Food Measure
DOI 10.1007/s11694-017-9522-5
ORIGINAL PAPER
Aroma constituents of shade-dried aerial parts of Iranian dill
(Anethum graveolens L.) and savory (Satureja sahendica Bornm.)
by solvent-assisted lavor evaporation technique
Asghar Amanpour1 · Hasim Kelebek2 · Serkan Selli1,3
Received: 23 June 2016 / Accepted: 3 April 2017
© Springer Science+Business Media New York 2017
Abstract The aroma proile of shade-dried aerial part
from Iranian dill (Anethum graveolens L.) and Savory
(Satureja sahendica Bornm.) plants was analyzed by the
gas chromatography–mass spectrometry (GC–MS) and
gas chromatography–lame ionization detector (GC–FID).
For the irst time in these aromatic plants, the solventassisted lavour evaporation (SAFE) extraction method
with dichloromethane was used prior to GC–MS. A total
of 40 and 26 aroma compounds was identiied in dill and
savory. Dill contained 271.52 µg/g total amount of aroma
compounds, which included terpenes (28), aldehydes (3),
alcohol (1), acids (3), volatile phenols (3), ketone (1) and
norisoprenoid (1). Savory possessed 10,547.16 µg/g total
amount of aroma compounds, including terpenes (20),
alcohol (1) and volatile phenols (5). Of all aroma compounds detected in both plants, terpenes were quantitatively the most dominant aroma volatiles. In the overall
aroma volatiles, α-phellandrene (160.0 µg/g) together with
sabinene (26.5 µg/g), D-carvone (16.2 µg/g), DL-limonene
(12.3 µg/g) and dill ether (7.8 µg/g) in dill and γ-terpinene
(6236.83 µg/g) along with carvacrol (3239.19 µg/g),
α-pinene (267.08 µg/g), α-thujene (219.36 µg/g) and
β-bisabolene (130.8 µg/g) in savory were the major
compounds.
* Serkan Selli
sselli@cu.edu.tr
1
Department of Biotechnology, Institute of Natural
and Applied Sciences, Cukurova University, 01330 Adana,
Turkey
2
Department of Food Engineering, Faculty of Engineering
and Natural Sciences, Adana Science and Technology
University, 01110 Adana, Turkey
3
Department of Food Engineering, Faculty of Agriculture,
Cukurova University, 01330 Adana, Turkey
Keywords Aroma proile · SAFE technique · GC-MS ·
Dill (Anethum graveolens L.) · Savory (Satureja sahendica
Bornm.)
Introduction
Dill (Anethum graveolens L.) is a yearly herb of the Apiaceae family found particularly in regions with warm and
tropical climates [1]. Leaves, stems, and fruits of dill are
excessively used in diferent applications of the food industry, especially for their typical taste as well as pleasant
and spicy aroma [2], and also for the medical use [1]. It
is an important condiment crop from which both herb and
seed have been extensively used in all kinds of lavouring
including those for baking mixes, sauces, salads, and seafoods [3]. Additionally, the experimental studies demonstrated the antimicrobial, stomachic, antioxidant, carminative, insecticidal properties, and cardiovascular beneits of
dill [4].
Savory (Satureja L.) is included in the main taxa of the
Lamiaceae (Nepetoideae) family involving more than 200
species of aromatic herbs and shrubs, basically distributed
in the Asian and Mediterranean zones [5, 6]. Fourteen
species are presented in the lora of Iran, in the northern,
northwestern, and western districts. Eight of them comprising Satureja edmondii, Satureja intermedia, Satureja
isophylla, Satureja kallarica, Satureja bakhtiarica, Satureja khusstanica and Satureja sahendica are vernacular to
Iran [5, 6]. The genus S. sahendica in Persian is known as
“Marze” and “Marze-Sahandi,” respectively [6]. Satureja
sahendica Bornm. is a habitual, ramiied, and rich aromatic
herb growing in the western and northwestern areas, particularly in the Sahand Mountains in the northwest of Iran
[6]. The volatile oils of the genus Satureja is isolated from
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A. Amanpour et al.
their aerial parts possess aromatic and medicinal features
[5, 6]. The fresh and dried leaves and vegetative parts of
stems have been consumed in many culinary aspects such
as stuings, stews, dishes containing meat and poultry, sausages, and greengroceries [7].
