Australine and related alkaloids: easy structural confirmation by C-13 NMR spectral data and biological activities

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dc.contributor.author Kato, Atsushi
dc.contributor.author Kano, E.
dc.contributor.author Adachi, Isao
dc.contributor.author Molyneux, R. J.
dc.contributor.author Watson, Alison A.
dc.contributor.author Nash, Robert J.
dc.contributor.author Fleet, George W. J.
dc.contributor.author Wormald, M. R.
dc.contributor.author Kizu, Haruhisa
dc.contributor.author Ikeda, Kyoko
dc.contributor.author Asano, Naoki
dc.date.accessioned 2010-03-03T16:25:27Z
dc.date.available 2010-03-03T16:25:27Z
dc.date.issued 2003-02-07
dc.identifier.citation Kato , A , Kano , E , Adachi , I , Molyneux , R J , Watson , A A , Nash , R J , Fleet , G W J , Wormald , M R , Kizu , H , Ikeda , K & Asano , N 2003 , ' Australine and related alkaloids: easy structural confirmation by C-13 NMR spectral data and biological activities ' Tetrahedron: Asymmetry , vol 14 , no. 3 , pp. 325-331 . en
dc.identifier.issn 0957-4166
dc.identifier.other PURE: 137005
dc.identifier.other dspace: 2160/4155
dc.identifier.uri http://hdl.handle.net/2160/4155
dc.description Kato, A., Kano, E., Adachi, I., Molyneux, R. J., Watson, A. A., Nash, R. J., Fleet, G. W. J., Wormald, M. R., Kizu, H., Ikeda, K., Asano, N. (2003). Australine and related alkaloids: easy structural confirmation by C-13 NMR spectral data and biological activities. Tetrahedron Asymmetry, 14 (3), 325-331. en
dc.description.abstract The first polyhydroxylated pyrrolizidine alkaloid with a hydroxymethyl group at C-3 was isolated from pods of Alexa leiopetala (Leguminosae) and designated alexine 1. The Australian legume Castanospermum australe is also known to produce the same structural type of pyrrolizidines. There are reports of the isolation of australine (7a-epi-alexine) 2, 1-epi-australine 3, 3-epi-australine 4, and 7-epi-australine 5 from this plant to date. Their unambiguous syntheses established that the natural product reported as 5 is 2 and the published NMR data for 2 are those of 3. These confusions prompted us to unambiguously confirm the structures and biological activities of australine isomers and related alkaloids. A careful search for polyhydroxylated pyrrolizidines in seeds of C. australe led to the discovery of three new alkaloids, 2,3-diepi-australine 6, 2,3,7-triepi-australine 7, and the 2-O-β- -glucopyranoside of 3 (8). Herein, we report the full 13C NMR assignment of alkaloids 1–8 and the glycosidase inhibitory activities of alkaloids 1–8 together with the highly oxygenated pyrrolizidine, casuarine 9, and its 6-O-α- -glucopyranoside 10 en
dc.format.extent 7 en
dc.language.iso eng
dc.relation.ispartof Tetrahedron: Asymmetry en
dc.title Australine and related alkaloids: easy structural confirmation by C-13 NMR spectral data and biological activities en
dc.type Text en
dc.type.publicationtype Article (Journal) en
dc.identifier.doi http://dx.doi.org/10.1016/S0957-4166(02)00799-1
dc.contributor.institution Aberystwyth University en
dc.contributor.institution Institute of Biological, Environmental and Rural Sciences en
dc.description.status Peer reviewed en


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