Volatile Constituents of Meristotropis xanthioides Vassilez. and Lotus michauxianus Ser. from Iran

Journal of Essential Oil Research: JEOR, Nov/Dec 2006 by Rustaiyan, Abdolhossein, Khalilzadeh, Mohammad A, Eslami, Bahman, Masoudi, Shiva, Tajbakhsh, Mahmoud

Abstract

The water-distilled volatile oils from aerial parts of Meristotropis xanthioides Vassilez. and Lotus michauxianus Ser., two Paplionaceae species of Iran, were analyzed by GC and GC/MS. Myrcene (20.6 %), limonene (18.9%) and β-caryophyllene (11.8%) were the main components among the 22 constituents characterized in the oil of Meristotropis xanthioides, representing 94.0% of the total components detected. Ten compounds were identified in the oil of Lotus michauxanus representing 97.9% of the total oil with limonene (43.4%), (Z)-β-ocimene (18.9%) and α-eudesmol (15.9%) as main constituents. Both oils were richer in monoterpene hydrocarbons than sesquiterpenes.

Key Word Index

Meristotropis xanthioides, Lotus michauxianus, Papilionaceae, essential oil composition, myrcene, limonene, β-caryophyllene, (Z)-β-ocimene, α-eudesmol.

Introduction

The genus Merstotropis (Fam. Papilionaceae) is represented in the flora of Iran by only one species: M. xanthioides Vassilez (syn.: Glycyrrhiza triphylla Fisch. et C. A. Mey.) (1,2). The genus Lotus is represented in the flora of Iran by 10 species, of which L. laricus Rech. f, Aell. et Esfand. is an endemic plant (1,2). No studies on the chemical composition of oils of Meristotropis and Lotus species have previously been reported. Our study deals with the analysis of the oils of Meristotropis xanthioides and Lotus michauxianus that are found growing wild in Iran.

Experimental

Plant material: The aerial parts of two Papilionaceae species were collected during their flowering stage at the following places: 120 g of M. xanthioides was collected from Ashkhane, Province of Khorasan, Iran, in July 2002 and 80 g of L. michauxianus was collected from Haranj area, Taleghan, North of Tehran, Iran, in June 2002. Voucher (Numbers 4798 and 4591, respectively) specimens have been deposited at the Herbarium of the Research Institute of Forests and Rangeland (TARI), Tehran, Iran.

Oil isolation: The air-dried aerial parts of M. xanthioides and L. michauxianus were separately subjected to hydrodisitillation using a Clevenger-type apparatus for 3 h. After decanting and drying of the oils over anhydrous sodium sulfate, the corresponding oils were isolated in yield of 3.2% and 0.6% wt/wt, respectively.

Analysis: GC analysis was performed on a Shimadzu 15 A gas chromatograph equipped with a split/splitless injector 250°C and a flame ionization detector 250°C. N^sub 2^ was used as a carrier gas (1 mL/min) and the capillary used was DB-5 (50 m x 0.2 mm, film thickness 0.32 µm). The column temperature was kept at 60°C for 3 min and then heated to 220°C with a 5°C/min rate and kept constant at 220°C for 5 min. Relative percentage amounts were calculated from peak area using a Shimadzu C-R 4 A chromatopac without the use correction factors.

GC/MS: GC/MS analysis was performed using a Hewlett-Packard 5973 with an HP-5 MS column (30 m x 0.25 mm, film thickness 0.25 µm). The column temperature was kept at 60°C for 3 min and programmed to 220°C at a rate of 5°C/min and kept constant at 220°C for 5 min. The flow rate of helium as carrier gas was 1 mL/min. MS were taken at 70 eV. Identification of the constituents of each oil was made by comparison of their mass spectra and retention indices (RI) with those given in the literature and those authentic samples (3).

Results and Discussion

The composition of the oils of M. xanthioides and L. michauxianus are listed in Tables I and II, respectively, in which the percentage and retention indices of components are given. As it is shown, about 94.0% (22 compounds) of the oil of M. xanthioides and 97.9% (10 components) of the oil of L. michauxianus were identified. The oil of M. xanthioides consisted of seven monoterpene hydrocarbons (49.2%), 11 sesquiterpenes (41.3%) and four aliphatic esters (3.55%). Myrcene (20.65%), limonene (18.9%) and β-caryophyllene (11.8%) were the major components in this oil, followed by selina-3,7(ll)-diene (8.3%) and isolongifolene (7.1%). The oil ofL. michauxianus consisted of five monoterpene hydrocarbons (65.2%), four sesquiterpenes (29.6%) and one C^sub 13^-compound (3.1%). The major components of this oil was limonene (43.4% ), (Z)-β-ocimene (18.9%) and oc-eudesmol (15.4%) followed by gennacrene D (8.9%).

Acknowledgments

We are grateful to V. Mozaffarian (Research Institute of Forests and Rangelands, Tehran) for botanical identification.

References

1. K.H. Rechinger, Meristotropis, Lotus. In: Flora Iranica, Papillonaceae No. 157. Edits., K.H. Rechinger and I.C. Hedge, pp 170, 338, Akademische Druck and Veriagsanstalt, Graz, Austria (1982).

2. V. Moztfarian, A Dictionary of Iranian Plant Names. Farhang Moaser Publishers, Tehran, Iran (1996).

3. R.P. Adams, Identification of Essential OH Components by Gas Chromatography/Mass Spectroscopy. Allured Publ. Corp., Carol Stream, IL (1995).

Abdolhossein Rustaiyan*

Department of Chemistry, Science and Research Campus, I.A. University, P.O. Box 14515-775 Tehran, Iran

Mohammad A. Khalilzadeh and Bahman Eslami