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1.
J Ethnopharmacol ; 329: 118149, 2024 Jul 15.
Artigo em Inglês | MEDLINE | ID: mdl-38580188

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: Calcium oxalate crystals play a key role in the development and recurrence of kidney stones (also known as urolithiasis); thus, inhibiting the formation of these crystals is a central focus of urolithiasis prevention and treatment. Previously, we reported the noteworthy in vitro inhibitory effects of Aspidopterys obcordata fructo oligosaccharide (AOFOS), an active polysaccharide of the traditional Dai medicine Aspidopterys obcordata Hemsl. (commonly known as Hei Gai Guan), on the growth of calcium oxalate crystals. AIM OF THE STUDY: To investigated the effectiveness and mechanism of AOFOS in treating kidney stones. MATERIALS AND METHODS: A kidney stones rats model was developed, followed by examining AOFOS transport dynamics and effectiveness in live rats. Additionally, a correlation between the polysaccharide and calcium oxalate crystals was studied by combining crystallization experiments with density functional theory calculations. RESULTS: The results showed that the polysaccharide was transported to the urinary system. Furthermore, their accumulation was inhibited by controlling their crystallization and modulating calcium ion and oxalate properties in the urine. Consequently, this approach helped effectively prevent kidney stone formation in the rats. CONCLUSIONS: The present study emphasized the role of the polysaccharide AOFOS in modulating crystal properties and controlling crystal growth, providing valuable insights into their potential therapeutic use in managing kidney stone formation.


Assuntos
Oxalato de Cálcio , Cristalização , Cálculos Renais , Animais , Oxalato de Cálcio/química , Oxalato de Cálcio/metabolismo , Masculino , Ratos , Cálculos Renais/prevenção & controle , Cálculos Renais/tratamento farmacológico , Ratos Sprague-Dawley , Oligossacarídeos/farmacologia , Oligossacarídeos/química , Urolitíase/tratamento farmacológico , Urolitíase/prevenção & controle , Modelos Animais de Doenças , Inulina/química , Inulina/farmacologia
2.
Chem Biodivers ; 21(5): e202400506, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38507138

RESUMO

Acute lung injury (ALI) is a disease characterized by extensive lung damage and rampant inflammation, with a high mortality rate and no effective treatments available. Morinda officinalis oligosaccharides (MOOs), derived from the root of the traditional Chinese medicinal herb Morinda officinalis, known for its immune-boosting properties, presents a novel therapeutic possibility. To date, the impact of MOOs on ALI has not been explored. Our study aimed to investigate the potential protective effects of MOOs against ALI and to uncover the underlying mechanisms through an integrated approach of network pharmacology, molecular docking, and experimental validation. We discovered that MOOs significantly mitigated the pathological damage and decreased the expression of pro-inflammatory cytokines in LPS-induced ALI in mice. Complementary in vitro studies further demonstrated that MOOs effectively attenuated the M1 polarization induced by LPS. Network pharmacology analysis identified HSP90AA1, HSP90AB1, and NF-κB as key overlapping targets within a protein-protein interaction (PPI) network. Furthermore, Gene Ontology (GO) and Kyoto Encyclopedia of Genes and Genomes (KEGG) analyses elucidated the biological processes and signaling pathways implicated in MOOs' therapeutic action on ALI. Subsequently, molecular docking affirmed the binding of MOOs to the active sites of these identified targets. Corroborating these findings, our in vivo and in vitro experiments consistently demonstrated that MOOs significantly inhibited the LPS-induced upregulation of HSP90 and NF-κB. Collectively, these findings suggest that MOOs confer protection against ALI through a multi-target, multi-pathway mechanism, offering a promising new therapeutic strategy to mitigate this severe pulmonary condition.


Assuntos
Lesão Pulmonar Aguda , Lipopolissacarídeos , Simulação de Acoplamento Molecular , Morinda , Oligossacarídeos , Lesão Pulmonar Aguda/tratamento farmacológico , Lesão Pulmonar Aguda/induzido quimicamente , Lesão Pulmonar Aguda/metabolismo , Lesão Pulmonar Aguda/patologia , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Animais , Morinda/química , Camundongos , Oligossacarídeos/farmacologia , Oligossacarídeos/química , Oligossacarídeos/isolamento & purificação , Masculino , Células RAW 264.7 , Camundongos Endogâmicos C57BL , Citocinas/metabolismo , NF-kappa B/metabolismo
3.
Carbohydr Res ; 538: 109076, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38537364