Furthermore, the aerial sections of some Satureja species have been used in the folk medicine for curing diarrhea, inlammation of the stomach and intestines, wounds,
urinary infections [5], and asthma [6] and as antimicrobial,
tonic, antiseptic, latulent, digestive, diuretic, carminative,
and aphrodisiac drugs [6]. Additionally, biological activities entailing antioxidant, antifungal, antibacterial, antidiabetic and anti-inlammatory functions were also evidenced
in savory [5].
Aroma is a complicated structure of a big number of low
molecular weight volatile compounds whose combination
is characteristic to species and often to the variety of plants
[7]. These two diferent plant varieties, dill and savory, are
extensively used in the daily diet of the Iranian general
population as lavouring agents and spices to improve the
lavour of food. Both of them are aromatic and have their
own peculiar lavour with multiple volatile compounds in
their leaves. Most spices are commonly sold dried because
of high water content in the fresh states which leads to
intensive deterioration caused by microbial growth and
biochemical reactions. Drying processes stabilizes spices
microbiologically by reducing the water activity (aw) values under the threshold for microbial development (0.6)
[8]. Some volatile compounds vaporize during air-drying,
whereas others are somewhat retained, and some oxidation
products appear during drying.
When spices are used as marinades or as seasoning for
foods, the dried vegetal crop is added directly. The volatile oil composition of both dill and savory has been widely
studied [2, 3, 6, 7, 9–16]. The most abundant volatiles
determined in dill are terpene compounds [17]. Three
main compounds, carvone, α-phellandrene, and limonene,
have been detected in dill aroma, but their amounts varied
extensively [9]. Within these, α-phellandrene, the main
compound of dill aroma greatly contributes to the sensory
impression of dill herb [18]. In the case of savory, previous studies in various Satureja species indicated the big
disagreement among both chemical compositions and their
essential oils content.
For instance, the main compounds of the genus Satureja were carvacrol (40.8%) and γ-terpinene (26.4%)
in Satureja boissieri oil from Turkey; pulegone (64.3%)
and menthone (20.2%) in Satureja brownei oil from
Venezuela; piperitone oxide in Satureja parvifolia oil
from Argentina; γ-terpinene, β-caryophyllene and germacrene D in Satureja boliviana oil and menthone and
13
isomenthone in Satureja brevicalix oil from Peru; neral,
geranial and farnesene in Satureja punctate, thymol
and carvacrol in Satureja cuneifolia oil, Germacrene
D in Satureja coerulea oil from Turkey; carvacrol and
γ-terpinene in Satureja hortensis oil and γ-terpinene
(42.2%) and carvacrol (31.9%) in S. sahendica Bornm. oil
from Iran [6, 12]. Volatiles are dependent on many factors, such as plant part, time of harvest, harvested plant
part, extraction method, type of cultivar or genotype,
geographic origin, storage conditions, and climate [19].
Drying is an efective method that prolongs the shelf life
of the product by slowing the growth of microorganisms
and preventing biochemical reactions that may impact
sensory attributes [20].
There are very few surveys found on the isolation of
volatile compounds directly from spices. Concerning the
European Pharmacopoeia [21], volatile oils are extracts
separated from aromatic plants only by distillation procedures such as hydrodistillation. Further extracts obtained
from aromatic plants by other techniques, even entailing
volatile compounds, should not be considered as volatile
oils [14]. Hydrodistillation (Clevenger and/or steam distillation apparatus) and organic solvent extraction (Soxhlet extractor) have both been extensively applied for the
separation of volatile oils from spices as the conventional
methods.
Nevertheless, these two extraction methods both
tend to degrade the original spice lavour and lose volatile compounds owing to the high temperatures used. In
other words, most of the lavour compounds in spices are
consisted in their volatile oils and are changed or damaged upon heating or air oxidation [22]. Moreover, new
lavours can be progressed from non-volatile precursors
by Maillard reaction, carotenoid degradation, and lipid
oxidation [23]. These limitations may be overcome using
appropriate and novel extraction techniques. Thus, the
appropriate extraction technique must be selected with
the aim of producing aromatic extracts with odour as
close as possible to that of the studied sample.
