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- Extraction optimization of bioactive compounds from Thymus ulgaris L.: comparison of heat-assisted and ultrasound-assisted extractionsPublication . Caleja, Cristina; Pereira, Eliana; Sprea, Rafael M.; Finimundy, Tiane C.; Carocho, Márcio; Amaral, Joana S.; Prieto Lage, Miguel A.; Barros, LillianPlants have been used since ancient times due to their biological action associated mainly with several phytochemicals, including phenolic compounds1. Thymus vulgaris L. is a species described as a potential source of natural molecules with applications in the food industry, but also in the cosmetic and pharmaceutical industry due to its antibacterial, antifungal, and anti-inflammatory effects2. In this sense, the present study aimed to compare extraction systems in terms of phenolic compounds from T. vulgaris through the heat-assisted (HAE) and ultrasound-assisted extraction (UAE) techniques, aiming to improve its potential for industrial applications. For this propose, an extraction optimization was studied using three independent variables, time (t, minutes), solvent (S, % of ethanol), and temperature (T, ºC) or power (P, W), in a three-level Box-Behnken design, analyzing the surface methodology (RSM). The extraction yield and the content in phenolic compounds identified by HPLC-DAD-ESI/MS were the experimental responses applied. The polynomial models were successfully fitted to the experimental data and used to determine the optimal HAE and UAE conditions. Nineteen phenolic compounds were identified, nine of which were phenolic acids (mainly caffeic acid derivatives) and ten flavonoids: flavan-3-ols (catechin derivatives), flavones (quercetin derivatives), flavonols (apigenin and luteolin derivatives) and flavanones (eriodictyol derivatives). The conditions obtained for the optimal extraction of phenolic compounds, that allowed the experimental validation of the predictive model are 3% ethanol (v/v) for 89 minutes at a temperature of 98º C for HAE and 77% ethanol (v/v) for 17 minutes at 207 W for UAE. Extraction optimization is important from an industrial point of view, as it allows obtaining extracts with a high content of bioactive compounds. Considering that the phenolic composition appears in literature as a direct influence on bioactive properties, the optimization processes will allow a better exploitation of extracts, ensuring the greatest cost reduction for the industry.
- Basil and eucalyptus as a source of essential oils with bioactive propertiesPublication . Pereira, Eliana; Caleja, Cristina; Sprea, Rafael M.; Abreu, Rui M.V.; Pires, Tânia C.S.; Amaral, Joana S.; Prieto Lage, Miguel A.; Barros, LillianAromatic and medicinal plants have been used worldwide for culinary purposes aiming to modify, enhance or improve the flavour of foods. In addition, several aromatic plants are also recognized for their empiric use in folk medicine due to their beneficial health effects1. The secondary metabolites of aromatic plants could have diverse applications in industry, and several essential oils have a Generally Recognized as Safe (GRAS) status attributed by the Food and Drug Administration (FDA). Currently, these natural matrices have been characterized by having active antioxidant components in their composition that have a direct impact on food quality and have potential benefits on human health2. In addition, studies focusing on different aromatic plants have suggested the use of their essential oils and some constituents as promising alternatives for obtaining natural preservatives. The present work reports a study on the bioactivity of essential oils obtained from two species of aromatic plants: Ocimum basilicum L. (basil) and Eucalyptus globulus Labill. (eucalyptus). The essential oil was obtained by hydrodistillation using a Clevenger apparatus and volatile compounds were analyzed by GC-MS equipped with DB-5MS fused-silica column. The antimicrobial activity was determined by broth microdilution assay against several Gram-positive and Gram-negative ATCC bacterial strains, and fungi. The bioactive potential was evaluated through several in vitro assays, namely antioxidant activity using two different assays: DPPH (2,2-diphenyl-1- picrylhydrazyl) radical scavenging activity and reducing power; cytotoxic activity using three tumour cell-lines: CaCo (colorectal adenocarcinoma), MCF-7 (breast adenocarcinoma) and NCIH460 (non-small cell lung carcinoma) and a non-tumor cell line of monkey kidney (VERO), by applying the sulforhodamine B assay; anti-inflammatory activity was assessed using RAW 264.7 macrophage cells. In general, the results revealed a auspicious antimicrobial potential of the essential oils against the tested strains, as well as a very promising antioxidant and anti-inflammatory activities. In addition, it was also possible to verify the absence of toxicity of both extracts. Therefore, essential oils extracted from the studied plants can be appealing alternatives to the currently used synthetic additives, with potential application in the food and pharmaceutical industries for their relevant bioactive properties.
