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Research Project
Associated Laboratory for Green Chemistry - Clean Technologies and Processes
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Transition Metal‐Catalyzed Transformations of Chalcones
Publication . Santos, Clementina M.M.; Silva, Artur
Chalcones are a class of naturally occurring flavonoid compounds associated to a
variety of biological and pharmacological properties. Several reviews have been published
describing the synthesis and biological properties of a vast array of analogues. However, overviews
on the reactivity of chalcones has only been explored in a few accounts. To fill this gap, a
systematic survey on the most recent developments in the transition metal-catalyzed transformation
of chalcones was performed. The chemistry of copper, palladium, zinc, iron,
manganese, nickel, ruthenium, cobalt, rhodium, iridium, silver, indium, gold, titanium,
platinum, among others, as versatile catalysts will be highlighted, covering the literature from
year 2000 to 2023, in more than 380 publications.
Detailed Phytochemical Composition, Cyto-/Hepatotoxicity, and Antioxidant/Anti-Inflammatory Profile of Moroccan Spices: A Study on Coriander, Caraway, and Mystical Cumin
Publication . Bouzaid, Hiba; Espírito Santo, Liliana; Ferreira, Diana M.; Machado, Susana; Costa, Anabela S.G.; Dias, Maria Inês; Calhelha, Ricardo C.; Barros, Lillian; Chater, Oumaima; Rodi, Youssef Kandri; Errachidi, Faouzi; Chahdi, Fouad Ouazzani; Oliveira, Beatriz; Alves, Rita C.
Coriander, caraway, and mystical cumin are famous for their aromatic properties and
widely used in Moroccan cuisine. The nutritional/phytochemical composition of their seeds (used
for food flavoring and preservation) were compared. Their antioxidant, anti-inflammatory, cytotoxic
and hepatotoxic effects were also explored. The fat content was similar among the samples (13%),
with monounsaturated fatty acids being predominant. The coriander and mystical cumin seeds
were extremely rich in C18:1n9c (81 and 85%, respectively) while, in the caraway, C18:1n12 (25%)
was found together with C18:1n9c (32%). The caraway seeds also presented a higher proportion
of C18:2n6c (34%) than the other seeds (13 and 8%, correspondingly). γ-Tocotrienol was the major
vitamin E form in all the samples. The caraway seeds contained double the amount of protein
(~18%) compared to the other seeds (~8%) but, qualitatively, the amino acid profiles among all
seeds were similar. The seeds were also rich in dietary fiber (40–53%); however, differences were
found in their fiber profiles. Caraway showed the highest antioxidant profile and anti-inflammatory
activity and an LC-DAD-ESI/MSn analysis revealed great differences in the phenolic profiles of the
samples. Cytotoxicity (NCI-H460, AGS, MCF-7, and CaCo2) and hepatotoxicity (RAW264.7) were
not observed. In sum, besides their flavoring/preservation properties, these seeds are also relevant
source of bioactive compounds with health-promoting activities.
Characterization of Phenolic Compounds of Arnica montana Conventional Extracts
Publication . Garcia-Oliveira, Paula; Chamorro, Franklin; Donn, Pauline; Garcia-Perez, Pascual; Seyyedi-Mansour, Sepidar; Silva, Aurora; Echave Álvarez, Javier; Simal-Gandara, Jesus; Cassani, Lucia; Prieto Lage, Miguel A.
