Int. J. Med. Arom. Plants, ISSN 2249 – 4340

RESEARCH ARTICLE

Vol. 2, No. 4, pp. 632-637, December 2012

Essential oil and antibacterial activity of Senecio perralderianus T. LOGRADA1, M. RAMDANI1, P. CHALARD2, R. GHARZOULI1, G. FEGUIREDO3, J.C. CHALCHAT2 1

Laboratory of Natural Resource Valorization, Sciences Faculty, Ferhat Abbas University, 19000 Setif, Algeria 2

Ecole nationale Supérieure de Chimie de Clermont Ferrand, Laboratoire de Chimie des Hétérocycles et des glucides, EA987, 63174 Aubière Cedex 01. 3

LEXVA Analytique, 460 rue du Montant, 63110 Beaumont, France

*Corresponding Author, Tel: +213 36 83 58 94, Fax: +213 36 93 79 43, Mob. +213 776243824. Article History: Received 25th October 2012, Revised 23rd December 2012, Accepted 24th December 2012. Abstract: The analysis and identification of essential oils hydrodistilated from one species (Senecio perralderianus Cos. & Dur.), by means of gas chromatography and mass spectroscopy, was realized in this investigation. A low yield (0.1%) for S. perralderianus was obtained. From the leaf essential oil 50 compounds were separated and elucidated, representing 96.9% of the total essential oil mass. The major compound was γ-cadinene (15.3%), other components present in appreciable contents were: α-pinene (8.8%), germacrene-D (5.8%), β-caryophyllene (5.5%), γ-eudismol (4.9%), γ-muurolene (4.2%), trans-β-farnesene (3.8%), β-pinene (3.5%) and β-cubebene (3.3%). 16 other components have a significant concentration, which is between 1 and 2.7%. The effects of these oils on the growth of Escherichia coli (ATCC 25922), Pseydomonas aeruginosa (ATCC 27853) and Staphylococcus aureus (ATCC 25923) were investigated by the diffusion method. The oils showed a low antibacterial activity. Keywords: Senecio perralderianus; Asteraceae; Essential oil; Aantibacterial activity; Algeria.

Introduction The genus Senecio L. (Asteraceae) is represented by 18 species in Algeria, six are endemic (Quézel et Santa 1963). Senecio perralderianus Coss. & Dur. synonym S. atlanticus Coss. B. no & R., is an endemic species, grows in high mountains, perennial 20 to 50 cm long, arachnoid at the low and glabrous in top. The leaves are tender, cordate-orbicular toothed. The flower heads are large and yellow. Some species of Senecio are used in traditional Chinese medicine for treat ophthalmic diseases, inflammation, and leptospirosis (Chen et al. 2009). Senecio perralderianus, in traditional medicine, according to the local population; is used for treatment of asthma, coughs and bronchitis. The volatile constituents of S. glaucus subsp. coronopifloius include myrcene and dehydrofukinone as main components (Vera et al. 1994), while sabinene, α-phellandrene, ger-

macrene-D and β-caryophyllene are the main components in essential oil of S. leucostachys (Vera et al. 1994; Fernández-Zúñiga et al. 1996; Nori-Shargh et al. 2008). The α-terpinene, pcymene, terpinene-4-ol and α-phellandrene are the major components of the essential oil of S. graveolens (Perez et al. 1999). The main component of the oil of S. aegyptius var. discoideus is the 1,10-epoxyfuranoeremophilane (ElSharzly 2002). The essential oils of aerial parts of S. nutans showed the predominance of monoterpene hydrocarbon (Feo et al. 2003). Previous works on the chemical composition on essential oils of some Senecio have shown that p-cymene and α-phellandrene are the major constituents of the oil of S. squalidus (Chalchat et al. 2004). In the essential oil obtained from flowers of S. farfarifolius, the α-pinene and 1,8cineole were found as main compounds (Baser and Demirci 2004). The monoterpene of the essential oils from the flowers of S. scandens rep-

