ABSTRACT
The aerial parts of Ziziphora hispanica L. species were collected on April 2011 from Boussaâda localities in Algeria. The chemical compounds of the plant were isolated by hydrodistillation. A total of 28 constituents, representing more than 93.8% of the total oil, were identified by gas chromato-graph/mass spectrometry (GC/MS). The most presented compounds of the essential oil of Z. his-panica were Pulegone (78.6%), limonene, menthofuran, trans-iso-pulegone and piperitenone are rep-resented by low concentrations. The essential oil of aerial parts of Z. hispanica has a broad spectrum of antimicrobial activity. The sensitivity of bacteria and fungi tested with essential oil compounds was found to be very high.
Key words: Ziziphora hispanica L., essential oil, Antibacterial activity, Algeria
INTRODUCTION
Belonging to the family Lamiaceae, Ziziphora hispanica L. is an annual plant with very branchy erect stem. The leaves are all similar, ovate-lanceolate, and ciliate on margins. Spike-like inflorescences composed of verticillastres pauciflores; corolla long tubular structure (Quézel et Santa, 1962-1963). This plant is found in areas of the Saharan Atlas and the highlands. Some of Ziziphora species are used for their aperitif, carminative and antiseptic effects in treatment of various diseases (Ozturk and Ercisli, 2007), especially Z. taurica infusions (Tzakou et al., 2001; Gözde et al., 2006). Z. persica is an edible medicinal plant, it is frequently used as wild vegetable or additive in foods to offer aroma and flavour (Nezhadali et al., 2008, 2009, 2010). Z. clinopodioides, riche in monoterpene glucosides (Megumi et al., 2012), is used mostly in food and medicine (Maya, 2012). Z. hispanica is used as a substitute for Morocco pennyroyal (Mentha pulegium) (Bellakhdar, 1997). According to the population of Boussaâda Z. hispanica is used as an infusion to soothe the stomach pains, for the heart fatigue and added to the coffee for a better taste.
A literature survey showed that the oil of Ziziphora species has been found to be rich in pulegone. The major components in Z. taurica, Z. vychodceviana and Z. persica are pulegone and isomenthone (Dembistikii et al., 1995; Sezik and Tumen, 1990; Nezhadali and Zarrabi, 2010). The major constituent found in the oil of Z. tenuior L. has been reported to be pulegone (Sezik et al., 1991). The chemical composition of Z. clinopodioides Lam. was analyzed, the major constituents were pulegone and piperitenone (Salehi et al., 2005; Sonbola et al., 2006; Verdian-Rizi, 2008; Xing et al., 2010; Soltani, 2012). The essential oil of Turkish Z. taurica subsp. clenioides was found to contain pulegone (Meral et al., 2002). The major constituents of essential of Z. pamiroalaica were pulegone and menthone (Xing et al., 2010). Z. capitata contained no oil; Z. persica, Z. taurica, Z. Tenuior and Z. clinopodioide have a Pulegone as a major compound while Z persica has a major component the thymol (Hüsnü, 2002). The oil of Z. hispanica is characterised by pulegone (Velasco and Mata, 1986; Bellakhdar, 1997; Bekhechi et al., 2007).
The essential oil of Ziziphora species has a broad spectrum of antimicrobial activity. The oil of Z. clinopodioides was found to exhibit interesting antibacterial activity against Staphylococcus epidermidis, S. aureus, Escherichia coli and Bacillus subtilis (Sonbola et al., 2006), the oil of Z. clinopodioides was tested against some human pathogenic bacteria, which showed good activity against all tested bacteria, except for Pseudomonas aeruginosa (Soltani, 2012). Investigation of the antimicrobial activity of the essential oil of the Turkish endemic Ziziphora taurica on eight bacterial strains and Candida albicans, indicate that the essential oil remarkably inhibited the growth of tested microorganisms except Candida albicans (Gozde et al., 2006). Z. tenuior oils had bactericidal and inhibitory effects of K. pneumoniae, It can be used as candidates for treatment of infectious diseases that is caused by this bacteria (Mahboubi et al., 2012). The oil from Z. pamiroalaica was better than that from Z. clinopodioides in antioxidant abilities (Xing et al., 2010). The insecticidal and ovicidal effects of essential oil of Z. clinopodioides were tested on adults and eggs of Callosobruchus maculatus (Lolestani and Shayesteh, 2009). The objective of this research is to determine the chemical composition of essential oil of Z. hipanica from the Boussaada region and evaluate its potential to be antimicrobial.