- Chemical and bioactive characterization of the aromatic plant Levisticum officinale W.D.J. Koch: a comprehensive studyPublication . Sprea, Rafael M.; Fernandes, Ângela; Calhelha, Ricardo C.; Pereira, Carla; Pires, Tânia C.S.; Alves, Maria José; Canan, Cristiane; Barros, Lillian; Amaral, Joana S.; Ferreira, Isabel C.F.R.Aromatic plants have been used since antiquity as seasoning ingredients to impart unique flavours to foods, and also as folk medicines, and are currently used as a source of several compounds of interest for different industries. Lovage (Levisticum officinale W.J.D. Koch) is an aromatic plant from the Apiaceae family with a strong flavour that has long been used in culinary products, in traditional medicine and by the food industry. Despite its significance and relevance, apart from its composition in volatile compounds, there is a scarcity of information about this plant species. To the best of our knowledge, this study documents for the first time the nutritional value and composition in fatty acids, organic acids and tocopherols of the edible aerial part of lovage, evidencing a low caloric value, a predominance of polyunsaturated fatty acids, mainly α-linolenic acid, oxalic acid as the most abundant organic acid and α-tocopherol as the most abundant vitamin E isoform. The essential oil was mainly characterised by the presence of monoterpenes, showing also a high abundance of phthalides. In addition, a total of 7 phenolic compounds were identified in the decoction and hydroethanolic extracts, which showed interesting antioxidant properties and bacteriostatic activity, particularly against Gram-positive bacteria. Only the decoction showed cytotoxicity against a tumoral cell line (HepG2).
- Caracterização química e propriedades bioativas de resíduos industriais da produção de óleo de noz (Juglans regia L.)Publication . Sprea, Rafael M.; Finimundy, Tiane C.; Pinela, José; Calhelha, Ricardo C.; Pires, Tânia C.S.; Amaral, Joana S.; Prieto Lage, Miguel A.; Barros, LillianAs borras obtidas na produção de óleo de noz podem ser consideradas como um dos principais subprodutos desta indústria, sendo atualmente reaproveitados como fertilizante ou na alimentação animal [1]. Neste sentido, tendo por objetivo final a valorização deste subproduto, este trabalho consistiu na caracterização química e avaliação da bioatividade das borras geradas na produção de óleo de noz. As borras industriais foram analisadas no que respeita o teor em açúcares livres e tocoferóis usando cromatografia líquida acoplada a detetores de índice de refração (HPLC-RI) e de fluorescência (HPLC-FL), respetivamente. Os ácidos gordos foram determinados por cromatografia gasosa com deteção de ionização de chama (GC-FID), os ácidos orgânicos por cromatografia líquida ultrarrápida acoplada a um detetor de díodos (UPLC-DAD) e os compostos fenólicos por HPLC com deteção DAD e espectrometria de massa (HPLC-DAD-ESI-MS/MS). Adicionalmente, avaliou-se a atividade antioxidante e antimicrobiana do extrato hidroetanólico obtido a partir das borras. A atividade antioxidante foi determinada através de três ensaios in vitro (inibição da peroxidação lipídica por substâncias reativas ao ácido tiobarbitúrico (TBARS) em homogeneizados cerebrais, e atividade antioxidante celular (CAA)) e a atividade antimicrobiana pelo método de microdiluição contra um painel de bactérias e fungos. As borras de nozes apresentaram uma predominância em ácidos gordos polinsaturados, sendo o ácido linoleico o maioritário, apresentando um teor superior a 55%. Em relação aos tocoferóis, foram observadas as isoformas α, γ e δ, sendo o γ-tocoferol o composto predominante (89 mg/100 g). Apenas a sacarose foi identificada no que concerne os açucares livres, e o ácido quinico foi o maioritário (1,06 mg/100 g) entre os cinco ácidos orgânicos identificados. No que respeita a composição fenólica do extrato, observou-se uma predominância de derivados da catequina (flavan-3-ois) e taninos hidrolisáveis. O extrato das borras de nozes demonstrou interessante atividade antioxidante, apresentando ótimos valores de EC50 (TBARS: 32,84 g/mL) e % de inibição (CAA: 90%). Contudo, o extrato não apresentou atividade significativa contra as bactérias e fungos testados. Os resultados deste trabalho demonstram o potencial deste resíduo industrial dada a sua elevada atividade antioxidante e composição em nutrientes e compostos bioativos, podendo o mesmo ser futuramente explorado através da sua incorporação em produtos alimentares, agregando valor à cadeia produtiva de óleo de noz.
