Terpenoids from a multiple shoot culture of Telekia speciosa

Abstract

IntroductionHeartleaf oxeye [Telekia speciosa (Schreb.) Baumg., Asteraceae, tribe Inuleae, basionym -Buphtalmum speciosum Schreb.] is a perennial plant native to Southeastern Europe and Asia Minor. It is the only species belonging to the genus Telekia Baumg. [1], which, accordingly to recent molecular phylogenetic studies based on both cpDNA and ITS sequence analysis [2] is closely related to Carpesium spp. and a group of resiniferous taxa of Inula L., including Inula helenium -a well known medicinal plant. Likewise the roots of the resiniferous Inula species, roots of T. speciosa contain essential oil with eudesmane-type sesquiterpene lactones as major constituents. Except for sesquiterpene lactones of eudesmanolide and pseudoguaianolide type, the plant reportedly contains xanthanolides, terpenoid cyclopropenone derivatives, polyacetylene, thymol and nerol derivatives [3][4][5][6]. Data on medicinal uses of T. speciosa are sparse, however, biological activity of secondary metabolites produced by the plant have gained some interest. Except for widely investigated alantolactone and isoalantolactone, other sesquiterpene lactones -telekin and 2,3-dihydroaromaticin have also shown marked antiproliferative activity against human cancer cell lines in vitro [7,8]. Moreover, 2,3-dihydroaromaticin is a potent inhibitor of lipopolisaccharide induced nitric oxide synthesis and a moderate inhibitor of the transcription factor NF-κB activation [9,10].Telekin affected activity of some antioxidant and drug-metabolizing enzymes in rat liver and kidney [11,12]. In a recently published report on antiproliferative and direct cytotoxic activity of extracts from T. speciosa an interference of these preparations with cell proliferation in vitro has been proven [13].The aim of the present study was to achieve in vitro multiplication of T. speciosa shoots and to investigate secondary metabolism of the culture as a potential source of biologically active compounds. Material and methods Plant materialSeeds of Telekia speciosa (Schreb.) Baumg. were delivered by Botanical Garden in Nantes (France). Multiple shoots of the plant were collected from in vitro cultures maintained in our laboratory. As a reference material, aerial parts of Telekia speciosa (Schreb.) were harvested in July-August from plants grown in the Garden of Medicinal Plants, Institute of Pharmacology, Polish Academy of Sciences, Kraków, where a voucher specimen (10/08) was deposited. The plants were obtained by acclimatization of in vitro regenerated plantlets and were collected in the second year of their vegetation outside. AbstractMultiple shoots of Telekia speciosa were cultivated on MS medium containing 4.44 µM BAP and 0.54 µM NAA, solidified with agar. After eight weeks of culture the shoots were harvested and extracted with methanol. From the methanol extract one pseudoguaianolide -2,3-dihydroaromaticin and three thymol derivatives: 8-hydroxy-9,10-diisobutyryloxythymol, 10-isobutyryloxy-8,9-epoxythymyl isobutyrate and 10-(2-methylbutyryloxy)-8,9-epoxythymyl isobuty...

Absolute Configuration of Menthene Derivatives by Vibrational Circular Dichroism

“…In addition, the seven characteristic proton chemical shifts for a β-D-glucopyranosyl moiety were observed (Table 1). Its 13 1). In the COSY spectrum of 1, H-3 (δ H 4.…”

“…The HRESI/APCIMS spectrum showed an [M + Na] + ion at m/z 623.2322 (calcd as 623.2310 for C 28 H 40 O 14 Na + ), in agreement with the molecular formula C 28 H 40 O 14 . The 1 H NMR data (Table 1) showed six methyl singlets within the δ H 2.12−2.01 range, and the 13 12 and Telekia speciosa; 13 however, the structure elucidation was based only on the 1 H NMR data in methanold 4 . 12 Herein, the 1 H NMR data were also recorded in DMSO-d 6 and pyridine-d 5 , while the 13 C and 2D NMR spectra were also measured in methanol-d 4 , DMSO-d 6 , and pyridine-d 5 (Tables 1 and 2).…”

“…The 1 H NMR data (Table 1) showed six methyl singlets within the δ H 2.12−2.01 range, and the 13 12 and Telekia speciosa; 13 however, the structure elucidation was based only on the 1 H NMR data in methanold 4 . 12 Herein, the 1 H NMR data were also recorded in DMSO-d 6 and pyridine-d 5 , while the 13 C and 2D NMR spectra were also measured in methanol-d 4 , DMSO-d 6 , and pyridine-d 5 (Tables 1 and 2). These spectra were useful to confirm the connectivity and the relative configuration of the molecule.…”

GC/MS analysis and antimicrobial activity of essential oils of Telekia speciosa (Schreb.) Baumg

“…It inhabits wet and shady positions in mountain woodlands (Chalchat et al, 2004;Domac, 1994), and somewhere it is planted as a decorative plant. It is closely related to genus Inula, including Inula helenium L., a well-known medicinal plant (Stojakowska et al, 2011). The underground parts of T. speciosa are traditionally used as a remedy for bronchial asthma in Balkan countries (Serbia, Bosnia and Herzegovina).…”

“…The underground parts of T. speciosa contain essential oil, bitter compounds and inulin (Marković et al, 2010). Phytochemical investigations have revealed T. speciosa as a rich source of sesquiterpene lactone -isoalantolactone, especially in its underground parts which amount is equivalent to I. helenium underground parts (Radulović et al, 2010;Stojakowska et al, 2011;2015a). The aerial parts extracts have been found to contain fatty acids, namely palmitic, linoleic, oleic, and caproic acids, and sterols (Deliorman et al, 2002;Orhan and Sener, 2003).…”