MATERIALS AND METHODS
Plant material
Aerial parts of Ziziphora hispanica were collected during the flowering stage in October 2011 from Boussaâda localities in Algeria. Identified by Dr. Lograda Takia, the voucher specimen is deposited in the herbarium of the Department of Biology, Ferhat Abbas University, Algeria. Z. hispanica was submitted to hydrodistillation for 3h using a Clevenger apparatus (Lograda et al., 2013). The distilled essential oils were stored at +4 °C for further use.
Essential oil Analysis:
The essential oils were analysed on a Hewlett-Packard gas chromatograph Model 5890, coupled to a Hewlett-Packard model 5971, equipped with a DB5 MS column (30 m X 0.25 mm; 0.25 ìm), programming from 50°C (5 min) to 300°C at 5°C/min, with a 5 min hold. Helium was used as the carrier gas (1.0 mL/min); injection in split mode (1:30); injector and detector temperatures, 250 and 280°C, respectively. The mass spectrometer worked in EI mode at 70 eV; electron multiplier, 2500 V; ion source temperature, 180°C; MS data were acquired in the scan mode in the m/z range 33-450. The identification of the components was based on comparison of their mass spectra with those of NIST mass spectral library (Masada, 1976; NIST, 2002) and those described by (Adams, 2001) as well as on comparison of their retention indices either with those of authentic compounds or with literature values (Adams, 2001).
Antibacterial activity:
Two Gram positive bacteria (Staphylococ-cus aureus ATCC25923 and Bacillus subtilis ATCC 6633) and seven Gram negative bacteria (Pseudomonas aeruginosa ATCC27853, Pseu-domonas syringae pv. Tomato ATCC 1086; Escherichia coli ATCC 25922, klebsiella pneumoniae CIP 53-153, Salmonella enterica CIP 60-62T, Enterobacter sp. and Citrobacter sp.) and three fungi (Aspergelus flavus LBVM20, Aspergilus niger LBBM62 and Candida albicans ATCC 24433) were used in this study. The bacterial inoculums was pre-pared from overnight broth culture in physio-logical saline (0.8 % of NaCl) in order to obtain an optical density ranging from 0.08-01 at 625 nm. Muller-Hinton agar (MH agar) and MH agar supplemented with 5% sheep blood for fastidious bacteria were poured in Petri dishes, solidified and surface dried before inoculation. Sterile discs (6 mm Ö) were placed on inocu-lated agars, by test bacteria, filled with 10 ìl of mother solution and diluted essential oil (1:1, 1:2, 1:5, and 1:10 v:v of Dimethylsulfoxide (DMSO). DMSO was used as negative control. Chloramphenicol for bacteria and amphotericin B for fungi were used as positive control. Bac-terial growth inhibition was determined as the diameter of the inhibition zones around the discs. All tests were performed in triplicate. Then, Petri dishes were incubated at 37°C dur-ing 18-24 h aerobically (Bacteria) and at 25°C for 7 days (fungi). After incubation, inhibition zone diameters were measured and docu-mented.
RESULTS
The essential oil, of Ziziphora hispanica L., isolated by hydrodistillation from the aerial parts, was obtained in yield of 1.01% (v/w). The chemical composition of essential oil, ana-lyzed by gas chromatography/mass spectrome-try (GC-MS), gave 28 constituents representing 93.82% of the total oil. The names of the corre-sponding compounds and their percentages are listed in table 1.
The oil is characterized by a high content of pulegone (78.6%). Other compounds a low rate were piperitenone (2.9%), 8-hydroxy-p-menthan-3-one (2.24%), menthofurane (1.26%), trans-isopulegone (1.09%) and limo-nene (1.4%). The analysis of Z. hispanica es-sential oil revealed the presence of a high per-centage of ketone monoterpene with the pule-gone (78.6%) its dominant compound. The ketone (3.33%) represents the second class of chemical oil, followed by the terpene oxide (1.31%). The monoterpene with 7 compounds, represent 2.37% of total oil with limonene as major compound, unlike sesquiterpene (0.65%), alkene (0.3%), Ether (0.98%) and monoterpene alcohol are poorly represented (Table 2).
DISCUSSION
The result of this research is in accordance with other earlier studies on Ziziphora species that are all found to be rich in pulegone and the review of the published literatures reveal that the composition of Ziziphora species oil shows large similarity in the major components, but relative concentrations have some difference (Gözde et al., 2006; Sonboli et al., 2006; Ozturk and Ercisli, 2006, 2007; Aghajani et al., 2008; Amiri, 2009; Maya, 2011; Ozturk et al., 2007 and Soltani, 2012).
