|Iranian Journal of Pharmaceutical Research (2006)
Received: March 2004
Accepted: September 2005
Copyright ? 2005 by School of Pharmacy
Chemical Composition of the Essential Oils of Peucedanum ruthenicum M. Bieb. Leaves, Flowers and Fruits
Sayyed Hamid Reza Alavia, Narges Yasaa*, Fatemeh Fouladia, Abbas Shafieeb
aDepartment of Pharmacognosy, Faculty of Pharmacy and Medicinal Plants Research Center, Tehran University of Medical Sciences, Tehran, Iran. bDepartment of Organic Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran.
The essential oils of Peucedanum ruthenicum M. Bieb. (Umbelliferae) leaves, flowers and fruits were prepared by hydrodistillation and analyzed by GC and GC-MS and the composition of the three essential oils were compared. Thirty-three, thirty-seven and thirty-one compounds were identified in leaves, flowers and fruits essential oils representing 89.13%, 88.66% and 76.45% of total oils respectively. The major components were thymol (18.29%), ?-bisabulene (13.29%) for leaves oil, ?-myrcene (10.68 %) and germacrene-B (10.06%) for flowers oil and caryophyllene oxide (13.65%), 8, 9-dehydroisolongifolene (11.33%) and 1, 8-cineol (11.15%) for fruits oil. The amounts of monoterpens and sesquiterpenes were found nearly to be equal in oils of the three parts of plant.
In Iran, the genus Peucedanum (Umbelliferae) is represented by 4 species: P. glaucopruinosum, P. knappii, P. translucens (1) and P. ruthenicum, which grows wild in different regions of Iran (2). ?P. ruthenicum is a native Bulgarian Umbellifer (3) and is a glabrous perennial plant with abundant fibers; stem cylindric, striate, solid; leaves 3(-4)-ternate, lobes 20-90 mm; rays 7-28; bracts 1-3, subulate; bracteoles several, filiform;? petals pale yellow; fruit 6-7.5 mm in dry places (4). The plant was collected for the first time from Arak (Markazi province) centre of Iran (2). Some species of this genus have been used traditionally in treatment of cold (5), cough due to pathogenic wind-heat, accumulation of phlegm and heat in the lung (6). They have also been used as anti-tussive, anti-asthma and a remedy for angina (7).
Previous studies on these species have shown the presence of furanocoumarins and glycoside derivatives, linear-type furanocoumarin glucosides and simple coumarin glucosides (8, 9). Several new coumarins such as qianhucoumarin I have been reported from P. praeruptorum Dunn. (10).
A phytochemical examination of P. ruthenicum has shown the presence of peucedanin (furanocoumarin) and peuruthenicin (a new coumarin) in the roots and rutin (flavonol glycoside) in the flowers (3). There were some reports related to the chemical analysis of volatile oil of this genus in the literature. The major components of herb and rhizome essential oil of P. ostruthium were sabinene (35.2%), 4-terpineol (26.6%), β-caryophyllene (16.1%) and α-humulene (15.8%) (11). The major constituents of P. verticillare leaf and branch oil were sabinene and trans-anethole and? β-caryophyllene, α-Phellandrene, cis-β-farnesene and β-bisabolene were components of P. verticillare dried fruit oil and sabinene was the constituent of P. verticillare fresh fruit oil (12). The oils constituents from rhizomes, leaves and fruits of P. petiolare (DC.) Boiss. have been studied, the major constituents of rhizome oil were found to be β-bisabolene (31.3%), (E)-sesquilavandulol (20.5%), geranyl acetate (5.7%), citronellyl acetate (5.2%) and sabinene (5.2%); the main components of leaf oil were sabinene (42.3%), α-pinene (42.6%) and limonene (2.6%) and in the fruits, α-pinene (47.3%) and sabinene (45.9%) were the predominant constituents (13). In another study, essential oil of the aerial parts of P. petiolare (DC) Boiss. has been analyzed and among the ten components (97.6%) which identified in this oil, sabinene (57.8%) and δ-3-carene (36.2%) were found to be the major constituents(14). The mian components of water distilled essential oil of P. scoparium were α-Pinene (39.6%), β-pinene (23.9%) and β-phellandrene (9.5%) (15). The component of P. ruthenicum essential oil was not reported previously. In this paper comparison of the essential oils composition of P. ruthenicum leaves, flowers and fruits is reported.
