Development of active bio-based multilayer systems: encapsulation of cinnamaldehyde and their physicochemical characterization

[Excerpt] In this work, different multilayer structures, using a polyhydroxybutyrate-co-valerate film with a valerate content of 8% (PHBV8) as support, were developed aiming the development of active bio-based multilayer systems. An interlayer based on zein nanofibers with and without cinnamaldehyde were electrospun in the PHBV8 film and three multilayer systems were developed: 1) without an outer layer; 2) using a PHBV8 film as outer layer; and 3) using an alginate-based film as outer layer. Their physico-chemical properties were evaluated through: water vapour and oxygen permeabilities and colour measurements, Fourier Transform Infrared Spectroscopy (FTIR) and thermal analyses. Results showed that the presence of different outer layers affected the water vapour permeability and transparency of the multilayer films. (...)

Anthelmintic activity of trans-cinnamaldehyde and A- and B-type proanthocyanidins derived from cinnamon (Cinnamomum verum)

Cinnamon (Cinnamomum verum) has been shown to have anti-inflammatory and antimicrobial properties, but effects on parasitic worms of the intestine have not been investigated. Here, extracts of cinnamon bark were shown to have potent in vitro anthelmintic properties against the swine nematode Ascaris suum. Analysis of the extract revealed high concentrations of proanthocyanidins (PAC) and trans-cinnamaldehyde (CA). The PAC were subjected to thiolysis and HPLC-MS analysis which demonstrated that they were exclusively procyanidins, had a mean degree of polymerization of 5.2 and 21% of their inter-flavan-3-ol links were A-type linkages. Purification of the PAC revealed that whilst they had activity against A. suum, most of the potency of the extract derived from CA. Trichuris suis and Oesophagostomum dentatum larvae were similarly susceptible to CA. To test whether CA could reduce A. suum infection in pigs in vivo, CA was administered daily in the diet or as a targeted, encapsulated dose. However, infection was not significantly reduced. It is proposed that the rapid absorption or metabolism of CA in vivo may prevent it from being present in sufficient concentrations in situ to exert efficacy. Therefore, further work should focus on whether formulation of CA can enhance its activity against internal parasites.

Antimicrobial and physical-mechanical properties of pectin/papaya puree/cinnamaldehyde nanoemulsion edible composite films

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)

The influence of diet on the effectiveness of garlic oil and cinnamaldehyde to manipulate in vitro ruminal fermentation and methane production.

The objective of this study was to evaluate the effects of increasing doses [0 (control: CON), 20, 60, 180 and 540 mg/L incubation medium] of garlic oil (GO) and cinnamaldehyde (CIN) on in vitro ruminal fermentation of two diets. Batch cultures of mixed ruminal microorganisms were inoculated with ruminal fluid from four sheep fed a medium-concentrate diet (MC; 50 : 50 alfalfa hay : concentrate) or four sheep fed a high-concentrate diet (HC; 15 : 85 barley straw : concentrate). Diets MC and HC were representative of those fed to dairy and fattening ruminants, respectively. Samples of each diet were used as incubation substrates for the corresponding inoculum, and the incubation was repeated on 4 different days (four replicates per experimental treatment). There were GO × diet-type and CIN × diet-type interactions (P < 0.001–0.05) for many of the parameters determined, indicating different effects of both oils depending on the diet type. In general, effects of GO were more pronounced for MC compared with HC diet. Supplementation of GO did not affect (P > 0.05) total volatile fatty acid (VFA) production at any dose. For MC diet, GO at 60, 180 and 540 mg/L decreased (P < 0.05) molar proportion of acetate (608, 569 and 547 mmol/mol total VFA, respectively), and increased (P < 0.05) propionate proportion (233, 256 and 268 mmol/mol total VFA, respectively), compared with CON values (629 and 215 mmol/mol total VFA for acetate and propionate, respectively). A minimum dose of 180 mg of GO/L was required to produce similar modifications in acetate and propionate proportions with HC diet, but no effects (P > 0.05) on butyrate proportion were detected. Methane/VFA ratio was reduced (P < 0.05) by GO at 60, 180 and 540 mg/L for MC diet (0.23, 0.16 and 0.10 mol/mol, respectively), and by GO at 20, 60, 180 and 540 mg/L for HC diet (0.19, 0.19, 0.16 and 0.08 mol/mol, respectively), compared with CON (0.26 and 0.21 mol/mol for MC and HC diets, respectively). No effects (P = 0.16–0.85) of GO on final pH and concentrations of NH3-N and lactate were detected. For both diet types, the highest CIN dose decreased (P < 0.05) production of total VFA, gas and methane, which would indicate an inhibition of fermentation. Compared with CON, CIN at 180 mg/L increased (P < 0.05) acetate proportion for the MC (629 and 644 mmol/mol total VFA for CON and CIN, respectively) and HC (525 and 540 mmol/mol total VFA, respectively) diets, without affecting the proportions of any other VFA or total VFA production. Whereas for MC diet CIN at 60 and 180 mg/L decreased (P < 0.05) NH3-N concentrations compared with CON, only a trend (P < 0.10) was observed for CIN at 180 mg/L with the HC diet. Supplementation of CIN up to 180 mg/L did not affect (P = 0.18–0.99) lactate concentrations and production of gas and methane for any diet. The results show that effectiveness of GO and CIN to modify ruminal fermentation may depend on diet type, which would have practical implications if they are confirmed in vivo.

