ABSTRACT Geopropolis is a special type of propolis produced by stingless bees. Several pharmacological properties have been described for different types of geopropolis, but there have been no previous studies of the geopropolis from Melipona mondury. In this study, we investigated the antioxidant, antibacterial, and antiproliferative activities of M. mondury geopropolis, and determined its chemical profile. The antioxidant activity was determined using in vitro ABTS·+, ·DPPH, and β-carotene/linoleic acid co-oxidation methods. The antibacterial activity was determined using a microdilution method with Pseudomonas aeruginosa, Staphylococcus aureus, and methicillin-resistant S. aureus. The antiproliferative effect was determined in tumor cell lines using the Alamar Blue assay. The chemical profile was obtained using UHPLC-MS and UHPLC-MS/MS. The butanolic fraction had the highest concentration of phenolic compounds and more potent antioxidant properties in all assays. This fraction also had bacteriostatic and bactericidal effects against all bacterial strains at low concentrations, especially S. aureus. The hexane fraction had the highest antiproliferative potential, with IC50 values ranging from 24.2 to 46.6 µg/mL in HL-60 (human promyelocytic leukemia cell) and K562 (human chronic myelocytic leukemia cell), respectively. Preliminary chemical analysis indicates the presence of terpenes and gallic acid in the geopropolis. Our results indicate the therapeutic potential of geopropolis from M. mondury against inflammatory, oxidative, infectious, and neoplastic diseases.

This manuscript describes an update review with up to 285 references concerning the occurrence of amides from a variety of species of the genus Piper (Piperaceae). Besides addressing occurrence, this review also describes the biological activities attributed to extracts and pure compounds, a compiled 13C NMR data set, the main correlations between structural and NMR spectroscopic data of these compounds, and employment of hyphened techniques such as LC-MS, GC-MS and NMR for analysis of amides from biological samples and crude Piper extracts.

Este trabalho descreve a composição química e a atividade antimicrobiana dos óleos voláteis de Ocimum canum e Ocimum selloi, que ocorrem em Jequié/BA, nordeste do Brasil. As plantas foram colhidas no inverno de 2005 e verão de 2006 e os óleos extraídos por destilação a vapor foram posteriormente analisados por GC-MS. Um total de 30 e 31 compostos foi identificado a partir dos óleos de O. selloi e O. canum, respectivamente. Foi observado que o teor de óleo de O. canum apresentou variação durante as estações do ano, enquanto o óleo de O. selloi não. Metilchavicol e linalol foram os principais componentes químicos encontrados na parte aérea e folhas de O. canum. Esta descoberta permitiu caracterizar este espécime como um novo quimiotipo de O. canum. Com relação às partes aéreas de O. selloi, eugenol, 1,8-cineol, trans-cariofileno e linalol foram identificadas como os seus principais componentes. Todos os óleos extraídos das partes aéreas apresentaram atividade biológica contra cocos gram-positivo - Staphylococcus aureus ATCC 25923 - mas apenas aquele de O. canum apresentou atividade contra bacilo gram-negativo - Escherichia coli ATCC 25922.

This work describes the chemical composition and antimicrobial activity of the volatile oils of Ocimum canum and Ocimum selloi, both occurring in Jequié/BA, northeastern Brazil. The plants were collected in the winter/2005 andsummer/2006, the oils extracted by steam distillation and further analyzed by GC-MS. A total of 30 and 31 compounds was identified from the oils of O. selloi and O. canum, respectively. It was observed that the oil content of O. canum showed variation during the seasons, while the oils of O. selloi did not. Methylchavicol and linalool were the main chemical components found in the aerial parts and leaves of O. canum. This finding permitted to characterize this specimen as a new chemotype of O. canum. Regarding the aerial parts of O. selloi, eugenol, 1,8-cineole, transcaryophyllene and linalool were identified as their major components. All extracted oils from the aerial parts showed biological activity against gram-positive cocci - Staphylococcus aureus ATCC 25923 - but only the O. canum one showed activity against gram-negative bacilli - Escherichia coli ATCC 25922.

