Tropane alkaloids from Erythroxylum caatingae Plowman.
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.
Departamento de Ciências Farmacêuticas, Laboratório de Tecnologia Farmacêutica, Universidade Federal da Paraíba, João Pessoa, Paraíba, Brazil.
Steno L
SL
de Oliveira
Josean F
JF
Tavares
Marianna V S Castello
MV
Branco
Hellane F S
HF
Lucena
José M
JM
Barbosa-Filho
Maria
M
de F Agra
Silene C
SC
do Nascimento
Jaciana
J
dos S Aguiar
Teresinha G
TG
da Silva
Carlos A
CA
de Simone
João X
JX
de Araújo-Júnior
Marcelo S
MS
da Silva
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D045744:Cell Line, Tumor; D018360:Crystallography, X-Ray; D030921:Erythroxylaceae / Q000737:chemistry*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D018547:Plant Stems / Q000737:chemistry; D014326:Tropanes / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity
C557951:6beta-benzoyloxy-3alpha-((4-hydroxy-3,5-dimethoxybenzoyl)oxy)tropane; D000972:Antineoplastic Agents, Phytogenic; D014326:Tropanes