Reaction between hydroxycinnamic acids and anthocyanin-pyruvic acid adducts yielding new portisins

Three new anthocyanin-derived pigments were found to occur in a 2-year-old Port red wine. Their structures were elucidated through LC/DAD-MS and NMR analysis and were found to correspond to a pyranoanthocyanin moiety linked to substituted cinnamyl substituents. The structures of these compounds are very similar to the one already reported for portisins, with a phenolic moiety replacing the catechin moiety. The newly formed anthocyanin-derived compounds display a bathochromic shift of the lambdamax ( approximately 540 nm) when compared with their anthocyanin-pyruvic acid adduct precursor (lambdamax = 511 nm), which may be due to the extended conjugation of the pi electrons in the structures of those pigments. Studies performed in model solutions helped to clarify the formation mechanism of these pigments that can result from the nucleophilic attack of the olefinic double bond of a hydroxycinnamic acid to the eletrophilic C-10 position of the anthocyanin-pyruvic acid adduct, followed by the loss of a formic acid molecule and decarboxylation. The chromatic characterization of these malvidin-3-glucoside-derived compounds revealed a higher resistance to discoloration against the nucleophilic attack by water and bisulfite when compared to malvidin-3-glucoside that is almost converted into its colorless hemiacetal form. However, the resistance to discoloration of these new pigments is not as high as the one reported for catechin-derived portisins. This could be explained by the presence of a smaller group (hydroxycinnamyl group), which does not protect so efficiently the chromophore against nucleophilic attack at the C-2 position. The occurrence of these pigments in red wine highlights new chemical pathways involving anthocyanin-pyruvic acid derivatives as precursors for the formation of new pigments in subsequent stages of wine aging that may contribute to its color evolution.     

Influence of Cultivar and Environmental Conditions on the Triacylglycerol Profile of Hazelnut (Corylus avellana L.)

The oil of several hazelnut (Corylus avellana L.) samples was extracted and evaluated for their triacylglycerol (TAG) composition. Trials were conducted in two Portuguese localities (Vila Real and Felgueiras) during three consecutive years and involved a total of 19 cultivars. The samples were analyzed by reversed-phase high-performance liquid chromatography with evaporative light-scattering detection. Sample preparation was fast and simple, consisting only of the dissolution of the oil in acetone, homogenization, and filtration, allowing this technique to be suitable for routine analyses. All samples presented a similar qualitative profile composed of eleven compounds: LLL, OLL, PLL, OOL, POL, PPL, OOO, POO, PPO, SOO and PSO (P, palmitoyl; S, stearoyl; O, oleoyl; and L, linoleoyl). The main components were OOO, LOO, and POO, reflecting the high content of oleic acid in hazelnut oils. A total of 79 different samples were studied, and the obtained data were statistically analyzed. Significant differences were verified in canonical variate plots when cultivars were grouped by country of origin. In general, the American cultivars were richer in TAGs with saturated fatty acids moieties, and the group of French, German, and English cultivars was richer in TAGs containing linoleic acid moieties. Differences were also significant when cultivars were grouped by year of production, showing that besides genetic factors, the TAG composition can be influenced by environmental factors.     

Lipid Utilization Pathways Induced by Early Training in Standardbred Trotters and Thoroughbreds

Controversial results on lipid utilization as an energy source during training in horses are found in the literature. The objective of this study was to assess blood lipid profile during different training programs in horses. Seventeen Standardbred horses (400 ± 50 kg) and 17 Thoroughbred horses (380 ± 15 kg) followed different training programs. Blood lipid profile, including triglycerides (TGs), total cholesterol, high-density lipoprotein (HDL), and low-density lipoprotein (LDL), was analyzed, and very-low-density lipoprotein (VLDL) concentration was calculated. Data were analyzed using Student t test, and linear regressions were done. Cholesterol and LDL decreased during training programs in Standardbred trotters (P = .0001 and P = .0053, respectively), and VLDL was found to be close to the significance level (P = .053). Blood lipid profile, including TGs (P = .0014), cholesterol (P = .0057), HDL (P = .0128), LDL (P = .0091), and VLDL (P = .0014), varied throughout the training program in Thoroughbred horses. Negative slope of blood lipids and positive slope of TG linear regression in Standardbred trotters were significant for all parameters (P ≤ .05), whereas cholesterol and LDL regression showed poor P and r² values and HDL P value was slightly above the significance level (P = .069) in Thoroughbred horses. TGs and VLDL showed a positive linear trend in Thoroughbred horses (P = .002). Exercise and different training programs lead to significant variations of lipid profile and lipid utilization in horses. Lipid utilization as an energy source improved with training in Standardbred trotters, whereas this was not the case in Thoroughbred horses. Further studies on the effect of training programs using different conditions and horse breeds would be necessary to understand lipid utilization as an energy source in athletic horses.     

