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- High dietary protein, n − 3/n − 6 ratio and β-carotene enhances Paracentrotus lividus (Lamarck, 1816) larval developmentPublication . Gomes, Ana S.; Lourenço, Sílvia; Santos, Pedro M.; Neves, Marta; Adão, Pedro; Tecelão, Carla; Pombo, AnaThe nutritional characteristics of microalgae affect the growth, survival and fatty acid composition of sea urchin larvae. This study aimed to evaluate the influence of nutritive characteristics of single microalgal diets in Paracentrotus lividus (Lamarck, 1816) larval development, growth, and condition. Larvae of P. lividus were fed with three monospecific microalgal diets, Rhodomonas sp. (Rho), Dunaliella tertiolecta (Duna) and the diatom Chaetoceros calcitrans (Chae), and their development and growth were analysed until competence. Additionally, the fatty acid (FA) profile of larvae was analysed at competence and compared with the FA profile of the correspondent diet. The three groups of larvae attained competence simultaneously with differences in growth performance. The larvae fed with Chae attained the largest stomach and the shortest post-oral arm. The larvae were able to accumulate long-chain polyunsaturated fatty acids (PUFA), such as docosahexaenoic (DHA, C22:6n − 3), eicosapentaenoic (EPA, C20:5n − 3) and arachidonic (ARA, C20:4n − 6) acids, either by assimilation and retention of dietary FA or by the synthesis from α-linolenic acid (ALA, C18:3n − 3) and linoleic acid (LA, C18:2n − 6). Furthermore, the low DHA/EPA ratio and high EPA/ARA and n − 3/n − 6 ratios of Rho and Chae and the high levels of the β-carotene present in Chae improved larval growth and development. In conclusion, the results indicated that of the three microalgal diets tested, C. calcitrans provided important nutritional characteristics, especially in terms of FA composition and carotenoids, improving P. lividus larval growth and condition.
- Morphological and mechanical characterization of films incorporating Porphyran extracted from Porphyra dioicaPublication . Baptista, Ricardo S.; Teles, Marco; Adão, Pedro; Afonso, Clélia; Bernardino, Raul; Bernardino, Susana; Ferro, Alberto C.; Elias, Sara; Guedes, MafaldaThis paper studies the effects of glycerol plasticizers and/or alginate, pectin, and carboxymethylcellulose polysaccharides on the mechanical and physical properties of porphyran-based films to evaluate the films’ ability to be used as food packaging. Films were characterized in terms of their composition, microstructural and morphological features, thermal properties, water interaction, and mechanical performance. All films are homogeneous, transparent, and slightly brownish in color. The structures are amorphous and crosslinked, showing the films’ thermoset nature. Moisture content and water solubility depend on the second polysaccharide added to the porphyran, but they both increase with the addition of glycerol to the formulations; water vapor permeability is strongly affected by the second polysaccharide in the formulation. The films display stiff and brittle mechanical behavior, but ductility increases significantly in formulations containing glycerol plasticizers. The barrier and mechanical performance values of the materials produced were found to be lower than those reported for commercial food packaging. The formulations containing glycerol displayed lower water vapor permeability values, ranging from 2.98 for porphyran/carboxymethylcellulose/glycerol to 6.65 mm.g.d-1.m-2.kPa-1 for porphyran/alginate/glycerol films. All films, except porphyran/glycerol and porphyran/alginate/glycerol, had ultimate tensile strengths above 10 MPa—the threshold value that ensures that a package is ductile enough to withstand handling and forming operations. Furthermore, the porphyran/ pectin/glycerol and porphyran/carboxymethylcellulose/glycerol films displayed sufficiently high ductility values of 2.94 and 3.10%, respectively. These results indicate that the studied porphyran/pectin/glycerol and porphyran/carboxymethylcellulose/glycerol formulations have a combination of physical and mechanical properties that ensure adequate film integrity and function through the complete food packaging supply chain. The results here reported represent an opportunity to extend the scope of porphyran films to applications in the dry food packaging industry.
