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Natural Product Communications
Chemical Composition of the Essential Oil of Pituranthos scoparius
2011 Vol. 6 No. 8 1151 - 1154
Nadhir Gourinea*, Bahia Merrada, Mohamed Yousfia, Pierre Stockerb and Emile M. Gaydouc a
Université Amar Thélidji de Laghouat, Laboratoire des Sciences Fondamentales (LSF), Équipe Chimie Organique Appliquée, B.P. 37G, (03000) Laghouat, Algeria b Laboratoire de Biosciences, Faculté des Sciences et Technique de Saint-Jérôme, Université Paul Cézanne, Marseille, France c Université Paul Cézanne, Faculté des Sciences et Techniques de Saint-Jérôme, UMR CNRS 6263, Institut des Sciences Moléculaires de Marseille (ISM2), AD2EM, LSCC, Groupe Phytochimie, Boîte 461, Av Escadrille Normandie Niémen, F-13397 Marseille Cedex 20, France
[email protected] Received: February 6th, 2011; Accepted: April 9th, 2011
The essential oils obtained by hydro distillation of the aerial parts of Pituranthos scoparius were collected from different regions of Algeria and gave various yields ranging from 0.6 up to 2.8% (v/w). These samples were analyzed by GC and GC-MS showing the occurrence of monoterpene hydrocarbons and some oxygenated compounds. The major components were α-pinene (4.4-35.8%), limonene (0.8-66.5%), bornyl acetate (tr-9.6%), myristicin (tr-31.1) and dill apiole (0.4-47.3%). The aerial parts of P. scoparius could be either very rich or very poor in limonene, myristicin or dill apiole. Cluster analysis shows differences in essential oil compositions of samples coming from the different area collected. Keywords: Pituranthos scoparius, essential oil, monoterpene, myristicin, dill apiole, cluster analysis.
Pituranthos scoparius (Coss. & Dur.) Schinz (Umbelliferae) (=Deverra scoparia Coss. & Dur), commonly known as “guezzah” is a Saharan species [1] used in traditional medicine for the treatment of asthma and rheumatism [2,3]. The Touareg people which are little communities living in the Algerian desert of Tassili and Hoggar, also use it in food as aroma for meal and bread [3]. Only a very few studies were conducted on this plant. The main previous studies deal with the antibacterial of the flavonoids [4] antibacterial activities of the essential oils [1,5], chemical composition of the essential oil of stems and seeds (Table 1) [6,7]. Two isocoumarins from the roots of P. scoparius were isolated [8]. Recently, the antioxidant activity of the phenolic extracts [9] and their constituents [10] were also reported. The aim of the present study is to carry out a large scale investigation on the essential oil composition of P. scoparius in Algeria which involves different regions and locations never investigated to our knowledge. This is the first time that the aerial parts (mixture of stems and seeds) of the essential oil of P. scoparius are investigated. Extracts of P. scoparius aerial parts yielded a green-yellow color oils (0.6–2.8%) (v/w) with a very characteristic odor. The aerial parts of P. scoparius essential oils were analyzed by GC and GC–MS. Thirty eight compounds
Table 1: Major components in seeds and stems Pituranthos scoparius essential oils, growing in Ghardaïa [5] and Ain-Diss [6] areas (Algeria). Compound α-Pinene β-Pinene α-Phellandrene p-Cymene Limonene Thymol Methyleugenol Germacrene D Myristicin Spathulenol Dill apiole
Stem Seeds % [6] 8.2 6.8 4.6 3.8 4.0 7.1 7.5 4.2 11.2 9.8 5.9 0.1 1.6 5.9 1.0 12.7 11.1 7.2 2.5 4.5 12.2 1.1
Compound α-Pinene p-Cymene Bornyl acetate trans-Verbenol Apiol
Stem Seeds % [7] 11.0 34.0 1.6 3.3 21.0 0.2 0.2 3.6 52.8 15.0
were identified showing high amounts in monoterpenes (45.3-83.7%), with mainly monoterpene hydrocarbons (44.4-81.9%). Some samples were also rich in oxygenated compounds such as myristicin + dill apiole (3.5-48.1%) (Table 2). The main components identified were α-pinene (4.4-35.8%), limonene (0.8-66.5%), bornyl acetate (tr-9.6%), myristicin (tr-31.1) and dill apiole (0.4-47.3%). The samples investigated presents large variations of percentage intervals relatively to each main component; which supposes the existence of some chemotypes within the same species.
