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Essential oil of some seasonal flowering plants grown in Saudi Arabia
*Corresponding author. Tel.: +966 503449576; fax: +966 14704558 Sarah_almazroa@yahoo.com (S.A. Al-Mazroa)
-
Received: ,
Accepted: ,
This article was originally published by Elsevier and was migrated to Scientific Scholar after the change of Publisher.
Peer review under responsibility of King Saud University.

Available online 16 June 2011
Abstract
The constituents of the essential oils of Rumex vesicarius, Erucaria hispanica, Schimpera arabica, Savignya parviflora, Horwoodia dicksoniae, Sisymbrium irio, Plantago amplexicaulis, Plantago boissieri, Arnebia linearifolia, Foeniculum vulgare, Trigonella hamosa, Lotus halophilus, Reseda muricata, Cenchrus ciliaris is reported. These oils were analyzed by GC/MS and most of them are being studied for the first time.
Keywords
Essential oil
R. Vesicarius
E. Hispanica
S. arabica
S. Parviflora
H. Dicksoniae
S. Irio
P. Amplexicaulis
P. Boissieri
A. Linearifolia
F. Vulgare
T. Hamosa
L. Halophilus
R. Muricata
C. Ciliaris
1 Introduction
The rainy season in the central region of Saudi Arabia which comes between January and April brings with it a variety of flowering plants. Some of those plants are edible by local people while others are used in folk medicine (Chaudhary et al., 1419; Takechi and Tangka, 1994; Tanira et al., 1996; Singh et al., 1998; Ruberto et al., 2000; Shukla et al., 1989; Kim and Ahn, 2001; Boulos, 1983; Shinwar and Khan, 2000).
In continuation of our interest in the chemical constituents of plants grown in Saudi Arabia (Al-Khathlan et al., 1991; Al-Hazimi and Al-Khthlan, 1993; Al-Khathlan and Al-Hazimi, 1996; Al-Mazroa, 2003). We report here a detailed GC/MS study of the essential oils of fourteen plants belonging to eight different families. These are Rumex vesicarius (Polygonaceae), Erucaria hispanica, Schimpera arabica, Savignya parviflora, Horwoodia dicksoniae, Sisymbrium irio (Cruciferae), Plantago amplexicaulis, Plantago boissieri, (Plantaginaceae), Arnebia linearifolia (Boraginaceae), Foeniculum vulgare (Umbeliferae, Apiaceae), Trigonella hamosa, Lotus halophilus (Leguminosae), Reseda muricata (Resedaceae), Cenchrus ciliaris (Gramineae). Most of these plants are being studied here for the first time except for R. vesicarius (Al-Hazimi and Al-Khthlan, 1993) S. irio (Khan et al., 1991). P. ampexicaulis (Ronsted et al., 2001). R. muricata (El-sayed et al., 2001) and F. vulgare (Ravid et al., 1983; Arsalan et al., 1989; Singh et al., 1990; Venskutonis and Dapkevicius, 1996; Baser and Ozek, 1997; Muckenstrum et al., 1997; Ruberto et al., 2000; Jimenez et al., 2000; Ono et al., 1996; Mimica-Dukic et al., 2003; Kawther, 2007; Gulfaraz et al., 2008; Chowdury et al., 2009; Miguel et al., 2010).
2 Experimental
2.1 Plant material
The plant samples were collected from the central region of Saudi Arabia over the period of January to March 2001 and was identified at the Herbarium of the Department of Botany, King Saud University, Riyadh, Saudi Arabia. Aerial parts of fresh plants (50 gm each) were ground and subjected to hydrodistillation for 4 h using essential oil distillation apparatus.
2.2 Essential oils analysis
The essential oils were analyzed on Shimadzu GC/MS-QP 5050 system. The column used was DB-1 glass column (30 m × 0.25 nm). The carrier gas was helium with a flaw rate of 41.8 ml/min, the injector temperature was 250 °C with column temperature ranging from 50–290 °C. The MS was operated with 0.1 L split 100:1 using El Mode. Each compound was identified by comparison with the literature reports and by computer matching with standard spectra in NIST and Wiley libraries (Stenhagen et al., 1975; Formacek, 1982).
