Fatty acids and their esters from Cicuta virosa L

n -Hexane and chloroform fractions of aerial parts and roots of Cicuta virosa L. were investigated by GC-MS. As a result of the study 25 fatty acids and their esters have been identified. Two unsaturated esters such as linoleic acid ethyl ester ( IX , 16.66%), and n - hexadecanoic acid ethyl ester ( VII , 10.12%), the fatty acid n -hexadecanioc acid ( VI , 8.10%) made up the bulk of the aerial parts. Four unsaturated esters such as linoleic acid ethyl ester ( IX , 10.15%), dibutylphthalate ( XII , 9.55%), n -hexadecanoic acid ethyl ester ( VII , 8.19%) and 9, 12, 15 - octadecatrienoic acid ethyl ester ( X , 5.9%), two fatty acids as n -hexadecanoic acid ( VI , 8,15%) and 9,12-octadecadienoic acid ( VIII , 4,5%) predominated in the roots of Cicuta virosa L. These known fatty acids and their esters were found for the first time in this plant species. DOI: http://dx.doi.org/10.5564/mjc.v14i0.203 Mongolian Journal of Chemistry 14 (40), 2013, p71-74


INTRODUCTION
Cicuta virosa L. or water hemlock is a member of the genus Cicuta, of the Umbelliferae family plants.Six species, native to temperate regions of North America and Asia, are belonged to the genus Cicuta [1].Only one species Cicuta virosa L is widespread and found in Khentei, Khangai, Mongol Daurian, Mongol Altai, Dornot Mongol, Gobi Altai (Bayan-Tuhum-Nuur) and Transaltai Gobi (Ih tsaram) regions of Mongolia [2].Previously some pharmacological activities such as insecticidal, antioxidative activity and antileukemic properties of Cicuta virosa have been investigated [3][4][5].In our previous phytochemical study of Cicuta virosa L. growing in Mongolia resulted with identification of seven known alkaloids and eleven alcohols [6,7].The aim of the present study is to identify the fatty acids and esters in aerial parts and roots of Cicuta virosa L. subjecting the n-hexane and chloroform fractions by the Gas chromatography-Mass spectral analysis.

EXPERIMENTAL
Gas Chromatography-Mass spectrometry (GC-MS), well equipped with fused silica capillary column 30 m X 0.25 mm X 0.25 μm was used.Coated with HP-5 MS phase and coupled with Hewlett Packard 6890/MSD 5793 A E was used.He with 0.8 ml/min flow rate was used a carrying gas.Program of the GC-MS as follows: temperature 50-300 o C at 6 o /min, isotherm 0-10 min, solvent delay 2.0 min, mass range 50-750.The flame ionization detector was used at T inl 260 o C, T aux 280 o C. Plant material: Aerial parts of Cicuta virosa L. collected (275g) in July, while roots in April (280g), in July (350g) and in October (382g) at Achuutiin gol of Bulgan aimag, Central Mongolia.The plant material was identified by Prof. Ch.Sanchir, Institute of Botany Mongolian Academy of Sciences (MAS), and the voucher specimen is deposited in the Herbarium Fund of the same Institute.

Extraction and isolation:
The air-dried and powdered aerial parts (275 g) and roots (280, 350 and 382 g) of Cicuta virosa L. were extracted with EtOH (each drug 4 x 3000 ml) at room temperature.The combined ethanol extracts were evaporated to dryness in vacuo.The resultant each crude extract was dissolved in distilled H 2 O (400 ml) and partitioned between nhexane, CHCI 3 , ethylacetate and n-BuOH, respectively.The n-hexane and CHCI 3 fractions were concentrated in vacuo and gave 26.6 g of dry n-hexane fraction and 33.9, 40.0, 37.0 g of dry CHCI 3 fractions, respectively.These fractions were subjected to preliminary phytochemical tests.

Gas-Chromatography -Mass Spectrometry analysis:
Two μl of n-hexane and chloroform fractions of aerial parts and roots from Cicuta virosa L. were employed for GC-MS analysis.The molecular weight and structure of compounds of test materials were ascertained by interpretation on mass spectrum of GC -MS using the database of National Institute Standards and Technology (NIST).

RESULTS AND DISCUSSION
The fatty acids and esters composition of aerial parts of Cicuta virosa L. isolated from the n-hexane and chloroform fractions were summarized in table 1.
As a result of GC-MS analysis of the n-hexane fraction of Cicuta virosa 13 known compounds have been identified, as 4 fatty acids and 9 their esters.Of these substances linoleic acid ethyl ester (IX, 16.66%), hexadecanoic acid ethyl ester (VII, 8.12%) and n-hexa-decanioc acid (VI, 8.10%) have detected as a major one.The fatty acids and their esters compositions of chloroform fractions from roots Cicuta virosa L are summarized in Table 2   Unsaturated fatty acids and esters are crucial to every cell in the body for normal growth.Especially, they provide lubricating quality for blood vessels and nerves to keep skin and other tissues young [8].
Plants and other natural products with medicinal properties can be a source of antioxidant, antiinflammatory, anti-cancer agents to continue to be relevant in the research areas and leads to the development of traditional drugs.

CONCLUSIONS
In the present study 25 fatty acids and esters have been identified from the n-hexane and chloroform fractions from aerial parts and roots of Cicuta virosa L. by GC-MS analysis.Two unsaturated esters such as linoleic acid ethyl ester (IX, 16.66%) and nhexadecanoic acid ethyl esters (VII, 10.12%), one fatty acid n-hexadecanioc acid (VI, 8.10 are constituted the bulk of the aerial parts, while four unsaturated esters such as linoleic acid ethyl ester (IX, 10.15%), dibutylphthalate (XII, 9.55 n-hexadecanoic acid ethyl ester (VII, 8.19%) and 9,12,15-octadecatrienoic acid ethyl ester (X, 5.9%), two fatty acids nhexadecanoic acid (VI, 8.15% ) and 9,12octadecadienoic acid (VIII, 4.5%) were dominated in the roots of Cicuta virosa L. These known fatty acids and their esters have been found for the first time in this species.

Table 1 .
. Fatty acids and esters of aerial parts of Cicuta virosa L.

Table 2 .
Fatty acids and their esters of the chloroform fraction from roots of Cicuta virosa L.As a result of GC-MS investigation 22 compounds have been identified including 4 esters and 3 fatty acids, 14 esters and 3 fatty acids, 5 esters and 2 fatty acids in the roots Cicuta virosa L. collected in April, July and October respectively.Analysis resulted that in the root harvested in April linoleic acid ethyl ester N Name of compounds and molecular formulaСontent in the roots, % Retention time, min.(4.77%), 9,12,15-octadecatrienoic acid ethyl ester (5.90%) and dibutyl phthalate (9.55%) have dominated.Whereas, in the roots collected in July nhexadecanoic acid (8.15%), n-hexadecanoic acid ethyl ester (8.19%), linoleic acid ethyl ester (10.15%) have dominated.Finally, in the roots harvested in October linoleic acid ethyl ester (4.18%) has dominated too.Thus lenoleic acid ethyl ester IX prevails in roots collected all vegetation periods.

Table 3 .
Therapeutic activity of some fatty acids and their esters identified from the n-hexane and chloroform fractions of aerial parts and roots of Cicuta virosa L.