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1.
J Chromatogr A ; 1731: 465215, 2024 Aug 30.
Artículo en Inglés | MEDLINE | ID: mdl-39068771

RESUMEN

A novel bio-supramolecular solvent (bio-SUPRAS) based on rhamnolipids (RLs) was designed for efficient extraction of pyrethroid insecticides in water and food matrices. Benefiting from RLs as amphiphiles equipped with the attractive properties of bio-degradable, low toxicity and high stability, bio-SUPRAS was spontaneously generated through salt induced coagulation. The bio-SUPRAS was characterized by cryo-scanning electron microscope and main factors influencing the extraction performance were investigated in detail. Under the optimized conditions, the method was found to have desirable limits of detection (5∼10 µg l-1), good precision (RSDs<16.9 %) and satisfactory recovery (75.2 %∼94.3 %). More importantly, the extraction mechanism was studied by density functional theory systematically. Following greenness assessment, the technique was successfully used for enrichment of pyrethroid pesticides in real samples before HPLC-UV analysis. Thus, the method showed the outstanding merits of eco-efficient, green, time-saving, and had favorable application prospect to remove trace analytes from intricate sample matrices.


Asunto(s)
Glucolípidos , Insecticidas , Piretrinas , Solventes , Contaminantes Químicos del Agua , Piretrinas/aislamiento & purificación , Piretrinas/análisis , Piretrinas/química , Insecticidas/aislamiento & purificación , Insecticidas/análisis , Insecticidas/química , Solventes/química , Glucolípidos/química , Glucolípidos/aislamiento & purificación , Contaminantes Químicos del Agua/aislamiento & purificación , Contaminantes Químicos del Agua/química , Contaminantes Químicos del Agua/análisis , Cromatografía Líquida de Alta Presión/métodos , Límite de Detección , Tecnología Química Verde/métodos , Contaminación de Alimentos/análisis
2.
Mar Drugs ; 22(6)2024 Jun 14.
Artículo en Inglés | MEDLINE | ID: mdl-38921590

RESUMEN

Ichthyotoxic red tide is a problem that the world is facing and needs to solve. The use of antialgal compounds from marine macroalgae to suppress ichthyotoxic red tide is considered a promising biological control method. Antialgal substances were screened and isolated from Bangia fusco-purpurea, Gelidium amansii, Gloiopeltis furcate, Hizikia fusifarme, Laminaria japonica, Palmaria palmata, and Sargassum sp. to obtain new materials for the development of algaecides against ichthyotoxic red tide microalgae using bioactivity-guided isolation methods. The fractions of seven macroalgae exhibited selective inhibitory activities against Amphidinium carterae and Karenia mikimotoi, of which the ethyl acetate fractions had the strongest and broadest antialgal activities for the two tested red tide microalgae. Their inhibitory effects on A. carterae and K. mikimotoi were even stronger than that of potassium dichromate, such as ethyl acetate fractions of B. purpurea, H. fusifarme, and Sargassum sp. Thin-layer chromatography and ultraviolet spectroscopy were further carried out to screen the ethyl acetate fraction of Sargassum sp. Finally, a new glycolipid derivative, 2-O-eicosanoyl-3-O-(6-amino-6-deoxy)-ß-D-glucopyranosyl-glycerol, was isolated and identified from Sargassum sp., and it was isolated for the first time from marine macroalgae. The significant antialgal effects of 2-O-eicosanoyl-3-O-(6-amino-6-deoxy)-ß-D-glucopyranosyl-glycerol on A. carterae and K. mikimotoi were determined.


Asunto(s)
Glucolípidos , Floraciones de Algas Nocivas , Microalgas , Algas Marinas , Algas Marinas/química , Glucolípidos/farmacología , Glucolípidos/aislamiento & purificación , Glucolípidos/química , Floraciones de Algas Nocivas/efectos de los fármacos , Microalgas/química , Dinoflagelados/química
3.
Acta Biochim Biophys Sin (Shanghai) ; 56(9): 1300-1310, 2024 May 16.
Artículo en Inglés | MEDLINE | ID: mdl-38761010

