Semisynthesis and biological activity of stemofoline alkaloids

Baird, MC; Pyne, SG; Ung, AT; Lie, W; Sastraruji, T; Jatisatienr, A; Jatisatienr, C; Dheeranupattana, S; Lowlam, J; Boonchalermkit, S

Semisynthesis and biological activity of stemofoline alkaloids

Baird, MC Pyne, SG Ung, AT

Lie, W Sastraruji, T Jatisatienr, A Jatisatienr, C Dheeranupattana, S Lowlam, J Boonchalermkit, S

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Publication Type:: Journal Article
Citation:: Journal of Natural Products, 2009, 72 (4), pp. 679 - 684
Issue Date:: 2009-04-24

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Field	Value	Language
dc.contributor.author	Baird, MC	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	Lie, W	en_US
dc.contributor.author	Sastraruji, T	en_US
dc.contributor.author	Jatisatienr, A	en_US
dc.contributor.author	Jatisatienr, C	en_US
dc.contributor.author	Dheeranupattana, S	en_US
dc.contributor.author	Lowlam, J	en_US
dc.contributor.author	Boonchalermkit, S	en_US
dc.date.issued	2009-04-24	en_US
dc.identifier.citation	Journal of Natural Products, 2009, 72 (4), pp. 679 - 684	en_US
dc.identifier.issn	0163-3864	en_US
dc.identifier.uri	http://hdl.handle.net/10453/11793
dc.description.abstract	The semisynthesis of the Stemona alkaloids (3′R)-stemofolenol (1), (3′S)-stemofolenol (2), methylstemofoline (3), and (3′S)- hydroxystemofoline (5) and the unnatural analogues (11E)-methylstemofoline (15) and 3′R-hydroxystemofoline (11) has been achieved starting from (11Z)-1′,2′-didehydrostemofoline (4). This synthesis allowed, for the first time, access to diastereomerically enriched samples of 1 and 2 and the assignment of their absolute configurations at C-3′. These compounds were obtained in sufficient quantities to allow for their biological testing. In a quantitative assay as AChE inhibitors, (11Z)-1′,2′- didehydrostemofoline (4) and (3′S)-hydroxystemofoline (5) were found to be the most active. © 2009 American Chemical Society and American Society of Pharmacognosy.	en_US
dc.relation.ispartof	Journal of Natural Products	en_US
dc.relation.isbasedon	10.1021/np800806b	en_US
dc.subject.classification	Medicinal & Biomolecular Chemistry	en_US
dc.subject.mesh	Pseudomonas aeruginosa	en_US
dc.subject.mesh	Escherichia coli	en_US
dc.subject.mesh	Staphylococcus aureus	en_US
dc.subject.mesh	Candida albicans	en_US
dc.subject.mesh	Stemonaceae	en_US
dc.subject.mesh	Alkaloids	en_US
dc.subject.mesh	Cholinesterase Inhibitors	en_US
dc.subject.mesh	Heterocyclic Compounds, 4 or More Rings	en_US
dc.subject.mesh	Microbial Sensitivity Tests	en_US
dc.subject.mesh	Molecular Structure	en_US
dc.subject.mesh	Nuclear Magnetic Resonance, Biomolecular	en_US
dc.subject.mesh	Stereoisomerism	en_US
dc.title	Semisynthesis and biological activity of stemofoline alkaloids	en_US
dc.type	Journal Article
utslib.citation.volume	4	en_US
utslib.citation.volume	72	en_US
utslib.for	1101 Medical Biochemistry and Metabolomics	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	4	en_US
pubs.publication-status	Published	en_US
pubs.volume	72	en_US

Abstract:

The semisynthesis of the Stemona alkaloids (3′R)-stemofolenol (1), (3′S)-stemofolenol (2), methylstemofoline (3), and (3′S)- hydroxystemofoline (5) and the unnatural analogues (11E)-methylstemofoline (15) and 3′R-hydroxystemofoline (11) has been achieved starting from (11Z)-1′,2′-didehydrostemofoline (4). This synthesis allowed, for the first time, access to diastereomerically enriched samples of 1 and 2 and the assignment of their absolute configurations at C-3′. These compounds were obtained in sufficient quantities to allow for their biological testing. In a quantitative assay as AChE inhibitors, (11Z)-1′,2′- didehydrostemofoline (4) and (3′S)-hydroxystemofoline (5) were found to be the most active. © 2009 American Chemical Society and American Society of Pharmacognosy.

Please use this identifier to cite or link to this item:

http://hdl.handle.net/10453/11793