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- Structure of Hierridin C, Synthesis of Hierridins B and C, and Evidence for Prevalent Alkylresorcinol Biosynthesis in PicocyanobacteriaPublication . Costa, Margarida; Sampaio-Dias, Ivo E.; Castelo-Branco, Raquel; Scharfenstein, Hugo; Rezende de Castro, Roberta; Silva, Artur; Schneider, Maria Paula C.; Araújo, Maria João; Martins, Rosario; Domingues, Valentina F.; Nogueira, Fátima; Camões, Vera; Vasconcelos, Vitor M.; Leão, Pedro N.Small, single-celled planktonic cyanobacteria are ubiquitous in the world's oceans yet tend not to be perceived as secondary metabolite-rich organisms. Here we report the isolation and structure elucidation of hierridin C, a minor metabolite obtained from the cultured picocyanobacterium Cyanobium sp. LEGE 06113. We describe a simple, straightforward synthetic route to the scarcely produced hierridins that relies on a key regioselective halogenation step. In addition, we show that these compounds originate from a type III PKS pathway and that similar biosynthetic gene clusters are found in a variety of bacterial genomes, most notably those of the globally distributed picocyanobacteria genera Prochlorococcus, Cyanobium and Synechococcus.
- Association of 3-Phenoxybenzoic Acid Exposure during Pregnancy with Maternal Outcomes and Newborn Anthropometric Measures: Results from the IoMum Cohort StudyPublication . Guimarães, Juliana; Bracchi, Isabella; Pinheiro, Cátia; Moreira, Nara Xavier; Coelho, Cláudia Matta; Pestana, Diogo; Prucha, Maria do Carmo; Martins, Cristina; Domingues, Valentina F.; Delerue-Matos, Cristina; Dias, Cláudia C.; Azevedo, Luís Filipe R.; Calhau, Conceição; Leite, João Costa; Ramalho, Carla; Keating, Elisa; Fernandes, Virgínia CruzThe aims of this study were to characterize the exposure of pregnant women living in Portugal to 3-phenoxybenzoic acid (3-PBA) and to evaluate the association of this exposure with maternal outcomes and newborn anthropometric measures. We also aimed to compare exposure in summer with exposure in winter. Pregnant women attending ultrasound scans from April 2018 to April 2019 at a central hospital in Porto, Portugal, were invited to participate. Inclusion criteria were: gestational week between 10 and 13, confirmed fetal vitality, and a signature of informed consent. 3-PBA was measured in spot urine samples by gas chromatography with mass spectrometry (GC-MS). The median 3-PBA concentration was 0.263 (0.167; 0.458) μg/g creatinine (n = 145). 3-PBA excretion was negatively associated with maternal pre-pregnancy body mass index (BMI) (p = 0.049), and it was higher during the summer when compared to winter (p < 0.001). The frequency of fish or yogurt consumption was associated positively with 3-PBA excretion, particularly during the winter (p = 0.002 and p = 0.015, respectively), when environmental exposure is low. Moreover, 3-PBA was associated with levothyroxine use (p = 0.01), a proxy for hypothyroidism, which could be due to a putative 3-PBA—thyroid hormone antagonistic effect. 3-PBA levels were not associated with the anthropometric measures of the newborn. In conclusion, pregnant women living in Portugal are exposed to 3-PBA, particularly during summer, and this exposure may be associated with maternal clinical features.
- Bioactive Lipids of Seaweeds from the Portuguese North Coast: Health Benefits versus Potential ContaminationPublication . Soares, Cristina; Sousa, Sara; Machado, Susana; Vieira, Elsa; Carvalho, Ana P.; Ramalhosa, Maria João; Morais, Simone; Correia, Manuela; Oliva-Teles, MT; Domingues, Valentina; Delerue-Matos, CristinaThe total lipid content and lipidic profile of seaweeds harvested in the North Coast and purchased in Portugal were determined in this paper. The amount of total lipids in the different species of seaweeds varied between 0.7 ± 0.1% (Chondrus crispus) and 3.8 ± 0.6% (Ulva spp.). Regarding the fatty acid content, polyunsaturated fatty acids (PUFA) ranged between 0–35%, with Ulva spp. presenting the highest amount; monounsaturated fatty acids (MUFA) varied between 19 and 67%; and saturated fatty acids (SFA) were predominant in C. crispus (45–78%) and Gracilaria spp. (36–79%). Concerning the nutritional indices, the atherogenicity index (AI) was between 0.4–3.2, the thrombogenicity index (TI) ranged from 0.04 to 1.95, except for Gracilaria spp., which had a TI of 7.6, and the hypocholesterolemic/hypercholesterolemic ratio (HH) values ranged between 0.88–4.21, except for Gracilaria spp., which exhibited values between 0.22–9.26. The n6/n3 ratio was below 1 for most of the species evaluated, except for Ascophyllum nodosum, which presented a higher value, although below 2. Considering the PUFA/SFA ratio, seaweeds presented values between 0.11–1.02. The polycyclic aromatic hydrocarbons (PAHs) and aliphatic hydrocarbons (AHCs) contamination of seaweeds under study was also quantified, the values found being much lower than the maximum levels recommended for foodstuff.
