Pharmaceutical Biology ISSN: 1388-0209 (Print) 1744-5116 (Online) Journal homepage: https://www.tandfonline.com/loi/iphb20 Micro-Distilled Volatile Compounds from Ferulago Species Growing in Western Turkey K. Hüsnü Can Baser, Betül Demirci, Temel Özek, Emine Akalin & Neriman Özhatay To cite this article: K. Hüsnü Can Baser, Betül Demirci, Temel Özek, Emine Akalin & Neriman Özhatay (2002) Micro-Distilled Volatile Compounds from Ferulago Species Growing in Western Turkey, Pharmaceutical Biology, 40:6, 466-471, DOI: 10.1076/phbi.40.6.466.8439 To link to this article: https://doi.org/10.1076/phbi.40.6.466.8439 Published online: 29 Sep 2008. Submit your article to this journal Article views: 178 View related articles Citing articles: 20 View citing articles Full Terms & Conditions of access and use can be found at https://www.tandfonline.com/action/journalInformation?journalCode=iphb20 Pharmaceutical Biology 2002, Vol. 40, No. 6, pp. 466–471 1388-0209/02/4006-466$16.00 © Swets & Zeitlinger Micro-Distilled Volatile Compounds from Ferulago Species Growing in Western Turkey* K. Hüsnü Can Başer1**, Betül Demirci1, Temel Özek1, Emine Akalın2 and Neriman Özhatay2 1 Medicinal and Aromatic Plant and Drug Research Centre (TBAM), Anadolu University, Eskişehir, Turkey; 2Faculty of Pharmacy, Department of Pharmaceutical Botany, Istanbul University Üniversite, Istanbul, Turkey Abstract Twelve Ferulago (Apiaceae) species growing in Turkey, viz. F. asparagifolia Boiss., F. aucheri Boiss., F. confusa Velen., F. galbanifera (Miller) W. Koch., F. humilis Boiss., F. idaea N. Özhatay et E. Akalın, F. macrosciadia Boiss. et Bal., F. mughlae Peşmen, F. sandrasica Peşmen et Quezel., F. silaifolia (Boiss.) Boiss., F. sylvatica (Besser) Reichb., and F. trachycarpa Boiss. were investigated for their chemical compositions by using a new technique: microdistillation. Milligram quantities of dried materials were sufficient for characterizing the composition of the volatiles using a GC/MS system. Keywords: Apiaceae, essential oils, Ferulago species, GC/MS, micro-distillation. Introduction The genus Ferulago W. Koch. (Apiaceae) is represented by 30 species; 16 of these are endemic in the flora of Turkey (Davis, 1972; Davis et al., 1988). The Ferulago species are known and used as “çakşırotu”, “kişniş”, “asaotu”, “kuzu başı” and “kuzu kemirdi” in different regions of Turkey (Akalın, 1999). Since ancient times, Ferulago species have been used in folk medicine as sedative, tonic, digestive, aphrodisiac and in the treatment of intestinal worms and haemorrhoids. (Akalın, 1999; Baytop, 1999). A number of the Ferulago species have previously been investigated for their chemical compositions. Monoterpenes and sesquiterpenes were reported from Ferulago nodosa, F. sylvatica and F. antiochia (Ruberto et al., 1999, 1994; Chalchat et al., 1992; Miski et al., 1990). The essential oils of F. trachycarpa and F. asparagifolia were previously investigated by our group (Başer et al., 1998, 2001). a- and b- Phellandrene were major constituents in the flower oil. pCymene and a-phellandrene were detected as major components in the stem oil of F. contracta from Iran (Rustaiyan et al., 1999). In a recent study, the hexane extracts and essential oil compositions of F. thyrsiflora, F. sylvatica, and