Download 3.1. Myrtus communis L. essential oil compositions

Abstract
Since synthetic antimicrobial agents and food additives can cause a number of adverse
effects, there is a growing interest from consumers in ingredients from natural sources.
Medicinal plants, such as Myrtus communis L. are a source of new compounds which can be
used in both the food industry and for medical purposes, primarily as antimicrobial agents. In
this review, the characteristics of myrtle essential oils and extracts are summarized, with
particular attention to their chemical composition, biological activities and potential
applications.
Keywords
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Myrtus communis L.;
Essential oils;
Plant extracts;
Antimicrobial activity;
Antioxidative activity
1. Introduction
Myrtle (Myrtus communis L.) is a medicinal plant endemic to the Mediterranean area and it
has been used by locals for its culinary and medicinal properties since antiquity ( Atzei 2003).
This is a well-established tradition in many countries however, despite the increasing
scientific interest in this field, there is a lack of summarized data on herbal medicine
composition, therapeutical applications and risks connected to their consumption. Therefore,
this review summarizes results regarding chemical composition and biological activities of
M. communis L.
1.1. Myrtus communis L.
Common myrtle belongs to the Myrtaceae family, which comprises approx. 145 genera and
over 5500 species ( Snow et al. 2011). The genus Myrtus includes flowering plant with
approximately 16 species reported in areas of the Middle East and Asia ( Twaij et al.,
1988 and Romani et al., 1999). M. communis L., known as true myrtle, is one of the
important aromatic and medicinal species from this family. It is an evergreen sclerophyll
shrub or small tree, 1.8–2.4 m in height, with small foliage and deep fissured bark (Mendes et
al. 2001). True Myrtle is characterized by its branches, which form a close full head, thickly
covered with ovate or lanceolate evergreen leaves (Fig. 1). Their leaves are 3–5 cm long and
contain tannins, flavonoids and volatile oils (Baytop 1999). This species is a very aromatic
plant because of the high essential oil content in its leaf, flower and fruit glands. It has
solitary axillary white or rosy flowers, followed by black a several-seeded berry which is
spherical in shape with dark red to violet in color (Mahmoud et al. 2010). There are two
major fruit morphologies based on the color – whether dark or white. The dark color is more
frequent, but there are also cultivated white-colored types, which yield much larger fruits
than their wild counterparts (Klein et al. 2000).
Fig. 1.
Myrtus communis L. plant (by courtesy of Prof. Michael Pascoe,
www.wordplants.ca).
Figure options
1.2. Distribution
Myrtle (M. communis L.) is a common part of typical Mediterranean flora. The plant grows
abundantly from the northwestern to the eastern Mediterranean, including bordering countries
and western Asia, as well as Aegean regions ( Baytop 1997). Myrtle is native to southern
Europe, North Africa and west Asia. It is also distributed in Southern America, northwestern
Himalaya and Australia. Myrtle is cultivated in gardens, especially in Northwest Indian
region, because of its fragrant flowers (Nadkarni 1989).
Being widespread throughout the Mediterranean region, the species is one of the most
important evergreen shrubs in the Mediterranean maquis. In Italy it grows along the coasts
and on the internal hills and it is abundant especially on the islands, where it represents one of
the most characteristic species (Cannas et al. 2013). In Portugal, myrtle grows wild mainly in
the central and southern parts of the country. The genus Myrtus, in Tunisia, is represented by
only one species, M. communis L., which grows wild in the coastal areas, the internal hills,
and the forest areas of northern Tunisia. Two myrtle varieties are described in old local
Tunisian flora: M. communis var. italica L. and M. communis var. baetica L. ( PottierAlapetite et al. 1979), which possesses the same vegetative characters. The morphological
difference between the two varieties regards to size of fruits and leaves. This herb grows
spontaneously Iran, Spain, France, Greece, Turkey, Algeria, Morocco, Croatia and
Montenegro ( Naserian, 1997, Chryssavgi et al., 2008, Mimica-Dukić et al., 2010, BerkaZougali et al., 2012, Mahmoud et al., 2010, Jerkovic et al., 2002 and Gauthier et al., 1988).
1.3. Traditional application
Myrtle has been used since ancient times as a spice, as well as for medicinal and food
preparation purposes.
Myrtle as a spice finds no wide application because of its bitterness, despite the pleasant
odor. The taste is very intense, quite unpleasant and strongly bitter, so its culinary application
is limited to the region of origin, such as Italy (Gortzi et al. 2008). In Italy, especially in
Sardinia, berries and leaves are used to produce two well-known liquors (Mirto Rosso and
Mirto Bianco, respectively) (Messaoud et al. 2012). Foods flavored with the smoke of myrtle
are common in rural areas of Italy or Sardinia (Gortzi et al. 2008). However, some parts of
the plant are used in the food industry, for flavoring meat and sauces (Chalchat et al. 1998),
and its berries and leaves are mostly employed for the industrial formulation of sweet liquors
with advertised digestive properties (Clark, 1996 and Mulas et al., 2000).
Its leaves are very fragrant and have been extensively used in the perfume and cosmetic
industries, particularly in Portugal (Clark 1996) as well as Turkey (Baytop 1999).
It is traditionally used as an antiseptic, disinfectant and hypoglycemic agent (Elfellah et al.
1984). In Turkey myrtle leaves as well as fruits have been used as an antiseptic medicine in
villages (Baytop 1999). Similarly, in Italian folk medicine, the fruit of this plant is used in the
treatment of many types of infectious disease, including diarrhea and dysentery; the leaves
are used as antiseptic and antiinflammatory agent, as well as a mouthwash, for the treatment
of candidiasis (Gortzi et al. 2008). The essential oil obtained from myrtle leaves has been
used in the treatment of lung disorders (Clark 1996). In traditional medicine, myrtle is
frequently consumed as an infusion and decoction (Le Floch 1983). Generally, in folk
medicine, a decoction of leaves and fruits is used orally for the treatment of stomach aches,
hypoglycaemia, disbiosis, cough, constipation, poor appetite, as well as also externally for
wound healing (Serce et al. 2010).
Different parts of the myrtle plant traditionally have assorted specific applications (Table 1).
Infusions made from the leaves and young branches are approved to be stimulant, antiseptic,
astringent and hypoglycemic, and they are considered to be a health remedy for asthma,
eczema, psoriasis, diarrhea, gastrointestinal disorders and urinary infections (Ziyyat et al.
1997). The leaf decoction is used for vaginal washing, enemas and against respiratory
diseases (Marchini and Maccioni 1998), while decoction from the fruits is used as
antidiarrheal, antihemorrhoidal agents and in mouth and eyes disease treatment (Ziyyat et al.
1997). Flowers are traditionally used against varicose veins, and for preparing capillary
lotions (Le Floch 1983).
Table 1.
Application of different M. communis L. parts.
M. communis L. part
Leaves
Traditional application
Food preparation – liquors,
flavoring meat and sauces;
Perfume and cosmetic
preparation – hair tonic and
stimulant; Medicine – orally
References
Messaoud et al.
(2012), Gortzi et al.
(2008), Chalchat et
al. (1998), Clark
(1996), Baytop
M. communis L. part
Traditional application
References
used as antiseptic, anti(1999), Elfellah et
inflammatory agent, laxative,
al. (1984), Serce et
analgesic, haemostatic agent and al. (2010)
externally for wound healing
Berries
Food preparation – liquors,
flavoring meat and sauces;
Medicine – used also orally for
infectious disease such as
diarrhea and dysentery and
externally for skin diseases and
wound healing
Brunches
Medicine – remedy for asthma,
eczema, psoriasis, diarrhea,
gastrointestinal disorders and
Ziyyat et al. (1997)
urinary infections, administrated
orally; applied by inhalation and
externally
Flowers
Medicine – against varicose
veins and for preparing capillary Le Floch (1983)
lotions for external use
Messaoud et al.
(2012), Clark
(1996), Serce et al.
(2010), Ziyyat et al.
(1997)
Table options
Other uses of its leaves include cattle feed, cut foliage and potted plants (Bruna et al. 2007).
2. Extraction procedures
Extraction techniques separate the soluble plant metabolites through selective use of solvents.