3 Results and discussion
3.1 Rumex vesicarius
Essential oils of six plant samples collected from different places of central Saudi Arabia were obtained by steam distillation. The samples were given the following codes according to the place of collections: Sudier (200 km north of Riyadh) (RV-1), Dawadmi (300 km west of Riyadh) (RV-2), Kharj (100 km south of Riyadh) (RV-3), Riyadh Airport (50 km north of Riyadh) (RV-4), Aljenadriah (80 km east of Riyadh) (RV-5), and Riyadh city (RV-6). Yields of essential oils obtained from these samples on fresh weight basis are given in Table 1.
| Sample | % |
|---|---|
| RV-1 | 0.02 |
| RV-2 | 0.10 |
| RV-3 | 0.09 |
| RV-4 | 0.06 |
| RV-5 | 0.03 |
| RV-6 | 0.06 |
Steam distillation of these samples gave light brownish color oil with no smell which turned to a waxy like material after being left for few minutes at room temperature. Gas chromatography–mass spectrometry (GC–MS) analysis of the oil samples resulted in the identification of fifteen constituents of the oils in total. The relative concentrations of the volatile components identified are presented in Table 2. The major constituents of Sudier (RV-1) oil were nonacosane (27.7%), pentatriacontane (16.7%), palmitic acid (12.9%), 3,8-dimethylundecane (6.4%), and 2-ethyl-2-methyl-l-decanol (5.8%). The major constituents of Dawadmi (RV-2) oil were 9,12-octadecadienoic acid (41.4%), palmitic acid (39.4%) and phytol (7.7%). The major constituents of Kharj (RV-3) oil were palmitic acid (30.7%) and phytol (17.4%). The major constituents of Riyadh Airport (RV-4) oil were 9,12,15-octadecatrienoic acid (46.7%) and palmitic acid (26.0%). The major constituents of Aljenadriah (RV-5) were palmitic acid (37.2%) and 9,12,15-octadecatrienoic acid (29.5%) while the major constituents of Riyadh city (RV-6) oil were 9,12-octadecadienoic acid (29.1%) and palmitic acid (20.3%).
| Compound | RV-1 | RV-2 | RV-3 | RV-4 | RV-5 | RV-6 |
|---|---|---|---|---|---|---|
| Palmitic acid | 12.9 | 39.4 | 30.7 | 26.0 | 37.2 | 20.3 |
| Phytol | – | 7.7 | 17.4 | – | 5.8 | 2.8 |
| Tetracosane | 2.6 | – | 1.5 | 1.6 | – | – |
| Eicosane | 3.8 | – | 2.4 | – | – | – |
| Tetratetracontane | 4.4 | 0.3 | – | – | – | 4.4 |
| Pentatriacontane | 16.7 | 0.3 | – | 1.4 | – | 1.4 |
| Nonacosane | 27.7 | – | – | – | – | |
| 2-Ethyl-2-rnethyl-l-decanol | 5.8 | 0.2 | – | – | 2.3 | 1.8 |
| 3,8-Dimethylundecane | 6.4 | – | 2.4 | – | – | – |
| 9,12-Ottadecadienoic acid | – | 41.4 | – | – | – | 29.1 |
| Tritetracontane | – | 0.5 | – | 0.6 | – | 2.3 |
| 1-Nonene-4,6,8-trimethyl | – | – | – | – | 1.4 | 4.6 |
| 3-Dodecanone | 3.5 | – | – | – | 2.6 | – |
| Nonadecane | – | – | 2.2 | – | 1.4 | – |
| 9,12,15-Octadecatrienoic acid methyl ester | – | – | – | 46.7 | 29.5 | – |
From Table 2 it is evident that essential oils composition of R. vesicarius collected from six places of central Saudi Arabia were drastically varies quantitatively as well as qualitatively. Palmitic acid was the only compound which was present as major constituents (ranging from 12.9–39.4%) in all oil samples of R. vesicarius, thus presence of palmitic acid could be considered as a characteristic parameter for R. vesicarius essential oils.
