The main objective of this work was to develop a nanoemulsion based on linseed oil and betulinic acid, stabilized with Pluronic F127 and polyglycerol polyricinoleate, for anticancer applications. The nanoemulsions were synthesized by ultrasound and evaluated for in vitro cytotoxicity, particle size, polydispersity index, zeta potential, morphology, encapsulation efficiency, storage stability, rheology and in vitro release kinetics. In vitro cytotoxicity assays were performed by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay (72 h) against HCT-116 (colorectal carcinoma), SNB-19 (glioblastoma), NCI-H460 (lung carcinoma) and L-929 (normal fibroblasts) cells. The determination of 50% inhibitory concentration (IC50) showed an increased selectivity for the emulsified betulinic acid when compared to its free form for the HCT-116 cells. The IC50 values for the synthesized nanoemulsions showed a range from 3.2 to 3.7 µM (HCT-116), 5.6 and 11.5 µM (NCI-H460), 5.8 and 7.3 µM (SNB-19) and > 16.5 µM for normal fibroblasts. In the 48 h in vitro release assays, it presented controlled release explained by the Korsmeyer-Peppas model, releasing 572.25 and 619.95 µg of betulinic acid in a controlled way, generating promising perspectives for the prolonged release of betulinic acid in anticancer applications.

The non-commercial copolymers E45S8, E45S17 and their mixtures with Pluronic® P123 (E21P67E21) were studied as carriers of the model drug griseofulvin. Critical micelle concentration (cmc) (dye solubilisation method), drug solubilisation capacity (Scp and Sh) determined by ultraviolet-visible (UV-Vis) spectroscopy and 1H nuclear magnetic resonance (1H NMR) and cytotoxicity (LDH activity in human neutrophils) were studied. E45S17 1.0 wt.% dispersions presented colloidal aggregates limiting its Scp in comparison to E45S8, but in 0.1 wt.% solutions this phenomenon seemed to be absent and E45S17 presented a higher Scp. The mixtures that showed the best Scp results contained 50% of P123 and presented low cmc. An evaluation of literature data suggested a minimum Em content of 62% in EmSn copolymers below which the increase of Sn length does not lead to an increase of Sh. The results suggested no toxicity of the copolymers on human neutrophils, supporting the use of P123 and poly(styrene oxide) containing copolymers as drug carriers.

A new sesquiterpene and twelve known compounds comprising eight flavonoids and four terpenoids, were isolated from the leaves, stems, roots and exudate of Croton muscicarpa Müll. Arg.. Their structures were identified as the terpenoids 6α-methoxy-cyperene, dammaradienol, squalene, acetyl aleuritolic acid and spathulenol, and as the flavonoids retusin, 3,7,4'-trimethoxy kaempferol, ombuine, pachipodol, kaempferol, casticin, 5-hydroxy-3,6,7,4'-tetramethoxyflavone and artemetin. All isolated compounds were characterized based on IR, MS, ¹H and 13C NMR, including 2D analyses (COSY, HSQC, HMBC, NOESY) and comparison with data from the literature.

Dois novos flavonoides, 3,4,10-tri-hidróxi-9-metoxi-pterocarpano and 2',4'-di-hidróxi-4'-metoxi-β-hidroxichalcanonol, foram isolados a partir de Platymiscium floribundum, em adição a homopterocapina, 2',4',4-tri-hidroxichalcona, 7,3',5'-tri-hidroxiflavanona, 7,3'-di-hidróxi-8,5'-di-metoxiisoflavanona, 8-hidróxi-5,6,7-tri-metoxicumarina, 6-hidróxi-7,8-di-metoxicumarina, 6,7,8-tri-metoxicumarina, 6,7-di-metoxicumarina, 8-hidróxi-6,7-di-metoxicumarina, 3β-acetóxi-28-hidróxi-olean-12-eno, 1,2,3-tri-metoxi-5-alilbenzeno, 3,4-di-metoxicinamaldeído, e β-sitosterol e estigmasterol como mistura. A caracterização estrutural de todos os compostos foi estabelecida com base em métodos espectroscópicos, particularmente ressonância magnética nuclear (RMN) 1D e 2D e comparação com dados da literatura.

Two new flavonoids, 3,4,10-trihydroxy-9-methoxypterocarpan and 2',4'-dihydroxy-4-methoxy-b-hydroxychacanonol, were isolated from Platymiscium floribundum, in addition to the homopterocarpin, 2',4',4-trihydroxychalcone, 7,3',5'-trihydroxyflavanone, 7,3'-dihydroxy-8,5'-dimethoxyisoflavanone, 8-hydroxy-5,6,7,-trimethoxycoumarin, 6-hydroxy-7,8-dimethoxycoumarin, 6,7,8-trimethoxycoumarin, 6,7-dimethoxycoumarin, 8-hydroxy-6,7-dimethoxycoumarin, 3β-acetoxy-28-hydroxyolean-12-ene, 1,2,3-trimethoxy-5-allyl-benzene, 3,4-dimethoxycinnamaldehyde, and β-sitosterol and stigmasterol as a mixture. Structural characterization of all compounds was established on the basis of spectroscopic methods, particularly 1D and 2D nuclear magnetic resonance (NMR) and comparison with data from literature.

O estudo fitoquímico do extrato etanólico das folhas de Moringa oleifera Lam., Moringaceae, resultou no isolamento dos derivados benzilnitrilas niazirina, niazirinina e 4-hidroxifenil-acetonitrila, enquanto que das cascas dos frutos somente o octacosano foi obtido. Os óleos essenciais das folhas, flores e frutos foram analisados por cromatografia gasosa acoplada a espectrometria de massa. Os constituintes principais identificados foram: fitol (21,6%) e timol (9,6%) nas folhas, octadecano (27,4%) e ácido hexadecanóico (18,4%) nas flores e docosano (32,7%) e tetracosano (24,0%) nos frutos. As estruturas dos compostos isolados foram identificadas a partir de técnicas espectroscópicas (RMN, IV e EM). A 4-hidroxifenil-acetonitrila está sendo citada pela primeira vez para o gênero Moringa e os óleos essenciais das flores e frutos estão sendo citados pela primeira vez para a espécie M. oleifera.

Phytochemical analysis of the ethanol extract from leaves of Moringa oleifera Lam., Moringaceae, yield the benzylnitriles: niazirine, niazirinine and 4-hydroxyphenylacetonitrile, while of fruit shells only octacosane was isolated. The essential oils from leaves, flowers and fruits were examined by gas chromatography-mass spectrometry. The major constituents identified were: phytol (21.6%) and thymol (9.6%) in the leaves oil, octadecane (27.4%) and hexadecanoic acid (18.4%) in the flowers oil, docosane (32.7%) and tetracosane (24.0%) in the fruits oil. The structures of all compounds were identified by spectroscopic analyses (NMR, IR and MS). 4-hydroxyphenylacetonitrile is reported for the first time to the Moringa genus and the essential oils of flowers and fruits are reported for the first time to the species M. oleifera.