Under these circumstances, present research reports
the results of shade-dried aerial parts of dill (A. graveolens L.) and savory (S. sahendica Bornm.) aroma proile
collected from the city of Tabriz in East Azerbaijan Province, Iran. In this investigation, the solvent-assisted lavour extraction (SAFE) method was chosen as the aroma
extraction method. Thanks to low pressure is used in this
method, isolation of volatiles at low temperatures such as
40 °C can be achieved, which intercepts the formation of
artifacts. It has already demonstrated its reliability for the
extraction of volatile compounds in Iranian safron and
golpar spices [24, 25], orange juice [26], and cofee [27].
Aroma constituents of shade-dried aerial parts of Iranian dill (Anethum graveolens L.) and…
Gas chromatography (GC) coupled with lame ionization detector (FID) and mass spectrometry (MS) has been
applied in quantiication and identiication of the aroma
compounds, respectively.
Materials and methods
Plant material
The aerial parts of both dill (A. graveolens L.) and savory (S.
sahendica Bornm.) were collected from Tabriz at the end of
May and September in 2015. The collected materials were
dried at room temperature away from sun light, packed into
polyethylene bags, and kept at 4 °C for further use.
Isolation of volatile compounds
The isolation of volatiles was conducted in the dichloromethane being an eicacious solvent for the separation of
volatiles in fruits and plants [28]. The volatiles exist in the
Iranian dill and savory were isolated under vacuum (10−3
Pa; Vacuubrand DCP 3000, Wertheim, Germany) using the
solvent-assisted lavour evaporation (SAFE) unit (Gläsblaserei Bahr, Manching, Germany). The isolation technique
was altered from our earlier research [24]. Briely, a monotonic powder of shade-dried aerial sections of both samples was separately prepared by applying porcelain mortar
at room temperature. Before extraction, 7 g of each powdered sample containing 100 mL of dichloromethane plus
5 µL of 2-octanol as an internal standard were placed into a
500-mL lask. The details of the extraction technique were
entirely explained in our earlier research [24, 25]. Each
sample was extracted in triplicate. The concentrations of
volatiles were calculated according to internal standard.
GC–FID and GC–MS analyses of volatile compounds
An Agilent 6890 GC was equipped with a FID (Wilmington, DE, USA) and an Agilent 5973-network-mass selective
detector (MSD). The helium as a carrier gas was used with
1.5 mL/min low rate. The oven start temperature was 50 °C
(1 min), the following gradient was 5 °C/min, and then at
a rate of 8 °C/min to 260 °C with a inal hold at 260 °C for
5 min (DB-WAX column). GC eluent was split 1:1 among
the FID and MSD. A mass spectra in the electron ionization mode were recorded at 70 eV and a mass/charge range
of 30–300 amu at 2.0 scan s−1 scan rate. The identiication
of compounds was comprised of the following parameters:
retention indices, commercial spectra database (Wiley 6 and
NIST 98), an internal library created from our previous studies, and standard reference compounds.
Sensory and statistical analysis of the dill and savory
plants and their extracts
Panel
The panel consisted of nine assessors (three females and
six males between 25 and 49 years of age) from the Biotechnology Laboratory at the Department of Food Engineering, University of Cukurova. The assessors were
familiar with the dill and savory aroma and also formerly
trained in the scent distinction and sensory assessment
methods, and had the experiences in the GC–MS.
Preparation and presentation of the samples
Various ways could be applied to estimate the representativeness of the aroma of odorous extracts belonging to
this kind of study. In the current essay, a cardboard smelling strip (reference 7140 BPSI, Granger-Veyron, Lyas,
France) was used to investigate the representativeness
of the extracts acquired using the SAFE extraction technique. These cardboards have already evidenced positive
outcomes for the representativeness test in the juice of
orange [28] and Iranian safron spice [24]. As a reference,
a 1 g of each powdered sample was inserted in a 25 mL
brown coded lask. Odorous extracts of samples acquired
using the SAFE technique were adsorbed onto the cardboard. The detailed procedure was given in our earlier
investigation [24].
Descriptive analysis
Two diferent lists separately for each plant such as nine
descriptors composed of fresh, green, herbal, citrusy,
minty, woody, dill, spicy and oily for dill and other nine
descriptors consisted of fresh, green, herbal, citrusy,
minty, woody, balsamic, loral and earthy for savory that
describe their characteristic aroma were deined by the
trained and expert panelists and subsequently applied to
describe their extracts. More details are available in our
previous study [24].