- Cytochrome P450 polymorphisms with impact in cardiovascular drugs metabolisms in European populationsPublication . Morais, Stephanie L.; Gonçalves, Tiago F.C.; Delerue-Matos, Cristina; Ferrreira-Fernandes, Hygor; Pinto, Giovanny R.; Domingues, Valentina F.; Barroso, M. FátimaThe cytochrome P450 (CYP) enzymes constitute a large polymorphic family that play a huge role in the metabolism of endogenous compounds and in the metabolization of 70–80% of all clinically prescribed medications. Among them, the CYP2C9, CYP2C19, CYP2D6 and CYP4F2 genes are of clinical relevance, as they are highly polymorphic and implicated in the metabolism of several drugs. These genetic polymorphisms which induce variability in CYPs expression present qualitative and quantitative differences between ethnic groups and geographic regions. This review aims to evaluate the allele frequencies, genotypic distribution and predicted CYP2C9, CYP2C19, CYP2D6 and CYP4F2 genetic variants in the European countries. Therefore, a PubMed and a Web of Science search from 1989 to 2021 on the data on the polymorphic prevalence among European countries of the CYP2C9, CYP2C19, CYP2D6 and CYP4F2 genes was performed. After excluding the duplicates, a total of 1179 studies were found. The results were structured and presented in accordance with the Preferred Reporting Items for Systematic Reviews and Meta-Analyses (PRISMA) guidelines. The present paper is an overview on the frequency CYP genetic variations, facilitating the prediction of a patient's response to medication and, consequently, enabling the selection of personalized medicine
- The Fatty Acid Profile in Patients with Newly Diagnosed Diabetes: Why It Could Be UnsuspectedPublication . Castro-Correia, C.; Sousa, S.; Norberto, S.; Matos, C.; Domingues, Valentina; Fontoura, M.; Calhau, C.Several studies have shown a link between proinflammatory activity and the presence or deficit of some fatty acids. Inflammation is associated with several diseases including diabetes. Objective. To characterize and compare the fatty acids profiles in children with inaugural type 1 diabetes, diabetic children (at least 1 year after diagnosis), and healthy children. Design. Plasma fatty acids profiles in children with inaugural diabetes, children with noninaugural diabetes, and controls, all of whom were prepubescent with a BMI < 85th percentile, were evaluated. Results. Omega-3 fatty acid levels were higher in recently diagnosed subjects with diabetes than in controls. The ratio of omega-6/omega-3 fatty acids was higher in the control population. Omega-6 fatty acid levels were higher in the nonrecent diabetic subjects than in the children with recently diagnosed diabetes, and the levels were higher in the nonrecent diabetes group compared to the control group. Conclusion. Our findings showed higher levels of alpha-linolenic acid, EPA, and DHA, as well as mono- and polyunsaturated fatty acids, in diabetic children. These findings reinforce the importance of precocious nutritional attention and intervention in the treatment of diabetic children.
- Antibacterial Use of Macroalgae Compounds against Foodborne PathogensPublication . Silva, Aurora; Silva, Sofia A.; Lourenço-Lopes, C.; Jimenez-Lopez, C.; Carpena, M.; Gullón, P.; Fraga-Corral, M.; Domingues, Valentina; Barroso, M. Fátima; Simal-Gandara, J.; Prieto, M. A.The search for food resources is a constant in human history. Nowadays, the search for natural and safe food supplies is of foremost importance. Accordingly, there is a renewed interest in eco-friendly and natural products for substitution of synthetic additives. In addition, microbial contamination of food products during their obtaining and distribution processes is still a sanitary issue, and an important target for the food industry is to avoid food contamination and its related foodborne illnesses. These diseases are fundamentally caused by certain microorganisms listed in this review and classified according to their Gram negative or positive character. Algae have proven to possess high nutritional value and a wide variety of biological properties due to their content in active compounds. Among these capabilities, macroalgae are recognized for having antimicrobial properties. Thus, the present paper revises the actual knowledge of microbial contaminants in the food industry and proposes antimicrobial algal compounds against those pathogenic bacteria responsible for food contamination as valuable molecules for its growth inhibition. The capacity of algae extracts to inhibit some major food pathogen growth was assessed. Moreover, the main applications of these compounds in the food industry were discussed while considering their favorable effects in terms of food safety and quality control
- Assessment of Pyrethroid Pesticides in Topsoils in Northern PortugalPublication . Bragança, Idalina; Lemos, Paulo C.; Delerue-Matos, Cristina; Domingues, Valentina F.Pyrethroid insecticides are emerging contam-inants broadly used for insect pest control in agriculture,veterinary, and domestic applications. Limited informa-tion can be found in literature regarding pyrethroidpesticide soil contamination in playgrounds and agricul-tural areas. The focus of this study was on new findingsrelated to the spatial and seasonal occurrence of pyre-throid pesticide contamination in soils of northern Por-tugal. The soils were tested during summer and winterseasons. Pyrethroid pesticides were not found in the tenplaygrounds sampled during both seasons. For the 18agricultural soil samples tested, deltamethrin was theonly pyrethroid detected, just during the summer sea-son. For those, three of the samples taken were found tobe positive with concentrations between 15.7 and101.7 ng g−1. The results denote the need for monitoringand assessment of pyrethroid pesticide contamination inPortuguese soil. Further research is needed to access the ecological potential impact of pyrethroid pesticides onsoil.