Natural Benzo/Acetophenones as Leads for New Synthetic Acetophenone Hybrids Containing a 1,2,3-Triazole Ring as Potential Antifouling Agents

Marine biofouling is a natural process that represents major economic, environmental, and health concerns. Some booster biocides have been used in biofouling control, however, they were found to accumulate in environmental compartments, showing negative effects on marine organisms. Therefore, it is urgent to develop new eco-friendly alternatives. Phenyl ketones, such as benzophenones and acetophenones, have been described as modulators of several biological activities, including antifouling activity (AF). In this work, acetophenones were combined with other chemical substrates through a 1,2,3-triazole ring, a strategy commonly used in Medicinal Chemistry. In our approach, a library of 14 new acetophenone–triazole hybrids was obtained through the copper(I)-catalyzed alkyne-azide cycloaddition “click” reaction. All of the synthesized compounds were evaluated against the settlement of a representative macrofouling species, Mytilus galloprovincialis, as well as on biofilm-forming marine microorganisms, including bacteria and fungi. The growth of the microalgae Navicula sp. was also evaluated after exposure to the most promising compounds. While compounds 6a, 7a, and 9a caused significant inhibition of the settlement of mussel larvae, compounds 3b, 4b, and 7b were able to inhibit Roseobacter litoralis bacterial biofilm growth. Interestingly, acetophenone 7a displayed activity against both mussel larvae and the microalgae Navicula sp., suggesting a complementary action of this compound against macro- and microfouling species. The most potent compounds (6a, 7a, and 9a) also showed to be less toxic to the non-target species Artemia salina than the biocide Econea^®. Regarding both AF potency and ecotoxicity activity evaluation, acetophenones 7a and 9a were put forward in this work as promising eco-friendly AF agents.     

Gene pool and connectivity patterns of Pinna nobilis in the Balearic Islands (Spain,Western Mediterranean Sea): Implications for its conservation through restocking

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Dietary micronutrient composition affects fillet texture and muscle cell size in Atlantic salmon (Salmo salar)

During the past 20 years, plant ingredients have taken over as the main constituents in feed for Atlantic salmon. This has changed the nutrient composition of the feeds, the bioavailability of nutrients and perhaps nutrient metabolism. Plant‐based diets also contain more anti‐nutrients. The EU‐funded project ARRAINA re‐evaluated recommendations for micronutrient supplementation to Atlantic salmon feeds, and the present study compared a diet supplemented with micronutrients according to NRC (2011) (control diet, 100% NP (nutrient package)) with a diet supplemented according to the new recommendations (New NP). Tissue concentrations of pyridoxine, pantothenic acid, niacin, vitamin C, Zn and Se were significantly higher; and Cu was lower in Atlantic salmon fed the diet with the New NP compared to the control fish. The New NP also gave a near significant effect on growth, decreased muscle firmness and increased muscle cell size, and it affected metabolism of nitrogen‐containing metabolites in the muscle. While we cannot be certain which micronutrient(s) gave these effects, the B vitamins are probable candidates, since they are mediators of intermediary metabolism and have been shown to influence some of the affected metabolites.     

Assessing genetic variability in germplasm of Phaseolus vulgaris L. collected in Northern Portugal

The common bean (Phaseolus vulgaris L.) is the most consumed legume in the world. In Portugal, the geographic isolation of the region surrounded by the mountainous barrier of Peneda-Gerês, Barroso and Marão is thought to have the safeguard of a large number of adapted bean populations. In order to assess the value of this germplasm to breeding programs, a study of 20 Portuguese landraces collected in this Northern region were evaluated for agronomical (days to flowering, plant height, days to harvest, weight of seeds per plant and 100 seeds weight), chemical (crude protein) and genetic diversity (microsatellite DNA).     

Estimation of roaming dog populations in Timor Leste

The continued spread of rabies through the eastern islands of Indonesia poses a risk of rabies introduction to Timor Leste. To prepare for such an incursion and to undertake surveillance activities, the size and distribution of the roaming dog population needs to be estimated. We present the results of the first such surveys ever undertaken in Timor Leste.     

Detection of RHDV strains in the Iberian hare (Lepus granatensis): earliest evidence of rabbit lagovirus cross-species infection

Rabbit hemorrhagic disease virus (RHDV) is a highly lethal Lagovirus, family Caliciviridae, that threatens European rabbits (Oryctolagus cuniculus). Although a related virus severely affects hares, cross-species infection was only recently described for new variant RHDV in Cape hares (Lepus capensis mediterraneus). We sequenced two strains from dead Iberian hares (Lepus granatensis) collected in the 1990s in Portugal. Clinical signs were compatible with a Lagovirus infection. Phylogenetic analysis of the complete capsid gene positioned them in the RHDV genogroup that circulated on the Iberian Peninsula at that time. This is the earliest evidence of RHDV affecting a species other than European rabbits.     

Immunosuppression abrogates resistance of young rabbits to Rabbit Haemorrhagic Disease (RHD)

Rabbit Haemorrhagic Disease (RHD) is caused by a calicivirus (RHDV) that kills 90% of infected adult European rabbits within 3 days. Remarkably, young rabbits are resistant to RHD. We induced immunosuppression in young rabbits by treatment with methylprednisolone acetate (MPA) and challenged the animals with RHDV by intramuscular injection. All of these young rabbits died within 3 days of infection due to fulminant hepatitis, presenting a large number of RHDV-positive dead or apoptotic hepatocytes, and a significant seric increase in cytokines, features that are similar to those of naïve adult rabbits infected by RHDV. We conclude that MPA-induced immunosuppression abrogates the resistance of young rabbits to RHD, indicating that there are differences in the innate immune system between young and adult rabbits that contribute to their distinct resistance/susceptibility to RHDV infection.