- Cu(II) and V(IV)O complexes with tri- or tetradentate ligands based on (2-hydroxybenzyl)- L-alanines reveal promising anticancer therapeutic potentialPublication . Ribeiro, Nádia; Bulut, İpek; Cevatemre, Buse; Teixeira, Carlos; Yildizhan, Yasemin; André, Vânia; Adão, Pedro; Pessoa, João; Acilan, Ceyda; Correia, IsabelFour new ligand precursors (H2L1–H2L4), derived from the Mannich condensation of two amino acids (L-Val and L-Phe) and two 3,5-disubstituted phenols (t-Bu or Me), and the corresponding oxidovanadium(IV) (1–4) and copper(II) (6–7) complexes are synthesized. Two other related compounds (H2L5 and H2L6), containing an additional 2-methyl-pyridine arm, and the corresponding VIVO (5) and CuII (8–9) complexes were also obtained. All metal complexes are monomeric in the solid state, having a solvent molecule or a chloride ion in the coordination sphere. The in vitro cytotoxic activity of all compounds is evaluated against cancer cells from different origins. The IC50 values at 72 h are in the range of 6–15 μM for HeLa cells, 4–17 μM for A-549 cells and >25 μM for MDA-MB-231 cells, except for [VIVOL1(CH3OH)] (1) and [CuL6(H2O)] (9). With the exception of H2L6, overall, the metal complexes are more cytotoxic than the corresponding ligand precursors. Globally, the cellular viability data show that (i) the L-Phe derived compounds are more cytotoxic than the corresponding L-Val complexes; (ii) the presence of the bulkier t-Bu groups increases the cytotoxicity; (iii) the presence of a 2-methyl pyridine arm increases considerably the cytotoxicity; and (iv) the CuII-complexes are more cytotoxic than the VIVO-compounds. Complexes [VIVOL3(CH3OH)] (3), [CuL3(H2O)] (7) and [CuL5(H2O)] (8) were further evaluated and their mechanism of action was determined to be apoptosis, evidenced by AnnexinV staining and the increase in caspase 3/7 activity. Compounds 3, 7 and 8 also exhibit DNA cleavage activity, involving the formation of reactive oxygen species and were able to induce genomic damage in cells as determined by COMET assay.
- L-Phenylalanine derived tripodal vanadium complexes as catalysts for the asymmetric reductive coupling of benzaldehydePublication . Teixeira, Carlos M.; Adão, Pedro; Carvalho, M. Fernanda N.N.; Gomes, Clara S.B.; Pessoa, João CostaTwo tripodal vanadium complexes derived from modified L-phenylalanine were prepared and characterised. Both compounds were tested for their catalytic activity in the reductive coupling of benzaldehyde. Overall, the complexes are capable of catalysing the reductive coupling of benzaldehyde in the presence of metallic zinc as co-reductant and alkylammonium or alkylpyridinium acetate salts in ethanol under mild aerobic conditions. While benzyl alcohol is generally the major product, the yield of hydrobenzoin reaches ca. 38% under these conditions. Enantioselectivities reach 39% and there is a preferential formation of the trans diastereoisomer of hydrobenzoin. Attempts to study some aspects of the underlying mechanism were made. It was found that metallic zinc is capable of reducing the complexes to VIII species, which are likely to be the active catalytic species. The methodology described may set up a basis for the development of catalytic systems for the asymmetric synthesis of hydrobenzoins under mild conditions, not requiring chlorosilanes as electrophilic reagents for the regeneration of the catalyst.
- Enhancement of the antioxidant and antimicrobial activities of porphyran through chemical modification with tyrosine derivativesPublication . Adão, Pedro; Reboleira, João; Teles, Marco; Santos, Beatriz; Ribeiro, Nádia; Teixeira, Carlos M.; Guedes, Mafalda; Pessoa, João Costa; Bernardino, Susana M.The chemical modification of porphyran hydrocolloid is attempted, with the objective of enhancing its antioxidant and antimicrobial activities. Sulfated galactan porphyran is obtained from commercial samples of the red algae Porphyra dioica using Soxhlet extraction with water at 100ºC and precipitation with isopropyl alcohol. The extracted porphyran is then treated with modified L-tyrosines in aqueous medium in the presence of NaOH, at ca. 70ºC. The modified tyrosines L1 and L2 are prepared through a Mannich reaction with either thymol or 2,4-di-tert-butylphenol, respectively. While the reaction with 2,4-di-tert-butylphenol yields the expected tyrosine derivative, a mixture of products is obtained with thymol. The resulting polysaccharides are structurally characterized and the respective antioxidant and antimicrobial activities are determined. Porphyran treated with the N-(2-hydroxy-3,5-di-tert-butyl-benzyl)-L-tyrosine derivative, POR-L2, presents a noticeable superior radical scavenging and antioxidant activity compared to native porphyran, POR. Furthermore, it exhibited some antimicrobial activity against S. aureus. The surface morphology of films prepared by casting with native and modified porphyrans is studied by SEM/EDS. Both POR and POR-L2 present potential applicability in the production of films and washable coatings for food packaging with improved protecting characteristics.
