Semisynthesis and acetylcholinesterase inhibitory activity of stemofoline alkaloids and analogues.
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)-hydroxystemofoline (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.
Sastraruji
Kwankamol
K
School of Chemistry, University of Wollongong, Wollongong, New South Wales, 2522, Australia.
Sastraruji
Thanapat
T
Pyne
Stephen G
SG
Ung
Alison T
AT
Jatisatienr
Araya
A
Lie
Wilford
W
D000470:Alkaloids / Q000737:chemistry / Q000494:pharmacology; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D020650:Combinatorial Chemistry Techniques; D005702:Galantamine / Q000494:pharmacology; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D041901:Stemonaceae / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D002800:Cholinesterase Inhibitors; D006576:Heterocyclic Compounds, 4 or More Rings; D005702:Galantamine; C430220:stemofoline