Research Article
Received: 2023-11-02 | Revised:2023-11-24 | Accepted: 2023-11-26 | Published: 2023-12-03
Pages: 95-100
DOI: https://doi.org/10.56717/jpp.2023.v02i02.021
Abstract
This study aimed to
determine the chemical composition of three essential oil samples obtained from
the leaves of M. alternifolia (Myrtaceae) collected in Kaolack (Senegal)
and to assess their in vivo anti-inflammatory activity.
The
corresponding oils were obtained by hydrodistillation and analyzed by GC/FID
and GC/MS. The anti-inflammatory activity of the essential oil was evaluated by
carrageenan-induced rat paw oedema method. Oil yields from dried leaves were
ranged from 1.5 to 1.8%. The essential oils mainly consisted of terpinen-4-ol
(28.8-33.0%), followed by
geranial (18.1-19.6%), neral (12.0-12.4%), p-cymene (9.8-11.3%) and g-terpinene (8.7-9.6%). The
essential oil administered per os very significantly prevented the development
of inflammatory edema of the rat paw induced by carrageenan at doses of 25, 50
and 100 mg/kg. The effect observed was most pronounced between 3 and 5 hours.
It was dose-dependent between 25 and 50 mg/kg. The activity at 50 mg/kg was
greater and identical to that of aspirin, used as a reference molecule and
administered at a dose of 100 mg/kg. We can conclude that the essential oil of M.
alternifolia possesses potential anti-inflammatory activity, supporting the
traditional application of this plant in treating various diseases associated
with inflammation.
Abstract Keywords
Melaleuca alternifolia, essential oils, anti-inflammatory activity, GC-MS.
1.
Introduction
Inflammation is a defense reaction of the
body to various stimuli, which can be of physical, chemical, infectious or
biological origin. Unfortunately, inflammation is accompanied by various
undesirable symptoms, e.g. edema, erythema and pain [1–3]. Their therapeutic management using
anti-inflammatories is subject to numerous adverse effects, drug interactions
and contraindications. Thus, there has recently been an increasing interest in
highly effective anti-inflammatory agents from natural sources with as little
adverse reaction as possible [1–3].
Melaleuca
alternifolia is a plant native to Australia and its
essential oil (tea tree oil; TTO) is widely used for medicinal purposes due to
its excellent antiseptic activity and antioxidant properties. TTO has a complex
chemical composition [4–8]. Six
natural chemotypes in M. alternifolia
have been described, each producing an oil of distinct chemical composition and
identified by the presence of terpinen-4-ol (terpinen-4-ol/g-terpinene/α-terpinene
[9,10] and
terpinen-4-ol/1,8-cineole/terpinolene [11]),
1,8-cineole (1,8-cineole [11];
1,8-cineole/terpinolene [11] and 1,8-cineole/terpinen-4-ol [11]) or terpinolene (terpinolene/1,8-cieneole [11,12]). The relative concentrations of the
main compounds terpinen-4-ol, 1,8-cineole and terpinolene determine the
commercial quality of the oil [13]. Thus, the aim of this study was to
characterize the chemical profile and anti-inflammatory activity of the
essential oils from leaves of M.
alternifolia collected in Kaolack (Senegal).
2.1. Plant material
Three samples of M. alternifolia fresh leaves were collected on February 19, 2023 in Kaolack (Senegal). The plant material was identified by the technicians from the Department of Botanical of the Fundamental Institute of Black Africa (IFAN) of the University Cheikh Anta Diop of Dakar.
2.2. Extraction of essential oils
Plant materials were air-dried for 14 days at room temperature. Samples were hydrodistilled (5h) using a Clevenger-type apparatus according to the method recommended in the European Pharmacopoeia [14]. The yields of essential oils (w/w, calculated on the dry weight basis) were given in Table 1.
2.3. GC and GC/MS Analysis
The chromatographic
analyses were carried out using a Perkin-Elmer
Autosystem XL GC apparatus
(Walthon, MA, USA) equipped with a dual flame ionisation
detection (FID) system and fused-silica capillary columns, namely, Rtx-1
(polydimethylsiloxane) and Rtx-wax (poly-ethyleneglycol) (60 m × 0.22 mm i.d;
film thickness 0.25 μm). The oven temperature was programmed from 60 to 230°C
at 2°C/min and then held isothermally at 230°C for 35 min: hydrogen was
employed as carrier gas (1 mL/min). The injector and detector temperatures were
maintained at 280°C, and samples were injected (0.2 μL of pure oil) in the
split mode (1:50). Retention indices (RI) of compounds were determined relative
to the retention times of a series of n-alkanes (C5–C30) by linear
interpolation using the Van den Dool and Kratz (1963) equation with the aid of
software from Perkin-Elmer (Total
Chrom navigator). The relative percentages of the oil constituents were
calculated from the GC peak areas, without the
application of correction factors.
