Chemical Composition of Tanacetum larvatum Essential Oil

Chemical Composition of Tanacetum larvatum Essential Oil

Bulatovic, Vanja M

Abstract

Tanacetum larvatum (Gris.) Kanitz. is an endemic perennial herb distributed on a rocky terrain in Serbia (Kosovo), Montenegro and Albania. The chemical composition of T. larvatum essential oil, obtained from two locations in Montenegro (Mt. Komovi [Sample I] and Mt. Prokletije [Sample II]) was investigated. The oils obtained by hydrodistillation were analyzed by GC and GC/MS, on the two different capillary columns. The aerial parts of T. larvatum yielded 0.3% and 0.2% of a yellowish oil (Sample I and Sample II, respectively). About 40 compounds were identified, representing ~89% and 96% of the total oil content in the Samples I and II, respectively. trans-Sabinyl acetate was found to be the dominant component (51.2% and 69.7%). Among the rest of compounds β-pinene (7.7% and 4.3%) and camphor (6.3% and 4.3%) were the most abundant in both samples.

Key Word Index

Tanacetum larvatum, Asteraceae, essential oil composition, trans-sabinyl acetate.

Introduction

The genus Tanacetum L. (Asteraceae) comprises about 150 species, which are predominantly distributed in Europe and in Mediterranean. In the Flora of Serbia, this genus is represented with six species (1), of which T. parthenium (L.) Schultz Bip. (feverfew) is the most prominent and a known remedy used mainly in the prophylactics of migraine, as well as for the treatment of arthritis, fever, vertigo, menstrual disorders, stomach ache and psoriasis. These activities mainly have been attributed to sesquiterpene lactone parthenolide, which has antimigraine, anti-inflammatory, gastric anti-ulcer and antinociceptive activity, as described by Jain et al. (2), Petrovic et al. (3) and Mittra et al (4).

Tanacetum larvatum (Griseb. ex Pant.) Kanitz is endemic perennial herb, distributed on a rocky terrain in Serbia (Kosovo), Montenegro and Albania (1). Aljancic et al. (5) reported that in the aerial parts of this plant a significant amount of parthenolide, comparable to that found in T. parthenium, was determined. It is also shown that oral administration of the chloroform extract of T. larvatum caused a dose-dependent anti-inflammatory effect in the carrageenan-induced rat paw oedema test. When the plant extract was concomitantly given with indomethacin, the anti-inflammatory effect was slightly enhanced, and the gastric lesions were significantly reduced (3).

Regarding a high content of parthenolide (5), the antiinflammatory and gastroprotective activities (3), we investigated the chemical composition of T. larvatum essential oil, originating from two locations in Montenegro to explore the possibility of the existence of any limiting factors in the use of this plants extract as an alternative remedy, especially for the prophylactics of migraine. We compared the qualitative and quantitative composition of the oil of the two samples to determine any differences between them, and also comment on the differences between the oil composition of T. larvatum and that of T. parthenium (feverfew) studied by Kalodjera et al. (6), Lawrence (7), Kostic et al. (8) and Hendriks et al. (9). To the best of our knowledge the oil of T. larvatum has not been studied previously.

Experimental

Source: Aerial parts of T. larvatum were collected in July 2002, during the period of full flowering from two locations in Montenegro: Mt. Komovi (Sample I) and Mt. Prokletije (Sample II), altitude ca. 1900 m. The plant material was identified in Institute of Botany and Botanical Garden “Jevremovac”, University of Belgrade. Specimens have been deposited in the Herbarium of Botanical Garden “Jevremovac”, University of Belgrade, No. 10702 and 20702, respectively.

Oil isolation: The oils of each sample of T. larvatum were separately obtained by hydrodistillation using a Clevenger-type apparatus, according to the Proceeding I of the Yugoslavian Pharmacopoeia IV (10). Each oil was subjected to qualitative and quantitative analysis by GC and GC/MS, on the two different capillary columns.

