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

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Article

Auranwiwat, Chiramet^1,2,3,4  Maccarone, Alan T.^4,5  Carroll, Anthony W.⁴  Rattanajak, Roonglawan⁶  Kamchonwongpaisan, Sumalee⁶  Blanksby, Stephen J.⁷  Pyne, Stephen G.⁴  Limtharakul, Thunwadee^1,2,8 

[1] Chiang Mai Univ, Fac Sci, Dept Chem, Chiang Mai 50200, Thailand

[2] Chiang Mai Univ, Fac Sci, Ctr Excellence Innovat Chem, Chiang Mai 50200, Thailand

[3] Chiang Mai Univ, Grad Sch, Chiang Mai 50200, Thailand

[4] Univ Wollongong, Sch Chem & Mol Biosci, Wollongong, NSW 2522, Australia

[5] Univ Wollongong, Mass Spectrometry User Resource & Res Facil, Wollongong, NSW 2522, Australia

[6] Natl Sci & Technol Dev Agcy, Med Mol Biol Res Unit, Natl Ctr Genet Engn & Biotechnol, Thailand Sci Pk, Pathum Thani 12120, Thailand

[7] Queensland Univ Technol, Inst Future Environm, Cent Analyt Res Facil, Brisbane, Qld 4001, Australia

[8] Chiang Mai Univ, Res Ctr Chem Dev Hlth Promoting Prod Northern Res, Chiang Mai 50200, Thailand

关键词: Uvaria cherrevensis;    Cyclohexenes;    Ozone Induced Dissociation (OzID);   

DOI  :  10.1016/j.tet.2019.03.004

来源: Elsevier

【 摘 要 】

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 C-13 NMR spectroscopy indicated their (Z)-configurations. All isolated compounds were evaluated for their antimalarial and cytotoxic activities; all were inactive. Crown Copyright (C) 2019 Published by Elsevier Ltd. All rights reserved.

【 授权许可】

Free