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Antibacterial Activity and Composition of the Essential Oil of Ziziphora Clinopodioides Subsp

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Antibacterial Activity and Composition of the Essential Oil of Ziziphora Clinopodioides Subsp Antibacterial Activity and Composition of the Essential Oil of Ziziphora clinopodioides subsp. bungeana (Juz.) Rech. f. from Iran Ali Sonbolia,*, Mohammad Hossein Mirjalilib,c, Javad Hadianb, Samad Nejad Ebrahimid, and Morteza Yousefzadie a Department of Biology, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, Evin, P.O. Box 19835-389, Tehran, Iran. Fax: (+98-21)22418679. E-mail: [email protected] b Department of Horticulture, Faculty of Horticulture and Plant Protection, University of Tehran, Karaj, Iran c Department of Agriculture, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, Evin, Tehran, Iran d Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, Evin, Tehran, Iran e Department of Ecology & Systematic, Research Institute of Applied Sciences, ACECR, Evin, Tehran, Iran * Author for correspondence and reprint requests Z. Naturforsch. 61c, 677Ð680 (2006); received November 29/December 21, 2005 The chemical composition of the essential oil obtained from the aerial flowering parts of Ziziphora clinopodioides subsp. bungeana (Juz.) Rech. f. was analyzed by GC and GC- MS. Thirty-two components representing 97.1% of the total oil were identified. Oxygenated monoterpenes (94.3%) were the predominant fraction of the oil with pulegone (65.2%), iso- menthone (11.9%), 1,8-cineole (7.8%) and piperitenone (6.5%) as the main constituents. Antibacterial activity of the oil and also its two main components (pulegone and 1,8-cineole) were tested against seven bacteria. It was found that the oil exhibited interesting antibacterial activity against Staphylococcus epidermidis, S. aureus, Escherichia coli and Bacillus subtilis with MIC values of 3.75 mg/ml. Key words: Essential Oil Composition, Antibacterial Activity, Ziziphora Introduction survey showed that the oil of Ziziphora species has been found to be rich in pulegone. The main The genus Ziziphora L. (Lamiaceae) consists of constituents found in the oil of Z. vychodceviana four species (Z. clinopodioides Lam., Z. capitata and Z. persica collected from Kazakhestan were L., Z. persica Bunge. and Z. tenuior L.) wide- pulegone (57.5%Ð66%) and isomenthone (5.1%Ð spread all over Iran (Mozaffarian, 1996). Z. clino- 15.7%) (Dembistikii et al., 1995). The major con- podioides Lam. comprises nine subspecies native stituent found in the oil of Z. tenuior L. has been to Iran. Z. clinopodioides subsp. bungeana (Juz.) reported to be pulegone (87.1%) (Sezik et al., Rech. f. grows wild in the eastern parts of Iran 1991). The essential oil of Turkish endemic Z. tau- (Rechinger, 1982). In Iranian folk medicine, Ziz- rica subsp. clenioides was found to contain pule- iphora species have been used as infusion, decoc- gone (81.9%), limonene (4.5%) and piperitenone tion and maceration for various purposes such as (2.3%) (Meral et al., 2002). Here, we report the sedative, stomach tonic, heart disorders, common composition and antibacterial activity of the essen- cold, inflammation, depression, diarrhea, expecto- tial oil of Ziziphora clinopodioides subsp. bun- rant, coughing, antiseptic, migraine, fever and car- geana from Iran which has not been investigated minative (Zargari, 1995; Naghibi et al., 2005). In previously. Iranian folklore, the dried aerial parts of afore- mentioned species have been frequently used as Material and Methods culinary and spice in food. The antibacterial activity of the oil of Z. taurica Plant material subsp. clenioides and Z. taurica has already been The aerial parts of Z. clinopodioides subsp. bun- studied (Tumen and Ayhan, 1992). A literature geana were collected during its flowering stage in 0939Ð5075/2006/0900Ð0677 $ 06.00 ” 2006 Verlag der Zeitschrift für Naturforschung, Tübingen · http://www.znaturforsch.com · D 678 A. Sonboli et al. · Antibacterial Activity and Composition of the Oil of Z. clinopodioides June 2005 from Khorasan Province: Bejestan-Fer- Bioassay procedure dows road, Serideh village, at an altitude of The bacterial species used in this study were: 1300 m. A voucher specimen (MP-921) was depos- Staphylococcus aureus ATCC 25923, Staphylococ- ited in the Medicinal Plants and Drugs Research cus epidermidis ATCC 12228, Bacillus subtilis Institute Herbarium (Tehran, Iran). ATCC 9372, Enterococcus faecalis ATCC 15753, Escherichia coli ATCC 25922, Pseudomonas aeru- Essential oil isolation ginosa ATCC 27852, and Klebsiella pneumoniae ATCC 3583. The inhibition effect on bacterial Air-dried plant material (100 g) was hydrodis- growth was determined by the disc diffusion tilled for 3 h using