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Low temperature extraction of essential oil bearing plants by liquefied gases. 7. Seeds from cardamom (Elettaria cardamomum /L./ Maton)

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Abstract

The chemical composition of extract from the seeds of cardamom (Elettaria cardamomum (L.) Maton, obtained by extraction with tetrafluoroethane was analyzed using GC and GC/MS. The major compounds (concentration higher than 3%) of extract were: terpinyl acetate (36.8%), 1,8-cineole (29.2%), linalyl acetate (5.2%), sabinene (3.9%) and linalool (3.1%). The studied extract demonstrated antimicrobial activity against pathogenic species Staphylococcus aureus, S. epidermidis, Salmonella abony and was inactive against Pseudomonas aeruginosa. The extract possessed low antioxidant activity against DPPH radicals.
ISSN: 1314-6246 Gochev et al. J. BioSci. Biotech. 2012, 1(2): 135-139.
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135
Velizar Gochev 1
Tanya Girova 1
Ivanka Stoilova 2
Teodora Atanasova 3
Neno Nenov 4
Veselin Stanchev 5
Albena Soyanova 3
Low temperature extraction of essential oil
bearing plants by liquefied gases. 7. Seeds from
cardamom (Elettaria cardamomum (L.) Maton)
Authors’ addresses:
1 Department of Biochemistry and
Microbiology, Faculty of Biology,
Plovdiv University, Plovdiv, Bulgaria.
2 Department of Biotechnology
3 Department of Essential Oils
4 Department of Heating Technology
5 Department of Automatic, informatics
and managing engineering,
University of Food Technologies,
Plovdiv, Bulgaria.
Correspondence:
Velizar Gochev
Faculty of Biology,
Plovdiv University
24, Tsar Assen Str.
4000 Plovdiv, Bulgaria
Tel.: +359 32 261493
e-mail: vgochev@uni-plovdiv.bg
Article info:
Received: 9 August 2012
In revised form: 2 September 2012
Accepted: 3 September 2012
ABSTRACT
The chemical composition of extract from the seeds of cardamom (Elettaria
cardamomum (L.) Maton, obtained by extraction with tetrafluoroethane was
analyzed using GC and GC/MS. The major compounds (concentration higher
than 3%) of extract were: terpinyl acetate (36.8%), 1,8-cineole (29.2%), linalyl
acetate (5.2%), sabinene (3.9%) and linalool (3.1%). The studied extract
demonstrated antimicrobial activity against pathogenic species Staphylococcus
aureus, S. epidermidis, Salmonella abony and was inactive against Pseudomonas
aeruginosa. The extract possessed low antioxidant activity against DPPH
radicals.
Key words: antimicrobial activity, antioxidant activity, cardamom, extraction
with tetrafluoroethane
Introduction
Cardamom is produced from cultivated or wild plants in
the mountainous regions of southern India, Sri Lanka,
Indonesia, and Guatemala. It has been used in the traditional
Chinese medicine and Indian Ayurvedic medicine for
thousands of years, mainly for treating respiratory diseases,
fevers and digestive complaints.
The cardamom essential oil is obtained by steam
distillation from the ripe and dried seeds of the tropical grass
Elettaria cardamomum (L.) Matori (Zingiberaceae). It is a
colorless or very pale yellow liquid with an aromatic,
penetrating, slightly camphoraceous odor and a persistent,
pungent, strongly aromatic taste. The physico-chemical
properties (ISO 4733:1981) were: relative density at 20/20°C:
0.191 - 0.936; refractive index at 20°C: 1.4620 - 1.4680;
optical rotation at 20°C: range from +22 to +41; solubility: 1
vol. in max. 5 vol. 70% ethanol (Bauer et al., 1997; Georgiev
& Stoyanova, 2006).
The major components of the cardamom oil are 1,8-
cineole (21-41%) and
-terpinyl acetate (21-35%). The
cardamom oil also contains the following components:
-
terpineol (0.8-6.2%, and to 11.5% in oil from Pakistan),
limonene (1.7-3.7%), sabinene+
-pinene (0.3-2.4%), borneol
(0.1-1.2%), linalool (0.4-8.7%), linalyl acetate (1.6-2.4%),
nerol (0.6-1.6%), geraniol (1.1-3.7%), neryl acetate (0.8-
1.2%), farnesol (up to 12.5% from the total isomers),
nerolidol (0.2-6.7%), isosafrole (3.8%) and other minor
compounds. Trace constituents like unsaturated aliphatic
aldehydes and
-terpinyl acetate may be important for the
ISSN: 1314-6246 Gochev et al. J. BioSci. Biotech. 2012, 1(2): 135-139.
