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- Antileishmanial activity of meroditerpenoids from the macroalgae Cystoseira baccataPublication . Sousa, Carolina Bruno de; Gangadhar, Katkam N.; Morais, Thiago R.; Conserva, Geanne A. A.; Vizetto-Duarte, C; Pereira, H.; Laurenti, Marcia D.; Campino, Lenea; Levy, Debora; Uemi, Miriam; Barreira, Luísa; Custódio, L.; Passero, Luiz Felipe D.; Lago, Joao Henrique G.; Varela, JoãoThe development of novel drugs for the treatment of leishmaniases continues to be crucial to overcome the severe impacts of these diseases on human and animal health. Several bioactivities have been described in extracts from macroalgae belonging to the Cystoseira genus. However, none of the studies has reported the chemical compounds responsible for the antileishmanial activity observed upon incubation of the parasite with the aforementioned extracts. Thus, this work aimed to isolate and characterize the molecules present in a hexane extract of Cystoseira baccata that was found to be bioactive against Leishmania infantum in a previous screening effort. A bioactivity-guided fractionation of the C. baccata extract was carried out and the inhibitory potential of the isolated compounds was evaluated via the MIT assay against promastigotes and murine macrophages as well as direct counting against intracellular amastigotes. Moreover, the promastigote ultrastructure, DNA fragmentation and changes in the mitochondrial potential were assessed to unravel their mechanism of action. In this process, two antileishmanial meroditerpenoids, (3R)- and (3S)-tetraprenyltoluquinol (1a/1b) and (3R)- and (3S)-tetraprenyltoluquinone (2a/2b), were isolated. Compounds 1 and 2 inhibited the growth of the L. infantum promastigotes (IC50 = 44.9 +/- 4.3 and 94.4 +/- 10.1 mu M, respectively), inducing cytoplasmic vacuolization and the presence of coiled multilamellar structures in mitochondria as well as an intense disruption of the mitochondrial membrane potential. Compound 1 decreased the intracellular infection index (IC50 = 25.0 +/- 4.1 mu M), while compound 2 eliminated 50% of the intracellular amastigotes at a concentration > 88.0 mu M. This work identified compound 2 as a novel metabolite and compound 1 as a biochemical isolated from Cystoseira algae displaying antileishmanial activity. Compound 1 can thus be an interesting scaffold for the development of novel chemotherapeutic molecules for canine and human visceral leishmaniases studies. This work reinforces the evidence of the marine environment as source of novel molecules. (C) 2017 Elsevier Inc. All rights reserved.
- Maritime halophyte species from southern Portugal as sources of bioactive moleculesPublication . Rodrigues, Maria Joao; Gangadhar, Katkam N.; Vizetto-Duarte, C; Wubshet, Sileshi G.; Nyberg, Nils T.; Barreira, Luísa; J. C. or Varela J. or Varela J.C.S., Varela; Custodio, LuisaExtracts of five halophytes from southern Portugal (Arthrocnemum macrostachyum, Mesembryanthemum edule, Juncus acutus, Plantago coronopus and Halimione portulacoides), were studied for antioxidant, anti-inflammatory and in vitro antitumor properties. The most active extracts towards the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical were the methanol extracts of M. edule (IC50 = 0.1 mg/mL) and J. acutus (IC50 = 0.4 mg/mL), and the ether extracts of J. acutus (IC50 = 0.2 mg/mL) and A. macrostachyum (IC50 = 0.3 mg/mL). The highest radical scavenging activity (RSA) against the 2,2-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) radical was obtained in the ether extract of J. acutus (IC50 = 0.4 mg/mL) and H. portulacoides (IC50 = 0.9 mg/mL). The maximum total phenolic content (TPC) was found in the methanol extract of M. edule (147 mg gallic acid equivalents (GAE)/g) and in the ether extract of J. acutus (94 mg GAE/g). Significant decreases in nitric oxide (NO) production were observed after incubation of macrophages with lipopolysaccharide (LPS) and the chloroform extract of H. portulacoides (IC50 = 109 mu g/mL) and the hexane extract of P. coronopus (IC50 = 98.0 mu g/mL). High in vitro cytotoxic activity and selectivity was obtained with the ether extract of J. acutus. Juncunol was identified as the active compound and for the first time was shown to display selective in vitro cytotoxicity towards various human cancer cells.
