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Artemisia spicigera Essential Oil: Assessment of Phytochemical and Antioxidant Properties


1 Department of Public Health, Qazvin University of Medical Sciences, Qazvin, IR Iran
2 Drug Applied Research Center, Tabriz University of Medical Sciences, Tabriz, IR Iran
*Corresponding author: Razzagh Mahmoudi, Department of Public Health, Qazvin University of Medical Sciences, Qazvin, IR Iran. Tel: +98-9127868571, E-mail: r.mahmodi@yahoo.com.
Biotechnology and Health Sciences. 2015 November; 2(4): e32605 , DOI: 10.17795/bhs-32605
Article Type: Research Article; Received: Aug 20, 2015; Revised: Sep 14, 2015; Accepted: Sep 26, 2015; epub: Nov 23, 2015; ppub: Nov 2015

Abstract


Background: Essential oils (EO), also called volatile odoriferous oil, are aromatic oily liquids extracted from different parts of plants. In general, the constituents in EOs are terpenes, aromatic compounds (aldehyde, alcohol, phenol, methoxy derivatives, and so on), and terpenoids (isoprenoids). Essential Oils have been known to possess antioxidant and antimicrobial activities, thereby serving as natural additives in foods and food products.

Objectives: The aim of this study was to assess the quantity and quality of compounds, with active chemical and antioxidant properties, of Artemisia spicigera essential oil (EO) due to the effect of geographic location and season of harvest on the phenolic compounds of the plant. The plant was collected from east Azarbayjan province, Iran (both before and after the flowering stage).

Materials and Methods: A. spicigera EO was analyzed by gas chromatogram/mass spectrometry (GC-MS). The antioxidant activity and total phenolic content before and after flowering were evaluated by the Folin Ciocalteu method. Also, the yields of essential oil as a percentage based on the level of dry plant and the volume of extracted oil was determined.

Results: Analysis of A. spicigera EO by gas chromatogram-mass spectrometry showed that spachulenol 1 H cycloprop (18.39%) and bicyclo hexan-3-en, 4-met (26.16%), were the prominent EOs of Artemisia before and after the flowering stage; the total phenolic EO before and after the flowering stage was 23.61 ± 1.08 µg/mL and 17.71 ± 0.9 µg/mL, respectively. Also level of flavonoid content before and after the flowering stage was 37.27 ± 1.70 µg/mL and 29.04 ± 1.30 µg/mL, respectively. This EO was able to reduce the stable free radical 2, 2-diphenol,1-picryl hydrazyl (DPPH) with an IC50 of 86.14 ± 2.23 and 96.18 ± 2.61 µg/mL, before and after flowering, respectively. Yield of EO before and after flowering was 0.5% and 0.6%, respectively.

Conclusions: Results have shown that A. spicigera EO before and after flowering has antioxidant properties and therefore can be used in combination with other preservatives to protect food materials against a variety of oxidative systems.

Keywords: Essential Oils; Antioxidants; Gas Chromatography; Artemisia spicigera

1. Background


In the recent years, it has been proved that free radicals are the most important oxidative factors in food products (that are induce changes in nutritional value and chemical compositions) (1, 2). In addition to the adverse effects on the organoleptic properties of food with destruction of vitamins and essential fatty acids, in the body, these toxic compounds can lead to adverse effects such as inflammatory diseases, diabetes mellitus, ischemic heart and brain disease, cancer, immune deficiency and aging (3, 4). Therefore, the use of antioxidants for reduction of the rate of oxidation in foods is necessary, which if used properly can increase the shelf life of food products. Plants contain phenolic compounds and other compounds that have antioxidant potential. Since the activity of antioxidant compounds and natural extracts have been identified by a variety of methods, it is currently important to determine which of these natural antioxidants have greater efficiency (5). Flavonoids and other phenolic compounds are available in many plants and act as antioxidant, anti-microbial and anti-inflammatory agents and vasodilators, as indicated by a number of previous studies (6). These compounds can generally be seen in fruits, vegetables, leaves, nuts, seeds, roots and other plant parts. Due to the various properties of these phenolic compounds, they have become a point of interest in the food, chemical, pharmaceutical and medical fields (7). The Artemisia plant genus is one of the most important plants in the pastures of Iran, which has many species and forms large areas of the country’s steppe and semi-steppe region’s natural covering. This genus has 34 species of medical plants, which are spread throughout the country. These species include A. melanolepis and A. kermanesis. Other species of the genus Artemisia, in addition to Iran, grow in the Caucasus, Siberia, Turkmenistan, Afghanistan, Pakistan, Central Asia, Tibet and Europe (8). Artemisia spicigera as a member of the Asteraceae family is a perpetual genus, which is frequent under circumstances of 300 mm annual rainfall. Artemisia is abundant in the north and northwest regions of Iran. In Iranian traditional medicine, Artemisia is known to have astringent, antiseptic, anti-parasitic and anti-poisoning properties (9). Several studies on the essential oil yields from other species of the genus Artemisia have been performed previously. Chemical analysis of Essential Oil (EO) has shown that cineol crysanton, alphapinen and micetilen form the major parts EO (10, 11). Chemical EOs are formed from poly-propanoids, mono and sesquiterpene oils and aromatic compounds (11).