The previous studies showed that Pulegone and Limonene are anti-bacterial (Maya, 2011). The results in this study are consistent with the other antibacterial study results of Ziziphora species and other pulegone rich plants. However, it has been reported that the essential oils of pulegone rich plants such as Micromeria silicica and Mentha suaveolens inhibited Candida albicans (Gözde et al., 2006).
The essential oil of Z. clinopodioides showed good activity against all test bacteria (Soltani, 2012). The antibacterial activity of the oil may be associated with the relatively high pulegone, piperitenone and 1- 8-cineole content. It has been reported that these components have significant antimicrobial activities (Sezik et al., 1991; Meral et al., 2002; Bakkali and Averbeck, 2008; Sonboli et al., 2006).
CONCLUSION
In conclusion, the essential oil of the aerial parts of Z. Hispanica, remarkably inhibited the growth of all tested gram positive and gram negative bacteria and the fungus tested. The essential oil with a composition of pulegone (77.35%), piperitenone (2.90%) and limonene (1.06%) and its observed antibacterial properties show that the essential oil could be evaluated in the pharmaceutical industry as a possible new pulegone resource.
ACKNOWLEDGEMENTS
This work was supported in part by the Laboratory of the Chemistry of Heterocycles, Blaise Pascal University (France) and MESRS of Algeria.
Cite this article:
Bounar R, Takia L, Messaoud R, Pierre C and Gilles F (2013), CHEMICAL COMPOSITION AND ANTIBACTERIAL ACTIVITY OF ESSENTIAL OIL OF ZIZIPHORA HISPANICA L., Global J Res. Med. Plants & Indigen. Med., Volume 2(2): 73-80
REFERENCES
Adams RP (2001). Identification of essential oil by gas chromatography/quadrupole mass spectroscopy, carol stream, IL. Al-lured Publishing Corporation.
Aghajani Z, Assadian F, Masoudi SH, Chal-abian F, Esmaeili A, Tabatabaei M, Rustaiyan A (2008). Chemical composi-tion and in vitro antibacterial activities of the oil of Ziziphora clinopodioides and Z. capitata from Iran. Chem. Nat. Compd. 44(3): 387-389.
Amiri H (2009). Composition and antioxidant activity of the essential oil and metha-nolic extract of Ziziphora clinopodi-oides Lam in preflowering stage. J. Kerman Univ. Med. Sci. 16(1): 79-86
Bakkali F, Averbeck S (2008). Biological ef-fects of essential oils. Food Chem. Toxicol. 46: 446-475.
Baser K H C, Kurkcuoglu M, Ozek T (1992). The volatile constituents of Ziziphora species growing in Turkey. Doga-Tr. J. Pharmacy 2: 7-16.
Bekhechi C, Bekkara F A, Abdelouahid D E, Liu K, Casanova J, Tomi A (2007). Composition and antibacterial activity of the essential oil of Ziziphora hispanica (L.) from Algeria. J essential Oil Bearing Pl. 10(4): 318-23.
Bellakhdar J (1997). La pharmacopée marocaine traditionnelle. Médecine arabe ancienne et savoirs populaires. Ibis Press. 764p
Carson C F, Riley T V (1995). Antimicrobial activity of the major components of the essential oil of Melaleuca alternifolia. J. Appl. Bacteriol. 78: 264-269.
Dembistikii A D, Bergalier E S, Kyazimer I M (1995). Morphological and phyto-chemical study of Ziziphora tenuior L. Chem. Nat. Compd. 31: 673-675.
Gata-Gonçalves L, Nogueira J M F, Matos O, Sousa R B (2003). Photoactive extracts from Thevetia peruviana with antifungal properties against Cladosporium cucumerinum. J. Photochem. Photobiol. B Biol. 70: 51-54.
Gözde Elgin, Ülkü Karabay Yavaþoðlu, Bintuð Öztürk (2006). Antimicrobial Activity of Endemic Ziziphora taurica subsp. cleonioides (Boiss) P. H. Davis Essen-tial Oil. Acta Pharmaceutica Sciencia. 48: 55-62.
Hüsnü K, Can Bascer (2002). Aromatic biodiversity among the flowering plant taxa of Turkey. Pure Appl. Chem. 74(4): 527-545.
Lograda T, Ramdani M, Kiram A, Chalard P, Figueredo G (2013). Variation of Essential oils coposition of Pituranthos scoparius in Algeria. Global J Res. Med. Plants & Indigen. Med. 2(1): 1-9.