RESUMEN

Lotus seed skin extract is rich in flavonoids, making it a promising candidate for developing health products. In a previous study, we found that proanthocyanidins from lotus seed skin, particularly proanthocyanidin B1 (PB1), can indirectly activate the Nrf2 signaling pathway, exerting an antioxidant effect. In this study, we isolate proanthocyanidins from lotus seed skin (PLS) using ethanol extraction and RP-HPLC identification, and investigate its effects on glycolipid metabolism both in vivo and in vitro. Our results demonstrate that PLS reduces body weight in high-fat diet (HFD) mice by decreasing feed efficiency. PLS also normalizes serum glucose, insulin secretion, glycosylated hemoglobin (HbA1c), and intraperitoneal glucose tolerance (IPGTT). Furthermore, PLS significantly improves blood lipid parameters and inhibits the expressions of six proinflammatory factors, including IL-1α, IL-1ß, IL-3, IL-6, IFN-γ and TNF-α in HFD mice. Additionally, analysis of fresh liver tissues reveals that PLS and PB1 induce the expressions of antioxidant proteins such as HO-1 and NQO1 by activating the p38-Nrf2 signaling pathway and inhibiting the NF-κB signaling pathway. In conclusion, proanthocyanidins from lotus seed skin regulate glycolipid metabolism disorders by targeting the p38/Nrf2/NF-κB signaling pathway. Our study offers a new approach for the high-value comprehensive utilization of lotus seed skin by-products and precise dietary intervention for metabolic syndrome.


Asunto(s)
Dieta Alta en Grasa , Glucolípidos , Lotus , Factor 2 Relacionado con NF-E2 , FN-kappa B , Proantocianidinas , Semillas , Transducción de Señal , Animales , Proantocianidinas/farmacología , Proantocianidinas/aislamiento & purificación , Factor 2 Relacionado con NF-E2/metabolismo , Semillas/química , Lotus/química , FN-kappa B/metabolismo , Transducción de Señal/efectos de los fármacos , Ratones , Masculino , Glucolípidos/aislamiento & purificación , Glucolípidos/farmacología , Dieta Alta en Grasa/efectos adversos , Ratones Endogámicos C57BL , Extractos Vegetales/farmacología , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Hígado/metabolismo , Hígado/efectos de los fármacos , Humanos , Antioxidantes/farmacología , Antioxidantes/aislamiento & purificación
4.
Chemistry ; 30(43): e202401214, 2024 Aug 01.
Artículo en Inglés | MEDLINE | ID: mdl-38684455

RESUMEN

Reported herein is a new HPLC-based automated synthesizer (HPLC-A) capable of a temperature-controlled synthesis and purification of carbohydrates. The developed platform allows to perform various protecting group manipulations as well as the synthesis of O- and N-glycosides. A fully automated synthesis and purification was showcased in application to different carbohydrate derivatives including glycosides, oligosaccharides, glycopeptides, glycolipids, and nucleosides.


Asunto(s)
Carbohidratos , Oligosacáridos , Cromatografía Líquida de Alta Presión , Carbohidratos/química , Oligosacáridos/síntesis química , Oligosacáridos/química , Glicósidos/química , Glicósidos/síntesis química , Glucolípidos/química , Glucolípidos/síntesis química , Glucolípidos/aislamiento & purificación , Glicopéptidos/química , Glicopéptidos/síntesis química , Nucleósidos/química , Nucleósidos/síntesis química , Automatización , Temperatura
5.
Molecules ; 29(8)2024 Apr 12.
Artículo en Inglés | MEDLINE | ID: mdl-38675571

RESUMEN

Phyllanthus emblica is a natural medicinal herb with diverse bioactivities. Certain extracts from this herb have been confirmed to possess anti-glycolipid metabolic disorder activity. To further develop its utility value and explore its potential in combating glycolipid metabolic disorders, we designed a series of experiments to investigate the structure, antioxidant activity, and anti-glycolipid metabolic disorder activity of Phyllanthus emblica polysaccharides. In this study, we extracted and purified polysaccharides from Phyllanthus emblica and thoroughly analyzed their structure using various techniques, including NMR, methylation analysis, and surface-enhanced Raman spectroscopy. We investigated the hypolipidemic and anti-glycolipid metabolism disorder activity of Phyllanthus emblica polysaccharides for the first time utilizing oleic acid (OA) and advanced glycation end products (AGEs) as inducers. Additionally, the antioxidant activity of Phyllanthus emblica polysaccharides was assessed in vitro. These findings lay the groundwork for future investigations into the potential application of Phyllanthus emblica polysaccharides as an intervention for preventing and treating diabetes.


Asunto(s)
Antioxidantes , Phyllanthus emblica , Polisacáridos , Phyllanthus emblica/química , Polisacáridos/farmacología , Polisacáridos/química , Polisacáridos/aislamiento & purificación , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Glucolípidos/química , Glucolípidos/farmacología , Glucolípidos/aislamiento & purificación , Productos Finales de Glicación Avanzada/metabolismo , Extractos Vegetales/farmacología , Extractos Vegetales/química , Animales , Ácido Oléico/química , Ácido Oléico/farmacología , Humanos
6.
Mar Drugs ; 22(4)2024 Mar 24.
Artículo en Inglés | MEDLINE | ID: mdl-38667761

