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Chemical Composition and Bioactivities of the Volatile Oil of the Seeds of Eryngium Bungei Boiss

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Chemical Composition and Bioactivities of the Volatile Oil of the Seeds of Eryngium Bungei Boiss Indian Journal of Natural Products and Resources Vol. 9(1), March 2018, pp 9-15 Chemical composition and bioactivities of the volatile oil of the seeds of Eryngium bungei Boiss. Hamid Reza Vahidipour1, Seyed Mehdi Razavi1*, Alireza Ghasemian1 and Gholamhesen Imanzadeh2 1Department of Biology, 2Department of Chemistry, Faculty of Sciences, University of Mohaghegh Ardabili, Ardabil, Iran Received 30 November 2016; Revised 22 September 2017 The volatile oil of the seeds of Eryngium bungei Boiss. (family Apiaceae), was obtained by hydrodistillation and analyzed by the GC-MS and the GC-FID. The analyses revealed at least 69 compounds representing 94 % of the total oil. The results showed that the oil was dominated by chrysanthenyl acetate (20.0 %), spathulenol (17.2 %), endo-isofenchol (10.8 %) and α-pinene (5.1 %). The free-radical-scavenging activity of the oil was evaluated by DPPH assay and RC50 value was calculated as 7.5 µg/mL. The antifungal and phytotoxic activities of the oil were tested against Sclerotinia sclerotiorum, and some common weeds. The MIC value for anti sclerotinia activity of the seed oil was evaluated as 12.5 µg/mL. The IC50 values were determined as 1.32-2.1 µg/mL for inhibitory effects of the oil on seed germination of different weeds. This is the first report on chemical composition and bioactivities of the volatile oils of the seeds of Eryngium bungei. Keywords: Allelopathy, Antifungal activity, Chrysanthenyl acetate, Eryngium bungei, Phytotoxicity. IPC code; Int. cl. (2015.01)−A61K 36/23, 39/00 Introduction 1875 m altitude. The plant was identified in The genus Eryngium L. of Apiaceae family Department of Biology, University of Mohaghegh, comprises 250 annual or perennial species distributed Ardabili. A voucher specimen (No. 1391-3) was all over the world. It is regarded as one of the largest deposited in the herbarium of the Faculty of Basic genera of the Apiaceae with well known Sciences, University of Mohaghegh, Ardabili. pharmaceutical and biological properties1-6. Eryngium Essential oil hydrodistillation bungei Bioss., commonly known as “Zool Khorasani” The ground dried seeds (100 g) of E. bungei were and “Chichagh”, is the most common species of the subjected to hydrodistillation using a Clevenger-type genus distributed from Iran to Afghanistan and Central apparatus for 4 hours to yield 0.25 % of a yellowish Asia7. It has been used in Iranian folk medicine from oil. The extraction process was repeated several times ancient time8. The plant is well known as an appetizer, to obtain enough amounts for biological assays. The diuretic and stimulant agent9-11. It also exhibits oils were dried over anhydrous sodium sulphate and cytotoxic, anti-inflammatory, antibacterial, antifungal, 16 stored at 4 °C in the dark until tested and analyzed . antimalarial, antioxidant, and antihyperglycemic 3 properties . The plant leaves are used as a vegetable, GC-MS and GC-FID conditions 3-8 Online Publishing @ NISCAIR and food flavouring agent, as well . As part of the on- The volatileprovided byoil was analyzed by the GC-MS using a View metadata, citation and similar papers at core.ac.uk CORE going studies on the volatile oils from the Iranian Hewlett Packardbrought GC-MS to you by (GC-7890A & MS-5975C) flora12-15,the authors report the composition of the equipped with a HP-5 fused silica capillary column (30 volatile oils from the seeds of E. bungei and its m×0.25 mm, film thickness 0.25 µm), which was bioactivities, for the very first time. programmed as follows: 60 °C (3 minutes), then 60-230 at 5 °C/min and finally held isothermal at 230 °C for 10 Materials and Methods minutes. The carrier gas was helium (99.999 %) at a Plant material flow rate of 1 mL/ min. Diluted sample (1/20, v/v, in The seeds of Eryngium bungei Boiss. were collected n-hexane) of 1.0 µL was injected manually in a splitless during August 2012 from Oojan, (Birjand, east of Iran), mode. The relative percentage of the volatile oil at 59° 17’ east longitude and 32° 56’ north latitude and constituents was expressed as percentages by peak area normalization. Linear retention indices then were ————— *Correspondent author calculated by injecting series of n-hydrocarbons (C6-C24) E-mail: [email protected] after the oil at the same temperature and conditions. 