Get 20M+ Full-Text Papers For Less Than $1.50/day. Start a 14-Day Trial for You or Your Team.

Learn More →

Isolation of eudesmane type sesquiterpene ketone from Prangos heyniae H.Duman & M.F.Watson essential oil and mosquitocidal activity of the essential oils

Isolation of eudesmane type sesquiterpene ketone from Prangos heyniae H.Duman & M.F.Watson... AbstractIn the present work, an endemic species Prangos heyniae collected in four locations from Turkey was subjected to hydrodistillation in Clevenger type apparatus to obtain the essential oils (EO1-4). The gas-chromatography/mass spectrometry (GC/MS) and gas-chromatography-flame ionization detector (GC/FID) analyses showed that the EOs were rich in sesquiterpenes, germacrene D (10.3-12.1%), β-bisabolene (14.4%), kessane (26.9%), germacrene B (8.2%), elemol (3.4-46.9%), β-bisabolenal (1.4-70.7%), β-bisabolenol (8.4%) and an eudesmane type sesquiterpene (1) (16.1%) with [M+218]. This unidentified compound (1) was isolated in a rapid one-step manner with >95.0% purity using Preparative Capillary Gas Chromatography (PCGC) with an HP Innowax column connected to a Preparative Fraction Collector (PFC) system. Structure determination was accomplished from 1D- and 2D-NMR spectroscopic data which determined a new eudesmane type sesquiterpene, 3,7(11)-eudesmadien-2-one (1). Using a biting deterrent bioassay, the mean proportion not biting (PNB) values of the P. heyniae EO1-4 were 0.88 for EO1 and 0.80 for EO2 which were similar to the positive control DEET (N,N-diethyl-3-methylbenzamide). The EO3 and EO4 had lower PNB values of 0.64 and 0.44, respectively. P. heyniae EO1-4 showed good larvicidal activity at 125 and 62.5 ppm whereas EO1-3 were slightly less effective at the dose of 31.25 ppm and EO4 was not active at 31.25 ppm against 1st instar Aedes aegypti. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Open Chemistry de Gruyter

Isolation of eudesmane type sesquiterpene ketone from Prangos heyniae H.Duman & M.F.Watson essential oil and mosquitocidal activity of the essential oils

Download PDF
15 pages

Loading next page...
 
/lp/degruyter/isolation-of-eudesmane-type-sesquiterpene-ketone-from-prangos-heyniae-MjBvyV737f
Publisher
de Gruyter
Copyright
© 2018 Gülmira Özek et al., published by De Gruyter
ISSN
2391-5420
eISSN
2391-5420
DOI
10.1515/chem-2018-0051
Publisher site
See Article on Publisher Site

Abstract

AbstractIn the present work, an endemic species Prangos heyniae collected in four locations from Turkey was subjected to hydrodistillation in Clevenger type apparatus to obtain the essential oils (EO1-4). The gas-chromatography/mass spectrometry (GC/MS) and gas-chromatography-flame ionization detector (GC/FID) analyses showed that the EOs were rich in sesquiterpenes, germacrene D (10.3-12.1%), β-bisabolene (14.4%), kessane (26.9%), germacrene B (8.2%), elemol (3.4-46.9%), β-bisabolenal (1.4-70.7%), β-bisabolenol (8.4%) and an eudesmane type sesquiterpene (1) (16.1%) with [M+218]. This unidentified compound (1) was isolated in a rapid one-step manner with >95.0% purity using Preparative Capillary Gas Chromatography (PCGC) with an HP Innowax column connected to a Preparative Fraction Collector (PFC) system. Structure determination was accomplished from 1D- and 2D-NMR spectroscopic data which determined a new eudesmane type sesquiterpene, 3,7(11)-eudesmadien-2-one (1). Using a biting deterrent bioassay, the mean proportion not biting (PNB) values of the P. heyniae EO1-4 were 0.88 for EO1 and 0.80 for EO2 which were similar to the positive control DEET (N,N-diethyl-3-methylbenzamide). The EO3 and EO4 had lower PNB values of 0.64 and 0.44, respectively. P. heyniae EO1-4 showed good larvicidal activity at 125 and 62.5 ppm whereas EO1-3 were slightly less effective at the dose of 31.25 ppm and EO4 was not active at 31.25 ppm against 1st instar Aedes aegypti.

Journal

Open Chemistry – de Gruyter

Published: May 23, 2018

References

  • Composition of the essential oil of Prangos heyniae H. Duman et M. F. Watson, a new endemic from Turkey
  • Isoarnottinin 4’-glucoside, a glycosylated coumarin from Prangos uloptera, with biological activity
  • An ethnobotanical survey of medicinal plants in western part of central Taurus Mountains: Aladaglar (Nigde–Turkey)
  • Comparative evaluation of cytotoxic and apoptogenic effects of several coumarins on human cancer cell lines: osthole induces apoptosis in p53-deficient H1299 cells
  • Biological activities of a Turkish medicinal plant, Prangos platychlaena
  • Aedes aegypti (Diptera: Culicidae) biting deterrence: structure-activity relationship of saturated and unsaturated fatty acids
  • Antioxidant properties of Prangos ferulacea (L.) Lindl., Chaerophyllum macropodum Boiss. and Heracleum persicum Desf. from Apiaceae family used as food in Eastern Anatolia and their inhibitory effects on glutathione-S-transferase
  • In vitro evaluation of the biological activity of Lebanese medicinal plants extracts against herpes simplex virus type 1