Eugenia uniflora, popularly known as pitanga, is a native species of the Brazilian flora, widely used in folk medicine for the treatment of various diseases and which has several bioactive chemical constituents. The aim of this work was to analyze the chemical composition of flowers visited by bees from Eugenia uniflora by Ultra-Performance Liquid Chromatography coupled with a Diode Array Detector and quadrupole Time of Flight Mass Spectrometry (UPLC-DAD-qTOF-MS/MS). Forty-four compounds were tentatively identified, including quinic acid, seven tannins and thirty-six flavonoids.

ABSTRACT The Northeastern Brazil has xerical vegetation with different biomes. Its botanical heterogeneity represents shelter for diverse fauna. The region is rich in bees, which demand the resources offered by the plants, and provide pollination services. Bee pollen has been used as a beneficial food source for humans due to its high nutritional content and being a natural antioxidant. Pollen analysis can determine the plant species visited by bees, using them as the source of pollen supply. This study aimed to identify the main pollen types present in the pollen collected by Apis mellifera in the Northeastern Brazil and to define its botanical affinity. Commercial bee pollen samples produced in the region were treated by acetolysis method, mounted on slides, and the frequency of occurrence was estimated for each type of pollen. It was possible to distinguish 113 pollen types belonging to 35 botanical families, distributed in 92 genera. Fabaceae and Asteraceae were the families that most contributed to pollen types. Pollen types of Cocos nucifera and Myrcia were found in more than 50% of the samples. The families Arecaceae and Fabaceae showed high beekeeping potential. There is a striking similarity between the pollen samples from the states of Pernambuco and Rio Grande Norte.

RESUMO A abelha sem ferrão Melipona mandacaia (Smith 1863) (mandaçaia) é encontrada apenas na região da Caatinga, Nordeste do Brasil, nos estados da Bahia e Pernambuco, próximo ao rio São Francisco. O objetivo do presente trabalho foi determinar a origem botânica e avaliar o conteúdo fenólico e as propriedades antioxidantes (sistema β-caroteno / ácido linoléico, DPPH e sequestro do ABTS) da geopropolis da mandaçaia. Foram identificados 25 tipos polínicos de 15 famílias das 9 amostras de geoprópolis analisadas. O teor de compostos fenólicos variou entre todos os extratos etanólicos e as frações hexano, EtOAc e MeOH:H2O de geoprópolis. Os principais polens encontrados nas amostram de geopropolis foram da família Leguminoseae. Esta identificação de plantas utilizadas pelas meliponas indicam a importancia destas espécies vegetais como fontes de nectar e pólen. Nossos resultados revelaram que existe uma forte relação entre os compostos fenólicos e a atividade antioxidante. Estes resultados mostram que os fenóis totais da geoprópolis de mandaçaia foram responsáveis pela atividade antioxidante, com evidências de que é uma fonte rica de compostos bioativos fenólicos com potenciais benefícios a saúde.

ABSTRACT The stingless bee Melipona mandacaia (Smith 1863) (mandaçaia) is found only in the region of Caatinga, Northeastern Brazil, in the states of Bahia and Pernambuco, near to São Francisco river. The aim of the present work was to determine the botanical origin and to evaluate the phenolic content and antioxidant properties (β-carotene/linoleic acid system, DPPH and ABTS scavenging) of mandaçaia geopropolis. 25 pollen types from 15 families were identified from the 9 geopropolis samples analyzed. Phenolic compounds content varied between all the geopropolis EtOH extracts, hexane, EtOAc and MeOH:H2O fractions. The main pollens found in the geopropolis samples were from the Leguminoseae family. This identification of meliponicultural plants is extremely important because it indicates the food sources used for the collection of nectar and pollen. Our results revealed that there is a strong relation between the phenolic compounds and the antioxidant activity. These results showed that total phenols of mandaçaia geopropolis may be responsible for the antioxidant activity with evidence that it's a rich source of phenols bioactive compounds with potential health benefits.

ABSTRACT The geopropolis produced by the stingless bee Melipona subnitida (popularly called "jandaíra" in Brazil) is a mixture of resin, wax, and mud. This study analyzed the antifungal activity of the geopropolis extract from Candida spp., developed a gel formulation with this extract and analyzed the delivery of bioactives (kinetics release) in the formulation and their chemical profile by UHPLC-PDA-qTOF-MS/MS. Three different gels were prepared using the geopropolis extract, carbomer, propylene glycol, and water. Formulations with different amounts of propylene glycol were investigated. Physical, visual, pH, viscosity, adhesion, spreadability, leakage, and in vitro release tests were performed in the proposed formulations. Antifungal tests with the geopropolis ethanolic extract were carried out against six Candida species. The chemical profile of the geopropolis extract and compounds released from the formulations were analyzed after the release test. The formulations had a pH between 4.6 and 4.8 and viscosity between 535,600 and 920,400 cPs. The geopropolis extract presented excellent antifungal activity against the tested yeasts. The results of the release test in semipermeable cellulose membrane showed that all formulations containing 5%, 10% and 40% propylene glycol presented release of geopropolis extract. For adhesion and leakage tests, the gel formulation with 5% propylene glycol was more effective. Both geopropolis ethanolic extract and the liquid obtained in the release test showed the presence of flavonoids (flavonol/flavone, flavanone, and chalcones). Gel formulations with geopropolis extract that are rich in flavonoids are promising as an adjuvant treatment of vaginal candidiasis.