RESUMO

Profiling of pectic arabinans and galactans by analysis of the released oligosaccharides after backbone cleavage provides information on the complexity of the polymer structure. In plants of the family Amaranthaceae, arabinan and galactan substitution with ferulates extends the polysaccharide complexity, changing its chemical properties. Knowledge of the ferulate environment is crucial to understand structure-function-relationships of feruloylated pectins. Here, we present an approach to separate enzymatically generated feruloylated and non-feruloylated arabino- and galactooligosaccharides, followed by deesterification and semiquantitative analysis by HPAEC-PAD using previously reported relative response factors. Application of this approach to sugar beet pectins and insoluble and soluble dietary fiber preparations of amaranth and quinoa suggests that ferulates are preferably incorporated into more complex structures, as nicely demonstrated for feruloylated galactans. Also, ferulate substitution appears to negatively affect enzymatic cleavage by using endo-enzymes. As a consequence, we were able to tentatively identify new feruloylated tri- and tetrasaccharides of galactans isolated from sugar beet pectins.


Assuntos
Galactanos , Pectinas , Polissacarídeos , Galactanos/química , Pectinas/química , Oligossacarídeos/química , Cromatografia , Açúcares
4.
Carbohydr Polym ; 327: 121675, 2024 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-38171687

RESUMO

Human milk oligosaccharides, including free oligosaccharides and glycoconjugates, exert a key role in neonatal health and development. Changes in free oligosaccharides of milk from different ethnic groups have been documented. In this study, human milk was collected from Han, Hui, and Tibetan populations in northwest China, and differences in N/O-glycome among these three ethnic groups were systematically compared using online high-performance liquid chromatography-tandem mass spectrometry. Among the 63 detected N-glycans, 35 showed significant differences between the three ethnic groups (p < 0.05). Among the 70 detected O-glycans, four neutral O-glycans and six acidic O-glycans exhibited significant differences among the three ethnic groups (p < 0.05), with six acidic O-glycans reported for the first time. Overall, the extent of milk N/O-glycosylation was higher in the Han population than in the Hui or Tibetan groups. This trend was particularly pronounced for the main sialylated N/O-glycans. Except for sulfated O-glycans, which were higher in the milk from Tibetan mothers, the other types of N/O-glycans were present in similar proportions across all ethnic groups. Understanding the composition of N/O-glycans in human milk can help research on the structure-function relationship of glycans.


Assuntos
Colostro , Espectrometria de Massas em Tandem , Feminino , Gravidez , Recém-Nascido , Humanos , Espectrometria de Massas em Tandem/métodos , Colostro/química , Etnicidade , Leite Humano/química , Polissacarídeos/química , Oligossacarídeos/química
5.
Carbohydr Polym ; 329: 121789, 2024 Apr 01.
Artigo em Inglês | MEDLINE | ID: mdl-38286556

RESUMO

Pectin, predominantly present within plant cell walls, is a dietary fiber that potentially induces distinct health effects depending on its molecular structure. Such structure-dependent health effects of pectin-derived galacturonic acid oligosaccharides (GalA-OS) are yet largely unknown. This study describes the influence of methyl-esterification and ∆4,5-unsaturation of GalA-OS through defined sets of GalA-OS made from pectin using defined pectinases, on the fermentability by individual fecal inocula. The metabolite production, OS utilization, quantity and size, methyl-esterification and saturation of remaining GalA-OS were monitored during the fermentation of GalA-OS. Fermentation of all GalA-OS predominantly induced the production of acetate, butyrate and propionate. Metabolization of unsaturated GalA-OS (uGalA-OS) significantly increased butyrate formation compared to saturated GalA-OS (satGalA-OS), while satGalA-OS significantly increased propionate formation. Absence of methyl-esters within GalA-OS improved substrate metabolization during the first 18 h of fermentation (99 %) compared to their esterified analogues (51 %). Furthermore, HPAEC and HILIC-LC-MS revealed accumulation of specific methyl-esterified GalA-OS, confirming that methyl-esterification delays fermentation. Fermentation of structurally distinct GalA-OS results in donor specific microbiota composition with uGalA-OS specifically stimulating the butyrate-producer Clostridium Butyricum. This study concludes that GalA-OS fermentation induces highly structure-dependent changes in the gut microbiota, further expanding their potential use as prebiotics.


