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Fatty acid composition of six Centaurea species growing in Konya, Turkey

Yener Tekelia; Mehmet Sezginb; Abdurrahman Aktumsekc; Gokalp Ozmen Gulerd; Murad Aydin Sandac a Department of Chemistry, Faculty of Science and Arts, Mustafa Kemal University, Hatay, Turkey b Department of Chemistry, Faculty of Science, Selcuk University, Konya, Turkey c Department of Biology, Faculty of Science, Selcuk University, Konya, Turkey d Department of Biological Education, Faculty of Ahmet Kelesoglu Education, Selcuk University, Konya, Turkey Online publication date: 24 November 2010

To cite this Article Tekeli, Yener , Sezgin, Mehmet , Aktumsek, Abdurrahman , Ozmen Guler, Gokalp and Aydin Sanda,

Murad(2010) 'Fatty acid composition of six Centaurea species growing in Konya, Turkey', Natural Product Research, 24: 20, 1883 1889 To link to this Article: DOI: 10.1080/14786411003754314 URL: http://dx.doi.org/10.1080/14786411003754314

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Natural Product Research Vol. 24, No. 20, 15 December 2010, 18831889

Fatty acid composition of six Centaurea species growing in Konya, Turkey

Yener Tekelia, Mehmet Sezginb, Abdurrahman Aktumsekc*, Gokalp Ozmen Gulerd and Murad Aydin Sandac
a Department of Chemistry, Faculty of Science and Arts, Mustafa Kemal University, Hatay, Turkey; bDepartment of Chemistry, Faculty of Science, Selcuk University, Konya, Turkey; c Department of Biology, Faculty of Science, Selcuk University, Konya, Turkey; dDepartment of Biological Education, Faculty of Ahmet Kelesoglu Education, Selcuk University, Konya, Turkey

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(Received 23 December 2009; final version received 15 February 2010) In this study, fatty acid compositions of six Centaurea species growing in the Konya region were determined. The fatty acid composition of Centaurea balsamita, Centaurea calolepis, Centaurea carduiformis subsp. carduiformis, Centaurea cariensis subsp. maculiceps, C. cariensis subsp. microlepis and Centaurea iberica were analysed. Four species of these six Centaurea are endemic to Turkey. The endemic Centaurea species are C. calolepis, C. carduiformis subsp. carduiformis, C. cariensis subsp. maculiceps and C. cariensis subsp. microlepis. Generally, C 18:2 o6 linoleic acid, C 16:0 palmitic acid, C 18:3 o3 linolenic acid and C 18:1 oleic acid were found to be the major fatty acids in all species. Polyunsaturated fatty acids (PUFAs) were found in higher amounts than saturated fatty acids and monounsaturated fatty acids in all species. PUFAs were determined at 55.10%, 50.25%, 51.41%, 41.02%, 46.18% and 58.80% in C. balsamita, C. calolepis, C. carduiformis subsp. carduiformis, C. cariensis subsp. maculiceps, C. cariensis subsp. microlepis and C. iberica, respectively. Keywords: Centaurea; fatty acid composition; Konya; Turkey

1. Introduction The genus Centaurea of the family Asteraceae is a large genus composed of about 500 species (Clapham, Tutin, & Warburg, 1952; GRIN Database, 2005). In Turkey, Centaurea is the third largest genus after Astragalus and Verbascum and is represented by 190 species, 117 of which are endemic (Uzunhisarcikli, Teksen, & Dogan, 2005). Most of the endemic Centaurea species have shown that Turkey is one of the gene centres of the genus. The genus is known as peygamber cicegi, zerdali dikeni, coban kald|ran and timur dikeni in Anatolia (Baytop, 1999; David, 1997; Wagenitz, 1975). Many species of the genus have been used in herbal medicine for their tonic, expectorant, antipyretic and antidiarrhoeal effects in Anatolian folk medicine (Baytop, 1999). Some Centaurea species, for example, Centaurea diffusa
*Corresponding author. Email: aktumsek@selcuk.edu.tr

ISSN 14786419 print/ISSN 10292349 online 2010 Taylor & Francis DOI: 10.1080/14786411003754314 http://www.informaworld.com