Statistical analysis
The statistical method used for the sensorial data analysis
was an independent-samples analysis of variance (t test)
to compare the sensory proile of each extract obtained
from the SAFE method with that of their original samples. All the data in this experiment are presented as
the average of nine replicates. Statistical analysis was
13
A. Amanpour et al.
performed using SPSS statistics software version 22.0
(SPSS Inc., Chicago, Illinois, USA).
Results and discussion
Sensory analysis
Odor sensory proiles
The aromatic extracts of both plants isolated by the SAFE
technique were compared to the reference samples, dill and
savory plants, by the nine panelists. From the panelist group
point of view, the outcomes of the similarity and intensity
evaluation of the odorous isolation evidenced an extract
representing the characteristic aroma of the plants, when
a droplet of the aroma extract was vaporized on a strip of
smelling paper. Figures 1 and 2 displays the two diferent
principal intensity groupings of the both original samples
and their extracts depicted on a spider graph applying nine
descriptors. Each rating was separately applied by the panelists to depict the characteristic odor of the shade-dried
aerial parts of the dill and savory plants and their extracts.
To the best of our knowledge, the descriptive analysis of these both samples were used for the irst time to
depict their characteristic odour. As can be demonstrated
in Figs. 1 and 2, it appears that the sensory proile of each
extract obtained from the SAFE method is analogous to
that of their original samples. No variations were statistically detected between the aromatic extract using the
SAFE isolation technique and original sample for the nine
descriptors in both samples (p < 0.01). Of descriptors in the
Fig. 1 Odour sensory features of the dill plant and its extract
13
Fig. 2 Odour sensory features of the savory plant and its extract
dill sample (Fig. 1), herbal, dill and spicy aroma descriptors had the largest scores and the rest of the descriptors
with the lowest scores were proved. In the case of the
savory sample (Fig. 2), fresh, herbal, minty and loral odor
descriptors with the highest scores and green, citrusy,
woody, balsamic and earthy notes with the lowest scores
were evidenced.
Aroma compositions of dill and savory
The volatile compounds identiied in the shade-dried aerial
parts of the dill and savory plants and linear retention index
values on the DB-Wax column for these compounds were
presented in Table 1. Mean values (µg/g) of the GC analyses of triplicate extractions and standard deviations were
reported. A total of 40 and 26 compounds were identiied
and quantiied in the dill and savory (Fig. 3), most of which
have already been identiied by previous studies in both different countries and diverse parts of dill and savory plant’
volatile oil [2, 3, 6, 7, 9–16]. Dill contained 271.52 µg/g
of the total amount of volatile compounds, which included
terpenes (28), aldehydes (3), alcohol (1), acids (3), volatile
phenol (3), ketone (1) and norisoprenoid (1).
Of all volatile compounds detected in the dill, terpenes
were quantiied as the most prevailing volatile compounds,
followed by the acids (isovaleric, hexanoic and octanoic
acid), aldehydes (nonanal, benzaldehyde and anisaldehyde), volatile phenols (isoanethole, anethol and isoeugenol), an alcohol (benzyl alcohol), a ketone (bornyl acetate)
and a norisoprenoid (β-ionone epoxide). Savory contained
10,547.16 µg/g of the total concentration of volatile compounds, comprising the terpenes (20), an alcohol (1) and
Aroma constituents of shade-dried aerial parts of Iranian dill (Anethum graveolens L.) and…
Table 1 Aroma compounds of
the shade-dried aerial parts of
the Iranian dill (A. graveolens
L.) and savory (S. sahendica
Bornm.) using the SAFE
technique
No.
