Industrial Crops & Products 128 (2019) 162–166

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Industrial Crops & Products

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Calamintha incana: Essential oil composition and biological activity T

a,⁎ b,⁎ c d
Jelena Popović-Djordjević , Mustafa Cengiz , Mehmet Sabih Ozer , Cengiz Sarikurkcu
a
University of Belgrade, Faculty of Agriculture, Belgrade, Serbia
b
Süleyman Demirel University, Faculty of Science and Literature, Department of Chemistry, Isparta, Turkey
c
Manisa Celal Bayar University, Faculty of Science and Literature, Department of Chemistry, Manisa, Turkey
d
Süleyman Demirel University, Faculty of Pharmacy, Department of Analytical Chemistry, Isparta, Turkey

ARTICLE INFO ABSTRACT

Keywords: The chemical composition of the essential oils (EO) isolated aerial parts of Calamintha incana (Sm.) Boiss. from
Calamintha incana Turkey was characterized by GC-FID and GC–MS analysis. The oxygenated monoterpenes trans-piperitone oxide
Essential oil (41.37%), piperitenone oxide (34.47%), piperitenone (6.67%), and monoterpene phenol thymol (3.37%) were
trans-Piperitone oxide found to be the major constituents of the essential oils of C. incana. The results of the antioxidant activity in
Antioxidant activity
phosphomolybdenum, radical scavenging (DPPH and ABTS) and reducing power activity (CUPRAC and FRAP) as
GC/MS analysis
well as metal chelating effects (ferrous ion chelating) showed that EO was the most potent in ABTS
(129.58 ± 2.21 mg TEs/g oil) and CUPRAC and FRAP (51.14 ± 0.05 and 53.63 ± 0.10 mg TEs/g, respec-
tively) assays. In enzymes inhibitory activity assays of EO, the best result was achieved for tyrosinase
(2.10 ± 0.30 mg KAEs/g oil). The results suggest that EO might be considered as a potential source of bioactive
agents to be used in food and pharmacological industries.

1. Introduction Lamiaceae, is perennial aromatic plants distributed in Central Asia,

From the ancient days, medicinal plants have been a valuable source
of various therapeutics, and still represent an essential fund of new
plant-derived natural products or their derivatives with significant
biological activities (Abu Khalaf, 2016; Atanasov et al., 2015). Enzyme
inhibitory activity of plant extracts and essential oils (EO) has been a
subject of many researches. Various classes of available drugs have
certain limitations, which impose the need for the development of a
new one. Besides the existing compounds, scaffolds and templates of
naturally occurring compounds have always presented key structures in
the process of new drug discovery (Popovic-Djordjevic et al., 2018).
Essential oils are progressively studied for the industrial use pur-
poses (chemical, cosmetic, food, fragrance and pharmaceutical) owing
to their potential bioactivities; antioxidant, repellent, antibacterial,
antifungal, analgesic, anti-inflammatory, antihypertensive and AChE
inhibitory (Abdelli et al., 2016; Ayvaz et al., 2010; Balkan et al., 2018;
Bouchra et al., 2003; Bozovic and Ragno, 2017; Marin et al., 2018;
Sarikurkcu et al., 2018).The origin of the species may have impact on
the chemical variability of the EOs (Marongiu et al., 2010). On the
other hand, biological activities of EO depend on the chemical com-
position, and are influenced by factors such as plant genotype and en-
vironmental conditions (Marin et al., 2018).
The genus Calamintha Miller species, which belong to the family
Europe, North Africa and Americas (Bonnier, 1959; Bown, 1995). In the
Flora of Turkey, the genus Calamintha is represented by nine species,
five being endemic to Turkey, and 12 taxa (Davis et al., 1982; Güner
et al., 2000). Calamintha species, known as “Miskotu, Dağ Nanesi, Ya-
bani Oğulotu etc”, are used for strengthening central nervous system
and as diaphoretic, emmenagogue, stimulant, expectorant, anti-
spasmodic, antiseptic, and digestive (Alan et al., 2009; Alan and Ocak,
2009; Baytop, 1999; Bown, 1995; Viney, 1994). In addition, some
species are reported to display strong antimicrobial activities (Mimica-
Dukić et al., 2004). The noticeable mint-like smell of Calamintha plants
contributed to their use in the traditional medicine of several Medi-
terranean countries as a mint alternative (Karousou et al., 2012). In the
Calamintha genus great variations in oil composition occur, both intra
and inter species. The most commonly represented components in the
oils of various Calamintha species are C(3)-oxygenated p-menthane
compounds (piperitone, piperitone oxide, piperitenone, piperitenone
oxide, pulegone, menthone and isomenthone) (Demirci et al., 2011;
Hanlidou et al., 1991; Karousou et al., 2012; Kitic et al., 2002;
Marongiu et al., 2010; Mimica-Dukić et al., 2004; Tümen et al., 1995).
Due to the potential market value and chemical diversity of
Calamintha plants many researches have been done in recent years.
Composition and biological activity of the essential oil of Calamintha
incana (Sm.) Boiss. from the area of Kestel, Bursa-Turkey were

