Yıldız et al. Nat. Volatiles & Essent. Oils, 2020; 7(1): 30-33 DOI: 10.37929/nveo.684540 RESEARCH ARTICLE Essential Oil Composition of Onosma isaurica Boiss. & Heldr. and Onosma bulbotrichum DC. from Tokat, Turkey Gülsüm Yıldız1, Yavuz Bülent Köse2, *, Mine Kürkçüoğlu3 Department of Pharmacognosy, Van Yüzüncü Yıl University, Faculty of Pharmacy, Van, 65080, TURKEY Department of Pharmaceutical Botany, Anadolu University, Faculty of Pharmacy, Eskişehir, 26470, TURKEY 3 Department of Pharmacognosy, Anadolu University, Faculty of Pharmacy, Eskişehir, 26470, TURKEY 1 2 *Corresponding author. Email: ybkose@anadolu.edu.tr Abstract The genus Onosma L. (Boraginaceae) is represented in Turkey by 105 species (110 taxa), 53 of them and 1 variety are endemic for Turkey. Some species of Onosma are used as herbs, traditional medicine such as against burns, wounds and ailments. Hydrodistilled essential oils of the aerial parts of Onosma isaurica Boiss. & Heldr. and Onosma bulbotrichum DC. were analyzed by GC and GC-MS systems, simultaneously. The essential oil of O. isaurica contained hexahydrofarnesyl acetone (20.3%), phytol (19.0%), farnesyl acetone (8.1%) and neophytadiene isomer I/tetradecanal (7.0%) as main constituents. The oil of O. bulbotrichum was characterized by the occurrence of hexahydrofarnesyl acetone (11.6%), farnesyl acetone (9.9%), hexadecanal (8.8%) E-geranyl acetone (7.4%) and neophytadiene isomer I (7.3%) as major components. Keywords: Onosma isaurica, Onosma bulbotrichum, volatile components Introduction The genus Onosma L. (Boraginaceae) is represented in Turkey by 105 species (110 taxa), 53 of them and one variety are endemic for Turkey (Riedl, 1978; Güner et al., 2012; Binzet, 2016). In traditional medicine, some species of Onosma are used as herbs, against burns, wounds and ailments (Khajuria and Jain, 1993; Özgen et al., 2003). Onosma species are known as ‘emzik otu’ in Turkey (Baytop, 1997). A literature survey has revealed that studies on the essential oil of Onosma species are limited. Roots of O. isaurica Boiss. & Heldr. were investigated in terms of in vivo anti-inflammatory and antinociceptive activities. (Tosun et al., 2008). In another recent study, tyrosinase inhibitory, antioxidant activities and total phenol contents were evaluated (Zengin et al., 2019). Aerial parts of O. isaurica are reportedly used against bronchitis as infusion (Melikoğlu et al., 2015). Hemmati et al. (2018) prepared a cream from the roots of O. bulbotrichum DC., which was used in the treatment of second degree burns. To the best of our knowledge, this is the first report on determination and comparison of the essential oils of O. isaurica Boiss. & Heldr. and O. bulbotrichum DC. by GC and GC/MS. Material and Methods Plant material O. isaurica and O. bulbotrichum were collected in June, 2017 in Tokat, Turkey. Voucher specimens are kept at the Herbarium of Faculty of Pharmacy of Anadolu University, Turkey (ESSE NO:15443, ESSE NO:15444, resp.). 30 Yıldız et al. Nat. Volatiles & Essent. Oils, 2020; 7(1): 30-33 DOI: 10.37929/nveo.684540 Isolation of essential oil Aerial parts of the plants were hydrodistilled for 3 h using a Clevenger-type apparatus. The essential oils were stored at 4°C in the dark until analysed. Oils yields of the samples were less than 0.1%. Analysis of the essential oils The oils were analysed by capillary GC-FID and GC/MS using an Agilent GC-MSD system, simultaneously. GC-MS conditions The oils were analysed by capillary GC/MS using an Agilent GC-MSD system (Agilent Technologies Inc., Santa Clara, CA). HP-Innowax FSC column (Hewlett-Packard-HP, U.S.A.) (60 m × 0.25 mm i.d., with 0.25 μm film thickness) was used for separation of components in the oil and helium as a carrier gas (0.8 mL/min). The GC oven temperature was kept at 60°C for 10 min and programmed to 220°C at a rate of 4°C/min, and kept constant at 220°C for 10 min and then programmed to 240°C at a rate of 1°C/min., at splitless mode. The injector temperature was set at 250°C. Mass spectra were taken at 70 eV with the mass range m/z 35-450. GC conditions The GC analysis were done with Agilent 6890N