Samples were also
analysed with a Perkin-Elmer Turbo mass
detector (quadrupole) coupled to a Perkin-ElmerAutosystem
XL, equipped with fused-silica capillary columns Rtx-1 and Rtx-Wax. The
oven temperature was programmed from 60 to 230°C at 2°C/min and then held
isothermally at 230°C (35 min): hydrogen was employed as carrier gas (1
mL/min). The following chromatographic conditions were employed: injection
volume, 0.2 μL of pure oil; injector temperature, 280°C; split, 1:80; ion
source temperature, 150°C; ionisation energy, 70 eV; MS (EI) acquired over the
mass range, 35–350 Da; scan rate, 1 s.
Identification of the
components was based on: (a) comparison of their GC retention indices (RI) on
non-polar and polar columns, determined from the retention times of a series of
n-alkanes with linear interpolation, with those of authentic compounds or literature
data; (b) on computer matching with commercial mass spectral libraries [15–17] and comparison of spectra with those of our personal
library; and (c) comparison of RI and MS spectral data of authentic compounds
or literature data.
2.4. Animals
Wistar rats (130–180 g)
of both sexes were raised in the laboratory of pharmacology and
pharmacodynamics of the Faculty of Medicine and Pharmacy of the University
Cheikh Anta Diop of Dakar. Animals were randomly assigned to groups and
maintained in plastic boxes at controlled room temperature (25–28 ◦C)
with free access to food and water, under a 12:12 h light/dark cycle. All the
experimental procedures were carried out during the day (08:00 a.m. to 05:00
p.m.) and were in accordance with the guidelines for animal care set out by the
research ethics committee of the Cheikh Anta Diop University of Dakar for
Animal Use in Research which was conducted in accordance with the
internationally accepted principles for laboratory animal use and care. The
animals submitted to oral administration of the EOMA or drugs were fasted for
12h before the experiments and acclimatized for at least 2h before the
experiments.
2.5.
Antiinflammatory activity
Carrageenan-induced rat
paw oedema is used widely as a working model of inflammation in the search for
new anti-inflammatory
drugs. The anti-inflammatory
activity of the essential oil of M. alternifolia from sample 1 was
evaluated by carrageenan-induced rat paw oedema method
[18].
The rats were divided
into 5 groups of 5 animals each. Essential oil of M. alternifolia (EOMA)
was dissolved in 0.9% NaCl solution and administered per os at different dose levels. Rats of Group I were given
normal saline (10 mL/kg, bw) and treated as negative control. Rats in Group II
were administered acetyl salicylic acid (100 mg/kg, bw) and considered as
standard. Rats from Group III to Group V were given increasing doses of
essential oil solution of M. alternifolia (25, 50, 100 mg/kg, bw). Acute paw
edema was induced by injecting 0.1 mL of 1% (w/v) carrageenan solution,
prepared in normal saline. After 1 h, 0.1 mL, 1% carrageenan suspension in 0.9% NaCl solution was injected into the sub-plantar
tissue of the left hind paw. The linear paw circumference will be measured at hourly intervals for 5 h. The increased edema was measured using digital
calliper 60, 180 and 300 min (T1h, T3h and T5h) after carrageenan injection.
The importance of edema was assessed by determining the mean percentage increase (%INC) of linear paw diameter according to the following formula:
Dt
= Paw diameter at t time
D0 = Initial paw diameter
2.6. Statistical analysis
The means of contortions in treated groups were compared
to the control with the Student t-test. A value of p < 0.05 had been
considered as significant and n = 5 represent the number of rats in each group.
The means of rat hind paw volumes were
compared by an analysis of variance (ANOVA), in order to prove homogeneity
between groups.
The means of percentages of
rat hind paw oedema variations at 1 and 5 h were also compared to control group
with t-test. A value of p < 0.05 had been considered significant and n = 5 represents the number of rats in each group. Statistical analysis was done
using a GraphPad Prism 5 software.
3.
