J Pharm Pharmaceut Sci (www.ualberta.ca/~csps) 5(3):231-233, 2002

 

Fatty acid composition of Dracunculus vulgaris Schott ( Araceae ) seed oil from Turkey.

Serap Saglik1
Istanbul University, Faculty of Pharmacy, Department of Analytical Chemistry, Beyazt, Istanbul, Turkey

Kerim Alpnar
Istanbul University, Faculty of Pharmacy, Department of Pharmaceutical Botany, Beyazt, Istanbul, Turkey

Sedat Imre
Istanbul University, Faculty of Pharmacy, Department of Analytical Chemistry, Beyazt, Istanbul, Turkey

Received 17 June 2002, Revised 26 August 2002, Accepted 26 August 2002

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Abstract
 

Dracunculus vulgaris Schott is only one taxon of the genus Dracunculus (Araceae ) in Turkey. The tubers and the fruits with the seeds of D . vulgaris have long been in use for the treatment of rheumatism and hemorrhoids, respectively. The fatty acid composition of D . vulgaris seeds have been analyzed as their methyl esters by GC and GC-mass spectrometry. C16:0, C16:1n-7, C18:1n-9, C18:1n-7 (cis -vaccenic acid), C18:2n-6 and 13-phenyl tridecanoic acids were found to be the main components in the seed oil.

Introduction

The genus Dracunculus (Araceae ) is represented with only one taxon (D . vulgaris Schott) in Turkey. Having large tuberous roots, spotted leaf sheats, tall scape (up to 150 cm), deeply pedatisect vigorous leaves, dark reddish purple spadix (up to 60 cm) and spathes (up to 40 cm) D . vulgaris grows in mainly in western part of the country. It flowers in May and June and the reddish berry type fruits ripen in July. It is the largest and the most showy wild aroids of Turkey (1). In Turkey D. vulgaris has many vernacular names. Among them "yilan bacagi", "yilan biçagi", "yilan burçagi", "yilan kamasi" are in common use. Meanwhile the tubers are used external in the treatment of rheumatism, the fruits with the seeds are used internal in the treatment of hemorrhoids, although the toxic properties of the plant are well known (2).

cis -Vaccenic acid was determined in some different Umbelliferae seed oils (3) and also pulp lipids of commonly available fruits (4). 13-Phenyltridecanoic acid in seed lipids of some Aroids was investigated (5) and we studied the fatty acid composition of Arum italicum Miller seed oil in our previous work (6). Occuring the unusual fatty acids and/or high concentrations of the usual fatty acids in the seeds are chemotaxonomically important.

Nobody has investigated the potential chemotherapeutic constituents and also chemotaxonomy of D. vulgaris in Turkey until now. Therefore in this study the fatty acid composition of the seed oil was investigated as methyl esters by GC and GC-mass spectrometry. This is the first report on fatty acid composition, 13-phenyltridecanoic acid content and high amounts of cis-vaccenic acid of D. vulgaris Schott seeds from Turkey.

MATERIALS AND METHODS

Dracunculus vulgaris Schott ripe (mature) fruits were collected and identified in September, 2001 in the region of Gökçeada (Imroz), Çanakkale in Turkey.

Dried and crushed seeds were extracted with petroleum ether (40-60°C) and the seed oil was weighed after the evaporation. Fatty acid methyl esters were prepared with 20% BF3/MeOH at room temperature for 2 hours following by 78°C for 3 hours (7) and extracted with petroleum ether (40-60°C).

The analysis of fatty acid methyl esters were performed by a gas chromatograph (Shimadzu GC-14 A) on a TC-WAX (GL Sciences Inc.) column (30 m x 0.25 mm i.d., 0.25mm film thickness) using nitrogen (1 kg/cm2 ), equipped with a FID (260°C) and a split/splitless injector (250°C, split 1:20). The temperature was programmed from 170-225°C at 1°C min-1 followed by a final hold of 25 min. Identification of the methyl esters were made by comparison of retention times of standard fatty acid methyl esters (Applied Science Laboratories Inc. and Sigma Chemical Co.) and a normalization technique was used for quantitation with a computer program Class CR-10 (Shimadzu Co.).

Gas chromatography-mass spectrometric analyses were made by GC-MS equipment (HP 6890 Series GC System) with mass selective detection. A J&W WAX (GL Sciences Inc.) column (30 m x 0.25 mm i.d., 0.25mm film thickness) was used, and the temperature was programmed from 150-230°C at 2°C min-1 with an initial hold of 4 min and a final hold of 36 min. The carrier gas was helium (1 mL min-1) and the split ratio was 1:50. The injection port was held at 250°C and the detector at 300°C.

