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Tropane alkaloids from Erythroxylum caatingae Plowman
Authors:de Oliveira Steno L  Tavares Josean F  Branco Marianna V S Castello  Lucena Hellane F S  Barbosa-Filho José M  de F Agra Maria  do Nascimento Silene C  dos S Aguiar Jaciana  da Silva Teresinha G  de Simone Carlos A  de Araújo-Júnior João X  da Silva Marcelo S
Affiliation:Departamento de Ciências Farmacêuticas, Laboratório de Tecnologia Farmacêutica, Universidade Federal da Paraíba, Jo?o Pessoa, Paraíba, Brazil.
Abstract:Three tropane alkaloids, 1-3, were isolated from Erythroxylum caatingae, i.e., 6β-benzoyloxy-3α-[(4-hydroxy-3,5-dimethoxybenzoyl)oxy]tropane (1), a new tropane alkaloid, along with the known alkaloids 3α,6β-dibenzoyloxytropane (2) and 6β-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., 6β-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.
Keywords:Erythroxylum caatingae  Alkaloids  Tropane alkaloids  X‐Ray crystallography
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