⁎
Corresponding authors.
E-mail addresses: jelenadj@agrif.bg.ac.rs (J. Popović-Djordjević), cengizmustafa32@gmail.com (M.S. Ozer).

https://doi.org/10.1016/j.indcrop.2018.11.003
Received 30 August 2018; Received in revised form 30 October 2018; Accepted 1 November 2018
Available online 13 November 2018
0926-6690/ © 2018 Elsevier B.V. All rights reserved.
J. Popović-Djordjević et al. Industrial Crops & Products 128 (2019) 162–166

examined in this study. Phosphomolybdenum, ferrous ion chelating, Table 1

reducing power, and free radical scavenging assays were employed for Chemical composition of the essential oil from C. incana.
antioxidant activity. Essential oil of C. incana was tested for inhibition No RRIExpx RRILity RRILitz Compounds (%)w Identificationt
activity against acetylcholinesterase, butyrylcholinesterase, tyrosinase,
α-glucosidase, and α-amylase enzymes. To the best of our knowledge, 1 1201 1203a 1030 Limonene 0.14 1,2,3
2 1276 1280a 1024 p-Cymene 0.18 1,2,3
no data about antioxidant and enzyme inhibition activities of C. incana
3 1391 1393a 992 3-Octanol 0.37 1,2
essential oil have been reported up to date. 4 1501 1497b 1377 α-Copaene 0.11 1,2
5 1531 1535b 1385 β-Bourbonene 0.17 1,2
2. Materials and methods 6 1548 1553a 1097 Linalool 0.53 1,2,3
7 1612 1611a 1174 Terpinen-4-ol 1.46 1,2
8 1715 1719a 1167 Borneol 0.18 1,2,3
2.1. Plant material
9 1733 1733a 1262 cis-Piperitone oxide 0.71 1,2
10 1757 1754a – trans-Piperitone oxide 41.37 1,2
The aerial parts of Calamintha incana (Sm.) Boiss. were randomly 11 1830 – 1303 2-Hydroxypiperitone 0.95 1,2
collected under the forest area from Kestel, Bursa-Turkey on 29 March, 12 1948 1949a 1329 Piperitenone 6.67 1,2
13 1990 1983a 1363 Piperitenone oxide 34.47 1,2
2010 (40° 09' 14.3"N 29° 12' 01.6"E, 540–580 m). The plant was de-
14 2017 2008b 1579 Caryophyllene oxide 1.76 1,2,3
posited and identified by Prof. Dr. Hasan Ozcelik from the Department 15 2196 2198b 1293 Thymol 3.73 1,2,3
of Biology, Süleyman Demirel University, Isparta-Turkey. Total 92.80
Yield (ml/100 g dry 1.30
2.2. Isolation and analysis of the essential oil weight)

x
RRIExp; Relative retention indices calculated against n-alkanes on HP-in-
A British-type Clevenger apparatus (Ildam Ltd., Ankara-Turkey) was
nowax column.
used to obtain essential oil (EO) from the aerial parts of C. incana by y
RRILit; Relative retention indices on given in the literature for the com-
hydro-distillation. The EO was dried over sodium sulphate, filtrated, pound in similar columns (HP-innowax) and analysis conditions from the lit-
and then stored + 4 °C until tested and analyzed. Chemical character- erature [aSource: Demirci et al. (2011); bSource: Formisano et al. (2014)].
ization of the EO was carried out by GC-FID and GC–MS by using the z
RRILit; Relative retention indices on an HP-5MS column from the literature
analytical conditions reported previously (Sarikurkcu et al., 2015). (Adams, 2007).
w
Please see the supplementary file for the details. % calculated from FID data.
t
1: Relative retention index, 2:mass spectrum, 3:co-injection with authentic
2.3. Biological activity compound.