F. nodosa have been investigated for their antimicrobial activities (Demetzos et al., 2000). Recently, we have reported the main components of the hydrodistilled essential oils of Ferulago asparagifolia, F. galbanifera, F. humilis and F. trachycarpa and the antimicrobial activity of their oils for the first time (Demirci et al., 2000). In our continuing research, we report on the essential oils obtained by micro-distillation from the fruits of 12 Ferulago species, using an Eppendorf MicroDistiller® system. The subsequent volatiles were analyzed and characterized by GC/MS. Materials and methods Plant material The plant materials and their collection sites are given in Table 1. Voucher specimens are kept at Herbarium of the Faculty of Pharmacy at Istanbul University in Istanbul (ISTE), Turkey. Distillation method The essential oils were obtained by micro-distillation from the fruits of 12 species of Ferulago by using an Eppendorf MicroDistiller®. * Presented at the 31th International Symposium on Essential Oils, 10–13 September 2000, Hamburg, Germany. Accepted: April 4, 2002 **Address correspondence to: Prof. Dr. K. Hüsnü Can Başer; Medicinal and Aromatic Plant and Drug Research Centre (TBAM), Anadolu University, 26470-Eskişehir, Turkey. Fax: +90 222 335 01 27; E-mail: khcbaser@anadolu.edu.tr or khcbaser@yahoo.co.uk Micro-distilled volatile compounds Table 1. Plant Materials used in this study. Code A B C D E F G H I J K L 467 Ferulago species Collection Site ISTE F. asparagifolia Boiss. F. aucheri* Boiss. F. confusa Velen. F. galbanifera (Miller) W. Koch F. humilis* Boiss. F. idaea* N. Özhatay et E. Akalın F. macrosciadia* Boiss. et Bal. F. mughlae* Peşmen F. sandrasica* Peşmen et Quezel. F. silaifolia* (Boiss.) Boiss. F. sylvatica (Besser) Reichb. F. trachycarpa Boiss. Aydın: Ephesus Muğla: Sandras Mountain Tekirdağ-Hayrabolu Bilecik Muğla: Sandras Mountain Balıkesir: Kazdağı Balıkesir: Kazdağı Muğla: Köyceǧiz Muğla: Sandras Mountain Bursa: Mezitler Çanakkale: Çan, Kazdağı Balıkesir: Edremit 76428 74565 72427 72560 74563 74485 72514 72535 74528 72530 72505 74661 * Endemic species. Micro-distillation Crushed fruits (~250 mg) were placed in a sample vial together with 10 ml of water. NaCl (2.5 g) and water (0.5 ml) were placed in the collecting vial. n-Hexane (300 ml) was added into the collecting vial to trap volatile components. Sample vials were heated to 100 °C at a rate of 20 °C/min and then kept at 100 °C for 15 min. Then, heated to 112 °C at a rate of 20 °C/min and kept at this temperature for 35 min. Finally, the samples were subjected to post-run for 2 min under the same conditions. Collecting vials were cooled to -5 °C during distillation. After the distillation was completed, the organic layer in the collection vial was injected to GC/MS. Analysis of essential oils The essential oils were analysed using a Hewlett-Packard G1800A GCD system. Innowax FSC column (60 m ¥ 0.25 mm Ø, with 0.25 mm film thickness). Helium (0.8 ml/ min) was used as carrier gas. GC oven temperature was kept at 60 °C for 10 min and programmed to 220 °C at a rate of 4 °C/min and then kept constant at 220 °C for 10 min to 240 °C at rate of 1 °C/min. Mass range was recorded from m/z 35 to 425. Injections were applied splitless. The injection