Lolestani F A, Shayesteh N (2009). Fumigant toxicity of Ziziphora clinopodioides (Boiss.) (lamiaceae) against and Eggs of Callosobruchus maculates (Fab) (Cleoptera: Bruchidae). J. Biological Sciences. 9(1): 92-95.
Mahboubi Mohaddese, Saeed Bokaee, Hoda Dehdashti, Mohammad Mehdi Feizabadi (2012). Antimicrobial activity of Mentha piperitae, Zhumeria majdae, Ziziphora tenuior oils on ESBLs producing isolates of Klebsiella pneumoniae, Biharean Biologist. 6(1): 5-9.
Masada Y (1976). Analysis of essential oils by Gas chromatography and Mass spectrometry, Halsted, Nueva York, 334p.
Maya Beikmohammadi (2011). The Evaluation of Medicinal Properties of Ziziphora clinopodioides, World Applied Sciences Journal. 12(9): 1635-1638.
Megumi Furukawa, Naoki Oikawa, Toru Imo-hata, Mitsuko Makino, Shoujiro Ogawa, Takashi Iida, Yasuo Fujimoto, Susumu Kitanaka (2012). Monoterpene Gluco-sides from Ziziphora clinopodioides (Labiatae). Chem. Pharm. Bull. 60(3): 397-401.
Meral G E, Konyalioglu S, Ozturk B (2002). Essential oil composition and antioxi-dant activity of endemic Ziziphora taurica subsp. Cleonioides. Fi-toterapia.73: 716-718.
Nezhadali A, Zarrabi Shirvan B (2010). Sepa-ration, Identification and Determination of Volatile Compounds of Ziziphora persica Bunge Using HS-SPME/GC-MS. International Journal of Environ-mental Science and Development. 1(2): 115-118.
Nezhadali A, Akbarpour M, Zarrabi Shirvan B (2008). Chemical composition of the essential oil from the aerial parts of Ar-temisia herba alba, E-J. Chemistry. 5: 557-561.
Nezhadali A, Khazaeifar A, Akbarpour M, Masrournia M (2010). Chemical com-position of essential oil and antibacterial activity of Dracocephalum subcapi-tatum, J. Essent. Oil. Bearing Plan. 13: 112-117.
Nezhadali A, Soleymani Roudi B, Akbarpour M (2009). Chemical composition of the essential oils from the flower of Tanacetum Polycephalum Subsp. Dud-eranum as a herbal plant in Iran. Der Pharma Chemica. 1: 27-31.
NIST (2002). Mass spectral search program for the NIST/EPA/NIH Mass spectral Li-brary. Vers.2.0. Fireash data, USA.
Ozturk S, Ercisli S (2006). The chemical composition of essential oil and in vitro antibacterial activities of essential oil and methanol extract of Ziziphora persica Bunge. J. Ethnopharmacol. 106: 372-376.
Ozturk S, Ercisli S (2007). Antibacterial activity and chemical constitutions of Ziziphora clinopodioides. Food control. 18(5): 535-540.
Ozturk Y, Aydin S, Tecik B, Baser K H C (1995). Effects of essential oils from Ziziphora species on swimming per-formance in mice. Phytother. Res. 9: 225-227.
Quézel P, Santa S (1962-1963). Nouvelle flore de l'Algérie et des régions désertiques méridionales. Ed. C.N.R.S., Paris, 2 tomes.
Salehi P, Sonboli A, Eftekhar F, Nejad-Ebrahimi S, Yousefzadi M (2005). Essential oil composition, antibacterial and antioxidant activity of the oil and various extracts of Ziziphora clinopodioides subsp. rigida (Boiss.). Biol. Pharm. Bull. 28(10): 1892-1896.
Sezik E, Gülendam Tümen (1990). Constituents of the essential oil Ziziphora taurica Subsp. Celonioids (Boiss) P.H. Davis growing in Turkey. Journal of Islamic Academy of Sciences. 3(2): 113-117.
Sezik E, Tumen G, Baser K H C (1991). Ziziphora tenuior L. a new source of pulegone. Flav. Fragr. J. 6: 101-104.
Soltani Nejad Shahla (2012). Chemical composition and in vitro antibacterial activity of Ziziphora clinopodioides Lam. essential oil against some pathogenic bacteria, African Journal of Microbiology Research. 6(7): 1504-1508.
Sonboli Ali, Mohammad Hossein Mirjalili, Javad Hadian, Samad Nejad Ebrahimi, Morteza Yousefzadie (2006). Antibacterial Activity and Composition of the Essential Oil of Ziziphora clinopodioides subsp. bungeana (Juz.) Rech. f. from Iran., Z. Naturforsch. 61(c): 677-680.