Assuntos
Pectinas , Propionatos , Fermentação , Pectinas/química , Oligossacarídeos/química , Fezes , Butiratos
6.
Int J Biol Macromol ; 256(Pt 1): 128260, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-38000618

RESUMO

Pectinases are outstanding multienzymes, which have the potential to produce new emerging pectic-oligosaccharides (POS) via enzymatic hydrolysis of pectin. However, free pectinase is unable to undergo repeated reaction for the production of POS. This study proposed a sustainable biocatalyst of pectinases known as cross-linked pectinase aggregates (CLPA). Pectinase from Aspergillus aculeatus was successfully precipitated using 2 mg/mL pectinase and 60 % acetone for 20 min at 20 °C, which remained 36.3 % of its initial activity. The prepared CLPA showed the highest activity recovery (85.0 %), under the optimised conditions (0.3 % (v/v) starch and glutaraldehyde mixture (St/Ga), 1.5: 1 of St/Ga, 25 °C, 1.5 h). Furthermore, pectin-degrading enzymes from various sources were used to produce different CLPA. The alteration of pectinase secondary structure gave high stability in acidic condition (pH 4), thermostability, deactivation energy and half-life, and improved storage stability at 4 °C for 30 days. Similarly to their free counterpart, the CLPA exhibited comparable enzymatic reaction kinetics and could be reused eight times with approximately 20 % of its initial activity. The developed CLPA does not only efficaciously produced POS from pectin as their free form, but also exhibited better operational stability and reusability, making it more suitable for POS production.


Assuntos
Pectinas , Poligalacturonase , Pectinas/química , Hidrólise , Oligossacarídeos/química
7.
Phytochemistry ; 217: 113922, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-37972675

RESUMO

The jalap roots, Operculina hamiltonii D.F. Austin & Staples (Convolvulaceae), are extensively commercialized as a depurative and laxative remedy in traditional medicine of the north and northeast regions of Brazil. The purification by recycling HPLC and structure elucidation of three new acyl sugars or resin glycosides are described here from a commercial product made of powdered roots. Three macrocyclic structures of a tetrasaccharide of (11S)-hydroxyhexadecanoic acid, operculinic acid C (1), the undescribed hamiltonins II and III (3 and 4), in addition to the known batatinoside III (5), presented a diastereoisomeric relationship as one residue of n-dodecanoic acid esterified the oligosaccharide core on a different position in each compound. Furthermore, hamiltonin IV (6) was characterized as an ester-type homodimer of acylated operculinic acid C with the same substitution pattern identified in hamiltonins II (3) and III (4) for each of the dimer subunits. All the isolated resin glycosides did not display any intrinsic cytotoxicity (IC50 > 25 µM). However, a combination of the individual isolated compounds 3-6 (1-50 µM) demonstrated an enhancement of cytotoxic effects with sublethal doses of vinblastine and podophyllotoxin (0.003 µM) in multidrug-resistant breast carcinoma epithelial cells (MCF-7/Vin).


Assuntos
Convolvulaceae , Neoplasias , Humanos , Células MCF-7 , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Convolvulaceae/química , Glicosídeos/farmacologia , Glicosídeos/química , Resinas Vegetais/química , Oligossacarídeos/química , Oligossacarídeos/farmacologia
8.
Food Res Int ; 173(Pt 1): 113288, 2023 11.
Artigo em Inglês | MEDLINE | ID: mdl-37803601

RESUMO

Coffee oligosaccharides (COS) are novel sources of prebiotics comprising manno-oligosaccharides, galacto-oligosaccharides, arabinoxylan-oligosaccharides, and cello-oligosaccharides. These oligosaccharides function as prebiotics, antioxidant-dietary fiber owing to important physicochemical and physiological properties, adjuvants, pharma, nutraceutical food, gut health, immune system boosting, cancer treatment, and many more. Research suggests COS performs prebiotic action, as it enhances gut health by promoting beneficial bacteria in the colon and releasing functional metabolites such as SCFAs. However, research on COS concerning other metabolic illnesses is still lacking. Among various production strategies, pretreatment and enzymatic hydrolysis are preferred for the production of COS. Functional oligosaccharides can add value to coffee waste and reduce the environmental impact of coffee manufacturing, besides providing more options for healthy and active ingredients. This review updates COS, production, bio-activity, their role as a functional food, food supplements/natural food additives, prebiotics and many applications of health sectors. Research is desirable to extend information on COS and their bio-activity, besides in vivo and clinical trials, to assess their effects in prior human formulations into the food and therapeutic arena.


