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Chemical composition of essential oil from Jordanian Lupinus varius L.
*Tel.: +96 277420029; fax: +96 227211117 mahmoud.qudah@yu.edu.jo (Mahmoud A. Al-Qudah)
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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 20 January 2011
Abstract
The chemical composition of essential oil obtained by hydrodistillation from flowering shoots of Lupinus varius L. was analyzed by GC–FID and GC–MS. Chemical analysis of this oil showed that it includes a complex mixture of aldehydes, alcohols, esters and mono- and sesquiterpenes. Forty one compounds were characterized in the oil. The major components of the oil were 6,10,14-trimethyl-2-pentadecanone (20.5%), pentadecanal (10.2%), (E) nerolidol (8.43%), carracol ethyl ether (4.3%), α-humulene (3.6%), (2Z,13E)-ocatadeca-2,13-dien-l0-ol (3.2%) and caryophyllene-5-ol (2.7%).
Keywords
Lupinus varius L
Essential oil
Leguminosae
α-Humulene
E-Nerolidol
1 Introduction
Lupinus is a genus of the flowering plant family Leguminosae or Fabaceae. It includes more than 200 species widely distributed in tropical and warm temperate regions of the world, with major centers of diversity located in the Mediterranean basin and South America (Dervas et al., 1999; Huyghe, 1997; Swiecicki et al., 2000). Three Lupinus species grow naturally in Jordan. These are: Lupinus angustifolius L., Lupinus luteus L. and Lupinus varius L. (Al-Eisawi, 1982).
L. varius L. ssp. orientalis Franco et Silva (=Lupinus digitatus Forssk, Lupinus pilosus L., Lupinus hispanicus and Lupinus microanthus) is an annual herb, growing in the Mediterranean, North Africa, South Europe, West Syria, and Palestine region (Tackholm, 1974; Wink et al., 1995). L. varius is a short to medium soft hairy annual, has the potential for use as a new cutflower crop, possessing inflorescences on the main stem and branches with blue flowers that are longer than that of some the other species of Lupinus (Blamey and Grey-Wilson, 1998; Burnie, 2000; Karaguzel et al., 2003). Previous studies with this species revealed the presence of several quinolizidines, as well as dipiperidine and alkaloids (Abdel-Halim et al., 1999; Mohamed and Hassanean, 1997). However, information about essential oil from the L. varius is unavailable.
L. varius seeds as a possible valuable source for glucomannan, which helps normalize blood sugar, relieve stress on the pancreas, and discourage blood sugar abnormalities, such as hypoglycemia (Hozumi et al., 1995). In this paper we report on the isolation and analysis of the volatile compounds from shoots of L. varius collected from the north part of Jordan.
2 Materials and methods
2.1 Plant material
Flowering shoots of L. varius were collected during March 2010 from populations growing wild in Irbid (Jordan). The plant was identified by Dr. Jamil N. Lahham (Department of Biological Sciences, Yarmouk University, Jordan). A voucher specimen was deposited in the herbarium of the Department of Biological Sciences at Yarmouk University.
2.2 Isolation of essential oil
The classical method of hydrodistillation using the Clevenger-type apparatus for 4 h was used for the isolation of the essential oil from the shoots of L. varius. The essential oil was collected and stored at 4 °C until their analysis by gas chromatography/mass spectrometry (GC–MS).
2.3 GC–FID analysis
Quantitative analysis was carried out using a Hewlett Packard HP-8590 gas chromatography equipped with a split-splitless injector (split ratio, 1:50) and an FID detector. An OPTIMA-5 fused silica capillary column (30 m × 0.25 mm, 0.25 μm film thickness) was used. The oil was analyzed under linear temperature programming applied at 3 °C/min from 60 to 246 °C. Temperatures of the injector and detector (FID) were maintained at 250 and 300 °C, respectively. Concentrations (% contents) of the oil components were calculated using their relative area percentages, obtained by FID, assuming a unity response by all components.
2.4 GC–MS analysis
The chemical analysis of the essential oil was carried out using gas chromatography–mass spectrometry (GC–MS) Agillent 6890 series II-5973 mass spectrometer interfaced with a HP chemstation. The chromatographic conditions were as follows: column oven program, 60 °C (1 min, isothermal) to 246 °C (3 min, isothermal) at 3 °C/min; the injector and detector temperatures were 250 and 300 °C, respectively. Helium was the carrier gas (flow rate 0.90 mL/min). A HP-5 MS capillary column (30 m × 0.25 mm i.d., 0.25 μm film thicknesses) was utilized. The actual temperatures in MS source reached approximately 180 °C. The ionization voltage was 70 eV. A hydrocarbon mixture of n-alkanes (C8-C20) was analyzed separately by GC/MS under same chromatographic conditions using the same HP-5 column.
2.5 Component identification
The components of the hydrodistilled essential oil obtained from fresh plant was identified using built in libraries (Nist Co and Wiley Co, USA) and by comparison of their calculated retention indices relative to (C8-C20) n-alkanes with the literature values measured with columns of identical polarity or with authentic samples (Adams, 2004; Budzikiewicz et al., 1964; McLafferty, 1962). Linalool, hexdecane, δ-cadinene, α-humulene, octadecane, β-eudesmol, (Fluka, Buchs, Switzerland) was used as reference substances in GC/MS analysis. GC-grade n-hexane and analytical reagent grade anhydrous sodium sulfate (Na2SO4) were used.
