Literature DB >> 21259426

Tropane alkaloids from Erythroxylum caatingae Plowman.

Steno L de Oliveira1, Josean F Tavares, Marianna V S Castello Branco, Hellane F S Lucena, José M Barbosa-Filho, Maria de F Agra, Silene C do Nascimento, Jaciana dos S Aguiar, Teresinha G da Silva, Carlos A de Simone, João X de Araújo-Júnior, Marcelo S da Silva.   

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.
Copyright © 2011 Verlag Helvetica Chimica Acta AG, Zürich.

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Year:  2011        PMID: 21259426     DOI: 10.1002/cbdv.200900400

Source DB:  PubMed          Journal:  Chem Biodivers        ISSN: 1612-1872            Impact factor:   2.408


  5 in total

1.  Antimicrobial, antiproliferative and proapoptotic activities of extract, fractions and isolated compounds from the stem of Erythroxylum caatingae plowman.

Authors:  Jaciana S Aguiar; Rosilma O Araújo; Maria Do Desterro Rodrigues; Kêsia X F R Sena; André M Batista; Maria M P Guerra; Steno L Oliveira; Josean F Tavares; Marcelo S Silva; Silene C Nascimento; Teresinha Gonçalves Da Silva
Journal:  Int J Mol Sci       Date:  2012-03-29       Impact factor: 6.208

2.  Chirality and numbering of substituted tropane alkaloids.

Authors:  Munir Humam; Tarik Shoul; Damien Jeannerat; Orlando Muñoz; Philippe Christen
Journal:  Molecules       Date:  2011-08-25       Impact factor: 4.411

Review 3.  Erythroxylum in Focus: An Interdisciplinary Review of an Overlooked Genus.

Authors:  David A Restrepo; Ernesto Saenz; Orlando Adolfo Jara-Muñoz; Iván F Calixto-Botía; Sioly Rodríguez-Suárez; Pablo Zuleta; Benjamin G Chavez; Juan A Sanchez; John C D'Auria
Journal:  Molecules       Date:  2019-10-21       Impact factor: 4.411

Review 4.  Advances in chemistry and bioactivity of the genus Erythroxylum.

Authors:  Yulian Lv; Tian Tian; Yong-Jiang Wang; Jian-Ping Huang; Sheng-Xiong Huang
Journal:  Nat Prod Bioprospect       Date:  2022-04-14

Review 5.  Indole alkaloids from marine sources as potential leads against infectious diseases.

Authors:  Paulo H B França; Daniel P Barbosa; Daniel L da Silva; Êurica A N Ribeiro; Antônio E G Santana; Bárbara V O Santos; José M Barbosa-Filho; Jullyana S S Quintans; Rosana S S Barreto; Lucindo J Quintans-Júnior; João X de Araújo-Júnior
Journal:  Biomed Res Int       Date:  2014-06-05       Impact factor: 3.411

  5 in total

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