Assuntos
Café , Prebióticos , Humanos , Suplementos Nutricionais , Oligossacarídeos/química , Fibras na Dieta
9.
J Sci Food Agric ; 103(15): 7569-7579, 2023 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-37418584

RESUMO

BACKGROUND: Hemicellulose extraction from lignocellulosic biomasses has gained interest over the years, and hydrothermal treatment is one of the most common methods employed for this purpose. This work aimed to deeply study hazelnut (Corylus avellana L.) shells as a new source of dietary fibre, evaluating the effect of hydrothermal treatment temperatures on the type and structure of fibre extracted, but also on the formation of side-products derived from lignocellulose degradation. RESULTS: Different process temperatures led to diverse polysaccharides in the hydrothermal extract. Pectin was identified for the first time in hazelnut shells when experimenting with extraction at 125 °C, whereas at 150 °C a heterogeneous mixture of pectin, xylan, and xylo-oligosaccharides was present. The highest yield in terms of total fibre was gained at 150 and 175 °C, and then decreased again at 200 °C. Finally, more than 500 compounds from different chemical classes were putatively identified and they appeared to be present in the extracted fibre with a different distribution and relative amount, depending on the heat treatment severity. A generally high content of phenols, phenyls, oligosaccharides, dehydro-sugars, and furans was observed. CONCLUSIONS: Modulation of the hydrothermal treatment temperature allows fibre extracts with very different compositions, and therefore different potential end uses, to be obtained from hazelnut shells. A sequential temperature-based fractionation approach, as a function of the severity of the extraction parameters, can also be considered. Nevertheless, the study of the side-compounds formed from lignocellulosic matrix degradation, as a function of the applied temperature, needs to be fully addressed for a safe introduction of the fibre extract within the food chain. © 2023 The Authors. Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.


Assuntos
Corylus , Corylus/química , Temperatura , Pectinas/metabolismo , Oligossacarídeos/química , Fibras na Dieta/metabolismo
10.
Molecules ; 28(9)2023 Apr 27.
Artigo em Inglês | MEDLINE | ID: mdl-37175170

RESUMO

Agronomic practices and the winemaking process lead to the production of considerable quantities of waste and by-products. These are often considered waste with negative effects on environmental sustainability. However, vine shoots and grape stalks can be reused, representing a potential source of xylo-oligosaccharides and polyphenols. In this context, the purpose of this work was to obtain enriched extracts using three different autohydrolysis treatments with (i) H2O, (ii) H2O:EtOH, and (iii) H2O:Amberlyst. The obtained extracts were characterized by their xylo-oligosaccharide and polyphenol profiles using LC-MS techniques. The use of ethanol during autohydrolysis allowed for greater extraction of xylan-class compounds, especially in vine shoot samples, while an increase in antioxidant activity (128.04 and 425.66 µmol TE/g for ABTS and DPPH, respectively) and in total phenol content (90.92 mg GAE/g) was obtained for grape stalks.


Assuntos
Vitis , Vitis/química , Fenóis , Oligossacarídeos/química , Polifenóis , Extratos Vegetais/química , Antioxidantes/farmacologia , Etanol
11.
Food Chem ; 419: 136098, 2023 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-37031538

RESUMO

An efficient decolorization method for ginseng residue oligosaccharides (GROs) using ultrasound-assisted D392 macroporous resin was developed. The decolorization effects and color differences of activated carbon adsorption, hydrogen peroxide oxidation, and resin adsorption were evaluated. The optimal conditions of the three decolorization methods for static, dynamic, ultrasound-assisted resin adsorption were compared. The results showed that ultrasound-assisted decolorization had the best decolorization effect of greatly decreasing the decolorization time to 80 min. Color difference analysis revealed the process of pigment removal during GRO decolorization. The UV-visible full-wavelength scan showed that most pigments were removed after decolorization. The characterizations by the Fourier-transform infrared spectroscopy and X-ray diffraction analysis showed that the chemical structure and crystallinity of the GROs did not change upon decolorization. In addition, the molecular weight distribution did not change significantly. This research contributes to further exploration of the structures and functions of GROs.


