Chemical composition of the essential oil extracted from the leaves of the dwarfish (Chamaerops humilis L.) palm tree of morocco (region of Benslimane)

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Chemical Composition of the Essential Oils of Flowers of Warionia saharae from Morocco

Abdelhak Essaqui ^a & Mohammed Benaissa ^a

a Equipe de Chimie Agroalimentaire et Chimie des substances naturelles végétales et marines, Faculté des Sciences , Université Hassan , II-Casablanca, B.P. 5366 Maarif, Casablanca , Morocco

Published online: 17 Sep 2013.

To cite this article: Abdelhak Essaqui & Mohammed Benaissa (2013) Chemical Composition of the Essential Oils of Flowers of Warionia saharae from Morocco, Journal of Essential Oil Bearing Plants, 16:3, 372-376, DOI: 10.1080/0972060X.2013.813238 To link to this article: http://dx.doi.org/10.1080/0972060X.2013.813238

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Chemical Composition of the Essential Oils of Flowers of Warionia saharae from Morocco Abdelhak Essaqui * and Mohammed Benaissa

Equipe de Chimie Agroalimentaire et Chimie des substances naturelles végétales et marines, Faculté des Sciences, Université Hassan, II-Casablanca, B.P. 5366 Maarif, Casablanca, Morocco

Abstract: The essential oils obtained by steam distillation from the flower of Warionia saharae growing in the South of Morocco have been analysed by GC-MS. A total of 21 constituents were identified. The major oil components were β-eudesmol (29.83 %), (E,E)-farnesyl acetate (12.66 %), linalyl butyrate (5.16 %), isoterpinolene (4.36 %) and guaiol (4.22 %). The yield was 0.35 %.

Key words: Warionia saharae; Essential oil composition, flowers, β-eudesmol, (E,E) farnesyl acetate.

Introduction

Continuing our investigations on chemistry of essential oils from Moroccan aromatic flora, we have analyzed the essential oil of Warionia saharae flower, a plant endemic to northwestern Africa edge of the African Sahara desert, growing in several regions in the south of Morocco ^1-2 (Grand Atlas, Imerghdal, Gontafa; Anti-Atlas, above Ait Baha; Province of Agadir at Oued Noun, Goulimime, above Mogador, Djebel Amsitten, between Marrakech and Tizi n’Test, Tagadirt n’Bour, Valley Imouzzer, Ida-ou-Tanan, between Aït Bifradane and Aït Bauka, Tafraoute, Tazzouguert; Guelmim and Figuig) and Algeria^3-

4 (Béni-Ounif in South of Oran) (Fig.1)⁵. Genus Warionia, with its species W. saharae is known in Morocco by the berber vernacular names of “afessas”⁶. It is shrubs, 0.15-3 m high, the thick trunk, is covered of a gray 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 and spicy odor; the latex that flows out of

injuries of the peel, glue to hands in a very tenacious way ⁷.

The plant is considered to have medicinal properties mainly by its essential oils ⁸. Decoction of dried leaves is used by the Moroccan local people as anti rheumatic and against epileptic crisis ⁹. Crude extracts of the plant showed antibacterial and cytotoxic activities ¹⁰ against a cancer cell line (KB cells).

About the composition of W. saharae extracts, Essaqui et al ¹¹ reported that the leaves hexanoic extract prepared using Soxhlet apparatus, contain hexadecanoïc acid (17.8 %), ethenyloxy-1- octadecane (9.5 %), tridecene (7.3 %), eicosene- 9 (6.7 %), octadecanoïc acid (6.7 %), (E)-2- decenol, (6.7 %), eicosene-3 (5.1 %) and eicosane (4.5%) as main components.

Recently, the same authors ¹², identified thirty components in essential oil of aerial parts of W.

saharae. The major components were β- eudesmol (52.7%), trans-nerolidol (17.4%), linalool (5.1 %), guaiol (2.4 %), terpinen-4-ol (1.4

%) and 1,8-cineole (1.2 %); but there are no

*Corresponding author (Abdelhak Essaqui)

Received 10 July 2012; accepted in revised form 25 October 2012

Downloaded by [Swinburne University of Technology] at 07:01 29 December 2014

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available records about the composition of the flowers essential oil.

In the present work, our objective is to extract the essential oil from the W. saharae flower, growing in Morocco, and examined their chemical composition.

Experimental Plant material

W. saharae flower was collected in March 2012 at the flowering stage, from Chtouka Ait Baha region (Douar Brahim o âmar at 682 Km south of Rabat). In this region, several samples of the whole plant were collected and were mixed to obtain a heterogeneous sample (about 10 Kg). In laboratory, the leaves, flowers, and stems were separated. Two flowers samples (1 Kg each) were washed, air-dried and subjected to steam distillation. The plant material was identified according to the flora of Morocco ¹³ and also by Pr. M. Rejdali, 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) and also in our laboratory at the Chemistry Department at the Science Faculty Ain chock, Casablanca Morocco¹¹.

Isolation of essential oil

Dried vegetal material (100 g) was steam distillated for three hours, using a Clevenger-type apparatus according to the method recommended in the European Pharmacopoeia ¹⁴.The distillate was dried over anhydrous sodium sulfate. In parallel to each distillation we determined the moisture of the air dried flowers: two samples (5 g each) were oven dried (104°C) for 4 h. The oil yields were expressed in dry matter percentage.

