Indole alkaloids are the chemotaxonomic markers of the Aspidosperma genera. Those that have the simplest plumeran skeleton are classified as the precursors of biosynthetic routes and the intermediates for several synthetic reactions. This work aims to review the 1 H and 13 C-NMR data, up to 2011, describing the skeleton of 35 different plumeran indole alkaloids, from a group of 46 of them, and highlight the main spectral differences amongst them.
Binding between bovine serum albumin (BSA) and a plumeran indole alkaloid (PIA) isolated from the stem bark of Aspidosperma cylindrocarpon (Apocynaceae) was studied by spectroscopic techniques (UV-Vis absorption, circular dichroism, steady state and time-resolved fluorescence), combined with molecular docking. Steady state and time resolved fluorescence data revealed that PIA can quench the BSA fluorescence via a static mechanism: energy transfer from BSA to PIA occurs with high probability. The binding is strong (K b ca. 10 5 -10 6 L mol -1 ), spontaneous (ΔG° ca. -35.7 kJ mol -1 at 310 K) and entropy-driven (ΔS° = 0.146 kJ mol -1 K -1 ). There is just one main binding site (n ca. 1) for the BSA:PIA interaction and the α-helix content of the albumin does not suffer significant perturbation upon PIA binding. Molecular docking results suggest site I as the main binding site to PIA, which is able to interact with the Trp-212, Arg-217, Val-342 and Pro-446 residues.
RESUMO: "Efeitos do extrato etanólico das folhas de Lafoensia pacari A. St.-Hil., Lythraceae (pacari), em modelos de dor e inflamação". O pacari (Lafoensia pacari A. St.-Hil., Lythraceae) é uma espécie vegetal nativa do cerrado, o extrato da casca de caule é utilizado popularmente para dores e inflamação, tendo mostrado atividade sedativa. Este trabalho objetivou avaliar os efeitos do extrato etanólico das folhas do pacari (EEFP) como analgésico e antiinflamatório. As atividades analgésica e antiinflamatória foram verificadas em camundongos. O tratamento prévio com EEFP 1,0 g/kg mostrou atividade antinociceptiva tanto no método das contorções abdominais induzidas por ácido acético como também no modelo de dor induzida por formalina, tanto na fase neurogênica quanto na fase inflamatória. Os pré-tratamentos com o EEFP reduziram o edema de orelha, induzido por óleo de cróton, de forma dose-dependente. Os testes de atividade no sistema nervoso central mostraram que o extrato não provoca incoordenação motora nem hipnose ou sedação. Os resultados mostram que o EEFP mantém as atividades analgésica e antiinflamatória do extrato das cascas do caule do pacari, sendo que a coleta das folhas favorece a preservação desta espécie nativa do cerrado.Unitermos: Dor, inflamação, extrato das folhas, Lafoensia pacari, Lythraceae.ABSTRACT: Lafoensia pacari A. St.-Hil., Lythraceae, popularly known as pacari, is a Cerrado's native specimen; the stem bark extract is used in folk for pain and inflammation, also showing sedating activity. This study aimed to evaluate the analgesic and anti inflammatory activities of ethanol extract from pacari leaves (EEPL). These activities were verified in mice. The previous treatment with EEPL 1.0 g/kg showed antinociceptive activity both in the acetic acid-induced writing test and in the formalin-induced model of pain, and in neurogenic and inflammatory phases as well. In the croton oil-induced ear edema, the pre-treatments with EEPL reduced the edema in a dose-dependent manner. Also in the carrageenan-induced peritonitis, the two major doses tested (2.0 and 1.5 g/kg p.o.) were able to reduce the leukocyte migration in a dose-dependent manner. The Central Nervous System tests showed that the extract does not elicit uncoordinated motricity, hypnosis or sedating effects. The results showed that EEPL maintains the analgesic and anti-inflammatory effects of the stem bark of pacari, being the collect of leaves more favorable to the preservation of this Cerrado's native specimen.
Two Novel Plumeran Indole Alkaloids Isolated from Aspidosperma cylindrocarpon (Apocynaceae) -[isolation, structure determination and antimalarial activity]. -(GUIMARAES*, H. A.; VIEIRA, I. J. C.; BRAZ-FILHO, R.; CROTTI, A. E. M.; DOS S. ALMEIDA, V.; DE PAULA, R. C.; Helv. Chim. Acta 96 (2013) 9, 1793-1800, http://dx.doi.org/10.1002/hlca.201200522 ; Lab. Cienc. Quim., Cent. Cienc. Tecnol., Univ. Estadual Norte Fluminense, Campos, 28013 Rio de Janeiro, Brazil; Eng.) -M. Paetzel 07-228
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 (IC50 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.
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