Assuntos
Panax , Porosidade , Panax/química , Ultrassom , Oligossacarídeos/química , Cor
12.
Int J Biol Macromol ; 236: 123935, 2023 May 01.
Artigo em Inglês | MEDLINE | ID: mdl-36894060

RESUMO

The slug Vaginulus alte is used as folk medicine in China, but the structure and activities of its galactan components remain to be clarified. Here, the galactan from V. alte (VAG) was purified. The Mw of VAG was determined as ~28.8 kDa. Chemical composition analysis showed that VAG was composed of d-galactose (75 %) and l-galactose (25 %). To elucidate its precise structure, a series of disaccharides and trisaccharides were purified from mild acid hydrolyzed VAG and their structures were characterized by 1D/2D NMR spectroscopy. Based on methylation analysis and structural analysis of oligosaccharides, VAG was elucidated as a highly branched polysaccharide and mainly composed of (1 â†’ 6)- or (1 â†’ 3)-linked ß-d-galactose, and distinct (1 â†’ 2)-linked α-l-galactose. The investigation of probiotic effects in vitro revealed that VAG could promote the growth of B. thetaiotaomicron and B. ovatus, while had no effect on the growth of L. acidophilus, L. rhamnosus, B. longum subsp. infantis and B. animalis subsp. lactis, but dVAG-3 with Mw ~1.0 kDa could promote the growth of L. acidophilus. These results will provide insights into specific structures and functions of polysaccharides from the V. alte.


Assuntos
Microbioma Gastrointestinal , Gastrópodes , Animais , Humanos , Galactanos/química , Galactose , Oligossacarídeos/química , Polissacarídeos
13.
Int J Mol Sci ; 24(5)2023 Feb 28.
Artigo em Inglês | MEDLINE | ID: mdl-36902109

RESUMO

κ-Selenocarrageenan (KSC) is an organic selenium (Se) polysaccharide. There has been no report of an enzyme that can degrade κ-selenocarrageenan to κ-selenocarrageenan oligosaccharides (KSCOs). This study explored an enzyme, κ-selenocarrageenase (SeCar), from deep-sea bacteria and produced heterologously in Escherichia coli, which degraded KSC to KSCOs. Chemical and spectroscopic analyses demonstrated that purified KSCOs in hydrolysates were composed mainly of selenium-galactobiose. Organic selenium foods through dietary supplementation could help regulate inflammatory bowel diseases (IBD). This study discussed the effects of KSCOs on dextran sulfate sodium (DSS)-induced ulcerative colitis (UC) in C57BL/6 mice. The results showed that KSCOs alleviated the symptoms of UC and suppressed colonic inflammation by reducing the activity of myeloperoxidase (MPO) and regulating the unbalanced secretion of inflammatory cytokines (tumor necrosis factor (TNF)-α, interleukin (IL)-6 and IL-10). Furthermore, KSCOs treatment regulated the composition of gut microbiota, enriched the genera Bifidobacterium, Lachnospiraceae_NK4A136_group and Ruminococcus and inhibited Dubosiella, Turicibacter and Romboutsia. These findings proved that KSCOs obtained by enzymatic degradation could be utilized to prevent or treat UC.


Assuntos
Carragenina , Colite Ulcerativa , Microbioma Gastrointestinal , Compostos Organosselênicos , Animais , Camundongos , Colite Ulcerativa/prevenção & controle , Colite Ulcerativa/terapia , Sulfato de Dextrana , Modelos Animais de Doenças , Microbioma Gastrointestinal/efeitos dos fármacos , Interleucina-6/metabolismo , Camundongos Endogâmicos C57BL , Oligossacarídeos/química , Oligossacarídeos/farmacologia , Oligossacarídeos/uso terapêutico , Fator de Necrose Tumoral alfa/metabolismo , Carragenina/farmacologia , Carragenina/uso terapêutico , Compostos Organosselênicos/farmacologia , Compostos Organosselênicos/uso terapêutico
14.
Pediatr Neonatol ; 64(3): 231-238, 2023 05.
Artigo em Inglês | MEDLINE | ID: mdl-36642576

RESUMO

Based on its richness in immune-related components such as human milk, human milk oligosaccharides (HMOs), milk proteins, and lipids, breast milk can be considered the first functional food that humans encounter in their lifetime. According to WHO recommendations breast milk has to be the only food in an infant's diet in the first six months of age which is then continued up to two years of age with the suitable complementary foods. Regarding breast milk balanced composition, it is considered as the best food of infants thus many studies have been carried out to determine the benefits of breast milk. Based on numerous studies breast milk have a tendency to reduce the risk of type 2 diabetes, obesity, allergies, celiac disease, necrotizing enterocolitis (NEC), gastrointestinal tract infections and some type of cancers. The benefits of breast milk can be explained by its special combination which includes; macronutrients, micronutrients and bioactive components such as immunoglobulins, hormones, growth factors and oligosaccharides. One of the essential bioactive compounds of breast milk is known as human milk oligosaccharides (HMOs). HMOs are unique, bioactive carbohydrates which are identified as the most significant components of breast milk. Since they have structural complexity and multifunctional properties, they are one of the most wondered components of breast milk. HMOs promote the development of the neonatal intestinal immune, and nervous systems. This article briefly describes the history, complex structure and different functions of HMOs and highlight the importance of maternal diet for HMO biosynthesis.