- Proximate biochemical composition and mineral content of edible species from the genus Cystoseira in PortugalPublication . Vizetto-Duarte, C; Custódio, Luísa; Barreira, Luísa; da Silva, Manuela Moreira; Rauter, Amelia P.; Albericio, Fernando; Varela, J.Macroalgae are valuable resources for human consumption in many countries. This work reports for the first time a comparative evaluation of the nutritional properties of five edible macroalgae from the genus Cystoseira, namely C. humilis, C. tamariscifolia, C. nodicaulis, C. compressa and C. baccata. For this purpose, their proximate composition was determined in terms of moisture, ash, and total contents of protein, lipids, carbohydrates and mineral profile. Cystoseira tamariscifolia and C. baccata were the species that in general had the higher ash, protein and lipid contents, while the highest levels of moisture and total carbohydrates were detected in C. nodicaulis and C. compressa. Cystoseira species had also high amounts of minerals, especially of potassium, calcium and iron, and a favorable Na/K ratio. The present study shows that Cystoseira has a balanced nutritional composition, suitable for human consumption, and that its intake can contribute to a healthy and well-balanced diet.
- A comparative evaluation of biological activities and bioactive compounds of the seagrasses Zostera marina and Zostera noltei from southern PortugalPublication . Custódio, Luísa; Laukaityte, Simona; Engelen, Aschwin; Rodrigues, Maria Joao; Pereira, Hugo; Vizetto-Duarte, C; Barreira, Luísa; Rodriguez, Hortensia; Albericio, Fernando; Varela, JoãoThis work assessed the antioxidant potential, acetylcholinesterase (AChE) inhibition and the in vitro cytotoxic activity of extracts of the seagrasses Zostera marina and Zostera noltei collected from southern Portugal. The total phenolic contents (TPCs), the rosmarinic acid (RA) concentration (HPLC/DAD) and the fatty acid (FA) profile (GC/MS) are also described. Z. marina had the highest TPC, radical scavenging activity against DPPH radicals and copper chelating activity. Z. noltei had metal chelation capacity to copper and iron ions. None of the species was able to inhibit AChE. Both seagrasses had high levels of polyunsaturated FAs. Z. marina significantly and selectively reduced the viability of tumorous neuronal cells. Z. noltei was highly toxic for the three cell lines tested and was selective against hepatocarcinoma cells at the concentration of 100g/mL. RA was the main compound identified in Z. marina, but not in Z. noltei.
- Polyunsaturated fatty acids of marine macroalgae: potential for nutritional and pharmaceutical applicationsPublication . Pereira, Hugo; Barreira, Luisa; Figueiredo, Filipe; Custodio, Luisa; Vizetto-Duarte, Catarina; Polo, Cristina; Resek, Eva; Engelen, Aschwin; Varela, JoaoAs mammals are unable to synthesize essential polyunsaturated fatty acids (PUFA), these compounds need to be taken in through diet. Nowadays, obtaining essential PUFA in diet is becoming increasingly difficult; therefore this work investigated the suitability of using macroalgae as novel dietary sources of PUFA. Hence, 17 macroalgal species from three different phyla (Chlorophyta, Phaeophyta and Rhodophyta) were analyzed and their fatty acid methyl esters (FAME) profile was assessed. Each phylum presented a characteristic fatty acid signature as evidenced by clustering of PUFA profiles of algae belonging to the same phylum in a Principal Components Analysis. The major PUFA detected in all phyla were C-18 and C-20, namely linoleic, arachidonic and eicosapentaenoic acids. The obtained data showed that rhodophytes and phaeophytes have higher concentrations of PUFA, particularly from the n-3 series, thereby being a better source of these compounds. Moreover, rhodophytes and phaeophytes presented. healthier. Sigma(n-6/)Sigma(n-3) and PUFA/saturated fatty acid ratios than chlorophytes. Ulva was an exception within the Chlorophyta, as it presented high concentrations of n-3 PUFA, alpha-linolenic acid in particular. In conclusion, macroalgae can be considered as a potential source for large-scale production of essential PUFA with wide applications in the nutraceutical and pharmacological industries.