- Study of aromatic and medicinal plants as potential natural ingredients for the food industryPublication . Sprea, Rafael M.; Caleja, Cristina; Pereira, Eliana; Pinela, José; Kostić, Marina; Soković, Marina; Ferreira, Isabel C.F.R.; Amaral, Joana S.; Barros, LillianConsidering the association of plants consumption and utilization with the treatment of some illnesses and diseases, several aromatic and medicinal plants have been used in traditional and contemporary medicine. This capacity has been proven scientifically and there are numerous studies describing their therapeutic properties in the treatment of inflammatory and cardiovascular disorders, diabetes, among other conditions [1] . The antioxidant and antimicrobial activities have already been studied in a wide variety of plants, which have been shown to contain bioactive molecules effective against pathogenic microorganisms and capable of removing reactive oxygen species formed in cells [2,3]. In this sense, ten aromatic and medicinal plants ( Eucalyptus globulus Labill., Olea europaea L., Melissa officinalis L., Origanum vulgare L., Glycyrrhiza glabra L., Arbutus unedo L., Matricaria recutita L., Thymus vulgaris L., Ocimum vulgare L., and Salvia officinalis L.) were selected to perform an initial screening for the exploration of natural ingredients with bioactive potential. The plant extracts were obtained after ethanolic extraction. The antioxidant activity was evaluated through two in vitro cell-based assays, namely the lipid peroxidation inhibition test (TBARS) and the oxidative hemolysis inhibition test (OxHLIA), and antimicrobial activity was tested by the broth microdilution method, against a panel of bacteria and fungi, selected according to their public health importance. These analyses presented very promising results, showing a high bioactive potential for all plant extracts. In the TBARS assay, E. globulus and O. vulgare stood out with lower EC 50 values, followed by T. vulgaris and S. officinalis . In turn, in the OxHLIA assay, for Δ t 60 min and Δ t 120 min, the excellent antioxidant capacity of S. officinalis and T. vulgaris was also evidenced, respectively. In addition, the evaluation of the antimicrobial activity highlighted the sample of G. glabra , both at the bacterial and fungal levels. Overall, it was possible to prove the great bioactive potential of the E. globulus , O. vulgare , S. officinalis , T. vulgaris and G. glabra extracts, and to highlight them as promising options for exploitation in the food industry.
- Chemical and Bioactive Evaluation of Essential Oils from Edible and Aromatic Mediterranean Lamiaceae PlantsPublication . Sprea, Rafael M.; Caleja, Cristina; Finimundy, Tiane C.; Calhelha, Ricardo C.; Pires, Tânia C.S.P.; Amaral, Joana S.; Prieto Lage, Miguel A.; Ferreira, Isabel C.F.R.; Pereira, Eliana; Barros, LillianThe Lamiaceae family, which includes several well-known aromatic plants, is scientifically relevant due to its essential oils (EOs). In this work, four EOs from Mediterranean species, namely Origanum vulgare L., Rosmarinus officinalis L., Salvia officinalis L., and Thymus vulgaris L., were evaluated for their volatile profiles and the biological activity in vitro to assess their potential use in the food and cosmetic sector. GC/MS analysis revealed dominant compounds, such as carvacrol, thymol, and eucalyptol. Regarding biological action, the samples exhibited antioxidant, cytotoxic, anti-inflammatory, antimicrobial, and antifungal activities, with O. vulgare and T. officinalis standing out. T. vulgaris showed the lowest EC50 in the reducing power assay, and O. vulgare had the lowest EC50 in the DPPH assay. Most EOs also displayed excellent anti-inflammatory responses and antifungal properties, with O. vulgare and T. vulgaris also demonstrating antibacterial activity. All EOs from Mediterranean species showed cytotoxicity against tumoral cell lines. Overall, the selected EOs stood out for their interesting bioactivities, with the obtained results underscoring their potential as natural preservatives and bioactive agents in various industrial applications, including food, pharmaceuticals, and cosmetics.
