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Journal of Essential Oil Bearing Plants
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Chemical Composition of the leaves extract of Warionia saharae of Morocco
A. Essaqui a , A. Elamrani a , M. Benaissa a , A. I. Rodrigues b & L. Yoongho c
a Departement de chimie, Faculte des Sciences, Universite Hassan II Ain Chock, Ain Chock, B.P. 5366, Maarif, Casablanca, Marocco
b Departamento das Tecnologias das Industrias Quimicas, Instituto Nacional de Engenharia e Tecnologia Industrial, Estrada do Paco do Lumair, 1649-038, Lisboa, Portugal
c Department of Applied Biology and Chemistry, Bio/Molecular Informatics Center, Konkuk University, Seoul, South Korea
Published online: 12 Mar 2013.
To cite this article: A. Essaqui , A. Elamrani , M. Benaissa , A. I. Rodrigues & L. Yoongho (2004) Chemical Composition of the leaves extract of Warionia saharae of Morocco, Journal of Essential Oil Bearing Plants, 7:3, 250-254, DOI:
10.1080/0972-060X.2004.10643402
To link to this article: http://dx.doi.org/10.1080/0972-060X.2004.10643402
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Chemical Composition of the leaves extract of Warionia saharae of Morocco
Essaqui, A1., Elamrani, A*1., Benaissa, M1., Rodrigues, A. I.2., Yoongho, L3.
1Universite Hassan II Ain Chock, Departement de chimie, Faculte des Sciences Ain Chock, B.P. 5366, Maarif, Casablanca, Marocco.
2Departamento das Tecnologias das Industrias Quimicas, Instituto Nacional de Engenharia e Tecnologia Industrial, Estrada do Paco do Lumair, 1649-038 Lisboa, Portugal.
3Department of Applied Biology and Chemistry, Bio/Molecular Informatics Center, Konkuk University, Seoul, South Korea.
Abstract: Air-dried aerial parts of wild Warionia saharae were collected in Guelmim region (south of Morocco) during April 2003. The leaves only, were extracted with hexane in a Soxhlet apparatus for 8h. The obtained hexane extract was fractionated on the silica gel column and analyzed by GC and GC-MS using MS and retention index data. A total of 29 constituents were identified. The major components of the extract were hexadecanoic acid (17.8%), ethenyloxy-1-ocatdecane (9.5%), tridecene (7.3%), eicosene-9 (6.7%), octadecanoic acid (6.7%), (E)-2-decenol, (6.7%), eicosene-3 (5.1%) and eicosane (4.5%).
Key words: Warionia saharae, Compositae, Soxhlet apparatus, Leaves extract composition, hexadecanoic acid.
Introduction: In 1872 Bentham and Cosson1 considered that Warionia is a monotypique genus of the family Compositae with the unique species saharae because of its geographical localization. They reported that Warionia saharae is characterized by a descerning odor. A few year lated, Bentham and Hooker2 sequenced Warionia saharae among the Cynaroideaes, but Bonnet and Maury3 study in depth this species and put back in question its adherence to cynaroideaes.
Warionia saharae was reported for the first time in the Oranais sahara (Beni ounif in Algeria) by Dr. Warrion as a shrub upto 3m height. The thick trunk, is covered of a gray ISSN 0972-060X
*Corresponding author (Elamrani, A) e-mail: < aelamrani77@yahoo.fr>
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peel, structural of very wavy terminal leaf bouquets, and of capitulate of yellow flowers. The picking of stems leafed of this bush, clear a very heady, spicy odor, at a time fruity and charnelle, the latex that flows out of injuries of the peel, glue to hands in a very tenacious way4.
In Morocco, Warionia saharae is growing wild in various regions in south of the country particularly in Agadir, Ifni, Bouizkarn, Oued Ouarksiz, Aoulouz, Figuig, Erfoud, east of Tiznit, Guelmim and Marrakech5,6. The habitat is between schistose rocks7. In Morocco, Warionia saharae is known under the arabic vernacular names of “afessas”, “afezded”.
The berber name is “Tazart n-ifiss”8. In the traditional medicine of Morocco the leaves of the endemic plant Warionia saharae Benth. & Coss. are used to treat inflammatory dis- ease, such as rheumatoid arthritis, and for gastro-intestinal disorders8.
The chemical composition of Warionia saharae essential oils from the leaves was reported for the first time by Ramaut et al9. The authors have isolated and identified only 3 constituents: eudesmol (42.25%), linalool (8.63%) and nerolidol (17.26%).