Modulatory impact of cinnamaldehyde on immune cells is partly due to induction of apoptosis.

Cinnamaldehyde (CA) has been reported to have antiinflammatory, anti-bacterial, anti-fungal, chemoprotective and anti-carcinogenic activity. Here, we further investigated the immune-modulating capacity of CA.

Selectivity control in Pt-catalyzed cinnamaldehyde hydrogenation

Chemoselectivity is a cornerstone of catalysis, permitting the targeted modification of specific functional groups within complex starting materials. Here we elucidate key structural and electronic factors controlling the liquid phase hydrogenation of cinnamaldehyde and related benzylic aldehydes over Pt nanoparticles. Mechanistic insight from kinetic mapping reveals cinnamaldehyde hydrogenation is structure-insensitive over metallic platinum, proceeding with a common Turnover Frequency independent of precursor, particle size or support architecture. In contrast, selectivity to the desired cinnamyl alcohol product is highly structure sensitive, with large nanoparticles and high hydrogen pressures favoring C=O over C=C hydrogenation, attributed to molecular surface crowding and suppression of sterically-demanding adsorption modes. In situ vibrational spectroscopies highlight the role of support polarity in enhancing C=O hydrogenation (through cinnamaldehyde reorientation), a general phenomenon extending to alkyl-substituted benzaldehydes. Tuning nanoparticle size and support polarity affords a flexible means to control the chemoselective hydrogenation of aromatic aldehydes.

Platinum-catalysed cinnamaldehyde hydrogenation in continuous flow

Platinum is one of the most widely used hydrogenation catalysts. Here we describe the translation of batch reactions to continuous flow, affording tunable C=O versus C=C hydrogenation over a Pt/SiO2 catalyst, resulting in high steady state activity and single-pass yields in the selective hydrogenation of cinnamaldehyde to cinnamyl alcohol under mild conditions. Negligible catalyst deactivation occurs under extended flow operation due to removal of reactively-formed poisons from the reaction zone. Process intensification imparts a four-fold enhancement in cinnamyl alcohol productivity.

Sequential injection analysis system with spectrophotometric detection for determination of norfloxacin and ciprofloxacin in pharmaceutical formulations

This work proposes a sequential injection analysis (SIA) system for the spectrophotometric determination of norfloxacin (NOR) and ciprofloxacin (CIP) in pharmaceutical formulations. The methodology was based on the reaction of these drugs with p-(dimethylamino)cinnamaldehyde in micellar medium, producing orange colored products (λmax = 495 nm). Beer´s law was obeyed in the concentration range from 2.75x10-5 to 3.44x10-4 mol L-1 and 3.26x10-5 to 3.54x10-4 mol L-1 for NOR and CIP, respectively and sampling rate was 25 h-1. Commercial samples were analyzed and results obtained through the proposed method were in good agreement with those obtained using the reference procedure for a 95% confidence level.

Identification of the major fungitoxic component of cinnamon bark oil

The study was done to identify the most active fungitoxic component of cinnamon bark (Cinnamomum zeylanicum) oil that can be used as a marker for standardization of cinnamon extract or oil based natural preservative of stored seeds. Aspergillus flavus and A. ruber were used as test fungi. The hexane extracted crude oil and the hydro-distilled essential oil from cinnamon bark had complete growth inhibition concentration (CGIC) of 300 and 100 µl/l, respectively. Both oils produced three fractions on preparative thin layer silica-gel chromatography plates. The fraction-2 of either oil was the largest and most active, with CGIC of 200 µl/l, but the fungitoxicity was also retained in the other two fractions. The fraction-1 and 3 of the crude oil reduced growth of both the fungal species by 65%, and those of distilled oil by 45% at 200 µl/l. The CGIC of these fractions from both the sources was above 500 µl/l. The gas chromatography and mass spectrometry (GC-MS) of the fraction-2 of the hexane extract revealed that it contained 61% cinnamaldehyde, 29% cinnamic acid, and two minor unidentified compounds in the proportion of 4% and 6%. The GC-MS of the fraction-2 of the distilled oil revealed that it contained 99.1% cinnamaldehyde and 0.9% of an unidentified compound. The CGIC of synthetic cinnamaldehyde was 300 µl/l and that of cinnamic acid above 500 µl/l. The 1:1 mixture of cinnamaldehyde and cinnamic acid had CGIC of 500 µl/l. The data revealed that cinnamaldehyde was the major fungitoxic component of hexane extract and the distilled essential oil of cinnamon bark, while other components have additive or synergistic effects on total fungitoxicity. It is suggested that the natural seed preservative based on cinnamon oil can be standardized against cinnamaldehyde.

