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

Journal Article


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.

UOW Authors


  •   Auranwiwat, Chiramet (external author)
  •   Maccarone, Alan (external author)
  •   Carroll, Anthony (external author)
  •   Rattanajak, Roonglawan (external author)
  •   Kamchonwongpaisan, Sumalee (external author)
  •   Blanksby, Stephen J. (external author)
  •   Pyne, Stephen
  •   Limtharakul, Thunwadee (external author)

Publication Date


  • 2019

Citation


  • 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.

Scopus Eid


  • 2-s2.0-85062727449

Number Of Pages


  • 6

Start Page


  • 2336

End Page


  • 2342

Volume


  • 75

Issue


  • 15

Place Of Publication


  • United Kingdom

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.

UOW Authors


  •   Auranwiwat, Chiramet (external author)
  •   Maccarone, Alan (external author)
  •   Carroll, Anthony (external author)
  •   Rattanajak, Roonglawan (external author)
  •   Kamchonwongpaisan, Sumalee (external author)
  •   Blanksby, Stephen J. (external author)
  •   Pyne, Stephen
  •   Limtharakul, Thunwadee (external author)

Publication Date


  • 2019

Citation


  • 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.

Scopus Eid


  • 2-s2.0-85062727449

Number Of Pages


  • 6

Start Page


  • 2336

End Page


  • 2342

Volume


  • 75

Issue


  • 15

Place Of Publication


  • United Kingdom