Reports concerning the chemical composition of the dichloromethane extract of Warionia saharae leaves have been previously investigated10-13. While studing cytotoxic and anti-inflammatory activity of this plant, twelve new quaianolide type sesquiterpene lac- tones were identified.
The aim of this study was to examine the chemical composition of the Warionia saharae leaf extract because no information was available using soxhlet apparatus extrac- tion method.
Experimental
Plant Material: The samples of Warionia saharae were collected in April 2003 from Guelmim region (at 500 km south of Rabat). The plant material was identified accord- ing to the flora of Morocco14 and also by Pr. M. Rejdali and Pr. A. Achhal, Agronomic Institute and Veterinary Hassan II, Rabat (Morocco). A voucher specimen is deposited in the herbarium of the Department of Botany and Ecology at the Agronomic Institute and Veterinary Hassan II, Rabat (Morocco).
Preparation of the extract: After air-drying in the shade for a week, 1 kg of Warionia saharae was extracted with hexane (2 L) in a Soxhlet apparatus for 8h. The solvent used was of the highest purity available (Merck). The solvent was then evaporated under reduced pressure. The hexane extrat (23g) obtained was light green with a strong odor. The moisture content of the air-dried leaves were determined through drying in oven at 1400C for 4h.
Oil Analysis: 10g of the hexane extract was fractionated using a column chroma- tography (80cm x 2mm) on silica gel column 60, Merck 70-270 mesh ASTM (100 G)15-17. The elution was operated as follow: hexane (150 ml), chloroform (100 ml), isopropanol (100 ml) and methanol (150 ml). 50 fractions were obtained. These fractions were analyzed by Thin- Layer Chromatography (TLC) and 5 main fractions were analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS).
Elamrani, A et al./jeobp 7(3) 2004 pp 250-254 251
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GC: The analysis was carried out using an HP 5980 gas chromatography apparatus equipped with FID and two capillary columns DB-5 and CW20M (25m x 0.25mm, film thickness 0.25µm). Analytical conditions were: injector and detector temperature 240 and 2600C respectively, oven temperature programmed from 50 to 2500C at 40C/min. Isothermal temperature at 2500C for 30 min; carrier gas 1 ml N2/min. Relative concentrations were calculated using peak areas as given by HP 3396A integrator, without correction for re- sponse factors. Retention indexes were obtained by injection of the homologous hydrocar- bons series C
8-C
30 in the same conditions (progrmmed temperature) in two capillary col- umns (DB-5 and Carbowax 20M).
GC-MS: The analysis was done using an HP 5980 Series II gas chromatograph equipped with HP-5 capillary column (25m x 0.25mm, film thickness 0.25µm) and an HP 5772A mass selective detector. Analytical conditions were: injector and detector tempera- ture 240 and 2600C respectively, oven temperature programmed from 50 to 2500C at 40C/
min. then isothermal at 2500C for 10 min; carrier gas 2ml He/min; source 70 eV.
The constituents were identified by the combination of retention index data and mass spectra data using NBS library and other litterature data18,19.
Results and discussion: The yield of the hexane extract obtained from the leaves of Warionia saharae by a Soxhlet apparatus ranged from 2.8 to 4.2 with an average value of 3.5% (g per 100g of dried material).
The chemical composition of the hexane extract was studied. The identified compo- nents and their percentage are given in Table 1. A total of 29 compounds, amounting 90% of the extract, was identified. The major components were hexadecanoic acid (17.8%), ethenyloxy-1-ocatdecane (9.5%), tridecene (7.3%), eicosene-9 (6.7%), octadecanoic acid (6.7%), (E)-2-decenol (6.7%), eicosene-3 (5.1%) and eicosane (4.5%).
Studies on the percentage composition of the different groups of compounds in Warionia saharae extract revealed that the hydrocarbon and oxygenated fractions repre- sented 31.6% and 59% respectively.
It may be concluded from this study that the Moroccan Warionia saharae extract is caracterized by higher percentage of oxygenated components particularly the hexade- canoic acid (17.8%).
References
1. Benthan and Cosson. (1872). Bull. Soc. Bot. Fr. 19, 165.
2. Benthan and Hooker. (1873). Genera Plantarum. 2, 474.
3. Bonnet and Maurry, P. (1889). Etude sur le Warionia saharae. Benth & coss.
Assoc. Fr. Avanc. Sc. Congres de Paris.
4. Lebrun, J. P. (1979). Elements pour un Atlas des plantes vasculaires de I’Afrique seche, 2: 11-12 J.E.M.V.P.T., Bot 6.
