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

Author:
Auranwiwat, Chiramet, Maccarone, Alan T., Carroll, Anthony W., Rattanajak, Roonglawan, Kamchonwongpaisan, Sumalee, Blanksby, Stephen J., Pyne, Stephen G., Limtharakul, Thunwadee
Source:
Tetrahedron 2019 v.75 no.15 pp. 2336-2342
ISSN:
0040-4020
Subject:
Uvaria, antimalarials, carbon, chemical bonding, chemical constituents of plants, chemical reactions, chemical structure, cyclohexenes, cytotoxicity, ethers, leaf extracts, leaves, mass spectrometry, nuclear magnetic resonance spectroscopy, ozone, stable isotopes
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.
Agid:
6335338