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Essential oil composition of Cymbocarpum erythraeum (DC.) Boiss. from Turkey a

b

c

Ayşe Betül Avci , Mustafa Korkmaz & Hasan Özçelik a

Medicinal and Aromatic Plants Department, Odemis Vocational School of Ege University, Izmir, Turkey b

Biology Department of Arts and Sciences, Faculty of Erzincan University, Erzincan, Turkey c

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Biology Department of Arts and Science, Faculty of Suleyman Demirel University, Isparta, Turkey Published online: 07 Mar 2014.

To cite this article: Ayşe Betül Avci, Mustafa Korkmaz & Hasan Özçelik (2014) Essential oil composition of Cymbocarpum erythraeum (DC.) Boiss. from Turkey, Natural Product Research: Formerly Natural Product Letters, 28:9, 636-640, DOI: 10.1080/14786419.2014.891116 To link to this article: http://dx.doi.org/10.1080/14786419.2014.891116

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Natural Product Research, 2014 Vol. 28, No. 9, 636–640, http://dx.doi.org/10.1080/14786419.2014.891116

Essential oil composition of Cymbocarpum erythraeum (DC.) Boiss. from Turkey ¨ zc elikc Ays¸e Betu¨l Avcia*, Mustafa Korkmazb and Hasan O

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a

Medicinal and Aromatic Plants Department, Odemis Vocational School of Ege University, Izmir, Turkey; Biology Department of Arts and Sciences, Faculty of Erzincan University, Erzincan, Turkey; c Biology Department of Arts and Science, Faculty of Suleyman Demirel University, Isparta, Turkey b

(Received 12 December 2013; final version received 1 February 2014) The aim of this study was to determine the essential oil content and composition of Cymbocarpum erythraeum (DC.) Boiss., a rare species spread in flora of Turkey. The samples were collected during the fructifying period of the plant from Erzincan, Turkey, at an altitude of 2430 m, in 2010. Essential oils were obtained from different parts of the plant such as fruits and herbal parts with Clevenger apparatus by hydrodistillation. Essential oil contents of the plant material were 0.38 ^ 0.015%, 0.23 ^ 0.012% and 0.21 ^ 0.015% from fruits, herbal parts with fruits and herbal parts without fruits, respectively. Composition of essential oil was identified by gas chromatography – mass spectrometry. The essential oil of the herbal parts of the plant was dominated by fatty alcohols and aldehydes which accounted for 73.10% and 24.64%, respectively. Myristyl alcohol (1-tetradecanol) was identified as a major component of essential oil with an average content of 73.10%. Keywords: Apiaceae; 1-tetradecanol (myristyl alcohol); East Anatolia

1. Introduction Essential oils are widely used in pharmaceuticals, cosmetics, perfume and fragrance industries and are obtained from plants especially grown in temperate and warm climate zones. Turkey is one of the most important countries located in the Mediterranean macroclimate zone allowing the country to have widely diverse regional and/or seasonal variations ranging from extremely harsh winter conditions to very hot and dry summers (Apak & Ulubay 2007). Thus Turkey has a rich diversity of medicinal and aromatic plants. The Parsley family, also called Apiaceae or Umbelliferae, is recognised with their economic importance and diversity of essential oils (Bas¸er et al. 2009). With characteristic flowers, fruits and a diverse chemistry, it is a well-known family for fragrance, flavour and even toxicity of many members (Kaya et al. 2003). It has 113 recorded cultivated species (except ornamentals) used as medicinal plants (42.5%), spice plants (19.5%) and essential oil plants (4.4%) (Khoshbakht et al. 2007). Despite the cultivated species, many others are still wildly growing in natural flora. Apiaceae is a large and economically important family of plants comprising between 300 to 462 genera and 2500 to 3750 species (Plunkett et al. 1996). The mentioned family is represented by 109 genera and 450 species in Turkey flora, and Asiatic Turkey has the highest intensity of species-level Apiaceae diversity in Asia. There are four endemic genera in Turkey (Pimenov & Leonov 2004) and 140 endemic species belonging to 42 genera are distributed in the country (Duran et al. 2010). Apiaceae is divided into three subfamilies, Hydrocotyloideae, Saniculoideae