RESUMEN

In order to explore the extraction and activity of macroalge glycolipids, six macroalgae (Bangia fusco-purpurea, Gelidium amansii, Gloiopeltis furcata, Gracilariopsis lemaneiformis, Gracilaria sp. and Pyropia yezoensis) glycolipids were extracted with five different solvents firstly. Considering the yield and glycolipids concentration of extracts, Bangia fusco-purpurea, Gracilaria sp. and Pyropia yezoensis were selected from six species of marine macroalgae as the raw materials for the extraction of glycolipids. The effects of the volume score of methanol, solid-liquid ratio, extraction temperature, extraction time and ultrasonic power on the yield and glycolipids concentration of extracts of the above three macroalgae were analyzed through a series of single-factor experiments. By analyzing the antioxidant activity in vitro, moisture absorption and moisturizing activity, the extraction process of Bangia fusco-purpurea glycolipids was further optimized by response surface method to obtain suitable conditions for glycolipid extraction (solid-liquid ratio of 1:27 g/mL, extraction temperature of 48 °C, extraction time of 98 min and ultrasonic power of 450 W). Bangia fusco-purpurea extracts exhibited a certain scavenging effect on DPPH free radicals, as well as good moisture-absorption and moisture retaining activities. Two glycolipids were isolated from Bangia fusco-purpurea by liquid-liquid extraction, silica gel column chromatography and thin-layer chromatography, and they showed good scavenging activities against DPPH free radicals and total antioxidant capacity. Their scavenging activities against DPPH free radicals were about 60% at 1600 µg/mL, and total antioxidant capacity was better than that of Trolox. Among them, the moisturizing activity of a glycolipid was close to that of sorbierite and sodium alginate. These two glycolipids exhibited big application potential as food humectants and antioxidants.


Asunto(s)
Antioxidantes , Glucolípidos , Algas Marinas , Glucolípidos/química , Glucolípidos/aislamiento & purificación , Glucolípidos/farmacología , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Algas Marinas/química , Rhodophyta/química , Solventes/química , Picratos/química
7.
Biotechnol Bioeng ; 121(3): 853-876, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-38108218

RESUMEN

Biosurfactants are natural compounds with remarkable surface-active properties that may offer an eco-friendly alternative to conventional surfactants. Among them, mannosylerythritol lipids (MELs) stand out as an intriguing example of a glycolipid biosurfactant. MELs have been used in a variety of sectors for various applications, and are currently commercially produced. Industrially, they are used in the pharmaceutical, cosmetic, food, and agricultural industries, based on their ability to reduce surface tension and enhance emulsification. However, despite their utility, their production is comparatively limited industrially. From a bioprocessing standpoint, two areas of interest to improve the production process are upstream production and downstream (separation and purification) product recovery. The former has seen a significant amount of research, with researchers investigating several production factors: the microbial species or strain employed, the producing media composition, and the production strategy implemented. Improvement and optimization of these are key to scale-up the production of MELs. On the other hand, the latter has seen comparatively limited work presented in the literature. For the most part traditional separation techniques have been employed. This systematic review presents the production and purification methodologies used by researchers by comprehensively analyzing the current state-of-the-art with regards the production, separation, and purification of MELs. By doing so, the review presents different possible approaches, and highlights some potential areas for future work by identifying opportunities for the commercialization of MELs.


Asunto(s)
Glucolípidos , Tensoactivos , Glucolípidos/química , Glucolípidos/biosíntesis , Glucolípidos/aislamiento & purificación , Tensoactivos/química , Tensoactivos/metabolismo , Tensoactivos/aislamiento & purificación
8.
ChemistryOpen ; 10(9): 889-895, 2021 09.
Artículo en Inglés | MEDLINE | ID: mdl-34468091

RESUMEN

Due to their special chemical structure, tetraether lipids (TEL) represent essential elements of archaeal membranes, providing these organisms with extraordinary properties. Here we describe the characterization of a newly isolated structural element of the main lipids. The TEL fragment GDNT-ß-Glu was isolated from Sulfolobus metallicus and characterized in terms of its chemical structure by NMR- and MS-investigations. The obtained data are dissimilar to analogically derived established structures - in essence, the binding relationships in the polar head group are re-determined and verified. With this work, we provide an important contribution to the structure elucidation of intact TEL also contained in other Sulfolobus strains such as Solfulobus acidocaldarius and Sulfolobus solfataricus.


