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 Table of Contents  
ORIGINAL ARTICLE
Year : 2020  |  Volume : 9  |  Issue : 1  |  Page : 118-127

Chemical composition, antioxidant, antibacterial, and anticancer activities of scorzonera calyculata boiss. and centaurea irritans wagenitz. Extracts, endemic to iran


1 Department of Chemistry, Islamic Azad University, Central Tehran Branch, Tehran, Iran
2 Department of Biology, Islamic Azad University, Roudehen Branch, Roudehen, Iran

Date of Submission12-Sep-2019
Date of Acceptance16-Mar-2020
Date of Web Publication26-Jun-2020

Correspondence Address:
Dr. Shiva Masoudi
Department of Chemistry, Islamic Azad University, Central Tehran Branch, P.O. Box 86831-14676, Tehran.
Iran
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Source of Support: None, Conflict of Interest: None


DOI: 10.4103/jrptps.JRPTPS_97_19

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  Abstract 

Background & Purpose: This research focused on the composition for the essential oils, which was obtained by solvent-free microwave extraction (SFME) from the aerial parts of Scorzonera calyculata, and hydrodistilled oils from the aerial parts and roots of Centaurea irritans, from Astraceae family, were investigated by gas chromatography (GC) and GC/mass spectrometry (MS). In addition, the biological activities of the methanolic extracts from the aerial parts of S. calyculata and C. irritans were determined. Methods: Total phenolic content was determined by the Folin–Ciocalteu procedure. Antibacterial activity of the methanolic extracts was carried out by minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC). Cytotoxicity of the methanolic extract of S. calyculata against human lung cancer cells (A549) and the methanolic extract of C. irritans against breast lung cancer cells (MCF-7) were measured using 3-(4, 5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. Results: The obtained results of GC/MS technique showed that the SFME oil of S. calyculata, was rich in regard to nonterpenoid and sesquiterpene components. Both oils from the aerial parts and roots of C. irritans were rich in regard to oxygenated monoterpenes. The S. calyculata and C. irritans extracts showed moderate antioxidant activities with an inhibitory concentration (IC50) value of 1.48 and 1.99 mg/mL, using 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay and 73.51 and 44.48 μmol Fe (II)/g dry mass using ferric-reducing antioxidant power (FRAP) assay, respectively. The extracts showed high toxicity against gram-positive bacteria and the IC50 value of extracts cytotoxicity was found to be 9.8 and 10.3 mg/mL, respectively. Conclusion: It appeared that the investigated samples could be as a promising drug for pharmaceutical industry.

Keywords: Antibacterial activity, anticancer activity, antioxidant capacity, Centaurea irritans Wagenitz, essential oil, Scorzonera calyculata Boiss


How to cite this article:
Ayromlou A, Masoudi S, Mirzaie A. Chemical composition, antioxidant, antibacterial, and anticancer activities of scorzonera calyculata boiss. and centaurea irritans wagenitz. Extracts, endemic to iran. J Rep Pharma Sci 2020;9:118-27

How to cite this URL:
Ayromlou A, Masoudi S, Mirzaie A. Chemical composition, antioxidant, antibacterial, and anticancer activities of scorzonera calyculata boiss. and centaurea irritans wagenitz. Extracts, endemic to iran. J Rep Pharma Sci [serial online] 2020 [cited 2020 Dec 2];9:118-27. Available from: https://www.jrpsjournal.com/text.asp?2020/9/1/118/287597


  Introduction Top


The Scorzonera is a genus belonging to the family Asteraceae, and it grows mainly in dry areas of Europe and Asia. It also contains approximately 175 species distributed throughout Europe, Asia, and Africa.[1],[2] The genus Scorzonera is represented in the flora of Iran by 50 species, in which 22 of them are endemic.[3],[4] Some species of Scorzonera are used for cooking vegetables and in traditional medicine in Europe and Asia. Furthermore, these plants are used in the Mongolian and Chinese folk medicine to prolong the period of lactation. Moreover, this species is also used as antifebrile, against bacterial and viral infections, as well as in the treatment of the poisonous ulcer, gastric, and intestinal disorders.[5],[6],[7]Scorzonera hispanica L. is the most recognized species that grows naturally and widely in Europe where it has been cultivated since the seventeenth century as a food source. Scorzonera undulata is a perennial species, diploid, and a highly polymorphic plant. S. undulata is mostly purposed as food source; however, in Tunisia, the roots are appreciated for their sweetness; they are either eaten raw or cooked in water. They are also used for preparing a decoction for its benefits as depurative. The ashes of burned roots are very effective in the treatment of burns.[8]Scorzonera austriaca is widely distributed in the northeast and northwest in China. It has been widely used for curing fever, carbuncle, and mastitis as a traditional herbal medicine. Also S. austriaca is used to treat hepatitis B as a folk medicine.[9],[10] In Turkish folk medicine, members of the genus Scorzonera are used for treating a variety of illnesses, including arteriosclerosis, kidney diseases, hypertension, diabetes mellitus, and rheumatism, as well as for pain relief and healing different injuries.[11],[12] Antioxidant, analgesic, anti-inflammatory, and wound healing activities of some Scorzonera species have been reported previously.[13],[14],[15] Antioxidant activity and antimicrobial effects in Scorzonera suberosa, Scorzonera latifolia, and Scorzonera laciniata have been reported from Turkish region. According to the result, using plant extraction has high antioxidant and antiradical effects. All plant samples have more pronounced antimicrobial effect on Escherichia coli and Bacillus megaterium. In addition, these samples show antitoxic property and protective effect of cell viability in the probiotic yeast culture.[16] The genus Scorzonera is known for the presence of variety of compounds, and previous investigations have led to the isolation of triterpenoids,[17],[18],[19] coumarins,[20] lignans,[21] sesquiterpene lactones, and sesquiterpene glucosides,[5],[22] flavonoid glucosides,[23],[24],[25] dimeric guaianolides,[26] and phenolic compounds.[27],[28],[29]Centaurea L. is a large genus, which comprised several species, many of which are used in folk medicine. It is one of the biggest genera of family Asteraceae as this genus has over 400–700 species and 199 taxons.[30] Seventy-four species of the genus Centaurea are found in Iran, among which 38 are endemic. Various Centaurea species have certain biological activities and are used as anti-inflammatory,[31] antimicrobial,[32] as diuretic and mild astringent,[33] antihepatotoxic,[34] antioxidant,[35] and cytotoxic agent.[36] Extensive chemical investigations of Centaurea species led to the isolation and identification of various types of compounds including alkaloids,[37] lignans,[38] aglycone flavonoids,[39] and sesquiterpene lactones.[40],[41],[42]Centaurea cyanus flower, also known as blue cornflower or bachelor’s button, grows as a wild and common garden plant throughout Europe.[43] Owing to its intense blue flowers, it is used as an ornamental plant, for coloring sugar and confectionaries, in teas and salads, and to garnish dishes.[43],[44] Several therapeutic activities have also been attributed to the flowers, including the treatment of indigestion, gallbladder dysfunction, kidney regulation, menstrual disorder regulation, increasing immunity, and for the efficient cleaning of wounds.[44],[45]

