JEOR: Volatile Constituents of Three Umbelliferae Herbs: Azilia eryngioedes (Pau) Hedge et Lamond, Laser trilobum (L.) Borkh. and Falcaria falcarioides (Bornm. et Wolff) Growing Wild in Iran

Volatile Constituents of Three Umbelliferae Herbs: Azilia eryngioedes (Pau) Hedge et Lamond, Laser trilobum (L.) Borkh. and Falcaria falcarioides (Bornm. et Wolff) Growing Wild in Iran

Masoudi, Shiva

Abstract

The composition of the essential oils from three Umbelliferae species of Iran – Azilia eryngioedes (Pau) Hedge et Lamond, which is endemic to Iran, Laser trilobum (L.) Borkh. and Falcaria falcarioides (Bornm. et Wolff) Wolff – obtained by hydrodistillation were analyzed by GC/MS. Bornyl acetate (40.9%) was the main component among the 26 constituents characterized in the oil of A. eryngioedes, representing 93.8% of the total components detected. Eighteen compounds were identified in the oil of L. trilobum, representing 85.2% of the total oil, with β-caryophyllene (22.3%), myrcene (21.7%) and β-sesquiphellandrene (19.2%) as the major constituents. The oil of F. falcarioides was characterized by a higher amount of germacrene B (67.9%) among the 24 components comprising 97.6% of the total oil detected.

Key Word Index

Azilia eryngioedes, Laser trilobum, Falcaria falcarioides, Umbelliferae, essential oil composition, bornyl acetate, β-caryophyllene, myrcene, β-sesquiphellandrene, germacrene B.

Plant Name

Azilia eryngioedes (Pau) Hedge et Lamond (syn. Prangos eryngioides Pau), Lasertrilobum (L.) Borkh. (syn. Laserpitium trilobum L., Silertrllobum (L.) Crantz.), Falcaria falcarioides (Bornm. et Wolff) Wolff [syn. Pimpinellafalcarioides Bornm. et Wolff, Gongylosciadium falcarioides (Bornm. et Wolff) Rech. F., Scaligeria falcarioides (Bornm. et Wolff) Parsa.], fam. Umbelliferae (1,2).

Source

The aerial parts of three Umbelliferae species were collected during the flowering stage at the followingplaces: A. eryngioedes growing wild in Province of Chahar-Mahale Bakhtiarie, Iran, in July 2000; L. trilobum was collected from Chalouse, Province of Gillan, Iran, in June 2000; and F. falcarioides was collected from Urromieyeh, Province of Azarbaijan-Gharbi, Iran, in July 2000. Voucher specimens (numbers 1034,4325 and 3289, respectively) have been deposited at the Herbarium of the Research Institute of Forests and Rangelands (TARI), Tehran, Iran.

Plant Part

Air-dried aerial parts of A. eryngioedes, L. trilobum and F. falcarioides were separately subjected to hydrodistillation using a Clevenger-type apparatus for 3 h. After decanting and drying of the oils on anhydrous sodium sulfate, the corresponding oils were isolated in yield of 1.4%, 1.8% and 1.1% (w/w), respectively.

Previous Work

The genus Azilia is represented in the flora of Iran by only one species: A. eryngioedes (Pau) Hedge et Lamond, which is endemic to Iran and is widely distributed in Province of Lorestan and Chahar-Mahale Bakhtiarie in the south of Iran. No studies on the chemical composition of oils of Azilia species have previously been reported.

Laser trilobum (L.) Borkh. is the only species represented in the flora of Iran. Only a few reports on the chemical composition and analysis of oils of Loser species have been published (3-5).

The genus Falcaria is represented in the flora of Iran by two species: F. falcarioides (Bornm. et Wolff) Wolffand F. vulgaris Bornm. The chemical composition of the oil of F. vulgaris has been reported (6,7).

The essential oils of A. eryngioedes, L. trilohum and F. falcarioides have not been investigated up to now, so we decided to examine the oils.

Present Work

The oils were analyzed by GC/MS using a Hewlett Packard 5973 mass selective detector connected with an HP 6890 gas Chromatograph. The separation was achieved by use of an HP 5MS (5% phenylmethylsiloxane) capillary column (60 m × 0.25 mm, film thickness 0.25 µm). The column temperature was held at 60°C for 3 min and then programmed to 220°C at a rate of 6°C/min, and then kept constant at 220°C for 3 min. Helium was used as the carrier gas at a flow rate of 1 mL/min. MS was taken at 70 eV. Identification of the constituents was made by comparing their mass spectra and retention indices with those given in the literature and authentic samples (8). Relative percentage amounts were calculated from TIC data by computer. The compounds identified in the oil of A. eryngioedes, L. trilobum and F. falcarioides are listed in Tables I, II and III, respectively.

Acknowledgments

We are grateful to V. Mozaffarian for assistance in botanical identification.

References

1. K.H. Rechinger, Azilia, Laser, Falcaria. In: Flora lranica Umbellifera. No. 162, Edits., K.H. Rechinger and I.C. Hedge, pp. 386, 440, 308, Akademische Druck and Verlagsanstalt, Graz, Austria (1987).

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

3. G. Appendino, M.G. Valle and R Gariboldi, Sesquiterpene lactones from Laserpitium halleri. Phytochemistry, 26, 1755-1757 (1987).

4. K. Borg, K. Anna, I. Valterovaand LA. Nilsson, Volatile compounds from flowers of six species in the family Apiaceae. Phytochemistry, 35, 111-119 (1994).

5. R. Chizzola, J. NovakandC. Franz, Fruit oil of Laserpitium siler L. grown in France. J. Essent. oil Res., 11, 197-198 (1999).

6. J. Gudej, Essential oil of Falcaria vulgaris. Acta Pol. Pharm., 34, 299-304 (1977).

7. R. Zielinska-Sowicka and J. Gudej, Chemical composition of Falcaria vulgaris roots. Acta Pol. Pharm., 36, 353-358 (1979).

8. R.P. Adams, Identification of Essential oil components by Gas Chromatography/ Mass Spectroscopy. Allured Publ. Corp., Carol Stream, IL (1995).

Shiva Masoudi and Nazak Ameri

Department of Organic Chemistry and Medicinal Plants, Institute of Pure and Applied Sciences, I.A.U., Central Tehran Branch, Tehran, Iran

Abdolhossein Rustaiyan,* Mehran Moradalizadeh and Parviz Aberoomand Azar

Department of Chemistry, Science if Research Campus, Islamic Azad University, PO Box 14515-775, Tehran, Iran

* Address for correspondence

Received: April 2002

Revised: August 2002

Accepted: October 2002

Copyright Allured Publishing Corporation Jan/Feb 2005

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