1152 Natural Product Communications Vol. 6 (8) 2011
Gourine et al.
Table 2: Component identifications of Pituranthos scoparius aerial part of essential oils from three regions in Algeria. GC peaks area (%)a b
Compounds α-Pinene Camphene β-Pinene Sabinene δ-3-Carene β-Myrcene α-Phellandrene α-Terpinene Limonene β-Phellandrene cis-β-Ocimene γ-Terpinene trans-β-Ocimene p-Cymene α-Terpinolene α-Copaene Linalool Bornyl acetate β-Caryophyllene Terpinen-4-ol α-Terpineol Germacrene D Bicyclogermacrene δ-Cadinene Methyl eugenol Carotol Spathulenol α-Cadinol δ-Cadinol τ-Muurolol α-Eudesmol β-Eudesmol NI Myristicin Dill apiole Butyldiene dihydrophthalide Myristic acid Palmitic acid Total identified Monoterpenes HC Oxygenated monoterpenes Total monoterpenes Sesquiterpenes HC Oxygenated sesquiterpenes Total sesquiterpenes Other oxygenated compounds
Ghardaïa BRNc 4 5 8.4 5.5 tr tr 0.5 2.0 0.4 0.3 tr tr 0.6 0.6 0.7 4.1 tr tr 45.0 37.2 tr 2.0 tr tr 1.3 0.9 tr tr 0.6 2.4 tr 0.3 tr 0.4 tr 0.6 tr tr 0.4 tr tr tr tr 0.3 2.8 5.9 1.3 0.8 1.0 1.3 tr 1.4 − − 0.5 0.6 tr tr 3.1 tr 0.5 0.7 tr tr tr tr 0.4 1.7 2.6 25.1 0.9 23.0
1 8.1 tr 0.5 0.2 tr 0.7 4.6 tr 66.5 0.6 tr 0.1 tr 0.5 0.1 0.1 0.1 0.1 0.3 0.1 0.1 2.1 0.4 0.5 0.1 − 0.1 tr 0.9 0.2 tr tr 0.2 tr 11.3
2 11.2 tr 2.9 0.2 tr 0.6 6.4 tr 49.5 2.6 tr tr tr 1.8 0.3 tr tr tr 0.3 0.2 0.3 3.8 0.6 1.2 0.3 1.1 0.6 tr tr 1.0 tr tr 1.0 5.2 1.03
3 4.7 tr 1.2 tr tr 0.3 2.1 tr 32.7 0.8 tr 2.0 tr 0.7 tr tr tr tr 0.3 tr 0.9 4.3 2.0 1.3 0.6 tr 0.5 tr 3.6 0.4 tr tr 0.8 12.4 22.6
tr
5.5
1.4
0.4
− −
− −
− −
− −
98.2 81.9
97.4 75.5
95.5 44.5
93.1 57.4
Laghouatb SMKc AMDc 8 9 35.8 35.1 2.4 1.2 5.2 5.2 2.2 1.1 tr tr 1.3 1.1 1.0 2.0 0.2 tr 7.0 30.0 0.6 0.7 tr tr 0.9 2.0 tr tr 1.0 1.6 0.2 tr tr tr 0.2 tr 3.0 9.5 tr 0.2 1.1 0.4 0.2 0.1 1.3 1.6 0.4 0.3 0.6 0.5 tr 0.2 − 0.1 0.3 0.2 tr tr tr tr tr 0.2 0.3 tr tr tr 1.2 0.2 − 1.9 25.7 9.9