RESULTS AND DISCUSSION

The total lipid content of Dracunculus vulgaris Schott seed was found as 1.18 ± 0.02% (n=3) per dry weight. The fatty acid composition of the seed oil was determined by capillary gas chromatography and the results are shown in Table 1.
 

Table 1: Fatty acid composition of the oil from seeds of Dracunculus vulgaris Schott (n=9).

 

There were twentyone fatty acids identified by comparison with the fatty acid methyl ester standards. The structure of the unknown fatty acid was further supported by GC-mass spectrometry. The data indicated that this fatty acid had an aromatic phenyl ring, one carboxyl group and a Mr of 290 and it is called as 13-phenyltridecanoic acid (5,6). The major fatty acids were palmitic acid (15.33%), oleic acid (18.06%), cis-vaccenic acid (11.02%) and linoleic acid (23.21%), followed by palmitoleic acid (4.87%), stearic acid (3.27%) and 13-phenyltridecanoic acid (9.47%). cis -Vaccenic acid was determined in some different Umbelliferae seed oils (3) and also pulp lipids of commonly available fruits (4). In seed lipids it is generally found in lower concentrations (0.5-2.0%) (7) although its higher amounts in some species (7-9). In this study it was found as 11.02% and this value is very high comparing the general literature findings (7). On the other hand thirteen fatty acids were detected in small quantities (0.15-2.07%) and also two fatty acids (<0.10% for each other). There were 11 saturated fatty acids in the sample. All of them were detected in small quantities (<0.10%-1.30%) except C16:0 (15.33%) and C18:0 (3.27%) and the total percentage was 22.69. Regarding the monounsaturated fatty acids, oleic acid (18.06%) was the predominant fatty acid in them and the total percentage was 34.79. In the polyunsaturated fatty acids, C18:2n-6, C18:3n-3, and 13-phenyltridecanoic acid levels were in the range of 2.07 and 23.21% except C20:2n-6 (<0.10%). The percentage of 13-phenyltridecanoic acid (9.47%) was found a little lower than that of the literature findings (5). Considering the results obtained in this preliminary study, it is noticeable that the seed oil has contained 13-phenyltridecanoic acid and also higher amounts of cis -vaccenic acid and it would be interesting to investigate all Turkish Aroids for therapeutic and also chemotaxonomic purposes.

ACKNOWLEDGEMENTS

We gratefully thank Prof. Dr. Kasim Cemal Guven for technical cooperation.

This work was supported by The Research Found of the University of Istanbul.

References

  1. Mill, RR., Dracunculus Schott in Flora of Turkey and the East Aegean Islands. Vol. 8, University Press, Edinburg, pp 62-63, 1984.

  2. Alpinar, K. and Mericli AH., Flavonoids of Dracunculus vulgaris Schott leaves, Acta Pharm Turc 29:115-116, 1987.

  3. Reiter, B., Lechner, M. and Lorbeer, E., The fatty acid profiles-including petroselinic and cis-vaccenic acid-of different Umbelliferae seed oils, Fett/Lipid 100(11):498-502, 1998.

  4. Shibahara, A., Yamamoto, K., Nakayama, T. and Kajimoto, G. cis-Vaccenic acid [cis-octadec-11-enoic acid] in pulp lipids of commonly available fruits. JAOCS, J Am Oil Chem Soc 64(3):397-401, 1987.

  5. Schmid, PC., Holman, RT. and Soukup, VG., 13-Phenyltridecanoic acid in seed lipids of some Aroids, Phytochemistry 45(6):1173-1175, 1997.

  6. Saglik, S., Alpinar, K. and Imre, S., Fatty acid composition of the seed oil of Arum italicum Miller, J Food Lipids 9:95-103, 2002.

  7. Soukup, VG. and Holman, RT., Fatty acids of seeds of North American Pedicillate Trillium species, Phytochemistry 26(4):1015-1018, 1987.

  8. Badami, RC. and Patil, KB., Structure and occurence of unusual fatty acids in minor seed oils, Prog Lipid Res 19(3-4):119-153, 1981.

  9. Spitzer, V. Fatty acid composition of some seed oils of the Sapindaceae, Phytochemistry 42(5):1357-1360, 1996.

 

Corresponding Author: Serap Saglik, Istanbul University, Faculty of Pharmacy, Department of Analytical Chemistry, 34452 Beyazit, Istanbul, Turkey. serapsaglik@yahoo.com

 

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