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Recebido em 15/1/08, aceito em 17/3/08, publicado na web em 23/4/08 CHEMICAL CONSTITUENTS OF THE FLOWERS OF Pterogyne nitens (CAESALPINIOIDEAE). The phytochemical investigation of the flowers of Pterogyne nitens (Caesalpinioideae) resulted in the isolation and identification of nine phenolic derivatives, quercetin 3-O-sophoroside, taxifolin, astilbin, ourateacatechin, caffeic, ferulic, sinapic, chlorogenic and gallic acid, besides two guanidine alkaloids, pterogynine, pterogynidine. This is the first time these compounds have been reported in P. nitens flowers. As this is a monospecific genus, these secondary metabolites may have taxonomical significance. Their structures were assigned on the basis of spectroscopic analyses, including two-dimensional NMR techniques.

As part of our ongoing bioprospecting studies on secondary metabolites in plants of Cerrado and Atlantic Rain Forest of São Paulo State (Brazil), we describe the identification of triterpenes and sterols present in the hexane extracts and foliar epicuticular wax of Pterogyne nitens Tulasne (Fabaceae-Caesalpinioideae) using high resolution gas chromatography. Compounds detected in these extracts include β-amyrin (1), taraxerol acetate (2), lupenone (3), β-amyrenone (4), germanicone (5), campesterol (6), stigmasterol (7), and β-sitosterol (8). The method reported herein is shown to be a rapid, sensitive and reproducible tool for describing triterpenes and sterols present in non-polar extracts.

The cyclopenta[b]indole motif is present in several natural and synthetic biologically active compounds, being directly responsible for the biological effects some of them present. We described herein a three step sequence for the synthesis of cyclopenta[b]indoles with a great structural diversity. The method is based on an oxidative Michael addition of suitable indoles on the double bond of Morita-Baylis-Hillman adducts mediated by a hypervalent iodine reagent (IBX) to form β-ketoesters, which were chemoselectively reduced with NaBH4 in THF to give the corresponding β-hydroxy-esters. The diastereoisomeric mixture was then treated with a catalytic amount of triflic acid (20 mol %) to give cyclopenta[b]indoles with overall yields ranging from 8 to 73% (for 2 steps). The acid-catalyzed cyclization step gave the required heterocycles, via an intramolecular Friedel-Crafts reaction, with high diastereoselectivity, where only the trans product was observed. A mechanistic study monitored by ESI-(+)-MS was also conducted to collect evidence about the mechanism of this reaction. The new molecules herein synthesized were also evaluated against a panel of human cancer cells demonstrating a promising antitumoral profile.

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