- Development and characterization of flms for food application incorporating Porphyran extracted from Porphyra dioicaPublication . Teles, Marco; Adão, Pedro; Afonso, Clélia; Bernardino, Raul; Guedes, Mafalda; Baptista, Ricardo; Bernardino, SusanaNon-biodegradable plastic is one of the biggest environmental problems of our lifetime and, considering the present societal needs, it will get worse. Consequently, there is an urgent need to develop sustainable and renewable alternatives to plastic, such as plastic-like materials obtained from biodegradable polymers, namely sulfated polysaccharides, considered one of the most viable alternatives. There is also a need to obtain these materials in an environmentally and economically sustainable way. The hereby developed process of obtaining film-forming solutions from semi-refined porphyran (PorphSR) uses a green solvent (hot water) with a high extraction yield of semi-refined porphyran (26.66 +- 0.27%) in a reproducible way and with low levels of contaminants. The obtained semi-refined porphyran showed good antioxidant potential in all tests performed: HPSA (D0.066 +- 0.002), DPPH (2.23 +- 0.78%), FRAP (0.420 +- 0.014 eq. ascorbic acid ug mg-1 of extract) and ABTS (20.46 +- 0.90%). After being cast into films, the most notable antioxidant properties were those of the semi-refined porphyran in the DPPH, FRAP and ABTS assays and of the pectin, (PorphSR_PcT and PorphSR_PcT_Gly) in the HPSA assay. Morphologically, the films showed relatively homogeneous and low roughness surfaces. It is concluded that the described method to obtain semi-refined porphyran is feasible and reproducible, and that the developed films, mainly PorfP2_PcT_Gly, proved to be a potential candidate for non-biodegradable plastic substitutes.
- Optimization of extraction conditions for Gracilaria gracilis extracts and their antioxidative stability as mart of microfiber food coating additivesPublication . Reboleira, João; Ganhão, Rui; Mendes, Susana; Adão, Pedro; Andrade, Mariana; Vilarinho, Fernanda; Sanches-Silva, Ana; Sousa, Dora; Mateus, Artur; Bernardino, SusanaIncorporation of antioxidant agents in edible films and packages often relies in the usage of essential oils and other concentrated hydrophobic liquids, with reliable increases in antimicrobial and antioxidant activities of the overall composite, but with less desirable synthetic sources and extraction methods. Hydroethanolic extracts of commercially-available red macroalgae Gracilaria gracilis were evaluated for their antioxidant potential and phenolic content, as part of the selection of algal biomass for the enrichment of thermoplastic film coatings. The extracts were obtained through use of solid-liquid extractions, over which yield, DPPH radical reduction capacity, total phenolic content, and FRAP activity assays were measured. Solid-to-liquid ratio, extraction time, and ethanol percentages were selected as independent variables, and response surface methodology (RSM) was then used to estimate the e ect of each extraction condition on the tested bioactivities. These extracts were electrospun into polypropylene films and the antioxidant activity of these coatings was measured. Similar bioactivities were measured for both 100% ethanolic and aqueous extracts, revealing high viability in the application of both for antioxidant coating purposes, though activity losses as a result of the electrospinning process were above 60% in all cases.
