RESUMO
Sulfated polysaccharides (SPs) from seaweeds are potential bioactive natural compounds, but their DNA protective activity is poorly explored. This article aimed to evaluate the genotoxic/antigenotoxic potentials of a sulfated heterofucan from brown seaweed Spatoglossum schröederi (Fucan A - FA) and a sulfated galactan from green seaweed Codium isthomocladum (3G4S) using in vitro Comet assay (alkaline and oxidative versions) with HepG2 cells. The antioxidant activity of these SPs was evaluated by total antioxidant capacity, radical scavenging, metal chelating, and antioxidant enzyme activity assays. Both SPs were not genotoxic. FA and 3G4S displayed strong antigenotoxic activity against oxidizing chemical (H2O2) but not against alkylating chemical (MMS). The DNA damage reduction after a pre-treatment of 72 h with these SPs was 81.42% to FA and 81.38% to 3G4S. In simultaneous exposure to FA or 3G4S with H2O2, HepG2 cells presented 48.04% and 55.41% of DNA damage reduction compared with the control, respectively. The antigenotoxicity of these SPs relates to direct antioxidant activity by blockage of the initiation step of the oxidative chain reaction. Therefore, we conclude that FA and 3G4S could be explored as functional natural compounds with antigenotoxic activity due to their great protection against oxidative DNA damage.
Assuntos
Alga Marinha , Sulfatos , Antioxidantes/química , Antioxidantes/farmacologia , Dano ao DNA , Peróxido de Hidrogênio , Oxirredução , Polissacarídeos/química , Polissacarídeos/farmacologia , Alga Marinha/química , Sulfatos/químicaRESUMO
Polysaccharides α-D-galactan (GAL-Am) and ß-D-glucan (GLC-Am) were obtained from Amanita muscaria fruiting bodies. They were purified using different methodologies, such as Fehling precipitation (for both fractions), freeze-thawing process and ultrafiltration (for GLC-Am). Results showed that the GAL-Am has (1 â 6)-linked Galp main chain branched at O-2 by terminal Galp units and has not been previously reported. Besides, GLC-Am has (1 â 3)-linked Glcp in the main chain, substituted at O-6 by (1 â 6)-linked ß-Glcp units. Both are water-soluble, with 9.0 × 103 g/moL and 1.3 × 105 g/moL, respectively. GAL-Am and GLC-Am presented a selective proliferation reduction against B16-F10 melanoma cell line, not affecting non tumoral BALB/3T3 fibroblast cell line. Furthermore, both fractions reduced clonogenic capacity of melanoma cell line over an extended period of time. These results were obtained without modulations in B16-F10 cell adhesion, reinforcing the biological activities towards cell proliferation impairment and eliciting these polysaccharides as promising compounds to further exploration of their antimelanoma properties.
Assuntos
Amanita/metabolismo , Antineoplásicos , Galactanos , Glucanos , Melanoma Experimental/tratamento farmacológico , Animais , Antineoplásicos/química , Antineoplásicos/farmacologia , Células 3T3 BALB , Proliferação de Células/efeitos dos fármacos , Galactanos/química , Galactanos/farmacologia , Glucanos/química , Glucanos/farmacologia , CamundongosRESUMO
In this paper, the biologically inert agarose was selectively modified at C6 of ß-d-Galp units to produce an amino derivative with antibacterial property. The synthetic route involved the preparation of tosyl and azido agarose intermediates. All the polysaccharide derivatives were characterized by mono- and bidimensional 1H and 13C NMR and FT-IR analysis. A water-soluble amino polymer (Mw = 39,000 g mol-1, DSamino = 0.50) was produced by partial acid hydrolysis showing bactericidal and bacteriostatic activity against P. aeruginosa (ATCC 9027), S. aureus (ATCC 6538), and E. coli (ATCC 25922), with MIC values lower than 2.5 mg mL-1 and MBC values ranging from 2.5 to 5.0 mg mL-1.
