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Semisynthesis and acetylcholinesterase inhibitory activity of stemofoline alkaloids and analogues

Journal Article


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Abstract


  • Semisynthesis of the known Stemona alkaloids oxystemofoline (7) and methoxystemofoline (8) has been achieved starting from (11Z)-1',2'-didehydrostemofoline (6). which confirmed their structures and absolute configurations. The synthesis of (1'R)-hydroxystemololine (9) helped establish this compound as a natural product from Stemona aphylla. (1'S)-Hydroxystemofoline (10) and a number of related analogues were also prepared. In a TLC bioautographic assay, 9 was found to be the most active acetylcholinesterase inhibitor, but it was not as active as galanthamine.

UOW Authors


  •   Sastraruji, Kwankamol (external author)
  •   Sastraruji, Thanapat (external author)
  •   Pyne, Stephen
  •   Ung, Alison T. (external author)
  •   Jatisatienr, Araya (external author)
  •   Lie, Wilford

Publication Date


  • 2010

Citation


  • Sastraruji, K., Sastraruji, T., Pyne, S. G., Ung, A. T., Jatisatienr, A. & Lie, W. (2010). Semisynthesis and acetylcholinesterase inhibitory activity of stemofoline alkaloids and analogues. Journal of Natural Products, 73 (5), 935-941.

Scopus Eid


  • 2-s2.0-77952982010

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=2206&context=scipapers

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/1139

Number Of Pages


  • 6

Start Page


  • 935

End Page


  • 941

Volume


  • 73

Issue


  • 5

Abstract


  • Semisynthesis of the known Stemona alkaloids oxystemofoline (7) and methoxystemofoline (8) has been achieved starting from (11Z)-1',2'-didehydrostemofoline (6). which confirmed their structures and absolute configurations. The synthesis of (1'R)-hydroxystemololine (9) helped establish this compound as a natural product from Stemona aphylla. (1'S)-Hydroxystemofoline (10) and a number of related analogues were also prepared. In a TLC bioautographic assay, 9 was found to be the most active acetylcholinesterase inhibitor, but it was not as active as galanthamine.

UOW Authors


  •   Sastraruji, Kwankamol (external author)
  •   Sastraruji, Thanapat (external author)
  •   Pyne, Stephen
  •   Ung, Alison T. (external author)
  •   Jatisatienr, Araya (external author)
  •   Lie, Wilford

Publication Date


  • 2010

Citation


  • Sastraruji, K., Sastraruji, T., Pyne, S. G., Ung, A. T., Jatisatienr, A. & Lie, W. (2010). Semisynthesis and acetylcholinesterase inhibitory activity of stemofoline alkaloids and analogues. Journal of Natural Products, 73 (5), 935-941.

Scopus Eid


  • 2-s2.0-77952982010

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=2206&context=scipapers

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/1139

Number Of Pages


  • 6

Start Page


  • 935

End Page


  • 941

Volume


  • 73

Issue


  • 5