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Phytochemical Investigations of Stemona curtisii and Synthetic Studies on Stemocurtisine Alkaloids

Journal Article


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Abstract


  • The isolation of two new Stemona alkaloids, 1-hydroxyprotostemonine and stemocurtisine N-oxide, and a new benzofuran, stemofuran L, from the root extracts of Stemona curtisii is reported. The major known alkaloids from this plant extract, stemocurtisine, stemocurtisinol, and oxyprotostemonine, were also isolated along with oxystemokerrine N-oxide. The nonalkaloid components of this extract included a new benzofuran derivative, stemofuran L, the known stemofurans F, J, and K, dihydro-γ-tocopherol, and stigmasterol. Stemocurtisine and stemocurtisinol were converted to their respective N-oxides by oxidation. Stemocurtisine was converted to a tetracyclic derivative by oxidative cleavage of the γ-butyrolactone ring, while stemocurtisinol gave a novel lactam derivative by oxidative cleavage of the C-4 side chain under basic conditions. The acetylcholinesterase inhibitory activities of some known and new alkaloids and their derivatives are also reported. All were 10−20 times less active as acetylcholinesterase inhibitors than the pyrrolo[1,2-a]azepine Stemona alkaloids stemofoline and 1′,2′-didehydrostemofoline. None of the stemofuran compounds showed significant antibacterial or antifungal activities.

UOW Authors


  •   Chaiyong, Sukanda (external author)
  •   Jatisatienr, Araya (external author)
  •   Mungkornasawakul, Pitchaya (external author)
  •   Sastraruji, Thanapat (external author)
  •   Pyne, Stephen
  •   Ung, Alison T. (external author)
  •   Urathamakul, Thitima (external author)
  •   Lie, Wilford

Publication Date


  • 2010

Citation


  • Chaiyong, S., Jatisatienr, A., Mungkornasawakul, P., Sastraruji, T., Pyne, S. G., Ung, A. T., Urathamakul, T. & Lie, W. (2010). Phytochemical Investigations of Stemona curtisii and Synthetic Studies on Stemocurtisine Alkaloids. Journal of Natural Products, 73 (11), 1833-1838.

Scopus Eid


  • 2-s2.0-78650219547

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=1667&context=scipapers

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/628

Number Of Pages


  • 5

Start Page


  • 1833

End Page


  • 1838

Volume


  • 73

Issue


  • 11

Abstract


  • The isolation of two new Stemona alkaloids, 1-hydroxyprotostemonine and stemocurtisine N-oxide, and a new benzofuran, stemofuran L, from the root extracts of Stemona curtisii is reported. The major known alkaloids from this plant extract, stemocurtisine, stemocurtisinol, and oxyprotostemonine, were also isolated along with oxystemokerrine N-oxide. The nonalkaloid components of this extract included a new benzofuran derivative, stemofuran L, the known stemofurans F, J, and K, dihydro-γ-tocopherol, and stigmasterol. Stemocurtisine and stemocurtisinol were converted to their respective N-oxides by oxidation. Stemocurtisine was converted to a tetracyclic derivative by oxidative cleavage of the γ-butyrolactone ring, while stemocurtisinol gave a novel lactam derivative by oxidative cleavage of the C-4 side chain under basic conditions. The acetylcholinesterase inhibitory activities of some known and new alkaloids and their derivatives are also reported. All were 10−20 times less active as acetylcholinesterase inhibitors than the pyrrolo[1,2-a]azepine Stemona alkaloids stemofoline and 1′,2′-didehydrostemofoline. None of the stemofuran compounds showed significant antibacterial or antifungal activities.

UOW Authors


  •   Chaiyong, Sukanda (external author)
  •   Jatisatienr, Araya (external author)
  •   Mungkornasawakul, Pitchaya (external author)
  •   Sastraruji, Thanapat (external author)
  •   Pyne, Stephen
  •   Ung, Alison T. (external author)
  •   Urathamakul, Thitima (external author)
  •   Lie, Wilford

Publication Date


  • 2010

Citation


  • Chaiyong, S., Jatisatienr, A., Mungkornasawakul, P., Sastraruji, T., Pyne, S. G., Ung, A. T., Urathamakul, T. & Lie, W. (2010). Phytochemical Investigations of Stemona curtisii and Synthetic Studies on Stemocurtisine Alkaloids. Journal of Natural Products, 73 (11), 1833-1838.

Scopus Eid


  • 2-s2.0-78650219547

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=1667&context=scipapers

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/628

Number Of Pages


  • 5

Start Page


  • 1833

End Page


  • 1838

Volume


  • 73

Issue


  • 11