Assuntos
Staphylococcus aureus , Antibacterianos , Escherichia coli , Testes de Sensibilidade Microbiana , SefaroseRESUMO
Seaweeds biosynthesize sulfated polysaccharides as key components of their cell walls. These polysaccharides are potentially interesting as biologically active compounds. Green macroalgae of the class Ulvophyceae comprise sulfated polysaccharides with great structural differences regarding the monosaccharide constituents, linearity of their backbones, and presence of other acidic substituents in their structure, including uronic acid residues and pyruvic acid. These structures have been thoroughly studied in the Ulvales and Ulotrichales, but only more recently have they been investigated with some detail in ulvophytes with giant multinucleate (coenocytic) cells, including the siphonous Bryopsidales and Dasycladales, and the siphonocladous Cladophorales. An early classification of these structurally heterogeneous polysaccharides was based on the presence of uronic acid residues in these molecules. In agreement with this classification based on chemical structures, sulfated polysaccharides of the orders Bryopsidales and Cladophorales fall in the same group, in which this acidic component is absent, or only present in very low quantities. The cell walls of Dasycladales have been less studied, and it remains unclear if they comprise sulfated polysaccharides of both types. Although in the Bryopsidales and Cladophorales the most important sulfated polysaccharides are arabinans and galactans (or arabinogalactans), their major structures are very different. The Bryopsidales produce sulfated pyruvylated 3-linked ß-d-galactans, in most cases, with ramifications on C6. For some species, linear sulfated pyranosic ß-l-arabinans have been described. In the Cladophorales, also sulfated pyranosic ß-l-arabinans have been found, but 4-linked and highly substituted with side chains. These differences are consistent with recent molecular phylogenetic analyses, which indicate that the Bryopsidales and Cladophorales are distantly related. In addition, some of the Bryopsidales also biosynthesize other sulfated polysaccharides, i.e., sulfated mannans and sulfated rhamnans. The presence of sulfate groups as a distinctive characteristic of these biopolymers has been related to their adaptation to the marine environment. However, it has been shown that some freshwater algae from the Cladophorales also produce sulfated polysaccharides. In this review, structures of sulfated polysaccharides from bryopsidalean, dasycladalean, and cladophoralean green algae studied until now are described and analyzed based on current phylogenetic understanding, with the aim of unveiling the important knowledge gaps that still exist.
RESUMO
Melanoma is the most lethal form of skin cancer, with a worldwide increase in incidence. Despite the increased overall survival of metastatic melanoma patients given recent advances in targeted and immunotherapy, it still has a poor prognosis and available treatment options carry diverse severe side effects. Polysaccharides from seaweed have been shown to exert antitumor activities. Here we show in vitro and in vivo antitumor activities of a sulfated homogalactan (named 3G4S) from Codium isthmocladum seaweed in the B16-F10 murine melanoma cell line. 3G4S did not induce cytotoxicity or proliferation changes; however, it was able to reduce solid tumor growth and metastasis, while not inducing side effects in mice. B16-F10 cells traits related to the metastatic cascade were also impaired by 3G4S, reducing cell invasion, colony-forming capacity and membrane glycoconjugates. Therefore, 3G4S shows promising antitumor activities without the commonly associated drawbacks of cancer treatments and can be further explored.
Assuntos
Galactanos/farmacologia , Química Verde , Melanoma Experimental/prevenção & controle , Alga Marinha/química , Sulfatos/química , Animais , Apoptose , Proliferação de Células , Feminino , Humanos , Masculino , Melanoma Experimental/secundário , Camundongos , Camundongos Endogâmicos C57BL , Células Tumorais CultivadasRESUMO
The water-soluble fractions of pectin extracted from the pulp of ripe papayas have already been found to exert positive effects on cancer cell cultures. However, the mechanisms that lead to these beneficial effects and the pectin characteristics that exert these effects are still not well understood. Characteristics such as molecular size, monosaccharide composition and structural conformation are known as polysaccharide factors that can cause alterations in cellular response. During fruit ripening, a major polysaccharide solubilization, depolymerization, and chemical modification occur. The aims of this work are to fractionate the pectin extracted from the pulp of papayas at two stages of ripening (fourth and ninth day after harvesting) into uronic and neutral fractions and to test them for the inhibition of human recombinant galectin-3 and the inhibition of colon cancer cell growth. The structures of the fractions were chemically characterized, and the uronic fraction extracted from the fourth day after harvesting presented the best biological effects across different concentrations in both galectin-3 inhibition and viability assays. The results obtained may help to establish a relationship between the chemical structures of papaya pectins and the positive in vitro biological effects, such as inhibiting cancer cell growth.
Assuntos
Proteínas Sanguíneas/metabolismo , Carica/fisiologia , Neoplasias do Colo/metabolismo , Galectinas/metabolismo , Pectinas/farmacologia , Ácidos Urônicos/química , Carica/química , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Parede Celular/química , Neoplasias do Colo/tratamento farmacológico , Regulação para Baixo/efeitos dos fármacos , Regulação Neoplásica da Expressão Gênica/efeitos dos fármacos , Células HCT116 , Células HT29 , Humanos , Pectinas/química , Polissacarídeos/análiseRESUMO
The genus Gracilaria synthesizes sulfated polysaccharides (SPs). Many of these SPs, including those synthesized by the edible seaweed Gracilaria birdiae, have not yet been adequately investigated for their use as potential pharmaceutical compounds. Previous studies have demonstrated the immunomodulatory effects of sulfated galactans from G. birdiae. In this study, a galactan (GB) was extracted from G. birdiae and evaluated by cell proliferation and antioxidant tests. GB showed no radical hydroxyl (OH) and superoxide (O2-) scavenging ability. However, GB was able to donate electrons in two further different assays and presented iron- and copper-chelating activity. Urolithiasis affects approximately 10% of the world's population and is strongly associated with calcium oxalate (CaOx) crystals. No efficient compound is currently available for the treatment of this disease. GB appeared to interact with and stabilize calcium oxalate dihydrate crystals, leading to the modification of their morphology, size, and surface charge. These crystals then acquired the same characteristics as those found in healthy individuals. In addition, GB showed no cytotoxic effect against human kidney cells (HEK-293). Taken together, our current findings highlight the potential application of GB as an antiurolithic agent.