3.2 Erucaria hispanica
Steam distillation of E. hispanica aerial parts gave oil in 0.04% yield (v/w) on fresh weight basis. Gas chromatography–mass spectrometry (GC–MS) analysis of the oil resulted in the identification of total 13 constituents representing 85.1% of the oil. The relative concentrations of the volatile components identified are presented in Table 3. The main constituents of the oil were palmitic acid (36.7%), cyclohexanol dodecyl (11.2%), 1,14,17-Eicosatrienoic acid methyl ester (9.1%), Linolenic acid (7.5%) and phytol (5.6%).
| Compound | % | MW |
|---|---|---|
| Dodecanoic acid | 3.9 | 200 |
| Tetradecanoic acid (Myristic acid) | 6.4 | 228 |
| Cyclohexanol, dodecyl | 11.2 | 268 |
| Linolenic acid | 7.5 | 292 |
| Palmitic acid | 36.7 | 256 |
| Bicyclo-3,1,1-hept-3-en-2-ol | 1.3 | 152 |
| Phytol | 5.6 | 296 |
| 1 l,14,17,Eicosatrienoic acid, methyl ester | 9.1 | 320 |
| Palmitaldehydedially acetate | 1.8 | 338 |
| 4,1 1-Dodecanedione | 1.6 | 198 |
| 3,8-Dimethyl decane | 4.5 | 170 |
| Docosane | 2.4 | 310 |
| Pentatriacontane | 3.2 | 492 |
3.3 Schimpera arabica
Fresh aerial parts of S. arabica was steam distilled to gave oil in 0.18% yield (v/w) on fresh weight basis. The oil was analyzed by Gas chromatography–massspectrometry (GC–MS) which resulted in the identification of 13 constituents representing 97.4% of the oil. The relative concentrations of the identified compounds are presented in Table 4. The major constituents of the oil were palmitic acid (42.6%), linolenic acid (16.7%), tetradecanoic acid (14.3%) and undecanoic acid (5.6%).
| Compound | % | MW |
|---|---|---|
| Pentanoic acid | 1.4 | 102 |
| Undecanoic acid | 5.6 | 186 |
| Tetradecanoic acid | 14.3 | 228 |
| Oxirane, decyl | 3.1 | 184 |
| Palmitic acid | 42.6 | 256 |
| Butanoic acid | 1.6 | 88 |
| Butanoic acid,2-propenyl ester | 0.4 | 128 |
| Linolenic acid | 16.7 | 292 |
| Ether,3-butenyl pntyl | 0.9 | 142 |
| Eicosane | 4.9 | 282 |
| Octane,3-ethyl-2,7-dimethyl | 0.7 | 170 |
| 2,9-Dimethyldecane | 4.7 | 170 |
| Hexane,3,3-dimethyl | 0.5 | 144 |
3.4 Savignya parviflora
Aerial parts of this plant gave yellow color oil in 0.13% yield (v/w) on a fresh weight basis by steam distillation. Gas chromatography–mass spectrometry (GC/MS) analysis of the oil resulted in the identification of 14 components representing 89.8% of the oil. The relative concentrations of the identified constituents are presented in Table 5. The major constituents of the oil were palmitic acid (40.9%), Phytol (8.5%), eicosane (6.4%) and tetratetracontane (5.9%).
| Compound | % | MW |
|---|---|---|
| Cyclopentaneundecanoic acid | 1.6 | 254 |
| Dodecanoic acid | 3.5 | 200 |
| Tetradecanoic acid (Myristic acid) | 3.2 | 228 |
| p-Menth-8(10)-en-9-ol | 4.5 | 154 |
| Palmitic acid | 40.9 | 256 |
| Butanoic acid-3-methyl | 1.8 | 102 |
| Phytol | 8.5 | 296 |
| 1 0-Undecyn- 1-ol | 5.1 | 168 |
| Oleic acid | 2.8 | 280 |
| 2,9-Dimethyldecane | 2.2 | 170 |
| 3,3-Dimethylhexane | 1.6 | 114 |
| Eicosane | 6.4 | 228 |
| Dodecane, 2-methyl | 1.7 | 184 |
| Tetratetracontane | 5.9 | 618 |
3.5 Horwoodia dicksoniae
Aerial parts of H. dicksoniae yielded 0.07% oil (v/w) on fresh weight basis by steam distillation. The volatile oil has a yellow color. Fifteen component representing 98.8% of the oil were identified through Gas chromatography–mass spectrometry (GC/MS) analysis. The relative concentrations of the identified constituents are presented in Table 6. The principle components of this oil were heaxtriacontane (55.0%), pentacosane (19.4%), palmitic acid (6.2%) and tricosane (4.9%).