Considering the importance of medicinal plants, especially native medicinal plants of our country and also considering the impact of geographic location and harvest season of the plant on active chemical compounds, the aim of this study was to evaluate the quantity and quality of phenolic compounds and antioxidant properties of EO of Artemisia before and after flowering. Furthermore, these EO were studied due to their richness in our country as well as their accessibility and affordability.

2. Objectives


The aim of this study was to determine the quantity and quality of active chemical compounds and antioxidant properties of A. spicigera EO collected from East Azerbaijan (before and after flowering).

3. Materials and Methods


3.1. Plant Material

Samples of A. spicigera were collected during year 2015 from Bostan-Abad of East Azerbaijan province (Iran) before and after flowering. The species of the collected plant was confirmed and deposited at the herbarium of the department of pharmacy, university of Tabriz, Iran.


3.2. Preparation of Essential Oil

The dried plants (100 g) were hydro-distilled for three hours using a Clevenger type apparatus. The essential oil was then dehydrated over anhydrous sodium sulfate and after passing through a filter with a pore size of 0.45 µm, it was stored in sealed vials at 4°C (12).


3.3. Determination of the Yield of Plant Essential Oil

The amounts of dried plant used in the experiment and the yield of essential oil before and after flowering (as a percentage) were determined.


3.4. Gas Chromatogram-Mass Spectrometry (GC/MS)

The EO was analyzed by a gas chromatogram. The chromatograph (Agilent 6890 UK) was equipped with an HP-5MS capillary column (30 × 0.25 mm ID × 0.25 mm film thickness) and the data were taken under the following conditions: initial temperature of 50°C, temperature ramp of 5°C/minute, 240°C/minute to 300°C (holding for three minutes), and injector temperature at 290°C. The carrier gas was helium and the split ratio was 0.8 mL-1/minute. For confirmation of analysis results, the essential oil was also analyzed by GC/MS (Agilent 6890 gas chromatogram equipped with an Agilent 5973 mass-selective detector; Agilent UK) and the same capillary column and analytical conditions as above. The MS was run with the electron-ionization mode and ionization energy of 70 eV (13, 14).


3.5. Assay for Total Phenolic Content

Measurement of total phenolic materials was carried out using Folin-Ciocalteu reagent (Sigma-Aldrich) and gallic acid (Sigma-Aldrich) as the standard (15). Furthermore, 0.1 mL of the mentioned EO was transferred to an Erlenmeyer flask followed by the addition of 46 ml of distilled water and 1 mL of Folin-Ciocalteu reagent and the content was severely mixed. After three minutes, 3 mL of 2% sodium carbonate was added and the mixture was placed on an agitator screen with medium intensity for two hours and its absorption was read at 760 nm. This stages accomplished for standard soloution of gallic acid (0 - 1000 µg per 0.1 mL) and will be drowsed a standard curve equation according to the following equal (16).


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3.6. Flavonoid Contents

In order to measure the content of the flavonoids, different concentrations of EO were prepared and 0.5 mL of each concentration was poured into a test tube and to each tube 500 µL of 2% aluminum chloride was added and the tubes were left at room temperature for one hour and the absorbance was measured at 420 nm by a spectrophotometer apparatus. Using this method a standard curve of quercetin was drawn with a range of 5 to 60 mg and the total flavonoid content was calculated based on milligrams of quercetin per gram of essential oil (17).