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136
typical aroma of the oil (Bauer et al., 1997; Laurence, 2004;
Georgiev & Stoyanova, 2006).
The oil possesses antioxidant activity (Misharina et al.,
2009). It is used primarily for seasoning foods, alcoholic
beverages, the applied doses in foods varied from 0.20 to
0.50 mg %, and the minimal notable doses varied in the range
0.04 - 0.05 mg % (Bauer et al., 1997; Georgiev & Stoyanova,
2006). In small dosages, the oil is also used in perfumery and
cosmetics. For example, cardamom oil is a constituent of
mouthwash to treat bad breath and in creams, because the oil
has diuretic properties and may alleviate fluid retention and
cellulite (Rose, 2002; Georgiev & Stoyanova, 2006).
Cardamom oil is mainly used in aromatherapy as a
digestive remedy to alleviate flatulence, heartburn, nausea,
indigestion and colic. It acts as a general tonic for the
digestive system and speeds up sluggish digestion. In India,
cardamom oil is believed to have aphrodisiac qualities and is
used to reduce the feelings of stress and tension that may be
inhibiting sexual fulfillment. Its restorative properties make it
effective in treating physical and mental fatigue (Rose, 2002;
Georgiev & Stoyanova, 2006).
Different extracts are produced from cardamom seeds by
using various solvents such as diethyl ether (Ağaoğlu et al.,
2005; Syed Abdul Rahman et al., 2010), water (Suneetha &
Krishnakantha, 2005), ethanol (Nanasombat &
Lohasupthawee, 2005) and methanol (El-Segaey et al., 2007).
Chemical compositions and antimicrobial properties of the
extracts depend mainly on the type of the used solvent. The
cardamom fruits can also be extracted with liquefied gases by
supercritical carbon dioxide (Hamdan et al., 2008;
Gopalakrishnan 1994; Marongui et al., 2004) and sub-critical
propane (Hamdan et al., 2008) extractions. Propane was
found to be more capable than carbon dioxide to recover seed
oil at sub-critical condition with lower ratio of solvent/solid
and better quality attributes (Hamdan et. al., 2008). The
major constituents of both extracts were 1,8-cineole and
-
terpinyl acetate and the content of these compounds in the
final extract depend on the extraction conditions such as
temperature, working pressure and solvent.
Currently C2H2F4 (1,1,1,2-tetrafluorethane) is prospective
liquefied gas, which is licensed for producing of extracts for
application in food and flavour industry. Unfortunately there
are no publications for its application for extraction of
cardamom seeds.
The aim of present study was to produce cardamom
extract by 1,1,1,2-tetrafluorethane and to characterize the
obtained product according to its chemical composition,
antimicrobial and antioxidant properties.
Materials and Methods
Plant material
Cardamom seeds (Elettaria cardamomum (L.) Maton)
were obtained from trade market, origin Guatemala harvest
2009, humidity 8% (Russian Pharmacopoeia, 1990).
Obtaining of extract
The air-seeds of cardamom were ground separately in an
attrition mill to a size of 0.15-0.25 mm and the extract
obtained by a 1 dm3 volume C2H2F4 (1,1,1,2-tetrafluorethane)
laboratory-extractor (Nenov, 2006) under following
conditions (continuous flow and evaporation of solvent):
pressure 0.5 MPa; temperature 18-20oС and extraction time
60 min. The physico-chemical properties were measured
according to Russian Pharmacopoeia (1990).
Determination of chemical composition
GC analysis was performed using an Agilent 7890A gas
chromatograph equipped with FID detector and HP-
INNOWAX Polyethylene Glycol column (60 mm x 0.25
mm; film thickness 0.25 m); temperature: 70°C - 10 min,
70-240°C - 5°C/min, 240°C - 5 min; 240-250°C - 10°C/min,
250°C - 15 min; carrier gas helium, 1 ml/min constant flow;
injector split, 250°C, split ratio 50:1.
Gas Chromatography-Mass Spectrometry Analysis:
GC/MS analysis was carried out on an Agilent 5975C gas
chromatograph, carrier gas helium, column and temperature
as for GC analysis, FID 280°C, MSD 280°C, transfer line.