*Corresponding author. Email: [email protected] q 2014 Taylor & Francis

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and Apioideae (Drude 1897). Of the three subfamilies, Apioideae is the largest (Tabanca et al. 2005) and most important economically (Downie et al. 2000) which includes Cymbocarpum (Ajani et al. 2008). There were four species in Cymbocarpum DC. (C. anethoides DC., C. erythraeum (DC.) Boiss., C. marginatum Boiss. and C. wiedemanni Boiss.), all of which are distributed in the Caucasus Turkey, and Iran (Boissier 1988 [1872]). Distributions of the species were given in some studies as B8: Erzurum: Palando¨ken, B9: Van: Tendu¨rek (Davis 1988), Erzincan: untidy (Kandemir & Tu¨rkmen 2008), and C. erythraeum has been recorded to be under ¨ ztu¨rk et al. 2004). Therefore, the species should be protected and cultivated. threat of extinction (O To the best of our knowledge, there is no previous publication on the composition of the essential oil of C. erythraeum. Here, we aimed to report on the essential oil content of different herb parts and essential oil composition of the species collected from Erzincan province. 2. Materials and methods 2.1. Plant material The vegetative parts of C. erythraeum (DC.) Boiss were collected during the fructifying period of the plant from Erzincan Kes¸is¸ Mountain, around Damlacık, Gedik locality (398440 475N, 398420 551E) of Turkey, at an altitude of 2430 m, in July 2010. Due to the narrow distribution of the species, 45 plants belonging to one population were studied. The plant specimens have been protected in the GUL Herbarium (Suleyman Demirel University, Isparta) with record number ¨ zc elik 13141). 63.66.4.14 (O 2.2. Essential oil isolation The essential oils were extracted by hydro-distillation for 3 h using a Clevenger-type apparatus (Ildam, Ankara,Turkey) from fruits and herbal parts (with and without fruit) of C. erythraeum (British Pharmacopoeia 1980). The plant material was kept in the dark at room temperature until essential oil isolation. The water residue was removed from the essential oils and the oils were stored in dark glass bottles at 48C until analysis. 2.3. Gas chromatography– mass spectrometry The essential oils were analysed by a gas chromatography –mass spectrometry (GC –MS) system in TUBITAK-MAM (Gebze-Kocaeli). The GC –MS analyses were performed using a Perkin Elmer GC –MS AutoSystem XL GC, MS were performed using Turbo Mass. Volatile compounds were separated on Thermo 5MS column (30 m £ 0.25 mm – 0.25mm) using helium gas as the carrier gas which was split 1 mL/min. Oven temperature was programmed from 508C for 2 min, ramp 5 to 2408C at 58C/min, then held at 2408C for 5 min. The temperature of injector and detector was 2008C and inlet temperature was 1758C. Mass spectra were taken at 70 eV, scan mode was full scan in the range m/z 35– 50 at 2008C ion temperature. The evaluation process was made using the library ‘Wiley, NIST and Tutor’. 2.4. Statistical analysis Mean percentage and standard deviation of essential oil values of the collected samples were calculated by MS Excel program. 3. Results and discussion 3.1. Essential oil contents and compositions The essential oils of C. erythraeum were obtained from different parts of the plant such as fruits, herbal part with fruits and herbal part without fruits by hydro-distillation. Averages of the