This work describes the biflavonoids found in species of Clusiaceae, particularly the genera Garcinia and Calophyllum, emphasizing the importance of these metabolites as chemical markers of this family, their contribution to the pharmacological potential of these species, besides the promising potential of these compounds in the search for new drugs.

Seven natural neolignans isolated from Licaria chrysophylla and Licaria aurea along with five semisynthetic derivatives were tested for their inhibitory action on DNA-topoisomerase by relaxation assays on pBR322 plasmid DNA. All compounds tested showed strong inhibition at a concentration of 100 µM, while none showed activity between 5 and 70 µM. These results indicate that no obvious correlation can be derived between the structure of these compounds and their inhibitory effect on the DNA relaxation activity of topoisomerase II. This is the first report on DNA topoisomerase II inhibitors from Licaria chrysophylla and Licaria aurea leading to the identification of lignoids as topoisomerase II-α inhibitors.

Our study reports the extraction and isolation of a new phaeophytin derivative 15¹-hydroxy-(15¹-S)-porphyrinolactone, designated anamariaine (1) herein, isolated from the chloroform fraction of aerial parts of Thyrsacanthus ramosissimus Moric. along with the known 15¹-ethoxy-(15¹-S)-porphyrinolactone (2). These compounds were identified by usual spectroscopic methods. Both compounds were subjected to in vitro (inhibitory activity) tests by means of supercoiled DNA relaxation techniques and were shown to display inhibitory activity against human DNA topoisomerase II-α at 50 µM. Interconversion of these two pigments under the mild conditions of the isolation techniques should be highly unlikely but cannot be entirely ruled out.

The phaeophorbide ethyl ester named Purpurin-18 and the flavonoids quercetin and kaempferol were obtained by chromatographic procedures from the chloroform fraction of aerial parts of Gossypium mustelinum. The structure of these compound was determined by NMR, IR and mass spectra data analysis. This is the first occurrence of this compound in Angiosperm.

The NMR (RMN¹H, 13C, COSY, HMQC, HMBC, NOE-DIFF, NOESY) and mass spectra data analysis of sixteen flavonoids, including nine natural, 7-O-methylkanferol (ramnocitrin), 3,7-di-O-methylkanferol (kumatakenin), 3-O-methylquercetin, 3,7,3',4'-tetra-O-methylquercetin (retusin), 3,7,8,4'-tetra-O-methylgossipetin, 3,7,8,3',4'-penta-O-methylgossipetin, 7-O-methylapigenin (genkwanin), 3,7,8-tri-O-methylherbacetin, 7,4'- di-O-methylquercetin (ombuine), isolated from Solanum paludosum and S. jabrense, and seven prepared methyl and acetyl derivatives, are discussed according the substitution on the rings A, B and C.

During the last decades several flavonoids of Solanum species have been isolated. This review describes the flavones, flavonols and their glycosides presently known as constituents of Solanum species.

RESUMO Afração contendo os alcalóides glicosilados totais dos frutos verdes de Solanum crinitum foi cromatografado em coluna de Sephadex e forneceu a solasonina, um alcalóide glicosilado cuja estrutura foi definida através da análise de dados espectrométricos no IV e de RMN de 1H e 13C. Os testes realizados com quatro repetições de cinco concentrações (0, 100, 200, 400 e 800 ppm) usando 25 sementes de alface (Lactuca sativa) permitiram verificar elevada atividade do extrato dos alcalóides glicosilados totais e da solasonina sobre a germinação e o desenvolvimento dessas plântulas, sendo a solasonina mais ativa. H 13C C 0, 0 (0 100 200 40 80 ppm 2 Lactuca sativa plântulas ativa ( 10 20 4 8 1

ABSTRACT The total glycoalkaloids fraction obtained from the unripe fruit of Solanum crinitum was chromatographed on sephadex LH-20 column to yield the solasonine, a glycoalkaloid which structure was identified by IR and NMR spectral data analysis. The allelopathic effect of the extract and solasonine on the seeds germination and lettuce seedlings development was detected. The tests were conduced with four replications of five concentration (0, 100, 200, 400, 800 ppm) using 25 seeds. Although both show high allelopathic activity. The solasonine was more effetive. LH20 LH 20 LH-2 analysis detected 0, 0 (0 100 200 400 80 ppm 2 activity effetive LH2 LH- ( 10 40 8 1 4

Phytochemical investigation of the aerial parts of S. paludosum afforded 3,4,7,8-tetramethyl gossypetinr, 3,7- dimethyl kaempferol, 3-methyl kaempferol, 3-methyl apigenin, and 3-methyl quercetin ethers, besides N-p-transcoumaroyltiramine, and protocatecuid acid. The structures were established from spectral data of the natural substances and the permethyl and acetyl derivatives of tetramethyl gossypetin.