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Sesquiterpene lactones (SL), characterized by their high prevalence in the Asteraceae family, are one of the major groups of secondary metabolites found in plants. Researchers from distinct research fields, including pharmacology, medicine, and agriculture, are interested in their biological potential. With new SL discovered in the last years, new biological activities have been tested, different action mechanisms (synergistic and/or antagonistic effects), as well as molecular structure–activity relationships described. The review identifies the main sesquiterpene lactones with interconnections between immune responses and anti-inflammatory actions, within different cellular models as well in in vivo studies. Bioaccessibility and bioavailability, as well as molecular structure–activity relationships are addressed. Additionally, plant metabolic engineering, and the impact of sesquiterpene lactone extraction methodologies are presented, with the perspective of biological activity enhancement. Sesquiterpene lactones derivatives are also addressed. This review summarizes the current knowledge regarding the therapeutic potential of sesquiterpene lactones within immune and inflammatory activities, highlighting trends and opportunities for their pharmaceutical/clinical use.

Zizyphus lotus L. is a perennial shrub particularly used in Algerian folk medicine, but little is known concerning the lipophilic compounds in the most frequently used parts, namely, root bark, pulp, leaves and seeds, which are associated with health benefits. In this vein, the lipophilic fractions of these morphological parts of Z. lotus from Morocco were studied by gas chromatography–mass spectrometry (GC–MS), and their antiproliferative and antimicrobial activities were evaluated. GC–MS analysis allowed the identification and quantification of 99 lipophilic compounds, including fatty acids, long-chain aliphatic alcohols, pentacyclic triterpenic compounds, sterols, monoglycerides, aromatic compounds and other minor components. Lipophilic extracts of pulp, leaves and seeds were revealed to be mainly composed of fatty acids, representing 54.3–88.6% of the total compounds detected. The leaves and seeds were particularly rich in unsaturated fatty acids, namely, (9Z,12Z)-octadeca-9,12-dienoic acid (2431 mg kg−1 of dry weight) and (9Z)-octadec-9-enoic acid (6255 mg kg−1 of dry weight). In contrast, root bark contained a high content of pentacyclic triterpenic compounds, particularly betulinic acid, accounting for 9838 mg kg−1 of dry weight. Root bark extract showed promising antiproliferative activity against a triple-negative breast cancer cell line, MDA-MB-231, with a half-maximal inhibitory concentration (IC50) = 4.23 ± 0.18 µg mL−1 of extract. Leaf extract displayed interesting antimicrobial activity against Escherichia coli, methicillin-sensitive Staphylococcus aureus and Staphylococcus epidermis, presenting minimum inhibitory concentration (MIC) values from 1024 to 2048 µg mL−1 of extract. Our results demonstrate that Zizyphus lotus L. is a source of promising bioactive components, which can be exploited as natural ingredients in pharmaceutical formulations.

Cynara cardunculus L. is a cardoon species native to the Mediterranean region, which is composed of three botanical taxa, each having distinct biological characteristics. The aim of this study was to examine wild populations of C . cardunculus established in Portugal, in order to determine their genetic diversity, geographic distribution, and population structure. Based on SSR markers, 121 individuals of C . cardunculus from 17 wild populations of the Portuguese Alentejo region were identified and analysed. Ten SSRs were found to be efficient markers in the genetic diversity analysis. The total number of alleles ranged from 9 to 17 per locus. The expected and observed means in heterozygosity, by population analysed, were 0.591 and 0.577, respectively. The wild population exhibited a high level of genetic diversity at the species level. The highest proportion of genetic variation was identified within a geographic group, while variation was lower among groups. Geographic areas having highest genetic diversity were identified in Alvito, Herdade da Abóboda, Herdade da Revilheira and Herdade de São Romão populations. Moreover, significant genetic differentiation existed between wild populations from North-Alentejo geographic locations (Arraiolos, Évora, Monte da Chaminé) and Centro Hortofrutícola, compared with other populations. This study reports genetic diversity among a representative number of wild populations and genotypes of C . cardunculus from Portugal. These results will provide valuable information towards future management of C . cardunculus germplasm.