Determination of antimicrobial activity
Antimicrobial activity of the cardamom extract was
determined against pathogenic and spoilage bacteria from
clinical and food isolates and also against reference microbial
strains. The used test microorganisms and their origins are
listed in Table 2. The strains are deposited in the Microbial
Culture Collection at the Department of Biochemistry and
Microbiology”, Plovdiv University, Bulgaria. Minimal
Inhibitory Concentration (MIC) and Minimal Bactericidal
Concentration (MBC) of cardamom extract were determined
by serial broth dilution method in accordance with CLSI
reference method (CLSI Standards, 1990) A stock solution to
be tested was prepared by diluting the respective cardamom
extract sample in DMSO (Sigma-Aldrich Co.). Antimicrobial
activity of the extract was determined in concentrations
ranging from 0.00025 to 1.6% (w/v).
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137
Scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH)
radical
The radical scavenging capacity was determined
according to the method described by Mensor et al. (2001).
1.0 ml from 0.3 mM alcohol solution of DDPH was added to
2.5 ml from the samples with different concentration of
cardamom extract. The samples were kept at room
temperature in dark and after 30 min the optical density was
measured at 518 nm. The optical density of the working
samples, the positive controls and the blank samples were
measured in comparison with ethanol. The IC50 value
represented the concentration of the compounds that caused
50% inhibition of radical formation.
All experiments were done in triplicate and the results
were statistically evaluated using a level of confidence
γ=0.95.
Results and Discussion
The obtained extract is yellow mobile liquid with strong
characteristic for the plant material odour and taste. The yield
of cardamom extract is 2.7-3.0% (v/w).
Physicochemical properties were as follows: dry
substance (105°C): 9.70%, refractive index (20°C): 1.4647,
specific gravity (20°C): 0.9430, acid number: 3.6.
The chemical composition of the extract is presented in
Table 1. Twenty-seven components representing 94.5% of
the total content were identified. Ten of them were in
concentrations over 1% and the rest 17 constituents were in
concentrations under 1%. The major constituents (over 3%)
were terpinyl acetate (36.8%), 1,8-cineole (29.2%), linalyl
acetate (5.2%), sabinene (3.9%) and linalool (3.1%).
Results from the tests for antimicrobial activity are
presented in Table 2.
Antioxidant activity of the cardamom extract is presented
in Figure 1. As seen from the figure, 55.2% inhibition of
DPPH radical was reached at concentration 100 mg/ml and
the IC50 value was 63.3 mg/ml (correlation coefficient
R2=0.995).
According to physicochemical properties, the produced
cardamom extract is almost equal to the cardamom essential
oil. 90.7% of the identified substances in the extract belong to
the group of monoterpenes, followed by phenyl propanoides
(2.2%), sesquiterpenes (1.5%) and others compounds (0.1%).
Oxygenated monoterpenes (80.0%) are the major group.
According to the content of major constituents, the
produced freon extract of cardamom seeds is similar to the
published in the literature (Hamdan et al., 2008). The
qualitative differences in the rest of the constituents are due
to the type of the used solvent and the process parameters.
Table 1. Chemical composition of the cardamom extract.
Components
%
RI
MONOTERPENES
Hydrocarbons
Sabinene
3.9
973
d-Limonene
2.3
1026
Мyrcene
1.9
990
-Pinene
1.9
939
-Pinene
0.4
981
-Terpinene
0.3
1059
Oxygenated monoterpenes
Terpinyl acetate
36.8
1340
1,8-Cineole
29.2
1032
Linalyl acetate
5.2
1254
Linalool
3.1
1093
-Terpineol
1.6
1167
Geraniol
0.9
1240
Geranial
0.8
1225
Terpinen-4-ol
0.6
1182
Sabinene hydrate
0.3
1054
Fenchone
0.6
1090
Neral
0.3
1253
Geranyl acetate
0.3
1378
Carvyl acetate
0.2
1362
Terpinyl propionate
0.1
1430
SESQUITERPENES
Hydrocarbons
-Selinene
0.3
1458
-Cadinene
0.2
1522
Germacrene
0.1
1468
Oxygenated sesquiterpenes
Nerolidole
0.9
1534
PHENYL PROPANOIDS
Anethole
2.1
1269
p-Cymene
0.1
1020
OTHERS
Decenal
0.1
1260
The cardamom extract demonstrated antimicrobial
activity against Gram-positive and Gram-negative bacteria,
belonging to species S. epidermidis, S. aureus, E. coli and S.
abony. The extract was inactive against both strains of P.
aeruginosa, which belong to the group of the most resistible
bacterial strains. The ability of P. aeruginosa to produce
extracellular polysaccharides increased antimicrobial
resistance of these bacteria mainly through permeability
barrier.
