Oxidative burst inhibitory and cytotoxic amides and lignans from the stem bark of Fagara heitzii (Rutaceae)
Two amides, heitziamide A and heitziamide B and two phenylethanoids, heitziethanoid A and heitziethanoid B together with thirteen known compounds were isolated from F. heitzii (Letouzey). The structures of all compounds were established by spectroscopic analysis. Nine compounds were evaluated for oxidative burst inhibitory activity in a chemoluminescence assay and for cytotoxicity against PC-3 prostate cancer cells. All compounds exhibited a clear suppressive effect on phagocytosis response upon activation with serum opsonized zymosan at the range of IC50 = 2.0-6.5 mu M, but no cytotoxic effect was observed (IC50 > 100 mu M). (C) 2009 Elsevier Ltd. All rights reserved.
Pentapeptides containing two dehydrophenylalanine residues - synthesis, structural studies and evaluation of their activity towards cathepsin C
Synthesis, structural and biological studies of pentapeptides containing two Delta Phe residues (Z and E isomers) in position 2 and 4 in peptide chain were performed. All the investigated peptides adopted bent conformation and majority of them could exist as two different. conformers in solution. Only pentapeptides. containing free N-termini appeared to act as weak inhibitors of cathepsin C with the slow-binding, competitive mechanism of inhibition. free acids being bound slightly better than their methyl esters. Results of Molecular modeling suggested significant difference between peptides, depending of the type of amino acid residue in position 5 in peptide chain. Dehydropeptides contain…
Constituents of Peperomia vulcanica Baker & C. H. Wright (Piperaceae) with antiparasitic activity
Abstract The investigation of the CH2Cl2-MeOH (1:1) extract of Peperomia vulcanica which showed antileishmanial activity during preliminary screening led to the isolation of two previously unknown compounds named peperolignan (1) and peperotannin (2) along with 13 known compounds. Their structures were determined on the basis of their spectroscopic data. The isolated compounds were assessed in vitro for their antileishmanial and antiplasmodial activities against Leishmania donovani 1S (MHOM/SD/62/1S) promastigotes and the Plasmodium falciparum chloroquine-sensitive 3D7 strain (Pf3D7), respectively. They were also assessed for their cytotoxicity on Raw 264.7 macrophage cells. The mixture of …
VCD studies on cyclic peptides assembled from L-α-amino acids and a trans-2-aminocyclopentane- or trans-2-aminocyclohexane carboxylic acid.
The increasing interest in peptidomimetics of biological relevance prompted us to synthesize a series of cyclic peptides comprising trans-2-aminocyclohexane carboxylic acid (Achc) or trans-2-aminocyclopentane carboxylic acid (Acpc). NMR experiments in combination with MD calculations were performed to investigate the three-dimensional structure of the cyclic peptides. These data were compared to the conformational information obtained by electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectroscopy. Experimental VCD spectra were compared to theoretical VCD spectra computed quantum chemically at B3LYP/6-31G(d) density functional theory (DFT) level. The good agreem…
C-28/C-30 oxidized cycloartanes from the leaves and twigs of Caloncoba dusenii Gilg
Abstract Four hitherto unreported cycloartane-type triterpenes (1-4) with C-28/C-30 oxidized methyl groups together with two known compounds (5-6) have been obtained from the leaves and twigs of Caloncoba dusenii Gilg. The compounds were isolated through extraction and silica gel column chromatography. Their structures and relative stereochemistry were determined by extensive use of spectroscopic techniques including IR, 1D and 2D-NMR as well as mass spectrometry. This is the first report of C-28/C-30 oxidized positions in cycloartanes from nature.