Eyup BAGCI and Alpaslan KOCAK Firat University, Science & Letter Faculty, Biology Department, Elazig-Turkey

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1 International Journal of Science & Technology Volume 3, No 1, 13-18, 2008 Essential Oil Composition of the Aerial Parts of Two Salvia L. (S. multicaulis Vahl. Enum and S. tricochlada Bentham) Species from East Anatolian Region (Turkey) Eyup BAGCI and Alpaslan KOCAK Firat University, Science & Letter Faculty, Biology Department, Elazig-Turkey (Received: ; Accepted: ) Abstract The aerial parts of Salvia multicaulis Vahl. Enum. and S. tricochlada Bentham were hydro-distilled to produce the oils in the yields of 0.4% (v/w) and 0.3% (v/w), respectively. The oils were analysed by GC and GC/MS. Fifty-two and eighty-five components were identified representing 95.5% and 96.1% of the oils, respectively. The main compounds of S. multicaulis were 1,8-cineole (17.0%), camphor (13.2%), alpha-pinene (9.3%), valeranone(8.5%) and alpha-eudesmol (5.7%) whereas beta-pinene (13.7%), camphor (11.3%), caryophyllene oxide (7.0%), 1,8-cineole (5.9%) and trans-caryophyllene (5.5%) were the major constituents of S. tricochlada. Key Word: Salvia multicaulis, Salvia tricochlada, Essential oil, 1,8-cineole, alpha-pinene, camphor. Doğu Anadolu Bölgesinden (Türkiye) İki Salvia L. (S. multicaulis Vahl. Enum and S. tricochlada Bentham) Türünün Toprak Üstü Kısımlarının Uçucu Yağ Kompozisyonu Özet Salvia multicaulis Vahl. Enum. ve S. tricochlada Bentham nın toprak üstü kısımlarından su distilasyonu yöntemiyle yaklaşık olarak 0.4 ml ve 0.3 ml uçucu yağ elde edildi. Yağlar GC ve GC-MS cihazıyla analiz edildi. Yaklaşık olarak elli iki ve seksen beş bileşen yağın %95.5 ve %96.1 lik kısımını oluşturacak şekilde tanımlandı. S. multicaulis in ana bileşenleri; 1,8-sineol (%17), kamfor (%13.2), alfa-pinen (%9.3), valeranon (%8.5) ve alfaödesmol (%5.7) iken S. tricochlada nın ana bileşenleri; beta-pinen (%13.7), kamfor (%11.3), karyofillen oksit (%7) ve trans-karyofillen (%5.5) olarak tespit edildi. Anahtar Kelimeler: Salvia multicaulis, Salvia tricochlada, Uçucu yağ, 1,8-sineol, alfa-pinen, kamfor. 1.Introduction Salvia is the largest and the most important genus of the family Lamiaceae. It is includes nearly 900 species spread throughout the world. This genus is represented in Turkey by 89 species and altogether 94 taxa, 45 of which are endemic in Turkey [1-3]. Plants belonging to this genus show high diversity in their secondary metabolites [4] as well as in pharmacological effects. The species (S. multicaulis and S. tricochlada) studied were represented in G group in Flora of Turkey [1]. Many Salvia species and/or their essential oils are commonly used in the food, drug, cosmetic and perfumery industries. They are well known among people and widely used as flavourings or fragrance and for medicinal purposes in the several regions of the world [5-7]. S. syriaca is used as animal food [8,9]. Several species of Salvia are included in many pharmacopeias [10]. They are used for alimentary, pharmacological and cosmetic purposes [11-13]. Some of the components isolated from the extracts of S. multicaulis were diterpenoids [14] norditerpenoids [15] and triterpenoids [14] salvimultine [16], noricetexane diterpene. The essential oil of S. multicaulis from Iran has been also previously reported [17,18]. Bornyl acetate, β-caryophyllene and α-pinene were the major constituents of the flowering shoots [17], while the main constituents of the oil from leaves and flowers [18] were alpha-pinene (26.0%), 1.8 cineole + limonene (20.0%) and camphor