Results and discussion
3.1 Chemical composition of essential oils
The
essential oil yields, calculated with relative to the mass of dry plant
material, were between 1.5 and 1.8%. The analysis of the leaf essential oils by
GC/FID and GC/MS allowed the identification of 12 compounds accounting for 95.9
to 98.4% of the total compositions (Table 1). Essential oils were dominated by
oxygenated monoterpenes (62.8-64.9%) and hydrocarbon monoterpenes (31.5-33.5%).
The essential oils mainly consisted of terpinen-4-ol (28.8-33.0%), followed
by geranial (18.1-19.6%), neral (12.0-12.4%), p-cymene (9.8-11.3%) and g-terpinene (8.7-9.6%). To our knowledge, we report for
the first time this chemotype in M.
alternifolia. Apart from terpinen-4-ol, a characteristic compound of this
species, geranial and neral were present at significant levels. In addition, a-terpinene, one of the constituents of the most common
chemotype (terpinene-4-ol/γ-terpinene/α-terpinene) of this species [19–22], was
among the dominant components. However, we note the absence of g-terpinene. p-Cymene,
present at a significant level in our study, was reported by two studies as
being part of the majority components of M.
alternifolia: in Slovakia (15%) [23] and in
Brazil (20%) [24].
Table 1. Chemical composition of the essential oils of Melaleuca alternifolia
|
Na |
Compounds |
lRIb |
RIac |
RIpd |
1 |
2 |
3 |
|
1 |
α-Thujene |
929 |
922 |
1023 |
2.1 |
1.9 |
2 |
|
2 |
α-Pinene |
963 |
931 |
1015 |
1.7 |
1.7 |
1.5 |
|
3 |
β-Pinene |
978 |
974 |
1108 |
1.8 |
1.5 |
1.4 |
|
4 |
Myrcene |
1007 |
982 |
1154 |
2.3 |
2.3 |
1.9 |
|
5 |
p-Cymene |
1010 |
1013 |
1264 |
11.3 |
9.8 |
10.5 |
|
6 |
Limonene |
1022 |
1021 |
1200 |
2.9 |
2.9 |
2.6 |
|
7 |
g-Terpinene |
1046 |
1048 |
1239 |
8.7 |
9.6 |
8.8 |
|
8 |
Terpinolene |
1077 |
1080 |
1278 |
2.7 |
3.4 |
2.8 |
|
9 |
Terpinen-4-ol |
1161 |
1163 |
1590 |
33.0 |
28.8 |
30.8 |
|
10 |
Neral |
1215 |
1214 |
1679 |
12.0 |
12.4 |
11.6 |
|
11 |
Geraniol |
1235 |
1233 |
1843 |
1.8 |
2.8 |
2.8 |
|
12 |
Geranial |
1244 |
1247 |
1731 |
18.1 |
18.8 |
19.6 |
|
|
Compound Classes |
|
|
|
|||
|
Hydrocarbon monoterpenes |
33.5 |
33.1 |
31.5 |
||||
|
Oxygenated monoterpenes |
64.9 |
62.8 |
64.8 |
||||
|
Total identified (%) |
98.4 |
95.9 |
96.3 |
||||
|
Yields (w/w vs dry material) |
1.8 |
1.5 |
1.6 |
||||
|
|
a
Order of elution is given on apolar column (Rtx-1). b
Retention indices of literature on the apolar column (lRIa) [25]. c Retention
indices on the apolar Rtx-1 column (RIa). d
Retention indices on the polar Rtx-Wax column (RIp). |
||||||
3.2. Antiinflammatory activity
The results of in-vivo anti-inflammatory activity of
the essential oil of M. alternifolia
(EOMA) from sample 1 on carrageenan induced edema on rat’s paw are given in Fig.
1.
The EOMA administered per os very significantly
prevented the development of inflammatory edema of the rat paw induced by
carrageenan at doses of 25, 50 and 100 mg/kg. The effect observed was most
pronounced between 3 and 5 hours. It was dose-dependent between 25 and 50
mg/kg. The activity at 50 mg/kg was greater and identical to that of aspirin,
used as a reference molecule and administered at a dose of 100 mg/kg.