port temperature was at 250 °C. The MS were recorded at 70 eV. The relative percentage amounts of the separated compounds were calculated automatically from peak areas of the total ion chromatogram. Alkanes were used as reference points in the calculation of relative retention indices (RRI). Library search was carried out using “Wiley GC/MS Library” and “TBAM Library of Essential Oil Constituents”. Results and discussion The volatiles were obtained from the fruits of the Ferulago species by micro-distillation for the first time. The results of their subsequent GC/MS analyses are given in Table 2. The main components were found as follows: Ferulago asparagifolia Boiss.: 42 components were characterized representing 94.8% of the total components detected. 2, 3, 6-Trimethylbenzaldehyde (42.0%) was the main component of the oil obtained by micro-distillation. We have previously investigated hydro-distilled essential oil of F. asparagifolia fruits collected from Antalya by GC/MS and we found that 2, 3, 6-trimethylbenzaldehyde (38.9%) and myrcene (18.2%) were the main components (Başer et al., 2001). Its oil was previously tested against bacteria and fungi (Demirci et al., 2000). Ferulago aucheri Boiss.: The composition of the essential oil of this endemic species has not been investigated previously. The isolation of flavonoids, coumarins and benzenoids were reported from the aerial parts of Ferulago aucheri (Doğanca et al., 1991, 1997). We have studied the essential oil composition of the 2 materials collected from 2 different regions in Turkey. Thirty-nine compounds, representing 81.6% of the oil, were identified with a-pinene (35.9%) as the main constituent. Ferulago confusa Velen.: Thirty-five components were characterized representing 99.4% of the oil. The main constituent was 2,5-dimethoxy-p-cymene (63.4%). As far as we know, this is the first report on the essential oil composition of F. confusa. Ferulago galbanifera (Miller) W. Koch: The main constituent of this oil was trans-chrysanthenyl acetate (17.2%). GC/MS analysis resulted in the characterization of 23 constituents representing 92.9% of the oil. F. galbanifera collected from Eskişehir showed a different essential oil profile with a-pinene (31.8%) and sabinene (15.8%) as main components. The oil of this species was previously evaluated for its antifungal and antibacterial activities (Demirci et al., 2000). Ferulago humilis Boiss.: This endemic species was previously investigated by our group. (Z)-b-Ocimene (32.4%) was reported as the main component and its oil was also tested 468 Table 2. K.H.C. Başer et al. The composition of the essential oils of Ferulago species. Compound RRI A B C D E F G H I J K L a-Pinene a-Thujene Isopropyl 2-methylbutyrate Camphene b-Pinene Sabinene d-2-Carene d-3-Carene Myrcene a-Phellandrene Isobutyl 2-methylbutyrate a-Terpinene Dehydro-1,8-cineole Limonene b-Phellandrene (Z)-b-Ocimene g-Terpinene (E)-b-Ocimene p-Cymene Isoterpinolene Terpinolene 1,2,4-Trimethyl benzene 1,2,3-Trimethyl benzene cis-Alloocimene a-Pinene oxide trans-Alloocimene Pentyl benzene g-Campholene aldehyde a,p-dimethylstyrene a-Cubebene trans-1,2-Limonene epoxide (Z)-b-Ocimene epoxide d-Elemene a-Ylangene Bicycloelemene a-Copaene a-Campholene aldehyde a-Bourbonene b-Bourbonene