Asunto(s)
Diglicéridos/química , Glucolípidos/química , Lípidos de la Membrana/química , Sulfolobus/química , Espectroscopía de Resonancia Magnética con Carbono-13 , Ciclización , Diglicéridos/aislamiento & purificación , Glucolípidos/aislamiento & purificación , Espectrometría de Masas , Lípidos de la Membrana/aislamiento & purificación , Sulfolobus/clasificación
9.
Anal Bioanal Chem ; 413(16): 4311-4320, 2021 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-34003328

RESUMEN

Biosurfactants have been investigated as potential alternatives for synthetic surfactants in several areas, for example, in environmental and pharmaceutical fields. In that regard, extensive research has been carried out with sophorolipids and rhamnolipids that also present various biological properties with therapeutic significance. These biosurfactants are obtained as complex mixtures of slightly different molecules, and thus when studying these microbial glycolipids, the ability to identify and purify the produced compounds is of extreme importance. This study aimed to develop improved methodologies for the identification, separation, and purification of sophorolipids and rhamnolipids. Therefore, an ultra-high-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) method was modified to ensure faster characterization of both sophorolipids and rhamnolipids, enabling the identification and fragmentation pattern description of 10 and 13 congeners, respectively. The separation and purification of these biosurfactants was achieved with novel reversed-phase solid-phase extraction methods guaranteeing the isolation of different glycolipids, including those considered for their significant biological activity (e.g. antimicrobial, anticancer). It was possible to isolate sophorolipids and rhamnolipids with purity of 94% and 99%, respectively. The methods presented herein can be easily implemented and are expected to make purification of these biosurfactants easier, facilitating the study of their individual properties in further works.


Asunto(s)
Glucolípidos/análisis , Ácidos Oléicos/análisis , Tensoactivos/análisis , Cromatografía Líquida de Alta Presión , Glucolípidos/aislamiento & purificación , Ácidos Oléicos/aislamiento & purificación , Pseudomonas aeruginosa/química , Saccharomycetales/química , Extracción en Fase Sólida , Tensoactivos/aislamiento & purificación , Espectrometría de Masas en Tándem
10.
Sci Rep ; 11(1): 1298, 2021 01 14.
Artículo en Inglés | MEDLINE | ID: mdl-33446783

RESUMEN

Monogalactosyldiacylglycerol (MGDG) is the most abundant type of glycoglycerolipid found in the plant cell membrane and mostly in the chloroplast thylakoid membrane. The amphiphilic nature of MGDG is attractive in pharmaceutical fields for interaction with other biological molecules and hence exerting therapeutic anti-cancer, anti-viral, and anti-inflammatory activities. In this study, we investigated the therapeutic efficacy of cyanobacteria derived MGDG to inhibit breast cancer cell growth. MGDG was extracted from a cyanobacteria Synechocystis sp. PCC 6803 followed by a subsequent fractionation by column chromatographic technique. The purity and molecular structure of MGDG were analyzed by nuclear magnetic resonance (NMR) spectroscopy analysis. The presence of MGDG in the extracted fraction was further confirmed and quantified by high-performance liquid chromatography (HPLC). The anti-proliferation activity of the extracted MGDG molecule was tested against BT-474 and MDA-MB-231 breast cancer cell lines. The in vitro study showed that MGDG extracted from Synechocystis sp. PCC 6803 induced apoptosis in (70 ± 8) % of BT-474 (p < 0.001) and (58 ± 5) % of MDA-MB-231 cells (p < 0.001) using ~ 60 and 200 ng/ml of concentrations, respectively. The half-maximal inhibitory concentration, IC50 of MGDG extracted from Synechocystis sp. PCC 6803 were (27.2 ± 7.6) and (150 ± 70) ng/ml in BT-474 and MDA-MB-231 cell lines, respectively. Quantification of caspase-3/7 activity using flow cytometry showed (3.0 ± 0.4) and (2.1 ± 0.04)-fold (p < 0.001) higher protein expressions in the MGDG treated BT-474 and MDA-MB-231 cells, respectively than untreated controls conferring to the caspase-dependent apoptosis. The MGDG did not show any significant cytotoxic side effects in human dermal fibroblasts cells. A commercially available MGDG control did not induce any apoptotic cell death in cancer cells substantiating the potential of the MGDG extracted from Synechocystis sp. PCC 6803 for the treatment of breast cancer cells through the apoptosis-mediated pathway.


Asunto(s)
Apoptosis/efectos de los fármacos , Neoplasias de la Mama/tratamiento farmacológico , Glucolípidos , Synechocystis/química , Neoplasias de la Mama/metabolismo , Neoplasias de la Mama/patología , Línea Celular Tumoral , Femenino , Glucolípidos/química , Glucolípidos/aislamiento & purificación , Glucolípidos/farmacología , Humanos
11.
Carbohydr Polym ; 254: 117433, 2021 Feb 15.
Artículo en Inglés | MEDLINE | ID: mdl-33357906

