1-tridecene (1.81%), and menthol (1.55%)
components were the pulegone, which represents
(Table 5, Fig. 3C).
(49.88%), isomenthone (25.26%), and cis-β-ocimene
(4.28%) (Table 3, Fig. 1C).
Antioxidant capacity
Sidi Ayach area
DPPH
Table 4 lists the retention indices and percentage
The results of the DPPH antioxidant capacity
composition of the compounds identified in the M.
showed better performance of M. spicata from the Ain
spicata, M. piperita, and M. pulegium EOs collected
Atiq area, followed by M. piperita from the Sidi Ayach
from the Sidi Ayach area.
area. However, this activity was significantly lower
In regard to M. spicata, 21 components represent- (p˂0.05) than the commercial standard used, querce-
ing 100% of the EOs were identified. The major com- tin (0.0054 ± 0.0001 mg/mL). On the other hand, some
ponents were piperitone (36.68%), 1,3,8-ρ-mentha- EOs were inactive under this technique (Table 6).
triene (25.68%), 2-(1E)-propenyl-phenol (5.27%),
5methyl-hexanoic acid (4.99%), menthan-2-one ABTS
(3.27%), cis-piperitol (3.09%) (Table 4, Fig. 2A).
In terms of M. spicata varieties, the Sidi Ayach area
The chemical composition of M. piperita revealed showed the highest antioxidant capacity. However, as
19 components representing 100% of the EOs. This to M. piperita, the Ain Atiq area demonstrated signifi-
peppermint variety was dominated in this case by D- cantly high (p˂0.05) activity, while the Sidi Ayach and
carvone (56.75%), citronellol (11.03%), maltol Akkari areas were inactive. Nevertheless, the best
(10.38%), 5-methyl-hexanoic acid (7.39%), and 2-(1E)- antioxidant capacity was recorded in the Sidi Ayach
propenyl-phenol (1.73%) (Table 4, Fig. 2B). area variety of M. pulegium, followed by Ain Atiq and
Akkari. All varieties had significantly low (p˂0.05)
About M. pulegium, 21 components were identi-
antioxidant capacity compared with the ascorbic acid
fied, representing 99.99% of the EOs. The predomi-
standard used (0.0025 ± 0.0002 mg/mL) (Table 6).
nant component was pulegone, accounting for
81.54%, with the other remaining components listed
FRAP
as follows: Mentho thiophene (4.32%), pentyl-benzene
(2.57%), 1-tridecene (1.96%) and, menthol (1.04%) According to Table 6, all the samples studied ex-
(Table 4, Fig. 2C). hibited activity. Concerning M. spicata, two varieties,

from the Sidi Ayach and Akkari areas, demonstrated cantly the highest activity (p<0.05), followed by Sidi
significantly high activity (p<0.05). Ayach and Ain Atiq. On the other hand, catechin
showed significantly higher (p˂0.05) antioxidant ca-
In the case of M. piperita, the most notable activity
pacity than the other samples (0.013 ± 0.0025
was observed in the Sidi Ayach EOs, showing a sig-
mg/mL).
nificant difference (p<0.05) compared to the others.
For M. pulegium, the Akkari variety displayed signifi-
Table 3. Chemical composition of the EOs of the M. spicata, M. piperita, and M. pulegium
collected from the Akkari area.
Component RIa RIb Percentage
M. spicata
α-Pinene 942 932 1.32

Camphene 956 946 0.16
Sabinene 982 969 0.91

β-Pinene 986 974 1.76
β-Myrcene 1001 988 3.51
α-Phellandrene 1004 1002 0.25

Limonene 1035 1026 22.40
Eucalyptol 1037 1039 6.84
Borneol 1169 1165 0.35

trans-Dihydrocarvone 1202 1200 2.01
Citronellol 1224 1223 0.56
Pulegone 1243 1233 0.29
Carvone 1251 1239 58.16
β-Caryophyllen 1422 1417 0.67

D-Germacrene 1484 1484 0.81
M. piperita
β-Pinene 981 974 0.17

β-Myrcene 1001 988 2.60
Limonene 1034 1024 0.52

β-trans-Ocimene 1043 1044 0.73
γ-Terpinene 1053 1054 0.40
Terpinolen 1078 1086 0.14