*Corresponding author: (E-mail) ramdani_ghalia yahoo.fr http://www.openaccessscience.com © 2012 Copyright by the Authors, licensee Open Access Science Research Publisher. [email protected] This is an open access article distributed under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported (CC BY-NCND 3.0) License (http://creativecommons.org/licenses/by-nc-nd/3.0)

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resent 42.75% with dominance of the α-pinene (Chen et al. 2009). The major constituents of the essential oil of S. longipenicillatus are α-pinene, α-humulene and germacrene-D (Rondon et al. 2006). (E)-β-farnesene is the major compound in oil of S. trapezuntinus (Osman et al. 2008). The main compound of the essential oil of S. coincyi was the 1-tridecene (Arrabal et al. 2011). Spathulenol, 1,8-cineole, m-cymene, isobicyclogermacrenal and α-phellandrene were the major constituents in the essential oil of S. vernalis from Iran (Nori-Shargh et al. 2008), while the main components of the oil of S. vernalis grown in Turkey are α-pinene and βpinene, Δ3-carene, germacrene-D, αphellandrene, Z-β-ocimene and α-humulene (Usta et al. 2009). In the essential oil of S. platyphyllus var. platyphyllus, E-caryophyllene, germacrene-D and E-α-farnesene were the main compounds (Usta et al. 2009). The chemical composition of the essential oils obtained from fresh parts of Senecio pandurifolius were αcuprenene, borneol, β-eudesmol, 1-undecene, (E)-caryophyllene, nonadecane and hexadecane (Kahriman et al. 2011). The major components of S. scandens oils are β-pinene (32.89%), benzaldehyde (15.13%), β-caryophyllene (10.07%) (Chen et al. 2009). The chemical profile of Senecio polyanthemoides reveals the dominance of monoterpenoid compounds, the main constituents of the oils were limonene, p-cymene, βselinene, α-pinene, β-pinene (Lawal et al. 2009). S. mustersii rich in α-pinene, β-pinene by cons in S. subpanduratus is added sabinene and pcymene (Luz et al. 2010). Furthermore, biological activities such as antibacterial (El-Shazly et al. 2002), antimicrobial (Perez et al. 1999) and cytotoxic activities (Rondon et al. 2006). The antimicrobial activity of the essential oil of S. graveolens has provided antibacterial effect on Micrococcus luteus, and Staphylococcus aureus, as well as antifungal effects on Candida albicans (Perez et al. 1999). The essential oil of S. longipenicillatus has shown a strong antibacterial activity against S. aureus and Enterococcus faecalis (Rondon et al. 2006). The essential oils of S. pandurifolius showed antibacterial activity (Kahriman et al. 2011). Senecio mustersii shows activity against S. aureus and showed no antifungal activity while Senecio subpanduratus shows activity Lograda et al.

633 Essential oil and antibacterial activity of S. perralderianus

against all bacteria tested and was active against Candida species (Luz et al. 2010). To the best of our knowledge, there are no reports on the essential oil profile of Senecio perralderianus growing in Algeria. Therefore, this paper reports for the first time the chemical composition of the essential oils and antimicrobial activities of these parts of Senecio perralderianus. This study aimed to investigates the chemical composition and antibacterial activity of essential oils of Senecio perralderianus. Materials and methods Plant material The aerial parts of Senecio perralderianus were collected from the Takoucht Mountain (Algeria) during flowering season 2010 in their natural habitat. Plant materials were taxonomically identified by Dr. Lograda T., a voucher specimen is deposited in the Herbarium of the Sciences Faculty of Ferhat Abbas University (Algeria). Leaves and flowers were dried at room temperature for 7 days, and used for analyses. The study is based on the analysis of a random sample. Essential oil analysis The essential oils were extracted by hydrodistillation of dried plant material using a Clevenger-type apparatus for 3 h. The oils were stored in sealed glass vials at 4-5°C prior to analysis. Yield based on dry weight of the sample was calculated. The essential oil were analysed on a Hewlett-Packard gas chromatograph Model 5890, coupled to a Hewlett-Packard MS model 5871, equipped with a DB5 MS column (30m X 0.25mm; 0.25μm), programming from 50°C (5 min) to 300°C at 5°C/mn, 5 min hold. Helium as carrier gas (1,0ml/min); injection in split mode (1: 30); injector and detector temperature, 250 and 280°C respectively. The MS working in electron impact mode at 70 eV; electron multiplier, 2500V; ion source temperature, 180°C; mass spectra data were acquired in the scan mode in m/z range 33-450.