Throughout this study, the analysis of the essential oils obtained by solvent-free microwave extraction (SFME) from leaves and flowers of Scorzonera calyculata and hydrodistilled oils from the aerial parts and roots of Centaurea irritans are reported. Also the antioxidant, antibacterial, and anticancer potentials of the methanolic extract from the aerial parts of the plants were investigated. To the best of our knowledge, this is the first report on the oil composition and biological activities of S. calyculata and C. irritans growing wild in Iran.


  Materials and Methods Top


Plant preparation

The aerial parts of S. calyculata and the aerial parts and roots of C. irritans, which are endemic to Iran, were collected during the flowering stage from Mehran, Province of Ilam, west of Iran, in June and July 2017, respectively. Voucher specimens have been deposited at the Herbarium of the Research Institute of Forests and Rangelands (TARI), Tehran, Iran. Plant specimens were authenticated by Dr. Vali-Allah Mozaffarian from the same institute.

Isolations of the essential oils

Distillation

Air-dried aerial parts (100 g) and roots (70 g) of C. irritans were separately subjected to hydrodistillation using a Clevenger-type apparatus for 4h. After decanting and drying off the oils over anhydrous sodium sulfate, the corresponding yellowish-colored oils were recovered in a yield of 0.16% and 0.10% (wt/wt), respectively.

Solvent-free microwave extraction

SFME extraction was performed in a Milestone ETHOS 1600 batch reactor (Milestone Srl, Sorisole (BG), Italy), which is a multimode microwave reactor operating at 2455 MHz with a maximum delivered power of 1000 W, variable in 10 W increments. The dimensions of the polytetrafluoroethylene-coated cavity are 35 × 35 × 35 cm. During the experiment, time, temperature, pressure, and power were controlled by using the “easy-WAVE” software package (GPS Limited, London, UK). Temperature was monitored with the aid of a shielded thermocouple (ATC-300, Java Multi Mandiri Cv, Indonesia) inserted directly into the sample container. In a typical SFME procedure, 250 g of dry leaves and flowers of S. calyculata were moistened before extraction by soaking in water for 1h, then draining off the excess water. This step is essential for giving the leaves and flowers the initial moisture. Moistened leaves and flowers also were next placed in a reactor without any added solvent or water. The essential oil is collected, dried with anhydrous sodium sulfate, and stored at 0°С until used.

Gas chromatography

Gas chromatography (GC) analysis was performed on Schimadzu 15A (Shimadzu, Kyoto, Japan) gas chromatograph equipped with a split/splitless injector (25°С) and a flame ionization detector (250°С). Nitrogen was used as carrier gas (1 mL/min), and the capillary column used was a DB-5 (50 m × 0.2mm, film thickness, 0.32 μm). The column temperature was kept at 60°С for 3 min and then heated to 220°С with a 5°С/min rate and kept constant at 220°С for 5 min. Relative percentage amounts were calculated from the peak area using a Shimadzu C-R4A Chromatopac, without the use of correction factors.

Gas chromatography-mass spectrometry

GC/mass spectrometry (MS) analysis was carried out using a Hewlett-Packard 5973 MSD detector (Agilent Technologies, Santa Clara, CA, USA) with a HP-5 MS column (30 m × 0.25mm, film thickness, 0.25 μm). The column temperature was kept at 60°С for 3 min and programmed to 220°С at a rate of 5°С/min and kept constant at 220°С/min for 5 min. The injector and GC/MS interphase were also maintained at 270°С. The flow rate of helium, as carrier gas, was 1 mL/min, with a split ratio of 1/50. The ionization voltage was 70eV. The ion source temperature was 250°С, and the transfer line temperature was 280°С. In addition, the mass range (m/z) was 45–465 amu (atomic mass unit) at a speed of 2.8 scan/s. The retention indicates that all the components determined according to the van den Dool method, using n-alkanes as standards. As a result, the compounds were identified (RRI, DB5) by comparison with the data reported in the literature and by comparison of their MS with either the Wiley library or with the published mass spectra.[46],[47]

Preparation of methanolic extracts

Extracts were prepared by cold percolation method. The aerial parts of S. calyculata and the aerial parts of C. irritans were dried at room temperature and ground with a blender. Approximately 30 g of the powders were macerated in 200 mL of methanol 80% in water for 48h in room temperature by shaking. The extracts were filtered, and methanol was evaporated at 40°С in rotary evaporator. The extracts were lyophilized and kept in dark at +4°С until tested.