b-Cubebene Linalool trans-p-Menth-2-en-1-ol trans-Chrysanthenyl acetate Pinocarvone Aristolene a-Guaiene Bornyl acetate b-Elemene Terpinen-4-ol b-Caryophyllene Carvacrol methyl ether 6,9-Guaiadiene cis-p-Menth-2-en-1-ol trans-p-Mentha-2,8-dien-1-ol Myrtenal g-Elemene trans-Pinocarvyl acetate 1032 1035 1061 1076 1118 1132 1146 1159 1174 1176 1185 1188 1195 1203 1218 1246 1255 1266 1280 1286 1290 1294 1355 1382 1384 1409 1426 1439 1452 1466 1468 1476 1479 1493 1495 1497 1499 1528 1535 1549 1553 1571 1582 1586 1589 1596 1597 1600 1611 1612 1614 1617 1638 1639 1648 1650 1661 11.4 0.2 – – 0.5 6.2 – – – 4.3 0.4 0.4 – 1.1 1.4 – 1.2 – 2.7 – – 1.9 0.4 – – – – – 0.1 – – – – – – – 0.2 – – 0.1 0.1 – 5.2 – – – 0.3 – 1.6 – – – – – – – 1.0 35.9 – – – 1.5 0.2 – – tr – – – – 0.8 – – tr – 0.9 – – – – – 0.3 – – – – tr – – – – – – 4.3 0.3 1.4 – – – – 1.0 – 0.4 – – – 0.7 – – – – 1.1 – – 3.5 0.2 – tr 0.2 0.4 – tr 0.5 – – tr – 0.3 0.1 0.1 0.3 – 24.0 – 0.2 0.1 – – – – – – 0.1 – – – – – – – 0.1 – – – – – 1.2 – – – tr 0.1 0.2 – 0.9 – – – – – 0.1 – – – – 4.0 0.7 – – – 10.9 – – – 10.3 7.8 1.2 – – 11.9 – – – – – – – – 1.0 – – – – – – – – – – 1.0 – 0.6 – 17.2 – – – 5.0 0.9 – 7.8 – – – – – – 0.5 6.1 – 0.1 0.2 0.4 0.2 – – 2.3 – – – – 31.4 0.5 31.9 4.1 0.9 7.0 – 2.0 – – 1.1 – 0.1 – – 0.1 – 0.1 0.1 – – – 0.3 – – – – – – 4.0 – – – 0.6 0.5 – – 0.8 – – 0.1 0.1 – – 16.1 – – 0.4 0.7 – – 1.0 1.2 – – – – 1.5 – – 3.4 – 18.4 – – 2.2 0.6 – – – – – – – – – – – – – 1.4 – – – – – 8.8 – – – 1.4 – – – 13.4 – – – – – – 0.1 0.1 – – 25.4 0.1 – 1.7 1.3 0.7 0.5 tr 3.9 – – 0.2 0.1 3.1 6.1 0.3 0.2 tr 2.4 – 0.2 – – – – – – – 0.1 0.1 – – 1.6 0.3 – 1.6 – – 0.1 0.5 – 0.3 tr 0.1 0.3 – 0.1 0.9 – 1.0 tr 0.1 0.3 – 0.1 0.1 – 40.8 – – 1.1 1.5 0.2 – 0.1 0.6 – – – – 2.2 – – 0.1 – 0.5 – – – – – – – – 0.1 – – – – – – 0.1 – 1.1 – 0.5 0.1 – – 5.3 – – – 1.4 0.7 – 3.2 – – – – 0.4 – 0.1 5.6 – – – 0.4 0.1 – – 0.6 – – – – 0.3 – – – – 0.5 – 0.1 – – – – – – – – – – – 0.2 – – – 0.1 – – – – – 83.5 – – – 0.2 – – – – – – – – – 0.5 – – – – 0.1 0.4 – – 0.9 – – – – 1.0 0.1 1.2 2.8 – 45.8 – 1.4 – – – – – 2.8 – 0.3 – – 0.1 – – – – – – – – – – 0.1 – – – – – 0.2 – 0.5 – – – – – – – – – 0.7 tr 0.5 – 8.1 19.9 – – – – 5.1 1.8 1.5 27.8 – 21.6 0.4 1.2 – – – – – – – – 0.2 – – 0.2 – – – – 0.1 0.1 – 1.0 – 19.4 – – – – – – – – – – – – – – – – – – – – – – – – – – – – – 0.1 – 78.1 – – – – – – – – – 0.4 – – – – 0.4 – – – – – – – 3.1 – – – tr – – – – – – Micro-distilled volatile compounds Table 2. 469 (Continued) Compound RRI A B C D E F G H I J K L cis-Verbenol trans-Pinocarveol p-Mentha-1,5-dien-8-ol cis-p-Mentha-2,8-dien-1-ol trans-Verbenol a-Humulene g-Terpinyl acetate Myrtenyl acetate p-Mentha-1,8-dien-4-ol (=Limonen-4-ol) g-Muurolene a-Terpineol d-Selinene Borneol Verbenone Germacrene D a-Zingiberene Thujol b-Bisabolene b-Selinene a-Selinene Carvone Bicyclogermacrene cis-Piperitol cis-Chrysanthenol d-Cadinene g-Cadinene b-Sesquiphellandrene Kessane ar-Curcumene Selina-3(7),11-diene Myrtenol 3,7-Guaiadiene p-Mentha-1(7),5-dien-2-ol trans-Carveol Germacrene-B p-Cymen-8-ol 2,5-Dimethoxy-p-cymene epi-Cubebol Thymoquinone 2,3,4-Trimethylbenzaldehyde a-Calacorene 1,5-Epoxy-salvial-4(14)-ene g-Calacorene Caryophyllene oxide 2,3,6-Trimethylbenzaldehyde Salvial-4(14)-en-1-one Humulene epoxide-I (E)-Nerolidol Humulene epoxide-II