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Essential Oil Composition of Hypericum L. Species from Southeastern Serbia and Their Chemotaxonomy

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Essential Oil Composition of Hypericum L. Species from Southeastern Serbia and Their Chemotaxonomy Biochemical Systematics and Ecology 35 (2007) 99e113 www.elsevier.com/locate/biochemsyseco Essential oil composition of Hypericum L. species from Southeastern Serbia and their chemotaxonomy Andrija Smelcerovic a, Michael Spiteller a,*, Axel Patrick Ligon a, Zaklina Smelcerovic a, Nils Raabe b a Institute of Environmental Research, University of Dortmund, Otto-Hahn-Str. 6, 44221 Dortmund, Germany b Department of Statistics, University of Dortmund, Vogelpothsweg 87, 44221 Dortmund, Germany Received 25 March 2005; accepted 16 September 2006 Abstract The essential oils of the aerial parts of nine species of Hypericum (Hypericum barbatum, Hypericum hirsutum, Hypericum li- narioides, Hypericum maculatum, Hypericum olympicum, Hypericum perforatum, Hypericum richeri, Hypericum rumeliacum and Hypericum tetrapterum), collected from different locations in Southeast Serbia, were obtained by steam distillation and ana- lyzed by GC and GCeMS. The essential oils investigated were characterized by a high content of non-terpene compounds and a low content of monoterpenes. The contents of non-terpenes, monoterpenes and sesquiterpenes in oils of the species H. barbatum, H. richeri and H. rumeliacum (section Drosocaprium) were similar and these oils were characterized by high contents of fatty acids. The oils of H. hirsutum and H. linarioides (section Taeniocarpium) contained a high percentage of n-nonane. There were similar- ities in contents of non-terpenes and sesquiterpenes in oils of species that belong to the section Hypericum (H. maculatum, H. per- foratum and H. tetrapterum). The oil of H. olympicum differed from others by higher terpene content. A comparison was also carried out of the chemical composition of the essential oils from flower, leaf and stem of H. perforatum and it revealed that the highest concentration of non-terpene compounds was found in the flower and stem oil, while a high concentration of sesqui- terpenes was characteristic for leaf oil. There were significant differences in the concentrations of the same compounds in the es- sential oils of H. maculatum, H. olympicum and H. perforatum, collected in different years from the same location which could be explained by seasonal differences. All data were statistically processed with principal component analysis and cluster analysis. The main conclusion from the above data is that genetic and environmental factors both play a role in determining the composition of essential oils of the Hypericum species studied. Ó 2006 Elsevier Ltd. All rights reserved. Keywords: Hypericum barbatum; Hypericum hirsutum; Hypericum linarioides; Hypericum maculatum; Hypericum olympicum; Hypericum perfo- ratum; Hypericum richeri; Hypericum rumeliacum; Hypericum tetrapterum; Essential oil composition * Corresponding author. Tel.: þ49 2317554080; fax: þ49 2317554085. E-mail address: [email protected] (M. Spiteller). 0305-1978/$ - see front matter Ó 2006 Elsevier Ltd. All rights reserved. doi:10.1016/j.bse.2006.09.012 100 A. Smelcerovic et al. / Biochemical Systematics and Ecology 35 (2007) 99e113 1. Introduction Hypericum L. is a genus of about 400 species, widespread in warm-temperature areas throughout the world and well represented in the Mediterranean area (Robson and Strid, 1986). Plants of the genus Hypericum have tradition- ally been used as medicinal plants in various parts of the world (Yazaki and Okada, 1994). Hypericum perforatum occupies a special position among the species of Hypericum. The chemical composition of H. perforatum oil has been the subject of many publications (Cakir et al., 1997; Baser et al., 2002; Osinska, 2002; Schwob et al., 2002a; Mockute et al., 2003; Smelcerovic et al., 2004). The content of the oil depends on the origin of the plant. Thus, a-pinene was the most abundant component of the oil of H. perforatum from Turkey (61.7 %) (Cakir et al., 1997) and b-caryophyllene of the oil from Uzbekistan (11.7%) (Baser et al., 2002). The two monoterpenes (a- and b-pinene) made up to 70% of the leaf essential oil of H. perforatum from India (Weyerstahl et al., 1995). The H. perforatum oils from Lithuania have been classified into three chemotypes: b-caryophyllene, caryophyllene oxide and germacrene D (Mockute et al., 2003). Considerable variation has already been reported in oil composition among different populations of H. perforatum from Serbia (Mimica-Dukic et al., 1997). The essential oil content of many other Hypericum species has been described: Hypericum androsaemum (Guedes et al., 2003), Hypericum brasiliense (Abreu et al., 2004), Hypericum coris (Schwob et al., 2002b), Hypericum dogonbadanicum (Sajjadi et al., 2001), Hypericum foliosum (Santos et al., 1999), Hypericum heterophyllum (Cakir et al., 2004), Hypericum hircinum (Bertoli et al., 2000), Hypericum hyssopifolium (Cakir et al., 2004), Hypericum lanceolatum (Vera et al., 1996), Hypericum linarioides (Cakir et al., 2005), Hypericum maculatum (Vasilieva et al., 2003), Hypericum perfo- liatum (Couladis et al., 