Linalool 1109 1095 59.34
trans-Thujone 1112 1112 0.22
1-Octen-3-yl-acetate 1119 1117 0.17
trans-Pinocarveol 1131 1135 0.20

Isomenthone 1158 1153 0.16
α-Terpineol 1196 1186 6.93
Pulegone 1234 1233 0.97
p-Anisaldehyde 1243 1247 0.44
Geraniol 1261 1249 2.48

Linalool acetate 1263 1254 12.59

Table 3. Chemical composition of the EOs of the M. spicata, M. piperita, and M. pulegium
collected from the Akkari area (continued...)
Geranial 1276 1264 0.13

Eugenol 1356 1356 0.42
α- Copaene 1373 1374 1.71

1-Tetradecene 1392 1388 3.49
(Z)-Caryophyllene 1397 1409 0.13

α-trans-Bergamotene 1422 1432 0.26
Hedycaryol 1554 1546 0.53

1-Hexadecene 1593 1588 0.29
M. pulegium
α-Pinene 941 932 0.90
β-Pinene 981 974 1.64

β-Myrcene 1001 974 0.70
alpha-Phellandrene 1004 988 0.24
cis-beta-Ocimene 1034 1002 4.28

trans-beta-Ocimene 1043 1039 0.53
Linalool 1107 1044 0.47

Isomenthone 1158 1095 25.26
Borneol 1168 1153 3.04
alpha-Terpineol 1180 1165 2.87
Pulegone 1245 1186 49.88
Linaloolacetate 1259 1232 1.30

Geranial 1267 1254 0.13
Bornyl acetate 1286 1264 0.12
2-Undecanone 1293 1284 0.45
Terpinylacetate 1343 1293 1.39
alpha Copaene 1370 1346 1.97

1-Tetradecene 1397 1374 0.12
beta-Caryophyllene 1422 1388 1.03

alpha-Caryophyllene 1456 1417 0.18
Humulene alpha 1465 1444 0.32
Germacrene D 1484 1452 1.26

delta-Cadinene 1527 1484 0.41
Spathulenol 1579 1522 0.14
Caryophyllene oxide 1584 1577 0.21
beta-Himachalenoxide 1618 1582 0.14

a
Experimental Linear retention index. bRelative Linear retention index to C9–C22n-alkanes on the DB-5 column
taken from (Adams, 2007) for DB-5 capillary column in literature.

Figure 1. GC-MS chromatogram analysis of M. spicata (A), M. piperita (B), and M. pulegium (C) EOs collected from the Akkari area.
Table 4. Chemical composition of the EOs of M. spicata, M. piperita and M. pulegium

collected from the Sidi Ayach area.
M. spicata
α-Pinene 940 932 0.35

cis-Pinane 985 984 0.89
meta-Mentha-1(7),8-diene 1000 1000 2.55
5methyl-Hexanoic acid 1034 1033 4.99
Benzene acetaldehyde 1036 1036 3.60

γ-Hexalactone 1042 1042 0.81
Isopoentyl butanoate 1053 1052 0.38

1,3,8-ρ-Menthatriene 1108 1108 25.68


collected from the Sidi Ayach area (continued...)
1-Terpineol 1130 1130 0.90
cis-Piperitol 1195 1195 3.09
Menthan-2-one 1200 1199 3.27
cis-4-Caranone 1201 1201 1.90

Piperitone 1250 1249 36.86
(2E)- Decenal 1261 1260 1.42

2-(1E)-propenyl-Phenol 1263 1264 5.27
Linalool propanoate 1334 1334 1.20

Trans-Menth-6-en-2,8-diol 1372 1371 0.64
(E)-α-Damascone 1391 1392 1.33
ρ-Menth-1-en-9-ol acetate 1421 1421 1.35
α-Amorphene 1483 1483 0.78
M. piperita
cis-Pinane 985 982 0.73

meta -Mentha-1(7),8-diene 1001 1000 1.48
Phellandrene 1004 1002 0.48

5-methyl-Hexanoic acid 1034 1033 7.39
Maltol 1107 1106 10.38
1-Terpineol 1131 1130 0.46