3.7. Determination of Antioxidant Activity (DPPH Assay)

Power of dehydroghenation of extracted is measured by decolourization of solution of diphenyl Picryl hydrazyl. In this spectrometry evaluation, stable radical diphenyl Picryl hydrazyl (Sigma-Alderich) was used as the reactant. Fifty milliliters of different concentrations of essential oil was added to 5 mL of methanolic solution (0.004%). After 30 minutes at room temperature, absorption at a wavelength of 517 nm was read and compared with the control. The inhibition free radical DPPH based on percentage (I%) was calculated as follows:


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Where A was the blank (containing all reactants except EO) and A ample was the absorption solution containing different concentrations of EOs. The concentration of essential oil that showed 50% inhibition (IC50) was given based on the percentage of inhibition against the concentration of essential oil, respectively. Synthetic antioxidant Boutill hydroxyl anysol (BHT) was used as the positive control. The tests were performed in triplicates (18, 19).

4. Results


4.1. The Yields of Essential Oil

The oil was isolated by hydro distillation from the dried plant before and after flowering. The yield of the EO before flowering was 0.5% (v/w) and after flowering this was 0.6% (v/w).


4.2. Constituents of Artemisia spicigera Essential Oil (Before and After Flowering) Using GC/MS

The evaluation of the results of this study showed that the yield of EO of A. spicigera before and after flowering was 0.5% and 0.6% based on the dry weight of the plant, respectively. The major compound of EO before and after flowering, along with retention time and the percentage of each compound are shown in Tables 1 and 2. Before flowering 33 compounds were detected that made up 94.32% of EOs, and the most common components were (-) -1H spachoulenol cycloprob (18.39%), epizunaren (9.64%), germakerin D (6.33%) and trans-caryophyllene (6.17%). Also after flowering, 13 compounds were identified that in to form 96.23% of components of EO. Most of the components of the EO after flowering formed bicycle [3, 1, 0] Hexan-3-en, 4 - met (26.16%), 1, 8 cineole 2-oxabicyclo [2, 2…] (26.15%), camphor bicyclo [2, 2, 1] heptane (17.46%) and beta tougun (12.86%).


Table 1.
Constituents of Artemisia spicigera Essential Oil (Before Flowering) Identified Using Gas Chromatogram/Mass Spectrometrya

Table 2.
Constituents of Artemisia spicigera Essential Oils After Flowering Using Gas Chromatogram/Mass Spectrometrya

4.3. Total Phenolic and Flavonoid Contents

Content of total phenol of EO in the stages of before and after was 23.61 ± 1.08 and 17.71 ± 0.9 micrograms gallic acid on milliliter EO.


Content of total flavonoeid of EO in the stages of before and after was 37.27 ± 1.7 and 29.04 ± 1.3 micrograms Quercetin on milliliter EO.


4.4. 2, 2-Diphenyl, 1-Picryl Hydrazyl (DPPH) Assay

Antioxidant activity was determined using the DPPH method. The level of IC50 for EO before flowering was 86.14 ± 2.23 (87.57 to 105.5) micrograms per milliliter and after flowering this was 96.18 ± 2.61, both of which were weaker than Butylated Hydroxytoluene (BHT) (Table 3). The results showed that with increasing concentrations of EO inhibition free radicals to be increased.


Table 3.
IC50of Essential Oil and Controlsa

5. Discussion


The results of the investigation of the chemical compounds of A. spicigera EO in the present study were somewhat in accordance with other investigations. In most studies similar to the present study, compounds such as 1H spachoulenol cycloprob (18.39%), epizunaren (9.64%), germakerin D (6.33%) and trans-caryophyllene (6.17%), respectively, were the major components of the A. spicigera EO before flowering. Also, bicyclo [3, 1, 0] hexan-3-en, 4-met (26.16%), 1, 8 cineole 2-oxabicyclo (26.15%), camphor bicyclo heptane (17.46%) and beta tougun (12.86%) after flowering were the major components of EO. In this study, 33 compounds were detected before flowering, including 94.3% EO while 13 compounds were detected after flowering including 96.23% EO. The yield of the EO before flowering was 0.5% (v/w) while after flowering this was 0.6% (v/w).


