Semisynthesis and acetylcholinesterase inhibitory activity of stemofoline alkaloids and analogues

Sastraruji, K; Sastraruji, T; Pyne, SG; Ung, AT; Jatisatienr, A; Lie, W

Semisynthesis and acetylcholinesterase inhibitory activity of stemofoline alkaloids and analogues

Sastraruji, K Sastraruji, T Pyne, SG Ung, AT

Jatisatienr, A Lie, W

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Publication Type:: Journal Article
Citation:: Journal of Natural Products, 2010, 73 (5), pp. 935 - 941
Issue Date:: 2010-05-28

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Field	Value	Language
dc.contributor.author	Sastraruji, K	en_US
dc.contributor.author	Sastraruji, T	en_US
dc.contributor.author	Pyne, SG	en_US
dc.contributor.author	Ung, AT https://orcid.org/0000-0002-5665-0702	en_US
dc.contributor.author	Jatisatienr, A	en_US
dc.contributor.author	Lie, W	en_US
dc.date.issued	2010-05-28	en_US
dc.identifier.citation	Journal of Natural Products, 2010, 73 (5), pp. 935 - 941	en_US
dc.identifier.issn	0163-3864	en_US
dc.identifier.uri	http://hdl.handle.net/10453/13381
dc.description.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. © 2010 The American Chemical Society and American Society of Pharmacognosy.	en_US
dc.relation.ispartof	Journal of Natural Products	en_US
dc.relation.isbasedon	10.1021/np100137h	en_US
dc.subject.classification	Medicinal & Biomolecular Chemistry	en_US
dc.subject.mesh	Stemonaceae	en_US
dc.subject.mesh	Alkaloids	en_US
dc.subject.mesh	Galantamine	en_US
dc.subject.mesh	Cholinesterase Inhibitors	en_US
dc.subject.mesh	Combinatorial Chemistry Techniques	en_US
dc.subject.mesh	Heterocyclic Compounds, 4 or More Rings	en_US
dc.subject.mesh	Molecular Structure	en_US
dc.subject.mesh	Stereoisomerism	en_US
dc.title	Semisynthesis and acetylcholinesterase inhibitory activity of stemofoline alkaloids and analogues	en_US
dc.type	Journal Article
utslib.citation.volume	5	en_US
utslib.citation.volume	73	en_US
utslib.for	0305 Organic Chemistry	en_US
utslib.for	03 Chemical Sciences	en_US
utslib.for	06 Biological Sciences	en_US
utslib.for	11 Medical and Health Sciences	en_US
pubs.embargo.period	Not known	en_US
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
pubs.organisational-group	/University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
pubs.organisational-group	/University of Technology Sydney/Strength - CCET - Centre for Clean Energy Technology
utslib.copyright.status	closed_access
pubs.issue	5	en_US
pubs.publication-status	Published	en_US
pubs.volume	73	en_US

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. © 2010 The American Chemical Society and American Society of Pharmacognosy.

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http://hdl.handle.net/10453/13381