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
- Publication Type:
- Journal Article
- Citation:
- Journal of Natural Products, 2009, 72 (4), pp. 679 - 684
- Issue Date:
- 2009-04-24
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Filename | Description | Size | |||
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2008005050OK.pdf | 252.27 kB | Adobe PDF |
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Full metadata record
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.
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