Djelfab ABDc 10 11 23.7 26.7 tr 2.1 4.1 5.3 1.1 0.9 1.1 1.4 0.6 1.2 1.2 1.9 tr tr 0.9 7.8 0.9 0.6 3.2 3.8 tr 1.0 tr tr 2.0 6.7 tr tr tr tr 1.94 tr Tr 9.6 0.6 tr 0.9 0.6 0.4 tr 3.3 1.1 tr tr 1.4 0.5 1.7 tr tr − 1.7 0.6 tr tr 0.4 tr 1.6 tr tr 0.3 0.5 tr 3.0 0.4 2.5 18.2 1.4 30.3
DJLc 12 27.0 tr 1.7 4.6 tr 0.9 0.8 tr 4.0 tr 1.2 2.3 tr 2.1 tr tr tr tr 0.3 0.6 tr 2.5 0.6 0.6 0.7 − 1.2 tr tr 0.7 tr tr tr tr 47.3
LRId
Identification
1029 1072 1123 1139 1154 1168 1173 1190 1209 1218 1239 1253 1257 1281 1290 1473 1554 1592 1605 1617 1715 1723 1745 1769 2029 2035 2145 2179 2190 2202 2221 2230 2250 2288 2384
MS, RI MS, RI MS, RI MS, RI MS, RI MS, RI, AS MS, RI MS, RI MS, RI, AS MS, RI MS, RI MS, RI, AS MS, RI MS, RI MS, RI MS, RI MS, RI, AS MS, RI, AS MS, RI, AS MS, RI, AS MS, RI, AS MS, RI MS, RI MS, RI MS, RI MS, RI MS, RI MS, RI MS, RI MS, RI MS, RI MS, RI − MS, RI MS, RI
6 10.4 tr 1.2 0.4 1.0 0.9 1.7 tr 58.3 0.4 tr 0.4 tr 1.0 tr 0.5 tr 0.3 0.6 0.4 tr 6.3 2.3 2.0 2.7 − 1.7 tr tr 1.7 tr tr 1.9 0.4 0.4
7 4.4 tr 1.7 0.3 0.2 0.6 3.6 tr 34.4 1.9 tr 0.8 tr 2.4 0.3 0.5 tr tr 0.2 0.2 0.2 5.3 0.7 0.9 1.9 − 0.7 tr 0.2 0.2 0.8 0.2 1.8 31.1 1.1
1.0
tr
1.0
0.3
tr
0.6
tr
tr
2614
MS, RI
− −
− −
− −
− −
− −
tr 0.7
− −
− −
2707 2915
MS, RI MS, RI
96.0 55.3
96.7 75.6
97.2 50.5
98.6 57.7
98.6 80.0
82.6 44.6
99.4 53.6
98.9 44.4
0.5
0.7
1.2
0.4
1.0
1.0
0.6
10.9
3.7
3.8
10.2
0.9
82.5
76.3
45.7
57.7
56.3
76.6
51.1
68.7
83.7
48.4
63.7
45.3
3.1
5.5
7.6
5.4
8.4
11.3
7.6
2.3
5.3
4.7
1.6
4.1
1.1
2.7
4.5
4.0
1.3
3.4
2.0
0.6
0.5
4.2
0.9
1.8
4.3
8.2
12.1
9.4
9.7
14.7
9.5
2.9
5.8
8.9
2.5
5.9
11.3
12.0
36.9
26.0
28.4
3.5
35.0
25.9
12.0
21.7
32.8
48.1
a
Percentages obtained by FID peak-area normalisation; bRegion; cLocation in the region; dLinear retention indices relative to homologous n-alkanes C8–C40 obtained on UB-Wax column. BRN: Benrriane; SMK: Sidi-Makhlouf; AMD: Ain-Mahdi; ABD: Aïne-Mabed; DJL: outside the town of Djelfa; NI: not identified by GC-MS; tr: traces (