a Clevenger type apparatus. The method (Baron and Finegold, 1990). The essential oil was dried over anhydrous sodium sulfate and oil (10 μl) and the pure constituents (10 μl of 10% was kept in a sealed vial at 4 ∞C until analysis solution of thymol in MeOH, and 10 μl of pure and tests. Table I. Essential oil composition of Z. clinopodioides Essential oil analysis procedure subsp. bungeana from Iran. GC analysis of the oil was conducted using a Compound RI % Identifica- a Thermoquest-Finnigan instrument equipped with tion method a DB-1 fused silica column (60 m ¥ 0.25 mm i.d., α-Thujene 0924 tb RI, MS film thickness 0.25 μm). Nitrogen was used as the 3-Methyl-cyclohexane 0926 t RI, MS carrier gas at the constant flow of 1.1 ml/min. The α-Pinene 0934 0.5 RI, MS, Co-I oven temperature was held at 60 ∞C for 1 min, Camphene 0948 0.2 RI, MS, Co-I 1-Octen-3-ol 0961 t RI, MS then programmed to 250 ∞C at a rate of 4 ∞C/min, Sabinene 0969 0.3 RI, MS and then held for 10 min. The injector and de- -Pinene 0975 0.7 RI, MS, Co-I tector (FID) temperatures were kept at 250 ∞C Myrcene 0981 0.3 RI, MS, Co-I α and 280 ∞C, respectively. GC-MS analysis was car- -Terpinene 1012 0.1 RI, MS p-Cymene 1015 t RI, MS, Co-I ried out on a Thermoquest-Finnigan Trace GC-MS 1,8-Cineole 1027 7.8 RI, MS, Co-I instrument equipped with a DB-1 fused silica col- (Z)--Ocimene 1036 t RI, MS, Co-I umn (60 m ¥ 0.25 mm i.d., film thickness 0.25 μm). γ-Terpinene 1051 0.1 RI, MS, Co-I The oven temperature was raised from 60 ∞Cto cis-Sabinene hydrate 1057 t RI, MS p-Mentha-3,8-diene 1061 t RI, MS 250 ∞C at a rate of 5 ∞C/min, and then held at Terpinolene 1081 0.1 RI, MS, Co-I 250 ∞C for 10 min; transfer line temperature was 1-Octen-3-yl acetate 1090 t MS 250 ∞C. The quadrupole mass spectrum was Menthone 1142 0.5 RI, MS scanned over the 45Ð465 amu with an ionizing iso-Menthone 1154 11.9 RI, MS iso-Isopulegol 1159 0.7 RI, MS voltage of 70 eV and an ionization current of Terpinen-4-ol 1168 0.6 RI, MS 150 μA. neo-Menthol 1177 t RI, MS The constituents of the oil were identified by neoiso-Menthol 1198 0.3 RI, MS calculation of their retention indices under tem- Pulegone 1238 65.2 RI, MS, Co-I perature-programmed conditions on a DB-1 col- Piperitone 1249 0.6 RI, MS Carvone 1255 t RI, MS, Co-I umn for n-alkanes (C6ÐC24) and the oil under the Bornyl acetate 1277 0.1 RI, MS same conditions. Identification of individual com- Carvacrol 1282 0.1 RI, MS, Co-I pounds was made by comparison of their mass Piperitenone 1328 6.5 RI,MS spectra with those of the internal reference mass -Bourbonene 1390 0.1 RI, MS, Co-I Germacrene-D 1484 0.3 RI, MS spectra library (Wiley 7.0) or with authentic com- Bicyclogermacrene 1498 0.1 RI, MS pounds and confirmed by comparison of their re- Monoterpene hydrocarbons 2.3 tention indices with authentic compounds or with Oxygenated monoterpenes 94.3 those reported in the literature (Adams, 2001; Shi- Sesquiterpene hydrocarbons 0.5 bamoto, 1987). Quantitative data were obtained Total identified 97.1 from FID area percentages without the use of cor- a RI, retention indices relative to C6ÐC24 n-alkanes on rection factors. a DB-1 column; MS, mass spectroscopy; Co-I, co-in- jection with authentic compound. b t, trace (Ͻ 0.1%). A. Sonboli et al. · Antibacterial Activity and Composition of the Oil of Z. clinopodioides 679 1,8-cineole and pulegone) were applied on the pa- 1991; Dembistikii et al., 1995; Meral et al., 2002). per discs (the disc diameter was 6 mm). Then disc Compared to other Ziziphora species, the pule- papers were placed in the inoculated plates. After gone content of the essential oil of Z. clinopodi- 24 h of incubation at 37 ∞C the diameters of inhibi- oides subsp. bungeana (65.2%) was lower than that tion zones were measured. of Z. tenuior (87.1%) (Sezik et al., 1991), Z. taurica For the determination of MIC (minimum inhibi- subsp. clenioides (81.9%) (Meral et al., 2002), Z. tory concentration) values, a microdilution broth persica (66.0%) and higher than that of Z. vychod- susceptibility assay was used as recommended by ceviana (57.5%) (Dembistikii et al., 1995). Piperi- NCCLS (1999). A standard reference antibiotic tenone (6.5%) as another major oil component of (ampicillin) was used as positive control. All ex- Z. clinopodioides subsp. bungeana was also found periments were performed in triplicate. in the oil of Z. taurica subsp. clenioides (2.3%). Results and Discussion Antibacterial activity Essential oil analysis As shown in Table II the results obtained from The essential oil obtained from hydrodistillition the disc diffusion method followed by the meas- of the aerial flowering parts of Z. clinopodioides urement of MIC values indicated that S. epidermi- subsp. bungeana yielded 1.0% [(w/w) based on the dis, B.
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