The biological activities of the EO were determined using anti-

oxidant and enzyme inhibition assays. Phosphomolybdenum (Zengin
et al., 2015a), ferrous ion chelating (Tepe et al., 2011), reducing power
[cupric ion reducing (CUPRAC) and ferric reducing antioxidant power
(FRAP)] (Apak et al., 2006; Kocak et al., 2016), and free radical
scavenging [on 1,1-diphenyl-2-picrylhydrazyl (DPPH·) radical and 2,2-
azino-bis (3-ethylbenzothiazloine-6-sulphonic acid) radical cation
(ABTS·+)] (Zengin et al., 2015b) tests were used for antioxidant ac-
tivity. Inhibition effects of the EO against acetylcholinesterase (AChE),
butyrylcholinesterase (BChE), tyrosinase, α-glucosidase, and α-amylase
were also investigated for enzyme inhibition assays (Zengin et al.,
2015a). Please see the supplementary file for the details.
The activity is expressed as both IC50 value (the sample con-
centration providing 50% of radical scavenging/ferrous ion chelating/
enzyme inhibition or 0.500 absorbance for the reducing power/phos-
phomolybdenum assays, respectively) and standard equivalents (μg/g
extract). Trolox and EDTA were used as positive controls for anti-
oxidant assays, and galanthamine, kojic acid, and acarbose were used
for enzymatic assays.
2.4. Statistical analysis
All of the experiments of biological activity were repeated in tri-
plicate and the results were given as the mean value and the standard
deviation (mean ± SD). The results with IC50 values were analyzed
statistically with Student’s t-test (α = 0.01) by using the SPSS v22.0
software
3. Results and discussion
3.1. Chemical composition of the EO
piperitenone oxide (34.47%) and piperitenone (6.67%) as the main
constituents, and monoterpene phenol thymol (3.37%). Other detected
compounds were present in concentrations less than 2% (Table 1).
Available data about the composition of the oil of C. incana are very
limited. Tümen et al. (1995) reported that piperitenone oxide, limonene
and piperitone oxide (as a mixture of isomers) were the predominant
components of the EO of this species, with 66.60, 6.22 and 5.91%,
respectively.
It could be noticed that trans-piperitone oxide was found only in C.
nepeta subsp. glandulosa (Demirci et al., 2011), whereas its stereoisomer
cis-piperitone oxide was reported in various Calamintha species such as
in C. sylvatica subsp. sylvatica (Kitic et al., 2001), C. sylvatica (Mimica-
Dukić et al., 2004), and C. vardarensis (Kitic et al., 2002). Hanlidou
et al. (1991) reported that piperitone oxide was found in high con-
centrations (62.9 and 67.6%) in EO of two C. menthifolia populations.
Piperitone is a natural monoterpene ketone with fresh peppermint
odor, which occurs in essential oils from various leaves. Mentha and
Eucalyptus genera comprise a large number of species rich in piperitone
(Ravid et al., 1994).
Piperitenone oxide isolated from essential oil of a new genotype,
Mentha spicata var. viridis, has proved to be very efficient for larvicidal,
ovicidal, oviposition-deterrent, developmental toxicity, and repellent
properties against Anopheles stephensi a well-known malarial disease
agent (Tripathi et al., 2004). Antibacterial activity of this compound
against various pathogens is also reported (Bozovic et al., 2015).
Thymol has been identified as a molecule with antioxidative prop-
erties (Deighton et al., 1993). Natural products which are a source of
antioxidant molecules such as thymol, may be of particular interest in
food production and storage processes which require the use of effec-
tive antioxidants.