RESUMEN

Driven by the need to find alternatives to control Staphylococcus aureus infections, this work describes the development of chitosan-based particulate systems as carriers for antimicrobial glycolipids. By using a simple ionic gelation method stable nanoparticles were obtained showing an encapsulation efficiency of 41.1 ± 8.8 % and 74.2 ± 1.3 % and an average size of 210.0 ± 15.7 nm and 329.6 ± 8.0 nm for sophorolipids and rhamnolipids chitosan-nanoparticles, respectively. Glycolipids incorporation and particle size was correspondingly corroborated by FTIR-ATR and TEM analysis. Rhamnolipids chitosan nanoparticles (RLs-CSp) presented the highest antimicrobial effect towards S. aureus (ATCC 25923) exhibiting a minimal inhibitory concentration of 130 µg/mL and a biofilm inhibition ability of 99 %. Additionally, RLs-CSp did not interfere with human dermal fibroblasts (AG22719) viability and proliferation under the tested conditions. The results revealed that the RLs-CSp were able to inhibit bacterial growth showing adequate cytocompatibility and might become, after additional studies, a valuable approach to prevent S. aureus related infections.


Asunto(s)
Antibacterianos/química , Quitosano/química , Portadores de Fármacos , Glucolípidos/química , Ácidos Oléicos/química , Staphylococcus aureus/efectos de los fármacos , Tensoactivos/química , Antibacterianos/aislamiento & purificación , Antibacterianos/farmacología , Biopelículas/efectos de los fármacos , Biopelículas/crecimiento & desarrollo , Ciclo Celular/efectos de los fármacos , Línea Celular , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Fibroblastos/citología , Fibroblastos/efectos de los fármacos , Glucolípidos/aislamiento & purificación , Glucolípidos/farmacología , Humanos , Pruebas de Sensibilidad Microbiana , Nanopartículas/química , Nanopartículas/ultraestructura , Ácidos Oléicos/aislamiento & purificación , Ácidos Oléicos/farmacología , Tamaño de la Partícula , Staphylococcus aureus/crecimiento & desarrollo , Tensoactivos/aislamiento & purificación , Tensoactivos/farmacología
12.
Molecules ; 25(20)2020 Oct 21.
Artículo en Inglés | MEDLINE | ID: mdl-33096808

RESUMEN

Mannosylerythritol lipids-A (MEL-A) is a novel biosurfactant with excellent surface activity and potential biomedical applications. In this study, we explored the antibacterial activity and the underlying mechanisms of MEL-A against the important food-borne pathogen Listeria monocytogenes. The bacterial growth and survival assays revealed a remarkable antibacterial activity of MEL-A. Since MEL-A is a biosurfactant, we examined the cell membrane integrity and morphological changes of MEL-A-treated bacteria by biochemical assays and flow cytometry analysis and electron microscopes. The results showed obvious damaging effects of MEL-A on the cell membrane and morphology. To further explore the antibacterial mechanism of MEL-A, a transcriptome analysis was performed, which identified 528 differentially expressed genes (DEGs). Gene ontology (GO) analysis revealed that the gene categories of membrane, localization and transport were enriched among the DEGs, and the analysis of the Kyoto Encyclopedia of Genes and Genomes (KEGG) pathways demonstrated significant changes in the maltodextrin ABC transporter system and stress response system. Furthermore, the growth of L. monocytogenes could also be significantly inhibited by MEL-A in milk, a model of a real food system, suggesting that MEL-A could be potentially applied as an natural antimicrobial agent to control food-borne pathogens in the food industry.


Asunto(s)
Antibacterianos/farmacología , Glucolípidos/farmacología , Listeria monocytogenes/efectos de los fármacos , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Glucolípidos/química , Glucolípidos/aislamiento & purificación , Listeria monocytogenes/crecimiento & desarrollo , Pruebas de Sensibilidad Microbiana
13.
Mar Drugs ; 18(9)2020 Sep 21.
Artículo en Inglés | MEDLINE | ID: mdl-32967264

RESUMEN

Total lipids were extracted from sandfish (Arctoscopus japonicus), and then they were separated into the following three lipid fractions: neutral lipids, glycolipids, and phospholipids. In this study, we analyzed the lipid fractions of A. japonicus eggs and we determined their anti-inflammatory activity in RAW264.7 macrophage cells. In these three lipid-fractions, the main fatty acids were as follows: palmitic acid (16:0), oleic acid (18:1n-9), docosahexaenoic acid (DHA, 22:6n-3), and eicosapentaenoic acid (EPA, 20:5n-3). Among the lipid fractions, phospholipids showed the highest concentration of DHA and EPA (21.70 ± 1.92 and 18.96 ± 1.27, respectively). The three lipid fractions of A. japonicus significantly suppressed the production of NO in macrophages. Moreover, they also significantly inhibited the expression of iNOS, COX-2, IL-6, IL-1ß, and TNF-α, in a dose-dependent manner. Furthermore, the lipid fractions of A. japonicus suppressed the nuclear translocation of NF-κB p65 subunits in a dose-dependent manner. In addition, they attenuated the activation of MAPKs (p38, ERK1/2, and JNK) phosphorylation in LPS-stimulated RAW264.7 cells. These results indicate that all the lipid fractions of A. japonicus exert anti-inflammatory activity by suppressing the activation of NF-κB and MAPK pathways. Therefore, the lipid fractions of A. japonicus might be potentially used as anti-inflammatory agents.