The process of obtaining plant extracts consists of several steps – collection and
authentication of plant material, drying, size reduction, extraction, filtration, concentration,
and final steps are further drying and reconstitution (Handa et al. 2008). It is important to
emphasize that the quality of an extract is influenced by several factors such as the plant parts
used as starting material, the solvent used for extraction, the extraction procedure, and the
solvent ratio. The solvents most commonly used for gaining extracts are water, methanol,
ethanol and ethylacetate (Chryssavgi et al., 2008, Amensour et al., 2010 and Tuberoso et al.,
2010).
Conventional methods used in extraction procedures from plants include soxhlet extraction,
thermal desorption, maceration, phytonic desorption, infusion, extraction leaching, surfactant
mediated extraction, accelerated solvent extraction, pressurized liquid extraction, steam
distillation, percolation, membrane process, decoction, sample disruption method, counter
current extraction and enfleurage (Handa et al. 2008).
According to European Pharmacopeia (2002) for essential oils preparation, it is needed air
dried plant materials such as leaves, flowers, fruit, berries and branches. The oils contained
within plant cells are liberated through heat and pressure from these parts of the plant matter,
and the color may vary from a pale to deep yellow depending of the plant part used. The
extraction of essential oils from plant material can be achieved by various methods, of which
the most commonly used methods include hydro-distillation (with a collecting solvent which
is then removed under vacuum), steam and steam/water distillation (Fig. 2) (Bowles, 2003,
Margaris et al., 1982 and Surburg and Panten, 2006). In addition to these conventional
methods, other newer methods for extracting essential oils use refrigerant hydrofluorocarbon
solvents at low temperatures, resulting in good quality of the extracted oils as well as solvent
extraction, effleurage, aqueous infusion, cold or hot pressing, supercritical fluid extraction,
solvent free microwave extraction (SFME) and phytonic process (Da Porto et al., 2009,
Hunter, 2009, Lahlou, 2004, Martínez, 2008, Ferhat et al., 2006, Pourmortazavi and
Hajimirsadeghi, 2007 and Surburg and Panten, 2006). Berka-Zougali et al. (2012) showed
that SFME is highly effective for reducing extraction time (30 min for SFME against 180 min
for hydro-distillation), providing an essential oil with a chemical composition enriched in
oxygenated compounds and has essential oils yields similar to those when hydro-distillation
method applied. Also, it had been found that hydro-distillation and steam-distillation methods
yield oils rich in terpene hydrocarbons, while in contrast, the super-critical extracted oils
contained a higher percentage of oxygenated compounds (Donelian et al., 2009, Eikani et al.,
2007, Reverchon, 1997 and Wenqiang et al., 2007). This implies that the quantitative and
qualitative chemical composition of the essential oil differs according to the applied
extraction technique. Thus, after the essential oil extraction, it is necessary to determine its
qualitative and quantitative characteristics. Quantities/yields of the essential oils are usually
determined gravimetrically, while qualitative analysis of the essential oils is usually
performed by gas chromatography (GC) or gas chromatography–mass spectrometry (GC–
MS) method (Mazza, 1983).
Fig. 2.
Essential oil extraction by steam distillation method.
Figure options
3. Chemical composition of Myrtus communis L. extracts
and essential oils
M. communis L. main secondary metabolites are polyphenols and essential oils. Myrtus
species have been reported as very rich in volatile oils ( Satrani et al., 2006, Shikhiev et al.,
1978 and Tuberoso et al., 2006), phenolic acids (Romani et al. 1999), flavonoids ( Romani et
al., 1999 and Joseph et al., 1987), tannins (Diaz and Abeger 1986), anthocyanin pigments
(Martin et al. 1990) and fatty acids (Cakir 2004). Previous studies on M. communis L. aerial
parts have also revealed the presence of several specific chemical compounds. For example,
the dried leaves of this herb contain 1,8-cineole (13.5–19.6%), linalool (7.7–15.8%), linalyl
acetate (2.5–6%), terpineole, terpinolene, tannins and flavonoid compounds ( Chryssavgi et
al. 2008). Leaf and flowers contain essential oils, phenolic acids, flavonoids and tannins (
Messaoud et al., 2005 and Aidi Wannes et al., 2010). Berries are composed of tannins,
anthocyanins (0.2–54%), fatty and organic acids (9–52%), and its content depends on used
extraction solvent and/or ripening period ( Martin et al., 1990, Tuberoso et al.,
2010 and Messaoud et al., 2012). It is evident that the content of these compounds also
differs depending on the plant part used ( Table 2 and Table 3), but generally the most
common compounds found in myrtle leaves, steams and flowers are α-pinene (∼10–60%)
and 1,8-cineole (∼12–34%) (Aidi Wannes et al. 2010).
Table 2.
Classes of major Myrtus communis L. essential oils compounds, their bioactivities and
content in different plant parts.
Sublaclass
es content
Major
Chemica Chemical in leaf,
myrtle
l classes subclasses steam and essential oil
flower compounds
(%)a
Major
compound
s content
Refernces
in myrtle
Bioactivity
for
leaf, steam
bioactivity
and flower
(%)
57–
60
9–
Monoterpe S 30–31 Limonene 11
ne
0.6
hydrocarbo
F 40–42.5 Myrcene
–
ns
0.8
C10H16
2.5
Terpenes
p-Cymene –
3.5
α0.2
Sesquiterpe L 0.4–0.6 Caryophylle –
ne
ne
0.3
hydrocarbo
Germacrene
ns
S 6.6–7.5
2.5
-D
C15H24
F 2–3.7
L 65–67.5 α-Pinene
Oxygenate
d
monoterpe
nes
Terpenoi
ds
Oxygenate
d
sesquiterpe
ne
Leaf
Flowe
r
Kalemba and
Antimicrob
Kunicka
Flowe ial
(2003)
r
Steam
Steam
Antiviral
Djilani and
Dicko (2012)
Antmicrobi
al (mostly
antibacteria
l)
Kalemba and
Kunicka
(2003),
Randrianariv
elo et al.
(2009)
Steam
Flowe
4.5
L 26
Linalool
r–7
steam
0.1
S 52–53 Myrtenol
– Steam
0.6
Flowe
Dec
F 33
1,8-Cineole
r-33
steam
0.1
Nerol
Steam
5
1.5 Flowe
Geraniol
–2 r
Caryophylle
L 0.1–0.8
1.5 Steam
ne oxide
Antimicrob Kalemba and
ial
Kunicka
Sublaclass
es content
Major
Chemica Chemical in leaf,
myrtle
l classes subclasses steam and essential oil
flower compounds
(%)a
Major
compound
s content
Refernces
in myrtle
Bioactivity
for
leaf, steam
bioactivity
and flower
(%)
S 0.1–0.2 Spathulenol
F 13.5–15
(2003)
0.6
Flowe
r
L 0.5–0.7
S 2–2.5
Methyleuge 4– Flowe
nol
4.5 r
F 3.5–4
Phenylpropanoi
ds
Korkina
Antioxidan
(2007), Pauli
t,
and
antimicrobi
Kubeczka
al
(2010)
a
L – leaf, S – steam, F – flower.
Table options
Table 3.
Classes of Myrtus communis L. extracts compounds, their bioactivities and content in
different plant parts.
Chemica
l classes
content
Chemical
in
classes
myrtle
extracts
(%)a
L 12–15
S 38–40
Phenolic
acids
Gallic acid
Cafeic acid
Leaf,
Syringic
steam,
acid
flower
Vanillic
, berry
acid
Ferulic acid
Antioxidant,
antimutagenic
, antitumor,
antibacterial
Othman et
al. (2007),
Shan et al.
(2007)
Antibacterial,
anti-cancer,
L 79–82
Hydrolysable
Gallotannin
Leaf,
antiviral,
S in
tannins
s
flower inhibition of
traces
lipid
F 60
peroxidation
B 53–56
Proanthocyanidi Delphinidi Leaf, Antioxidant
Funatogaw
a et al.
(2004),
Yokozawa
et al.
