Gelatine/PVA copolymer film incorporated with quercetin as a prototype to active antioxidant packaging.

Films that incorporate antioxidant agents are widely used and improve the stability of food products that are prone to oxidation. This work evaluated the potential antioxidant activity of PVA/gelatine films incorporated with quercetin. The films were prepared by the casting method and characterised by TG-DSC, FTIR spectroscopy, SEM, optical microscopy and swelling index. Antioxidant properties were evaluated with DPPH, ABTS and FRAP assays. According to the thermal characterisation results, the film was stable up to 68 °C and entirely degraded at 632 °C. The FTIR spectroscopic analysis indicated that there was a physical interaction between the quercetin and the polymeric film, and microscopy indicated a homogeneous and uniform film. The film showed DPPH (315.4 ± 8.2) and ABTS radical potential activity (199.4 ± 9.7), as well as potential iron reduction activity-FRAP (740.6 ± 8.9) mainly when analysed in ethanol: water (95:5 v/v) system, all results expressed as milligram of Trolox per gram of film. Hence, PVA/gelatine films incorporated with quercetin have properties that allow a potential application in active packaging systems to delay oxidative processes in food.

Desenvolvimento e caracterização de filme biodegradável inteligente à base de amido de banana verde e extrato de brassica oleraceae (repolho roxo) / Development and characterization of green biodegradable film based on green banana starch and brassica oleraceae extract (purple cabbage)

O objetivo deste estudo foi desenvolver e caracterizar filme indicador de qualidade de alimentos utilizando amido de banana verde incorporado com extrato de repolho roxo. Os filmes foram desenvolvidos a partir de duas formulações: i) amido de banana sem extrato; ii) amido de banana com extrato. Os filmes foram caracterizados através de análise térmica (TG/DT), ensaio mecânico, espectroscopia por infravermelho (FT-IR), índice de intumescimento e ativação em diferentes pH. Os filmes apresentaram um perfil similar de perda de massa, indicando pouco efeito da incorporação do extrato à sua estabilidade térmica. A incorporação do extrato vegetal promoveu maior resistência mecânica e menor taxa de intumescimento. FT-IR mostrou que não houve interação do extrato com o biopolímero. O filme de amido apresentou sensibilidade à variação do pH. O uso do amido de banana verde combinado com gelatina e extrato de repolho roxo apresenta potencial aplicação como indicador visual de qualidade de alimentos duranteo armazenamento.

The aim of the study was to develop and characterize food quality indicator film using green banana starch incorporated with purple cabbage extract. The films were developed from two formulations: i) banana starch without extract; ii) banana starch with extract. The films were characterized by thermal analysis (TG/DTA), mechanical assay, infrared spectroscopy (FT-IR), swelling index and activation at different pH. The films presented a similar profile of mass loss, indicating that extract did not affect thermal stability. The incorporation of the vegetal extract promoted greater mechanical resistance and a lower rate of swelling. FT-IR showed that there was no interaction of the extract with the biopolymer. The starch film showed sensitivity to pH variation. The use of green banana starch combined with gelatin and purple cabbage extract has potential application as a visual indicator of food quality during storage.

Differentiation between 3,4- and 4,15-Epoxyeudesmanolides by Electrospray Ionization Tandem Mass Spectrometry.

We investigated the fragmentation of the eudesmanolide-type sesquiterpene lactones 1α-(4-hydroxymethacryloyloxy)-3α,4α-epoxy-8α-hydroxyeudesm-11(13)-6α,12-olide (1) and 1α-(2,3-epoxyangeloyloxy)-4α,15-epoxy-8α-hydroxyeudesm-11(13)-6α,12-olide (2) by electrospray ionization tandem mass spectrometry (ESI-MS/MS). The elimination of the different ester substituent at C(1) directly from protonated 1 and 2 (A) led to the formation of two regioisomer product ions B (A - RCO2H). Further fragmentation of B resulted from consecutive eliminations of H2O and CO molecules. However, we identified four product ions that allowed for the differentiation between 3,4- and 4,15-epoxyeudesmanolides. The formation of these diagnostic ions was associated with the C(3)-O bond of compound 1, which propitiates the participation of the lone pair of the oxygen epoxide in the formation of B through a Grob-Wharton-type fragmentation, then resulting in an alternative fragmentation pathway. These data can be useful for the fast differentiation between epoxyeudesmanolide regioisomers directly from Dimerostemma extracts by liquid chromatography-tandem mass spectrometry (LC-MS/MS), as an alternative to NMR, or even for quantitation studies of these compounds using multiple reaction monitoring (MRM) scan.