γ-Terpineol 1200 1199 1,19
trans-Dihydro carvone 1201 1201 1.06

D-Carvone 1250 1250 56.75
(2E)-Decenal 1261 1261 0.46
trans-Piperitol acetate 1344 1343 0.46

α-Isocomene 1388 1388 0.76
(E)-α-Damascone 1392 1392 0.48

α-Amorphene 1483 1483 1.25
M. pulegium
α-Pinene 940 932 0.11


Bergamal 1051 1051 0.22
Maltol 1106 1106 0.28


collected from the Sidi Ayach area (continued...)
pentyl-Benzene 1152 1152 2.57
Terpineol 1156 1156 0.70

Menthol 1167 1167 1.04
ρ-methyl-Acetophenone 1179 1179 1.75

trans-Pulegol 1213 1213 0.16
Thymol, methyl ether 1232 1232 0.23
Pulegone 1245 1245 81.54
6-Undecanol 1285 1285 0.46

1-Tridecene 1291 1291 1.96
Undecanal 1307 1305 0.44

Mentho thiophene 1342 1342 4.32
γ-Elemene 1436 1436 0.41
Maltol propionate 1455 1456 0.26

cis Cadina-1(6),4-diene 1462 1461 0.21
ar-Tumerol 1583 1582 0.17
β-Atlantol 1609 1608 0.39

a
Experimental Linear retention index. Relative Linear retention index to C9–C22n-alkanes on the DB-5
b
column taken from (Adams, 2007) for DB-5 capillary column in literature.
DISCUSSION distinctive minty odor. A difference in yield was not-

ed between the three varieties, with a higher value of
Physicochemical properties of EOs 0.50%, similar to that found in Congo (Likibi et al.,
2015). The physical and chemical characteristics of M.
According to Tables 1 and 2, hydrodistillation of piperita EOs were determined (Table 2). The results of
the aerial part of Akkari M. spicata produced yellow the obtained parameters showed significant differ-
EOs with a minty odor. A higher yield was recorded ences.
for the Akkari variety (1.10%) than for the other varie-
ties (0.63%). El Hassani et al. (2009) obtained a yield of M. pulegium EOs extracted from aerial parts are
1.20%, while Mahboubi (2021) reported that the yield characterized by an overly intense odor with a green-
varies between 2.41-2.74%. In light of this, yields are ish-yellow color. M. pulegium showed the highest
subject to variation due to several factors (Hussain et yield compared to M. spicata and M. piperita, with a
aI., 2010). The relative density results show a value value of 1.75%. However, this rate is relatively low
fluctuating around 0.80 g/mL, which is in line with compared with those reported in other studies (Ait-
previous research (Sulieman et al., 2011; Wee- Ouazzou et al., 2012; Zekri et al., 2013). Concerning
charangsan et al., 2014). Concerning the refractive physical and chemical parameters, the results showed
index, the values were almost identical, with the that each variety has its own characteristics (Table 2).
highest value of 1.478 for the Akkari and Sidi Ayach In Algeria, Hariri et al. (2020) studied the physico-
varieties, compared with 1.462 for the Ain Atiq area. chemical parameters of M. pulegium EOs. They found
The three varieties showed differences in their rotato- the following results: relative density of 0.908 g/mL,
ry power and chemical indices. For example, the acid refractive index at 20°C 1.486, rotatory power of
value was 1.30 mg KOH/g for Akkari M. spicata and +2.25, acid value of 9.537 mg KOH/g, ester value of
0.90 mg KOH/g for the other two, which does not 46.573 mg KOH/g at 20°C, and saponification value
correspond to the results found by Sulieman et al. of 56.11. Based on these findings, it is clear that the
(2011). parameters differ from one study to another and may
be influenced by several factors such as the origin of
Regarding M. piperita, the EOs extracted are char- the material, edaphic factors, and climate, among
acterized by a yellow and translucent color with a others.

Figure 2. GC-MS chromatogram analysis of M. spicata (A), M. piperita (B), and M. pulegium (C) EOs collected from the Sidi Ayach area.
Table 5. Chemical composition of the EOs of M.spicata, M. piperita, and M. pulegium collected from the Ain Atiq area.
M. spicata
α-Pinene 941 932 0.20

trans-meta-Mentha-2,8-diene 981 979 0.19
cis-Pinane 985 984 0.61

ρ-Mentha-1(7),8-diene 1004 1003 0.34

Table 5. Chemical composition of the EOs of M.spicata, M. piperita, and M. pulegium collected from the Ain Atiq area (continued...)