10 INDIAN J NAT PROD RESOUR, MARCH 2018 For quantitation (area %), the GC-FID analyses of (the half maximal reducing concentration) were then the oil were conducted using a Thermoquest-Finnigan calculated, using the fitted regression line equation in instrument equipped with a HP-5 fused silica column Excel software, and were expressed in µg/mL. (30 m×0.25 mm, film thickness 0.25 µm). Nitrogen was used as the carrier gas at the constant flow of 1 Fungitoxic assay mL/min, the split ratio was same as it was for the GC- The fungitoxic assay was conducted in Completely MS. The oven temperature was raised from 60 to 230 ºC Randomized Design (CRD) with three replications to at a rate of 5 ºC/min and held for 10 minutes. The evaluate the efficacy of the volatile oil as an injector and detector (FID) temperatures were kept at antifungal agent against Sclerotinia sclerotiorum (KACC 41065), using the Poisoned Food 230 and 280 ºC, respectively. Semi-quantitative data 22 was obtained from FID area percentages without the Technique . Four concentrations of the volatile oil (1, use of correction factors. To obtain the same elution 10, 100 and 1000 µg/mL) were prepared in combination with the molten potato dextrose agar order as with GC-MS, simultaneous auto-injection 23 was performed on a duplicate of the same column (PDA) medium using Tween-20 (0.01 % v/v) Sterile applying the same operational conditions. Relative Petri dishes (90 mm diameter) containing 15 mL of percentage amounts of the separated compounds were PDA were used. The positive and negative controls calculated from FID chromatograms. were amphotericin B (10 µg/mL) and distilled water, respectively. In order to eliminate the possible effect Identification of the essential oil components of Tween-20, the same amount of Tween-20 (0.01 % Identification of compounds was performed based v/v) was used to prepare the solutions. The plates on direct comparison of the Kovats indices and MS were inoculated with 6 mm plugs of 7-day-old data with those for standard compounds, and cultures, and their border was sealed with a plastic computer matching with the NIST NBS54K Library film24 and incubated at 25 °C for 3-7 days until the and Wiley Library17,18. Calculations were performed mycelia growth in the negative control plates reaches by using retention times of n-alkanes (C8-C20), the edges of the plates25. Growth inhibition of the which were injected after the oil at the same fungal strain was calculated as the percentage of temperature and conditions. inhibition of radial growth relative to the negative control, using the equation: DPPH assay The free-radical-scavenging property of the volatile IMG (%) = 100[(Dc– Dt)/Dc] oil of E. bungei was evaluated using the DPPH (2,2- diphenyl-1-picrylhydrazyl) assay as described in the Where IMG (%) is inhibition of mycelial growth, Dc literature19-21. DPPH was purchased from Fluka and Dt are average diameters of fungal mycelia Chemie AG, Bucks. The essential oil was dissolved in growth in the negative control and treatment groups, CHCl3 to obtain the stock concentration of 1 mg/mL. respectively. Dilutions were made to obtain concentrations of 5×10- The minimum inhibitory concentration (MIC), 1, 2.5×10-1, 1.25×10-1, 6.25×10-2, 3.13×10-2 and defined as the lowest concentrations that inhibited the 1.56×10-2 mg/mL. Diluted solutions (5 mL each) were visible growth of fungal mycelia after incubation mixed with DPPH (5 mL; 0.08 mg/mL) and allowed (growth was indicated as turbidity), of the volatile oil to stand for 30 min for any reaction to occur. The UV and amphotericin B against S. sclerotiorum was absorbance was recorded at 517 nm. The experiment determined by two-fold dilution method. Six dilutions was performed in triplicate and the average absorption (6.25, 12.5, 25, 50, 100 and 200 µg/mL) of the test was noted for each concentration. The same samples were prepared separately, using potato procedure was followed for the positive control dextrose broth (PDB) and Tween-20 (0.01 % v/v). A ascorbic acid. The percentage of DPPH radical control medium was used without oil and scavenging was estimated, using the following amphotericin B, but with 0.01 % v/v Tween-20. The equation: media were inoculated with10 µL fungal spore suspension and incubated at 25-30 °C for 48 h. I (%) = 100[(Ac – As)/Ac] Phytotoxicity assay where, Ac and As are the absorbance of the negative Phytotoxicity assays were conducted with four control and the samples, respectively. RC50 values replications to examine the effects of the volatile oil VAHIDIPOUR et al.: CHEMICAL COMPOSITION OF ERYNGIUM BUNGEI SEEDS ESSENTIAL OIL 11 on seed germination, and radicle and epicotyl growth epicotyl growth, the above equation was modified of Lettuce (Lactuca sativa), Amaranth (Amaranthus where seed germination (GS) is replaced by radicle retroflexus), Branyard grass (Echinochloa crus-gali), growth (RG) and epicotyl growth (EG), respectively; Wild mustard (Sinapis arvensis), Purslane (Portulaca as follows: oleracea) and Nightshade (Solanum nigrum). All plant seeds were surface sterilized with sodium IRG (%) =100[1− (RGSample/RGControl)] and IEG (%) hypochloride (1 %) for 10 min and rinsed with sterile =100[1− (EGSample/EGControl)] distilled water. Three concentrations of the volatile oil (1, 10 and 100 µg/mL) were prepared by dilution in The half maximal inhibitory concentration (IC50) distilled water, using Tween-20 (0.01 % v/v).
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