Schistosomicidal Effects of the Essential Oils of Citrus limonia and Citrus reticulata Against Schistosoma mansoni.

We report the in vitro schistosomicidal effects of the essential oil obtained from Citrus limonia leaves (CL-EO) and C. reticulata fruit peels (CR-EO), cultivated in Brazil, against Schistosoma mansoni worms. Limonene (29.9%), ß-pinene (12.0%), sabinene (9.0%), citronellal (9.0%), and citronellol (5.8%) are the major constituents of CL-EO; limonene (26.5%), γ-terpinene (17.2%), linalool (11.1%), octanal (8.0%), myrcene (6.2%), and capraldehyde (3.9%) predominate in CR-EO. CL-EO displayed moderate lethal concentration 50% (LC50 ) of 81.7 and 38.9 µg/ml against male and female worms at 24 and 72 h, respectively. At concentrations of 25 and 100 µg/ml, CL-EO separated between 50 and 75% of the coupled worm pairs during the evaluated period. CR-EO presented moderate LC50 of 81.7 µg/ml against male and female worms at 24 and 72 h. However, this oil separated coupled worm pairs more effectively than CL-EO and displayed lower cytotoxicity to GM07492-A cells (IC50 = 987.7 ± 88.9 µg/ml) as compared to CL-EO (IC50 = 187.8 ± 2.9 µg/ml). The enantiomers (+)-(R)-limonene and (-)-(S)-limonene did not affect S. mansoni adult worm pairs significantly. Taken together, these data indicate that CL-EO and CR-EO exhibit moderate in vitro schistosomicidal activity against adult S. mansoni worms.

Antifungal activity of plant-derived essential oils on Candida tropicalis planktonic and biofilms cells.

Dental prosthesis supports Candida species growth and may predispose the oral cavity to lesions. C. tropicalis has emerged as a colonizer of prosthesis and has shown resistance to clinically used antifungal agents, which has increased the search for new antifungals. This work describes the effectiveness of fifteen essential oils (EOs) against C. tropicalis The EOs were obtained by hydrodistillation and were chemically characterized by gas chromatography-mass spectrometry. The antifungal activities of the EOs were evaluated by the microdilution method and showed that Pelargonium graveolens (Geraniaceae) (PG-EO) was the most effective oil. Geraniol and linalool were the major constituents of PG-EO. The 2,3-Bis-(2-Methoxy-4-Nitro-5-Sulfophenyl)-2H-Tetrazolium-5-Carboxanilide (XTT) assay showed that all the clinical C. tropicalis strains formed viable biofilms. Scanning electron microscopy examination of the biofilms revealed a complex architecture with basal layer of yeast cells and an upper layer of filamentous cells. Treatments with PG-EO, linalool, and geraniol significantly reduced the number of viable biofilm cells and inhibited biofilm formation after exposure for 48 h. PG-EO, geraniol, and linalool were not toxic to normal human lung fibroblasts (GM07492A) at the concentrations they were active against C. tropicalis Together, our results indicated that C. tropicalis is susceptible to treatment with PG-EO, geraniol, and linalool, which could become options to prevent or treat this infection.

Self-organizing maps of molecular descriptors for sesquiterpene lactones and their application to the chemotaxonomy of the Asteraceae family.