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contents were 0.38 ^ 0.015%, 0.23 ^ 0.012% and 0.21 ^ 0.015% from fruits, herbal part with fruits and herbal part without fruits, respectively. Each part of the plants had different contents of essential oil. The essential oil composition was analysed by GC – MS. Percentages of essential oil components of C. erythraeum are given to the herbal part with fruits of the species in Table 1. Eight components representing 99.96% of the total essential oil were identified. The essential oil was dominated by fatty alcohols and aldehydes accounting for 73.10% and 24.64%, respectively. The only one and major fatty alcohol of the oil was 1-tetradecanol (myristyl alcohol), 73.10%, while the aldehydes were (R)-(2 )-14-methylhexadec-8-enal, 11.98%, dodecanal, 6.81%, and decanal, 3.52%, in C. erythraeum essential oil as seen from Table 1. Other aldehydes were 2.6-nonadienal, 1.50%, in appreciable amounts and tetra decanal, 0.83%, in trace amounts. Alcanes and fatty acids were also present in the oil; 1.2-epoxy-1-vinyl cyclododecene (1.42%) and decanoic acid (0.80%), respectively. The essential oils obtained from different parts of C. erythraeum samples collected from Erzincan were investigated, and the oil-rich part of the plant was found to be the fruits. Many studies have been carried out on different species of the Apiaceae family and in many of them fruits have been used to obtain essential oils except stems, leaves or herbs. The essential oils obtained from the fruits of 11 species belonging to Apiaceae family showed a moderate antimicrobial effect (I˙s¸can et al. 2002). In another study, 15 species of Pimpinella (Apiaceae) were studied from the central Anatolia region and northern Black Sea region of Turkey, and essential oil yields ranged between 0.2 and 5.1% in fruits, 0.01 and 1.3% in stems and leaves and between 0.06 and 3.2% in roots (Tabanca et al. 2006). In this study, essential oil yields of C. erythraeum were determined as 0.38 ^ 0.015% in fruits, 0.23 ^ 0.012% in herbal parts with fruits and 0.21 ^ 0.015% in herbal parts without fruits. In the literature survey of the species, no study about the cultivation or essential oil contents and components could be found. There was a study on essential oil yields and components of C. wiedemannii Bios. from Turkey (Ankara: Polatli, Kargali village), and essential oil yields of fruits, 0.29%, and aerial parts, 0.62%, were determined (Baser et al. 1999). Eight components were identified in the essential oils of C. erythraeum, representing some chemicals as fatty alcohols, aldehydes, alkenes and fatty acids in this study. The main component of C. erythraeum essential oils was found to be 1-tetradecanol (myristyl alcohol) with average content of 73.10% as seen from Table 1. To the best of our knowledge, there is no previous publication on the composition of the essential oil of C. erythraeum, but in other Table 1. Essential oil constituents of C. erythraeum. Constituents Aldehydes Decanal Dodecanal Tetradecanal 2.6-Nonadienal (R)-(2 )-14-Methylhexadec-8-enal Sub-total Fatty alcohols 1-Tetradecanol Alcanes 1.2-Epoxy-1-vinyl cyclododecene Fatty acids Decanoic acid

RI

Area (%)