- Occurrence of bisphenol A, estrone, 17b-estradiol and 17a-ethinylestradiol in Portuguese riversPublication . Rocha, Sónia; Domingues, Valentina F.; Pinho, Carina; Fernandes, Virgínia C.; Delerue-Matos, Cristina; Gameiro, P.; Mansilha, CatarinaThis study focused on the occurrence of several EDCs including bisphenol A, estrone (E1), the 17b-estradiol (E2) and 17a- thinylestradiol (EE2) in fourteen rivers of Portugal. Samples analysis revealed a widespread contamination of BPA especially in Ave, Cávado, Douro, Ferro, Sousa and Vizela Rivers. Achieving 98.4 ng/L for the highest concentration. The estrogens achieved above the method quantification limit (MQL) were E1 in Águeda River and E2 in Ave, Lima and Tâmega Rivers. The maximum concentration detected for E1 was 26.9 ng/L. EE2 was detected only below MQL.
- Application of the QuEChERS method for the determination of organochlorine pesticide residues in Brazilian fruit pulps by GC-ECDPublication . Paz, Mário; Correia-Sá, Luísa; Vidal, Carla B.; Becker, Helena; Longhinotti, Elisane; Domingues, Valentina F.; Delerue-Matos, CristinaThe Quick, Easy, Cheap, Effective, Rugged, and Safe (QuEChERS) method was applied to the extraction of 14 organochlorine pesticides (OCPs) residues from commercial fruit pulps available in supermarkets in Fortaleza, Northeastern Brazil. The analyses were carried out by gas chromatography (GC), coupled to an electron-capture detector (ECD), and were confirmed by GC-tandem mass spectrometry (MS). The parameters of the analytical method, such as accuracy, precision, linear range, limits of detection and quantification, were determined for each pesticide. The results showed good linearity (R2 0.9916) and the overall average recoveries were considered satisfactory obtaining values between 69 and 110%, RSD of 2–15 %, except for hexachlorobenzene (HCB) in a¸cai, acerola and guava pulp samples. The OCPs were detected in guava (a–HCH; lindane) and soursop (a, b–HCH isomers) samples. The QuEChERS method and GC–ECD were successfully used to analyze OCPs in commercially available Brazilian fruit pulps and can be applied in routine analytical laboratories.
- Impact of brominated flame retardants on lipid metabolism: An in vitro approachPublication . Maia, Maria Luz; Sousa, Sara; Pestana, Diogo; Faria, Ana; Teixeira, Diana; Delerue-Matos, Cristina; Domingues, Valentina; Calhau, ConceiçãoBrominated flame retardants (BFRs) are chemicals employed to lower the flammability of several objects. These endocrine disruptor chemicals are lipophilic and persistent in the environment. Due to these characteristics some have been restricted or banned by the European Union, and replaced by several new chemicals, the novel BFRs (NBFRs). BFRs are widely detected in human samples, such as adipose tissue and some were linked with altered thyroid hormone levels, liver toxicity, diabetes and metabolic syndrome in humans. However, the disturbance in lipid metabolism caused by BFRs with emphases to NBFRs remains poorly understood. In this study, we used a pre-adipocyte (3T3-L1) cell line and a hepatocyte (HepG2) cell line to investigate the possible lipid metabolism disruption caused by four BFRs: hexabromobenzene (HBB), pentabromotoluene (PBT), 2-ethylhexyl-2,3,4,5-tetrabromobenzoate (TBB) and hexabromocyclododecane (HBCD). For that purpose, proliferation and Oil Red O assays, as well as, medium fatty acids profile evaluation using Gas chromatography and RNA extraction for quantitative RT-PCR assays were performed. We detected a significant reduction in the proliferation of preadipocytes and an increased lipid accumulation during differentiation caused by HBB. This BFR also lead to a significant increased expression of IL-1β and decreased expression of PGC-1α and adiponectin. Nevertheless, PBT, TBB and HBCD show to increase lipid accumulation in hepatocytes. PBT also display a significant increase of PPARγ gene expression. Lipid accumulation in the cells can occur by diverse mechanisms depending on the BFR. These results highlight the importance of endocrine disruptor compounds in obesity etiopathogeny.