The Asteraceae, one of the largest families among angiosperms, is chemically characterised by the production of sesquiterpene lactones (SLs). A total of 1,111 SLs, which were extracted from 658 species, 161 genera, 63 subtribes and 15 tribes of Asteraceae, were represented and registered in two dimensions in the SISTEMATX, an in-house software system, and were associated with their botanical sources. The respective 11 block of descriptors: Constitutional, Functional groups, BCUT, Atom-centred, 2D autocorrelations, Topological, Geometrical, RDF, 3D-MoRSE, GETAWAY and WHIM were used as input data to separate the botanical occurrences through self-organising maps. Maps that were generated with each descriptor divided the Asteraceae tribes, with total index values between 66.7% and 83.6%. The analysis of the results shows evident similarities among the Heliantheae, Helenieae and Eupatorieae tribes as well as between the Anthemideae and Inuleae tribes. Those observations are in agreement with systematic classifications that were proposed by Bremer, which use mainly morphological and molecular data, therefore chemical markers partially corroborate with these classifications. The results demonstrate that the atom-centred and RDF descriptors can be used as a tool for taxonomic classification in low hierarchical levels, such as tribes. Descriptors obtained through fragments or by the two-dimensional representation of the SL structures were sufficient to obtain significant results, and better results were not achieved by using descriptors derived from three-dimensional representations of SLs. Such models based on physico-chemical properties can project new design SLs, similar structures from literature or even unreported structures in two-dimensional chemical space. Therefore, the generated SOMs can predict the most probable tribe where a biologically active molecule can be found according Bremer classification.

Eudesmanolides and methyl ester derivatives from Dimerostemma arnottii.

The phytochemical investigation of Dimerostemma arnottii (Asteraceae) afforded, in addition to a known eudesmanolide, two unusual eudesmane methyl ester derivatives and a new eudesmanolide. Structural elucidation of the compounds was based on their 1D and 2D NMR spectroscopic as well as HR-ESI-MS data. There is a remarkable similarity between the structures of the eudesmanes from D. arnottii and those previously encountered in other Dimerostemma species, which is in agreement with the results of a previous phylogenetic study based on molecular data. The chemotaxonomic relevance of the isolated compounds is briefly discussed.

Sesquiterpene lactones from Dimerostemma species (Asteraceae) and in vitro potential anti-inflammatory activities.

Two Brazilian species of Dimerostemma (Asteraceae) were chemically investigated. Two known sesquiterpene lactones (STLs), a germacrolide and an eudesmanolide, were isolated from D. episcopale while D. brasilianum afforded the new germacranolide 1beta,5beta/10alpha-trihy-droxy-8alpha-angeloyloxy-germacra-3,11(13)-dien-6alpha,12-olide in addition to a known one. Structure identification based on NMR and MS analyses. 1beta,10alpha,4alpha,5beta-Diepoxy-8alpha-angeloyloxy-costunolide isolated from D. brasilianum was studied for its anti-inflammatory activity. This STL completely inhibited DNA binding of the transcription factor NF-kappaB at a concentration of 5 microm and 10 microM in Jurkat T and Raw 264.7 cells, respectively. Elastase release from human neutrophils was reduced to 50% at a concentrations of 23 microM after stimulation with PAF and of 27 microM after stimulation with fMLP without showing cytotoxic effects. Additionally, elastase was also directly inhibited.

Automatic identification of terpenoid skeletons by feed-forward neural networks.

Feed-forward neural networks (FFNNs) were used to predict the skeletal type of molecules belonging to six classes of terpenoids. A database that contains the 13C NMR spectra of about 5000 compounds was used to train the FFNNs. An efficient representation of the spectra was designed and the constitution of the best FFNN input vector format resorted from an heuristic approach. The latter was derived from general considerations on terpenoid structures.

Eudesmanolides from Dimerostemma vestitum.

A leaf rinse extract with dichloromethane from Dimerostemma vestitum afforded five new eudesmanolides (1-5) along with the known flavone eupafolin. Compounds 1-5 were isolated by chromatographic methods, and their structures were elucidated by spectral analyses. Eudesmanolides 1-4 show a functional group substitution pattern so far unreported in the subtribe Verbesininae (tribe Heliantheae) of the family Asteraceae.