Solvents and chemicals

Ferric chloride (FeCl3·6H2O), ascorbic acid, gallic acid, methanol, Folin–Ciocalteu reagent, sodium acetate trihydrate (C2H3NaO2·3H2O), acetic acid, hydrochloric acid, ferrous sulfate (FeSO4·7H2O), and sodium carbonate were purchased from Merck (Darmstadt, Germany); 2, 2-Diphenyl-1-picrylhydrazyl (DPPH), 2, 4, 6-tri [2-pyridyl]-s-triazine (TPTZ), and 3-(4, 5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) were purchased from Sigma Chemical (Sigma–Aldrich, Sternheim, Germany). All the other chemicals were of analytical grade or more pure.

Determination of total phenolic contents

The amount of total phenolic content (TPC) of both plant extracts was determined according to the Folin–Ciocalteu method[48] and expressed as gram of gallic acid equivalent (GAE) per gram of dry weight of extract. A volume of 50 μL of the extracts (different concentrations), 450 μL of distilled water, and 500 μL of Folin–Ciocalteu reagent 0.5N were mixed and incubated at room temperature for 15 min. A total of 500 μL of standard sodium carbonate 1% was added, incubated in the dark for 30 min at room temperature, and absorbance was measured at 765 nm using UV spectrophotometer (UV-1800 Shimadzu). TPC of the samples was calculated from calibration curve of gallic acid. All samples were analyzed in triplicates. The gallic acid standard curve was established by plotting concentration (mg/mL) versus absorbance (nm) as follows:

(Y = 35.96X – 0.0096, R2 = 0.998), where Y is absorbance and X is concentration in GAE.

2, 2-Diphenyl-1-picrylhydrazyl radical scavenging assay

The antioxidant activity of the methanolic extracts of both plants was measured in terms of hydrogen donation or free radical scavenging ability by using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) stable radical.[49] The reaction mixture comprised 20 μL of various concentrations of methanolic extracts and 250 μL of methanol solution of DPPH 1mM. The reaction mixture was incubated for 30 min in the dark at room temperature. The absorbance was measured at 517 nm using UV spectrophotometer (UV-1800 Shimadzu) against control. Ascorbic acid was used as standard control. Inhibition of DPPH-free radical in percent was calculated by the following formula:



where Ac is the absorbance of the control and As is the absorbance of the tested sample. All tests were carried out in triplicate. The inhibition concentration at 50% inhibition (IC50) was the parameter used to compare the radical scavenging activity.

Ferric-reducing antioxidant power assay

The ability of both plant extracts to reduce Fe (III)/tripyridyl triazine complex was assessed by ferric-reducing antioxidant power (FRAP) assay.[50] The stock solution included 300mM acetate buffer (pH = 3.6), 10mM TPTZ (2, 4, 6-tripyridyl-s-triazine) solution in 40mM HCl, and 20mM FeCl3·6H2O, solution. The fresh working solution was prepared by mixing 200 mL of acetate buffer, 20 mL of TPTZ, and 20 mL of FeCl3·6H2O. The temperature of the solution was raised to 37°С before use. A volume of 5 μL of the extracts (different concentrations) were mixed with 295 μL of distilled water and were allowed to react with 1000 μL of the FRAP solution for 30 min in the dark. The absorbance of reaction mixtures was measured at 593 nm by UV spectrophotometer (UV-1800 Shimadzu), using FRAP working solution as blank. FRAP of the extracts was determined thrice in comparison with FeSO4·7H2O standard curve. The standard curve was linear between 0.005 and 0.06 μmol FeSO4·7H2O. Results were expressed as μmol Fe (II)/g dry mass and compared with ascorbic acid as positive control.

Antibacterial activity assay

The microdilution method was used to determine the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of the methanolic extracts from the aerial parts of S. calyculata and the aerial parts of C. irritans, using 96-well microtitration plates.[51],[52] The antibacterial activities of the extracts were tested against three gram-positive and three gram-negative bacteria. The gram-positive bacteria included Staphylococcus aureus ATCC 25923, Bacillus subtilis ATCC 23857, and Streptococcus pyogenes ATCC 19615, and the gram-negative bacteria included Klebsiella pneumoniae ATCC 13883, Pseudomonas aeruginosa ATCC 15442, and Listeria monocytogenes ATCC 19115. The bacteria were obtained from the Iranian Research Organization of Science and Technology. At first, the selected bacteria were cultured in tryptic soy broth at 37°С, and the concentration of these cultures was adjusted to 108 CFU/mL using phosphate-buffered saline (PBS). The bacterial suspension was inoculated into a 96-well microplate, which contained serial dilution of S. calyculata and C. irritans extracts (3.125–200 mg/mL). The microplate was incubated at 37°С for 24h. The MIC value was defined as the lowest concentration of the extract that showed no visible turbidity after incubation. To determine MBC, for each set of test tubes in the MIC determination, a loopful of broth was collected from those tubes, which did not show any growth, and incubated on Mueller–Hinton agar by streaking. The plates were incubated at 37°С for 24h again. After incubation, the concentration at which no visible growth was seen was noted as MBC. All the experiments were carried out in triplicates, and the mean was calculated. In addition, ampicillin (5–160 μg/mL) was used as standard positive control.