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Table 2. Аntimicrobial activity of extract from cardamom..
Test microorganisms
Origin
MIC, % (v/v)
MBC, % (v/v)
1
Staphylococcus epidermidis
Clinical isolate
0.4
0.8
2
Staphylococcus aureus
ATCC 6538
0.4
0.8
3
Escherichia coli
Food isolate
0.8
0.8
4
Escherichia coli
ATCC 8739
0.8
0.8
5
Salmonella abony
Clinical isolate
0.8
0.8
6
Salmonella abony
ATCC 6017
0.8
0.8
7
Pseudomonas aeruginosa
Food isolate
inactive
8
Pseudomonas aeruginosa
ATCC 9627
inactive
These strains also produced two types of soluble pigments,
pyoverdin and pyocyanin, which probably participate in cell
defense against antimicrobials.
Figure 1. Antiradical activity of cardamom extract against
DPPH.
In comparison with strong antioxidants such as ascorbic
acid (4.20 g/cm3), rutin (14.65 g/cm3), BHT (1.12 g/cm3)
and BHA (4.41 g/cm3), which are traditionally used in
cosmetics and food industry, the produced cardamom extract
possesses considerably lower antioxidant activity. In
comparison with other extracts produced by low temperature
extraction with 1,1,1,2-tetrafluorethane from anise fruirts
(IC50=8.32 mg/ml Atanasova, 2007), coriander fruits
(IC50=17.74 mg/ml Atanasova et al., 2010) and cinnamon
barks (IC50=0.38 mg/ml Nenov et al., 2011), the cardamom
extract also demonstrates lower antioxidant activity.
Conclusion
The extract from cardamom (Elettaria cardamomum (L.)
Maton) seeds produced by low temperature extraction with
tetrafluoroethane characterized with higher content of
terpinyl acetate (36.8%), 1,8-cineole (29.2%), linalyl acetate
(5.2%), sabinene (3.9%) and linalool (3.1%) with
characteristic odour and taste. The produced extract
demonstrated antimicrobial activity against some of the most
widely spread pathogenic and spoilage bacteria in foods and
characterized with low antioxidant activity in comparison
with other extracts produced by low temperature extraction.
Currently, the experiments for application of the produced
cardamom extract in cosmetic and food products are in
progress.
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... E. cardamomum EO is used mainly for treating fevers, digestive complaints, and respiratory diseases (Gochev et al., 2012); it embraces aromatic compounds with stimulant, astringent, diuretic, carminative, anti-inflammatory, and antioxidant activities (Asghar et al., 2017). These pharmaceutical activities have been attributed to the presence of oxygenated monoterpenes (1,8-cineole, α-terpinyl acetate, and geraniol) and phenyl propanoids (eugenol) (Das et al., 2012;Tangjitjaroenkun et al., 2020). ...
... Each of the remaining identified compounds constituted less than 1% of the oil yield. The dominance of oxygenated monoterpenes with α-terpinyl acetate, linalool, and 1,8-cineole as the dominant constituents was reported previously in different literature (Singh et al., 2008;Gochev et al., 2012). However, some studies had reported relatively lower proportions of α-terpinyl acetate, linalool with higher percentages of 1,8-cineole in EO of cardamom from several countries, 25.6%-26.71% of 1,8-cineole (Snoussi et al., 2015;Asghar et al., 2017). ...
... The herein reported antibacterial and antioxidant activities of E. cardamomum EO could be attributed to the presence of high content of oxygenated monoterpenes, mainly 1,8-cineole, α-terpinyl acetate (Das et al., 2012;Elguindy et al., 2016;Tangjitjaroenkun et al., 2020). Its EO was reported to inhibit the growth of Gram-positive and negative bacteria with MIC (0.4-0.8%, v/v) (Gochev et al., 2012). Remarkably, the anti-S. ...
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... This absence and the presence of various compounds such as α-terpinene, 1-phellandrene, isopinocarveol, 4-terpineol, δ-3-carene, trans-sabinene hydrate, 1-terpineol, bicyclogermacrene, longifolenaldehyde tertracosane, ledenoxid-II and αterpenyl acetate contributed to the distinct aroma of the essential oils of large cardamom from Himachal Pradesh. Gochev et al. (2012) analysed α-terpinyl acetate, 1, 8-cineole and 1, 8cineole as the main constituents of the essential oils of E. cardamomum from Turkey. Winarsi et al. (2012) stated that the plant parts of E.cardamomum contained bioactive compounds. ...
