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Chem Biodivers ; 8(1): 155-65, 2011 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-21259426

RESUMEN

Three tropane alkaloids, 1-3, were isolated from Erythroxylum caatingae, i.e., 6ß-benzoyloxy-3α-[(4-hydroxy-3,5-dimethoxybenzoyl)oxy]tropane (1), a new tropane alkaloid, along with the known alkaloids 3α,6ß-dibenzoyloxytropane (2) and 6ß-benzoyloxy-3α-[(3,4,5-trimethoxybenzoyl)oxy]tropane (catuabine B; 3). Their structures were determined by 2D- ((1) H and (13) C) NMR. By LC/ESI-MS/MS analysis of the fractions of alkaloids 1-3, it was possible to detect five more alkaloids, 4-8, two of these, 4 and 8, possibly being new natural products. X-Ray crystallography of the chloride derivate of 1, i.e., 6ß-benzoyloxy-3α-(4-hydroxy-3,5-dimethoxybenzoyloxy)tropane hydrochloride (1a) confirmed the structure of 1. Cytotoxicity was tested against the cell lines HEp-2, NCI-H292, and KB for the MeOH extract and alkaloid 3, and antitumor activity was tested against Sarcoma 180 only for the MeOH extract.


Asunto(s)
Antineoplásicos Fitogénicos/química , Erythroxylaceae/química , Tropanos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/toxicidad , Línea Celular Tumoral , Cristalografía por Rayos X , Humanos , Espectroscopía de Resonancia Magnética , Conformación Molecular , Tallos de la Planta/química , Tropanos/aislamiento & purificación , Tropanos/toxicidad
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