The level of phenolic compounds of A. spicigera EO before and after flowering was 23.61 ± 1.08and 17.71 ± 0.9 mg of gallic acid per gram of EO, respectively. Also the levels of flavonoeid compounds of EO before and after flowering, were 37.27 ± 1.70 and 29.04 ± 1.30 µg per mL, respectively. Level of IC50 of A. spicigera EO before flowering was 86.14 ± 2.23 µg per mL and after flowering this was 96.18 ± 2.61 µg per mL.


Currently, researchers are interested to study medicinal plants for extraction of natural antioxidants for usage instead of synthetic antioxidants. Natural antioxidants are healthier, have greater benefits and fewer side effects (20).


Among natural food additives that can be used in many foods, EOs are a good option with a plant origin that have antibacterial, antifungal, antioxidant, and anti carcinogenic properties (21).


In one study it was reported that free radical scavenging increases with increasing EO concentration and the obtained extract from the aerial parts of Artemisia, collected from regions of the Alborz Golestanak, provide 50% inhibition (IC50 of 30.6 ± 612 μg/mL) (22). In another study, the level of IC50 of the methanol extract from the aerial parts of Artemisia, collected from different areas of East Azarbaijan, was 29.74 to 64 .18 µg per mL (23). In another report, the level of inhibition of the free radical form of 2, 2 diphenyl 1-picrylhydrazyl of Artemisia, collected from Babak city of Kerman, was 71.6 ± 1.7 µg per mL (24).


According to the study of Mahmoudi, the level of total phenol of aerial parts of Artemisia, collected from different areas of Golestanak, was 194.7 ± 9.9 mg of gallic acid per gram of extract (22).


In the study of Khalaji et al. the level of phenol of the methanol extract of aerial parts of Artemisia, collected from different regions of East Azerbaijan, was 1.4 to 2.3 µg per 100 µg extract (23). In the mentioned study, the level of total flavonoid of the methanol extract of the aerial parts of Artemisia, collected from areas of Golestanak Alborz, was 0.6 ± 12.4 mg quercetin per gram of extract (22).


Also in the study of Khalaji and et al. the level of flavonoids of methanol extract of aerial parts of Artemisia, collected from different regions of East Azerbaijan, was 0.4 to 2.1 µM quercetin per 100 gram extract (23).


In year 2011 a study showed that aqueous extracts of the genus of Artemisia afra Jacq reduced Maloven-di-aldeid (MDA) and increased Super Oxide Dismotaz (SOD), glutathione reductase and glutathione peroxidase as enzymatic antioxidants in diabetic experimental animals (25).


The study conducted on aqueous extracts of Artemisia sieberi vulgaris in Egypt showed that IC50 was equal to 10 µg per mL. Level of Phenol aqueous extract of Artemisia sieberi vulgaris was 7.96 ± 0.76 mg gallic acid per gram of extract. The level of its flavonoid was 3.4 mg rutin per gram of extracts (26).


The conducted study on ethanol extract of Artemisia seeds in Nigeria showed that the level of IC50 was 150.33 ± 1.5 µg per mL (27).


The difference observed in the antioxidant properties of medicinal plants in various studies can be due to differences in the compounds of the mentioned plant (under the effect of genetics, water, air, harvest season, etc.), especially in the amount of phenolic and polyphenol compounds, so that there was a direct correlation between the level of phenol and antioxidant activity of medicinal plants (15).


Considering that Artemisia is native in Iran, and has easy and cheap access, consumption of this plant (a source of phenolic compounds) as an antioxidant in food and pharmaceutical industries, is favorable.

Acknowledgments

This study was part of a thesis in Master of Science in health and food safety approved by the university of medical sciences of Qazvin and thereby it is necessary thank the research council of the university of medical sciences of Qazvin for approval and funding of this projects. Finally, we appreciate the laboratory of food chemistry, faculty of veterinary medicine, and university of Tabriz.

Footnotes

Authors’ Contribution: Peyman Ghajarbeygi, Azar Mohammadi, Razzagh Mahmoudi and Morteza Kosari-Nasab developed the original idea and the protocol, abstracted and analyzed the data, wrote the manuscript, and were the guarantors.
Funding/Support: This study was supported by the Qazvin University of Medical Sciences, Qazvin, Iran.

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Table 1.

