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Semisynthesis and biological activity of stemofoline alkaloids

Journal Article


Abstract


  • The semisynthesis of the Stemona alkaloids (3'R)-stemofolenol (1). (3'S)-stemofolenol (2), methylstemofoline (3), and (3'S)-hydroxystemofoline (5) and the unnatural analogues (11E)-methylstemofoline (15) and 3'R-hydroxystemofoline (11) has been achieved starting from (11Z)-1',2'-didehydrostemofoline (4). This synthesis allowed, for the first time, access to diastereomerically enriched samples of 1 and 2 and the assignment of their absolute configurations at C-3'. These compounds were obtained in sufficient quantities to allow for their biological testing. In a quantitative assay as AChE inhibitors, (11Z)-1',2'-didehydrostemofoline (4) and (3'S)-hydroxystemofoline (5) were found to be the most active.

UOW Authors


  •   Baird, Morwenna C. (external author)
  •   Pyne, Stephen
  •   Ung, Alison T. (external author)
  •   Lie, Wilford
  •   Sastraruji, Thanapat (external author)
  •   Jatisatienr, Araya (external author)
  •   Jatisatienr, Chaiwat (external author)
  •   Dheeranupattana, Srisulak (external author)
  •   Lowlam, Jaturong (external author)
  •   Boonchalermkit, Sukanya (external author)

Publication Date


  • 2009

Citation


  • Baird, M. C., Pyne, S. G., Ung, A. T., Lie, W., Sastraruji, T., Jatisatienr, A., Jatisatienr, C., Dheeranupattana, S., Lowlam, J. & Boonchalermkit, S. (2009). Semisynthesis and biological activity of stemofoline alkaloids. Journal of Natural Products, 72 (4), 679-684.

Scopus Eid


  • 2-s2.0-65649116635

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/4577

Number Of Pages


  • 5

Start Page


  • 679

End Page


  • 684

Volume


  • 72

Issue


  • 4

Abstract


  • The semisynthesis of the Stemona alkaloids (3'R)-stemofolenol (1). (3'S)-stemofolenol (2), methylstemofoline (3), and (3'S)-hydroxystemofoline (5) and the unnatural analogues (11E)-methylstemofoline (15) and 3'R-hydroxystemofoline (11) has been achieved starting from (11Z)-1',2'-didehydrostemofoline (4). This synthesis allowed, for the first time, access to diastereomerically enriched samples of 1 and 2 and the assignment of their absolute configurations at C-3'. These compounds were obtained in sufficient quantities to allow for their biological testing. In a quantitative assay as AChE inhibitors, (11Z)-1',2'-didehydrostemofoline (4) and (3'S)-hydroxystemofoline (5) were found to be the most active.

UOW Authors


  •   Baird, Morwenna C. (external author)
  •   Pyne, Stephen
  •   Ung, Alison T. (external author)
  •   Lie, Wilford
  •   Sastraruji, Thanapat (external author)
  •   Jatisatienr, Araya (external author)
  •   Jatisatienr, Chaiwat (external author)
  •   Dheeranupattana, Srisulak (external author)
  •   Lowlam, Jaturong (external author)
  •   Boonchalermkit, Sukanya (external author)

Publication Date


  • 2009

Citation


  • Baird, M. C., Pyne, S. G., Ung, A. T., Lie, W., Sastraruji, T., Jatisatienr, A., Jatisatienr, C., Dheeranupattana, S., Lowlam, J. & Boonchalermkit, S. (2009). Semisynthesis and biological activity of stemofoline alkaloids. Journal of Natural Products, 72 (4), 679-684.

Scopus Eid


  • 2-s2.0-65649116635

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/4577

Number Of Pages


  • 5

Start Page


  • 679

End Page


  • 684

Volume


  • 72

Issue


  • 4