Tzakou O, Pitarokili D, Chinou I B, Harvala C (2001). Composition and antimicrobial activity of the essential oil of Salvia ringens. Planta Med. 67(1): 81-83.
Velasco Negueruela A, Mata Rico M (1986). The volatile oil of Ziziphora hispanica L. Flavour and Fragrance Journal. 1(3): 111-113.
Verdian-Rizi Mohammadreza (2008). Essential oil composition and biological activity of Ziziphora clinopodioides Lam. From Iran. Research Journal of Pharmacology, 2(2): 17-19.
Xing Si-lei, Zhang Pi-hong, Ji Qiao-ling, Jia Hong-li, Wang Xue-hua (2010). Essential Oil Compositions and Antioxidant Activities of Two Ziziphora Species in Xinjiang. Food Sciences. 31(7): 154.159.
Source of Support: Nil
Conflict of Interest: None Declared
Bounar Rabah1, 6, Takia Lograda2*, Messaoud Ramdani3, Pierre Chalard4 and
Gilles Feguiredo5
1, 2, 3Laboratory of Natural Resource Valorization, Sciences Faculty, Ferhat Abbas University, 19000 Setif, Algeria
4Clermont Université, Université Blaise Pascal, BP 10448, F-63000 Clermont Ferrand
5LEXVA Analytique, 460 rue du Montant, 63110 Beaumont, France
6Department of Natural Sciences and Life, Faculty of Science, M'sila University, 28000 M'sila (Algeria)
*Corresponding Author : [email protected]; +21336835894, +213 776243824; Fax : +21336937943
Received: 24/12/2012; Revised: 25/01/2013; Accepted: 31/01/2013
You have requested "on-the-fly" machine translation of selected content from our databases. This functionality is provided solely for your convenience and is in no way intended to replace human translation. Show full disclaimer
Neither ProQuest nor its licensors make any representations or warranties with respect to the translations. The translations are automatically generated "AS IS" and "AS AVAILABLE" and are not retained in our systems. PROQUEST AND ITS LICENSORS SPECIFICALLY DISCLAIM ANY AND ALL EXPRESS OR IMPLIED WARRANTIES, INCLUDING WITHOUT LIMITATION, ANY WARRANTIES FOR AVAILABILITY, ACCURACY, TIMELINESS, COMPLETENESS, NON-INFRINGMENT, MERCHANTABILITY OR FITNESS FOR A PARTICULAR PURPOSE. Your use of the translations is subject to all use restrictions contained in your Electronic Products License Agreement and by using the translation functionality you agree to forgo any and all claims against ProQuest or its licensors for your use of the translation functionality and any output derived there from. Hide full disclaimer
Copyright Global Journal of Research on Medicinal Plants & Indigenous Medicine (GJRMI) Feb 2013
Abstract
The aerial parts of Ziziphora hispanica L. species were collected on April 2011 from Boussaâda localities in Algeria. The chemical compounds of the plant were isolated by hydrodistillation. A total of 28 constituents, representing more than 93.8% of the total oil, were identified by gas chromato-graph/mass spectrometry (GC/MS). The most presented compounds of the essential oil of Z. his-panica were Pulegone (78.6%), limonene, menthofuran, trans-iso-pulegone and piperitenone are rep-resented by low concentrations. The essential oil of aerial parts of Z. hispanica has a broad spectrum of antimicrobial activity. The sensitivity of bacteria and fungi tested with essential oil compounds was found to be very high. [PUBLICATION ABSTRACT]
You have requested "on-the-fly" machine translation of selected content from our databases. This functionality is provided solely for your convenience and is in no way intended to replace human translation. Show full disclaimer
Neither ProQuest nor its licensors make any representations or warranties with respect to the translations. The translations are automatically generated "AS IS" and "AS AVAILABLE" and are not retained in our systems. PROQUEST AND ITS LICENSORS SPECIFICALLY DISCLAIM ANY AND ALL EXPRESS OR IMPLIED WARRANTIES, INCLUDING WITHOUT LIMITATION, ANY WARRANTIES FOR AVAILABILITY, ACCURACY, TIMELINESS, COMPLETENESS, NON-INFRINGMENT, MERCHANTABILITY OR FITNESS FOR A PARTICULAR PURPOSE. Your use of the translations is subject to all use restrictions contained in your Electronic Products License Agreement and by using the translation functionality you agree to forgo any and all claims against ProQuest or its licensors for your use of the translation functionality and any output derived there from. Hide full disclaimer