5. Benabid, A., Fennane, M. (1994). Connaissance sur la vegetation du Maroc:
phytogeographie, phytosociologie et series de vegetations. Lazaroa 14, 21-97.
6. Benabid, A., Cuzin, F. (1997). Dragon tree populations in Morocco: taxonomical,
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biogeographical, and phytosociological vlues. C.R. Acad Sci. Paris, Life Science.
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8. Bellakhdar, J. (1997). La pharmacopee marocaine traditionnelle, Medecine arabe ancienne et savoirs populaires, Ibis press, p. 208.
9. Rmaut, J.L., Hofimger, M., Dimbi, R., Corvisier, M., Lewalle, J. (1985). Main constituents of the essential oil of Warionia saharae Benth & Coss, Chromatographia.
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10. Hilmi, F., Sticher, O., Heilmann, J. (2002). New Cytotoxic 6,7-cis and 6,7-trans Configurated Guaianolides from Warionia saharae, J. Nat. Prod. 65 (4), 523-526.
11. Hilmi, F., Sticher, O., Heilmann, J. (2003). New cytotoxic sesquiterpene lactones from Warionia saharae. Planta Med. 69(5): 462-464.
12. Hilmi, F. (2002). Cytotoxic and anti-inflammatory sesquiterpene lactones from Warionia saharae, a traditional remedy from Morocco. These de doctorat en sciences naturelles, Institut de Technologie de Zurich.
13. Hilmi, F., Gertsch, J., Bremner, P., Volovic, S., Heinrich, M., Sticher, O., Heilmann, J. (2003). Cytotoxic versus Anti-Inflammatory Effects in HeLa, Jurkat T and Human Peripheral Blood Cells Caused by Guaianolide-Type Sesquiterpene Lactones, Bioorganic and Medicinal Chemistry, 11, 3659-3663.
14. Jahandiz, E. and Maire, R. (1934). Catalogue des plantes du Maroc. Tome III, imprimerie Minerva, Alger, Algerie.
15. Scheffer, J. J. C. and Baerheim Svendsen, A. (1975). J. Chromat. 115: 607.
16. Scheffer, J. J. C., Koedam, A. and Baerheim Svendsen, A. (1976).
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(1977). Chromatographia. 10: 669.
18. Laseve. (1996). Mass Spectra and Retention Indice Data Base. Universite de Quebec a Chicoutoumi (UQAC), Canada.
19. Adams, R.P. (1989). Identification of Essential oils by Ion Trap Mass Spectroscopy.
Eds. Academic Press, Inc. San Diego.
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Table 1: Chemical composition of Moroccon Warionia saharae extract isolated from the leaves using Soxhlet apparatus
Compounds Retention Retention Mode of Percentage
Index IK Index IK identification % (DB-5) (CW 20M)
Ethenyloxy-1, Ocatdecane - - a 9.5
(E)-2-Decenol - 1794 a,c 6.7
Dodecane 1200 1200 a,b,c 0.9
Tridecene 1293 - a,c 7.3
2-Dodecenol - - a 1.6
Cyclododecane - - a 0.4
Tetradecane 1400 1400 a,c 1.8
Pentadecane 1500 1500 a,b,c 0.6
Hexadecene-1 1593 - a,c 1.1
Hexadecane 1601 1600 a,b,c 0.6
Tetradecanol 1676 - a,c 1.0
Heptadecane 1700 1700 a,c 0.4
Pentadecnol 1777 2252 a,c 0.7
Octadecene-1 1795 - a,c 1.1
2,6,6-Trimethyl Bicyclo- - - a 0.9
(3.1.1) heptane
6,10,14-Trimethyl pentadecan-2-one - - a 0.5
Eicosyne-3 - - a 0.4
Hexadecanoic Acid - - a 17.8
(Z)-octadecen-9,oic Acid - - a 3.7
Octadecanoic Acid - - a 6.7
Dotriacontn-1-ol - - a 2.5
5-Ethyl-nonene-1 - - a 0.6
Eicosene-9 - - a 6.7
Eicosene-3 - - a 5.1
2-Heptadecanone 1900 - a 0.4
Phytol 1949 - a,b 4.0
Eicosane 2000 2000 a,c 4.5
Octadecanol 2082 - a,c 0.8
3,7,11-Trimethyl, 2,6,10- - - a 1.8
dodecatrien-1-ol
Oxygenated fraction 59.0
Hydrocarbon fraction 31.6
Total 90.6
a = Comparison of our MS data with NBS75K librairy data.
b = Comparison of our MS data with literature data (Adams).
c = Comparison of our RI data with literature data (Lasseve data base, Chicoutimi Univ, Quebec, Canada).
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