- Lovage (Levisticum officinale W.D.J. Koch) roots: a source of bioactive compounds towards a circular economyPublication . Sprea, Rafael M.; Fernandes, Ângela; Finimundy, Tiane C.; Pereira, Carla; Alves, Maria José; Calhelha, Ricardo C.; Canan, Cristiane; Barros, Lillian; Amaral, Joana S.; Ferreira, Isabel C.F.R.Lovage (Levisticum officinale W.D.J. Koch) is an aromatic plant from the Apiaceae (Umbelliferae) family used as a condiment in several regions of Europe and also described to have medicinal properties. While the aerial parts are used as foods, the roots are generally discarded. In the past, lovage roots were used in folk medicine for their diuretic, carminative, and spasmolytic properties. Therefore, the exploitation of this undervalued part of the plant can be a source of valuable bioactive compounds for food and/or pharmaceutical industries. Thus, in this study, extracts of different polarity were prepared and studied regarding their chemical composition and bioactive properties. To the best of our knowledge, the composition in phenolic compounds and the volatile profile of the n-hexane extract are reported for the first time. A total of 24 compounds were identified by GC-MS in the n-hexane extract, evidencing a high relative abundance of phthalides. A total of eight phenolic compounds were identified in lovage root extracts (decoction and hydroethanolic extract), with vanillic acid being the major compound. Regarding antioxidant activity, also reported for the first time, decoction and hydroethanolic extract exhibited a high antioxidant capacity in thiobarbituric acid reactive substances (TBARS) (179 ± 11 μg/mL) and in oxidative hemolysis (OxHLIA) assays (510 ± 6 μg/mL), respectively. n-Hexane extract showed relevant anti-proliferative activity against all tumor cell lines tested (GI50, 48-69 μg/mL), despite inhibiting also the growth of a non-tumoral hepatocyte cell line, however, presenting a significantly higher GI50 value (147 μg/mL). This study revealed that lovage root, an agri-food residue, can be a source of valuable bioactive compounds also presenting biological properties that deserve being explored, which could lead to a circular economy for food and/or the pharmaceutical industry.
- TerpenesPublication . Xavier, Virginie; Sprea, Rafael M.; Finimundy, Tiane C.; Heleno, Sandrina A.; Amaral, Joana S.; Barros, Lillian; Ferreira, Isabel C.F.R.Terpenes are the largest and most diverse group of naturally occurring compounds found in plants. They can be classified according to the number of isoprene units, the most common being monoterpenes (C10), sesquiterpenes (C15), diterpenes (C20), and triterpenes (C30). Besides being the principal constituents of essential oils and playing fundamental roles in plants, many terpenes are extensively used in pharmaceutical and industrial applications ranging from flavours to fragrances and medicines. Several studies have already demonstrated the diversity of terpenes’ biological properties, including cancer chemopreventive effects, antimicrobial, antiviral, analgesic, anti-inflammatory, antifungal, antiparasitic, and other activities. This chapter compiles the various terpenes isolated from plants, their sources, biological activities and beneficial health effects, mechanism of action, extraction and applications, and the future perspective for using the terpenes as lead molecules in several areas of the industry.