(1994)
Montoro et
F 38–40
B 8–10
Tannins
Chemical
subclasses
Major
myrtle Myrtl
Refernces
extracts
e
Bioactivity
for
compound organ
bioactivity
s
Chemica
l classes
content
Chemical
in
classes
myrtle
extracts
(%)a
Chemical
subclasses
ns
L 8–10
S 61–63 Flavonols
Flavonoide
F in
s
traces
B 35–39
Flavanols
Major
myrtle Myrtl
Refernces
extracts
e
Bioactivity
for
compound organ
bioactivity
s
n-3-Oflower
glucoside , berry
Petunidin3-Oglucoside
Malvidin3-Oglucoside
Cyanidin3-Oglucoside
Peonidin-3Oglucoside
Delphinidi
n-3-Oarabinoside
Petunidin3-Oarabinoside
Malvidin3-Oarabinoside
Myricetin
Myricetin3-Ogalactoside
Myricetin3-Oramnoside
Quercetin
Quercetin3-dgalactoside
Quercetin3-drahmnoside
Catechin
Leaf, Antibacterial,
steam, antiviral,
berry antioxidant,
antiinflammatory,
anti-allergic,
antithromboti
c,
Steam, vasodilatory,
Berry antimutagenic,
neoplastic,
anti-cancer
Leaf,
steam,
al.
(2006a),
Fine
(2000),
Okuda
(2005)
Harborne
and
Williams
(2000),
Montoro et
al. (2006a)
Chemica
l classes
content
Chemical
in
classes
myrtle
extracts
(%)a
Chemical
subclasses
Major
myrtle Myrtl
Refernces
extracts
e
Bioactivity
for
compound organ
bioactivity
s
berry
a
L – leaf, S – steam, F – flower, B – berry.
Table options
3.1. Myrtus communis L. essential oil compositions
Essential oils are odorous and volatile compounds found only in 10% of the plant kingdom
(Djilani and Dicko 2012). Essential oils and their components can be very promising
biological agents, because of their relative safety, wide acceptance by consumers and
exploitation for potential multi-purpose use (Ormancey et al., 2001 and Sawamura, 2000).
They are stored in plants in special brittle secretory structures, such as glands, secretory hairs,
secretory ducts, secretory cavities or resin ducts (Ahmadi et al., 2002, Bezic et al., 2009,
Ciccarelli et al., 2008, Gershenzon, 1994, Liolios et al., 2010, Morone-Fortunato et al., 2010,
Sangwan et al., 2001 and Wagner, 1996). The total essential oil content of plants is generally
very low and rarely exceeds 1% by mass (Bowles 2003). For example, the essential oil yields
in leaf, stem and flower of M. communis var. italica L. were respectively 0.61%, 0.08% and
0.30% (w/w) ( Aidi Wannes et al. 2010). Essential oils are hydrophobic and thus only slightly
soluble in water. They are soluble in alcohol, non polar or weakly polar solvents, waxes and
oils. Most essential oils are colorless or pale yellow, liquid and have lower density than water
( Gupta et al., 2010 and Martin et al., 2010). Essential oils are complex mixtures comprising
many various compounds. Chemically they are derived from terpenes and their oxygenated
compounds (Prabuseenivasan et al. 2006).
The chemical composition of the myrtle essential oil has been described by many authors
(Boelens and Jimenez, 1991, Boelens and Jimenez, 1992, Bradesi et al., 1997, Chalchat et al.,
1998, Ozek et al., 2000, Koukos et al., 2001, Aidi Wannes et al., 2007, Aidi Wannes et al.,
2009, Mimica-Dukić et al., 2010, Messaoud et al., 2012 and Kafkas et al., 2012). Compounds
that have been found in myrtle oils include E-2-hexenal, Z-3-hexenol, hexanol, tricyclene, αthujene, α-pinene, sabinene, β-pinene, myrcene, δ-3-carene, α-terpinene, p-cymene,
limonene, 1,8-cineole, E-β-ocimene, linalool E-oxide, terpinolene, linalool, terpinene-4-ol,
borneol, p-cymene-8-ol, α-terpineol, myrtenol, nerol, cis-carveol, geraniol, linalyl acetate,
bornyl acetate, eugenol, myrtenyl acetate, α-terpinyl acetate, geranyl acetate, neryl acetate,
methyl eugenol, β-caryophyllene, α-humulene, allo-aromadendrene, germacrene-D,
thiophene, geranyl 2-methylbutyrate, spathulenol, nonadecane, β-elemene, caryophyllene
oxide, camphene, α-phellandrene, γ-terpinene, cis-linalool oxide, trans-linalool oxide and
tridecane.
All these M. communis L. essential oil compounds may be classified into three main
categories: terpenes (monoterpene hydrocarbons and sesquiterpene hydrocarbons), terpenoids
(oxygenated monoterpenes and oxygenated sesquiterpenes) and phenylpropanoids ( Andrade
et al., 2011, De Sousa, 2011, Griffin et al., 1999, Lis-Balchin, 1997 and Sangwan et al.,
2001), but also into hydrocarbons and oxygenated compounds ( Akhila, 2006, Halm, 2008,
Hunter, 2009, Margaris et al., 1982, Pourmortazavi and Hajimirsadeghi, 2007 and Shibamoto
et al., 2010).
Terpenes form structurally and functionally different classes. Terpenes are hydrocarbons
produced from combination of several five carbon base units called isoprene units (C5H8).
They are synthesized in the cytoplasm of plant cells, and the synthesis proceeds via the
mevalonic acid pathway starting from acetyl-CoA. Terpenes have a hydrocarbon backbone
which can be rearranged into cyclic structures by cyclases, thus forming monocyclic or
bicyclic structures ( Caballero et al. 2003). The main terpenes are monoterpenes (C10H16) and
sesquiterpene (C15H24), but longer chains also exist. Examples of terpenes found in myrtle
essential oils include pinene, limonene, sabinene and myrcene. Terpenoids are terpenes that
undergo biochemical modifications via enzymes that add oxygen molecules and move or
remove methyl groups ( Caballero et al. 2003). Terpenoids can be sub-divided into alcohols,
esters, aldehydes, ketones, ethers, phenols and epoxides. Examples of myrtle terpenoids are
myrtenol, linalool, linalyl acetate and geraniol (Table 2). The main terpenes in myrtle
essential oils are the monoterpenes and sesquiterpenes and its terpenoids ( Aidi Wannes et al.,
2009, Aidi Wannes et al., 2010, Deriu et al., 2007 and Mimica-Dukić et al., 2010). The
monoterpenes formed from the coupling of two isoprene units are the most representative
molecules constituting 90% of the essential oils which allow a great variety of structures.
Various groups of organic compounds called phenylpropanoids are synthesized from the
aminoacid precursor phenylalanine in plants. Phenylpropanoids have their name from the sixcarbon aromatic phenol group and the three-carbon propene tail of cinnamic acid, produced
in the first step of phenylpropanoid biosynthesis. Phenylpropenes constitute a relatively small
part of myrtle essential oils, and those that have been most thoroughly studied are eugenol,
isoeugenol, vanillin, safrole and cinnamaldehyde (Hyldgaard et al. 2012).
Environmental factors were considered to play a key role in the chemical composition of
myrtle oil (Scora 1973). The fragrance and chemical composition of essential oils can vary
depending on the geo-climatic location and growing conditions, including concentration of
nutrients, temperature, humidity, soil type, day length, climate, altitude, amount of available
water, ect. The chemical composition also depends on season or vegetative period of plant,
i.e. before or after flowering ( Andrade et al., 2011, Deans et al., 1992, Margaris et al., 1982,
Pengelly, 2004 and Sangwan et al., 2001). According to these factors, plant biosynthetic
pathways can change the relative proportion of the primary oil components. These variations
in chemical composition led to the notion of chemotypes, which are generally defined as a
distinct population within the same species that produces different chemical profiles for a
particular class of secondary metabolites (Djilani and Dicko 2012). There are different
essential oil chemotypes which can distinguish myrtle oil of different origins, as well as
seasonal variations throughout the vegetative cycle of plants ( Bradesi et al., 1997, Chalchat
et al., 1998, Flamini et al., 2004 and Chryssavgi et al., 2008). Bradesi et al. (1997) proposed
classification of M. communis L. essential oil on the basis of myrtenyl acetate content, in two
chemotypes. Each chemoptype group can be further divided into two subgroups, according to
the relative ratio of α-pinene to myrtenyl acetate or α-pinene to cineole. In addition, plant
genotype is another important factor that influences the chemical composition of essential
oils ( Djilani and Dicko 2012). Therefore, all these biotope factors, genetic and epigenetic,
influence the biochemical synthesis of essential oils in a particular plant. Thus, the same
species of plant can produce a similar essential oil, but with different chemical composition
and therapeutic activities.