Assuntos
Antioxidantes/química , Oxalato de Cálcio/antagonistas & inibidores , Gracilaria/química , Polissacarídeos/química , Cálcio/química , Oxalato de Cálcio/química , Sobrevivência Celular , Quelantes/farmacologia , Cobre/química , Desenho de Fármacos , Elétrons , Galactanos/química , Células HEK293 , Humanos , Hidrólise , Radical Hidroxila , Íons , Ferro/química , Rim/efeitos dos fármacos , Monossacarídeos/química , Oxigênio/química , Proteínas , Alga Marinha/química , Superóxidos/químicaRESUMO
Carbohydrates are known to act as analog receptors for bacteria and therefore are promising alternatives for the control and prevention of bacterial infections. The present study evaluated the chemical structure of modified soybean meal polysaccharides and their capacity to adhere enterobacteria (Salmonella Typhimurium) and to interfere with the bacteria adhesion to the known analogue receptors, using in vitro assays. For this, soybean meal suspensions were subjected to a thermochemical extraction process and structural analyses showed that the fraction with higher adhesion and adhesion-inhibition potential, SAP, was constituted by two types of polysaccharides: a partially depolymerized pectin, of high molar mass, composed of xylogalacturonan and rhamnogalacturonan regions (SAP1, 545.5â¯kDa), and a (1â¯ââ¯4)-linked-ß-D-galactan of low molar mass (SAP2, 8.7â¯kDa). The results showed a high affinity of Salmonella for galactans, while high molar mass pectins showed no adhesion capacity. The chemical compositions of the fractions suggested that galactose could be responsible for the recognition process in the adhesion process. Other factors, such as structure and degree of polymerization of the polymers, may also be influencing the adhesion process. Modified soybean meal polysaccharides appear to be a promising alternative agent to antibiotics for the control and prevention of foodborne diseases.
Assuntos
Aderência Bacteriana/efeitos dos fármacos , Glycine max/química , Polissacarídeos/farmacologia , Salmonella/fisiologia , Calibragem , Metilação , Peso Molecular , Salmonella/efeitos dos fármacosRESUMO
This work shows an optimized enzymatic hydrolysis of high molecular weight potato galactan yielding pectic galactan-oligosaccharides (PGOs), where endo-ß-1,4-galactanase (galactanase) from Cellvibrio japonicus and Clostridium thermocellum was used. For this, response surface methodology (RSM) by central composite design (CCD) was applied. The parameters varied were temperature (°C), pH, incubation time (min), and enzyme/substrate ratio (U/mg). The optimized conditions for the production of low degree of polymerization (DP) PGOs were obtained for each enzyme by spectrophotometric assay and confirmed by chromatography. The optimal conditions predicted for the use of C. japonicus galactanase to obtain PGOs of DP = 2 were T = 51.8 °C, pH 5, E/S = 0.508 U/mg, and t = 77.5 min. For DP = 3, they were T = 21 °C, pH 9, E/S = 0.484 U/mg, and t = 12.5 min; and for DP = 4, they were T = 21 °C, pH 5, E/S = 0.462 U/mg, and t = 12.5 min. The efficiency results were 51.3% for substrate hydrolysis. C. thermocellum galactanase had a lower yield (35.7%) and optimized conditions predicted for PGOs of DP = 2 were T = 60 °C, pH 5, E/S = 0.525 U/mg, and time = 148 min; DP = 3 were T = 59.7 °C, pH 5, E/S = 0.506 U/mg, and time = 12.5 min; and DP = 4, were T = 34.5 °C, pH 11, E/S = 0.525 U/mg, and time = 222.5 min. Fourier transformed infrared (FT-IR) and nuclear magnetic resonance (NMR) characterizations of PGOs are presented.
RESUMO
The anticoagulant and antithrombotic properties of three structurally correlated sea urchin-derived 3-linked sulfated α-glycans and their low molecular-weight derivatives were screened comparatively through various in vitro and in vivo methods. These methods include activated partial thromboplastin time, the inhibitory activity of antithrombin over thrombin and factor Xa, venous antithrombosis, the inhibition of platelet aggregation, the activation of factor XII, and bleeding. While the 2-sulfated fucan from Strongylocentrotus franciscanus was observed to be poorly active in most assays, the 4-sulfated fucan from Lytechinus variegatus, the 2-sulfated galactan from Echinometra lucunter and their derivatives showed multiple effects. All marine compounds showed no capacity to activate factor XII and similar low bleeding tendencies regardless of the dose concentrations used to achieve the highest antithrombotic effect observed. The 2-sulfated galactan showed the best combination of results. Our work improves the background about the structure-function relationship of the marine sulfated glycans in anticoagulation and antithrombosis. Besides confirming the negative effect of the 2-sulfated fucose and the positive effect of the 2-sulfated galactose on anticoagulation in vitro, our results also demonstrate the importance of this set of structural requirements on antithrombosis in vivo, and further support the involvement of high-molecular weight and 4-sulfated fucose in both activities.