Maltol 1106 1106 2.29
1-Terpineol 1131 1130 0.48

Menthan-2-one 1200 1199 1.62
cis-4-Caranone 1201 1201 1.82

Piperitone 1284 1249 77.84
Linalool propanoate 1334 1334 0.50

α-Amorphene 1483 1483 0.64
M. piperita

γ-Hexalactone 1043 1042 0.88
Isopentyl butanoate 1053 1052 0.56

Linalool 1095 1095 0.29
1,3,8-ρ-Menthatriene 1108 1108 56.34
(2E)- Heptenyl acetate 1111 1111 0.16
3-Methylbutanote,3-methyl-butenyl 1115 1112 0.16

1-Terpineol 1131 1130 0.24
Pulegone 1234 1233 1.28
ρ-Anisaldehyde 1247 1247 0.55

(2E)- Decanal 1261 1260 3.88
4-Hydroxybenzaldehyde 1355 1355 0.42
trans-ρ-Menth-6-en-2,8-diol 1372 1371 1.95

(E)-α-Damascone 1392 1392 3.95
(Z)-Trimenal 1396 1397 0.36

n-Tetradecane 1400 1400 0.22
α-Amorphene 1483 1483 0.26
cis-Cadinene ether 1553 1552 1.51

Viridiflorol 1592 1592 0.39

Table 5. Chemical composition of the EOs of M.spicata, M. piperita, and M. pulegium collected from the Ain Atiq area (continued...)
M. pulegium
Bergamal 1051 1051 0.30
pentyl-Benzene 1152 1152 1.10

Terpineol 1156 1156 7.06
Menthol 1167 1167 1.55
ρ-methyl-Acetophenone 1179 1179 1.88

Pulegone 1244 1245 75.34
trans-Piperitone epoxide 1252 1252 0.28

6-Undecanol 1285 1285 0.55
1-Tridecene 1291 1291 1.81

Undecanal 1307 1305 0.37
Menthol thiophene 1342 1342 4.94
(2E)-Undecanal 1358 1357 0.30

Methyl benzyl butyrate 1363 1363 0.56
2,5-dimethoxy-ρ-Cymene 1424 1424 0.31
γ-Elemene 1436 1436 0.58
trans-Cadinene ether 1557 1557 0.36
β-Atlantol 1609 1608 0.49

a
Experimental Linear retention index. Relative Linear retention index to C9–C22n-alkanes on the DB-5 column taken from (Adams, 2007) for DB-5
b
capillary column in literature.
According to research, the yield and chemical third from the Ain Atiq area is dominated by piperi-
composition of an EO is directly affected by various tone. These major components have been cited in
factors, including temperature, relative humidity, several studies for their antimicrobial, antispasmodic,
duration of insolation and wind conditions, cultiva- anti-inflammatory and antioxidant activities
tion practices, the harvest season of the plant, extrac- (Abdolpour et al., 2007; Han et al., 2019; Pina et al.,
tion method, geographical origin, and the complexity 2022; Santana et al., 2020). In Morocco, studies carried
of the chemotype concept (Elbouny et al., 2022; Palá- out on the chemical composition of M. spicata EOs
Paúl et al., 2001; Selles et al., 2018). It should be noted that are harvested in the Settat region and the Sais
that the refractive index of EOs varies primarily with valley reported that the oil was characterized by two
the content of monoterpenes and oxygenated deriva- main components: carvone and limonene. Previous
tives (Kanko et al., 2004), indicating that the preced- studies in Algeria, Serbia, Greece, Tunisia, Iran, and
ing factors indirectly influence the physicochemical India have shown that monoterpenes, notably car-
parameters of EOs. vone, limonene, and 1,8-cineole, were the main con-
stituents of M. spicata EOs. All the previous studies
Chemical composition cited reported a similar chemical composition of M.
spicata EOs from the Akkari area (Bardaweel et al.,
The chemical composition of the EOs of the M. spi-
2018; Benomari et al., 2018; El Hassani, 2020; Fitsiou et
cata, M. piperita, and M. pulegium varieties revealed
al., 2016; Govindarajan et al., 2011; Shahbazi, 2015;
the presence of several chemotypes.
Snoussi et al., 2015; Soković et al., 2009). The third
For the varieties of M. spicata, the first chemotype chemotype, characterized by a high percentage of
from the Akkari area is dominated by car- piperitone (77.84%), was reported for the first time in
vone/limonene, the second from the Sidi Ayach area Morocco in the study, although it is a common Greek
is dominated by menthatriene/piperitone, and the
Figure 3. GC-MS chromatogram analysis of M. spicata (A), M. piperita (B), and M. pulegium (C) EOs collected from the Ain Atiq area.