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and Centaurea maculosa, produce bioactive compounds (Inderjit, Callaway, & Vivanco, 2006). The genus has been subjected to several phytochemical studies, leading to the isolation of sesquiterpene lactones and flavonoids as the main secondary metabolites of its species (Akkal, Benayache, Medjroubi, Tillequin, & Seguin, 2003; Arif, Kupeli, & Ergun, 2004; Karamenderes, Bedir, Pawar, Baykan, & Khan, 2007; Koukoulitsa, Skaltsa, Karioti, Demetzos, & Dimas, 2002; Negrete et al., 1993; Yesilada, Gurbuz, Bedir, Tatli, & Khan, 2004). Fats and oils are organic compounds belonging to the group known as lipids, and are composed of glycerol and fatty acid molecules. The type and quantity of fatty acids in the lipid molecule and the position and distribution of these fatty acids within them determine their chemical, physical and functional properties. Recently, clinical and epidemiologic studies have shown that many chronic diseases are related to fatty acid type (WHO, 2003). Fatty acids are an important factor that contribute to the development of cardiovascular, cancer and degenerative diseases (Das, 2000; Grundy, 1997; Larsson, Kumlin, Ingelman-Sundberg, & Wolk, 2004; Slattery, Potter, Duncan, & Berry, 1997; Von Schacky, Angerer, Kothny, Theisen, & Mudra, 1999). Therefore, increased consumption of monounsaturated fatty acids (MUFAs) and polyunsaturated fatty acids (PUFAs) and decreased consumption of saturated fatty acids (SFAs) are linked to positive health outcomes (Lemaitre et al., 2006). Many species of Centaurea have been studied, especially for their volatile constituents. Some studies in the literature have referred to volatile compounds in Turkish endemic Centaurea species (Ertugrul et al., 2003; Flamini et al., 2002; Karamenderes, Demirci, & Baser, 2008; Kose, Demirci, Bas er, & Yucel, 2008), but no studies have yet been reported for the fatty acid composition of Centaurea species. Therefore, in this study, the fatty acid composition of Centaurea balsamita, Centaurea calolepis, Centaurea carduiformis subsp. carduiformis, Centaurea cariensis subsp. maculiceps, C. cariensis subsp. microlepis and Centaurea iberica have been analysed using gas chromatography (GC ).

2. Results and discussion The fatty acid compositions of six Centaurea species are presented in Table 1. As a result of the analysis, 20 fatty acids were identified as oils of the six Centaurea species. The major fatty acid identified in all Centaurea species was C 18:2 (linoleic acid), with the exception of C. cariensis subsp. microlepis. Similar results for Carthamus species (Sabzalian, Saeidi, & Mirlohi, 2008), Guizotia abyssinica (Ramadan & Morsel, 2003), Luffa cylindrica, Cucurbita pepo, Cucumis sativus, Canarium tramdenum, Hibiscus sabdariffa, Erythrophleum fordii, Amaranthus mangostanus, Solanum melangena, Chrysanthemum coronarium, Connarus paniculatus (Matthaus, Vosmann, Pham, & Aitzetmuller, 2003) and sunflower oil (Alpaslan & Gunduz, 2000) have been reported. Other predominant fatty acids of Centaurea species were C 16:0 (palmitic acid), C 18:3 o3 (linolenic acid), C 18:1 o9 (oleic acid) and C 18:0 (stearic acid), respectively. Smaller amounts of C 14:0 (miristic acid), C 12:0 (lauric acid) and C 16:1 o7 (palmitoleic acid) were detected. Linoleic acid content ranged from 23.92% to 40.60% for all Centaurea species. Also, linoleic acid was the major fatty acid in PUFAs. The fatty acid composition of

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Table 1. Fatty acid composition of six Centaurea species growing in Konya, Turkey.

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C. carduiformis C. cariensis C. cariensis subsp. subsp. subsp. maculiceps microlepis C. iberica Fatty acids C. balsamita C. calolepis carduiformis C 8:0 C 10:0 C 11:0 C 12:0 C 13:0 C 14:0 C 15:0 C 16:0 C 17:0 C 18:0 C 20:0 SFA C 14:1 !5 C 15:1 !6 C 16:1 !7 C 17:1 !8 C 18:1 !9 C 20:1 !9 MUFA C 18:2 !6 C 18:3 !6 C 18:3 !3 PUFA 0.05a 0.05 0.02 0.76 0.06 1.65 0.32 24.15 0.79 5.68 0.03 33.56 0.02 0.11 0.79 0.03 10.4 0.01 11.36 39.66 0.05 15.39 55.10 0.05 0.09 0.01 1.08 0.05 2.51 0.41 20.17 0.40 4.12 0.01 28.90 0.04 0.10 1.24 0.02 19.45 0.05 20.90 35.88 0.08 14.29 50.25 0.13 0.03 0.03 1.93 0.06 3.80 0.29 17.83 0.74 2.93 0.03 27.80 0.02 0.13 0.75 0.04 19.87 0.01 20.82 40.60 0.04 10.77 51.41 0.10 0.35 0.06 1.24 0.07 1.44 0.52 18.88 0.63 7.18 0.03 30.50 0.37 0.16 0.65 0.11 27.22 0.05 28.56 31.66 0.82 8.54 41.02 0.11 0.16 0.06 3.51 0.15 2.47 0.49 25.31 0.45 4.77 0.01 37.49 0.02 0.11 0.25 0.05 15.76 0.12 16.31 23.92 0.20 22.06 46.18 0.10 0.01 0.19 1.71 0.07 1.50 0.33 23.08 0.62 3.63 0.58 31.82 0.02 0.07 0.65 0.03 8.65 0.01 9.43 31.23 0.21 27.36 58.80

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Note: aAverage of three analyses.