Essential oil composition also depends on the plant parts used for oil preparation. Chryssavgi
et al. (2008) determined that the Myrtus caommunis essential oil from leaves contain 42
compounds, while according to Aidi Wannes et al. (2010) there are 44 components
constituting Myrtus caommunis essential oil from leaves, stems and flowers. The same goup
of authors examined myrtle fruit essential oil composition during its ripening and identified
47 compounds whose concentration fluctuated during its different stages of ripening ( Aidi
Wannes et al. 2009). Although monoterpenes are dominant in essential oils (70–90%) the
distribution of oxygenated monoterpenes and monoterpene hydrocarbons vary. Aidi Wannes
et al. (2010) showed that monoterpene hydrocarbons dominate in leafs, followed by
oxygenated monoterpenes. In stems dominated oxygenated monoterpenes, followed by
monoterpenes hydrocarbons and sesquiterpene hydrocarbons. According to them, the flower
is characterized by high levels of monoterpene hydrocarbons and oxygenated monoterpenes
with an appreciable percentage of phenypropanoids. The major constituents of the leaf
essential oil composition are α-pinene, 1,8-cineole and β-pinene. The main essential oil
components in the flower are α-pinene and 1,8-cineole, as well as other compounds including
limonene, eugenol, α-terpineol, linalool and methyl eugenol. 1,8-Cineole is the dominant
component in stem essential oil and it is followed by α-pinene, E-β-ocimene and linalool
(Aidi Wannes et al. 2010). Analysis of myrtle fruit essential oil composition showed that the
main monoterpene compounds are 1, 8-cineole, geranyl acetate, linalool and α-pinene (Aidi
Wannes et al. 2009).
As shown, there is considerable variability in the composition of myrtle essential oil
depending on multiple biotope factors, but the most important constituents of myrtle oil are
terpenoids – myrtenol, myrtenol acetate, limonene, linalool, α-pinene, 1,8-cineole, αcaryophyllenein, as well as p-cymene, geraniol, nerol and the phenylpropanoid –
methyleugenol ( Ozek et al., 2000, Flamini et al., 2004, Deriu et al., 2007, Chryssavgi et al.,
2008, Aidi Wannes et al., 2009, Aidi Wannes et al., 2010, Mimica-Dukić et al.,
2010 and Messaoud et al., 2012) (Table 2).
3.2. Myrtus communis L. extracts composition
M. communis L. extracts profile constitutes polyphenolic compounds, which are grouped in
three major chemical classes – phenolic acids, tannins and flavonoids ( Table 3). Phenolic
acids, components of M. communis L. extracts are garlic, ellagic, caffeic, syringic, vanillic
and ferulic acid. Tannins as another essential oil component comprise hydrolysable tannins
(gallotannins) and proanthocianidins (condensed tannins). Flavonoids found in myrtle
extracts are myricetin, quercetin, catechin, and their derivates. Some of the myricetin and
quercetin derivatives (flavonols) found in myrtle extracts are myricetin-3-d-galactoside,
myricetin-3-d-rahmnoside, quercetin-3-rutinoside, quercetin-3-d-rahmnoside, and catechin
derivatives (flavanols) ( Aidi Wannes et al., 2010, Tuberoso et al., 2010, Montoro et al.,
2006b and Romani et al., 1999).
Extracts composition may significantly vary, depending on plant organ used for extraction
(Tuberoso et al., 2010, Aidi Wannes et al., 2010, Hayder et al., 2008, Montoro et al., 2006a,
Montoro et al., 2006b, Piras et al., 2009 and Romani et al., 2004). Amensour et al. (2009)
showed that leaf extracts contain significantly higher amount of total phenolic compounds
than berry extracts. Yoshimura et al. (2008) identified ten phenolic compounds from myrtle
leaf including four hydrolysable tannins (oenothein B, eugeniflorin D2, tellimagrandins I and
tellimagrandins II), two related polyphenolic compounds (gallic acid and quinic acid 3,5-diO-gallate), and four flavonols (myricetin 3-O-β-d-xyloside, myricetin 3-O-β-d galactoside,
myricetin 3-O-β-d-galactoside 6-O-gallate and myricetin 3-O-α-l-rhamnoside).
The contents of total phenols, tannins, flavonoids and proanthocyanidins vary among myrtle
parts. According to Aidi Wannes et al. (2010), leaf and flower are particularly rich in total
tannins. Since the proanthocyanidins are weakly presented, the authors suggested that leaf
and flower tannins belong to hydrolyzed tannin class. However, they estimated that the
myrtle stem is poor in tannins and moderately rich in flavonoids (catechin). Flavonols and
flavanols in M. communis L. leaves are detected in relatively large amounts ( Aidi Wannes et
al. 2010), with the exception of quercetin derivatives and phenolic acids, which were found
only in small amounts ( Romani et al., 1999 and Romani et al., 2004).
Except myrtle plant parts, finale extract composition depends also on extraction solvent used
for extract preparation, mainly because of its polarity (Lapornik et al., 2005). The most
commonly used solvents for myrtle extract preparation are water, alcohol (methanol or
ethanol), ethyl acetate, diethyl ether and chloroform. Tuberoso et al. (2010) proved that
ethanol and water extracts showed higher amount of extracted compounds in comparison to
ethyl acetate extracts, but the highest antiradical and antioxidant activities were found in
ethanol and ethyl acetate extracts. According to them ethanol extracts has the highest content
of phenolic compounds. In addition, their results showed a highly significant correlation
between the amount of total phenols and antiradical or antioxidant activities in myrtle leaf
extracts.
According to this it is important to compare and explore the variance of phenol composition
from various myrtle extracts, since this heterogeneous repartition of bioactive substances
entrained the variability of their potential antimicrobial and antioxidant activities.
3.3. Activity of Myrtus communis L. compounds
Antimicrobial (antibacterial, antifungal and antiviral) and antioxidant properties of
compounds produced by M. communis L. have been reported in numerous studies ( Pereira et
al., 2012, Othman et al., 2007, Shan et al., 2007, Funatogawa et al., 2004, Naserian,
1997 and Rattanachaikunsopon and Phumkhachorn, 2010). For example, 1,8-cineole,
linalool, eugenol, α-terpineol and γ-terpinene, as myrtle essential oils components have a
good bactericidal effect against some Gram positive and Gram negative bacteria ( Oyedemi et
al., 2009 and Randrianarivelo et al., 2009). According to Randrianarivelo et al. (2009) results,
linalool MICs and MBCs values ranging 0.18–5.88 mg/ml and 0.18–11.75 mg/ml,
respectively; while this values for 1,8-cineole ranged from 0.37 to 11.75 mg/ml and 0.73 to
11.75 mg/ml, respectively. Also, Zanetti et al. (2010) showed that some myrtle single
compounds such as limonene (0.17–2%), 1,8-cineole (2–16%) and α-pinene (1–16%) have
significant activity against M. tuberculosis strains. These biological effects of myrtle essential
oils and extracts are result of activity of compounds belonging to various chemical classes.
For example, in the mid-1970s, scientists reported the isolation of a phloroglucinol antibiotic
from the myrtle leaves, named as myrtucommulone A, and along with it they isolated more
polar and abundant phloroglucinol 6, named semimyrtucommulone ( Appendino et al. 2002).
It is proved that these myrtle compounds possess significant activity against S. aureus strains,
with MICs values in range 0.5–2 μg/ml for myrtucommulone A, and 32–64 μg/ml for
semimyrtucommulone (Appendino et al. 2002). This low MICs concentrations are the
consequence of pure compounds application, which in mixture with other compounds
influence on enhancing of essential oils antimicrobial activity.