2001), Hypericum richeri (Ferretti et al., 2005), Hypericum rumeliacum (Couladis et al., 2003), Hypericum scabrum (Cakir et al., 1997; Baser et al., 2002), Hypericum triquetrifolium (Bertoli et al., 2003). The flora of Serbia lists 19 species of Hypericum (Josifovic, 1972). Recently, the chemical composition has been determined of the essential oils of Hypericum atomarium (Gudzic et al., 2004), H. maculatum (Gudzic et al., 2002), Hypericum olympicum (Gudzic et al., 2001) and H. perforatum (Gudzic et al., 2001; Smelcerovic et al., 2004), all originating from Southeastern Serbia. The objective of this study was to determine the essential oil composition of nine wild-growing species of Hyper- icum (H. barbatum, H. hirsutum, H. linarioides, H. maculatum, H. olympicum, H. perforatum, H. richeri, H. rumelia- cum and Hypericum tetrapterum) from the Southeastern region of Serbia and to examine their potential chemotaxonomic significance. The chemical composition of oils obtained from flower, leaf and stem of H. perforatum and of the oils of H. maculatum, H. olympicum and H. perforatum collected in years 1998, 2001 and 2003 are also discussed. 2. Materials and methods 2.1. Plant material Table 1 contains information concerning the species of Hypericum studied, the voucher numbers of the specimens deposited in the herbarium (Herbarium Moesicum Doljevac, Serbia and Montenegro), the site and date of collection, together with their taxonomic placement within sections of the genus Hypericum (Robson, 1977). All the plant samples were collected at bloom stage. Dried and ground drug was steam distilled for 2.5 h using a Clevenger apparatus. 2.2. Identification procedure The oils were analyzed by analytical GC and GCeMS. Constituents were identified by comparison of their reten- tion times with standards and/or their mass spectra with those from the NIST MS library (Version 2.0a), Wiley MS library (Version 6) and the literature (Adams, 1989, 1995). The fatty acids and their methyl esters were identified by methylation of the essential oils. The solutions of essential oils in 2-propanol were derivatized with trimethylsul- fonium hydroxide to yield the methyl esters of the fatty acids (Vosman et al., 1998; Ishida et al., 1999). The coherence of the retention indexes of the analyzed compounds with the retention indexes obtained with a DB-5 column (Adams, 1989, 1995) constituted an additional criterion in the confirmation of each compound. A. Smelcerovic et al. / Biochemical Systematics and Ecology 35 (2007) 99e113 101 Table 1 Species of Hypericum from Southeast Serbia studied Sectiona Codeb Plant species Voucher number(HMDc) Collection period Locality Drosocarpium Spach. A2003 H. barbatum Jacq. 705 July 2003 Rtanj B2003 H. richeri Vill. 715 August 2003 Suva planina C2003 H. rumeliacum Boiss. 717 July 2003 Rujan planina Hypericum D2003 H. maculatum Crantz 711 July 2003 Stara planina D2001 H. maculatum Crantz. 701 June 2001 Vlasina D1998 H. maculatum Crantz. e July 1998 Vlasina EF2004 Flower of H. perforatum L. 728 June 2004 Pasina cesma EL2004 Leaf of H. perforatum L. 728 June 2004 Pasina cesma ES2004 Stem of H. perforatum L. 728 June 2004 Pasina cesma E2003 H. perforatum L. 714 July 2003 Rujan planina E2001 H. perforatum L. 703 June 2001 Rujan planina E1998 H. perforatum L. e July 1998 Rujan planina F2003 H. tetrapterum Fries. 722 August 2003 Beljanica Taeniocarpium Jaub. et Spach. G2003 H. hirsutum L. 708 August 2003 Suva planina H2003 H. linarioides Bosse. 709 August 2003 Suva planina Olympia (Spach.) Nyman I2003 H. olympicum L. 713 July 2003 Rujan planina I2001 H. olympicum L. 702 June 2001 Rujan planina I1998 H. olympicum L. e July 1998 Rujan planina a Taxonomic classification according to Robson (1977). b This is the code used for identifying samples studied in Tables 2e4. c Herbarium Moesicum Doljevac (Serbia and Montenegro). 2.2.1. Analytical GC A Thermo Finnigan Trace Gas Chromatograph, equipped with a fused silica capillary column (DB-5 30 m  0.25 mm  0.25 mm) and FID was used. The operating conditions were: temperature program, 60e320 C at 10 C/min and 320 C (4 min); injector temperature, 310 C; detector temperature, 320 C; carrier gas helium (1 mL/min); and split mode (1:25). 2.2.2. GCeMS Analyses were performed on a Thermo Finnigan Trace Gas Chromatograph and Trace MSPLUS detector, equipped with a fused silica column (DB-5 30 m  0.25 mm  0.25 mm); carrier gas helium (1 mL/min) with the same temper- ature program as for the analytical GC. Ionization was performed at 70 eV. Oil solutions were injected in two split modes (1:10 and 1:20). 2.3. Data analyses All data were statistically analyzed using statistical Software R (Foundation for Statistical Computing, Vienna, Austria, 2005, ISBN 3-900051-07-0). Analyses included principal component analysis and cluster analysis. 2.3.1. Principal component analysis A two-dimensional visualization of the position of the exemplars relative to each other was created by depicting the values of the first two principal components. The principal components are the axes of that orthogonal projection for which the values of the first axis have the highest possible variance, and those of the second have the second highest and so on (Hartung and Baerbel, 1999).
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