Asunto(s)
Antiinflamatorios/farmacología , Glucolípidos/farmacología , Lípidos/farmacología , Fosfolípidos/farmacología , Animales , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Peces , Glucolípidos/aislamiento & purificación , Inflamación/tratamiento farmacológico , Inflamación/patología , Lípidos/química , Lípidos/aislamiento & purificación , Lipopolisacáridos , Sistema de Señalización de MAP Quinasas/efectos de los fármacos , Macrófagos/efectos de los fármacos , Macrófagos/patología , Ratones , FN-kappa B/metabolismo , Óvulo/química , Fosfolípidos/aislamiento & purificación , Células RAW 264.7
14.
Lipids ; 55(6): 671-682, 2020 11.
Artículo en Inglés | MEDLINE | ID: mdl-32770855

RESUMEN

Lipid composition of liposomal bilayer should alter the cell response for permeability, transport, and uptake in small intestine. This work was done to investigate the transport and uptake of liposomes composed of docosahexaenoic acid-enriched phosphatidylcholine (PtdCho), phosphatidylserine (PtdSer), and sulfoquinovosyl diacylglycerol (SQDG) derived from marine products on multilamellar vesicles (MLV) in small intestinal epithelial cell models. The results showed that addition of PtdSer and SQDG as liposomal bilayer could improve the efficiency entrapment of liposomes. The liposomes containing PtdSer showed higher transport and uptake through both Caco-2 cell and M cell monolayers as compared to PtdCho-MLV. SQDG-containing liposomes exhibited only higher transport through M cell monolayer, while its uptake effect was higher both in Caco-2 cell and M cell monolayers. The results of experiments done with endocytosis inhibitors indicated that PtdCho-MLV must be transported via macropinocytosis and uptaken by phagocytosis in M cell monolayer model. PtdCho/PtdSer-MLV and PtdCho/SQDG-MLV might be transported and uptaken through M cell monolayer by phagocytosis. The result also indicated that PtdCho/SQDG-MLV could open the tight junction of small intestinal epithelial cell monolayers. Furthermore, our findings demonstrated that the surface status of cholesterol-containing liposomes were smooth, but they did not affect their transport and uptake through Caco-2 cell and M cell monolayers.


Asunto(s)
Ácidos Grasos/análisis , Intestino Delgado/citología , Liposomas/química , Liposomas/farmacocinética , Animales , Transporte Biológico , Células CACO-2 , Técnicas de Cocultivo , Decapodiformes/química , Células Epiteliales , Colorantes Fluorescentes/farmacocinética , Glucolípidos/aislamiento & purificación , Glucolípidos/farmacocinética , Humanos , Intestino Delgado/metabolismo , Isoquinolinas/farmacocinética , Microscopía de Fuerza Atómica , Fosfatidilcolinas/farmacocinética , Sargassum/química
15.
Anal Chem ; 92(16): 11250-11259, 2020 08 18.
Artículo en Inglés | MEDLINE | ID: mdl-32667194

RESUMEN

In lipidomic analysis by direct mass spectrometry (MS), high abundance lipids with high ionizability (such as glycerophospholipids) would cause ion suppression to lipids with poor ionizability and low abundance (such as glycolipids, sphingolipids, or glycerides), which largely limits the detection coverage for lipidomics. In this work, TiO2-based liquid microjunction surface sampling (LMJSS) coupled with MS was used for separation of glycerides, phospholipids and glycolipids/sphingolipids in biological samples and rapid analysis of lipids in different classes with high lipidome coverage. We found that, in nonaqueous aprotic solvents, lipids with a glycosyl or sphingosine group could be selectively separated from lipids with a phosphate group (selectivity >10) after being coenriched on TiO2 by tuning the solvent composition. Accordingly, a selective multistep extraction method was developed by loading the biosamples on TiO2 slides in neutral aprotic solvent, and sequentially eluting glycerides in pure acetonitrile, glycerophospholipids in 6% ammonia-94% acetonitrile (v/v) and glycolipids/sphingolipids in 5% formic acid-95% methanol (v/v) by LMJSS probe from TiO2 slide. Each eluate from TiO2 slide was directly delivered by LMJSS to MS for analysis. The total detection time with three desorption steps would be controlled in 3 min. The method performance for each lipid class was evaluated using lipid standards, including matrix effects (107-128%), RSDs (0.4-16%), linearity (0.98-0.99), detection limits (5-3000 ng/mL), the adsorption equilibrium constants (102-104) and adsorption capacity (1-38 µg/mm2) of TiO2 coated slides to lipids. Finally, the TiO2-based-LMJSS-MS method was applied to lipidomic analysis for blood plasma and brain tissue, and compared with direct infusion MS. Results showed that (2-5)-fold more sphingolipids/glycolipids and 40-50 more glycerophospholipids/glycerides were identified in both plasma and brain extract by the new method comparing with direct infusion MS method. Detected lipids were quantified with standard addition calibration method, and the absolute quantitation results measured by TiO2-based-LMJSS-MS were verified with that by the traditional LC-MS method (correlation coefficient >0.98, slope of correlation line = 0.87-1.05).