Anticancer activity test

Colorimetric MTT (3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyl tetrazolium bromide) assay was used for the evaluation of anticancer activity of the methanolic extracts from the aerial parts of S. calyculata and the aerial parts of C. irritans against human lung cancer cell line (A549) and breast cancer cell line (MCF-7), respectively. A549 cells and MCF-7 cells were plated in 96-well tissue culture plate separately at a density of 1 × 104 cells/well and incubated at 37°С for 24h. Subsequently, the cells were treated with various concentration of extracts ranging from 3.125 to 200 mg/mL. After incubation for 24h, the cells were incubated with MTT for 4h at 37°С. After removing the medium from the plate, 100 µL of DMSO was added to each well. Finally, the absorbance of each well was measured at 570 nm by UV spectrophotometer plate reader (Stat Fax 4200, Awareness Technologies, Westport, CT, USA), and the cell cytotoxicity of the extracts was calculated using the following formula:



where OD is the optical density. Moreover, the IC50 value of the extracts was evaluated.


  Results Top


Composition of the essential oils

The identified volatile components and their peak area percentages of the leaves and flowers of S. calyculata obtained by SFME, and those of aerial parts and roots of C. irritans obtained by hydrodistillation are given in [Table 1] and [Table 2], respectively. The components are listed in order of their elution on the DB-5 column. As shown in Table 1, 87.04% (77 components) of the solvent free microwave extraction oil of S. calyculata was identified. The main components in the oil were 6, 10, 14-trimethyl-2-pentadecanone (27.73%) and caryophyllene oxide (16.84%). Other notable constituents were neophytadiene (7.68%) and (E)-β-ionone (6.77%). According to these results, the oil was rich with respective to nonterpenoid compounds (50.35%), whereas the sesquiterpene fractions were 22.56%. The monoterpene and diterpene fractions of the oil were relatively small, representing 5.79% and 8.34% of the total oil. It can be seen from [Table 2], that the composition of the aerial part and the root oils of C. irritans are more different in quantity than quality. Twenty-nine compounds were identified in the aerial part oil of the plant, which is representing 100% of the whole oil composition. The main compounds were geranial (38.62%) and neral (28.08%). In the root oil, 30 compounds were identified, representing 96.01% of the whole oil composition. The main compounds were 8-hydroxy isobornyl isobutyrate (33.12%), geranial (22.26%) and neral (17.52%). As can be seen from the aforementioned information, both oils were characterized by large amounts of oxygenated monoterpenes (72.47% and 73.25%, respectively), whereas the sesquiterpene and nonterpenoid fractions of the oils, representing 18.47% and 7.55% and 8.71% and 15.21% of the total oils, respectively.
Table 1: Chemical composition (%) of the oils obtained by solvent-free microwave extraction from leaves and flowers of
Scorzonera calyculata


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Table 2: Comparative percentage composition of the aerial part and root oils of Centaurea irritans

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Total phenolic content

The TPC of the methanolic extracts of the aerial parts of S. calyculata and the aerial parts of C. irritans was determined to be 4.68 and 3.78 mg GAE/g sample, respectively. The phenolic assay involving an electron-transfer reaction was evaluated using the Folin–Ciocalteu reagent. The TPC measures both types of antioxidants, hydrophobic and hydrophilic, in complex with Fe2+. Phenols and flavonoids are known to inhibit lipid peroxidation by quenching lipid peroxy radicals and to reduce or chelate iron in lipoxygenase enzyme and thus prevent initiation of lipid peroxidation reaction.[53]

2, 2-Diphenyl-1-picrylhydrazyl results

The results of DPPH test of the methanolic extracts of the aerial parts of S. calyculata and the aerial parts of C. irritans were dose dependent. The IC50 value of the extracts was 1.48 and 1.99 mg/mL, respectively. These values were found to be more than ascorbic acid as standard (0.09 mg/mL).

Ferric ion reducing power

FRAP values of the samples were 73.51 and 44.48 μmol Fe (II)/g dry mass, respectively. The FRAP value of the methanolic extracts was significantly lower than that of ascorbic acid (7370.84 μmol/g). FRAP assay is widely used in the evaluation of the antioxidant component in dietary polyphenols.[54]

Antibacterial activity

The MIC test was conducted to determine the lowest concentration of the extracts that inhibits the bacterial growth. In addition, the MBC is the lowest concentration of an antibacterial agent required to kill a particular bacterium. The results showed that antibacterial activity of extracts were dose dependent. The antibacterial activity showed that the extract of aerial parts of S. calyculata had the most effect on S. aureus ATCC 25923 with lower MIC value. The highest and lowest MIC values were belonged to K. pneumoniae and S. aureus, respectively [Table 3]. Also, the antibacterial activity revealed that the extract of aerial parts of C. irritans had the most effect on B. subtilis with lower MIC value. The highest and lowest MIC values belonged to K. pneumoniae and B. subtilis, respectively [Table 4]. Ugur et al. showed that ethanolic and chloroform extract of Scorzonera sandrasica had significant antibacterial activity against multiresistant strains of Stenotrophomonas maltophila.[55]
Table 3: Antibacterial activity of the methanolic extract of Scorzonera calyculata