1209.7 1275.6 1412.8 1424.5 1471.3

3.52 6.81 0.83 1.50 11.98 24.64

1268.9

73.1

1676.2

1.42

1382.0

0.80

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species C. wiedemannii essential oil compositions were determined from fruits and aerial parts of the plant. Accordingly, (E)-2-decenal was found to be the major component representing 39.3 –31.7% content and also some other components such as fatty acid, decanoic acid 2 –8.7%, in fruits and aerial parts of the plants, respectively, were also determined. Other researchers who studied the Apiaceae family determined some aldehydes, alcohols, alcanes and fatty acids. Seseli tortuosum (Apiaceae) essential oil contained 3.2% esters and 3.0% aldehydes (Kaya et al. 2003). Under saline conditions, essential oils of Coriandrum sativum roots contained aldehydes and monoterpene alcohols, approximately 64.43 – 77.45% and 11.54 –11.81%, respectively (Neffati & Marzouk 2009). In another study on coriander leaves, aldehydes (55.5%), alcohols (36.3%) and alcanes (1.46%) were determined (Matasyoh et al. 2009). In fruits and leaves of Myrtus communis (Myrtaceae), essential oils contained non-terpenic alcohols, aldehydes, hydrocarbons, esters and some phenylpropanoid derivatives (Flamini et al. 2004). Flower heads, leaves and stem essential oils of Salvia anatolica (Lamiaceae) were classified into terpenes, fatty acids and their esters, and hydrocarbons and esters (Ozek et al. 2007). Essential oils are frequently used in the cosmetic industry either for the activity of the essential oil components or for its fragrance. Myristyl alcohol (1-tetradecanol) was determined as a major component of C. erythraeum essential oil and used as an emollient in cosmetics, and also serves as a basic component and solubility aid in metalworking fluids (Geier et al. 2006). Myrstyl alcohol is used as concealer and emollient in cosmetic preparations (Tırnaksız 2004). Thus, C. erythraeum oils can be used in natural cosmetics industry. 4. Conclusion In conclusion, essential oil contents and composition were determined for the first time in this study. Fruits are the economically useful part of the plant to obtain essential oil, and the essential oil contained a high amount of myrstyl alcohol (fatty alcohol) which can be used in the cosmetics industry. References Ajani Y, Ajani A, Cordes JM, Watson MF, Downie SR. 2008. Phylogenetic analysis of nrDNA ITS sequences reveals relationships within five groups of Iranian Apiaceae subfamily Apioideae. Taxon. 57:383–401. Apak G, Ubay B. 2007. First National Communication of Turkey on Climate Change. Ankara: The Ministry of Environment and Forestry; p. 383–401. Bas¸er KHC, Kurkcuoglu T, Askun T, Tumen G. 2009. Anti-tuberculosis activity of Daucus littoralis Sibth. et Sm. (Apiaceae) from Turkey. J Essent Oil Res. 21:572–575. ¨ zek T, Vural M. 1999. Essential oil of Cymbocarpum wiedemanni Boiss. J Essent Oil Res. 11:679–680. Baser KHC, O Boissier E. 1988 [1872]. Umbelliferae. In: Flora Orientalis. 2.H. Geneva: Georg. p. 892–1091. British pharmacopoeia. 1980. Vol II. London: H.M. Stationary Office. Davis PH. 1988. Flora of Turkey and East Aegean Islands. Vol. 10. Supplement. Edinburgh: Edinb. Un. Press; p. 151– 152. Downie SR, Katz-Downie DS, Watson MF. 2000. A phylogeny of the flowering Apiaceae based on chloroplast DNA rpl16 and rpoC1 intron sequences: towards a suprageneric classification of subfamily Apioidea. Am J Bot. 87:273–292. Drude O. 1897. Die naturlichen pflanzenfamilien. In: Engler A, Prantl K, editors. Umbelliferae. Vol. 3. Leipzig: Wilhelm Engelmann. p. 63 –250. ¨ ztu¨rk M, C ¨ . 2010. Taxonomic studies on the genus Rhabdosciadium Duran A, Dog˘an B, Duman H, Martin E, O ¸ etin O (Apiaceae) with particular reference to Turkish species and their relationships with some closely related genera. Biologia. 65:451–458. Flamini G, Cioni PL, Morelli I, Maccioni S, Baldini R. 2004. Phytochemical typologies in some populations of Myrtus communis L. on Caprione Promontory (East Liguria, Italy). Food Chem. 85:599–604. Geier J, Lessmann H, Fuchs T, Andersen KE. 2006. Patch testing with myristyl alcohol. Contact Dermatitis. 55:366–367. I˙s¸can G, Demirci F, Kırımer N, Ku¨rkc u¨og˘lu M, Bas¸er KHC, Kıvanc M. 2002. Bazi Umbelliferae Tu¨rlerinden Elde Edilen Uc ucu Yaglarin Antimikrobiyal Etkileri. In: Bas¸er KHC, Kırımer N, editors. 14. Bitkisel I˙lac Hammaddeleri Toplantısı. Eskis¸ehir: Bildiriler. p. 355–366.

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Essential oil composition of Cymbocarpum erythraeum (DC.) Boiss. from Turkey.

The aim of this study was to determine the essential oil content and composition of Cymbocarpum erythraeum (DC.) Boiss., a rare species spread in flor...
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