Plant-derived pentacyclic triterpenic acids (TAs) have gained increasing attention due to their multiple biological activities. Betulinic acid (BA) and ursolic acid (UA) modulate diverse pathways in carcinogenesis, offering increased changes of success in refractory cancers, such as triple negative breast cancer (TNBC). The present work aimed to assess the metabolic effects of BA and UA in MDA-MB-231 breast cancer cells (TNBC model), as well as in MCF-10A non-cancer breast epithelial cells, with a view to unveiling the involvement of metabolic reprogramming in cellular responses to these TAs. Cell viability and cell cycle analyses were followed by assessment of changes in the cells exo- and endometabolome through 1H NMR analysis of cell culture medium supernatants, aqueous and organic cell extracts. In MDA-MB-231 cells, BA was suggested to induce a transient upregulation of glucose consumption and glycolytic conversion, tricarboxylic acid (TCA) cycle intensification, and hydrolysis of neutral lipids, while UA effects were much less pronounced. In MCF-10A cells, boosting of glucose metabolism by the two TAs was accompanied by diversion of glycolytic intermediates to the hexosamine biosynthetic pathway (HBP) and the synthesis of neutral lipids, possibly stored in detoxifying lipid droplets. Additionally, breast epithelial cells intensified pyruvate consumption and TCA cycle activity, possibly to compensate for oxidative impairment of pyruvate glycolytic production. This study provided novel insights into the metabolic effects of BA and UA in cancer and non-cancer breast cells, thus improving current understanding of the action of these compounds at the molecular level.

Macroalgae have been seen as an alternative source of molecules with promising bioactivities to use in the prevention and treatment of current lifestyle diseases. In this vein, the lipophilic fraction of short-term (three weeks) cultivated Bifurcaria bifurcata was characterized in detail by gas chromatography–mass spectrometry (GC-MS). B. bifurcata dichloromethane extract was composed mainly by diterpenes (1892.78 ± 133.97 mg kg−1 dry weight (DW)), followed by fatty acids, both saturated (550.35 ± 15.67 mg kg−1 DW) and unsaturated (397.06 ± 18.44 mg kg−1 DW). Considerable amounts of sterols, namely fucosterol (317.68 ± 26.11 mg kg−1 DW) were also found. In vitro tests demonstrated that the B. bifurcata lipophilic extract show antioxidant, anti-inflammatory and antibacterial activities (against both Gram-positive and Gram-negative bacteria), using low extract concentrations (in the order of µg mL−1). Enhancement of antibiotic activity of drug families of major clinical importance was observed by the use of B. bifurcata extract. This enhancement of antibiotic activity depends on the microbial strain and on the antibiotic. This work represents the first detailed phytochemical study of the lipophilic extract of B. bifurcata and is, therefore, an important contribution for the valorization of B. bifurcata macroalgae, with promising applications in functional foods, nutraceutical, cosmetic and biomedical fields.

The establishment of operation protocols for olive oil (OO) extraction at non-industrial scale is crucial for research purposes. Thus, the present study proposes a simple and cost-effective method for OO extraction at the laboratory scale (LS) level. To validate the proposed methodology, industrial OO extraction (IS) was performed in parallel, using the same cultivars ‘Galega vulgar’ (GV), ‘Cobrançosa’ (COB) and ‘Arbequina’ (ARB) collected from the same orchards, within the same period. Obtained results showed highest extractability for COB and ARB, of about 53%, while GAL showed 50%. All produced OO showed values lower than the regulated limits for the physicochemical parameters (acidity, K232, K268 and ΔK), classifying them as extra virgin OO (EVOO). Highest total phenolic content was observed for COB, with no significant differences (p-value > 0.05) between extraction methods. Regarding fatty acid composition, oleic acid (C18:1) showed the lowest percentage for ARB, with about 66% and 68%, for LS and IS, respectively, and the highest for GV with about 72% for both LS and IS. Furthermore, all samples from both extraction methods were compared to the European Community Regulation, with fatty acid composition within the regulated levels for EVOO. This work showed promising results regarding extraction yields and OO extractability, as well as its quality parameters.

Sesquiterpene lactones (SLs) are compounds that are highly produced in Cynara cardunculus leaves, known for their phytotoxic activity. This study aims to assess SL-enriched fractions’ (cynaropicrin, aguerin B, and grosheimin) phytotoxic potentials and putative modes of action, compared to an initial extract, using two approaches: first, against a panel of nine weed species in pre-emergence, and then on Portulaca oleracea L.’s post-emergency stage. The SL-enriched fractions demonstrated greater phytotoxic activity when compared with the C. cardunculus leaf initial extract. The SL-enriched fractions had higher activity at root growth inhibition over the panel tested, doubling the activity in five of them at 800 ppm. Regarding the post-emergence bioassay, the SL-enriched fractions had a higher influence on the plants’ growth inhibition (67% at 800 ppm). The SL-effects on the plants’ metabolisms were evidenced. The total chlorophyll content was reduced by 65% at 800 ppm. Oxidative stress induction was observed because of the enhancement in MDA levels at 800 ppm compared to control (52%) and the decrease in SOD-specific activity from 4.20 U/mg protein (400 ppm) to 1.74 U/mg protein (800 ppm). The phytotoxic effects of the SL-enriched fractions suggest that they could be used for a future bioherbicide development.

