Chemical Constituents of the Essential Oil of Euphorbia teheranica Boiss., a Species Endemic to Iran

Journal of Essential Oil Research: JEOR, Jan/Feb 2004 by Feizbakhsh, Alireza, Bighdeli, Mohsen, Tehrani, Mohammad Saber, Rustaiyan, Abdolhossein, Masoudi, Shiva

Abstract

A water-distilled oil from aerial parts of Euphorbia leheranica Boiss. was analyzed by GC/MS. The oil consisted mainly of sesquiterpenes, and a small percentage of monoterpenes and aliphatic compounds. Eleinol (57.5%) was found to be the major constituent among the 24 compounds identified.

Key Word Index

Euphorbia teheranica, Euphorbiaceae, essential oil composition, elemol.

Introduction

Euphorbia teheranica Boiss. (Euphorbiaceae) is a plant widespread in the Tehran region and semi-desert areas of central Iran (1). To the best of our knowledge, except for two publications on the mild skin irritant activity and isolation of two novel pentacyclic diterpenoid esters of the cyclomyrsinane type and one tetracyclic diterpenoid ester of the myrsinane type of this plant (2), there has been no other report of any investigation of this species in the literature. Chemical investigation of some Euphorbia species have shown triterpenes, diterpenes and sesquiterpenes (3-7).

Experimental

Plant material was collected in july 1999 at flowering stage, 30 Km north ofTehran, Karadj area, between Maahshahr and Eshtehard. A voucher specimen has been deposited in the Herbarium of the Department of Botany, Shaheed Beheshti University, Tehran, Iran. The aerial parts (150 g) of the plant were dried at room temperature and hydrodistilled for 3 h using a Clevenger-type apparatus. The yield of the oil was 0.56%. The oil was analyzed by GC/MS using a HewlettPackard 5973 mass selective connected with an HP 6890 gas Chromatograph. The separation was achieved by capillary column, HP-5 MS (5% phenyl methyl siloxane) (30 m � 0.25 mm, film thickness 0.25 �m).

The column temperature was kept at 6O0C for 20 min and programmed to 220�C at a rate of 5�C/min, and kept constant at 220�C for 20 min. The flow rate of helium was 1 mL/min. MS was taken at 70 eV. Relative percentage amounts were calculated from TIC data by the computer.

The identification of the constituents was performed by comparing their mass spectra with those reported in the literature and with the library established by us, together with the retention indices (8).

Results and Discussion

The compounds identified in the oil are listed in Table I. In the oil, 22 compounds representing 93.4% of the oil were characterized. The oil was dominated by elemol (57.5%), with lesser amounts of [beta]-caryophyllene (8.1%) and caryophyllene oxide (7.8%). The other compounds were mostly presented in trace amounts. Thus, the oil of E. teheranica was rich in sesquiterpenes (86.1%), mostly oxygenated sesquiterpenes. The monoterpene fraction was relatively small, representing only (4.6%) of the total oil.

Acknowledgements

We (ire grateful to V. Mozaffarian for helpful assistance in collecting plant material and for botanical identification.

References

1. K.H. Rechinger, Euphorbia. In: Flora lranica, Euphorbiacea. No 6 Edits., K.H. Rechinger and I.C. Hedge, p33, Akademische Druck Verlagsanstalt, Graz, Austria (1964).

2. V.U. Ahmad and A.R. Jassbi, New diterpenoids from Euphorbia teheranica. J. Nat. Prod., 62, 1016-1018 (1999).

3. M. Ferriera, J.U. Loboand A.M. Wyler, Triterpenes of Euphorbia mellifera. Fitoterapia, 64, 377 (1993).

4. S. Matsunga, R. Morita, T. Ishida and M. Inove, The structure of spiro suopinanonediol, a triterpenoid bearing a novel skeletal system from Euphorbia supine. J. Chem. Soc., Chem. Commun., 16, 1128-1129 (1984).

5. J. Shi, Z. Jia and L. Yang, Diterpenoids from Euphorbia micractina. Phytochemistry, 33, 1554 (1993).

6. F. Jeske, J. Jakupovic and W. Berendsohn, Diterpenes from Euphorbiasegaieriena. Phytochemistry, 40, 1743-1750 (1995).

7. Y. Shi, L. Yang and Z. Jia, 2D NMR studies on diterpene ester and sesquiterpene glucoside from the genus Euphorbia. Bopuxue zazhi, 14, 217-221 (1997).

8. R.P. Adams, Identification of Essential Oil Components by Gas Chromatography/Mass Spectroscopy. Allured Publishing Corp., Carol Stream, IL (1995).

Alireza Feizbakhsh, Mohsen Bighdeli, Mohammad Saber Tehrani and Abdolhossein Rustaiyan*

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

Shiva Masoudi

Department ofChemistry, Central Tehran Branch, Islamic Azad University, Tehran, Iran

* Address for correspondence

1041 -2905/04/0001 -0040S6.00/0-� 2004 Allured Publishing Corp.

Received: February 2001

Revised: August 2001

Accepted: October 2001