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The compounds assayed by GC in the different essential oils were identified by comparing their retention indices with those of reference compounds in the literature and confirmed by GC-MS by comparison of their mass spectra with those of reference substances (Adams 2004; Swigar and Silverstein 1981). Evaluation of the antibacterial activity The antibacterial activity of the oil was carried out by the disc diffusion method, according to the National committee of clinical laboratory standards against three of American type Culture Collection (ATCC) namely: Escherichia coli (ATCC 25922), Pseydomonas aeruginosa (ATCC 27853) and Staphylococcus aureus (ATCC 25923) which were obtained from the Microbiology and Parasitology Laboratory of Frhat Abbas University Hospital. It was performed using a 20 h culture growth at 37°C and adjusted to approximately 105 CFU mL-1. Five hundred microlitres of the bacterial suspension was spread on the surface of Muller-Hinton Agar plates. Sterile filter paper disks (Whatman

634 Essential oil and antibacterial activity of S. perralderianus

N°1.6 mm in diameter) containing 10 µL of each dilution of the oil (Half, ¼ and 1/8 v/v in absolute ethanol) were placed on the surface of the media. The plates were left 30 min at room temperature to allow the diffusion of the oil and then they were incubated at 37°C for 24 h. At the end of this period, the inhibition zones were measured. All the experiments were performed in triplicate. Positive (Gentamycine, 10µg disc1) and negative controls (10 µL ethanol) were also included in the test. Result The yield of S. perralderianus essential oils is low (0.1%) compared to other species of the genus Senecio. The GC-MS analysis of the essential oils of S. perralderianus allowed the identification of 50 compounds. The constituents leaf oils were listed in order of their elution on the non polar column (Figure 1). The retention time and chemical composition of essential oils of Senecio perralderianus are presented in (Table 1).

Figure 1: GC/FID profiles of Senecio perralderianus essential oil (for numbering see Table 1). Lograda et al.

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635 Essential oil and antibacterial activity of S. perralderianus

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Table 1: Composition of essential oil of Senecio perralderianus Coss. & Dur. Compounds α-pinene Sabinene β-pinene Myrcene β-phellandrene Trans-β-ocimene Terpinolene Linalool n-nonanal n-decanal Carvacol methyl ether Lavandulyl acetate Undecanal α-longifolene α-cubebene α-copaene β-maaliene β-cubebene β-caryophellene Trans-β-farnesene α-humulene α-amorphene γ-muurolene Germacrene-D ∆-selinene

KI 937 971 977 988 1030 1047 1089 1097 1103 1204 1222 1285 1306 1350 1351 1376 1383 1387 1420 1445 1457 1478 1581 1483 1490

RT 10.068 11.458 11.63 12.028 13.453 13.959 15.424 15.701 15.862 18.923 19.427 21.056 21.758 22.859 23.603 23.794 23.906 24.753 25.47 25.642 25.744 26.014 26.084 26.266 26.531

% 8.8 2.0 3.5 0.5 2.7 0.2 0.5 0.3 0.2 0.3 0.3 0.8 0.3 0.5 0.8 1.3 2.1 5.5 0.5 3.8 2.4 0.7 4.2 5.8 0.5

Compounds α-muurolene α-farnesene-E-E γ-cadinene Trans-calamenene ∆-cadinene Caryophyllene oxide Gleenol Trans-muurola-4(14),5-diene Humulene epoxide II 1,10-di-epi-cubenol γ-eudesmol Aristolene Epi-α-muurolol α-muurolol α-cadinol 11-methylanthra[2,1-b]furan 2-pentadecanone, 6,10,14-trimethyl 1,10-dehydrofuranoeremophilane 1,2-Benzenedicarboxylic acid, bis Palmitic acid (Hexadecanoic acid) 1,2-Benzenedicarboxylic acid, buty Phenanthrene, 1,2,3,4,4a,9,10,10a Abietadiene Phytol Tricosane

