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Structure elucidation of cyclohexene (9Z)-octadec-9-enyl ethers isolated from the leaves of Uvaria cherrevensis (Annonaceae) |
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| Authors: | Chiramet Auranwiwat Alan T Maccarone Anthony W Carroll Roonglawan Rattanajak Sumalee Kamchonwongpaisan Stephen J Blanksby Stephen G Pyne Thunwadee Limtharakul |
| Institution: | 1. Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Chiang Mai University, Sutep, Muang, Chiang Mai, 50200, Thailand;2. The Graduate School, Chiang Mai University, Chiang Mai, 50200, Thailand;3. School of Chemistry and Molecular Bioscience, University of Wollongong, Wollongong, New South Wales, 2522, Australia;4. Mass Spectrometry User Resource and Research Facility, University of Wollongong, Wollongong, New South Wales, 2522, Australia;5. Medical Molecular Biology Research Unit, National Center for Genetic Engineering and Biotechnology, National Science and Technology Development Agency, Thailand Science Park, Pathumthani, 12120, Thailand;6. Central Analytical Research Facility, Institute for Future Environments, Queensland University of Technology, Brisbane, Queensland, 4001, Australia;7. Research Center on Chemistry for Development of Health Promoting Products from Northern Resources, Chiang Mai University, Chiang Mai, 50200, Thailand |
| Abstract: | The phytochemical investigation of the leaf extract of Uvaria cherrevensis (Annonaceae) yielded three new cyclohexene (9Z)-octadec-9-enyl ethers, cherrevenols M-O (1–3), and a known fatty ester derivative (4). The structures of the isolated compounds were elucidated by spectroscopic and computer-aided molecular modelling methods. Ozone Induced Dissociation (OzID) mass spectrometry was employed to determine the C-9 position of the side chain olefinic double bonds, while 13C NMR spectroscopy indicated their (Z)-configurations. All isolated compounds were evaluated for their antimalarial and cytotoxic activities; all were inactive. |
| Keywords: | Cyclohexenes Ozone Induced Dissociation (OzID) |
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