2 E.Bagci and A. Kocak (19.0%) were the predominant compounds in the oil of S. multicaulis [18]. This analysis result was revealed the composition of the S. multicaulis and S. tricochlada species from Eastern Anatolian region from Turkey. The aim of this study was to analyze and determine the aroma of two species Salvia genus (S. tricochlada and S. multicaulis) and to make a comparison of other genus patterns, growing in other habitats and climate and to do some contribution for food aroma industry. 2. Materials and methods 2.1. Plant Source Salvia multicaulis specimens were collected from natural habitats in Elazig Harput, Ankuzubaba mountain, at an altitude of 1200 m and S. tricochlada specimens were collected in Elazig Mürüdü hill at 1070 m. in 2005 Koçak and Voucher specimens are kept at the Fırat University Herbarium (FUH) Isolation of the essential oils Air-dried aerial parts of the plant materials were subjected to hydrodistillation using a Clevenger-type apparatus for 3 h to yield Gas Chromatographic (GC) and Gas Chromatography / Mass Spectrometry (GC- MS) Analysis The essential oil was analysed using HP 6890 GC equipped with and FID detector and also oils were analyzed by GC-MS, using a Hewlett Packard system. HP-Agilent 5973 N GC-MS system with 6890 GC in Plant Products and Biotechnology Res. Lab. (BUBAL) in Firat University. HP-5 MS column (30 m x 0.25 mm i.d., film tickness 0.25 µm) was used with Helium as the carrier gas. Injector temperature was C, split flow was 1 ml / min. The GC oven temperature was kept at 70 0 C for 2 min. and programmed to C at a rate of 10 0 C / min and then kept constant at 150 C for 15 min to C at a rate of 5 0 C / min. Alkanes were used as reference points in the calculation of relative retention indices (RRI). MS were taken at 70 ev and a mass range of Component identification was carried out using spectrometric electronic libraries (WILEY, NIST). The identified constituents of the essential oils are listed in Table I. 3. Results and discussion Fifty-two and eighty-five compounds were identified in S. multicaulis and S. tricochlada respectively, accounting from 95.5% to 96.1% of the whole essential oils. The yields of essential oils of S. multicaulis and S. tricochlada were 0.4% - 0.3%. The compositions of the essential oils are listed in table 1. Monoterpenes were the main class of essential oil of S. multicaulis and S. tricochlada (ca. 50% respectively). The high percentage of monoterpenes was largely due to the α-pinene, α-thujene, 1,8-cineole and camphor in S. multicaulis and camphene, β-pinene, 1,8-cineole and also camphor in S. tricochlada. Oxygenated derivatives were comprised a little of the essential oil composition. In the case of S. multicaulis, 52 compounds were identified representing 95.5% of the oil. 1,8-cineole was determined to be present at a high percentage (17.0%), camphor (13.2%), α-pinene (9.3%), valeranone (8.5%) and α-eudesmol (5.7%) made up 53.7% of the oil. The oil obtained from the aerial parts of S. multicaulis is reported to contain a high percentage of bornyl acetate [17]. Other species of genus Salvia, rich in thymol S. lanigera (54.9%) and S. spinosa (68.9%) and α-pinene in S. syriaca (12.6%) [9], S. tomentosa (33,7) [18], in S. multicaulis (26.0%) [18]. The percentage of the α-pinene was found as 9.3% in the S. multicaulis studied in here. The sample studied is different from the Iranian samples [19]. According to Ahmadi and Mirza [17], bornyl acetate(18.1%) and camphor (10.0%) were among the main components of S. multicaulis, whereas they also detected only in low amounts (0.4% and 0.5%, respectively) in the S. multicaulis Vahl. var. simplicifolia Boiss. [20]. In this study, while bornyl acetate was not found in S. multicaulis studied, camphor was detected at the similar percentages with the Iranian samples [17]. These differences might have been derived both from harvest time and local, climatic and seasonal factors or we can support the Senatore et al. [20], hypothesis that the Lebanese and Iranian samples belongs to a 14

3 Essential Oil Composition of the Aerial Parts of Two Salvia L. (S. multicaulis Vahl. Enum and S. tricochlada Bentham) Species from East Anatolian Region (Turkey) different chemotype and also Turkey and European patterns. However, further investigations are needed to elucidate this hypothesis. In the case of S. tricochlada, 85 components were identified representing 96.1% of the oil. β-pinene was the predominant compound (13.7%) followed by camphor (11.3%), caryophylleneoxide (7.0%) 1,8-cineole (5.9%) and trans-caryophyllene (5.5%). Beside thymol, other compounds are well known for their pleasant odour, such as cedrol (8.9%), methyl chavicol (3.5%), linalool (1.5%) and myrtenol (1.3%); these compounds are found as main components in the oils of some aromatic plants (Cedar wood, Basil, Coriander, Myrtle) which are used to prepare soft drink, food additives, cosmetics and for flavouring tobacco [12]. Some species of genus Salvia from Turkey were rich in germacrene D (27%), bicyclogermacrene (11.3%) and spathulenol (10.0%). in S. ceratophylla; α-copaene (21.1%), β-cubebene (8.1%), germacrene D (26.3%), bicyclogermacrene (24.1%) and δ-cadinene (5.0%) include S. aethiopis [21], β- caryophyllene (18.0%), germacrene D (16.5%), linalool L (9.2%), caryophyllene oxide (7.3%), linalyl acetate (6.0%), α-copaene (4.3%) and sclaraeol (6.6%) include S. palaestina; α-pinene (33.7%), germacrene D (7.5%), β-pinene (6.8%), α-humulene (6.0%), viridiflorol (3.8%) and limonene (3.1%) include S. tomentosa [18]. It is possible to say that, Salvia multicaulis showed 1,8-cineole/camphor type and S. tricochlada also comprised β- pinene/camphor type essential oils. Some of the Salvia species showed different type of essential oil, like α/β-pinene, like in S. blepharochlaena and S. caespitosa, α/β-thujone like in S. pilifera [7]. In conclusion, this study demonstrates the occurrence of 1,8-cineole chemotype of S. multicaulis and β-pinene chemotype of S. tricochlada in eastern Anatolian region of Turkey. However the absence of β-pinene and caryophylleneoxide in S. multicaulis chemotype is noteworthy. Table 1 Constituents of the essential oils from Salvia multicaulis and S. tricochlada No Compounds Name References RRI S. multicaulis S. tricochlada 1 2-hexenal b nonane trycyclene c α-thujene c α-pinene a,b,c α-tepinene camphene a sabinene a,c β-pinene a,c β-myrcene trans-sabinene hydrate phellandrene α-terpinolene benzene, 1-methyl d-limonene ,8-cineole a,b,c cis-ocimene cis-sabinene hydrate b ,3,6-octatriene γ-terpinene b,c α-campholene hydrate cyclopentasiloxane linalool b nonanal b cyclohexen-1-ol borneol a,b