The composition of the essential oil is rich in γ-cadinene (15.3%), α-pinene (8.8%), Dgermacrene (5.8%), β-caryophyllene (5.5%), γeudismol (4.9%), γ-muurolene (4.2%) and 1,10dehydro furanoeremophilane (4.0%). 25 compounds of the essential oil are represented by a concentration greater than 1%.

KI 1497 1503 1517 1522 1523 1584 1586 1593 1610 1623 1632 1635 1644 1647 1656 1774 1836 1853 1949 2053 1955 2086 2102 2293 2494

RT 26,61 26.646 26.728 27.106 27.216 28.012 28.489 28.67 28.732 28.851 29.289 29.678 29.762 29.83 30.023 30.082 30.286 30.509 32.833 34.111 34.455 36.324 36.453 38.288 38.894

% 1.3 0.2 15.3 1.0 1.5 2.3 0.5 0.7 1.0 1.2 4.9 0.8 2.1 1.1 0.7 1.4 0.4 4.0 0.4 0.3 2.3 0.7 2.3 0.4 0.4

cherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853 and Staphylococcus aureus ATCC 25923, but the bacteria tested were resistant to the essential oil concentrations of 1/4 and 1/8. Discussion

Table 2: Antibacterial perralderianus oil in vitro.

activity

of

Senecio

Strains [c] v/v

Inhibition zone (mm) ½ ¼ 1/8 Gen Escherichia coli (ATCC 25922), 20 9 7 32 Pseydomonas aeruginosa (ATCC 27853) 15 8 6 20 Staphylococcus aureus (ATCC 25923) 17 10 7 30

Gen Gentamicine (10 µg disk-1); Inhibition zone (diameter of the disk, 6 mm, include), values represent the average of three determination

Many plant derived essential oils are known to exhibit antimicrobial activity against a wide range of bacteria. The in-vitro antimicrobial activities of the essential oils of Senecio perralderianus, which have not been reported previously, are given in Table 2. The half dilution of the oil decreased the density of growth of EsLograda et al.

The composition of essential oil of S. perralderianus is different from the composition of other species of the genus; the quantitative and qualitative difference is important. The essential-oil of S. perralderianus differs from other species of the genus Senicio by the presence of γ-cadinene. This composition of the essential oil resembles to those of other species by the presence of α-pinene, dominant component in S furfarifolium (Baser and Demirci 2004), by D-germacrene present in S. longipenicillatus (Rondon et al. 2006) and in S. vernalis and S. leucostachys (Usta et al. 2009). The 1.10dehydrofuranoeremophilane, present in S. aegypticus (El-Sharzly 2007), represents 4% of the essential oil in our species. S. perralderianus with 15.3% of γ-cadinene and 8.8% of α-pinene differs from S. scandens with 32.5% of βhttp://www.openaccessscience.com [email protected]

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pinene, and traces of γ-cadinene (Chen et al. 2009). The Senecio Species have significant antibacterial activities, antibacterial (El-Shazly et al. 2002 ; Rondon et al. 2006 ; (Kahriman et al. 2011), antimicrobial (Perez et al. 1999), cytotoxic activities (Rondon et al. 2006) and antifungal activity(Luz et al. 2010), while S. perralderianus has only weak antibacterial activity. Acknowledgement: This work was supported, in part, by the Laboratory of Chemistry and Heterocyclic Carbohydrates of Clermont Ferrand, France and MESRS of Algeria. References Adams, RP. 2004. Identification of essential oil components by Gas Chromatography/Quadrupole Mass Spectroscopy. Allured publishing, Carol Stream, IL, USA.

636 Essential oil and antibacterial activity of S. perralderianus

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