The complexity of extracts or essential oils chemical composition suggests involvement of
various action mechanisms and consequently, it is difficult to identify just one pathway of
molecular action. It is very likely that each of the constituents of the essential oils/extracts has
its own mechanism of action (Djilani and Dicko 2012) or in the other hand, the compounds
could act on synergistic way. For instance, various synergistic antimicrobial activities have
been reported for constituents or fractions of essential oils when tested in binary or ternary
combinations (Delaquis et al., 2002, Pei et al., 2009, García-García et al., 2011 and Nguefack
et al., 2012).
4. Antimicrobial assays for plant extracts and essential oils
Two methods for determining the antimicrobial properties of extracts and essential oils that
are the most widely used are agar diffusion method and broth dilution method. The water
insolubility, complexity and volatility, of extracts and especially essential oils are among
their primary characteristics and these properties influence the assessments of antimicrobial
activities. The agar diffusion method is not considered an ideal method for essential oils, as
their volatile components are likely to evaporate with the dispersing solvent during the
incubation time, while their poorly soluble components do not diffuse well in the agarised
media. This problem can overcome by using Tween 80 and DMSO (dimethyl sulfoxide) to
enhance the solubility of oils. Since the method is relatively simple, it still remains the most
commonly used technique (Prabuseenivasan et al., 2006 and Davidson and Parish, 1989).
The inhibitory effect of plant extracts and essential oils in the test tubes and microtitar plates
is measured turbidimetrically or with the count plate method. The results are usually
presented as values of minimal inhibitor concentration (MIC) and minimal bactericidal
concentration (MBC) (CLSI 2006). In experiments testing the extracts and essential oils
activity toward microorganisms, results depends mainly on the method used, however a
number of other factors should also be considered. Culture conditions and initial namber of
bacterial cells predominantly influence the analysis; therefore they should be precisely stated
in reports (Kalemba and Kunicka 2003).
5. Biological effects of Myrtus communis L.
5.1. Antibacterial effect
The problems regarding application of conventional antibiotics, including antimicrobial
resistance, environmental problems, cancerogenity, side effects and high costs, have
reinforced a tendency to replace synthetic antimicrobials with natural alternative agents
(Gortzi et al. 2006). Plant based products are among the alternative agents examined in order
to replace conventional antibiotics (Harikrishnan et al., 2003, Immanuel et al., 2004, ShahidiBonjar, 2004a and Shahidi-Bonjar, 2004b). Accordingly, extensive research has been carried
out in order to evaluate the antimicrobial effect of the essential oils and extracts which
showed the ability to inhibit the growth of various pathogenic microorganisms (AyatollahiMoosavi et al. 1996) (Table 4).
Table 4.
Myrtus communis L. antimicrobial activity.
Myrtus communis L.
Crude preparation of
myrtle (mg/ml)
Crude extracts (mg/ml)
Microorganism
S. aureus
P. mirabilis, P. vulgaris
K. aerogenes, Salmonella
Typhi
P. aeruginosa
Shigiella shigie
E. coli
S. aureus, M. luteus
Activity
MBC
0.5
2.5
15
References
Alem et al.
(2008)
20
40
45
MIC
0.1
Mansouri et
al. (2001)
MIC
Myrtle leaves essential
oil (%, v/v)
Aqueous extracts of
leaves
S. aureus, L.
monocytogenes, E. durans,
0.5
Salmonella Typhi, E. coli,
B. subtilis
P. aeruginosa
>1
P. aeruginosa
Myrtle plant essential oil P. aeruginosa
(μg/ml)
Myrtle leaves essential
oil (%, v/v)
M. tuberculosis
M. avium subsp.
paratuberculosis
B. subtilis DCM 3366
E. faecium CECT 410
L. innocua CECT 4030
L. monocytogenes CECT
Methanolic, ethanolic
4032, P. aeruginosa IH, S.
and ethylacetate extracts
aureus MBLA, S. aureus
of myrtle leaves and
CECT 976
berries
S. aureus CECT 794
P. vulgaris CECT 484
P. aeruginosa CECT 110T,
P. flourescens CECT 378
Escherchia coli K12
Akin et al.
(2010)
Effects located
within the limits Al-Saimary et
of antibiotic
al. (2002)
effects
MIC MBC
64 64
MIC
0.17%
>2%
Owlia et al.
(2009)
Zanetti et al.
(2010)
MIC
0.3
2.5
0.15
0.625
<0.075
>5
5
–
Amensour et
al. (2010)
Myrtus communis L.
Microorganism
S. aureus, S. mutans, S.
viridans
Methanol extracts (6 μl S. epidermidis
of 1 mg/ml of the leaves P. aeruginosa, E. cloacae,
extracts have been put on K. pneumoniae, E. coli, C.
the discs)
tropicalis, C. glabrata
C. albicans, L.
monocytogenes
Hydroalcoholic leaf
extract of Myrtus
communis (mg/ml)
Myrtle leaves essential
oil (μl/ml)
Activity
References
14 mm
13 mm
12 mm
Gortzi et al.
(2008)
10 mm
S. aureus
P. aeruginosa
E. coli
V. cholerae
MIC MBC
0.2 2
–
8 40
2 20
Taheri et al.
(2013)
C. albicans, C. tropicalis
C. glabrata, C. krusei
C. parapsilosis
MIC
2
4
2–4
Cannas et al.
(2013)
MIC MBC
E. coli ATCC 25922, S.
Myrtus communis L.
Typhi, E. coli, K.
infusions (mg of dry
pneumoniae
leaves per ml of infusion)
P. mirabilis
S. flexneri
25 50
Messaoud et
al. (2012)
12.5 25
12.5 12.5
Myrtle plant essential oil
E. coli, S. aureus
(μl/ml)
C. albicans
MIC MBC
48
24
Yadegarinia
et al. (2006)
Myrtle leaves essential
oil; used for vegetable
washing (ppm)
500–1000
Gündüz et al.
(2009)
S. Typhimurium ATCC
13311
B. subtilis (ATCC 6633)
S. Enterica, E. cloacea, P.
aeruginosa, K. pneumonia,
S. aureus (CIP 7625)
Leaf essential oils; MIC L. monocytogenes (CIP
(μl/ml)
82110)
C. albicans
A. flavus
E. coli, A. ochraceus, F.
culmorum
Essential oil from plant
H. pylori strains
HD SFME
20 10
30 20
30 30
BerkaZougali et al.
(2012)
50 50
50 20
30 10
MIC
Deriu et al.
Myrtus communis L.
in flowering period (%,
v/v)
Essential oil (mg/ml)
Microorganism
Activity
0.01–2.5
B. subtilis
MIC
1.4–11.20
References
(2007)
Rosato et al.
(2007)
HD – hydrodistillation, SFME – solvent-free-microwave-extraction.
Table options
The antibacterial properties of myrtle essential oils and extracts against pathogenic bacteria
were reported in many studies and obtained results are promising (Table 4).
Taheri et al. (2013) indicated antibacterial effect of myrtle leaves hydroalcoholic extract on
some pathogenic bacteria, particularly Staphylococcus aureus and Vibrio chloreae. Mansouri
et al. (2001) also proved antibacterial activity of several myrtle extracts and essential oils and
estimated that they have different activities because of its different constituting compounds.
Crude extracts of myrthle was tested against 6 Gram positive (S. aureus, Micrococcus luteus,
Streptococcus pneumoniae, Streptococcus pyogenes, Streptococcus agalactiae, Listeria
monocytogenes) and 4 Gram negative bacteria (Escherichia coli, Proteus vulgaris,
Pseudomonas aeruginosa and Campylobacter jejuni), and inhibited the growth of all tested
bacteria except C. jejuni. MICs range from 0.1 for S. aureus and M. luteus to over 2 mg/ml
for E. coli. The group of authors made diethyl ether, ethyl acetate, and ethanol extracts. The
diethyl ether extracted fraction showed the highest level of activity with a MIC 0.025 mg/ml
for S. aureus and M. luteus and 0.1 mg/ml for E. coli and P. aeruginosa. Alem et al. (2008)
observed similarity between MIC and MBC for myrtle crude preparation, which vary from
0.5 ml/l for S. aureus to 45 mg/ml for E.coli. It is also interesting to mention that the
antibacterial activity of myrtle was markedly increased by 18 times after it has been
autoclaved at 121 °C for 15 min.
When tested against 150 strains isolated from burns (predominantely P. aeruginosa i S.
aureus), aqueous leaves extracts of M. communis gave an excellent effect on bacterial growth
and their effects were located within the limits of antibiotic effects ( Al-Saimary et al. 2002).
