Essential oil composition of Hypericum L. species from Southeastern Serbia and their chemotaxonomy

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Abstract

The essential oils of the aerial parts of nine species of Hypericum (Hypericum barbatum, Hypericum hirsutum, Hypericum linarioides, 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 analyzed by GC and GC–MS. 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 similarities in contents of non-terpenes and sesquiterpenes in oils of species that belong to the section Hypericum (H. maculatum, H. perforatum 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 sesquiterpenes was characteristic for leaf oil. There were significant differences in the concentrations of the same compounds in the essential 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.

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 traditionally 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, α-pinene was the most abundant component of the oil of H. perforatum from Turkey (61.7 %) (Cakir et al., 1997) and β-caryophyllene of the oil from Uzbekistan (11.7%) (Baser et al., 2002). The two monoterpenes (α- and β-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: β-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 perfoliatum (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 Hypericum (H. barbatum, H. hirsutum, H. linarioides, H. maculatum, H. olympicum, H. perforatum, H. richeri, H. rumeliacum 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.

Section snippets

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.

Identification procedure

The oils were analyzed by analytical GC and

Essential oil composition of nine species of Hypericum

The compositions of the oils isolated from nine species of Hypericum are reproduced in Table 2. The oils were complex mixtures of non-terpenes, monoterpenes and sesquiterpenes: 98 components were identified in nine essential oils under study.

The non-terpene compounds made up the higher contribution (43.5%) in the essential oil of H. barbatum (Table 2, code A2003). The content of two fatty acids (hexadecanoic and octadecadienoic) amounted to 18.0%. The sesquiterpenes amounted to 28.3% with

Acknowledgements

We thank Prof. Dr. N. Randjelovic, Faculty of Occupation Safety Nis, Serbia, for taxonomic identification of the plant material and Prof. Dr. J. Jovanovic for critical reading of the manuscript. The Alexander von Humboldt Foundation, Bonn, Germany, supported the work through a fellowship to A. Smelcerovic.

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