Plant Material and Isolation Procedure
The P. ruthenicum was collected during August to October 2003 from Arak (Markazi province) in Iran and voucher specimen was deposited in the private herbarium of Dr. H. Akhani (hb.Akh.15487) Plant Science Department of Tehran University, Iran.
The plant?s different parts were dried at ambient temperature in the shade. The leaves (150g), flowers (120g) and fruits (120g) were subjected to hydrodistillation using a Clevenger-type apparatus for 4 h (16) and the oils were dried over anhydrous sodium sulfate and stored at 2-8?C.
Identification of the Oil Components
The analysis of the essential oils was performed using a Hewlett Packard 6890 GC equipped with a HP-5MS capillary column (30m x 0.22 mm i.d., 0.25 μm film thickness) and a mass spectrometer 5973 from the same company, for GC-Mass detection with an electron ionization system (70 eV) was used.
Helium was the carrier gas, at a flow rate of 1ml/min., injector and detector temperatures were set at 250 and 290?C respectively, column temperature was initially kept at 60?C for 5 min. then gradually increased to 220?C at the rate of 6?C/min. Retention indices were calculated by using retention times of n-alkanes that were injected after the oil at the same chromatographic conditions. The compounds were identified by comparison of retention indices (RRI, DB-5) with those reported in the literature and by comparison of their mass spectra with the Wiley library or with published mass spectra (17, 18, 19).
Results and Discussion
The results of GC and GC-MS analysis of the essential oils of P. ruthenicum are presented in Table 1. The color of essential oils of leaves, flowers and fruits were pale green, pale yellow and yellow in the total yields of? 0.4%, 1.6%, 1.8% (v/w) ,? respectively. The leaves, flowers and fruits oils of P. ruthenicum contained (34.87%), (50.21%), (43.22%) monoterpenes and (43.57%), (38.45%), (39.67%) sesquiterpenes respectively.
A total of 33 components were identified in leaf oil, representing (89.13%), the major constituents were thymol (18.29%) and β-bisabulene (13.29%). In the oil of flowers, 37 components were identified; representing (88.66%); β-myrcene (10.68%) and germacrene-B (10.06%) were the main components. Twenty four compounds were found in fruits oil, representing (76.45%) of the total oil, caryophyllene oxide (13.65%), 8, 9-dehydroisolongifolene (11.33%) and 1,8-cineol (11.15%) were the major compounds. Comparisons of the major components of the three oils showed some differences among them (Table 1). The oil from leaves is characterized by high contents of thymol (18.29%) and β-bisabulene (13.29%), which do not exist in flowers and fruits oil. In addition, caryophyllene oxide is a major component of fruits oil (13.65%) and the minor component of the leaves (1.42%) and the flowers oil (1.61%). 8, 9-Dehydroisolongifolene (11.33%) and 1, 8-cineol (11.15%) are the major components of fruits oil which do not exist in leaves and flowers oil.
There are some differences between the components of P. ruthenicum and P. verticillare fruit essential oils; caryophyllene oxide, 8,9-Dehydroisolongifolene and 1,8-cineol were the major components of P. ruthenicum but β-caryophyllene, α-phellandrene, cis-β-farnesene and β-bisabolene were the main constituents of the fruit oil of P. verticillare.
The major compounds of leaf oil of P. verticillare were sabinene, trans-anethole and of P. petiolare were sabinene, alpha-pinene and limonene whereas leaf oil of P. ruthenicum, thymol and β-bisabulene were the main compounds.
In conclusion it seems that the components of P. ruthenicum and other Peucedanum oils are similar but the major compounds of them are different.
?This work was supported by grants from the National Research Center of Medical Sciences. The authors are grateful to Mr. Larijani for Gas Chromatography operation.
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