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Table 4: Antibacterial activity of the methanolic extract of the aerial parts of Centaurea irritans

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Anticancer activity

The anticancer activity of the extracts was performed using MTT method in various concentrations. As indicated in [Figure 1], after incubation of cells in different concentrations for 24 h, the significant cytotoxicity was observed in 200 mg/mL compared with control (untreated cells) (P < 0.05). Moreover, the IC50 value cytotoxicity of extract of the aerial parts of S. calyculata on A549 cell line was 9.8 mg/mL. In [Figure 2], the significant cytotoxicity was observed in 100 mg/mL compared with control (untreated cells) (P < 0.05). Moreover, the IC50 value cytotoxicity of extract of the aerial parts of C. irritans on MCF-7 cell line was 10.3 mg/mL.
Figure 1: Survival percentage of A549 cells against various concentrations of the extract of Scorzonera calyculata within 24 h. n = 3; ***P < 0.001, **P < 0.01, *P < 0.05. Results have been reported as survival rate compared with control samples

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Figure 2: Survival percentage of MCF-7 cells against various concentrations of the extract of Centaureairritans within 24 h. n = 3; ***P < 0.001, **P < 0.01, *P < 0.05. Results have been reported as survival rate compared with control samples

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  Discussion Top


Only a few studies on the chemical composition of the oils of Scorzonera species have previously been reported. The chemical composition and antibacterial activities of volatile components from capitula and aerial parts of S. undulata have been described. In fact, 36 constituents were identified in the oil and the main components of them were methyl hexadecanoate (30.4%), methyl linoleate (23.9%) and heneicosane (12.2%). The Scorzonera undulata oil exhibited an interesting antibacterial activity against gram-positive and gram-negative bacteria but no antifungal activity was detected.[56] Previous investigation on oils of the Centuarea genus showed varying compositions. The oil of C. imperialis, growing in Iran, was found to contain caryophyllene oxide (23.2%), germacrene D (19.7%) and β-caryophyllene (14.1%) as the major constituents.[57] Water-distilled oils obtained from the aerial parts of C. depressa and C. solstitialis and flower of C. ispahanica have been the subject of our previous studies. Piperitone (35.2%) and elemol (14.1%) were detected in C. depressa, as the major components.[58] The oil of C. solstitialis was found to contain hexadecanoic acid (30.8%) and caryophyllene oxid (25.2%) as the major constituents.[59] The dominant compounds in the oil of C. ispahanica were benzyl benzoate (26.5%), hexadecanoic acid (17.1%), benzyl salicylate (16.6%) and caryophyllene oxide (12.8%).[60] The oil from the aerial parts of C. grinensis from Croatia, contained 4-vinyl guaiacol (21.5%), hexadecanoic acid (16.2%) and acetophenone (12.5%) as the major components. The dominant compounds in the oil of C. apiculate from Bulgaria, were caryophyllene oxide (15.8%), spathulenol (14.5%) and humulene epoxide II (9.4%).[61]

Several studies have shown the anticancer activity of Scorzonera species. Yang et al.[62] indicated that the cytotoxicity of Scorzonera divaricata Turcz. against HL-60 and Hep-G2 cell lines was 14.6μg/mL.

Recently we analyzed the chemical composition of the ethanolic extract of the aerial parts of S. calyculata by GC/MS.

A total of 27 compounds were identified in the S. calyculata extract, among which, 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (30.79%) was the major one.[63]

This flavonoid compound contains therapeutic application such as, antioxidant, antimicrobial, anti-inflammatory and antiproliferative.[64] The other notable compounds in the extract of the plant were propylamin-N[9-borabicyclo{3, 3, 1}non-9yl (7.15%) which has antimicrobial activity,[64]hexadecanoic acid (6.12%), which has anti-inflammatory, antioxidant, antipsychotic and anti-allergic activities,[65] and neophytadiene (3.86%) which has strong bactericidal, anti-inflammatory and antifungal activities.[66]

More ever, S. calyculata extract is full of polyphenolic compounds, thus all the aforementioned compounds could have potentially been the cause of antioxidant, antibacterial and anticancer properties of the S. calyculata.

According to our recently reported on the chemical composition of the ethanolic extract of the aerial parts of S. calyculata, many of the identified components belonged to the polyphenolic compounds, such as 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one, which was the major one. Polyphenolic compounds can play a key role in determining the biological properties of the S. calyculata extract.

Financial support and sponsorship

Nil.

Conflicts of interest

There are no conflicts of interest.



 
  References Top

1.
Bohm BA, Stuessy TF. Flavonoids of the Sunflower Family (Asteraceae). Wien, Austria: Springer-Verlag;2001.  Back to cited text no. 1
    
2.
Brahim H, Akkal S, Bayat C, Laouer H, Dijoux Franca MG. Secondary metabolites from Scorzonera undulata ssp. deliciosa (Guss.) Maire (Asteraceae) and their antioxidant activities. Rec Nat Prod 2010;4:171-5.  Back to cited text no. 2
    
3.
Mozaffarian V. Dictionary of Iranian Plant Names. Tehran, Iran: Farhang Moaser;1996. p. 491-4.  Back to cited text no. 3
    
4.
Safavi SR, Naseh Y, Jafari E, Tavakoli Z, Heydarnia N. Scorzonera L. In:Flora of Iran (Asteraceae, Tribe Cichorieae). Tehran, Iran: Research Institute of Forests & Rangelands Press;2013. p. 352-442.  Back to cited text no. 4
    