Asunto(s)
Glicerofosfolípidos/sangre , Glucolípidos/sangre , Esfingolípidos/sangre , Titanio/química , Adsorción , Animales , Glicerofosfolípidos/química , Glicerofosfolípidos/aislamiento & purificación , Glucolípidos/química , Glucolípidos/aislamiento & purificación , Humanos , Límite de Detección , Lipidómica/métodos , Extracción Líquido-Líquido/métodos , Espectrometría de Masas/métodos , Ratas , Esfingolípidos/química , Esfingolípidos/aislamiento & purificación
16.
World J Microbiol Biotechnol ; 36(6): 88, 2020 Jun 05.
Artículo en Inglés | MEDLINE | ID: mdl-32500290

RESUMEN

This work reports the production of MEL-A using coconut water as the carbon source. Proximate analysis of coconut water indicated the presence of nutrients necessary for growth of the organism and production of desired metabolite. The amount of MEL produced using coconut water was 3.85 g/L (± 0.35) with 74% of it being MEL-A when compared to 2.58 g/L (± 0.15) with 60% being MEL-A using glycerol, a conventional carbon source. MEL-A from coconut water consisted of 38.1% long-chain saturated fatty acids (C16:0 and C18:0) whereas with glycerol it was 9.6%. The critical micellar concentration of the biosurfactant from coconut water was 2.32 ± 0.21 µM when compared to 4.41 ± 0.25 µM from glycerol. The stability of O/W emulsion was reduced by 50% and 90% after incubation for 8 h in the case of MEL-A from coconut water and glycerol respectively when compared to synthetic surfactant, Tween-20. MEL-A from both the sources exhibited free radical scavenging activity (DPPH assay) in a dose-dependent manner wherein MEL-A from coconut water showed two fold higher activity than the other. The interaction of coconut water MEL-A with DPPC for drug encapsulation applications was also studied. The DSC measurements showed the differences in the interaction of drugs with DPPC/MEL-A liposome. The differences were also observed in the solubility of drugs after encapsulation with DPPC/MEL-A liposome.


Asunto(s)
Basidiomycota/metabolismo , Cocos/metabolismo , Glucolípidos/biosíntesis , Carbono/análisis , Carbono/química , Cocos/química , Sistemas de Liberación de Medicamentos/métodos , Emulsiones/química , Emulsiones/aislamiento & purificación , Ácidos Grasos/análisis , Ácidos Grasos/química , Fermentación , Glicerol/metabolismo , Glucolípidos/química , Glucolípidos/aislamiento & purificación , Liposomas , Micelas , Tensoactivos/química , Tensoactivos/aislamiento & purificación
17.
ACS Chem Biol ; 15(7): 1835-1841, 2020 07 17.
Artículo en Inglés | MEDLINE | ID: mdl-32293864

RESUMEN

The first asymmetric total synthesis of three structures proposed for mycobacterial diacyl trehaloses, DAT1, DAT2, and DAT3 is reported. The presence of two of these glycolipids, DAT1 and DAT3, within different strains of pathogenic M. tuberculosis was confirmed, and it was shown that their abundance varies significantly. In mass spectrometry, synthetic DAT2 possessed almost identical fragmentation patterns to presumptive DAT2 from Mycobacterium tuberculosis H37Rv, but did not coelute by HPLC, raising questions as the precise relationship of the synthetic and natural materials. The synthetic DATs were examined as agonists for signaling by the C-type lectin, Mincle. The small differences in the chemical structure of the lipidic parts of DAT1, DAT2, and DAT3 led to drastic differences of Mincle binding and activation, with DAT3 showing similar potency as the known Mincle agonist trehalose dimycolate (TDM). In the future, DAT3 could serve as basis for the design of vaccine adjuvants with simplified chemical structure.