Constituents of Artemisia spicigera Essential Oil (Before Flowering) Identified Using Gas Chromatogram/Mass Spectrometrya

Compound No. Compound Name RT, min Percentage
1 Bicyclo [3.1.1] hept-3-en-2-ol, 4,.. 8.6 6.76
2 p-Mentha-1, 5-dien-8-ol 2, 4-Cy... 9.02 3.76
3 Bicyclo [3.1.1] hept-2-ene-2-metha... 9.61 3.34
4 Bicyclo [3.1.1] hept-3-en-2-one, 4... 9.96 1.57
5 Trans-(+)-carveol 10.11 1.24
6 Acetic acid, 1, 7, 7-trimethyl-bic... 11.5 1.28
7 BetaETA. Bourbonene 13.4 1.42
8 Trans-Caryophyllene Bicyclo [7... 14.26 6.17
9 Trans-.beta.-Farnesene (E)-.b... 14.82 1.6
10 Alpha-Caryophyllene 14.9 1.41
11 1 Germacrene-D 15.65 6.33
12 Bicyclogermacrene [8.1... 15.94 2.91
13 1H-Cycloprop[e]azulene, 1a, 2, 3, 4... 16.32 1.46
14 Beta.-cadinene 16.39 1.05
15 Delta.-Cadinene Naphthalene,... 16.46 1.75
16 Butyl hydroxy toluene 16.68 1.06
17 Alpha-agarofuran 17 1.41
18 Caryophyllene oxide 5-Oxatric... 17.13 1.8
19 Germacrene B (CAS) 1, 5-Cyclod... 17.22 1.03
20 (-)-Spathulenol 1H-Cycloprop [... 18.08 18.39
21 Salvial-4(14)-en-1-one 18.18 1.14
22 Vieridiflorol Viridiflorol... 18.31 1
23 Caryophyllene oxide 18.44 2.05
24 2- Naphthalenemethanol, 1, 2, 3, 4, 4... 18.64 3.02
25 1H-Cycloprop [e] azulene, 1a, 2, 3, 4... 18.76 1.17
26 Junipiene 1,4-Methanoazulene, ... 18.95 1.7
27 Naphthalene, 1, 2, 3, 5, 6, 7, 8, 8a-oc... 19.02 1.16
28 Epizonaren 19.37 9.62
29 7-Epi-.alpha.-selinene 19.46 3.49
30 Caryophylleneol-II Bicyclo [7.2... 19.6 1.74
31 Aromadendrene, dehydro- 19.71 1.26
32 12-Norcyercene-B 19.83 1
33 2-Pentadecanone, 6,10,14-trimethyl- 22.27 1.23
Total 94.32
a This table includes basic compounds that had the highest percentage and minor compounds were avoided.

Table 2.

Constituents of Artemisia spicigera Essential Oils After Flowering Using Gas Chromatogram/Mass Spectrometrya

Compound No. Compound Name RT, min Percentage
1 Camphene Bicyclo [2.2.1] heptan... 4.85 2.3
2 1, 8-Cineole 2-Oxabicyclo [2.2.... 13.09 26.15
3 Bicyclo [3.1.0] hexan-3-one, 4-met... 15.65 26.16
4 Beta-thujone 7.96 12.86
5 Camphor Bicyclo [2.2.1] heptan-... 8.47 17.46
6 Trans-decalin, 2-methyl- 8.54 1.48
7 Pinocarvone 6, 6-dimethyl-2-me... 8.63 1.6
8 Endo-Borneol Bicyclo [2.2.1] he... 8.71 2.39
9 Bicyclo [2.2.1] heptan-2-one, 1, 7,... 8.87 2.79
10 Benzenemethanol (CAS) Benzyl ... 9.24 1.54
11 Chrysanthenyl acetate 10.56 1.19
12 Bicyclo [2.2.1] heptan-2-ol, 1, 7, 7... 11.12 1.35
13 Phenol, 5-methyl-2-(1-methylethy... 11.17 0.96
Total 96.23
a This table includes basic compounds that had the highest percentage and minor compounds were avoided.

Table 3.

IC50of Essential Oil and Controlsa

Essential Oil IC50, µg/mL
A. spicigera (before flowering) 86.14 ± 2.23
A. spicigera (after flowering) 96.18 ± 2.61
Vitamin C 2.15 ± 0.23
a The results (means ± SD) are significantly different (P < 0.05).

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