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

Ozek, Gulmira; Bedir, Erdal; Tabanca, Nurhayat; Ali, Abbas; Khan, Ikhlas A.; Duran, Ahmet; Baser, Kemal H. C.; Ozek, Temel


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{
  "DOI": "10.1515/chem-2018-0051", 
  "abstract": "In 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 (E01-4). 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%), beta-bisabolene (14.4%), kessane (26.9%), germacrene B (8.2%), elemol (3.4-46.9%), beta-bisabolenal (14-70.7%), beta-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 E01-4 were 0.88 for E01 and 0.80 for E02 which were similar to the positive control DEET (N, N-diethyl-3-methylbenzamide). The E03 and E04 had lower PNB values of 0.64 and 0.44, respectively. P. heyniae E01-4 showed good larvicidal activity at 125 and 62.5 ppm whereas E01-3 were slightly less effective at the dose of 31.25 ppm and E04 was not active at 31.25 ppm against 1st instar Aedes aegypti.", 
  "author": [
    {
      "family": "Ozek", 
      "given": " Gulmira"
    }, 
    {
      "family": "Bedir", 
      "given": " Erdal"
    }, 
    {
      "family": "Tabanca", 
      "given": " Nurhayat"
    }, 
    {
      "family": "Ali", 
      "given": " Abbas"
    }, 
    {
      "family": "Khan", 
      "given": " Ikhlas A."
    }, 
    {
      "family": "Duran", 
      "given": " Ahmet"
    }, 
    {
      "family": "Baser", 
      "given": " Kemal H. C."
    }, 
    {
      "family": "Ozek", 
      "given": " Temel"
    }
  ], 
  "container_title": "OPEN CHEMISTRY", 
  "id": "31247", 
  "issue": "1", 
  "issued": {
    "date-parts": [
      [
        2018, 
        1, 
        1
      ]
    ]
  }, 
  "page": "453-467", 
  "title": "Isolation of eudesmane type sesquiterpene ketone from Prangos heyniae H.Duman & MFWatson essential oil and mosquitocidal activity of the essential oils", 
  "type": "article-journal", 
  "volume": "16"
}
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