High antibacterial activity of methanol, ethanol, and ethyl acetate leaf and berry mythle
extrcats was observed when it tested aginst foodborne pathogens. The methanolic leaf extract
of M. communis showed antibacterial activity even against L. monocytogenes and P.
aeruginosa, but none of the extracts was active against E. coli K12 ( Amensour et al. 2010).
The activity of methanolic extract was also confirmed in other studies, such as Gortzi et al.
(2008). Hydroalcocholic extracts of myrthle leaves inhibited S. aureus with a low MIC
(0.2 mg/ml); it was less effective against E. coli and V. cholerae (8 and 2 mg/ml,
respectively) and ineffective against P. aeruginosa ( Taheri et al. 2013). In this study,
detected MBC was 5–10 times greater than MIC.
M. communis infusion, prepared from dry leaves, showed lower activity against examined
Gram negative bacteria, with MIC varied from 12.5 to 50 mg/ml (Messaoud et al. 2012).
M. communis L. extracts profile constitutes polyphenolic compounds – phenolic acids,
tannins and flavonoids, whose antimicrobial activity varies. Some results have indicated that
phenolic compounds significantly contributed to the antibacterial activity ( Shan et al. 2007).
This activity may be attributed to the enzyme inhibition by the more oxidized phenolic
compounds possibly through reaction with sulfhydryl compounds or through more nonspecific interactions with the protein (Schelz et al. 2010). Cinnamic acid and caffeic acid
were shown to be toxic to microorganisms (Cowan 1999). Tannins as polymeric watersoluble phenols are commonly present in higher herbaceous and woody plants. Tannins are
reported to possess free radical scavenging activity and also have antibacterial effects
(Akiyama et al. 2001). Hydrolysable tannins have antibacterial potential against Helicobacter
pylori and it seems promising in the eradication of the bacterium without affecting intestinal
microbiota ( Funatogawa et al. 2004). A great deal of flavonoids is synthesized by plants to
fight against bacterial infections, therefore it is no surprise that they exhibit in vitro
antimicrobial activity ( Tsuchiya et al., 1996 and Cushine and Lamb, 2005) and the similar
refers to catechins (Gradisar et al. 2007).
Antibacterial activity of essential oils has been demonstrated in many studies. In the study of
Akin et al. (2010) the oils showed considerable activity against most Gram negative and
positive bacteria at concentration of 0.5% (v/v). It is interesting to notice that oils were also
effective in concentrations 0.01–2.5% against Helicobacter pylori, which is a main cause of
duodenal ulcer ( Deriu et al. 2007), while the extracts of Malpighia emarginata fruit were
effective against H. pylori with MICs values between 17 and 27 μl/ml (Motohashi et al.
2004). They also showed activity against foodborne pathogen Salmonella Typhimurium
when vegetables were whased with oils concentration of 500–1000 ppm (Gündüz et al.
2009). Against well known resistant bacteria M. tuberculosis myrtle essential oils showed
activity in concentration 0.17%, but not against M. avium subsp. paratuberculosis (>2%) (
Zanetti et al. 2010). Similarily, low level of activity has been observed against P. aeruginosa,
which is well known bacterium notoriously resistant to antibiotics ( Owlia et al. 2009).
Randrianarivelo et al. (2009) showed that major myrtle oil compounds – oxygenated
terpenes, such as 1,8-cineole, linalool and α-terpineol, exhibit potent antibacterial activity.
The antimicrobial activity of most terpenoids is linked to their functional groups and it has
been shown that the hydroxyl group of phenolic terpenoids and the presence of delocalized
electrons are important for antimicrobial activity. For example, the antimicrobial activity of
the carvacrol derivatives (carvacrol methyl ether and p-cymene) were much lower than
carvacrol (Dorman and Deans, 2000, Ultee et al., 2002 and Ben Arfa et al., 2006).
Furthermore, it has been shown that phenylpropanoids antimicrobial activity depends on the
type and number of substituents on the aromatic ring, tested microbial strains, and various
experimental test parameters, including growth medium, temperature, etc. ( Pauli and
Kubeczka 2010).
In vitro tests indicated that terpenes are inefficient as antimicrobials when applied as single
compounds ( Dorman and Deans, 2000, Koutsoudaki et al., 2005 and Rao et al., 2010), while
certain terpenoid components of essential oils can act as uncouplers, interfering with proton
translocation over a membrane vesicle and subsequently interrupting ADP phosphorylation
(Schelz et al. 2010). Terpenoids may serve as an example of lipid soluble agents which affect
the activities of membrane-catalyzed enzymes exhibiting action on respiratory pathways.
Specific terpenoids with functional groups, e.g. phenolic alcohols or aldehydes, also interfere
with membrane-integrated or associated enzymes and/or proteins, stopping their production
or activity ( Kalemba and Kunicka 2003).
It is interesting to mention that there is a report on application of liposomes and M. communis
extracts, with aim to overcome the problem of bacterial resistance ( Gortzi et al. 2008). Due
to their unique properties, liposomes are able to enhance the effects of products by increasing
ingredient-solubility (easier incorporation of water-soluble compounds into oil-based
products), improving the bioavailability and the in vivo and in vitro stability ( Gortzi et al.
2006). The extract from the herbal parts of M. communis L. possessed antimicrobial activity,
which dramatically increased after the encapsulation in liposomes. These findings indicate
that encapsulated myrtle extracts can be used as potent preservative, not only in food industry
but also in cosmetics and pharmacology.
In order to control the growth of multi-drug resistant bacteria, essential oils could also be
combined with other antimicrobial agents, such as bacteriophages. Synergistic effect of these
two agents represents a potential solution to replace antibiotics. Indeed, it has been shown
that damage of bacterial cell membrane caused by essential oils, either facilitates penetration
of bacteriophages with subsequent replication inside the bacterial cell, or is supported by
simultaneous action of bacteriophages and essential oils on the cell membranes
(Volodymyrivna Kon and ans Kumar Rai 2012).
5.1.1. Mode of antibacterial action
Different modes of action are involved in the antimicrobial activity of essential oils and
extracts. Because of the variability of quantity and chemical profiles of the essential oil and
extract components, it is likely that their antimicrobial activity is not due to a single
mechanism. It is considered that these components have several sites of action at the cellular
level. Generally, there are six possible mechanisms of antimicrobial action, which include:
(1) disintegration of cytoplasmic membrane, (2) interaction with membrane proteins
(ATPases and others), (3) disturbance of the outer membrane of gram negative bacteria with
the release of lipopolysaccharides, (4) destabilization of the proton motive force with leakage
of ions, (5) coagulation of the cell content, and (6) inhibition of enzyme synthesis (Amensour
et al., 2010, Cox et al., 2001, Bakkali et al., 2008, Burt, 2004, Di Pasqua et al.,
2007 and Hammer et al., 2008).
The mode of myrtle extract and essential oil activity affect mainly cell wall and membrane
structures. It was reported that the permeability of bacterial cell wall and cell membrane are
affected by these extracts, leading to the release of intracellular contents outside of cell. This
can be accompanied with the disruption in the membrane function such as electron transfer,
enzyme activity or nutrient absorption (Amensour et al. 2010).
Oyedemi et al. (2009) showed that essential oils components (eugenol, α-terpineol and γterpinene) have a bactericidal effect against the both Gram positive and Gram negative
bacteria by disrupting their membrane systems. Its important characteristic – their
hydrophobicity, enables them partition the lipids of bacterial cell membrane, disturbing the
cell structure and rendering them more permeable. It has been generally reported that the
Gram negative bacteria are more resistant to the myrtle extracts and essential oils than Gram
positive (Amensour et al., 2010, Taheri et al., 2013 and Kokoska et al., 2002). This resistance
is likely due to the fact that Gram negative bacteria have a wall associated with an outer
complex membrane, which slows down the passage of essential oils hydrophobic compounds
(Inouye et al. 2001). Lacking outer membrane, Gram positive bacteria are more susceptible to
the myrtle extracts and essential oils according to this model.
Flavonoids are considered to possess ability to form complexes with extracellular soluble
proteins and with bacterial cell wall (Tsuchiya et al., 1996 and Cushine and Lamb, 2005).
