Synthesis and biological activity of the dihydrotachysterol2 metabolite 25-hydroxydihydrotachysterol2.
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Biomedical subjects
Publications and source records attributed to L Castedo.
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The effects of nifedipine, papaverine and four benzylisoquinoline alkaloids (cularine, cularidine, celtisine and isocrasifoline) were studied in isolated rat uterus in order to clarify the mechanism of their relaxant action. All the compounds tested completely relaxed KCl-induced contractions and totally or partially inhibited oxytocin-induced rhythmic contractions. Only papaverine acted intracellularly, promoting relaxation of contractile responses induced by oxytocin or vanadate in a Ca(2+)-free medium. In spite of the structural relationship between papaverine and the other alkaloids, the mechanism of their relaxant action is not the same. The activities of cularine derivatives and of isocrasifoline were similar to that of nifedipine.
Eight lignans (+/-)-syringaresinol, (-)-pinoresinol, (+)-sesamin, (+)-eudesmin, (+)-epieudesmin, (-)-asarinin, (-)-matairesinol, (-)-kobusin, two terpenes lupeol, beta-sitosterol, one aliphatic unsaturated amide, hydroxy-gamma-sanshoöl, and one alkaloid, magnoflorine, were isolated from ZANTHOXYLUM species of Central and South America. Their structures were elucidated mainly by (1)H-, (13)C-NMR, and mass spectroscopy.
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Bark of Tecoma arequipensis yielded the major alkaloidal component (-)-delta-N-normethylskytanthine whose structure was proven by X-ray diffraction analysis of the N-thiourea derivative. The stereochemistry of 1 at all four centers was enantiomeric with that of skytanthine previously reported from Tecoma stans and Skytanthus acutus. Gc-ms of the crude base fraction indicated the presence of several related alkaloids as very minor constituents.