- Evaluation of the composition in organic acids, vitamin E and phenolic compounds of lovage (Levisticum officinale W.D.J. Koch) rootsPublication . Sprea, Rafael M.; Fernandes, Ângela; Finimundy, Tiane C.; Canan, Cristiane; Barros, Lillian; Amaral, Joana S.; Ferreira, Isabel C.F.R.Since ancient times, several aromatic plants and spices have been used worldwide in traditional medicine, in addition to its common usage for food purposes. Lovage (Levisticum officinale W.D.J. Koch) is an aromatic plant from the Apiaceae (Umbelliferae) family used as a condiment in several regions of Europe, being also described to have medicinal properties. In particular, lovage roots are described as possessing carminative and spasmolytic activity.1 According to the assessment report of the Committee on Herbal Medicinal Products (HMPC) of the European Medicines Agency on Levisticum officinale Koch, radix, this root is known as a medicine since ancient times in Greece, nowadays being authorized as a traditional herbal medicine in several countries of the European Union.2 This report also includes information regarding lovage root chemical composition, referring the presence of different phthalides, coumarines, phenylpropanoids (chlorogenic, caffeic and ferulic acids) and polyacetylenes (falcarindol and falcarinol). Apart from this information, the scientific literature reports mainly the chemical composition of the essential oil of lovage root, with no information being available regarding other bioactive compounds. Therefore, to address this gap, in this work, the organic acids, vitamin E and phenolic compounds of lovage roots were determined. Dried lovage roots were acquired from an herbal shop in Spain. Organic acids were determined by ultra-fast liquid chromatography coupled with a diode-array detector (Shimadzu Corporation, Japan) in the lyophilized sample, which was extracted using a methodology previously described and optimized.3 Tocopherols were determined in the lyophilized sample using a HPLC system coupled to a fluorescence detector as previously described.4 Phenolic compounds were analysed in two different extracts, namely hydroethanolic and decoction, after those being re-dissolved in ethanol/water (80:20, v/v) and water, respectively, to a concentration of 5 mg/mL. The compounds were evaluated using a Dionex Ultimate 3000 UPLC equipped with a quaternary pump and a diode array coupled in-series to an electrospray ionization mass spectrometry detector (LC-DAD-ESI/MSn) operating as previously described.5 The obtained results showed the presence of 3 organic acids in lovage root, namely oxalic (2.23±0.02 g/100 g d.w.), malic (1.48±0.04 g/100 g d.w.) and fumaric (0.007±0.001 g/100 g d.w.) and two tocopherols, α-tocopherol (0.83±0.03 mg/100 g d.w.) and γ -tocopherol (0.48±0.03 g/100 g d.w.). Regarding phenolic compounds’ composition, a total of 9 compounds, including phenolic acids and flavonoids, were identified and quantified, with vanilic acid being the predominant one in both types of extracts. Comparatively to the hydroethanolic extract, the decoction allowed the extraction of a significantly higher amount of total phenolic compounds (24,3±0,5 mg/g extract versus 3.07±0.04 mg/g extract). To our knowledge, this study represents the first report on the organic acids, vitamin E isoforms and phenolic compounds composition in lovage roots.
- Evaluación nutricional y de la capacidade antioxidante de los hongos silvestres comestibles de PatagoniaPublication . Rugolo, Maximiliano; Sprea, Rafael M.; Caleja, Cristina; Dias, Maria Inês; Pinela, José; Barroetaveña, Carolina; Ferreira, Isabel C.F.R.; Barros, LillianLos hongos silvestres comestibles (HSC) constituyen un alimento funcional de fácil aprovechamiento. Su valor culinario y comercial se debe principalmente a sus propiedades organolépticas; cualidades nutricionales y a sus características medicinales. Los bosques de Nothofagus spp.; las plantaciones forestales (dominadas por Pinus y Pseudotsuga) y las praderas de la región Andino Patagónica albergan numerosas especies de hongos con potencial valor alimenticio. En este estudio se cosecharon 24 especies de HSC endémicos y cosmopolitas de Patagonia (pertenecientes a los géneros: Agaricus; Aleurodiscus; Cortinarius; Cyclocybe; Cyttaria; Fistulina; Flammulina; Grifola; Hydropus; Lactarius; Lepista; Leucoagaricus; Lycoperdon; Macrolepiota; Pleurotus; Ramaria; Rizhopogon y Suillus) para analizar su composición química y nutricional y su capacidad antioxidante. Los esporomas fueron liofilizados; molidos y extractados para analizar la composición proximal según métodos AOAC: grasas; carbohidratos; cenizas; proteínas y valor energético. Por otro lado, se realizó la identificación y cuantificación de los ácidos grasos; azúcares; ácidos orgánicos; compuestos fenólicos y ergosterol por diferentes técnicas cromatográficas. La actividad antioxidante de los extractos se evaluó mediante dos pruebas in vitro: el ensayo de inhibición de la peroxidación de lípidos (TBARS) y el ensayo de inhibición de la hemólisis oxidativa (OxHLIA). Los mayores valores de grasas se encontraron en A. vitellinus; C. magellanicus y G. gargal; de proteína en A. campestris y L. nuda; y de energía en C. hariotii; G. gargal y S. luteus. Los extractos más efectivos respecto a la capacidad antioxidante TBARS resultaron los de Ramaria. Disponer de información nutricional y nutracéutica sobre la diversidad natural de hongos comestibles patagónicos ayudará a incorporarlos en una alimentación funcional; que los elija como alimentos seguros; nutritivos y saludables; y a utilizarlos en una micogastronomía identitaria vinculada al desarrollo turístico.
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