GC system fitted with a FID detector set at a temperature of 300°C. To obtain the same elution order with GC/MS, simultaneous auto-injection was done on a duplicate of the same column applying the same operational conditions. Relative percentage amounts (%) of the separated compounds were calculated from FID chromatograms. Identification of compounds Identification of essential oil components was performed by comparison of their mass spectra with those in the Baser Library of Essential Oil Constituents, Wiley GC/MS Library, Adams Library, MassFinder Library and confirmed by comparison of their retention indices (McLafferty and Stauffer, 1989; Adams, 2007; Hochmuth, 2008). A homologous series of n-alkanes were used as the reference points in calculation of relative retention indices (RRI) (Curvers et al., 1985). The relative percentages of the separated compounds were calculated from FID chromatograms. The analysis results are expressed as mean percentage as listed in Table 1. Results and Discussion Twenty-seven compounds constituting about 93.9 % of the essential oil of O. isaurica and twenty-six compounds constituting 87.2 % of the oil of O. bulbotrichum were characterized. The oil of O. isaurica comprised oxygenated monoterpenes, diterpenes and other hydrocarbons. It contained hexahydrofarnesyl acetone (20.3%), phytol (19.0%), farnesyl acetone (8.1%) and neophytadiene isomer I/tetradecanal (7.0%) as main constituents. The essential oil of O. bulbotrichum was characterized by the occurrence of hexahydrofarnesyl acetone (11.6%), farnesyl acetone (9.9%), hexadecanal (8.8%) E-geranyl acetone (7.4%) and neophytadiene isomer I (7.3%) as major components. In a previous study, main component of the essential oil of O. sieheana was found as p-cymene, while O. microcarpum was reported to contain thymol, carvacrol and n-heptane as major components (Morteza‐ Semnani et al., 2006; Binzet et al., 2019). Onosma echioides L. var. columnae Lacaita was characterized by the occurrence of hexadecanoic acid and phytol as major components in flower oils, while phytol and hexahydrofarnesyl acetone were the main components in the leaf oils (Maggi et al., 2009). To the best of our knowledge, this is the first report on the GC-FID and GC/MS determination of the essential oil compositions of O. isaurica and O. bulbotrichum. 31 Yıldız et al. Nat. Volatiles & Essent. Oils, 2020; 7(1): 30-33 DOI: 10.37929/nveo.684540 Table 1. Volatile components of O. isaurica (Oi) and O. bulbotrichum (Ob) RRI Compounds Oi Ob IM 1200 1300 Dodecane tr - MS Tridecane 1.0 - MS 1400 Tetradecane 0.9 - tR, MS 1400 Nonanal - 3.1 MS 1444 Dimethyl tetradecane 0.5 - MS 1500 Pentadecane 1.3 - tR 1506 Decanal - 4.0 MS 1594 trans--Bergamotene - 0.5 MS 1600 Hexadecane 0.6 0.4 MS 1621 Hexyl hexanoate 0.7 - MS 1655 (E)-2-Decenal - 0.5 MS 1655 1-Hexadecene 0.4 - MS 1661 Safranal 0.3 - MS 1700 Heptadecane 1722 Dodecanal 1765 1830 1868 (E)-Geranyl acetone 1882 1-Isobutyl-4-isopropyl-2,2-dimethyl succinate 1933 Neophytadiene isomer I 1933 Tetradecanal 1958 (E)--Ionone 1992 Neophytadiene 2041 Pentadecanal 2050 (E)-Nerolidol 2131 2135 - 0.6 tR, MS 2.2 5.7 tR, MS (E)-2-Undecenal - 1.0 MS Tridecanal - 2.1 MS 0.9 7.4 tR, MS - 0.6 MS 7.0 - MS 7.3 MS 3.6 MS 0.4 - MS - 1.6 MS - 1.0 tR, MS Hexahydrofarnesyl acetone 20.3 11.6 tR, MS Hexadecanal 5.0 8.8 MS 2179 3,4-Dimethyl-5-pentylidene-2 (5H)-furanone 0.8 1.1 tR, MS 2200 3,4-Dimethyl-5-pentyl-5H-furan-2-one 0.7 1.2 MS 2239 Carvacrol - 2.6 tR, MS 2300 Tricosane 2.1 3.2 tR, MS 2369 (2E, 6E)-Farnesol - 1.5 tR, MS 2384 Farnesyl acetone 8.1 9.9 MS 2400 Tetracosane 0.7 - tR, MS 2500 Pentacosane 6.2 2.0 MS 2551 Geranyl linalool 1.1 - tR 2622 Phytol 19.0 3.5 MS 2700 Heptacosane 6.1 2.4 MS 2900 Nonacosane 2.8 - MS 2939 1-Docosene 4.8 - MS Total 93.9 87.2 - RRI: Relative retention indices experimentally calculated against n-alkanes; % calculated from FID data; IM: Identification Method: tR: Identification based on comparison with co-injected with standards on a HP Innowax column; MS: identified on the basis of computer matching of the mass spectra. 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