In the C. incana EO from the forest area of Kestel (Bursa) only fifteen 3.2. Antioxidant activity
compounds were detected, which accounted for 92.80% of the total
composition. The EO was characterized by a high percentage of the The application of different antioxidant assays is necessary as it is
oxygenated monoterpenes, namely trans-piperitone oxide (41.37%), difficult to assess the antioxidant activity of a product based on a single

163
J. Popović-Djordjević et al.
Table 2
Antioxidant activities of the essential oil from C. incana by different assays.x
Assays Antioxidant activity
Phosphomolybdenum (mmol TEs/g oil) 5.52 ± 0.26
Ferrous ion chelating (mg EDTAEs/g oil) 1.94 ± 0.14
DPPH radical scavenging (mg TEs/g oil) 19.28 ± 0.74
ABTS radical cation scavenging (mg TEs/g oil) 129.58 ± 2.21
CUPRAC reducing power (mg TEs/g oil) 51.14 ± 0.05
FRAP reducing power (mg TEs/g oil) 53.63 ± 0.10
x
TEs and EDTAEs; trolox and ethylenediaminetetraacetic acid (disodium
salt) equivalents, respectively.
method. In order to obtain a more comprehensive picture about anti-
oxidant potential of C. incana EO, several methods were employed and
the results are given in Table 2. The radical scavenging ability of ex-
amined EO was six-fold higher in ABTS assay (129.58 ± 0.74) than in
DPPH radical (19.28 ± 0.74) assay, expressed as trolox equivalents per
gram of oil. The result obtained for C. incana EO in DPPH assay were
comparable to the activity of Chenopodium bortys EO (12.37–20.72 mg
TEs/g oil) (Ozer et al., 2017). On the other hand, its activity (ABTS
assay) was substantially higher than C. bortys EOs (4.95–9.89 mg TEs/g
oil) (Ozer et al., 2017) and Origanum vulgare subsp. hirtum EO (9.63 mg
TEs/g oil) (Sarikurkcu et al., 2015).
Reducing power assays FRAP and CUPRAC may provide important
information about EO antioxidant power. The antioxidant activity of C.
incana EO was 51.14 and 53.63 mg TEs/g oil in FRAP and CUPRAC,
respectively (Table 2), which is higher reducing power when compared
to C. bortys EO (9.89–18.45 mg TEs/g oil for FRAP and 33.91–41.91 mg
TEs/g oil for CUPRAC) (Ozer et al., 2017).
In the phosphomolybdenum assay, the EO showed weak antioxidant
capacity (5.52 ± 0.26 mmol TEs/g oil) but comparable to the activity
of C. bortys EO (6.52–7.49 mg TEs/g oil) (Ozer et al., 2017).
The chelating effect of the EO was evaluated by ferrous ion che-
lating test and found as 1.94 ± 0.14 mg EDTAEs per gram of oil, in-
dicating poor metal chelating activity, but still higher than those of
Origanum vulgare subsp. vulgare EO (1.34 ± 0.21 mg EDTAEs/g oil)
(Sarikurkcu et al., 2015).
Antioxidant activities of EO were also presented as IC50 values,
which correspond to the concentration of the oil (mg/ml) required to
inhibit 50% of the initial concentration of oxidant (Table 3). IC50 values
of essential oil were significantly lower activity than those of trolox and
EDTA which are used as positive control, except for phosphomo-
lybdenum test (p < 0.01).
A number of reports are available in the literature showing that
oxygenated monoterpenes such as piperitenone, piperitenone oxide,
linalool, thymol, and carvacrol are responsible for the antioxidant po-
tential of plant oils (Barbieri et al., 2016; Bicas et al., 2011; Bozovic
et al., 2015; Miguel, 2010). C. incana EO is mainly constituted by trans-
piperitone oxide and piperitenone oxide. These findings support the
view that certain aromatic plants are potential sources of antioxidants.
In this sense, C. incana EO can be a good natural antioxidant source for
use as a nutraceutical, protective or cosmeceutical.
Table 3
Antioxidant activities of standards and the essential oil from C. incana by different assays.x
Samples Phosphomolybdenum DPPH radical
a b
Essential oil (IC50: mg/ml) 0.169 ± 0.011 3.67 ± 0.02
Trolox (IC50: mg/ml) 0.233 ± 0.005a 0.068 ± 0.004a
EDTA (IC50: mg/ml) – –
x
Different superscripts in the same column indicate significant differences (p < 0.01). EDTA, ethylenediaminetetraacetic acid (disodium salt).
164
Industrial Crops & Products 128 (2019) 162–166
Table 4
Inhibitory effect of the essential oil from C. incana by different assays.x
Assays Inhibitory activity
AChE (mg GALAEs/g oil) na
BChE (mg GALAEs/g oil) na
