The bioactive properties (antioxidant and antitumour activities, and hepatotoxicity) of the infusion and methanolic extracts of Chenopodium ambrosioides L., a plant commonly used in Portuguese folk medicine, were compared. The chemical composition in hydrophilic (sugars, organic acids and phenolic compounds) and lipophilic (fatty acids and tocopherols) fractions were determined. In general, the infusion revealed higher antioxidant activity, while the methanolic extract was the only one showing antitumour effects against colon, cervical and hepatocellular carcinoma cell lines. No toxicity in non-tumour cells was observed either for the infusion or the extract. The studied plant proved to be a good source of natural antioxidants and other bioactive compounds, which may have industrial use. As far as we know, this is the first detailed chemical characterization and bioactivity evaluation of C. ambrosioides methanolic extract and infusion.

The aim of this study was to characterise sweet cherry regarding nutritional composition of the fruits, and individual phytochemicals and bioactive properties of fruits and stems. The chromatographic profiles in sugars, organic acids, fatty acids, tocopherols and phenolic compounds were established. All the preparations (extracts, infusions and decoctions) obtained using stems revealed higher antioxidant potential than the fruits extract, which is certainly related with its higher phenolic compounds (phenolic acids and flavonoids) concentration. The fruits extract was the only one showing antitumor potential, revealing selectivity against HCT-15 (colon carcinoma) (GI50∼74 μg/mL). This could be related with anthocyanins that were only found in fruits and not in stems. None of the preparations have shown hepatotoxicity against normal primary cells. Overall, this study reports innovative results regarding chemical and bioactive properties of sweet cherry stems, and confirmed the nutritional and antioxidant characteristics of their fruits.

The antimicrobial properties of phenolic extracts of Portuguese wild edible mushroom species (Lactarius deliciosus, Sarcodon imbricatus and Tricholoma portentosum) against pathogens were investigated. The minimal inhibitory concentrations (MICs) were evaluated for the entire mushroom, the cap and the stipe, separately; the portion of the mushroom used proved to be influenced in the results obtained, which are directly correlated with the content of total phenols and flavonoids in the extracts. The growth of Grampositive bacteria (Bacillus cereus, B. subtilis,) was well inhibited by these mushrooms, while Escherichia coli (Gramnegative bacteria) was resistant. The study on the antifungal effect of these mushrooms revealed that Candida albicans and Cryptococcus neoformans were differently inhibited for the mushrooms used.

Aromatic plant species of genus Thymus are important medicinal plants, highly recommended due to a range of therapeutic properties of their essential oil (thyme oil): antirheumatic, antiseptic, antispasmodic, antimicrobial, cardiac, carminative, diuretic and expectorant. Oil is also beneficial in boosting the immune system, and helps to fight colds, flu, infectious diseases and chills. It is proved to be a urinary antiseptic, being very helpful for cystitis and urethritis. Scientific validation of traditional uses, and phytochemical and bioactivity evaluation of essential oils from Thymus serpyllum, Thymus algeriensis and Thymus vulgaris was performed. GC/MS analysis revealed thymol as major component of T. algeriensis, T. vulgaris and T.serpyllum, with a contribution of 56.02%, 48.92% and 38.50%, respectively. The three essential oils (EOs) exhibited a significant antimicrobial activity against all the tested strains, T. serpyllum oil being the most potent (MIC 2.5-5 µg/mL, MBC 5-10 µg/mL; MIC 1-2 µg/mL, MFC 2-4 µg/mL). In addition, T. serpyllum oil revealed the highest antioxidant activity in all the assays and was also the most effective one against all the tested cell lines, presenting GI 50 values of 7.02-52.69 µg/mL. Moreover, the EOs did not show any toxicity, at the tested concentrations (<400 µg/mL), for porcine liver primary cell culture. In addition to their traditional use in food and cosmetics, the great potential of the tested Thymus essential oils for application in oral disease and anticancer treatments, encourage further investigation.

A B S T R A C TThe bio-residues resulting from the wine industry (grape pomace made up of skins, seeds and stems) are often undervalued but constitute a potential source of bioactive phenolic compounds that can be applied in several industries. In this context, the aim of the present study was to evaluate the phenolic profile of Vitis vinifera L. grape pomace (skins, seeds and their mixture), and correlate them with its antioxidant, cytotoxic and antibacterial activities. The seeds showed the highest amount of phenolic compounds and also the highest antioxidant, cytotoxic and antibacterial activities. The skins revealed the highest levels of anthocyanins and pcoumaric acid hexoside. Strong correlations were observed between the presence of phenolic compounds and all the bioactivities studied. These by-products are good sources of phenolic compounds with high antioxidant and antibacterial activity, and also presenting a moderate cytotoxicity activity. These added-value by-products have great applicability in food, pharmaceutical and cosmetic industries.