Oil analysis: The GC analysis was carried out on a gas chromatograph HP 5890 series II, fitted with FID (300°C), split/spiritless injector (250°C) and column ULTRA 1 (cross-linked methylsilicone gum, 0.32 mm; length 25 m), carrier gas H^sub 2^ at 1 mL/min. The temperature program was 40°-280°C (2°C/min). GC/MS analysis was performed using a HP 5890 series II gas chromatograph with MS-detector HP 5971 A, operating at 70 eV, equipped with a split/splittless injector (250°C) and a 50 m x0.2 mm PONA-cross-linked methylsilicone gum column (film thickness 0.5 µm). Working conditions: injector temperature 250°C, detector temperature 280°C, column temperature 40°C (2 min), oven temperature 40°-260°C (heating rate 4°C/min) and then isothermal for 15 min. Carrier gas H^sub 2^, EI, 70 eV.

The identification of each compound was carried out by comparison of RRT and MS-data bank (NBS Library/Wiley) (11-15). The percentage composition of the oil (Table I) was computed from GC (FID) peak areas without using response factor correction.

Results and Discussion

The aerial parts of T. larvatum yielded 0.3% and 0.2% of a yellowish oil (Sample I and Sample II, respectively).

The results of GC and GC/MS analysis were summarized in Table I. Both oils were similar regarding their qualitative pattern, but displayed some quantitative differences. In the investigated oils, the oxygenated monoterpenes dominated (65.7% and 80.2% of the total amount, in Sample I and Sample II, respectively), followed by monoterpene hydrocarbons (17.9% and 13.4%). However, the sesquiterpene hydrocarbon content was different in the samples, with Sample I and Sample II containing 4.9% and 0.6%, respectively. The percentage of oxygenated sesquiterpenes were similar (0.9% and 0.8%), while the miscellaneous compounds were present only in traces. Sabinyl acetate was found to be the dominant component (51.2% and 69.7% in Sample I and Sample II, respectively). Among the rest of compounds, β-pinene (7.7% and 4.3%) and camphor (6.3% and 4.3%) were the most abundant. The analyzed oils differed significantly from the oil of feverfew, in which camphor and trans-chrysanthenyl acetate were the principal compounds (ca. 46-62% and ca. 14-18%, respectively) (6-9). The presence of trans-chrysanthenyl acetate might be important because of its activity as a prostaglandin synthetase inhibitor, which could be one of the reasons why the severity of migraines is purported to be reduced with the use of T. parthenium (9). trans-Chrysanthenyl acetate was not identified in our oils of T. larvatum. On the other hand, trans-sabinyl acetate has not been detected in feverfew oil (6-9).

In T. larvatum oil, originating from Mt. Komovi and Prokletije, Montenegro, a large amount of sabinyl acetate (ca. 51-70%) was determined. The presence ofthis toxic oxygenated monoterpene (16,17) in such a quantity in the investigated oil might be a limiting factor for medical application of this plant. Hence, further investigations have to be conducted to show whether the T. larvatum extracts could be used as herbal remedies with antimigraine, anti-inflammatory and gastroprotective effects.

Acknowledgments

The authors wish to thank Daniel Vincek from Botanical Garden, Kolasin, Montenegro for helping in collection of the plant material and Serbian Ministry of Science and Technology for financial support (Grant No. 568).

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Vanja M. Bulatovic*

Institute for Medicinal Plant Research “Dr. Josif Pancic”, Tadeusa Koscuska 1, 11000 Belgrade, Serbia and Montenegro

Vlatka E. Vajs and Ivana T. Aljancic

Institute for Chemistry, Technology and Metallurgy, Njegoseva 12, 11000 Belgrade, Serbia and Montenegro

Slobodan M. Milosavljevic and Dejan D. Djokovic

Faculty of Chemistry, University of Belgrade, Studentski trg 16, P.O. Box 158, 11000 Belgrade, Serbia and Montenegro

Silvana D. Petrovic

Institute of Pharmacognosy, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11221 Belgrade, Serbia and Montenegro

* Address for correspondence

Received: December 2003

Revised: March 2004

Accepted: May 2004

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