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Tropane Alkaloids from Erythroxylum caatingae Plowman
Author(s) -
de Oliveira Steno L.,
Tavares Josean F.,
Branco Marianna V. S. Castello,
Lucena Hellane F. S.,
BarbosaFilho José M.,
de F. Agra Maria,
do Nascimento Silene C.,
dos S. Aguiar Jaciana,
da Silva Teresinha G.,
de Simone Carlos A.,
de AraújoJúnior João X.,
da Silva Marcelo S.
Publication year - 2011
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200900400
Subject(s) - tropane , chemistry , alkaloid , stereochemistry , hydrochloride , biochemistry
Three tropane alkaloids, 1 – 3 , were isolated from Erythroxylum caatingae, i.e. , 6 β ‐benzoyloxy‐3 α ‐[(4‐hydroxy‐3,5‐dimethoxybenzoyl)oxy]tropane ( 1 ), a new tropane alkaloid, along with the known alkaloids 3 α ,6 β ‐dibenzoyloxytropane ( 2 ) and 6 β ‐benzoyloxy‐3 α ‐[(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. , 6 β ‐benzoyloxy‐3 α ‐(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.