| Compound | % | MW |
|---|---|---|
| Oxirane, dodecyl | 0.9 | 212 |
| Undecannoic acid, methyl ester | 0.6 | 200 |
| Palmitic acid | 6.2 | 256 |
| Nonadecanoic acid, methyl ester | 0.6 | 326 |
| 1 0-Octadecanoic acid, methyl ester | 1.0 | 296 |
| Phytol | 3.1 | 296 |
| Cyclopentanone-2-(1-methylpropyl) | 1.1 | 140 |
| Nonadecanol | 1.6 | 284 |
| Tricosane | 4.9 | 324 |
| Cyclogeraniolane | 0.7 | 126 |
| Eicosane | 1.4 | 282 |
| Pentacosane | 19.4 | 352 |
| Heptacosane | 3.0 | 380 |
| Nonacosane | 1.5 | 408 |
| Hexatriacontane | 55.0 | 506 |
3.6 Sisymbrium irio
Steam distillation of S. irio Aerial parts gave yellow color oil in 0.08% yield (v/w) on fresh weight basis. Gas chromatography–mass spectrometry (GC–MS) analysis of the oil resulted in the identification of total 13 constituents representing 67.1% of the oil. The relative concentrations of the volatile components identified are presented in Table 7. The main constituents of the oil were palmitic acid (10.4%), menthol (6.7%), Pentacosane (6.5%) and n-heptadecanol (5.2%).
| Compound | % | MW |
|---|---|---|
| Palmitic acid | 10.4 | 256 |
| n-Heptadecanol | 5.2 | 256 |
| Menthol | 6.7 | 156 |
| 2-Hexyl-l-decanol | 4.2 | 242 |
| cis-Cyclohexan-l,l,2-trimethyl-3,5-bis(l-methylethyl) | 3.8 | 206 |
| Hexatriacontane | 3.8 | 506 |
| Pentacosane | 6.5 | 352 |
| Tricyclo-4,3,O,O,7,9-nonane,2,2,5,5,8,8-hexamethyl | 4.8 | 206 |
| Oxirane, dodecyl | 4.2 | 212 |
| 2-Hex,yl-l-decanol | 4.9 | 242 |
| NonadecanoJ | 4.7 | 284 |
| Decahydro-9-ethyl-4,4,8,10-tetramethyl naphthalene | 4.5 | 222 |
| Oxirane,tetradecyl | 3.5 | 240 |
3.7 Plantago amplexicaulis
Fresh aerial parts of P. amplexicaulis yielded 0.07% oil (v/w) on fresh weight basis by steam distillation. The volatile oil turned to a waxy like material after being left for few minutes at room temperature. Eight constituents representing 49.7% of the oil were identified through Gas chromatography–mass spectrometry (GC/MS) analysis. The relative concentrations of the identified constituents are presented in Table 8. The principle components of this oil were palmitic acid (19.8%), 3-mathylundecane (10.5%) and l-ethyl-2-methylcyclohexanol (7.8%).
| Compound | % | MW |
|---|---|---|
| Myristic acid | 1.7 | 228 |
| 1-Ethyl-2-methylcyclohexanol | 7.8 | 142 |
| Palmitic acid | 19.8 | 156 |
| 3 -Methyl undecane | 10.5 | 170 |
| 2,4-Dimethyl undecane | 1.1 | 184 |
| Pentane,2,3,3-trimethyl | 1.3 | 114 |
| 2,4-Dimethyl decane | 3.1 | 170 |
| 2,9-Dimethyl decane | 4.6 | 170 |
3.8 Plantago boissieri
Steam distillation of P. boissieri aerial parts gave oil in good yield i.e. 0.2% (v/w) on fresh weight basis. Gas chromatography–mass spectrometry (GC–MS) analysis of the oil resulted in the identification of total seven constituents representing 67.89% of the oil. The relative concentrations of the volatile components identified are presented in Table 9. The main constituents of the oil were Bicyclo-2,2,1-heptane,2-(2-propenyl) (17.86%), l-dodecane-3-ol (12.36%), phenol, 3-ethyl (9.8%) phenol, 4-methyl (7.96%), nonacosane (7.64%), 2,3,6-trimethyl hepta-6-en-l-ol (6.41%) and benzoic acid (5.86%).