Table 6. IC50 values of the EOs studied measured by various chemical tests.
Species Origen DPPH (mg/mL) ABTS (mg/mL) FRAP (mg/mL)
M. spicata AK 27.63 ± 0.1616a 25.41 ± 0.4362a 5.36 ± 0.2573a

SA Inactive 17.93 ± 0.0658b 5.22 ± 0.3084a
AA 16.44 ± 0.0392b 34.89 ± 2.4370c 8.62 ± 0.0873b

M. piperita AK 25.15 ± 0.4733c Inactive 68.39 ± 4.9820c
SA 22.86 ± 0.1384d 28.75 ± 0.7127d 9.48 ± 0.0150d

AA 58.04 ± 4.9856e 6.35 ± 0.3023e 35.87 ± 0.5147e
M. pulegium AK Inactive 5.02 ± 0.077f 7.28 ± 0.0096f
SA Inactive 1.73 ± 0.0271g 11.50 ± 0.2068g

AA Inactive 4.87 ± 0.2384f 12.59 ± 0.2546h
Quercetin - 0.0054 ± 0.0001f - -
Catechin - - - 0.013 ± 0.0025i
Ascorbic acid - - 0.0025 ± 0.0002h -

Results were expressed as mean ± standard deviation (n = 3). Values in the same column with different superscript letters indicate significant differences
(p<0.05). Ak: Akkari; SA: Sidi Ayach; AA: Ain Atiq
(Sidi Ayach area). Pulegone is an oxygenated mono-

chemotype (Kofidis et al., 2004). Additionally, based
terpene with well-known antimicrobial, anti-
on current knowledge, the second mentha-
inflammatory, and antioxidant properties (Hariri et
triene/piperitone is a new chemotype found in the
al., 2020; Rocha et al., 2019; Zougagh et al., 2019).
Sidi Ayach area and has not been described in the
Studies carried out in several regions of Morocco re-
literature before.
ported that pulegone is the main compound in M.
Regarding M. piperita, the research showed the pulegium (Bouyahya et al., 2017; Fadli et al., 2011;
presence of three chemotypes depending on the areas Lamiri et al., 2001). Luís et al. (2021) in Portugal and
studied. The Akkari area was dominated by linalool, Hajlaoui et al. (2009) in Tunisia revealed that
the Sidi Ayach area by D-carvone, and the Ain Atiq pulegone is the major component, with concentra-
area by 1,3,8-ρ-menthatriene. Studies carried out in tions of 86.64% and 61.11%, respectively. However,
Morocco, more specifically in the Taouanat and Mid- previous studies on the chemical composition of pen-
dle Atlas regions, reported that the main components nyroyal mint have revealed the presence of other
of Moroccan M. piperita EOs are menthol and men- chemotypes. In Morocco, a new chemotype was re-
thone (Derwich et al., 2010; Marwa et al., 2007). These ported rich in piperitone and piperitenone, with low
Moroccan results align with several studies (Camele levels of pulegone (Ait-Ouazzou et al., 2012). Beghidja
et al., 2021; Likibi et al., 2015; Sustrikova and Sala- et al. (2007) from Algeria found another one that is
mon, 2004). In Algeria, M. piperita is essentially com- rich in monoterpenes such as α and β pinenes, cam-
posed of menthol and menthone (Benabdallah et al., phene, sabinene, α-terpinene, and myrcene.
2018), while in Iran, it is composed of α-terpinene and
In fact, EOs compositions vary considerably due to
pipertitinone oxide (Yadegarinia et al., 2006). It is
a variety of extrinsic and intrinsic factors, such as
clear that the results diverge from those cited above.
ecological and climatic conditions, geographical loca-
In fact, da Silva Ramos et al. (2017) found that M.
tion, season of collection, stage of development, phase
piperita from Brazilian Macapa is predominantly
of plant ontogeny, ecological conditions, harvesting
composed of linalool, amounting to 51.8%, similar to
methods, post-harvest treatment of plant material and
Akkari's chemotype. Linalool and linalool-rich EOs
the method of oil extraction along with chemotypic
have been cited by several researchers as having sev-
variations (Grulova et al., 2014; Hussain et al., 2010;
eral biological activities, such as antimicrobial, anti-
Palá-Paúl et al., 2001; Selles et al., 2018). According to
inflammatory, anticancer, and antioxidant properties
the results of the present study, it can be observed
(Kamatou and Viljoen, 2008).
that the notion of chemotype, as well as the season of
The EOs of the M. pulegium samples are character- harvest, ecological conditions, and geographical loca-
ized by the presence of pulegone as the main compo- tion, played a major role in the fluctuation of the
nent, with a concentration varying between 49.88% chemical composition of the samples studied.
(Akkari area), 75.34% (Ain Atiq area), and 81.54%

