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INTRODUCTION: Phytochemical and biological studies carried out on Copaifera species showed that their oleoresins and isolated compounds have various biological activities. OBJECTIVE: The aims of this work were (i) to analyse the Copaifera oleoresin by gas chromatography-mass spectrometry, (ii) to isolate the diterpenic acids from this oleoresin by high-speed countercurrent chromatography (HSCCC) and (iii) to determine the rhodamine 6G Pdr5p activity of these acids. METHODOLOGY: HSCCC was used for the preparative separation of the diterpenes. Spectroscopic methods were used to establish their identity. RESULTS: The gas chromatogram of the oleoresin showed approximately 30 compounds. The two major ones, kaur-16-en-18-oic and polyalthic acids, were isolated in high purity. Kaur-16-en-18-oic acid exhibited the highest rodomine 6G Pdr5p activity among the tested compounds. CONCLUSION: HSCCC was shown to be a quick and effective tool in the isolation and purification of diterpenes from Copaifera oleoresin. This is the first report on the use of HSCCC for the fractionation of an oleoresin from Copaifera and the isolation of diterpenes therein.

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A simple method for the resolution and subsequent quantitative determination of liriodenine and moupinamide in Mollinedia species was developed using reversed-phase HPLC based on an octadecyl silane-packed column eluted with gradients of methanol and water.

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The isolation and NMR data of seco-lupane triterpenes and coumarins from Platypodium elegans are reported.

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The buffy-headed marmoset (Callithrix flaviceps) is apparently the only predispersal herbivore of the seeds of Siparuna guianensis at the Caratinga Biological Station in southeastern Brazil. Both the fruit receptacles and the frutioles (seeds) of S. guianensis are relatively rich in nutrients such as carbohydrates, proteins, and lipids, but the receptacles contain high concentrations of benzylisoquinoline alkaloids. The latter presumably act as a qualitative chemical defense, impeding the access of potential predators to the alkaloid-poor frutioles. However, on ripening, the receptacle splits open, exposing the frutioles, which enables C. flaviceps to avoid the plant's chemical defenses effectively. Taking care to avoid contact with the receptacle, the marmosets pluck out the frutioles and ingest the seeds. Qualitative and quantitative changes (in particular a significant reduction in daily ranging) in the marmosets' behavior during the period when S. guianensis frutioles were accessible indicate that this was a preferred plant resource. This is the first record of the consumption of S. guianensis seeds by callitrichine monkeys (which are not known to be systematic seed eaters), despite the fact that both are widely distributed in the Neotropics. It is thus possible that the behavioral strategy observed here is a unique phenomenon resulting from a specific combination of factors, including the abundance of S. guianensis within the study area. The lack of other records may nevertheless be a result of insufficient sampling effort, in which case, the feeding strategies of callitrichines may have an important influence on the reproductive biology of S. guianensis in many areas.

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Brazilian plant extracts belonging to 16 species of 5 different families (71 extracts) were tested against the stable DPPH (2,2-diphenyl-1-picryl-hydrazyl-hydrate) free-radical. The ability to scavenge DPPH radical was measured in these experiments by the discoloration of the solution. Ginkgo biloba and rutin, commonly used as antioxidants for medical purposes, were used as standards. Based on our results, we can say that as a general rule the ethanol extracts of plants belonging to the Verbenaceae family showed lower EC(50) values than the other plant extracts. Among the partitions, the more polar ones (ethyl acetate and n-butanol) are those that generally have higher antioxidant activity (AA).

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Foliar secretory cavities, commonly called leaf pellucid glands, have been reported in many families of vascular plants. In the Rubiaceae, these structures have only been found in the sister genera Rustia and Tresanthera, which are also anomalous within the family because they have poricidal anthers, and in the distantly related Heterophyllaea. General leaf anatomy, with particular attention to secretory cavities, as well as the chemical analysis of the secreted substances of Rustia formosa, is presented here for the first time. The secretory structures have been found in the lamina between the palisade and spongy parenchymas and in the cortical region of the petiole. The chemical analysis showed that the essential oil secreted is a complex mixture of at least 75 components, mostly of sesquiterpenoid composition. Illustrations of the leaf anatomy, details of the secretory structures of Rustia formosa, a gas chromatogram, and a table of the principal components of the leaf essential oil are included.

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The kaempferol derivative 3,7-di-O-methyl-4'-O-beta-[alpha rhamnosyl (1 --> 6)]-glucopyranoside (siparunoside) was isolated from the leaves of Sparuna apiosyce. Its structure was established by extensive NMR studies. The alkaloids reticuline and liriodenine were also isolated from the leaves along with the kaempferol derivative tiliroside. Benzylisoquinoline alkaloids were isolated from the wood (liriodenine) and wood bark (liriodenine, laurotetanine, N-methyl-laurotetanine, reticuline), together with a mixture of cis and trans-N-feruloyltyramines. 3,7,4'-tri-O-methylkaempferol was isolated from all organs.

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A butanolide, marliolide, was isolated from the hexane extract of leaves of Mollinedia marliae (Monimiacae) along with the long chain fatty alcohol hexacosanol. Phytol and a mixture of sitosterol and stigmasterol were also isolated from leaves of both M. marliae and M. gilgiana. trans-N-Feruloyltyramine, a ferulic acid derivative, is the major constituent of the stems of M. gilgiana.

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The chemistry and pharmacology of species of the family Monimiaceae are reviewed, with special attention given to the genera Mollinedia and Siparuna, the two most important and representative in Brazil. The isolation of benzylisoquinoline alkaloids and kaempferol derivatives from Siparuna apiosyce is reported, as well as the isolation of aporphines from the fruits of Siparuna arianeae. Cinnamic acid derivatives and a gamma-lactone were isolated from Mollinedia gilgiana and Mollinedia marliae.

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