5.
Zidorn C, Ellmerer-Müller EP, Stuppner H. Sesquiterpenoids from Scorzonera hispanica L. Pharmazie 2000;55:550-1.  Back to cited text no. 5
    
6.
Tsevegsuren N, Edrada R, Lin W, Ebel R, Torre C, Ortlepp S, et al. Biologically active natural products from Mongolian medicinal plants Scorzonera divaricata and Scorzonera pseudodivaricata. J Nat Prod 2007;70:962-7.  Back to cited text no. 6
    
7.
Wang Y, Edrada-Ebel R, Tsevegsuren N, Sendker J, Braun M, Wray V, et al. Dihydrostilbene derivatives from the Mongolian medicinal plant Scorzonera radiata. J Nat Prod 2009;72:671-5.  Back to cited text no. 7
    
8.
Abdelkader H, Salah KB, Liouane K, Boussaada O, Gafsi K, Mahjoub MA. Antimicrobial activity of Rhaponticum acaule and Scorzonera undulata growing wild in Tunisia. Afr J Microbial Res 2010;4:1954-8.  Back to cited text no. 8
    
9.
Xie Y, Wang J, Geng YM, Qu YF, Zhang Z, Wang GS. Experimental studies on inhibitory effects of total flavonoids in Scorzonera austriaca wild on hepatitis B virus in νitro. Chin J Biochem Pharm 2015;8:41-3, 47.  Back to cited text no. 9
    
10.
Zhang TW, Xie Y, Zhang Z, Wang GS. Study on hepatoprotective effects of total flavonoids in Scorzonera austriaca wild in νiνo and in νitro. Chin J Biochem Pharm 2015;5:6-9, 13.  Back to cited text no. 10
    
11.
Sezik E, Yesilada E, Tabata M, Honda G, Takaishi Y, Fujita T, et al. Traditional medicine in Turkey VIII. Folk medicine in East Anatolia; Erzurum, Erzincan, Agri, Kars, Igdir Provinces. Econ Bot 1997;51:195-211.  Back to cited text no. 11
    
12.
Baytop T. Therapy with Medicinal Plants in Turkey—Past and Present. Ankara, Turkey: Nobel Publishers;1999.  Back to cited text no. 12
    
13.
Küpeli Akkol E, Acıkara OB, Süntar I, Citoğlu GS, Keleş H, Ergene B. Enhancement of wound healing by topical application of Scorzonera species: Determination of the constituents by HPLC with new validated reverse phase method. J Ethnopharmacol 2011;137:1018-27.  Back to cited text no. 13
    
14.
Küpeli Akkol E, Bahadır Acıkara O, Süntar I, Ergene B, Saltan Çitoğlu G. Ethnopharmacological evaluation of some Scorzonera species: In vivo anti-inflammatory and antinociceptive effects. J Ethnopharmacol 2012;140:261-70.  Back to cited text no. 14
    
15.
Acikara ÖB, Hošek J, Babula P, Cvačka J, Budešínský M, Dračinský M, et al. Turkish Scorzonera species extracts attenuate cytokine secretion via inhibition of NF-kB activation, showing anti-inflammatory effect in vitro. Molecules 2015;21:43.  Back to cited text no. 15
    
16.
Erden Y, Kirbağ S. Chemical and biological activities of some Scorzonera species: An in vitro study. Proc Natl Acad Sci India Sect B Biol Sci 2015;85:319-26.  Back to cited text no. 16
    
17.
Oksuz S, Goren N, Ulubelen A. Terpenoids from Scorzonera tomentosa. Fitoterapia 1990;61:92-3.  Back to cited text no. 17
    
18.
Bin W, Guo QL, Pei JQ, Hua SG. Two new olean-type triterpene fatty esters from Scorzonera mongolica. Chin Chem Lett 2007;18:708-10.  Back to cited text no. 18
    
19.
Ҫitoğlu GS, Bahadir Ö, Dall’Acqua S. Dihydroisocoumarin derivatives isolated from the roots of Scorzonera latifolia. Turk J Pharm Sci 2010;7:205-12.  Back to cited text no. 19
    
20.
Paraschos S, Magiatis P, Kalpoutzakis E, Harvala C, Skaltsounis AL. Three new dihydroisocoumarins from the Greek endemic species Scorzonera cretica. J Nat Prod 2001;64:1585-7.  Back to cited text no. 20
    
21.
Zidorn C, Ellmerer EP, Sturm S, Stuppner H. Tyrolobibenzyls E and F from Scorzonera humilis and distribution of caffeic acid derivatives, lignans and tyrolobibenzyls in European taxa of the subtribe Scorzonerinae (Lactuceae, Asteraceae). Phytochemistry 2003;63:61-7.  Back to cited text no. 21
    
22.
Li J, Wu QX, Shi YP, Zhu Y. A new sesquiterpene lactone from Scorzonera austriaca. Chin Chem Lett 2004;15:1309-10.  Back to cited text no. 22
    
23.
Menichini F, Statti G, Delle Monache F. Flavonoid glycosides from Scorzonera columnae. Fitoterapia 1994;65:555-6.  Back to cited text no. 23
    
24.
Jiang TF, Wang YH, Lv ZH, Yue ME. Determination of kava lactones and flavonoid glycoside in Scorzonera austriaca by capillary zone electrophoresis. J Pharm Biomed Anal 2007;43:854-8.  Back to cited text no. 24
    