Aquatidial, um novo bis-norsesquiterpenóide assimétrico, hipoteticamente derivado da isoemigossipolona, foi isolado da casca externa das raízes de Pachira aquatica (Bombacaceae), juntamente com os compostos conhecidos isoemigossipolona, p-cumarato de triacontila e lupeol. As estruturas do aquatidial e dos demais compostos foram determinadas por análises espectroscópicas (EM-FAB, IV, RMN 1D e 2D) ou por comparação com dados publicados na literatura.

Aquatidial, a new asymmetric bis-norsesquiterpenoid, hypothetically derived from isohemigossypolone, was isolated from the outer bark of Pachira aquatica (Bombacaceae) roots, along with the known compounds isohemigossypolone, triacontyl p-coumarate and lupeol. The structures of aquatidial and the known compounds were established by spectroscopic analyses (HRFABMS, IR, 1D and 2D NMR) or comparison with published data from literature.

The chemical study of the barks of the stem and roots of Bombacopsis glabra (Bombacaceae) led to the isolation and identification of 5-hydroxy-3,7,4'-trimethoxyflavone (1), 5-hydroxy-3,6,7,4'-tetramethoxyflavone (2), the naphtoquinone isohemigossypolone (3), the ester triacontil p-coumarate (4) besides lupeol and a mixture of beta-sitosterol and stigmasterol. Their structures were elucidated by spectroscopic analysis, including IR, ¹H and 13C NMR and MS. All these compounds, except 3, were isolated for the first time in the family.

The first chemical study of non-volatile constituents from the bark and stem of Melaleuca alternifolia (Myrtaceae) led to the isolation and identification of 3,3'-O-dimethylellagic acid (1) and five pentacyclic triterpenes: 2alpha,3beta,23-trihydroxyolean-12-en-28-oic acid (arjunolic acid, 2), 3beta-hydroxylup-20(29)-en-27,28-dioic acid (melaleucic acid, 3), betulinic acid (4), betuline (5), 3beta-O-acetylurs-12-en-28-oic acid (6), a mixture of fatty acids and esters, and several hydrocarbons. For 2alpha,3beta,23-trihydroxyolean-12-en-28-oic acid (2) and 3beta-O-acetylurs-12-en-28-oic acid (6) a first detailed assignment of ¹H NMR is presented.

Do extrato hexânico da casca do caule de Bombacopsis glabra (Bombacaceae) foram isolados a flavona 5-hidroxi-3,6,7,8,4'-pentametoxiflavona (1) e os triterpenos lupenona, 9,19-ciclolanost-23-eno-3beta,25-diol (2), (24R)-9,19-ciclolanost-25-eno-3beta,24-diol (3) e (24S)-9,19-ciclolanost-25-eno-3beta,24-diol (4). As estruturas foram determinadas por espectroscopia de RMN de 13C e de ¹H (1D e 2D) e EM, e ainda, por comparação com dados da literatura para os triterpenos. A confirmação inequívoca da estrutura da flavona 1 foi realizada por um estudo de difração de raios X. As cinco substâncias foram isoladas pela primeira vez de espécies de Bombacaceae.

The flavone 5-hydroxy-3,6,7,8,4'-pentamethoxyflavone (1) and the triterpenes lupenone, 9,19-cyclolanost-23-ene-3beta,25-diol (2), (24R)-9,19-cyclolanost-25-ene-3beta,24-diol (3) and (24S)-9,19-cyclolanost-25-ene-3beta,24-diol (4) were isolated from the hexane extract of the stem bark of Bombacopsis glabra (Bombacaceae). The structures were determined by 13C and ¹H NMR (1D and 2D) and mass spectrometry, and by comparison with literature data for triterpenes. The structure of the flavone 1 was unambiguously confirmed by a X-ray diffraction study. The five substances were isolated for the first time from Bombacaceae species.

The Bombacaceae family consists of 28 genera and 200 species. This work reviews all the chemical studies carried out on the members of this family, and shows that only ten genera were investigated. From this review it can be seen that no particular class of chemical metabolites is ubiquitous in this family.