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Chemical Composition of the leaves extract of Warionia

saharae of Morocco
a a a b c
A. Essaqui , A. Elamrani , M. Benaissa , A. I. Rodrigues & L. Yoongho
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

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 jeobp 7(3) 2004 pp 250-254 250

ISSN 0972-060X

Chemical Composition of the leaves extract of Warionia saharae of Morocco

Essaqui, A1., Elamrani, A*1., Benaissa, M1., Rodrigues, A. I.2., Yoongho, L3.

1
Universite Hassan II Ain Chock, Departement de chimie, Faculte des Sciences
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Ain Chock, B.P. 5366, Maarif, Casablanca, Marocco.

2
Departamento das Tecnologias das Industrias Quimicas, Instituto Nacional de Engenharia e
Tecnologia Industrial, Estrada do Paco do Lumair, 1649-038 Lisboa, Portugal.

3
Department 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 Cosson 1 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

*Corresponding author (Elamrani, A)

e-mail: < aelamrani77@yahoo.fr>
 Elamrani, A et al./jeobp 7(3) 2004 pp 250-254 251

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
way 4.
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
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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 250-254 252

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 C8-C30 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-
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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.
320, 267-277.
7. Medail, F. and Quezel, P. (1999). The phytogeographical significance of South
West Morocco compared to the Canary Islands. Plant Ecology, 140, 221-244.
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.
20, p. 193.
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.
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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).
Chromatographia. 9: 425.
17. Scheffer, J. J. C., Koedam, A., Schusler, M., Th. I. W. and Baerheim Svendsen , A.
(1977). Chromatographia. 10: 669.
18. Laseve. (1996). Mass Spectra and Retention Indice Data Base. Universite de
Quebec a Chicoutoumi (UQAC), Canada.
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Eds. Academic Press, Inc. San Diego.
 Elamrani, A et al./jeobp 7(3) 2004 pp 250-254 254

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
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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).