25.
Xie Y, Guo QS, Wang GS. Flavonoid glycosides and their derivatives from the herbs of Scorzonera austriaca Wild. Molecules 2016;21:1-9.  Back to cited text no. 25
    
26.
Zhu Y, Wu QZ, Hu PZ, Wu WS. Biguaiascorzolides A and B: Two novel dimeric guaianolides with a rare skeleton, from Scorzonera austriaca. Food Chem 2009;114:1316-20.  Back to cited text no. 26
    
27.
Sari A, Zidorn C, Ellmerer EP, Özgökçe F, Ongania KH, Stuppner H. Phenolic compounds from Scorzonera tomentosa L. Hel Chim Acta 2007;90:311-7.  Back to cited text no. 27
    
28.
Sarı A. Phenolic compounds from Scorzonera latifolia (Fisch. & Mey.) DC. Nat Prod Res 2012;26:50-5.  Back to cited text no. 28
    
29.
Nanzad T, Ruangelie E, Wenhan L, Rainer E, Claudia T, Sofia O, et al. Biologically active natural products from Mongolian medicinal plants Scorzonera divaricata and Scorzonera pseudodivaricata. J Nat Prod 2007;70:962-7.  Back to cited text no. 29
    
30.
Garcia-Jacas N, Susanna A, Garnatje T, Vilatersana R. Generic delimitation and phylogeny of the subtribe Centaureinae (Asteraceae): A combined nuclear and chloroplast DNA analysis. Ann Bot 2001;87:503-15.  Back to cited text no. 30
    
31.
Erel SB, Demir S, Nalbantsoy A, Ballar P, Khan S, Yavasoglu NU, et al. Bioactivity screening of five Centaurea species and in vivo anti-inflammatory activity of C. athoa. Pharm Biol 2014;52:775-81.  Back to cited text no. 31
    
32.
Ugur A, Sarac N, Ceylan O, Emin Duru M. Antimicrobial activity and chemical composition of endemic Centaurea cariensis subsp. Niveo-tomentosa. Nat Prod Res 2010;24:861-72.  Back to cited text no. 32
    
33.
Ali YE, Omar AA, Sarg TM, Slatkin DJ. Chemical constituents of Centaurea pallescens. Planta Med 1987;53:503-4.  Back to cited text no. 33
    
34.
Abdallah HM, Mohamed MA, Abdou AM, Hamed MM. Protective effect of Centaurea pallescens, Del. Against CCL4-induced injury on a human hepatoma cell line (Huh 7). Med Chem Res 2013;22:5700-6.  Back to cited text no. 34
    
35.
Ugur A, Duru ME, Ceylan O, Sarac N, Varol O, Kivrak I. Chemical composition, antimicrobial and antioxidant activities of Centaurea ensiformis Hub.-Mor. (Asteraceae), a species endemic to Mugla (Turkey). Nat Prod Res 2009;23:149-67.  Back to cited text no. 35
    
36.
Yirtici U, Yılmaz F, Serim G, Kirimer N, Ulukaya E, Icgen B, et al. The cytotoxic effect of endemic Centaurea fenzlii Reichardt on colon cancer cell lines. Planta Med 2012;78:1125.  Back to cited text no. 36
    
37.
Sarker SD, Laird A, Nahar L, Kumarasamy Y, Jaspars M. Indole alkaloids from the seeds of Centaurea cyanus (Asteraceae). Phytochemistry 2001;57:1273-6.  Back to cited text no. 37
    
38.
Shoeb M, Macmanus SM, Kong-Thoo-Lin P, Celik S, Jaspars M. Bioactivity of the extracts and isolation of lignans and a sesquiterpene from the aerial parts of Centaurea pamphylica (Asteraceae). Daru 2007;15:118-22.  Back to cited text no. 38
    
39.
Nacer A, Bernard A, Boustie J, Touzani R, Kabouche A. Aglycone flavonoids of Centaurea tougourensis from Algeria. Chem Nat Compd 2006;42:230-1.  Back to cited text no. 39
    
40.
Bruno M, Paternosta MP, Gedris TE, Herz W. Sesquiterpene lactones and other constituents of Centaurea nicaensis. Phytochemistry 1996;41:335-6.  Back to cited text no. 40
    
41.
Grienke U, Radić Brkanac S, Vujčić V, Urban E, Ivanković S, Stojković R, et al. Biological activity of flavonoids and rare sesquiterpene lactones isolated from Centaurea ragusina L. Front Pharmacol 2018;9:972.  Back to cited text no. 41
    
42.
Skaltsa H, Lazari D, Panagouleas C, Georgiadou E, Garcia B, Sokovic M. Sesquiterpene lactones from Centaurea thessala and Centaurea attica. antifungal activity. Phytochemistry 2000;55:903-8.  Back to cited text no. 42
    
43.
Chiru T. Phytochemical study of Centaurea cyanus L. U Buch Ser A 2009;52:293-7.  Back to cited text no. 43
    
44.
Chaitanya LG. Food coloring: The natural way. Res J Chem Sci 2014;4:87-96.  Back to cited text no. 44
    
45.
Lim TK. Edible Medicinal and Nonmedicinal Plants. Dordrecht, The Netherlands: Springer;2014.  Back to cited text no. 45
    
46.
Vandendool H, Kratz PD. A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. J Chromatogr 1963;11:463-71.  Back to cited text no. 46
    
47.
Massada Y. Analysis of Essential Oils by Gas Chromatography and Mass Spectrometry. New York: Willey;1976.  Back to cited text no. 47
    