oil seeds grown in Turkey has been investigated previously, and the linoleic acid content was determined between 3.3% and 70.1% (Ozgul-Yucel, 2005). The fatty acid composition of 17 seed oils has shown that linoleic acid was the major fatty acid except in one species (Rao & Sino, 1993). Linoleic acid was identified as the major fatty acid in Carthamus oxyacantha and Gundelia taurnefartii, which contained 76.06% and 60.15%, respectively (Heidari, Siami, & Monazami, 2000). Linoleic acid, one of the essential fatty acids, is very important for the nutritional value of oils (C. Eromosele & I. Eromosele, 2002). The high linoleic acid content makes the oil of Centaurea species nutritionally valuable. Palmitic acid was the major SFA and the amount of fatty acids in Centaurea species was found to be between 17.83% and 25.31%. In accordance with our results, in the fatty acid composition of Trifolium species, palmitic acid was shown to have the highest proportion in SFAs (Sabudak, Ozturk, Goren, Kolak, & Topcu, 2009). However, it has been determined that the palmitic acid in the seeds of five Nepeta species is lower than that found in our study, but palmitic acid is the major fatty acid identified in SFAs (Akpinar, Akpinar, Gorgun, Dirmenci, & Aktumsek, 2008). Linolenic acid was determined as the second highest fatty acid after linoleic acid in the PUFAs in our study. It has been found that the contents of linolenic acid varied from 8.54% to 27.36% in Centaurea species. Matthaus et al. (2003) have reported on the fatty acid composition of seeds from 40 plant species, and the oils

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contained linolenic acid in a range of 0.07% and 59.37%. Dagne and Jonsson (1997) have shown that the fatty acid composition in the seeds of Guizotia species contained linolenic acid between 0.20.5%, which was lower than in our study. Oleic acid was the highest composition of fatty acids found in MUFAs, ranging from 8.65% to 27.22% in the Centaurea species. In a recent study, it has been reported that oleic acid levels varied from 20.26% to 32.01% in different localities and varieties of Amaranthus cruentus (Berganza et al., 2003). Sabzalian et al. (2008) have reported that oleic acid is the major MUFA of the fatty acid composition in seeds of three safflower species. It has also been reported that PUFAs were higher than SFAs and MUFAs, as investigated in all Centaurea species. PUFAs were determined to be between 41.02% and 58.80% in Centaurea species. PUFAs content in C. iberica (58.80%) was higher than in the other Centaurea species. The level of SFAs and MUFAs were determined to be in the range of 27.8037.49% and 9.4328.56%, respectively. Similarly, Sabudak et al. (2009) have found that PUFAs are higher than SFAs and MUFAs in Trifolium species. Likewise, in the fatty acid composition of seed oils, the unsaturated fatty acid content is higher than that of the SFA content (Sabudak, 2007). In the fatty acid composition of cold-pressed seed flours, PUFAs content (0.617.3%) was lower than in our study. In that study, the contents of SFAs and MUFAs were 3.962.1% and 37.386.3%, respectively (Parry, Cheng, Moore, & Yu, 2008). According to these results, the oil of Centaurea species may be a good source of essential fatty acids. As PUFAs are accepted to be beneficial to health, the oils obtained in Centaurea species having high content of PUFAs could improve human health. Moreover, these oils may be assessed for use as edible oil.

3. Experimental 3.1. Plant materials The species C. balsamita, C. calolepis, C. carduiformis subsp. carduiformis, C. cariensis subsp. maculiceps, C. cariensis subsp. microlepis and C. iberica were collected from Konya. In this group, the species C. calolepis, C. carduiformis subsp. carduiformis, C. cariensis subsp. maculiceps and C. cariensis subsp. microlepis are endemic to Turkey. The plants were identified by one of the authors (M.A. Sanda) of Selcuk University. A voucher specimen has been deposited at the KON Herbarium, Department of Biology, Faculty of Science, Selcuk University.

3.2. Oil extraction The oil extraction of the dried and powdered aerial plants (10 g) of each Centaurea species was carried out at 60 C for 6 h by Soxhlet extractor, using petroleum ether as a solvent. The solvent was evaporated by a rotary evaporator.

3.3. Fatty acid methyl esters preparation The fatty acids in all the lipids were esterified into methyl esters by saponification with 0.5N methanolic NaOH and transesterified with 14% BF3 (v/v) in methanol (IUPAC, 1979).

Natural Product Research 3.4. GC conditions

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Fatty acid methyl esters (FAMEs) were analysed on a HP (Hewlett Packard) Agilent 6890N model GC, equipped with a flame ionisation detector (FID) and fitted to a HP-88 capillary column (100 m, 0.25 mm i.d. and 0.2 mm). The injector and detector temperatures were 240 C and 250 C, respectively. The oven was programmed at an initial temperature of 160 C and an initial time of 2 min. Thereafter, the temperature was increased up to 185 C at a rate of 4 C min1, then increased to 200 C at a rate of 1 C min1 and held at 200 C for 46.75 min. The total run time was 70 min. Helium (1 mL min1) was used as the carrier gas. Identification of the fatty acids was carried out by comparing sample FAME peak relative retention times with those obtained for Alltech and AccuStandards. The results were expressed as FID response area in relative percentages. Each reported result is given as the average value of three GC analyses. The results are presented as means.

Acknowledgements
The authors acknowledge the financial support provided by the Selcuk University Scientific Research Foundation (BAP) under Project FBE 06101048.

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