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
Volatile compounds
α-Pinene
α-Thujene
β-Pinene
(+)-2-Carene
(+)-4-Carene
α-Phellandrene
α-Terpinene
DL-Limonene
Sabinene
γ-Terpinene
(E)-β-Ocimene
α-Terpinolene
Nonanal
α-Ocimene
1-Octen-3-ol
(E)-Sabinene hydrate
(Z)-Sabinene hydrate
L-Menthone
Benzaldehyde
Dill ether
α-Copaene
Isopulegone
Bornyl acetate
Dihydrocarvone
Calarene
1-Terpineol
4-Terpineol
Methylcarvacrol
(E)-Caryophyllene
Aromadendrene
α-Caryophyllene
Pulegone
Isoborneol
Isovaleric acid
Isoanethole
Carvotanacetone
δ-Elemene
α-Terpineol
β-Bisabolene
D-Carvone
β-Cubebene
β-sesquiphellandrene
(Z)-γ-Bisabolene
α-Curcumene
Anethol
Hexanoic acid
Benzyl alcohol
Carvacrol acetate
β-Ionone epoxide
LRIa
1012
1017
1100
1110
1128
1167
1178
1186
1231
1246
1279
1284
1388
1404
1445
1460
1466
1474
1516
1521
1526
1540
1544
1549
1554
1575
1579
1590
1596
1627
1632
1644
1664
1665
1670
1683
1688
1691
1720
1726
1761
1762
1767
1773
1833
1840
1870
1880
1957
Concentrationb (mean ± SD)
Dill
Savory
4.49 ± 0.62
nd
0.66 ± 0.04
nd
nd
160.0 ± 5.24
1.24 ± 0.01
12.3 ± 1.56
26.5 ± 3.24
1.69 ± 0.06
0.26 ± 0.03
0.72 ± 0.06
0.30 ± 0.05
nd
nd
0.82 ± 0.14
nd
2.62 ± 1.92
0.40 ± 0.05
7.80 ± 0.35
0.70 ± 0.38
0.30 ± 0.04
0.44 ± 0.08
1.03 ± 0.14
1.82 ± 0.91
0.43 ± 0.06
nd
nd
nd
nd
nd
6.67 ± 0.56
nd
1.62 ± 0.61
2.06 ± 0.14
0.45 ± 0.16
1.00 ± 0.30
nd
nd
16.2 ± 2.21
1.19 ± 1.26
nd
nd
0.60 ± 0.11
0.17 ± 0.01
3.22 ± 0.90
0.49 ± 0.14
nd
3.82 ± 1.32
267.08 ± 0.08
219.36 ± 0.95
82.34 ± 0.32
82.04 ± 1.6
22.85 ± 0.48
nd
nd
nd
nd
6236.83 ± 2.5
nd
10.34 ± 0.52
nd
1.06 ± 0.69
9.72 ± 1.27
17.89 ± 1.29
23.1 ± 1.69
nd
nd
nd
nd
nd
nd
nd
nd
nd
7.54 ± 0.51
11.07 ± 0.3
98.4 ± 1.48
22.57 ± 0.3
5.75 ± 0.48
nd
10.7 ± 0.32
nd
nd
nd
nd
12.8 ± 1.47
130.8 ± 1.93
nd
nd
1.55 ± 0.12
5 ± 0.04
nd
nd
nd
nd
3.47 ± 0.67
nd
Identiicationc
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, tent
LRI, MS, tent
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, tent
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, tent
LRI, MS, Std
LRI, MS, tent
LRI, MS, tent
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, tent
LRI, MS, Std
LRI, MS, tent
LRI, MS, Std
LRI, MS, tent
LRI, MS, Std
LRI, MS, Std
LRI, MS, tent
LRI, MS, tent
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, tent
LRI, MS, tent
LRI, MS, tent
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, tent
13
A. Amanpour et al.
Table 1 (continued)
No.
50
51
52
53
54
55
56
57
58
59
Volatile compounds
Anisaldehyde
ρ-cresol
Octanoic acid
Eugenol
Isoeugenol
Thymol
Carvacrol
ρ-Cumenol
Myristicin
Dill apiole
TOTAL
LRIa
2023
2078
2083
2169
2180
2188
2206
2211
2216
2226
Concentrationb (mean ± SD)
Dill
Savory
0.16 ± 0.05
nd
0.40 ± 0.12
nd
0.18 ± 0.19
0.48 ± 0.18
0.45 ± 0.16
0.94 ± 0.84
0.43 ± 0.23
6.66 ± 2.77
271.52
nd
0.26 ± 0.08
nd
0.25 ± 0.16
nd
25.2 ± 0.3
3239.19 ± 1.44
nd
nd
nd
10547.16
Identiicationc
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, Std
LRI, MS, tent
LRI, MS, tent
a
LRI—Retention indices on DB-WAX column
b
Concentration—Mean values based on three repetitions as µg/g; nd not determined
c
Identiication: Methods of identiication; LRI linear retention index, MS tent. tentatively identiied by MS,
Std chemical standard; When only MS or LRI is available for the identiication of a compounds, it must be
considered as an attempt of identiication
Fig. 3 The gas chromatography-mass spectrometry (GC–MS) chromatograms of Dill and Savory (peak numbers refer to aroma compounds represented in Table 1)
13
Aroma constituents of shade-dried aerial parts of Iranian dill (Anethum graveolens L.) and…
volatile phenols (5). The most prevailing volatile compounds in savory extracts were terpenes, followed by volatile phenols (methylcarvacrol, carvacrol acetate, ρ-cresol,
eugenol and thymol) and an alcohol (1-octen-3-ol). Aromatic plants are mostly used in the folk medicine, and
volatile oils and volatile compounds isolated from them are
extensively used as the antioxidants and anti-inlammatory
agents. Several anti-inlammatory, digestive, antinecrotic,
neuroprotective, and hepatoprotective drugs have recently
been demonstrated to possess an antioxidant and/or radicalscavenging mechanism as a section of their activity [29].
