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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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    "creators": [
      {
        "affiliation": "Anadolu Univ, Fac Pharm, Dept Pharmacognosy, TR-26470 Eskisehir, Turkey", 
        "name": "Ozek, Gulmira"
      }, 
      {
        "affiliation": "Izmir Inst Technol, Dept Bioengn, TR-35430 Izmir, Turkey", 
        "name": "Bedir, Erdal"
      }, 
      {
        "name": "Tabanca, Nurhayat"
      }, 
      {
        "affiliation": "Univ Mississippi, Natl Ctr Nat Prod Res, University, MS 38677 USA", 
        "name": "Ali, Abbas"
      }, 
      {
        "affiliation": "Univ Mississippi, Natl Ctr Nat Prod Res, University, MS 38677 USA", 
        "name": "Khan, Ikhlas A."
      }, 
      {
        "affiliation": "Veysel Karani St,Blok K-38, Selcuklu Konya, Turkey", 
        "name": "Duran, Ahmet"
      }, 
      {
        "affiliation": "Near East Univ, Fac Pharm, Dept Pharmacognosy, Mersin 10, Lefkosa Nicosia Trnc, Turkey", 
        "name": "Baser, Kemal H. C."
      }, 
      {
        "name": "Ozek, Temel"
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    "description": "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.", 
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      "issue": "1", 
      "pages": "453-467", 
      "title": "OPEN CHEMISTRY", 
      "volume": "16"
    }, 
    "license": {
      "id": "cc-by"
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    "publication_date": "2018-01-01", 
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    "title": "Isolation of eudesmane type sesquiterpene ketone from Prangos heyniae H.Duman & MFWatson essential oil and mosquitocidal activity of the essential oils"
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