- Poultry shelf-life enhancing potential of nanofibers and nanoparticles containing Porphyra dioica extractsPublication . Reboleira, João; Adão, Pedro; Guerreiro, Sara F.C.; Dias, Juliana R.; Ganhão, Rui; Mendes, Susana; Andrade, Mariana; Vilarinho, Fernanda; Sanches-Silva, Ana; Mateus, Artur; Alves, Nuno; Bernardino, Susana M.Aqueous extracts of commercially available red macroalgae Porphyra dioica were integrated as inner coatings of food-grade polypropylene (PP) films through use of electrospinning and electrospraying technologies. Two coating formulations (A = 5 wt% P. dioica extract and 7.5 wt% polyvinyl alcohol (PVA); B = 1 wt% P. dioica extract, 1 wt% PVA, and 17% gelatine) were evaluated as to their capacity to delay spoilage of minced chicken breasts, through monitoring of microbial growth (total mesophile aerobic colony counts), colour stability, lipid oxidation (thiobarbituric acid reactive substances (TBARS)), and sensory analysis over a 4-day refrigerated storage. Scanning electron microscopy (SEM) imaging revealed an increased nanofiber and nanoparticle density on extract-enriched fibers, without compromise to their morphology or the homogeneity of the coatings. Total microbial counts on coating B samples was significantly (p < 0.001) reduced compared to uncoated plastic wraps. The coated samples also exhibited fewer colour degradation, though the coatings did not di er substantially from uncoated plastic wrap. Sensory analysis test subjects successfully distinguished the raw samples based on their treatment and gave a positive approval rating (66.7%) to the extract-enriched coatings when asked about edibility post storage.
- Development and characterization of films for food application incorporating porphyran extracted from Porphyra dioicaPublication . Teles, Marco; Adão, Pedro; Afonso, Clélia; Bernardino, Raul; Guedes, Mafalda; Baptista, Ricardo; Bernardino, SusanaNon-biodegradable plastic is one of the biggest environmental problems of our lifetime and, considering the present societal needs, it will get worse. Consequently, there is an urgent need to develop sustainable and renewable alternatives to plastic, such as plastic-like materials obtained from biodegradable polymers, namely sulfated polysaccharides, considered one of the most viable alternatives. There is also a need to obtain these materials in an environmentally and economically sustainable way. The hereby developed process of obtaining film-forming solutions from semi-refined porphyran (PorphSR) uses a green solvent (hot water) with a high extraction yield of semi-refined porphyran (26.66 +- 0.27%) in a reproducible way and with low levels of contaminants. The obtained semi-refined porphyran showed good antioxidant potential in all tests performed: HPSA (D0.066 +- 0.002), DPPH (2.23 +- 0.78%), FRAP (0.420 +- 0.014 eq. ascorbic acid ug mg-1 of extract) and ABTS (20.46 0.90%). After being cast into films, the most notable antioxidant properties were those of the semi-refined porphyran in the DPPH, FRAP and ABTS assays and of the pectin, (PorphSR_PcT and PorphSR_PcT_Gly) in the HPSA assay. Morphologically, the films showed relatively homogeneous and low roughness surfaces. It is concluded that the described method to obtain semi-refined porphyran is feasible and reproducible, and that the developed films, mainly PorfP2_PcT_Gly, proved to be a potential candidate for non-biodegradable plastic substitutes.
- Cu(II) complexes derived from N-carboxymethyl and N-carboxyethyl amino acids as catalysts for asymmetric oxidative coupling of 2-naphtholPublication . Adão, Pedro; Teixeira, Carlos M.; Carvalho, M. Fernanda N.N.; Kuznetsov, Maxim L.; Gomes, Clara S.B.; Pessoa, João CostaThe synthesis, characterization and catalytic performance of chiral Cu(II) complexes derived from N-carboxymethylated and N-carboxyethylated amino acids is reported. The ligand precursors are prepared by single step N-alkylation of the sodium salts of the appropriate chiral amino acid with either sodium chloroacetate or sodium 3-chloropropionate in water. The Cu(II) complexes are obtained upon reaction of Cu(CH3COO)2 with the aqueous or alcoholic suspension of the suitable ligand under vigorous stirring or ultrasound irradiation at room temperature. The Cu(II) compounds are characterised by EPR, UV–vis, circular dichroism and ESI-MS. The molecular structures of two of the prepared complexes are also obtained by single-crystal X-ray diffraction analysis. The catalytic activity of the complexes in the asymmetric oxidative coupling of 2-naphthol is described. All compounds exhibit moderate activity, selectivity and enantioselectivity in ethanol/water mixtures, under aerobic conditions and using potassium iodide as additive. The yields of 1,1′-bi-2-naphthol (BINOL) reached 50% under the optimal conditions, while enantiomeric excesses reached ca. 48%. The effect of variables such as ligand substituents, solvent, temperature and additives on the catalytic activity is also described. In the absence of a base, the complexes only show catalytic activity in the presence of alkali metal iodide such as KI. Details of the oxidative coupling mechanism are studied using spectroscopic and electrochemical methodologies.