The genus Tripleurospermum Sch. Bip. belongs to the Compositae family, tribe Anthemideae, and is represented by about 30 species which are distributed in temperate regions of the northern hemisphere of the world [1]. In Iran, six species of Tripleurospermum can be found [2]. In the Anthemideae tribe, this genus is characterized by the presence of luteolin 7-glucoside [3], and in a recent chemotaxonomic survey of Anthemideae flavonoids, distinctive constituents of Tripleurospermum confirmed its treatment as a separate genus [4].

Tripleurospermum disciforme, the subject of this article, is a widespread biennial species which can be found almost everywhere in farmlands and gardens as a weed. It is called “Babuneh” in Persian and is used as a tranquilizer, gastrotonic, antihemorrhage, and hair tonic [5]. Extracts of this plant show excellent antioxidant activity, and a new dioxaspiran derivative was isolated from it [6]. Its crude extract also shows considerable in vitro antifungal activity against several fungal strains [7].

Data on the constituents of Tripleurospermum disciforme essential oil are shown in Table 1. Thirty-nine components representing 81.6% of the total oil were identified. According to Table 1, sesquiterpenes are the dominant compounds (57.5%), and among these, sesquiterpene hydrocarbons are the major compounds (45.5%). Monoterpenoids are present in trace quantities in this oil. The first three major compounds of this oil are p-methoxy- β-cyclopropylstyrene (18.8%), (E)-β-farnesene (15.6%), and β-sesquiphellandrene (15.4%). The two first compounds were also detected in the chloroform extracts of flowers, stems, and roots of T. callosum (Boiss. & Helder) E. Hossain, but in amounts less than 1% [8].

Table 1. The Chemical Constituents (%) of the Oil of Tripleurospermum disciforme
Full size table

The aerial parts of Tripleurospermum disciforme were collected in 31 May 2006 at the full flowering stage from Dehbid in Fars province of Iran. The voucher specimen has been deposited at the Herbarium of Shiraz University, Department of Botany. The aerial parts of the specie were air-dried. The oil was obtained by hydrodistillation using a Clevenger-type apparatus for 4 h. The yield of oil was 0.16% (w/w) 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.

GC analysis was carried out using a Varian GC 3600 chromatograph with a DB-5 column (30 m × 0.25 mm; 0.25 μm film thickness). The oven temperature increased from 60 – 240°C at 3°C/min, and the injector and detector temperatures were 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 machine operating at 70 eV ionization energy, equipped with a HP-5 capillary column (phenyl methyl siloxane, 30 m × 0.25 mm; 0.25 μm film thickness) with He as the carrier gas and a split ratio of 1:20. Retention indices were determined by using the retention times of n-alkanes that had been injected after the oil under the same chromatographic conditions. The retention indices for all the components were determined according to the Van Den Dool method using n-alkanes as standard [9]. The compounds were identified by comparison of their retention indices (RRI, HP-5) with those reported in the literature and by comparison of their mass spectra with the Wiley and Mass finder 3 libraries or with the published mass spectra [10, 11].