Composition of the Essential Oils of Tordylium trachycarpum (Boiss.) Al-Eisawi et Jury and Tordylium hasselquistiae DC. Growing in Turkey
Özek, Temel
Abstract
The essential oils obtained by hydrodistillation from fruits of Tordylium trachycarpum (Boiss.) Al-Eisawi et Jury and Tordylium hasselquistiae DC. (Apiaceae) were analyzed by GC and GC/MS. In total, fifty-three compounds were characterized, representing 99.5% of the oil and sixty-one compounds were characterized, representing 98.8% of the oil of T. trachycarpum and T. hasselquistiae, respectively. The main constituents were octyl octanoate (79.9%), octanol (11.0%) and octanoic acid (2.9%) in T. trachycarpum; and octyl hexanoate (72.7%), octyl octanoate (12.7%) and octanol (3.3%) in the oil of T. hasselquistiae.
Key Word Index
Tordylium trachycarpum, Tordylium hasselquistiae, Apiaceae, essential oil composition, octanol, octyl hexanoate, octyl octanoate.
Introduction
The genus Tordylium L. (Syn.: Hasselquistia L., Condylocarpus Hoffm., Ainsworthia Boiss., Synelcosciadium Boiss.), is represented by 15 species in Turkey (1-2). There are a few previous papers on phytochemical (flavonoids, coumarins) and biological activity studies (antioxidant, antibacterial, cytotoxic properties) on some Tordylium species (3-6). There is a report on T. apulum L. as die most preferred pollen source for honey bees (7).
There are a few papers on the essential oil studies of Tordylium species (5, 8-10). In die oil of T. apulum obtained from aerial parts, α-humulene (28.7%), octyl hexanoate (11.7%), farnesyl acetone (9.8%) were reported as major components (5).
In the fruit oil of T. apulum the major constituents were found as octyl hexanoate (44.0%), octyl octanoate (34.5%) and octanol (16.5%) (8).
In the oil from fruits of a recently described endemic species, T. ketenoglui H. Duman et A. Duran, the main constituents were octyl octanoate (28.9%), octanol (11.6%) and bornyl acetate (7.2%) (9-10).
The main constituents in the fruit oils of T. pestalozzae Boiss., T. pustulosum Boiss. and T. lanatum (Boiss.) Boiss were characterized as octyl hexanoate (56.0%), octyl octanoate (15.7%), octanol (14.5%), hexadecanoic acid (6.0%); octyl hexanoate (68.8%), octyl 2-methylbutyrate (17.8%), octanol (4.2%); octyl hexanoate (58.8%) and octanol (21.5%), respectively (11).
As a continuation of our research into essential oils of the family Umbelliferae, the GC and GC/MS analyses of the oils of two Tordylium species have been carried out. To die best of our knowledge, there is no previous report on the oil compositions of T. trachycarpum and T. hasselquistiae.
Experimental
Plant Material: Fruits of T. trachycarpumwere collected in April, 2004 along Adana-Antakya highway. Fruits of T. hasselquistiae were collected in April, 2004 in Hatay province, on a way between Belen and Kici, in area enclosed by olive trees. Both of the Tordylium species were identified by Prof. H. Duman. Voucher specimens have been deposited at the Herbarium of the Faculty of Pharmacy of Ankara University (AEF 23143 and AEF 23146, respectively).
Isolation of the Essential Oils
Hydrodistillation (HD): The dried crushed fruits of T. trachycarpum and T. hasselquistiae were subjected to hydrodistillation for 3 h using a Clevenger-type apparatus. The oil yields (v/w) on moisture free basis were 1.85% and 0.5%, respectively.
Gas Chromatography (GC) and Gas Chromatography – Mass Spectrometry (GC/MS) analysis: The same column and analysis conditions were used for both GC and GC/M S . The essential oil was analyzed using an Agilent 6890N Network GC System widi 5973 Network Mass Selective Detector simultaneously. An HP-Innowax FSC column (60 m x 0.25 mm with 0.25 µm film diickness) was used for separation of components in the oil. Helium (0.8 mL/min) was used as carrier gas. The GC oven temperature was kept at 60°C for 10 min and programmed to 220°C at a rate of 4°C/min and then kept constant at 220°C for 10 min and programmed to 240°C at a rate of 1°C/min. The Mass range was recorded at m/z 35 to 450. The split ratio was adjusted at 50:1. The injector temperature was at 250°C. MS were recorded at 70 eV. FID detector temperature was 250°C. n-Alkanes were used as reference points in the calculation of relative retention indices (RRI).
Identification of Compounds: The components of essential oils were identified by comparison of dieir mass spectra with those in the Baser Library of Essential Oil Constituents, Wiley GC/M S Library, Adams Library, MassFinder Library and confirmed by comparison of their retention indices.
Results and Discussion
The list of compounds identified in die hydrodistilled oils of T. trachycarpum and G. hasselquistiae with their relative percentages, retention indices and percentage amounts of compound classes are given in Table I. Two Tordylium species examined here showed small differences, mainly in quantitative characters. In total, fifty-four compounds and sixty-one compounds were characterized, representing99.5% and 98.8% of the oils of T. trachycarpum and T. hasselquistiae, respectively. Esters (81.4% and 85.8%, resp.) were found to be the most abundant group detected in die oils, widi octyl octanoate (79.9% and 12.7%, resp.) and octyl hexanoate (1.3% and 72.7%, resp.) as the major constituents. They were followed by alcohols (11.0% and 3.4%, resp.) widi octanol (11.0% and 3.3%, resp.) as die major component. Acids (3.3%) were also among the compound classes characterized in the both oils, with octanoic acid (2.9%) and hexadecanoic acid (3.0%) as the main representatives, in the oils of T trachycarpum and T. hasselquistiae, respectively. Alkanes (3.0%) were also present in the oil of T. hasselquistiae while in the oil of T. trachycarpum this group was detected only as a minor percentage (0.1%). Aldehydes were present in scarce amounts (1.0% and 0.4%) in the oils. Monoterpenes and sesquiterpenes accounted for 1.1% and 1.5% for T. trachycarpum and .1.8% and 1.1% for T. hasselquistiae, respectively.
After a comparative appreciation of the chemical profiles of Tordylium fruit oils reported earlier, it can be considered, octanol and octyl esters are the predominant components of the fruit oils of diese species.
Acknowledgments
Authors are grateful to Hay ri Duman for identification of plant materials at Gazi University, Faculty of Science and Letters, Department of Biology, 06500 Ankara, Turkey.
References
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Temel Özek,* Mine Kürkcüoglu and K. Hüsnü Can Baser,
Department of Pharmacognosy, Faculty of Pharmacy, Anadolu University 26470 Eskkehir, Turkey
AlevTosun,
Department of Pharmacognosy, Faculty of Pharmacy, Ankara University 06100 Tandogan, Ankara, Turkey
* Address for correspondence
Received: March 2006
Accepted: June 2006
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