Semisynthesis and acetylcholinesterase inhibitory activity of stemofoline alkaloids and analogues

Kwankamol Sastraruji; Thanapat Sastraruji; Stephen G Pyne; Alison T Ung; Araya Jatisatienr; Wilford Lie

doi:10.1021/np100137h

Semisynthesis and acetylcholinesterase inhibitory activity of stemofoline alkaloids and analogues

J Nat Prod. 2010 May 28;73(5):935-41. doi: 10.1021/np100137h.

Authors

Kwankamol Sastraruji¹, Thanapat Sastraruji, Stephen G Pyne, Alison T Ung, Araya Jatisatienr, Wilford Lie

Affiliation

¹ School of Chemistry, University of Wollongong, Wollongong, New South Wales, 2522, Australia.

PMID: 20415428
DOI: 10.1021/np100137h

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)-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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemistry
Alkaloids / pharmacology
Cholinesterase Inhibitors / chemical synthesis*
Cholinesterase Inhibitors / chemistry
Cholinesterase Inhibitors / pharmacology*
Combinatorial Chemistry Techniques*
Galantamine / pharmacology
Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
Heterocyclic Compounds, 4 or More Rings / chemistry
Heterocyclic Compounds, 4 or More Rings / pharmacology*
Molecular Structure
Stemonaceae / chemistry*
Stereoisomerism

Substances

Alkaloids
Cholinesterase Inhibitors
Heterocyclic Compounds, 4 or More Rings
Galantamine
stemofoline