Cubenol Humulene epoxide-III Elemol Guaiol Spathulenol T-Cadinol Thymol 1663 1664 1674 1678 1683 1687 1696 1698 0.5 – 0.3 – 1.3 – 0.2 0.3 0.1 3.4 0.5 – 6.4 3.4 – – – – – – 0.4 – – – – – – – – 0.7 – – – 0.4 0.1 0.1 1.1 0.1 – – – – – – 1.1 – – – – – – – – – – – – 0.3 0.1 – 0.7 1.8 – – – 1.4 0.5 – 1.4 5.8 – – 0.6 – – – 2.8 – – – – – – – – – – – – – – – – – – – 1700 1704 1706 1707 1719 1725 1726 1726 1729 1741 1742 1744 1751 1755 1758 1764 1773 1776 1783 1786 1786 1796 1804 1810 1823 1845 1854 1864 1878 1900 1908 1925 1941 1945 1984 2008 2019 2037 2045 2050 2071 2080 2081 2096 2103 2144 2187 2198 – – – – – – 0.2 – – – – – – 1.6 – – 0.4 – – 0.2 – – – – 0.1 0.2 0.4 0.1 – – 0.4 3.7 – – – – 42.0 – – – – – – – – 1.6 – – – 0.3 0.1 – – 0.8 1.0 – – – – 0.7 0.1 – – – 0.8 0.3 – – – – – – – – – 0.2 – – – – 0.4 1.9 0.1 2.6 – 0.7 0.7 0.4 7.3 – 0.6 – – – – – 0.1 – – – – – – – – – – – – – – – tr – – – – – – – – – – 0.5 63.4 – 0.1 0.2 – – – 0.1 1.7 – – – – – – – – – – tr – – – – – – 2.3 – – – – – – 1.8 – – – – – – – 0.8 – – – – 0.7 – – – – 2.2 – – – – – – – – – – – – – 2.6 – – 0.1 – – – – – 0.2 – – – – – 0.4 – – – 0.4 – – – – – – – – 0.2 – 0.1 0.1 – – – – – – – – – – – – – – – – 0.6 – – – – – – – – – – – – – – – – – – – – – – – – – – – tr – 0.5 13.2 – – – – – – – 14.1 – – – – – – – – – – – – – – – – – – – – – – – – – – – 0.1 – – – – – – – – – – 0.1 – – – – – – – – – – – – – – – – – – – 0.1 0.1 0.6 – 1.4 0.1 – 3.9 – 0.1 – 0.4 tr – 0.4 0.2 – 4.5 1.9 – – tr – 0.1 0.1 0.2 – 0.5 0.2 – 0.1 – – 0.5 0.1 0.3 0.4 0.4 0.1 – – 0.4 12.7 – 0.3 0.1 1.0 0.1 – – 0.1 0.2 – – – 8.1 – – – – 1.4 – 0.4 – – 0.3 0.2 – – – 0.4 0.4 – – 0.4 – 0.1 – – – – – 0.6 – 3.0 – 0.3 0.3 – 3.0 0.3 0.2 – – 1.3 – – – – – – – – – 0.3 – 0.2 – – – – – 0.6 – – 0.2 – 0.4 – – – – – – 0.1 – – – – – – – – 0.2 – – – – – – – – – – – 0.2 – – – – – – – – – – – – – – – – – – – – – – – – – – 1.0 40.2 – – – – – – – – – – – – – – – – – – – – – – – – – 1.4 – – – – – – 2.6 – – 1.5 – – – – – – – – – – – – – – – – – – – – – – – – – – – – 2.0 – – 470 Table 2. K.H.C. Başer et al. (Continued) Compound 1,6-Germacradien-5a-ol (=Germacrene D-4a-ol) T-Muurolol d-Cadinol Isocarvacrol (=4-isopropyl-2-methyl phenol) Methyl hexadecanoate Carvacrol trans-a-Bergamotol a-Cadinol 4-Isopropyl-6-methyl-1,2,3,4tetrahydronapthalen-1-one Monoterpenes Oxygenated Monoterpenes Sesquiterpenes Oxygenated Sesquiterpenes Others Total RRI A B C D E F G H I J K L 2202 2209 2219 – 0.1 – – – – – – – – – – – – – – – – – – – 0.5 0.1 0.2 – – – – – – – – – – – – 2221 2226 2239 2247 2255 – – 0.1 0.1 0.3 – – – – – 0.1 – 0.2 – – – 1.0 – – – – – – – – – – – – – – – 0.1 – – – – tr 0.1 0.4 – – – – 0.7 – – – – – – – 0.2 – – – – – – – 2419 – 29.4 57.6 2.7 2.3 2.8 – 39.3 17.5 11.0 13.8 – – 29.8 69.2 0.2 0.1 0.1 – 46.8 26.5 16.0 2.6 1.0 – 88.2 8.4 1.5 0.6 0.2 – 42.7 53.9 – – 2.8 – 21.2 78.5 0.1 – – 0.1 46.1 3.5 22.9 16.6 0.2 – 47.1 12.8 21.3 9.7 – – 7.6 88.6 1.3 – – – 53.7 45.6 – – – – 88.6 3.1 6.3 2.0 – 94.8 81.6 99.4 92.9 98.9 99.4 99.8 89.3 90.9 97.5 99.3 100 A: F. asparagifolia B: F. aucheri C: F. confusa D: F. galbanifera E: F. humilis F: F. idaea G: F. macrosciadia H: F. mughlae I: F. sandrasica J: F. silaifolia K: F. sylvatica L: F. trachycarpa RRI = Relative retention indices on a polar column tr = Trace (<0.1%) for its antifungal and antibacterial