... The major flavouring compound present in the essential oil of cardamom is d-limonene, 1,8-cineole, geraniol, terpineol, citronellal, a-terpineol, and α-terpinyl acetate, 4-terpineol whereas the volatile fraction consisted mainly of d-limonene and 1,8-cineole. The minor constituents were β-myrcene, pinene and terpinolene, (Gochev et al., 2012;Joshi et al., 2013). Savan and Kucukbay (2013) analysed the volatile oils in the seeds of E. cardamomum from south India and detected the presence of α-terpinyl acetate, 1,8-cineole, limonene and α-terpineol. ...
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Cardamom is one of the most expensive species in the world which belongs to the family Zingiberaceae and it's used as traditional medicine. Cardamom is cultivated in India, Sri Lanka, Tanzania and Guatemala. It's available in two types; black cardamom (Amomum subulatum) and green cardamom (Elettaria cardamomum). In folk medicine, different parts of E. cardamomum is used in the treatment of gastrointestinal disorders, stomachic, retentive, digestive, antiemetic, carminative and anti-putrefactive (during embalmment) agents, and also in treating gums, teeth and throat infection, lung congestion, pulmonary tuberculosis, high blood pressure, heart disease and digestive disorders. Cardamom oil is used as a spice in food and as liquors/flavours in pharmaceutical industries. In medicine, its oil is used as a powerful antiseptic, stomachic, aromatic and diuretic agent. The capsules have been used traditionally for teeth, gum infections, asthma and preparations of digestive ailments. In this chapter, we have consolidated the phytochemical and pharmacological properties of cardamom and their medicinal uses and the antioxidant activities present in cardamom along with its popular and traditional uses.
... ta.bg) and ground to a size of 0.3-0.5 mm. Clove extract was obtained by low temperature extraction with liquefied gas according to Gochev et al. (2012) with modification related to the volume of the extractor which in the indicated work was 10 dm 3 . As a solvent, 1,1,1,2-tetrafluoroethane (Merck Bulgaria EAD, Sofia, Bulgaria) was used (Corr 2002). ...
... However, before going to conclusions related to practical aspects, tests on larger For elucidating the antimicrobial activity of plant extracts, a significant part of the research is devoted to identification of the active constituents in the extracts. For example, in clove oil and extract the monoterpene eugenol has been identified as the main compound and its bactericidal activity assumed to depend on its amount (Gochev et al. 2012;Goñi et al. 2009;Guan et al. 2007;Ivanovic et al. 2013;Chudasama and Thaker 2014). As compared to oregano and monarda oils, in our hands clove extract showed a medium level of inhibition of all bacterial strains (Figs. 1 and 2a). ...
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... The concentrations of these compounds varied among different cardamom accessions, with distinct accessions exhibiting higher levels of sabinene (4.9%), β-linalool (11.0%), α-terpineol (13.2%), and nerol (1.1%) as reported by Ashokkumar et al. (2021). In their study, Gochev et al. (2012) documented that essential oil primarily treats fevers, digestive concerns, harvest timing, and extraction methods, influence essential oils' chemical composition and subsequent biological activity. The present study assessment of essential oil and its constituents revealed that the quality of cardamom essential oil is significantly influenced by various factors such as climatic conditions, extraction methods, storage, soil characteristics, maturity, harvest timing, and genotypic factors. ...
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... Previous studies have reported MIC of cardamom EO at 0.4% against S. aureus ATCC 6538 and 0.8% against E. coli ATCC 8739 (Gochev et al., 2012). However, in the present study we tested the EOs against multi drug resistant pathogens that is why higher MIC values were achieved as compare to previous reports. ...
... In addition to α-terpinyl acetate, other terpenoids such as α-terpineol, linalool, linalyl acetate, and geraniol impart a sweet flavour that counterbalances the camphorated-sharp touch of 1,8-cineol. The chemical composition of small cardamom seeds essential oil extracted by HD in this study was found to be in good accordance with previous studies in which the 1,8-cineol and αterpinyl acetate were the major components [24][25]. ...
... It also has a high volatility and a boiling point (26.2°C) at atmospheric pressure, which means that it is a negligible solvent residue in the products. Due to the flexible selectivity of the solvent, the resulting products can be high quality analogs of essential oils (Gochev et al., 2012;Nenov et al., 2011), food or bio-pharmaceuticals substances (Babu et al., 2014;Han et al., 2012;Lapkin e. al., 2014;Setapar et al., 2014). Wilde & McClory (1994) and Wilde (1996) mention the application of this method to Rosa damascena, but there is a lack of details of the extract. ...
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