Gas chromatography-Mass spectrometry GC-MS analysis was conducted using an Agilent/HP 6890 Series Gas Chromatograph equipped with fused silica capillary column DB- 5MS+5mDG capillary column (5 % phenyl- methylpolysiloxane, J&W Scientific) ( 30 m x 0.25 mm; film thickness 0.25 μm), directly coupled to a selective mass detector (HP 5772A, ionization voltage 70 eV).

The oil injected (Diluted samples: 1/100 v/v, Fig. 1. Distribution map of Warionia saharae L.

Abdelhak Essaqui et al., / TEOP 16 (3) 2013 372 - 376 373

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in n-hexane) was 1.0 μL, with split (1:33), at scan mode. The following conditions were used:

temperature of injector: 240°C; temperature of GC detector: 260°C, programmed column temperature: 50 to 250°C at 4°C/min, then isothermal at 250°C for 10 min, carrier gas:

helium (1 mL/min). Electron impact (EI) ionization MS was used at 70 eV. Mass spectra were acquired over a range of 29-400 amu, at 1 scan/s.

The retention indices for all volatile constituents were determined by co-injection of the hydrocarbon standards and the equation of Van Den Dool & Kratz ¹⁵ was used to calculate them.

Gas chromatography

The analysis of the volatile components was carried out an Agilent/HP 6890 Series Gas Chromatograph equipment under the same conditions described before. The GC system was

equipped with a flame ionization detector (FID).

The percentage compositions were obtained through the electronic integration of the GC peak areas without taking into account their relative response factors.

The constituent’s identification and the comparison of their MS data with external standard data were based on the spectrometry library of the equipment system (NIST 2005, Lib.)¹⁶, retention indices (RI)¹⁷ and literature data.

Results are reported in Table 1.

Results and discussion

The oil isolated by steam distillation from the flowers of W. saharae, was found with a strong aromatic odor and yield 0.35 % m/m compared to the dry weight of the plant material. Twenty- one components amounting 81.51 % of the total oil, were identified and are listed in Table 1 according to their retention indices on DB5 - MS columns.

Table 1. Chemical composition of essential oil from the flower of Moroccan W. saharae

Compounds RI^a Percentage %

Monoterpene hydrocarbons

4-Carene 1001 0.58

p-Cymene 1025 0.96

m-Cymene 1082 0.43

Isoterpinolene 1083 4.36

Oxygenated monoterpenes

Terpinen-4-ol 1181 2.24

Nerol 1254 2,97

Methyl Eugenol 1409 0.62

Linalyl Butyrate 1423 5.16

Sesquiterpene hydrocarbons

α-Longipinene 1351 1.52

α-Gurjunene 1404 0.69

α-Cedrene 1410 1.31

allo Aromadendrene 1464 1.14

Cuparene 1501 0.89

β-Himachalene 1502 0.42

β-Bisabolene 1519 1.21

Oxygenated sesquiterpenes

Nerolidol 1565 2,07

Guaiol 1595 4.22

β-Eudesmol 1668 29.83

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table 1. (continued).

Compounds RI^a Percentage %

(E,E)-Farnesyl Acetate 1843 12.66

Hydrocarbons

2,3,4,5-Tetramethyltricyclo[3.2.1.02,7]oct-3-ene - 4.16 Others

1,4 -Naphthalenedione, 5,8-dihydroxy-2-methoxy- - 4.07

Monoterpene hydrocarbons 6.33

Oxygenated monoterpenes 10.99

Sesquiterpene hydrocarbons 7.18

Oxygenated sesquiterpenes 48.78

Hydrocarbons 4.16

Others 4.07

Total identified 81.51

a = Retention indices on DB5-MS column The major constituents of the flower oil were, β-eudesmol (29.83 %), (E,E)-farnesyl acetate (12.66 %), linalyl Butyrate (5.16 %), Isoterpinolene (4.36 %), 2,3,4,5-tetramethyltricyclo [3.2.1.02,7]oct-3-ene ( 4.16 %), guaiol (4.22 %), 1,4-naphthalenedione, 5,8-dihydroxy- 2-methoxy- (4.07 %), and Nerol (2.97 %). Sesqui- terpenes constituted the most abundant fraction of the oil (55.96 %), with a prevalence of oxygenated sesquiterpene (48.78 %) among which β-eudesmol (29.83 %), (E, E)-farnesyl acetate (12.66 %), and guaiol (4.22 %) predominated.

As regards monoterpenes, 4 oxygen containing monoterpenes accounted for the 10.99 % of the total oil, with Linalyl Butyrate (5.16 %) as main compound, while isoterpinolene (4.36 %) was the major of monoterpene hydrocarbon fraction (6.33

%).

In comparison to the result previously reported in the literature in 2007 by Essaqui et al ¹², for oil of W. saharae, we find that β-eudesmol, guaiol, nerol, terpinen-4-ol, nerolidol, β- bisabolene , allo Aromadendrene and p-cymene,

were the common volatile constituents. Also the percentage of β-eudesmol (29.83 %) in our oil was more than half percentage mentioned by Essaqui et al ¹². In addition, fourteen components were found in our essential oil and have not been identified by the same authors. As far as we know, these fourteen components have not been previously described in the W. saharae oil in the literature.

The compounds were separated into three classes, which were terpenoids, hydrocarbons and others fractions. The numbers of the identified terpenoids in the flower of W.saharae was 19 compounds. We observed that the terpenoids fraction represented 73.28 % of the total oil composition, while the hydrocarbons and others fraction represented respectively 4.16 % and 4.07

%.

We conclude from this work that the essential oil from the flower of Moroccan W. saharae is characterized by higher percentage of terpenoids components particularly the oxygenated sesquiterpenes (48.78 %).

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