| Compound | % | MW |
|---|---|---|
| Phenol, 4-methyl | 8.0 | 108 |
| Bicyclo-2,2, 1-heptane,2-(2-propenyl)- | 17.9 | 136 |
| Phenol, 3–ethyl | 9.8 | 122 |
| Benzoic acid | 5.9 | 122 |
| 2,3,6-Trimethyl hepta-6-en-l-ol | 6.4 | 156 |
| l-Dodecane-3-ol | 12.4 | 184 |
| Nonacosane | 7.6 | 408 |
3.9 Arnebia. linearifolia
Aerial parts of A. linearifolia gave oil in 0.01% yield (v/w) on fresh weight basis by steam distillation. The volatile oil turned to a waxy like material after being left for few minutes at room temperature. Twelve constituents representing 90.6% of the oil were identified through Gas chromatography–mass spectrometry (GC/MS) analysis. The relative concentrations of the identified constituents are presented in Table 10. The major components of this oil were phytol (19.0%), pentalene, octahydro-l-(2-octyldecyl) (18.8%), docosane (11.8%), tetratetracontane (9.2%), heptadecane (7.9%) and palmitic acid (7.3%).
| Compound | % | MW |
|---|---|---|
| Myristic acid | 1.2 | 228 |
| Pentalene, octahydro-1-(2-octyldecyl) | 18.8 | 362 |
| 1,6, 1 0-Dodectrien-3-ol,3,7, 1 1–trimethyl | 2.5 | 222 |
| Palmitic acid | 7.3 | 256 |
| Bicyclo-3,l,l-heptane,2,6,6-trimethyl-3(2-ropenyl) | 1.7 | 178 |
| Phytol | 19.0 | 296 |
| 3,3-Dimethyl hexane | 1.3 | 114 |
| Heptadecane | 7.9 | 240 |
| 2-methyl, undecane | 4.7 | 170 |
| Docosane | 11.8 | 310 |
| Hexatriacontane | 5.2 | 506 |
| Tetfatefracontane | 9.2 | 618 |
3.10 Foeniculum vulgare
Detailed literature survey revealed that several studies on essential oil of F. vulgare growing in different parts of world (Ronsted et al., 2001; El-sayed et al., 2001; Ravid et al., 1983; Arsalan et al., 1989; Singh et al., 1990; Venskutonis and Dapkevicius, 1996; Baser and Ozek, 1997; Muckenstrum et al., 1997) have been done. However, no literatures on chemical investigation of F. vulgare grown in Saudi Arabia were found. This prompted us carry out this study. Steam distillation of F. vulgare aerial parts gave a yellow oil in 0.1 yield (v/w) on fresh weight basis. Gas chromatography–mass spectrometry (GC–MS) analysis of the oil resulted in the identification of total nine constituents representing 99.6% of the oil. The relative concentrations of the volatile components identified are presented in Table 11. The principle constituents of the oil were anethole (76.4%) and apiol (16.3%).
| Compound | % | MW |
|---|---|---|
| 7-Anisaldehyde | 0.9 | 136 |
| Anethole | 76.4 | 148 |
| Apiol | 16.3 | 222 |
| Palmitic acid | 0.8 | 256 |
| Falcarinol(Z)-(−)-1,9-heptadecadiene-4,6-diyne-3Lol | 0.3 | 244 |
| Phytol | 4.0 | 296 |
| Dodecane | 0.3 | 170 |
| Eicosane | 0.3 | 282 |
| 2,9-Dimethyl decane | 0.4 | 170 |
3.11 Trigonella hamosa
Fresh aerial parts of T. hamosa on steam distillation gave yellow color oil in yield 0.04% (v/w) on fresh weight basis. Twelve constituents representing 91.1% of the oil were identified through Gas chromatography–mass spectrometry (GC/MS) analysis. The relative concentrations of the identified components are presented in Table 12. The major components of this oil were palmitic acid (38.4%), tetradecanoic acid (15.9%), linolenic acid methyl ester (11.3%), phytol (7.6%) and decanoic acid (7.3%).