In the overall aromatic compounds of the dill in this
study, the α-phellandrene (160.0 µg/g) is the major compound together with the sabinene (26.5 µg/g), D-carvone
(16.2 µg/g), DL-limonene (12.3 µg/g), dill ether (7.80 µg/g),
pulegone (6.67 µg/g), dill apiole (6.66 µg/g), α-pinene
(4.49 µg/g), β-ionone epoxide (3.82 µg/g) and hexanoic
acid (3.22 µg/g). In general, the α-phellandrene, D-carvone
and DL-limonene are impact compounds of many essential
dill oils and are responsible especially for the aroma and
biological efects [10]. The most abundant volatiles determined in the dill are terpenes [17]. α-Phellandrene, the
main compound of dill aroma greatly contributes to the
sensory impression of the dill herb [18].
In our research, terpenes were also quantitatively
(258.4 µg/g) the leading volatile compounds in the dill, representing 95.2% of the total volatile proile analyzed. The
amount of the α-phellandrene (58.93%) shown in Table 1
is much higher than that reported in the Iranian dill essential oil (19.1%) [30]. Of all aroma compounds discovered in the savory, the γ-terpinene (6236.83 µg/g) is the
major compound along with the carvacrol (3239.19 µg/g),
α-pinene (267.08 µg/g), α-thujene (219.36 µg/g) and
β-bisabolene (130.8 µg/g). In an earlier study, the investigated S. sahendica Bornm volatile oil using the hydrodistillation extraction method was detected to be rich in terpenes
with substantial contents of the γ-terpinene and carvacrol,
and they contained approximately 77% of the determined
compounds and were the most predominant compounds of
the oil [6]. γ-Terpinene as a volatile oil indicates antimicrobial characters against diferent human pathogens [31].
The antioxidant, anti-inlammatory, and anti-proliferative
activities of γ-terpinene is also investigated [32]. There
are diverse agents that can afect the volatile compounds
during the drying process; for instance, the temperature
reached, the interaction among volatiles and water vapor,
and the hydrophobic nature of volatiles [33].
Terpenes
Terpenes quantitatively represent the main class of aroma
compounds in both tested samples, accounting for 95.18
and 68.8% of the total aroma compounds determined in the
dill and savory. Plenty of the terpene compounds are direct
products of terpene synthases, while others are formed
through changes of the primary terpene skeletons made by
terpene synthases by the hydroxylation, dehydrogenation,
acylation, and other reactions [34].
α-Pinene together with the β-pinene, α-phellandrene,
α-terpinene, DL-limonene, sabinene, γ-terpinene, (E)-βocimene, α-terpinolene, L-menthone, (E)-sabinene hydrate,
dill ether, α-copaene, isopulegone, dihydrocarvone, calarene, 1-terpineol, pulegone, carvotanacetone, δ-elemene,
D-carvone, β-cubebene, α-curcumene, thymol, carvacrol,
ρ-cumenol, myristicin and dill apiole were determined
in the dill sample. Most of these terpenes were identiied
in the dill from diferent countries in previous studies [1,
3, 9, 35, 36]. Among the higher terpenes, α-phellandrene
(160 µg/g) was detected as the highest proportion in the
dill aromatic extract, followed by the sabinene (26.5 µg/g),
D-carvone (16.2 µg/g), DL-limonene (12.3 µg/g), and dill
ether (7.8 µg/g). α-Phellandrene also was the main compound of all the three studied fresh dill cultivars (Dura,
Dukat and Mammut) grown at Sahalahti of Finland in 1983
and 1984 using a modiied Soxhlet technique [35] and dill
leaves from Latvia using the solid phase micro-extraction
technique [1]. The proportion of α-phellandrene (58.93%)
was approximately at the identical concentration level
(57.10%) as detected earlier in microwave vacuum dried
dill stems [1], and much higher than the proportions of
19.12 and 14.68% revealed in aerial parts using the hydrodistillation [30] and fresh leaves by the ultrasound-assisted
extraction [36].
