Pimpinella Species Research Articles

Gas chromatographic–mass spectrometric analysis of essential oils from Pimpinella species gathered from Central and Northern Turkey

Essential oils from 15 Pimpinella species were analyzed by gas chromatography (GC) and gas chromatography –mass spectrometry (GC–MS) techniques. One species, Pimpinella anisum, in which only fruits were evaluated, was also included in the study. A total of 140 different compounds were identified and significant qualitative and quantitative differences were observed among the samples. Pimpinella essential oils were characterized as having mono-, sesqui- and trinorsesquiterpenoids, propenylphenols, and pseudoisoeugenols. Trinorsesquiterpenoids and phenylpropanoids appear to be chemical markers of Pimpinella species analyzed thus far. Essential oils obtained from Pimpinella roots share the same principal compound, epoxypseudoisoeugenyl-2-methylbutyrate at concentrations from 20 to 82.6%.

Bioactive Constituents from TurkishPimpinella Species

A new 'phenylpropanoid', 4-(3-methyloxiran-2-yl)phenyl 2-methylbutanoate (1), a new trinorsesquiterpene, 4-(6-methylbicyclo[4.1.0]hept-2-en-7-yl)butan-2-one (2), and eight known compounds (3-10) were isolated from the essential oils of several Pimpinella species growing in Turkey. The structures of the new compounds were determined by 1D- and 2D-NMR analyses. The absolute configuration of 1 was established via comparison of its optical rotation with that of 'epoxypseudoisoeugenyl 2-methylbutyrate' (11), the absolute configuration of which was determined by chemical degradation and an appropriate Mosher ester formation. Direct bioautography revealed antifungal activity of 1 and 11 against Colletotrichum acutatum, C. fragariae, and C. gloesporioides. Subsequent evaluation of antifungal compounds in a 96-well microtiter assay showed that compounds 1 and 11 produced the most-significant growth inhibition in Phomopsis spp., Colletotrichum spp., and Botrytis cinerea. Compounds 1 and 6 displayed antimicrobial activities against Mycobacterium intracellulare, with IC50 values of 2.78 and 1.29 microM, respectively.

Estrogenic activity of isolated compounds and essential oils of Pimpinella species from Turkey, evaluated using a recombinant yeast screen.

Several plants and plant-derived pure compounds, designated as phytoestrogens, have been reported to cause estrogenic effects. They have been used for alleviation of menopausal symptoms, prevention of osteoporosis, heart disease and cancer. There is an increased interest in studying phytoestrogens such as isoflavones and lignans for their use as replacements for synthetic estrogens. In this study, the estrogenic activity of essential oils of eleven Pimpinella species and the compounds isolated from these species were evaluated using the yeast estrogen screen (YES) assay. The essential oils containing (E)-anethole as major compound showed estrogenic activity in the YES assay, except for the aerial parts without fruits of P. anisetum and P. flabellifolia. The percent maximal response produced by most anethole-containing oils was 30-50%. Fruits of P. isaurica and P. peucedanifolia were estrogenic in spite of the absence or trace amount of anethole, respectively. This study indicates that the estrogenic activity of Pimpinella oils is not solely due to the presence of anethole. Components other than anethole may be responsible for contributing towards the estrogenic activity. The essential oils from different species varied in their estrogenic potencies (relative potency from 8.3 x 10(-8) to 1.2 x 10(-6) compared to 17 beta-estradiol) and among the different plant parts, the fruit oils of most species were estrogenic followed by the aerial parts without fruits and the root oils and their EC50 values varied from 45 micrograms/mL to 650 micrograms/mL.

Reinvestigation of the Phenylpropanoids from the Roots of Pimpinella Species

The roots of Pimpinella saxifraga and P. major (umbelliferae) were reexamined for their “isoeugenol” derivatives. According to high field 1H-NMR, 13C-NMR, as well as MS-studies, the hitherto described substitution pattern (4-OH, 5-OMe) must be revised to be 2-OH and 5-OMe. A fatty acid ester of a phenylpropanoid was found, its structure was elucidated by 2D-1H-NMR (1H-1H correlated COSY).

Occurrence of 1,5-dimethylcyclodeca-1,5,7-triene (Pregeijerene) in Pimpinella species and chemosystematic implications

Abstract The essential oils from fresh roots of 66 species, representing 39 general of the Apiaceae (Umbelliferae), subfamily Apioideae, were surveyed for pregeijerene. Of all plants examined, only the 11 species of the genus Pimpinella were shown to contain pregeijerene. According to its extremely restricted occurrence in the Apiaceae, its possible taxonomic value with regard to the definition of the genus Pimpinella is discussed.