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ARS Home » Southeast Area » Miami, Florida » Subtropical Horticulture Research » Research » Publications at this Location » Publication #350260

Research Project: Methyl Bromide Replacement: Mitigation of the Invasive Pest Threat from the American Tropics and Subtropics

Location: Subtropical Horticulture Research

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

item OSEK, GULMIRA - Anadolu Universtiy
item BEDIR, ERDAL - Ege University
item Tabanca, Nurhayat
item ALI, ABBAS - University Of Mississippi
item KHAN, IKHLAS - University Of Mississippi
item DURAN, AHMET - Retired Non ARS Employee
item CAN BASER, H. HUSNU - Near East University
item OZEK, TERMEL - Anadolu Universtiy

Submitted to: Open Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 3/22/2018
Publication Date: 5/25/2018
Citation: Osek, G., Bedir, E., Tabanca, N., Ali, A., Khan, I.A., Duran, A., Can Baser, H., Ozek, T. 2018. Isolation of eudesmane type sesquiterpene ketone from Prangos heyniae H.Duman & M.F.Watson essential oil and mosquitocidal activity of the essential oils. Open Chemistry. 16:453-467.

Interpretive Summary: Prangos genus is an important genera in the parsley family, a family that also includes celery and carrots. Members of this genus have been used as an herb in cheese and the young shoots are consumed as a vegetable. Prangos heyniea is endemic in Turkey, and little information is available on the chemical composition. Therefore, scientists from SHRS in collaboration with scientists from Turkey and University of Mississippi conducted a detailed study on the chemical composition of P. heyniae essential oils collected from four different localities in Turkey. Oxygenated sesquiterpenes were the most dominant groups in three essential oils and one essential oil was rich in sesquiterpene hydrocarbons. A new eudesmane type sesquiterpene ketone was isolated using Preparative Capillary Gas Chromatography (PCGC) system. Within the same plant species, chemotypes are very common, therefore, more research is need to better understand the chemical profile of P. heyniae. In this study, we found that the PCGC system was a useful technique for separation of individual compounds from complex mixtures such as P. heyniae essential oils. The new sesquiterpene identified in this research may provide a new source of repellent or toxicant material for researchers that are investigating new tools for insect pest management and control.

Technical Abstract: In the present work, an endemic species Prangos heyniae H.Duman & M.F.Watson collected four different locations from Turkey were subjected to hydrodistillation in a Clevenger type apparatus to obtain the essential oils (EO1-4). The GC/MS and GC-FID analyses showed that the EOs were rich in sesquiterpenes, germacrene D (10.3-12.1%), '-bisabolene (14.4%), kessane (26.9%), germacrene B (8.2%), elemol (3.4-46.9%), '-bisabolenal (1.4-70.7%), '-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 resulted with new eudesmane type sesquiterpene, 3,7(11)-eudesmadien-2-one (1). In biting deterrent bioassay, mean proportion not biting (PNB) values of the P. heyniae EO1-4 were 0.88 for EO1 and 0.8 for EO2 that were similar to positive control DEET (N, N-diethyl-3-methylbenzamide). The EO3 and EO4 had lower PNB values of 0.64 and 0.44, respectively. Prangos 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 Ae. aegypti.