48.
Miliauskas G, Venskutonis P, Van Beek T. Screening of radical scavenging activity of some medicinal and aromatic plant extracts. Food Chem 2004;85:231-7.  Back to cited text no. 48
    
49.
Gorinstein S, Martin-Belloso O, Katrich E, Lojek A, Cíz M, Gligelmo-Miguel N, et al. Comparison of the contents of the main biochemical compounds and the antioxidant activity of some Spanish olive oils as determined by four different radical scavenging tests. J Nutr Biochem 2003;14:154-9.  Back to cited text no. 49
    
50.
Benzie IF, Strain JJ. The ferric reducing ability of plasma (FRAP) as a measure of “antioxidant power”: The FRAP assay. Anal Biochem 1996;239:70-6.  Back to cited text no. 50
    
51.
Samie A, Obi CL, Bessong PO, Namrita L. Activity profiles of fourteen selected medicinal plants from Rural Venda communities in South Africa against fifteen clinical bacterial species. Afr J Biotechnol 2005;4:1443-51.  Back to cited text no. 51
    
52.
Kang CG, Hah DS, Kim CH, Kim YH, Kim E, Kim JS. Evaluation of antimicrobial activity of the methanol extracts from 8 traditional medicinal plants. Toxicol Res 2011;27:31-6.  Back to cited text no. 52
    
53.
Torel J, Cillard J, Cillard P. Antioxidant activity of flavonoids and reactivity with peroxy radical. Phytochemistry 1986;25:383-5.  Back to cited text no. 53
    
54.
Luximon-Ramma A, Bahorun T, Soobrattee AM, Aruoma OI. Antioxidant activities of phenolic, proanthocyanidin, and flavonoid components in extracts of Cassia fistula. J Agric Food Chem 2005;50:5042-7.  Back to cited text no. 54
    
55.
Ugur A, Sarac N, Ceylan O, Duru ME, Beyatli Y. Chemical composition of endemic Scorzonera sandrasica and studies on the antimicrobial activity against multiresistant bacteria. J Med Food 2010;13:635-9.  Back to cited text no. 55
    
56.
Boussaada O, Ammar S, Saidana D, Chriaa J, Chraif I, Daami M. Chemical composition and antimicrobial activity of volatile components from capitula and aerial parts of Rhaponticum acaule and Scorzonera undulata growing wild in Tunisia. Microbiol Res 2008;163:87-95.  Back to cited text no. 56
    
57.
Azadi B, Mojab F. Volatile components of Centaurea imperialis Hausskn. Ex Born. flowering aerial parts. JEOBP 2017;20:259-63.  Back to cited text no. 57
    
58.
Esmaeili A, Rustaiyan A, Nadimi M, Masoudi S, Tadayon F, Sedaghat S, et al Volatile constituents of Centaurea depressa M. B. and Carduus pycnocephalus L. two compositae herbs growing wild in Iran. J Essent Oil Res 2005;17:539-41.  Back to cited text no. 58
    
59.
Esmaeili A, Rustaiyan A, Akbari MT, Moazami N, Masoudi S, Amiri H. Composition of the essential oils of Xanthium strumarium L. and Centaurea sdstitialis L. from Iran. J Essent Oil Res 2006;18:427-9.  Back to cited text no. 59
    
60.
Firouznia A, Akbari MT, Rustaiyan A, Masoudi S, Bigdeli M, Tabatabaei-Anaraki M. Composition of the essential oils of Artemisia turanica Krasch., Helichrysum oocephalum Boiss. and Centaurea ispahanica Boiss. three Asteracea herbs growing wild in Iran. JEOBP 2007;10:88-93.  Back to cited text no. 60
    
61.
Riccobono L, Maggio A, Bruno M, Bancheva S, Santucci O, Senatore F. Chemical composition of the essential oil of Centaurea grinensis Reuter and Centaurea apiculate Ledeb: growing wild in Croatia and Bulgaria, respectively and PCA analysis of Subgenus lopholoma (Cass.) Dobrocz. Plant Biosyst 2017;151:1035-44.  Back to cited text no. 61
    
62.
Yang YJ, Liu X, Wu HR, He XF, Bi YR, Zhu Y, et al. Radical scavenging activity and cytotoxicity of active quinic acid derivatives from Scorzonera divaricata roots. Food Chem 2013;138: 2057-63.  Back to cited text no. 62
    
63.
Ayromlou A, Masoudi S, Mirzaie A. Scorzonera calyculata aerial part extract mediated synthesis of silver nanoparticles: Evaluation of their antibacterial, antioxidant and anticancer activities. J Clust Sci 2019;30:1037-50.  Back to cited text no. 63
    
64.
Ramalakshmi S, Muthuchelian K. Analysis of bio-active constituents of the ethanolic leaf extract of Tabebuia rosea (Bertol.) DC by gas chromatography-mass spectrometry. Int J Chem Tech Res 2011;3: 1054-9.  Back to cited text no. 64
    
65.
Aadesariya MK, Ram VR, Dave PN. Phytochemical analysis of leaves extract of Abutilon pannosuminn-Butanol for its bioactive components through gas chromatography-mass spectrometry (GC-MS). IOSR-JEN 2018;8:11-21.  Back to cited text no. 65
    
66.
Acıkara ÖB, Çitoğlu GS, Dall’Acqua S, Smejkal K, Cvačka J, Zemlička M. A new triterpene from Scorzonera latifolia (Fisch. and Mey.) DC. Nat Prod Res 2012;26:1892-7.  Back to cited text no. 66
    


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