The relative extent of the α-phellandrene from the total
aroma content in the three diferent cultivars of the dill,
Dura, Dukat and Mammut, grown at two diverse regions
in Finland, Sahalahti and Viikki, was comparatively constant between 40–60% and 30–50%, respectively [35].
α-Phellandrene gives a typical dill lavor and also fragrant
and fresh notes [3]. As can be indicated in Fig. 1, the dill
aroma descriptor was also distinguished in the highest score
by the panel. Fresh dill aroma is composed of synergistic
communication contributed mainly by α-phellandrene with
an altering eicacy from dill ether [1]. Three fundamental
compounds, carvone, α-phellandrene, and limonene, have
been ascertained in the dill aroma, but their contents differed extensively, belonging to the diverse agents such
as the geographical origin, ripening degree and growth
situations.
Additionally, the extraction technique could also inluence the volatile oil amount and composition [35]. Dill
seed oil is distinguished by a high extent of carvone and
limonene [2–6], while the aerial part oil of the herb consists, in addition to carvone and limonene, remarkable values of α-phellandrene [9, 35]. Carvone reveals caraway-like
and cooling notes in the dill herb volatile oil [3]. According
13
A. Amanpour et al.
to the geographical origin, the content of carvone in
the herb volatile oil has been evidenced to difer from 6 to
44%, while its content in the dill seed volatile oil is more
constant at 40–55% [9]. The amount of the limonene as
another important terpene compound in dill leaves is more
than in its stems and it liberates lemon and mint aroma [1].
α-Pinene along with the α-thujene, β-pinene,
(+)-2-carene, (+)-4-carene, γ-terpinene, α-terpinolene,
α-ocimene, 1-octen-3-ol, (E)-sabinene hydrate, (Z)-sabinene hydrate, 4-terpineol, methylcarvacrol, (E)-caryophyllene, aromadendrene, α-caryophyllene, α-terpineol,
isoborneol, β-bisabolene, β-sesquiphellandrene, (Z)-γbisabolene, carvacrol acetate, ρ-cresol, eugenol, thymol
and carvacrol were detected in the savory as terpene compounds. Most of these were discovered in the savory from
various countries and species in earlier investigations
[6, 7, 11–16]. Generally, volatile oils have mainly a cytotoxic activity because of the presence of thymol, carvacrol, α-pinene and ρ-cymene compounds [36]. γ-Terpinene
(6236.83 µg/g) (59.13%) as indicated in Table 1 was the
most abundant compound in savory samples followed by
carvacrol (3239.19 µg/g) (30.71%), α-pinene (267.08 µg/g)
(2.53%), α-thujene (219.36 µg/g) (2.08%) and β-bisabolene
(130.8 µg/g) (1.24%).
The identical results were approximately evidenced in
an earlier research on air-dried aerial parts of savory from
the Maragheh region in the Northwest Iran using the hydro
distillation technique. Particularly, γ-terpinene (42.2%)
and carvacrol (31.9%) consisted of approximately 77% of
the distinguished compounds and were the most prevailing
compounds of the volatile oil [6]. Disagreements among
chemical combinations and amounts of various Satureja
species volatile oils were also indicated concerning the literature review. Carvacrol (40.8%) and γ-terpinene (26.4%)
in S. boissieri volatile oil from Turkey; pulegone (64.3%)
and menthone (20.2%) in S. brownie from Venezuela;
γ-terpinene, β-caryophyllene and germacrene D in S. boliviana and piperitone oxide in S. parvifolia from Argentina;
germacrene D in S. coerulea from Turkey and carvacrol
and γ-terpinene in S. hortensis from Iran were characterized as conquering compounds [7].