The phenolic composition of olive fruits represents a vast and unique source of health beneficial molecules due to the presence of specific phenolic compounds (PCs), such as verbascoside (VERB), oleuropein (OLE) and its derivative molecules. Despite of being some of the most critical compounds regarding olive oil quality, these PCs are mostly abundant in olive fruits and leafs due to their hydrophilic nature. In olives, the phenolic profile suffers a deep and constant change along fruit ripening being the phenolic alcohols, such as hydroxytyrosol (HT), mainly formed by OLE, and/or OLE aglycone molecules degradation. The present work aims to study the maturation evolution of olive fruits from two major traditional Portuguese cultivars, ‘Galega Vulgar’ and ‘Cobrançosa’, in regard to their specific phenolic profile, as well as caliber (C), moisture (H), fat content in dry matter (OPDW) and maturity index (MI). Results show that both cultivars present distinct phenolic profiles along their ripening, with ‘Galega Vulgar’ reaching a high MI and OPDW at a much earlier ripening stage (S3), in agreement with the moment when a maximum OLE accumulation was registered. On the other hand, ‘Cobrançosa’ cultivar reached its higher MI and OPDW at S6 (harvest period), coinciding also with high OLE concentrations. MI may be used as a prediction tool for ’Galega Vulgar’ optimal harvesting time evaluation, associated with higher OLE and VERB concentrations, which will confer an additional protection towards diseases, that normally affect olive orchards.

The objective of this work is to evaluate the influence of pomegranate peel extract (PPE) in the behavior of breast cell lines (epithelial and tumor type) and related oxidative metabolism. Fruit-based functional foods have been the target of increasing scientific research for their physiological and pathophysiological properties. Pomegranate (Punica granatum) is a suitable example with both prophylactic and medicinal effects. MCF-7 cell line from tumor breast carcinoma, and MCF-10A cell line from normal epithelial mammary gland were used and subjected to different concentrations of PPE, ranging from 1 to 5 mM of gallic acid equivalents (GAE). Viability, proliferation, mobility, and cytotoxicity assays were performed along with the quantification of antioxidant enzymes, namely, catalase, superoxide dismutase (SOD) and reduced (GSH) and oxidized (GSSG) glutathione. We observed a decrease in viability and proliferation of MCF-7 cells, at higher concentrations of PPE, with no influence in epithelial cells. Interestingly, in a concentration-dependent manner, PPE triggered a significant decrease in migration on both cell lines, with a more pronounced effect in breast cancer cell line. Regarding antioxidant enzyme activity, on tumor cells higher concentrations of PPE decreased catalase activity and significantly increased SOD activity. Regarding GSH and GSSG, we observed different expression levels between MCF-7 and MCF-10A, with MCF-7 presenting lower levels compared to MCF-10A. GSH/GSSG ratio was notably higher in MCF-7 at 5 mM GAE. PPE exhibits anti-tumor effects without significantly affecting normal epithelial cells. Our work strengthens the potential antitumoral effect of PPE by reducing MCF-7 cell viability and proliferation through the imbalance of antioxidant enzymes.

Cistus ladanifer (rockrose) is a perennial shrub quite abundant in the Mediterranean region, and it is a rich source in secondary compounds such as condensed tannins (CTs). Condensed tannins from C. ladanifer were able to change the ruminal biohydrogenation (BH), increasing the t11–18:1 and c9,t11–18:2 production. However, the adequate conditions of the C. ladanifer CTs used to optimize the production of t11–18:1 and c9,t11–18:2 is not yet known. Thus, we tested the effect of increasing the doses of C. ladanifer CT extract (0, 25, 50, 75 and 100 g/kg dry matter (DM)) on in vitro rumen BH. Five in vitro batch incubations replicates were conducted using an oil supplemented high-concentrate substrate, incubated for 24 h with 6 mL of buffered ruminal fluid. Volatile fatty acids (VFAs) and long chain fatty acids (FA) were analyzed at 0 h and 24 h, and BH of c9–18:1, c9, c12–18:2 and c9, c12, c15–18:3, and BH products yield were computed. Increasing doses of C. ladanifer CTs led to a moderate linear decrease (p < 0.001) of the VFA production (a reduction of 27% with the highest dose compared to control). The disappearance of c9–18:1 and c9,c12–18:2 as well as the production of t11–18:1 and c9, t11:18:2 was not affected by increasing doses of C. ladanifer CTs, and only the disappearance of c9, c12, c15–18:3 suffered a mild linear decrease (a reduction of 24% with the highest dose compared to control). Nevertheless, increasing the C. ladanifer CT dose led to a strong depression of microbial odd and branched fatty acids and of dimethyl acetals production (less than 65% with the highest dose compared to control), which indicates that microbial growth was more inhibited than fermentative and biohydrogenation activities, in a possible adaptative response of microbial population to stress induced to CTs and polyunsaturated fatty acids. The ability of C. ladanifer to modulate the ruminal BH was not verified in the current in vitro experimental conditions, emphasizing the inconsistent BH response to CTs and highlighting the need to continue seeking the optimal conditions for using CTs to improve the fatty acid profile of ruminant fat.