Saber UCV
Repositorio Institucional
Repositorio Institucional
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https://saber.ucv.ve/handle/10872/1700
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| Title: | Ancistrocladinium A and B, the First N,C-Coupled Naphthyldihydroisoquinoline Alkaloids, from a Congolese Ancistrocladus Species |
| Authors: | Bringmann, Gerhard Kajahn, Inga Reichert, Matthias Pedersen, Sarah E. H. Faber, Johan H. Gulder, Tanja Brun, Reto Christensen, Søren B. Ponte-Sucre, Alicia Moll, Heidrun Heubl, Gu¨nther Mudogo, Virima |
| Keywords: | Naphthyldihydroisoquinoline Alkaloids Ancistrocladus Species leishmania |
| Issue Date: | 23-Aug-2012 |
| Series/Report no.: | Journal of Organic Chemistry;71: 9348-56, 2006 |
| Abstract: | The isolation and structural elucidation of three novel-type naphthylisoquinoline alkaloids, ancistrocladinium A and B (the latter along with its atropisomer), from a Congolese Ancistrocladus species collected in the habitat Yeteto is reported. Their structures, including all stereochemical features, were elucidated by spectroscopic, chemical, and chiroptical methods. Ancistrocladinium A and B are the first N,C-coupled naphthyldihydroisoquinoline alkaloids found in nature, i.e., with an iminium-aryl axis. Although ancistrocladinium A, which is N,8¢-coupled, is configurationally stable at this axis, ancistrocladinum B and its rotational isomer are based on a hitherto unprecedented N,6¢-coupling type, with a slow rotation about the hetero biaryl axis at room temperature; they thus occur as a 46:54 mixture of two configurationally semistable atropo-diastereomers. For the isomerization of (P)-ancistrocladinium B to its (M)-diastereomer and for the opposite direction, the Gibbs free energies of activation were determined to be ¢Gq 1 ) 105.8 kJ mol-1 and ¢Gq 2 ) 105.7 kJ mol-1, respectively. In addition, the compounds were shown to have promising antileishmanial activities. |
| URI: | http://hdl.handle.net/10872/1700 |
| ISSN: | 0022-3263 |
| Appears in Collections: | Artículos Publicados |
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