- Can macroalgae provide promising anti-tumoral compounds? A closer look at Cystoseira tamariscifolia as a source for antioxidant and anti-hepatocarcinoma compoundsPublication . Vizetto-Duarte, C; Custódio, Luísa; Acosta, Gerardo; Lago, João H. G.; Morais, Thiago R.; Sousa, Carolina Bruno de; Gangadhar, Katkam N.; Rodrigues, Maria Joao; Pereira, Hugo; Lima, Raquel T.; Vasconcelos, M. Helena; Barreira, Luísa; Rauter, Amélia P.; Albericioi, Fernando; Varela, J.Marine organisms are a prolific source of drug leads in a variety of therapeutic areas. In the last few years, biomedical, pharmaceutical and nutraceutical industries have shown growing interest in novel compounds from marine organisms, including macroalgae. Cystoseira is a genus of Phaeophyceae (Fucales) macroalgae known to contain bioactive compounds. Organic extracts (hexane, diethyl ether, ethyl acetate and methanol extracts) from three Cystoseira species (C. humilis, C. tamariscifolia and C. usneoides) were evaluated for their total phenolic content, radical scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'- azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) radicals, and antiproliferative activity against a human hepatocarcinoma cell line (HepG2 cells). C. tamariscifolia had the highest TPC and RSA. The hexane extract of C. tamariscifolia (CTH) had the highest cytotoxic activity (IC50 = 2.31 mu g/mL), and was further tested in four human tumor (cervical adenocarcinoma HeLa; gastric adenocarcinoma AGS; colorectal adenocarcinoma HCT-15; neuroblastoma SH-SY5Y), and two non-tumor (murine bone marrow stroma S17 and human umbilical vein endothelial HUVEC) cell lines in order to determine its selectivity. CTH strongly reduced viability of all tumor cell lines, especially of HepG2 cells. Cytotoxicity was particularly selective for the latter cells with a selectivity index = 12.6 as compared to non-tumor cells. Incubation with CTH led to a 2-fold decrease of HepG2 cell proliferation as shown by the bromodeoxyuridine (BrdU) incorporation assay. CTH-treated HepG2 cells presented also pro-apoptotic features, such as increased Annexin Wpropidium iodide (PI) binding and dose-dependent morphological alterations in DAPI-stained cells. Moreover, it had a noticeable disaggregating effect on 3D multicellular tumor spheroids. Deme boxy cystoketal chromane, a derivative of the meroditerpenoid cystoketal, was identified as the active compound in CTH and was shown to display selective in vitro cYtotoxicitY towards HepG2 cells.
- Methanol extracts from Cystoseira tamariscifolia and Cystoseira nodicaulis are able to inhibit cholinesterases and protect a human dopaminergic cell line from hydrogen peroxide-induced cytotoxicityPublication . Custódio, Luísa; Silvestre, Laura; Rocha, Maria Isabel; Rodrigues, Maria Joao; Vizetto-Duarte, C; Pereira, Hugo; Barreira, Luísa; Varela, J.Context Marine macroalgae contain several bioactive molecules that may be developed as functional foods, but information about their neuroprotective potential is scarce.Objective The objective of this study is to determine the in vitro antioxidant and neuroprotective features of marine algae from the southern coast of Portugal and to assess the total content of different types of bioactives.Materials and methods Methanol extracts from 21 macroalgal species from the southern Portugal were evaluated for in vitro antioxidant and acetylcholinesterase (AChE) inhibition. Active extracts were further evaluated for inhibitory activity against butyrylcholinesterase (BuChE) and tyrosinase (TYRO), and for their ability to attenuate hydrogen peroxide (H2O2)-induced toxicity in SH-SY5Y cells. The total contents of different phenolic groups were determined for the most active extracts.ResultsCystoseira tamariscifolia (Hudson) Papenfuss (Sargassaceae) had the highest antiradical activity (92%, 1mg/mL). Cystoseira nodicaulis (Withering) M. Roberts (Sargassaceae) (75%) and Cystoseira humilis Schousboe ex Kutzing (Sargassaceae) (70%) had the highest iron-chelating activity at 10mg/mL. Cystoseira baccata (S.G. Gmelin) P.C. Silva (Sargassaceae) was more active towards copper (66%, 10mg/mL). Cystoseira tamariscifolia had the highest AChE inhibitory capacity (85%, 10mg/mL). Cystoseira tamariscifolia and C. nodicaulis were also active against BuChE and TYRO, and were able to protect SH-SY5Y cells against oxidative stress induced by H2O2. Cystoseira tamariscifolia had the highest content of all the groups of phenolics, and was particularly enriched in hydroxycinnamic acids (106mg CAE/g DW).Discussion and conclusion Results indicate that C. tamariscifolia and C. nodicaulis are important sources of nutraceutical compounds and may be considered functional foods that could improve cognitive functions.
