Copaiba oil-resin has aromatic characteristics and pharmacological activities attributed to sesquiterpenes compounds. These purified compounds present application in perfume, pharmaceutical and cosmetic industries. Therefore, the objective of this work was to use molecular distillation to recover and purify sesquiterpenes of the copaiba oil-resin with purity high. The parameters evaporator temperature (TEV) from 45 to 100 ºC and feed flow rate (Q) between 15 and 30 ml min-1 were evaluated through design of experiments (22 with center points). The results showed that it was possible to recover sesquiterpenes with 98.12% purity in the distillate stream. Increased in TEV and reduction in Q were the effects observed experimentally and through the response surface. The best experimental condition was TEV of 100 °C and Q of 15 mL min-1. Collor differences were noticed between distillate streams (colorless) and residue (brown). These can be used as parameters for separation of sesquiterpenes and diterpenes. The molecular distillation proved to be an efficient processo to both recovery and purification of sesquiterpenes from the copaiba oil-resin.

As sementes de Pterodon pubescens Benth. (Pp), disponíveis comercialmente no Brasil, são utilizadas na medicina popular em preparações anti-inflamatórias, analgésicas e anti-reumáticas. O presente estudo demonstrou as propriedades antinociceptivas da mistura de isômeros 6α-hidroxi-7β-acetoxi-vouacapano-17β-oato de metila e 6α-acetoxi-7β-hidroxi-vouacapano-17β-oato de metila (C1) isolada de Pp, empregando modelos experimentais diferentes. Um estudo de estabilidade foi realizado para investigar a relação da microencapsulação por "spray-drying" na manutenção do efeito antinociceptivo. Para isso, amostras de C1 e extrato de Pp foram monitorados no estudo de estabilidade acelerada, avaliando tanto amostras microencapsuladas como não microencapsuladas. Foi observado que a amostra C1 possui atividade antinociceptiva, revelada pelos ensaios das contorções abdominais e de formalina; foi observada também atividade significativa antialodínica, mas não efeito anti-hiperalgésico. A microencapsulação manteve a atividade e integridade de C1 e do extrato bruto de Pp, demonstrando que a microencapsulação por "spray drying" é uma alternativa útil para aumentar o tempo de prateleira.

Pterodon pubescens Benth. (Pp) seeds, commercially available in Brazil, are used in folk medicine in anti-inflammatory, analgesic, and anti-rheumatic preparations. The present study demonstrated the antinociceptive properties of isomers 6α-hydroxy-7β-acetoxy-vouacapan-17β-oate methyl ester and 6α-acetoxy-7β-hydroxy-vouacapan-17β-oate methyl ester (C1), isolated from (Pp), employing different experimental models. A stability study was performed to investigate the relationship of microencapsulation by spray-drying on the maintenance of antinociceptive action. Therefore, C1 and Pp extract samples were monitored in accelerated stability study, evaluating both microencapsulated and non-microencapsulated samples. It was observed that sample C1 possess antinociceptive activity revealed by writhing and formalin tests; C1 showed significantly anti-allodynic, but not antihyperalgesic effect; the microencapsulation maintained the activity and integrity of both, sample C1 and Pp crude extract; microencapsulation by spray drying is a useful alternative to increase shelf life.

O fracionamento biomonitorado do extrato diclorometânico das sementes de Pterodon pubescens Benth forneceu o 6α-acetóxi-7β-hidróxi-vouacapano 1 (inédito), além de quatro diterpenos furânicos (2, 3, 4 e 5). A atividade antiproliferativa dos compostos foi avaliada in vitro contra as linhagens de células tumorais humanas UACC-62 (melanoma), MCF-7 (mama), NCI-H460 (pulmão), OVCAR-03 (ovário), PC-3 (próstata), HT-29 (colon), 786-0 (rim), K562 (leucemia) e NCI-ADR/RES (ovário com fenótipo de resistência a múltiplos fármacos). Os resultados foram expressos em três concentrações efetivas GI50 (concentração para que ocorra 50% de inibição de crescimento), TGI (concentração que resulta em inibição total de crescimento) e LC50 (concentração que resulta em 50% de morte celular). A citotoxicidade in vitro foi avaliada também frente a uma linhagem de célula murina normal (3T3). Este é o primeiro relato de atividade anticâncer para os compostos 1, 4 e 5, que apresentaram grande seletividade, dependente da concentração, para PC-3. O composto 1 foi 26 vezes mais potente para inibir 50% do crescimento (GI50) de PC-3, 15 vezes mais citostático (TGI) e 6 vezes menos tóxico (LC50) quando comparado com Doxorrubicina (controle).

Activity guided fractionation of Pterodon pubescens Benth. methylene chloride-soluble fraction afforded novel 6α-acetoxi 7β-hydroxy-vouacapan 1 and four known diterpene furans 2, 3, 4, 5. The compounds were evaluated for in vitro cytotoxic activities against human normal cells and tumour cell lines UACC-62 (melanoma), MCF-7 (breast), NCI-H460 (lung, non-small cells), OVCAR-03 (ovarian), PC-3 (prostate), HT-29 (colon), 786-0 (renal), K562 (leukemia) and NCI-ADR/RES (ovarian expressing phenotype multiple drugs resistance). Results were expressed by three concentration dependent parameters GI50 (concentration that produces 50% growth inhibition), TGI (concentration that produces total growth inhibition or cytostatic effect) and LC50 (concentration that produces -50% growth, a cytotoxicity parameter). Also, in vitro cytotoxicity was evaluated against 3T3 cell line (mouse embryonic fibroblasts). Antiproliferative properties of compounds 1, 4 and 5 are herein reported for the first time. These compounds showed selectivity in a concentration-dependent way against human PC-3. Compound 1 demonstrated selectivity 26 fold more potent than the positive control, doxorubicin, for PC-3 (prostrate) cell line based on GI50 values, causing cytostatic effect (TGI value) at a concentration fifteen times less than positive control. Moreover comparison of 50% lethal concentration (LC50 value) with positive control (doxorubicin) suggested that compound 1 was less toxic.