4 E.Bagci and A. Kocak 27 camphor a,c cyclohexen-1-methanol pinocarvone b borneol L a,b cyclohexen-1-ol ethanone trans-carveol a,b myrtenol nerol decanal c piperitol isomer cyclohexen-1-one acetic acid bicyclo(2,2,1)heptan-2-ol phenol, 2-methyl myrtenol a cyclohexene (+)-cyclosativene α-copaene a,c β-bourbonene a,b,c β-elemene a zingiberene α-gurjunene b,c cis-jasmone c trans-caryophyllene β-cubebene c trans-α-bergamotene β-funebrene α-humulene a,b,c aromadendrene a,c α-longipinene α-amorphene germacrene D a,b,c α-farnesene tridecanone (+)-epi-bicyclosesquiphellanrene naphthalene c δ-cadinene b,c cis-calamenene β-sesquiphallandrene b α-cadinene α-calacorene butanamine bicyclogermacrene b nerolidol (+)-spathulenol b,c caryophylleneoxide b,c azulene thujopsene salvial-4(14)-en-1-one c veridoflorol a,b,c ledol a,c spiro(2,4)heptane isoaromadendrene epoxide isocaryophyllene c γ-cadinene a,c

5 Essential Oil Composition of the Aerial Parts of Two Salvia L. (S. multicaulis Vahl. Enum and S. tricochlada Bentham) Species from East Anatolian Region (Turkey) 83 β-eudesmol a,b,c dehydroaromadendrene β-selinene b valeranone α-bisabolol c vulgarol-b valerenol nerolidol benzyl bezoate aplopenone α-cadinol a,c vulgarol A α-eudesmol pentadecanone benzoic acid c δ-fenchene globulol c germacrene B c nonadecone phytol a,c hexadecanoic acid eicosane tetracosane pentacosane c octadecanone c Total RRI: Relative Retention Indices a: Identified in S. multicaulis var. simplificifolia [20] b: Identified in S. lanigera, [9] c: Identified in S. blepharochlaena [7]. References 1. Davis, P.H., (1982) Flora of Turkey and The East Aegean Island, Vol. 7, Edinburgh University Press. 2. Davis, P.H., Mill, R.R., Tan, K., (1988). Flora of Turkey and The East Aegean Island, Vol. 10, Edinburgh University Pres. 3. Güner, A., Özhatay, N., Ekim, T., Başer, K.H.C., (2000). Flora of Turkey and the East Aegean Islands, Vol. 11, Edinburgh University Pres. 4. Lu, Y.,& Yeap, F.L. (2002). Polyphenolics of Salvia a review. Phytochemistry, 59, Chalchat, JC., Michet, A., Pasquier B., (1998). Study of the clones of Salvia officinalis L. yields and chemical composition of essential oil. Flavour and Fragrence Journal, 13, Ozcan, M., Tzakou, O., & Couladis, M. (2003). Essential oil composition of Turkish herbal tea (Salvia aucheri Bentham var. canescens Boiss. et Heldr.) Flavour and Fragrance Journal, 18, Demirci, B., Baser, K. H. C., Yildiz, B., & Bahcecioglu, Z. (2003). Composition of essential oils of six endemic Salvia spp. from Turkey. Flavour and Fragrence Journal, 18, Ertug, F. (2000). An ethnobotanical study in central Anatolia (Turkey). Economic Botany, 54 (2), Flamini, G., Cioni, P. L., Morelli, I. & Bader, A. (2007). Essential oils of the aerial parts of three Salvia species from Jordan: Salvia lanigera, S. spinosa and S. syriaca. Food chemistry 100, Imbesi, A. (1964). Index plantarum quae in omnium populorum pharmacopies sunt adhuc receptae confecit Antonius Imbesi. Scilla, Italy: Messanae. 11. Ulubelen, A. (1964). Cardioactive and antibacterial terpenoids from some Salvia species. Phytochemisry, 64, Lawless, J. (2002). The encyclopedia of essential oils. London: Thorsons. 13. Perry, N., Bollen, C., Perry, E.K., & Ballard, C. (2003). Salvia for dementia therapy: review 17

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