Catechins, beside their versatile activities, exert antibacterial effects via DNA gyrase
inhibition. Indeed, specific binding of selected catechins was demonstrated for the N-terminal
fragment of gyrase B ( Gradisar et al. 2007). Furthermore, catechins are able to restore the
susceptibility of bacterial antibiotic resistance to antibiotics such as tetracycline, beta-lactams
and beta-lactamase inhibitors ( Roccaro et al., 2004, Stapleton et al., 2004 and Zhao et al.,
2003).
5.2. Antifungal effect
The management of fungal infections possesses many problems, including a limited number
of antifungal drugs, toxicity, resistance to commonly used antifungal drugs, relapse of
infections and the high costs (Khan et al., 2003 and Khan et al., 2010). It is therefore
necessary to discover new antifungal agents to combat the strains expressing resistance to the
available antifungal drugs. One of natural products used as therapeutic agent against fungi is
myrtle, e.g. its essential oils and extracts ( Table 4).
Considerable myrtle extract activity was estimated by Gortzi et al. (2008), while antifungal
activity of myrtle essential oil was tested against different Candida species, and minimal
inhibitory concentrations were in range 2–4 μl/ml (Cannas et al. 2013). The myrtle antifungal
effect may also be attributed to essential oil and phenolic compounds that are known to cause
cell membranes damage, causing leakage of cellular materials and ultimately the
microorganism death (Cox et al. 2001). The antimicrobial, e.g. antifungal property of myrtle
is suspected to be associated with their high contents of polyphenols and oxygenated
monoterpens.
Modes of antifungal actions are quite similar to those described for bacteria, concerning
irreversible damage of the cell membrane and coagulation of the cell content. Except these
two, there are additional phenomena which are also important when yeasts are considered.
The first one is the establishment of a pH gradient across the cytoplasmic membrane, and the
second one is blocking of yeasts energy production which result in disruption of the cell
membrane (Djilani and Dicko 2012).
5.3. Antiviral effect
The antiviral activity of the essential oil is principally due to direct virucidal effects, by
denaturing viral structural proteins or glycoproteins (Djilani and Dicko 2012). Essential oil
activity against viruses can be dual. Proposed mechanisms suggest that essential oils eider (1)
interfere with the virus envelope by inhibiting specific processes in the viral replication cycle
or (2) mask viral components, which are necessary for adsorption or entry into host cells and
cell-to-cell virus diffusion (Saddi et al. 2007).
Due to synergistic phenomena, the complex mixture of essential oils usually shows a higher
antiviral activity than individual compounds (Djilani and Dicko 2012). Several
phytochemicals have complementary and overlapping antiviral effects, which comprise
inhibition of viral nucleic acid synthesis or inhibition of other stages in viral multiplication
(Jassim and Naji 2003). The best known antiviral compound produced by many plants
belonging to various families, including M. communis L. plant, is α-caryophyllene ( Djilani
and Dicko 2012). It is considered that further characterization of the active ingredients will
reveal more useful antiviral compounds.
5.4. Antioxidant effect
Antioxidants are compounds that react with free radicals, neutralizing them and thereby
preventing or reducing their damaging effects in the human body (Pereira et al. 2012). Lipid
oxidation is also responsible for deterioration of fats and oils resulting in change of color,
flavor and nutritive value, while oxidative stress is involved in the pathogenesis of numerous
diseases (Young and Woodside 2001). In order to prevent oxidation, the addition of either
synthetic or natural antioxidants to fats, fatty foods and cosmetics is a common practice.
Because of its carcinogenicity, synthetic antioxidants used in products for human application
are being restricted, considerably increasing interest in antioxidants of natural origin (Namiki,
1990, Gazzani et al., 1998, Sasaki et al., 2002, Djeridane et al., 2006 and Halliwell and
Whiteman, 2004).
Aromatic and medicinal plants, such as myrtle, are a source of natural antioxidants because of
the activity of secondary metabolites, such as phenylpropanoids and essential oils. These
plant essential oils and extracts have been used for many thousands of years in food
preservation, pharmaceuticals, alternative medicine and natural therapies (Reynolds, 1996,
Lis-Balchin, 1997, Lis-Balchin and Deans, 1997 and Burt, 2004). As demonstrated in several
studies, the antioxidant capacity of plant extracts is strongly related to phenolic content
(Wang et al., 1999, Wang and Stretch, 2001 and Zheng and Wang, 2003). This activity is not
a property of a single phenolic compound, but it is widely distributed among the phenolic
phytochemical constituents. Particularly anthocyans, flavonoids and phenolic acids seem to
be responsible for the antioxidant capacity (Table 2). The antioxidant activity of the phenolic
compounds were attributed to its redox properties, which allow them to act as reducing
agents, hydrogen donators, singlet oxygen quenchers and metal chelators (Rice-Evans et al.
1995). Many in vitro studies indicate that phenolic compounds like flavonoids and phenolic
acid, can have considerable antioxidant activity and this activity critically depends on the
number and position of phenolic hydroxyls in the aromatic ring moieties ( Duthie and Crosier
2000). Generally, monophenols are less effective than catecholic phenols, and phenolic
aglicons have higher antioxidant activity than their respective glycosides (Duthie and Crosier
2000).
Several reports describe the antioxidant activities of different extracts and compounds
obtained from myrtle leaves (Chryssavgi et al., 2008, Hayder et al., 2008, Romani et al.,
2004 and Rosa et al., 2008). However, leaves are not suitable for human consumption,
because of their excessive bitterness and high level of terpenic compounds. Berries on the
other hand are used to make liqueurs, jam and other food products. Ethanol extracts obtained
from berries were studied according to their antioxidant properties (Alamanni and Cossu,
2004 and Vacca et al., 2003). Tuberoso et al. (2007) found in myrtle berries very high
correlation between antiradical or antioxidant capacity and total phenol amount, but they did
not investigate relative contribution of each phenolic compound in the antioxidant capacity.
On the contrary, the anthocyanine fraction does not appear to be associated to the antioxidant
capacity of myrtle berries (Angioni et al. 2011). The use of assays that analyze these
antioxidant activities evaluating the different chemical or biological targets involved, is key
to elucidate mechanism involved in such activities. The antioxidant properties and
composition of the ethanol extracts obtained from myrtle berries have been studied as well
(Alamanni and Cossu, 2004, Montoro et al., 2006b and Vacca et al., 2003) and mainly
focused on their main compounds – anthocyanins and flavonols, which are generally
considered to be responsible for antioxidant activity (Alamanni and Cossu, 2004, Romani et
al., 2004, Franco et al., 2002, Montoro et al., 2006a, Montoro et al., 2006b and Tuberoso et
al., 2010).
Various known antioxidants like flavonoids, tannins (Romani et al. 2004) and α-tocopherol
have been isolated from myrtle extracts. M. communis L. also exhibit the biological activities
of tannins including anticancer and antioxidant activities ( Romani et al. 2004). Nowadays,
the interest in naturally occurring antioxidants has considerably increased, because of their
potential application in food, cosmetic and pharmaceutical products, in order to replace
synthetic carcinogenous, and thus restricted antioxidants ( Sasaki et al., 2002 and Djeridane et
al., 2006). In addition, oligomeric proanthocyanidines, which are mainly used in vascular
diseases, have ability to trap lipid peroxides and free radicals, as well as non-competitively
inhibit xanthine oxidase, which is a major generator of free radicals ( Fine, 2000 and Okuda,
2005).