Antioxidant capacity activity, which is in line with the study by Bardaweel

et al. (2018).
Antioxidants play a vital role in human health,
and they protect us from free radicals that may be The reducing power assay (FRAP) is the ability of
responsible for a number of pathogenic and chronic a natural antioxidant to donate an electron or hydro-
diseases (Alsaraf et al., 2021). Mint species, in general, gen to form a more stable product (Shimada et al.,
are considered to be safe natural antioxidants that can 1992). All the EOs studied were capable of reducing
replace synthetic alternatives due to their metabolic the Fe3+/ferric cyanide complex to the ferrous form.
richness (Fazili et al., 2020). It has been summarized The best activity was noted regarding M.spicata in the
that Mentha's high antioxidant capacity is always Sidi Ayach area with an IC50 = 5.22 ± 0.3084 mg/mL,
attributed to the presence of phenolic compounds followed by M. spicata in the Akkari area with an IC50
such as thymol, carvacrol, as well as alcohols like = 5.36 ± 0.2573 mg/mL and M. pulegium in the Akkari
citronellol and geraniol. Additionally, it exhibits par- area with an IC50 = 7.28 ± 0.0096 mg/mL. Bardaweel
ticular richness in pulegone, menthol, menthone, et al. (2018) have shown that M. spicata has great
piperitone, α-pinene, p-cymene, linalool, 1,8-cineole, power to donate electrons to reactive free radicals,
limonene, borneol (Grulova et al., 2014; Hariri et al., converting them into more stable non-reactive species
2020; Jagdale et al., 2015; Miguel, 2010). In this re- and putting an end to the free radical chain reaction.
search, antioxidant capacity was measured using
different methods to assess free radical scavenging CONCLUSION
potential (DPPH) and metal chelating potential (Fe2+
radicals) (FRAP) and ABTS. The chemical compositions of the essential oils of
M. spicata, M. piperita, and M. pulegium collected in
In the DPPH test, only the EOs of M. spicata and different geographical locations in Morocco were
M. piperita samples were able to reduce the stable determined. The observed differences have been at-
DPPH radical to yellow DPPH-H. However, the best tributed to the existence of chemotypes. In Morocco,
activity was observed in the Ain Atiq M. spicata sam- attention must be paid to commercial producers of
ple (16.44 ± 0.0392 mg/mL). Compared with the high- EOs to avoid mixing species of Mentha during plant
performance antioxidant quercetin (0.0054 ± 0.0001 harvesting, especially from the different localities.
mg/mL), M. spicata has a moderate antioxidant po-
tential. Several studies have demonstrated that M. These species of Mentha genus, which are gaining
spicata EOs are a potential source of the free radical increasing attention in the country, may potentially be
scavenger DPPH (Fitsiou et al., 2016; Ouedrhiri et al., used in the manufacture of pharmaceutical and oral-
2021; Saba and Anwar, 2018). Despite this, some stud- dental product preparations. They can also serve as
ies have reported that M. piperita has a reduction po- natural antioxidants to replace synthetic products
tential of up to 50%, even surpassing M. spicata (Dor- with toxic effects on human health. Additionally, it is
man et al., 2003; Mimica-Dukić et al., 2003). Further- suggested that the synergistic effect of these three
more, several studies present findings that differ from Mentha varieties may result in a strong antioxidant
the observed results, indicating that M. pulegium ex- capacity that surpasses the effect of synthetic prod-
hibits excellent DPPH free radical scavenging activity. ucts.
Kulisic et al. (2005) reported that the overall perfor-
mance of an antioxidant is the result of the complex CONFLICT OF INTEREST
interaction between components, producing synergis- The authors declare no conflicts of interest.
tic or antagonistic behavior. This finding aligns with
the results obtained, as several major components ACKNOWLEDGMENTS
(such as pulegone and linalool), known for their anti-
oxidant capacity, were either inactive or displayed This research did not receive any specific grant from
low activity. funding agencies in the public, commercial, or not-for-profit
sectors.
The results of the ABTS test revealed that all the
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Citation Format: Rayan A, Chadia O, Azzedine E, Abdellah M, Zakaria B, Abdelaziz E, Zahra BF, Otman E, Abdallah D, Lhousaine B (2024) A
comparative study of the chemical composition and antioxidant activity of the essential oils from three species of Mentha cultivated in Morocco. J
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© 2024 Journal of Pharmacy & Pharmacognosy Research, 12 (6), 1021-1039, 2024