Arnica montana L. (Asteraceae family) is a plant commonly used in traditional medicine, and several reports have characterized this plant’s bioactivities, especially its phenolic compounds. These compounds are well known for their numerous beneficial biological properties. Consequently, industry stakeholders from the feed, food, cosmetic, and pharmaceutical sectors are seeking extracts rich in phenolic compounds, which could be interesting for the development of bio-based applications. The objective of the present study was to characterize the phenolic profile of this species to lay the groundwork for further optimization studies to obtain the highest amount of phenolic compounds. Therefore, A. montana was extracted with an ethanol/water ratio of 80:20 (v/v) at room temperature for 1 h, and phenolic compounds were identified and quantified through UPLC (HPLC Dionex Ultimate 3000) with a mass detector (TSQ Quantis). In the extract, phenolics belonging to different groups were identified, namely eriodictyol-O-glucuronide (flavanone), hispidulin and luteolin (flavones), kaempferol and 6-methoxykaempferol, (flavonols), p-coumaric, feruloylquinic, caffeoylquinic, and dicaffeoylquinic isomers (hydroxycinnamic acids). However, only four of them could be quantified: kaempferol and the three hydroxycinnamic acids. The total phenolic content (mg/g of dry sample) was estimated to be 27.34 mg/g, with the most prevalent compounds being the dicaffeoylquinic acids (accounting for 79.5% of the total phenolics). It has been demonstrated that dicaffeoylquinic acids present anti-inflammatory and antioxidant activities, which have been linked to several beneficial effects. Thus, obtaining phenolic-rich extracts of A. montana may allow us to exploit this plant’s significant biological properties, and it could be a new ingredient for developing new applications in the nutraceutical, cosmetic, and/or pharmaceutical industries.
Firefighters’ Occupational Exposure in Preparation for Wildfire Season: Addressing Biological Impact
Publication . Esteves, Filipa; Slezakova, Klara; Madureira, Joana; Vaz, Josiana A.; Fernandes, Adília; Morais, Simone; Pereira, Maria do Carmo; Teixeira, João Paulo Fernandes; Costa, Solange
The characterization of wildland firefighters' occupational exposure must consider different exposures, including those at the fire station. The present study aimed to characterize the occupational exposure of 172 Northern Portuguese wildland firefighters in fire stations during the pre-wildfire season of 2021. The biological impact of estimated inhaled doses of PM10 and PM2.5 (indoor/outdoor) was accessed through a buccal micronucleus cytome (BMCyt) assay in exfoliated buccal cells of a subgroup of 80 firefighters. No significant association was found between estimated inhaled doses of PM10 and PM2.5 (mean 1.73 +/- 0.43 mu g kg-1 and 0.53 +/- 0.21 mu g kg-1, respectively) and biological endpoints. However, increased frequencies of cell death parameters were found among subjects of the Permanent Intervention Teams (full-time firefighters). The intake of nutritional supplements was associated with a significant decrease in micronucleus frequencies (i.e., DNA damage or chromosome breakage). In addition, our findings showed a significantly increased frequency of cell death endpoints (i.e., nuclear fragmentation) with coffee consumption, while daily consumption of vegetables significantly decreased it (i.e., nuclear shrinkage). Our results provide data on the occupational exposure of wildland firefighters while working in fire stations during the pre-wildfire season, providing the essential baseline for further studies throughout the wildfire season.
Effects of Summer Water Deficit Stress on Olive Fruits and Oil Quality
Publication . Araújo, Márcia; Rodrigues, Nuno; Santos, Conceição; Pinto, Diana; Pereira, J.A.; Silva, Artur; Dias, Maria Celeste
The Mediterranean basin is the leading worldwide region for olive production. Extreme
weather is increasingly frequent in this region, and how these climate extremes will affect olive
products and quality remains unknown. We aim to study the effects of the water deficit stress, which
occurred in the summer of 2017, on olive fruit and oil quality from a 30-year-old orchard. Fruits from
olive trees standing on (i) one hydrated and (ii) one dry area of an orchard at the north of Portugal
were harvested. Fruits’ water content, oil yield and quality, fruit carbohydrates, and fruit and oil
phenolic metabolite profiles were analyzed. Fruits from the dry area presented low water availability
and increased carbohydrates, oleuropein, oleoside, and elenolic acid glucoside abundance. Oil yield
was lower in the dry area, but the abundance of oleacein increased, together with traits of some
sensory sensations. Climate stress events can reduce oil yield but stimulate the accumulation of
bioactive compounds that improve oil quality and nutritional value.
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Funding agency
Fundação para a Ciência e a Tecnologia
Funding programme
6817 - DCRRNI ID
Funding Award Number
LA/P/0008/2020