A B S T R A C TThe edible flowers are widely used, but there is still a lot to be done in relation to its bioactive potential and its correlation with the presence of phenolic compounds. The aim of this study was determined the individual phenolic profile in the hydromethanolic extracts and infusion preparations of four different flower samples (Dahlia mignon, Rosa damascena 'Alexandria' and R. gallica 'Francesa' draft in R. canina, Calendula officinalis L., and Centaurea cyanus L.) and their bioactive potential (antioxidant, antiproliferative, and antibacterial capacity). All the studied flowers presented different profiles regarding their phenolic composition and revealed biological potential. The bioactive potential of the studied flowers was moderate, the hydromethanolic extracts of rose petals showed the best results for antioxidant and antibacterial assays, while the antiproliferative properties were only present in some of the tested cell lines, for the hydromethanolic extracts, in which dahlia and rose showed the best results. These results demonstrate that edible flowers can be used as a source of phenolic compounds with bioactive potential, which can be applied in the food sector, as foods and as sources natural ingredients.

a b s t r a c t Hepatocellular carcinoma (HCC) is a highly complex cancer, resistant to commonly used treatments and new therapeutic agents are urgently needed. A total of thirty-two thieno[3,2-b]pyridine derivatives of two series: methyl 3-amino-6-(hetero)arylthieno[3,2-b]pyridine-2-carboxylates (1ae1t) and methyl 3-amino-6-[(hetero)arylethynyl]thieno[3,2-b]pyridine-2-carboxylates (2ae2n), previously prepared by some of us, were evaluated as new potential anti-HCC agents by studying their in vitro cell growth inhibition on human HepG2 cells and hepatotoxicity using a porcine liver primary cell culture (PLP1). The presence of amino groups linked to a benzene moiety emerges as the key element for the anti-HCC activity. The methyl 3-amino-6-[(3-aminophenyl)ethynyl]thieno[3,2-b]pyridine-2-carboxylate (2f) is the most potent compound presenting GI50 values on HepG2 cells of 1.2 mM compared to 2.9 mM of the positive control ellipticine, with no observed hepatotoxicity (PLP1 GI50 > 125 mM against 3.3 mM of ellipticine). Moreover this compound changes the cell cycle profile of the HepG2 cells, causing a decrease in the % of cells in the S phase and a cell cycle arrest in the G2/M phase. QSAR studies were also per-formed and the correlations obtained using molecular and 1D descriptors revealed the importance of the presence of amino groups and hydrogen bond donors for anti-HCC activity, and hydrogen bond acceptors for hepatotoxicity. The best correlations were obtained with 3D descriptors belonging to different subcategories for anti-HCC activity and hepatotoxicity, respectively. These results point to different molecular mechanisms of action of the compounds in anti-HCC activity and hepatotoxicity. This work presents some promising thieno[3,2-b]pyridine derivatives for potential use in the therapy of HCC. These compounds can also be used as scaffolds for further synthesis of more potent analogs.

Roman chamomile, Chamaemelum nobile L. (Asteraceae), has been used for medicinal applications, mainly through oral dosage forms (decoctions and infusions). Herein, the nutritional characterization of C. nobile was performed, and herbal material and its decoction and infusion were submitted to an analysis of phytochemicals and bioactivity evaluation. The antioxidant activity was determined by free radicals scavenging activity, reducing power and inhibition of lipid peroxidation, the antitumour potential was tested in human tumour cell lines (breast, lung, colon, cervical and hepatocellular carcinomas), and the hepatotoxicity was evaluated using a porcine liver primary cell culture. C. nobile proved to be an equilibrated valuable herb rich in carbohydrates and proteins, and poor in fat, providing tocopherols, carotenoids and essential fatty acids (C18:2n6 and C18:3n3). Moreover, the herb and its infusion are a source of phenolic compounds (flavonoids such as flavonols and flavones, phenolic acids and derivatives) and organic acids (oxalic, quinic, malic, citric and fumaric acids) that showed antioxidant and antitumour activities, without hepatotoxicity. The most abundant compounds in the plant extract and infusion were 5-O-caffeoylquinic acid and an apigenin derivative. These, as also other bioactive compounds are affected in C. nobile decoction, leading to a lower antioxidant potential and absence of antitumour potential. The plant bioactivity could be explored in the medicine, food, and cosmetic industries.