Constituents of the Volatile Oil of Ferulago angulata (Schlecht.) Boiss. from Iran

Constituents of the Volatile Oil of Ferulago angulata (Schlecht.) Boiss. from Iran

Javidnia, K

Abstract

The aerial parts of Ferulago angulata (Schlecht.) Boiss. were hydrodistilled by use of a Clevenger-type apparatus. The yield of the oil was 0.5%. The oil was analyzed by GC and GC/MS. Sixty-two components representing 89.7% of the oil were identified. The main components of the oil were (Z)-β-ocimene (35.5%), terpinolene (5.7%) and α-phellandrene (5.4%)

Key Word Index

Ferulaogo angulata, Apiaceae, essential oil composition, (Z)-β-ocimene.

Introduction

Ferulago is a genus belonging to the Apiaceae family. It has 35 species, of which seven grow wildin Iran. Ferulago angulata is one of these species that are found in their natural state in Iran. (1). The oils of Ferulago species have been the subject of previous studies. Ferulagone and ent-3β-hydroxy-13-epi-manoyl oxide were isolated as the main components of F. thirkeana and F. thyrsiflora, respectively (2,3). The major constituent of the following oils indicated in parenthesis: F. asparagifolia (2,3,6-trimethyl benzaldehyde), F. aucheri, F, mughlae F. sandrasica and F. phialocarpa (α-pinene), F. confusa (2,5-dimethoxy-p-cymene), F. sylvatica and F. idaea (p-cymene), F. macrosciadia (methyl carvacrol), F. silaifolia and F. galbanifera (frans-chrysanthenyl acetate), F. trachycarpa (γ-terpinene) and F. humilis and F trachycarpa [(Z)-β-ocimene] (4-7). α-Pinene, myrcene and (Z)-β-ocimene were the main components of the oil of F. nodosa, while α-pinene and p-cymene were present as main compounds of F. sylvatica (8,9). In a previous study, α-phellandrene and β-phellandrene were identified as the main components of the oil of F angulata (10). In this study we report the constituents of the oil of the aerial parts of F. angulata with different chemical constituents.

Experimental

Plant material: Aerial parts of the plant were collected in June 2003, from Dena mountain, 2650 m elevation, at the time of flowering. The plant was identified by the Department of Botany, Research Center of Natural Resource and Animal Husbandry. The specimen (herbarium No. 4452) has been deposited in the Herbarium of the Research Center of Natural Resource and Animal Husbandry.

Analysis of the oil: The aerial parts were air dried at ambient temperature in the shade and steam distilled by a Clevenger-type apparatus for 4 h. The yield of oil was 0.5% and the color of the oil was yellow. It was dissolved in n-hexane (Merck), dried over anhydrous sodium sulfate and stored at 4°-6°C until analysis.

GC analysis was carried out using a Varian GC 3600 (FID) Chromatograph with DB-5 column (30m x 0.25 mm, 0.25 µm film thickness). Oven temperature was performed as follows: 60°-260° C at 3°C/min, injector and detector temperatures, 240°C and 250°C, respectively. Quantitative data were obtained from electronic integration of peak areas without the use of correction factors.

GC/MS analysis was carried out using a Hewlett-Packard 6890 operating at 70 eV ionization energy, equipped with a HP-5 capillary column (phenyl methyl siloxane, 30 m x 0.25 mm, 0.25 µm film thickness) with He as the carrier gas and split ratio 1:20. Retention indices were determined by using retention times of n-alkanes that has been injected after the oil under the same Chromatographie conditions. The retention indices for all the components were determined according to the Van Den Dool method using n-alkanes as standard (11). The compounds were identified by comparison of retention indices (RRI, HP-5) with those reported in the literature and by comparison of their mass spectra with the Wiley library or with the published mass spectra (12,13).

Results and Discussion

The oil of the aerial parts of Ferulago angulata was examined by GC and GCVMS. The constituents of the oil are presented in Table I. Sixty-two compounds representing 89.7% of the oil have been identified. The oil consisted mainly of monoterpene hydrocarbons (62.6%). Oxygenated monoterpenes and sesquiterpenes were present in the oil with 17.2% and 10%, respectively. (Z)-β-Ocimene (35.5%), terpinolene (5.7%) and α-phellandrene (5.4%) were the main components of the oil. In previous study the main compounds of the oil were α-phellandrene (13.8%) and β-phellandrene (32.0%), which present in the oil of this study with 5.4% and 3.4%, respectively (9). The main component of the oil (Z)-bgr;-ocimene (35.5%) was not present in the oil of aerial parts in previous study, while it was the main component of the oil of E humilis, F. trachycarpa and F. nodosa (4,7,8). The place and the elevation of collection of the plant between two studies were different and it can cause the variation in the constituents of the oils.

Acknowledgments

This work was supported by a grant from the Technology Council of Shiraz Province and Besearch Council of the Medical Sciences University of Shiraz.

References

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K. Javidnia* and R. Miri

Medicinal & Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran

N. Edraki and M. Khoshneviszadeh

Dept. of Medicinal Chemistry, Faculty of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran

A. Javidnia

Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

* Address for correspondence

Received: July 2004

Revised: October 2004

Accepted: June 2005

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