5.5. Other biological effects
In addition to the biological activities of M. communis that are mentioned above, there are
also other numerous important biological activities which can be sub-classified as
biochemical i.e. pharmacological effects, including anti-inflammatory, anti-diabetic, antimutagenic, pro-apoptotic activity in cancer cells, cardiovascular, anti-atherogenicity, activity
against hepatic ischemia, as well as insecticidal, molluscicidal and protozoicidal effects. They
are listed in Table 5, with indicared references confirming specific activity of myrtle oil,
extracts or compounds. The term pharmacological activity refers on biochemical interactions
of myrtle extracts, oils or its compounds in the bloodstream, such as interactions with
different hormones and enzymes. Pharmacological activities usually are investigated in vivo
on different model organisms considering the bioavailability of essential oils. The
bioavailability represents one of the principal pharmacokinetic and pharmacodynamics
properties of drugs, and it is used to describe the fraction of unchanged drug administered
dose that reaches the systemic circulation and can be used for a specific function and/or
stored ( Djilani and Dicko 2012). It is important to notice that administered dose can be toxic
to human cells. Dell’Agli et al. (2012) demonstrated that the three different essential oils of
M. communis, Satureja thymbra and Thymus herba-barona are toxic to human cells at
concentrations of 100 μg/ml. However, this is far higher concentration than those required for
the larvicidal or mosquitocidal effects (0.15 and 8 μg/ml, respectively). Also, extracts of M.
communis L. were found to be the most efficient against mosquito Culex pipiens with LC50
value of 16 mg/l, followed by those of Origanum syriacum L., Mentha microcorphylla Koch.,
Pistacia lentiscus L. and Lavandula stoechas L. (LC50 values were 36, 39, 70 and 89 mg/l,
respectively) (Traboulsi et al. 2002). While extract of M. communis L. caused death of T.
vaginalis at pH 4.65, but failed to do so at pH 6.00; more efficient was Eucalyptus
comaldensis extract (50 mg in 0.1 ml medium) which at pH 5.35 caused death of T. vaginalis
after 24 h (Mahdi et al. 2006). Myrtle oil exhibit antimicrobial effects at relatively low
concentrations, so its potential medical application is more possible in comparison to
essential oils obtained from some other plants (Table 4). For instance, although peppermint
oil and its components showed antimicrobial effects, its MICs values in some cases reached
concentration of 5 mg/ml (Iscan et al. 2002), being a limitation for the medicinal use of the
peppermint oil.
Table 5.
Myrtus communis L. pharmacological activities.
Pharmacological
effect
Model organism
Rats
Mice
Anti-inflammatory
Mice
Diabetic mice
Diabetic rats
Anti-diabetic
Alloxan-diabetic
rabbits
Alloxan induced
diabetic rabbits
Anti-mutagenic
Dosage and application mode
of myrtle extract, oil or
Reference
compound
1/10 of the intraperitoneal
Al-Hindawi
LD50 doses for the 80%
et al. (1989)
ethanol extracts
0.5, 1.5, 4.5 mg/kg
Myrtucommulone
Rossi et al.
administered to mice
(2009)
intraperitoneally
IC50 values in the range of 1.8
to 29 μM for myrtucommulone
Feisst et al.
and semimyrtucommulone
(2005)
present in the leaves of M.
communis
Ethanol-water extract of M.
communis (2 g/kg)
administered intragastrically
800 mg/kg body weight of
phenolic compounds, extracted
from the leaves of M.
communis injected
intraperitoneally
50 mg/kg volatile oil (Myrtii
Oleum) obtained from the
leavesapplied orally
Myrtle oil applied orally
Essential oil expressed high
reduction of mutagenesis in a
Escherichia coli
concentration dependent
oxyR mutant IC202
manner (0.05, 0.075, 0.1,
0.15 μl/plate)
Inhibitory activity
Myricetin-3-o-galactoside and
against nifuroxazide,
myricetin-3-o-rhamnoside,
aflatoxine B1 and
isolated from leaves of M.
H2O2 induced
communis
mutagenicity
Elfellah et
al. (1984)
Fahim et al.
(2009)
Sepici et al.
(2004)
Dineel et al.
(2007)
MimicaDukić et al.
(2010)
Hayder et al.
(2008)
Pro-apoptotic
activity in cancer
cells
Induce cell death of
different cancer cell EC50 3–8 microM of
Tretiakova
lines with
myrtucommulone from Myrtus
et al. (2008)
characteristics of
communis
apoptosis
Cardiovascular
Guinea pig and
The aqueous extract of leaves Al-Zohyri et
anaesthetized rabbit with concentration dependent al. (1985)
Pharmacological
effect
Model organism
Dosage and application mode
of myrtle extract, oil or
Reference
compound
depressive effect of the total
extract
Protective effect on
cholesterol and
human low density
lipoprotein (LDL)
2.5–60 nmol and 5–50 μmol of
semimyrtucommulone and
Rosa et al.
myrtucommulone A extracted (2008)
from M. communis
Hepatic ischemiareperfusion rats
Myrtle extracts of black fruit
11.32 μg/ml and white fruit
26.85 μg/ml and the leaves of Salouage et
black fruit myrtle 94.25 μg/ml, al. (2009)
injected 15 min before
reperfusion
Anti-ulcer
Wistar rats
Two doses of aqueous extracts
(105 and 175 mg/kg) and
methanolic extracts (93 and
Sumbul et
154 mg/kg) of dried berries of al. (2010)
myrtle were administered
orally
Insecticidal
Plasmodium
falciparum
Antiatherogenicity
Activity against
hepatic ischemia
Myrtle essential oil 150–
270 μg/ml
The larvicidal and
Mosquito and larvae mosquitocidal myrle oil effects
Anopheles gambiae was 0.15 and 8 μg/ml,
respectively
Activity is due to the presence
Pediculus humanis
of lineol and α-pinene and
capitis
linalool in myrtle oil
Larvae of mosquito LC50 for essential oil extracts
Culex pipiens
from leaves and flowers
molestus
(16 mg/l)
LC50 and LC99 for myrtle oil
respectively:
Moth
Ephestia kuehniella 12.74 and 29.43 μl/l air
Moth
Plodia
interpunctella
22.61 and 41.74 μl/l air
Milhau et al.
(1997)
Dell’Agli et
al. (2012)
Gauthier et
al. (1989)
Traboulsi et
al. (2002)
Ayvaz et al.
(2008)
49.58 and 76.07 μl/l air
Bean weevil
Acanthoscelides
obtectus
Hessian fly
2–20 lL/l air of M. communis
Lamiri et al.
Pharmacological
effect
Model organism
Dosage and application mode
of myrtle extract, oil or
Reference
compound
oil
(2001)
Mayetiola
destructor
Molluscicidal
Snails placed in 0.5 and 1.0 g/l
Deruaz and
Snail Biomphalaria of crude water extract and
Raynaud
glabrata
flavonoid fraction of M.
(1993)
communis
Protozoicidal
Trichomonas
vaginalis
Extract of Myrtus communis
caused death of T. vaginalis at
pH 4.65, but failed to do so at
pH 6.00
Mahdi et al.
(2006),
Azadbakht
et al. (2003)
Table options
The problem of potential toxicity also depends on the chemical composition of myrtle
extracts or essential oils used, e.g. toxicity of its constituting compounds. Traboulsi et al.
(2002) showed that thymol, carvacrol, (1R)-(+)-alpha-pinene and (1S)-(−)-alpha-pinene were
the most toxic (LC50 = 36–49 mg/l), while menthone, 1,8-cineole, linalool and terpineol
(LC50 = 156–194 mg/l) were less toxic. However, the fast metabolism and short half-life of
these active compounds raised the belief that there is a minimum risk of its accumulation in
body tissues (Kohlert et al. 2002). All these data are encouraging and suggest possible
medical application of extracts and essential oils of M. communis L., but yet further
investigations are necessary.
6. Conclusion
Many studies have demonstrated in vitro antimicrobial and antioxidant effectiveness of M.
communis L. extracts and essential oils, which is in agreement with current trends. Myrtle
seems to be a promising plant regarding alternative antimicrobials against increasing numbers
of pathogenic microorganisms resistant to conventional antibiotic and antioxidants which
should replace the synthetic ones. However, more studies are still needed to understand and
validate the mechanism of action of myrtle extracts and essential oils components. Also it is
important to precede work on other extraction materials and methods because of the fact that
extracting by different solvents may indicate different compounds and consequently different
extracts effects. Finally, clinical confirmation and pharmacological standardization are
required prior to their application as antimicrobial agents and antioxidants.
Acknowledgements
This study was supported by the Ministry of Science and Technological Development of
Republic of Serbia, Grant OI 172058. We thank Bob Blasdel (Faculty of Bioscience
Engineering, KU Leuven, Belgium), anonymous referees for useful comments and
suggestions, Prof. Michael Pascoe and Ljiljana Knezevic, PhD.
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