Traitement des mélanges par le système trigéminal

Le système trigéminal –tout comme l’olfaction et la gustation– est un sens chimique qui permet la perception des informations chimiosensorielles de notre environnement. Contrairement à l’olfaction et à la gustation, notre connaissance du traitement des mélanges par le système trigéminal est limitée. Nous avons donc utilisé des mélanges de trois agonistes relativement spécifiques à des récepteurs (eucalyptol, agoniste TRPM8; aldéhyde cinnamique, agoniste TRPA1 ; camphre, agoniste TRPV1) et d’une odeur pure (alcool phényléthylique) dans différentes proportions afin de déterminer les dimensions de base de la perception trigéminale. Quatre dimensions principales se sont avérées pertinentes: l’intensité, la sensation de chaleur, la sensation de froid et la douleur. Nous avons utilisé ces dimensions pour étudier la perception de mélanges et de combinaisons dans différentes proportions d’un stimulus qui procure une sensation de froid (eucalyptol) et d’un stimulus qui procure une sensation de chaleur (aldéhyde cinnamique). Les résultats indiquent que les mélanges obtiennent généralement des scores plus élevés que les combinaisons sur les dimensions « intensité », « sensation de chaleur » et « douleur » alors que les combinaisons obtiennent des scores plus élevés sur la dimension « sensation de froid ». Ces résultats suggèrent des interactions spécifiques pour les différentes dimensions de la perception trigéminale. Nous en venons à la conclusion d’un effet d’additivité pour les mélanges sur les dimensions « intensité », « sensation de chaleur » et « douleur » alors que nous observons plutôt un effet de suppression de la perception de froid pour les deux stimuli dans les mélanges, ce qui semble indiquer des interactions particulières pouvant prendre place aux niveaux périphérique ou central.

Beckmann rearrangement of E,E-cinnamaldoxime on rare earth exchanged (Ce3+, La3+, and RE3+) HFAU-Y zeolites: An efficient green process for the synthesis of isoquinoline

In this paper, a novel application of solid acid catalysts in the Beckmann rearrangement of E,E-cinnamaldoxime in the synthesis of an important heterocyclic compound; isoquinoline is reported. E,E-Cinnamaldoxime under ambient reaction conditions on zeolite catalysts underwent Beckmann rearrangement to produce isoquinoline in yields of ca. 86–95%. Cinnamonitrile and cinnamaldehyde were formed as by-products. LaH-Y zeolite produces maximum amount of the desired product (yield 95.6%). However, the catalysts are susceptible for deactivation due to the basic nature of the reactants and products, which neutralize the active sites. H-Y zeolite is more susceptible (22% deactivation in 10 h) for deactivation compared to the cerium-exchanged counterpart (18% deactivation in 10 h). Thus, the optimal protocol allows isoquinoline to be synthesised in excellent yields through the Beckmann rearrangement of cinnamaldoxime. The reaction is simple, effective, does not involve any other additives, and environmentally benign.

Combined action of S-carvone and mild heat treatment on Listeria monocytogenes Scott A

The combined action of the plant-derived volatile, S-carvone, and mild heat treatment on the food-borne pathogen, Listeria monocytogenes, was evaluated. The viability of exponential phase cultures grown at 8 °C could be reduced by 1·3 log units after exposure to S-carvone (5 mmol l−1) for 30 min at 45 °C, while individual treatment with S-carvone or exposure to 45 °C for 30 min did not result in a loss in viability. Other plant-derived volatiles, namely carvacrol, cinnamaldehyde, thymol and decanal, were also found to reduce the viability of L. monocytogenes in combination with the same mild heat treatment at concentrations of 1·75 mmol l−1, 2·5 mmol l−1, 1·5 mmol l−1 and 2 mmol l−1, respectively. These findings show that essential oil compounds can play an important role in minimally processed foods, and can be used in the concept of Hurdle Technology to reduce the intensity of heat treatment or other individual hurdles.

Sequential injection analysis system with spectrophotometric detection for determination of norfloxacin and ciprofloxacin in pharmaceutical formulations

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Efeitos da rifampicina na farmacocinética e hepatotoxicidade da isoniazida

Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)