Considering the isolation technique in the volatile
oil of S. sahendica, thymol (37.2%), ρ-cymene (32.6%)
and γ-terpinene (11.5%) via the hydrodistillation technique and the similar compounds, but with various contents, thymol (66.0%), ρ-cymene (20.3%) and γ-terpinene
(3.6%) by steam distillation technique were detected as the
main compounds [11]. Additionally, α-pinene, β-pinene,
α-thujene and β-myrcene in the steam distilled volatile
oil was not observed [11]. In another study on Satureja
hortensis volatile oil, the outcomes demonstrated that
the hydrodistillation revealed the largest content of carvacrol (46.0%), while the steam distillation released the
13
lowest content of carvacrol (12.3%) and the highest content of γ-terpinene (70.4%) [13]. Carvacrol (52.2–62.0%),
thymol (8.6–11.0%), ρ-cymene (6.9–12.8%), γ-terpinene
(6.4–9.4%) and β-bisabolene (2.0–2.7%) were the principal compounds in Satureja montana using hydrodistillation. Supercritical luid extraction volatile oil contains of
the similar major compounds but with diverse contents as
carvacrol (41.7–64.5%), thymol (6.0–11.3%), ρ-cymene
(6.0–17.8%), γ-terpinene (2.3–6.0%) and β-bisabolene
(2.2–3.5%) [16].
According to the diferent parts of S. sahendica volatile
oil, thymol (31.5%), γ-terpinene (29.33%) and ρ-cymene
(23.48%) in the cluster volatile oil and ρ-cymene (44.88%),
thymol (28.22%) and γ-terpinene (10.07%) in the leaf
and stem volatile oil were shown as the principal compounds [37]. On the basis of diferent localities, thymol
(19.6–41.6%), ρ-cymene (32.5–54.9%) and γ-terpinene
(1–12.8%) were the major compounds in S. sahendica volatile oil from eight localities [7]. Based on the drying method
in S. hortensis volatile oil extracted by the hydrodistillation, carvacrol (46.0%), γ-terpinene (37.7%), ρ-cymene
(4.2%) and α-terpinene (3.1%) in shade-dried aerial parts,
carvacrol (46.8%), γ-terpinene (39.4%), ρ-cymene (4.4%)
and α-terpinene (3.3%) in sun-dried aerial parts and carvacrol (48.1%), γ-terpinene (38.4%), ρ-cymene (3.5%) and
α-terpinene (3.4%) in oven-dried aerial parts at 45 °C were
the major compounds [13]. The main compounds of Satureja horvatii volatile oil in accordance with the growing
regions were thymol (63.7%), γ-terpinene (7.5%), carvacrol methyl ether (4.9%), carvacrol (4.7%), and ρ-cymene
(4.5%) in Orjenske Lokve, Mt. Orjen, carvacrol (68.1%),
ρ-cymene (8.3%) and γ-terpinene (5.8%) in Mt. Lovcen
[15]. γ-Terpinene with the oily, woody, terpene lemon/lime,
tropical and herbal, and carvacrol with the spicy, woody,
camphor and thymol aroma characters were proved in Satureja myrtifolia aerial parts from the Lebanon origin [38].
Conclusion
The current investigation was allocated to deine the aroma
compounds in the shade-dried aerial parts of the Iranian dill
(A. graveolens L.) and savory (S. sahendica Bornm.) plants.
Fourty and twenty six aroma volatiles, in total, were speciied in the dill and savory, respectively, using the GC–MS
and GC–FID. The SAFE isolation technique gave highly
representative aromatic extract in both analyzed samples.
Dill with 271.52 µg/g aroma compounds consisted of
the terpenes (28), aldehydes (3), an alcohol (1), acids (3),
volatile phenols (3), a ketone (1) and norisoprenoid (1) and
savory with 10547.16 µg/g aroma compounds composed
of the terpenes (20), an alcohol (1) and volatile phenols
(5). From all aroma compounds found in both samples,
Aroma constituents of shade-dried aerial parts of Iranian dill (Anethum graveolens L.) and…
terpenes were quantitatively the most prevailing. Within
these compounds, α-phellandrene (160.0 µg/g) followed by
sabinene (26.5 µg/g), D-carvone (16.2 µg/g), DL-limonene
(12.3 µg/g) and dill ether (7.8 µg/g) in dill and γ-terpinene
(6236.83 µg/g) followed by carvacrol (3239.19 µg/g),
α-pinene (267.08 µg/g), α-thujene (219.36 µg/g) and
β-bisabolene (130.8 µg/g) in savory were quantitatively
demonstrated as the principal compounds.
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