Tyrosinase (mg KAEs/g oil) 2.10 ± 0.30
α-Amylase (mmol ACEs/g oil) 0.34 ± 0.10
α-Glucosidase (mmol ACEs/g oil) 0.10 ± 0.01
x
GALAEs, KAEs, and ACEs; galanthamine, kojic acid, and acarbose
equivalents, respectively. na, not active.
3.3. Enzyme inhibitory activity
In this work we examined inhibitory potential of C. incana against
acetylcholinesterase (AChE), butyrylcholinesterase (BuChE, tyrosinase,
α-amylase and α-glucosidase enzymes using in vitro models (Table 4).
Essential oil of C. incana did not exert inhibitory activity against acetyl-
cholinesterase (AChE) and butyrylcholinesterase (BChE), enzymes as-
sociated with Alzheimer’s (the most common form of dementia) and
Parkinson’s disease (Sarikurkcu et al., 2014).
The highest inhibitory activity was observed against tyrosinase
2.10 ± 0.30 (expressed as mg of kojic acid equivalents per gram of
EO). This result indicated its higher activity than reported for C. bortys
EO (Ozer et al., 2017). Tyrosinase (polyphenol oxidase) is a multi-
functional copper-containing oxidase which catalyzes the formation of
melanin from tyrosine. Besides, this enzyme is associated with neuro-
degenerative process in Parkinson's disease, melanogenesis in mammals
and enzymatic browning in plants. Hence, tyrosinase inhibitors have
become increasingly important in the field of medicine, agriculture, and
cosmetics (Maghsoudi et al., 2013; Sawant et al., 2013).
The inhibition of α-glucosidase and α-amylase which are enzymes
involved in the hydrolyse of polysaccharides, is an important step in
controlling blood glucose level, and plants are known for their anti-
diabetic properties (Arumugam et al., 2013). Inhibitory activity of C.
incana EO against α-amylase and α-glucosidase was moderate; 0.34 and
0.10 mmol of acarbose equivalents per gram of EO, respectively. When
the results for α-amylase inhibition were compared, C. incana EO was a
more potent inhibitor then both Origanum vulgare subspecies (subsp.
vulgare and subsp. hirtum) EO (Sarikurkcu et al., 2015).
Results obtained from enzyme inhibitory activity assays with the
IC50 values in mg/ml are also summarized in Table 5. The EO showed
significant activity against α-amylase, with IC50 values very similar to
standard drug acarbose, while exhibiting very low inhibition against
tyrosinase and α-glucosidase (p < 0.01). The inhibitory activity of C.
incana EO against α-amylase indicates its potential therapeutic use re-
levant for the treatment of diabetes mellitus type 2.
4. Conclusions
In summary, trans-piperitone oxide, piperitenone oxide, piper-
itenone and thymol represented 85.88% of all C. incana EO
ABTS radical CUPRAC reducing FRAP reducing Metal chelating
b b b
1.45 ± 0.03 1.13 ± 0.001 1.49 ± 0.003 5.40 ± 0.39b
0.19 ± 0.01a 0.058 ± 0.001a 0.08 ± 0.003a –
– – – 0.026 ± 0.001a
J. Popović-Djordjević et al.
Table 5
Inhibitory activities of standards and the essential oil from C. incana by different assays.x
Samples Tyrosinase α-Amylase
b b
Essential oil (IC50: mg/ml) 61.57 ± 8.70 4.85 ± 0.13
Kojic acid (IC50: mg/ml) 0.128 ± 0.001a – –
Acarbose (IC50: mg/ml) – 1.37 ± 0.01a
Galanthamine (IC50: mg/ml) – –
x
Different superscripts in the same column indicate significant differences (p < 0.01). na, not active.
constituents. A good radical scavenging and reducing power ability as
well as significant activity against α-amylase of C. incana EO were
observed in the study, indicating its potential for use as functional food
sources or therapeutic. The present findings improved the knowledge of
the composition and biological activity of C. incana EO which has been
insufficiently investigated up to now (or reported herein for the first
time). However, further studies are needed for obtaining a deeper in-
sight into contribution of particular constituents to bioactivity of the
essential oil.
Acknowledgement
This work was partly performed within the project No. 172032
supported by the Ministry of Education, Science and Technological
Development of the Republic of Serbia.
Appendix A. Supplementary data
Supplementary material related to this article can be found, in the
online version, at doi:https://doi.org/10.1016/j.indcrop.2018.11.003.
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