A comparative study of the chemical composition and antioxidant

ARTICLE INFO AUTHOR INFO

INTRODUCTION al., 2001). These environmental factors and plant

GC-MS This assay is based on the reduction of ferric iron

https://jppres.com J Pharm Pharmacogn Res (2024) 12(6): 1023

the results obtained were compared with those of Statistical analysis

Measurement of physicochemical parameters Organoleptic properties of EOs

Table 1. Organoleptic characteristics of the EOs studied.

Sample Origin Odor Color Flavor

M. spicata Ak + Yellow Minty +

M. piperita Ak ++ Yellow Minty ++

AA +++ Green-yellow Minty +++

Table 2. Yield and physicochemical parameters of Mentha species EOs.

Ain Atiq 0.63 0.878 ± 0.03 a

Ain Atiq 0.15 0.909 ± 0.01 a

Ain Atiq 0.80 0.925 ± 0.09 a

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Ain Atiq area

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Component RIa RIb Percentage

α-Pinene 942 932 1.32

Sabinene 982 969 0.91

β-Myrcene 1001 988 3.51

α-Phellandrene 1004 1002 0.25

Borneol 1169 1165 0.35

Carvone 1251 1239 58.16

β-Caryophyllen 1422 1417 0.67

β-Pinene 981 974 0.17

Eucalyptol 1036 1036 3.57

γ-Terpinene 1053 1054 0.40

Terpinolen 1078 1086 0.14

trans-Thujone 1112 1112 0.22

1-Octen-3-yl-acetate 1119 1117 0.17

trans-Pinocarveol 1131 1135 0.20

p-Anisaldehyde 1243 1247 0.44

Geraniol 1261 1249 2.48

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Geranial 1276 1264 0.13

α- Copaene 1373 1374 1.71

(Z)-Caryophyllene 1397 1409 0.13

Hedycaryol 1554 1546 0.53

α-Pinene 941 932 0.90

β-Pinene 981 974 1.64

cis-beta-Ocimene 1034 1002 4.28

Linalool 1107 1044 0.47

alpha-Terpineol 1180 1165 2.87

Pulegone 1245 1186 49.88

Linaloolacetate 1259 1232 1.30

Terpinylacetate 1343 1293 1.39

alpha Copaene 1370 1346 1.97

beta-Caryophyllene 1422 1388 1.03

Humulene alpha 1465 1444 0.32

Germacrene D 1484 1452 1.26

Caryophyllene oxide 1584 1577 0.21

beta-Himachalenoxide 1618 1582 0.14

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Table 4. Chemical composition of the EOs of M. spicata, M. piperita and M. pulegium

Component RIa RIb Percentage