Constituents of the essential oil of Tanacetum lingulatum (Boiss.) Bornm.

Journal of Essential Oil Research: JEOR, Mar/Apr 2003 by Afsharypuor, Suleiman, Jahromy, Maryam Mosaffa

Abstract

The composition of the essential oil of Tanacetum lingulatum (Boiss.) Borm. (Asteraceae) was investigated by capillary GC, GC/MS and IH-NMR. The major constituents were 1,8-cineole (18.6%) and camphor (13.9%).

Key Word Index

Tanacetum lingulatum, Asteraceae, essential oil composition, 1,8-cineole, camphor.

Introduction

Tanacetum lingulatum (Boiss.) Bornin. (syn.: Pyrethruin lingulatum Boiss.), a species of the section Xylanthemum (Asteraceae), is a plant growing wild in different parts of Isfahan and Kerman provinces (Iran). It is a perennial, slightly woody herb covered with forked hairs of appressus texture. The stem of the plant is rigid, erect and angled, and is 20-40 cm in length. The leaves are lanceolate or ligulate-lanceolate, with an obtuse or slightly acute apex. The flowers are yellow, and each flower forms a narrow tube 3 cm in length (1).

Tanacetum species are reported to possess anthelmintic, carminative, antispasmodic and anti-migraine properties, and a repellent effect on the Colorado beetle (2-4).

The compositions of the oils of other Tanacetum species growing in other parts of the world have been reported (2,57). To the best of our knowledge, this is the first report on the oil constituents of T. lingulatum growing in Iran.

Experimental

Plant material: Aerial parts of flowering T lingulatum were collected in June 1999 from a wild population growing in Isfahan (Iran) at an altitude of 1,710 in. The plant was identified in the Botany Department of the Faculty of Sciences at the University of Isfahan (Iran), and a voucher specimen was deposited in the Herbarium of the Faculty of Pharmacy and Pharmaceutical Sciences at the Isfahan University of Medical Sciences (Iran).

Oil preparation: The powdered air-dried plant material was steam distilled for 4 h. A pale greenish yellow oil (0.32% v/w) was obtained, which exhibited the following physical properties: eta^sup 25^:1.472; d^sup 25^:0.850.

Oil fractionation: The oil was subjected to column chromatography using an MN kieselgel 60 (230-400 mesh). Elution was performed with petroleum ether and increasing amounts of diethyl ether. The collected fractions were analyzed by GC using a Perkin Elmer 8500 apparatus equipped writh a Chrom Pack 3% silicone OV-101 stainless steel packed column (2 m x 2 mm). Oven temperature was programmed from 60 deg -275 deg C at 15 deg C/min; injector temperature was 275'C; detector temperature was 280 deg C; flow rate of the carrier gas (He) was 13 cm^sup 3^/min.

The major components (i.e. 1,8-cineole and camphor), as well as terpinen-4-ol, were further analyzed by GC/MS using the same column and conditions mentioned in the GC/MS analysis.

GC/MS analysis: Analysis of the oil was performed on a Hewlett Packard 6890 GC/MS instrument under the following conditions: injection of 0.1 (mu)L sample, HP-5 MS capillary column (30 in x 0.25 ram, coating thickness 0.25 Vim); carrier gas (He) flow rate was 2 mL/min; injector temperature was 250 deg C; temperature programmed run was: 60 deg -275 deg C at 4 deg C/ min; mass spectra: electronic impact; ionization potential: 70 eV; ion source temperature: 250 deg C; ionization current: 1,000 (mu)A; resolution: 1,000; mass range: 30-300.

Identification of the constituents was based on computer matching against the library spectra (Library Database Wiley 275), their retention indices with reference to an ii-alkane series in a temperature programmed run, and comparison of the mass spectra with the literature data (8,9).

The IH-NMR spectra of the major components were corded on a Brucker-80 spectrometer using CDCl^sub 3^ as solvent and TMS as internal standard.

Results and Discussion

Fifty-six constituents representing 98. 1% of the total oil were identified (Table I). The main constituent of the oil was 1,8-cineole (18.6%). The presence of considerable amounts (8-14%) of 1,8-cineole have also been found in two samples of Dutch Tansy (Tanacetum vul,are L.) (2). However, it was found only in trace amounts in the oil of T vulgare growing spontaneously in Argentina as well as in the oil of Dutch T parthenium L. Schults-Bip. (5, 10).

The other major constituent of the examined oil in this study was camphor (13.9%). It was the main constituent of the oils isolated from English and Dutch samples of T vulgare as well as that of a Belgian sample of T parthenium (5,11). The oils of two samples of Dutch T vulgare were also found to contain a high proportion of camphor (24-42%) (2). However, the oil of T. longifolium Wall. growing wild in Himachal Pradesh (India) was found to contain low amounts of this monoterpenoid compound (0.19%) (6).

The oil isolated from T. lingulatum contained a-terpineol (3%). It was also only identified in small amounts (

Acknowledgments

We are grateful to M.R. Rahiminejad (Botany Department, Faculty of Sciences, University of Isfahan) for identification of the plant material and Armita Jamshidi for her help in analyzing the oil samples by GC and GC/MS methods.

References

1. K.H. Rechinger, Flora Iranica. No. 158: Compositae, VI-Anthemideae, p. 88, Akademische Druk-u. Verlagsanstalt, Graz, Austria (1986).