Structure elucidation of cyclohexene (9Z)-octadec-9-enyl ethers isolated from the leaves of Uvaria cherrevensis (Annonaceae)

Authors

Chiramet Auranwiwat, University of Wollongong, Chiang Mai University
Alan T. Maccarone, University of WollongongFollow
Anthony Carroll, University of WollongongFollow
Roonglawan Rattanajak, Thailand Science Park
Sumalee Kamchonwongpaisan, Thailand Science Park
Stephen J. Blanksby, Queensland University of TechnologyFollow
Stephen G. Pyne, University of WollongongFollow
Thunwadee Limtharakul, Chiang Mai University

RIS ID

134049

Publication Details

Auranwiwat, C., Maccarone, A. T., Carroll, A. W., Rattanajak, R., Kamchonwongpaisan, S., Blanksby, S. J., Pyne, S. G. & Limtharakul, T. (2019). Structure elucidation of cyclohexene (9Z)-octadec-9-enyl ethers isolated from the leaves of Uvaria cherrevensis (Annonaceae). Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry, 75 (15), 2336-2342.

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 13 C NMR spectroscopy indicated their (Z)-configurations. All isolated compounds were evaluated for their antimalarial and cytotoxic activities; all were inactive.