In this connection, it should be noted that the 5
major components of the oil, of terpinen-4-ol (33.0%), geranial (18.1%), neral
(12.0%), p-cymene (11.3%) and g-terpinene (8.7%)
are reported to have anti-inflammatory properties. Terpinen-4-ol, the main
component of the essential oil of M.
alternifolia, suppresses inflammatory mediator production by activating human
monocytes [26]. Terpinen-4-ol can suppress the
production of inflammatory mediators in LPS-stimulated human macrophages [27]. Recently, terpinen-4-ol has been shown to have an
anti-arthritic effect which may be attributed to the downregulation of
pro-inflammatory cytokines [28]. Citral, chiral
enantiomers of neral and geranial, reduce the nociceptive and inflammatory
response in rodents [29]. Citral also
inhibits oxidative activity, nuclear factor kappa B (NF-κB) activation,
and cyclooxygenase-2 (COX-2) expression [30]. Neral has been
shown to have more potent anti-inflammatory activity than geranial, including
significant inhibition of cytokine secretion (TNF-α, IL-6 and IL-1β) and expression
of inflammatory molecules (pro-IL-1β, iNOS, COX-2
and NLRP-3) of LPS-stimulated macrophages [3]. p-cymene has been reported to
possess antinociceptive and anti-inflammatory activities [31–33]. Studies have shown that, in
different models of inflammation, g-terpinene treatment attenuated inflammatory parameters such as edema and
pro-inflammatory cytokine production, as well as cell migration into the
inflamed site [34].
Figure 1. Effect of Essential Oil of M. alternifolia on Rat Paw Oedema
Thickness in Carrageenan Model. **p < 0.01, ***p < 0.001, ****p <
0.0001 Vs Control Group. EOMA: Essential oil of M. alternifolia; ASA: Acetylsalicylic Acid
4. Conclusions
This study reported for the first time the chemical composition and anti-inflammatory activities of essential oils of M. alternifolia from Senegal. The essential oils mainly consisted of terpinen-4-ol, geranial, neral, p-cymene and g-terpinene, exhibit anti-inflammatory activity at low doses in a model of carrageenan-induced inflammatory edema in rats. The EOMA possesses potential anti-inflammatory activity, supporting the traditional application of this plant in treating various diseases associated with inflammation. In perspective, we will carry out a study of the chemical variability of the essential oils of M. alternifolia in Senegal, as well as the evaluation of other biological activities.
Abbreviations
EOMA: Essential oil of M. alternifolia; Per os: Route of administration of medication by mouth.
Authors’ contributions
Designed and coordinated the study, Y.T.; M.S.; A.W.; J.P.; J.C.; carried out the extraction and chemical characterization of essential oils, Y.T.; A.D.; C.G.; I.N.; B.N.; A.W.; J.C.; J.P.; evaluated the anti-inflammatory activity of this oil, M.S.
Acknowledgements
The authors would like to thank the technical staff of the Pharmacology Laboratory Mbassa Ndiaye who greatly facilitated the realization of the manipulations.
Funding
No funding has been received for this study
Availability of data and materials
All data will be made available on request according to the journal policy.
Conflicts of interest
Authors have no conflict of interest.
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Abstract
This study aimed to
determine the chemical composition of three essential oil samples obtained from
the leaves of M. alternifolia (Myrtaceae) collected in Kaolack (Senegal)
and to assess their in vivo anti-inflammatory activity.
The
corresponding oils were obtained by hydrodistillation and analyzed by GC/FID
and GC/MS. The anti-inflammatory activity of the essential oil was evaluated by
carrageenan-induced rat paw oedema method. Oil yields from dried leaves were
ranged from 1.5 to 1.8%. The essential oils mainly consisted of terpinen-4-ol
(28.8-33.0%), followed by
geranial (18.1-19.6%), neral (12.0-12.4%), p-cymene (9.8-11.3%) and g-terpinene (8.7-9.6%). The
essential oil administered per os very significantly prevented the development
of inflammatory edema of the rat paw induced by carrageenan at doses of 25, 50
and 100 mg/kg. The effect observed was most pronounced between 3 and 5 hours.
It was dose-dependent between 25 and 50 mg/kg. The activity at 50 mg/kg was
greater and identical to that of aspirin, used as a reference molecule and
administered at a dose of 100 mg/kg. We can conclude that the essential oil of M.
alternifolia possesses potential anti-inflammatory activity, supporting the
traditional application of this plant in treating various diseases associated
with inflammation.
Abstract Keywords
Melaleuca alternifolia, essential oils, anti-inflammatory activity, GC-MS.
This work is licensed under the
Creative Commons Attribution
4.0
License (CC BY-NC 4.0).
Editor-in-Chief
This work is licensed under the
Creative Commons Attribution 4.0
License.(CC BY-NC 4.0).