- Isololiolide, a carotenoid metabolite isolated from the brown alga Cystoseira tamariscifolia, is cytotoxic and able to induce apoptosis in hepatocarcinoma cells through caspase-3 activation, decreased Bcl-2 levels, increased p53 expression and PARP cleavagePublication . Vizetto-Duarte, C; Custódio, Luísa; Gangadhar, Katkam N.; Lago, João Henrique G.; Dias, Catarina; Matos, Ana Marta; Neng, Nuno; Nogueira, José Manuel Florêncio; Barreira, Luísa; Albericio, Fernando; Rauter, Amelia P.; Varela, JoãoBackground: Brown macroalgae have attracted attention because they display a wide range of biological activities, including antitumoral properties. In this study we isolated isololiolide from Cystoseira tamariscifolia for the first time.Purpose: To examine the therapeutical potential of isololiolide against tumor cell lines.Methods/Study design: The structure of the compound was established and confirmed by 1D and 2D NMR as well as HRMS spectral analysis. The in vitro cytotoxicity was analyzed by colorimetric 3-(4,5-dimethylthiazol- 2-yl)-2,5-diphenyltetrazolium bromide assay in tumoral as well as in non-tumoral cell lines. Cell cycle arrest and induction of apoptosis were assessed by flow cytometry. Alteration of expression levels in proteins important in the apoptotic cascade was analyzed by western blotting.Results: Isololiolidewas isolated for the first time from the brown macroalga C. tamariscifolia. Isololiolide exhibited significant cytotoxic activity against three human tumoral cell lines, namely hepatocarcinoma HepG2 cells, whereas no cytotoxicity was found in non-malignant MRC-5 and HFF-1 human fibroblasts. Isololiolide completely disrupted the HepG2 normal cell cycle and induced significant apoptosis. Moreover, western blot analysis showed that isololiolide altered the expression of proteins that are important in the apoptotic cascade, increasing PARP cleavage and p53 expression while decreasing procaspase-3 and Bcl-2 levels.Conclusion: Isololiolide isolated from C. tamariscifolia is able to exert a selective cytotoxic activity on hepatocarcinoma HepG2 cells as well as induce apoptosis through the modulation of apoptosis-related proteins. (C) 2016 Elsevier GmbH. All rights reserved.
- Sustainable valorization of halophytes from the Mediterranean area: a comprehensive evaluation of their fatty acid profile and implications for human and animal nutritionPublication . Vizetto-Duarte, C; Figueiredo, Filipe; Rodrigues, Maria João; Polo, Cristina; Rešek, Eva; Custódio, LuísaHalophytic plants can provide an economical and environmentally sustainable source of products for human and animal feeding, in the context of the increase of worldwide emergent semi-arid landscapes. This work reports a comprehensive evaluation of the qualitative and quantitative composition of fatty acids (FA) of nineteen Mediterranean halophytes collected in southern Portugal, with the purpose of establishing their possible uses as food and feed. For FA determination, lipids and free FA were converted to the corresponding fatty acid methyl esters (FAME) and analyzed by GC-MS. Beta maritima had the highest FAME levels (7.3 mg/g DW) while Suaeda vera had the lowest content (1.0 mg/g DW). The most common saturated fatty acid (SFA) across all studied species was palmitic acid. The most prevalent monounsaturated fatty acid (MUFA) was oleic acid. Polyunsaturated fatty acids (PUFA) levels were led by linoleic acid. Less common FAMEs were also detected, namely eicosadienoic and hexadecatrienoic acids. Cotula coronopifolia, Phragmites australis and Suaeda vera displayed the best FA nutritional profiles. These species also showed bioactivities relevant for both human and animal health according to the literature and thus, collectively with this study, they could be further explored as food and feed.
- Report of in vitro antileishmanial properties of Iberian macroalgaePublication . Bruno De Sousa, Carolina; Lago, João Henrique G.; Macridachis, Jorge; Oliveira, Marta; Brito, Luis; Vizetto-Duarte, C; Florindo, Claudia; Hendrickx, Sarah; Maes, Louis; Morais, Thiago; Uemi, Miriam; Neto, Luís; Dionísio, Lídia; Cortes, Sofia; Barreira, Luísa; Custódio, Luísa; Alberício, Fernando; Campino, Lenea; Varela, JoãoHere is reported the anti Leishmania infantum activity of 48 hexane, CH2Cl2 and MeOH extracts from 16 macroalgae collected on the Iberian Coast. Seven hexane and CH2Cl2Cystoseira baccata, Cystoseira barbata, Cystoseira tamariscifolia, Cystoseira usneoides, Dictyota spiralis and Plocamium cartilagineum extracts were active towards promastigotes (IC50 29.8-101.8 μg/mL) inducing strong morphological alterations in the parasites. Hexane extracts of C. baccata and C. barbata were also active against intracellular amastigotes (IC50 5.1 and 6.8 μg/mL, respectively). Fatty acids, triacylglycerols, carotenoids, steroids and meroterpenoids were detected by nuclear magnetic resonance (NMR), and gas chromatography in the Cystoseira extracts. These results suggest that Cystoseira macroalgae contain compounds with antileishmanial activity, which could be explored as scaffolds to the development of novel sources of antiparasitic derivatives.