Asunto(s)
Glucolípidos/farmacología , Lectinas Tipo C/agonistas , Proteínas de la Membrana/agonistas , Receptores Inmunológicos/agonistas , Trehalosa/análogos & derivados , Trehalosa/farmacología , Animales , Cromatografía Liquida , Glucolípidos/síntesis química , Glucolípidos/aislamiento & purificación , Humanos , Espectrometría de Masas , Ratones , Estructura Molecular , Mycobacterium tuberculosis/química , Unión Proteica , Estereoisomerismo , Trehalosa/aislamiento & purificación
18.
Prep Biochem Biotechnol ; 50(1): 18-27, 2020.
Artículo en Inglés | MEDLINE | ID: mdl-31453751

RESUMEN

We report on the development of a functionalized membrane-based technology for selective enrichment of milk fat globules from raw bovine milk. Functionalization was conducted by in situ polymerization of acrylic acid within a polyvinylidene fluoride membrane, followed by the electrostatic attachment of a cationic polymer to impart a net positive charge. The functionalized membrane-based technology enabled a one-step method of selective separation of globules directly from milk-based on size and charge. The presence of globules in the eluate was confirmed by fluorescence microscopy. Quantification of the extracted phospholipids from globules in the eluant revealed a significantly higher amount of polar lipids than the permeate. Our study describes a comprehensive analysis of selective enrichment of fat globules using a functionalized membrane and demonstrates the beneficial effect of extracted phospholipids from enriched fat globules.


Asunto(s)
Glucolípidos/aislamiento & purificación , Glicoproteínas/aislamiento & purificación , Membranas Artificiales , Leche/química , Polivinilos/química , Animales , Bovinos , Fraccionamiento Químico/métodos , Glucolípidos/análisis , Glicoproteínas/análisis , Gotas Lipídicas , Fosfolípidos/análisis
19.
Clin Genet ; 97(4): 655-660, 2020 04.
Artículo en Inglés | MEDLINE | ID: mdl-31860127

RESUMEN

A total of 11 948 females suspicious of Fabry disease were tested by a combined biochemical and genetic approach. The enzyme activity, together with the concentration of lyso-GL-3 (lyso-Gb3) biomarker in dried blood spots (DBS), substantially improved the diagnostic detection of Fabry disease in females compared to the enzyme activity alone. Abnormal values for both were highly suspicious of Fabry disease (97% positive predictive value [PPV], similar to PPV in males). In cases with one abnormal biochemical value, elevated lyso-GL-3 is a far more important indicator than low enzyme activity (39% PPV vs 6% PPV). Cases with clearly negative results for both biochemical parameters are unlikely to have Fabry disease, even in clinically highly suspicious cases.


Asunto(s)
Biomarcadores/sangre , Enfermedad de Fabry/sangre , Glucolípidos/aislamiento & purificación , Esfingolípidos/aislamiento & purificación , Pruebas con Sangre Seca , Enfermedad de Fabry/genética , Enfermedad de Fabry/patología , Femenino , Glucolípidos/sangre , Humanos , Masculino , Mutación/genética , Esfingolípidos/sangre
20.
Braz. arch. biol. technol ; Braz. arch. biol. technol;63: e20180568, 2020. tab, graf
Artículo en Inglés | LILACS | ID: biblio-1132273

RESUMEN

Abstract Sophorolipids are glycolipids that have natural antimicrobial properties and present great potential in the pharmaceutical field. The present study aimed to produce sophorolipids from Candida bombicola using a chicken fat-based medium and evaluate the antimicrobial activity against Gram-negative (Proteus mirabilis, Escherichia coli, Salmonella enterica subsp. enterica) and Gram-positive bacteria (Enterococcus faecium, Staphylococcus aureus and Streptococcus mutans). The production of sophorolipids reached 27.86 g L-1. Based on the structural characterization, 73.55% of the sophorolipids present a mixture of acidic monoacetylated C18:2 and lactonic diacetylated C16:0, and 26.45% were present in the diacetylated C18:1 lactonic form. Bacteria submitted to sophorolipid exposure showed a reduction in viability at doses of 500 μg mL-1 and 2,000 μg mL-1 against Gram-positive and Gram-negative bacteria, respectively. These results suggest that sophorolipids produced in chicken fat medium may be used as antimicrobial agents to prevent or eliminate contamination by different pathogens.


Asunto(s)
Candida/metabolismo , Glucolípidos/farmacología , Enterococcus faecium/efectos de los fármacos , Bacterias Gramnegativas/efectos de los fármacos , Antibacterianos/farmacología , Proteus mirabilis/efectos de los fármacos , Glucolípidos/aislamiento & purificación , Salmonella enterica/efectos de los fármacos , Escherichia coli/efectos de los fármacos , Antibacterianos/aislamiento & purificación
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