activities (Demirci et al., 2000). In the microdistilled oil, 38 components were identified representing 98.9% of the oil. The main component was (Z)-b-ocimene (31.9%). Ferulago idaea N. Özhatay et E. Akalın: This plant has recently been described as a new species (Akalın, 1999; Özhatay & Akalın, 2000). GC/MS analysis resulted in the characterization of 19 constituents representing 99.4% of the oil. The main component was p-cymene (18.4%). Ferulago macrosciadia Boiss. et Bal.: Fourteen compounds were identified representing 99.8% of the oil with carvacrol methyl ether (78.1%) as main constituent of this endemic species. Ferulago mughlae Peşmen: This endemic species has not been investigated previously. GC/MS analysis of the oil resulted in the characterization of 78 compounds representing 89.3% of the oil with a-pinene (25.4%) as the main component. Ferulago sandrasica Peşmen et Quezel.: a-Pinene (40.8%) was the main constituent in the essential oil of this endemic species. It was among the 44 characterized compounds representing 90.9% of the oil. Ferulago silaifolia (Boiss.) Boiss.: Twenty-one compounds representing 97.5% of the oil of this endemic species were identified with trans-chrysanthenyl acetate (83.5%) as the main constituent. Ferulago sylvatica (Besser) Reichb.: This species has been the subject of a previous study. Monoterpenes and sesquiterpenes were reported from aerial parts of the essen- tial oil of F. sylvatica (Chalchat et al., 1992). GC/MS analysis has resulted in the characterization of 19 compounds representing 99.3% of the oil with p-cymene (45.8%) as the main constituent. Ferulago trachycarpa Boiss.: Essential oil from fresh fruits of F. trachycarpa, collected from Karaman in Turkey, was previously investigated by our group. (Z)-bOcimene was reported as the main component (30.7%) (Başer et al., 1998). More recently, (Z)-b-ocimene (34.1%) was reported by us as the main of the essential oil from aerial parts of F. trachycarpa from Konya. Its antifungal and antibacterial activities were also reported (Demirci et al., 2000). In the scope of this work, we have studied the essential oil composition of the fruits collected from another region. GC/MS analysis resulted in the characterization of all 20 compounds of the oil with g-terpinene (27.8%) as the main component. In summary, the following compounds were identified in relative percentage amounts indicated in parantheses as major components, respectively: a-pinene: F. aucheri (36%), F. mughlae (25%), F. sandrasica (41%); 2,5-dimethoxy-pcymene: F. confusa (63%); 2, 3, 6-trimethylbenzaldehyde: F. asparagifolia (42%); p-cymene: F. sylvatica (46%), F. idaea (18%); carvacrol methyl ether: F. macrosciadia (78%); transchrysanthenyl acetate: F. silaifolia (84%), F. galbanifera (17%); g-terpinene: F. trachycarpa (28%); (Z)-b-ocimene: F. humilis (32%). The microdistillation technique enabled the isolation of volatiles of a few seeds/fruits in a rapid and efficient manner. Micro-distilled volatile compounds It gave quite comparable results with those of hydrodistilled oils (Briechle et al., 1997; Brunn et al., 1997). The method can particularly be useful in studying the essential oil composition of herbarium materials. 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