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Two Novel Plumeran Indole Alkaloids Isolated from Aspidosperma cylindrocarpon (Apocynaceae)
Author(s) -
Guimarães Heloisa A.,
Vieira Ivo J. C.,
BrazFilho Raimundo,
Crotti Antônio E. M.,
dos Almeida Vitor S.,
de Paula Renata C.
Publication year - 2013
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200522
Subject(s) - chemistry , apocynaceae , aspidosperma , indole test , alkaloid , plasmodium falciparum , stereochemistry , indole alkaloid , bark (sound) , dept , traditional medicine , medicine , physics , malaria , acoustics , immunology , biology
Two novel indole alkaloids with plumeran skeleton, N ‐benzoyl‐12‐demethoxycylindrocarine and N ‐cinnamoyl‐12‐demethoxycylindrocarine ( 1 and 2 , resp.), were isolated from the MeOH extract of the stem bark of Aspidosperma cylindrocarpon Müll . Arg . These compounds were obtained by high‐speed counter‐current chromatography, and their structures were elucidated on the basis of their NMR (1D and 2D) data. They were tested in vitro against chloroquine‐resistant strains of Plasmodium falciparum , and only 2 showed a weak activity ( IC 50 127.97 ng/ml with respect to the standard drug). Several other known compounds, comprising steroids, flavonoids, the rarely found atraric acid, as well as the previously reported alkaloid 3 , were also isolated by conventional chromatographic techniques.