| Compound | % | MW |
|---|---|---|
| Decanoic acid | 7.3 | 200 |
| Tetradecanoic acid | 15.9 | 228 |
| Cyclohexanol, dodecyl | 0.8 | 268 |
| Palmitic acid | 38.4 | 256 |
| Ether, heptyl hexyl | 1.1 | 200 |
| Phytol | 7.6 | 296 |
| Linolenic acid, methyl ester | 11.3 | 292 |
| Isopregol | 1.5 | 154 |
| Oleic acid | 1.4 | 282 |
| Pentatricontane | 0.9 | 492 |
| Docasane | 1.5 | 310 |
| Hexatricontane | 3.4 | 506 |
3.12 Lotus halophilus
Steam distillation of L. halophilus aerial parts gave yellow color oil in yield 0.07% (v/w) on fresh weight basis, interestingly, only three components contributing 99.3% of the oil were identified. The relative concentrations of these three identified components i.e. phytol (49.8%), Heptadecane (33.0%) and 2,9-Dimethyldecane (6.3%) are presented in Table 13.
| Compound | % | MW |
|---|---|---|
| Phytol | 49.8 | 296 |
| 2,9-Dimethyldecane | 16.3 | 170 |
| Heptadecane | 33.0 | 240 |
3.13 Reseda muricata
Steam distillation of R. muricata aerial parts gave yellow oil in 0.13% yield (v/w) on fresh weight basis. Gas chromatography–mass spectrometry (GC–MS) analysis of the oil resulted in the identification of total 12 constituents representing 63.2% of the oil. The relative concentrations of the volatile components identified are presented in Table 14. The main constituents of the oil were hexatricontane (17.2%), palmitic acid (10.0%), nonadecane (8.9%), phytol (6.8%) and 2,2-dimethyl-3-(E)-beta-(2-methylallyl)-cyclopropane carboxylic acid (6.5%).
| Compound | % | MW |
|---|---|---|
| 2,2-Dimethyl-3-(E)-beta(2-methylallyl) Cyclopropane-carboxylic acid | 6.5 | 168 |
| 2,4-Dimethyl decane | 0.4 | 170 |
| Palmitic acid | 10.0 | 256 |
| Pbytol | 6.8 | 296 |
| 1,3-Methanopentalene, octahydro | 2.3 | 122 |
| Pentanoic acid,3–methyl | 0.3 | 116 |
| Eicosane | 4.9 | 282 |
| Hexane-3,3-dimethyl | 2.5 | 114 |
| Nonadecane | 8.9 | 268 |
| Ether, hexyl pentyl | 1.8 | 172 |
| Hexatricontane | 17.2 | 268 |
| Octane,3-ethyl-2,7-dimethyl | 1.4 | 170 |
3.14 Cenchrus ciliaris
Fresh aerial parts of C. ciliaris was steam distilled to gave oil in 0.08% yield (v/w) on fresh weight basis. The oil was analyzed by Gas chromatography–mass spectrometry (GC–MS) which resulted in the identification of 13 constituents representing 86.4% of the oil. The relative concentrations of the identified compounds are presented in Table 15. The major constituents of the oil were palmitic acid (42.9%), phytol (9.9%), tridecanol, 2-ethyl-2-methyl (6.7%) and 3,9-dimethylundecane (5.8%).
| Compound | % | MW |
|---|---|---|
| Valeric acid | 3.0 | 102 |
| n-Caproic acid | 1.4 | 116 |
| 3,4-Dimethyl cyclohexanol | 4.2 | 128 |
| Palmitic acid | 42.9 | 256 |
| Phytol | 9.9 | 296 |
| 3-Buten-2-ol,2-methyl | 2.0 | 86 |
| cis-3-Hexane | 1.3 | 84 |
| 3,3-Dimethyl hexane | 0.7 | 114 |
| l-Butyne,3-methyl-3(l-methylethoxy) | 1.4 | 126 |
| Tridecanol,2-ethyl-2-methyl | 6.7 | 242 |
| 4-Penten-1-ol,2,2,4-trimethyl | 5.1 | 128 |
| 3,9-Dimethyl undecane | 5.8 | 184 |
| Octane,3-ethyl-2,7-dimethyl | 2.0 | 170 |
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