3 Results
By hydrodistillation, shots of Lupinus varius L. yielded 0.4% (V/W) of a colorless essential oil with a characteristic odor. The results obtained by GC–MS analysis of the oil are presented in Table 1. Forty one components were identified in the shoots of Lupinus varius L. The main component of the essential oil was 6,10,14-trimethyl-2-pentadecanone (20.5%). The other characteristic compounds determined were: pentadecanal (10.2%), (E) nerolidol (8.43%), carracol ethyl ether (4.3%), α-humulene (3.6%), (2Z, 13E)-ocatadeca-2, 13-dien-l0-ol (3.2%) and caryophyllene-5-ol (2.7%). The main compounds of the oil were chemically classified as follows: esters (9.26%), alcohols (5.38%), alkane (4.68%), oxygenated monoterpenes (8.42%), sesquiterpene hydrocarbons (7.01%), and oxygenated sesquiterpenes (43.83%) (Table 2).
| No. | Compound | KI | Area (%) |
|---|---|---|---|
| 1 | (2Z)-3-Pentyl-2,4-pentadien-1-ol | 1070 | 0.65 |
| 2 | Linalool | 1101 | 0.63 |
| 3 | Nonanal | 1102 | 0.84 |
| 4 | 1-Methyl-1-cyclohexen-1-carboxaldehyde | 1121 | 0.85 |
| 5 | Isophorone | 1128 | 0.73 |
| 6 | Nerol | 1226 | 0.64 |
| 7 | Dihydroedulan I | 1290 | 0.92 |
| 8 | Carracol ethyl ether | 1296 | 4.3 |
| 9 | 10-(Acetyl methyl)-(+)-3-carene | 1387 | 1.2 |
| 10 | Ethyl decanoate | 1398 | 0.68 |
| 11 | α-Humulene | 1460 | 3.6 |
| 12 | E-β-Ionone | 1496 | 1.77 |
| 13 | Hexadecane | 1498 | 0.63 |
| 14 | E-10-Pentadecanol | 1512 | 0.74 |
| 15 | δ-Cadinene | 1530 | 1.64 |
| 16 | Davonol acetate | 1556 | 1.1 |
| 17 | Nerolidol (E) | 1561 | 8.43 |
| 18 | Pentadeca-1,3,7,12,14-pentaen-7-ol-9-one | 1568 | 0.90 |
| 19 | Germacrene D-4-ol | 1571 | 1.2 |
| 20 | Spathulenol | 1580 | 1.5 |
| 21 | Caryophyllene oxide | 1584 | 1.7 |
| 22 | 1-Bromo-2-methyldecane | 1598 | 0.82 |
| 23 | (2Z,13E)-ocatadeca-2,13-dien-l0-ol | 1614 | 3.2 |
| 24 | E-Isoeugenol acetate | 1617 | 0.87 |
| 25 | Daranol D1 | 1620 | 2.1 |
| 26 | Caryophyllen-5-ol | 1645 | 2.7 |
| 27 | β-Eudesmol | 1658 | 1.1 |
| 28 | Selin-11-en-4-α-ol | 1662 | 1.9 |
| 29 | Octadecene | 1679 | 2.3 |
| 30 | Pentanoic acid,10-undecenyl ester | 1686 | 1.3 |
| 31 | Acorenone | 1693 | 1.6 |
| 32 | 2-Nonadecanone | 1698 | 1.2 |
| 33 | Pentadecanal | 1715 | 10.2 |
| 34 | Ethyl octadec-9-enoate | 1771 | 1.8 |
| 35 | 9-Tetradecen-1-ol acetate | 1780 | 0.69 |
| 36 | 6,10,14-Trimethyl-2-penta decanone | 1840 | 20.5 |
| 37 | Hexadecanol | 1847 | 0.79 |
| 38 | Octadecane | 1898 | 0.93 |
| 39 | Methyl hexadecanoate | 1914 | 0.62 |
| 40 | Methyl 14-methylpentadecaoate | 1925 | 2.1 |
| 41 | Ethyl hexadecanoate | 1992 | 1.2 |
| Total | 92.57 | ||
| Compound | No. of compounds | Area (%) | |
|---|---|---|---|
| 1 | Oxygenated monoterpenes (%) | 6 | 8.42 |
| 2 | Sesquiterpene hydrocarbons (%) | 3 | 7.01 |
| 3 | Oxygenated sesquiterpenes (%) | 11 | 43.83 |
| 4 | Alcohol | 4 | 5.38 |
| 5 | Aldehydes (%) and ketone | 5 | 13.99 |
| 6 | Esters (%) | 8 | 9.26 |
| 7 | Alkanes (%) | 4 | 4.68 |
4 Conclusion
This is the first report to study the volatile components of essential oil from L. varius L. This study revealed that the oxygenated sesquiterpenes are major components of essential oil from L. varius L. and that is similar to that found in members of the Leguminosae family in previous reports (Alicia et al., 1998; Alessandra et al., 2004; Fethia et al., 2006).
Acknowledgments
The research work was supported by Yarmouk University – Faculty of Graduate Studies and Scientific Research. My gratitudes are due to Dr. Ibrahim Trawenh for technical assistance and to Dr. Riyadh Muhaidat for critical reading of the manuscript.
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