Assuntos
Diabetes Mellitus Tipo 2 , Leite Humano , Lactente , Feminino , Recém-Nascido , Humanos , Leite Humano/química , Prebióticos/análise , Diabetes Mellitus Tipo 2/metabolismo , Intestinos , Oligossacarídeos/análise , Oligossacarídeos/química , Oligossacarídeos/metabolismo
15.
Front Immunol ; 14: 1327853, 2023.
Artigo em Inglês | MEDLINE | ID: mdl-38179055

RESUMO

Introduction: Human milk contains structurally diverse oligosaccharides (HMO), which are multifunctional modulators of neonatal immune development. Our objective was to investigate formula supplemented with fucosylated (2'FL) + neutral (lacto-N-neotetraose, LNnt) oligosaccharides and/or sialylated bovine milk oligosaccharides (BMOS) on immunological outcomes. Methods: Pigs (n=46) were randomized at 48h of age to four diets: sow milk replacer formula (CON), BMOS (CON + 6.5 g/L BMOS), HMO (CON + 1.0 g/L 2'FL + 0.5 g/L LNnT), or BMOS+HMO (CON + 6.5 g/L BMOS + 1.0 g/L 2'FL + 0.5 g/L LNnT). Blood and tissues were collected on postnatal day 33 for measurement of cytokines and IgG, phenotypic identification of immune cells, and ex vivo lipopolysaccharide (LPS)-stimulation of immune cells. Results: Serum IgG was significantly lower in the HMO group than BMOS+HMO but did not differ from CON or BMOS. The percentage of PBMC T-helper cells was lower in BMOS+HMO than the other groups. Splenocytes from the BMOS group secreted more IL-1ß when stimulated ex vivo with LPS compared to CON or HMO groups. For PBMCs, a statistical interaction of BMOS*HMO was observed for IL-10 secretion (p=0.037), with BMOS+HMO and HMO groups differing at p=0.1. Discussion: The addition of a mix of fucosylated and sialylated oligosaccharides to infant formula provides specific activities in the immune system that differ from formulations supplemented with one oligosaccharide structure.


Assuntos
Leucócitos Mononucleares , Lipopolissacarídeos , Lactente , Humanos , Animais , Feminino , Suínos , Lipopolissacarídeos/análise , Oligossacarídeos/farmacologia , Oligossacarídeos/química , Leite Humano/química , Citocinas/análise , Linfócitos T Auxiliares-Indutores , Suplementos Nutricionais , Imunoglobulina G/análise
16.
Carbohydr Polym ; 298: 120072, 2022 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-36241268

RESUMO

Stichopus monotuberculatus is a tropical sea cucumber species and used as a folk medicine and tonic food. In this study, a fucosylated glycosaminoglycan (SmFG), the depolymerized SmFG (dSmFG) and its oligosaccharide fractions were prepared. The SmFG and its depolymerized products were comprised of a chondroitin-sulfate-E backbone, and various sulfated fucose side chains, including an unusual disaccharide side chain connected to the C-3 position of D-glucuronic acid (GlcA) or GlcA-ol. A peeling reaction occurred during the deaminative depolymerization process. The dSmFG and its fractions showed strong anticoagulant activity by selectively inhibiting intrinsic tenase complex, and had no anti-factor IIa, Xa and VIIa activity. The anticoagulant activity reduced with the decrease of molecular weight, and the unusual branch and novel reducing end may enhance the anticoagulant activity. These findings can provide significant information for development and utilization of depolymerized products from SmFG in food and pharmaceutical industries.


Assuntos
Glicosaminoglicanos , Pepinos-do-Mar , Animais , Anticoagulantes/química , Anticoagulantes/farmacologia , Sulfatos de Condroitina/química , Dissacarídeos , Fucose/química , Ácido Glucurônico , Glicosaminoglicanos/química , Glicosaminoglicanos/farmacologia , Oligossacarídeos/química , Pepinos-do-Mar/química , Sulfatos
17.
J Nat Prod ; 85(10): 2385-2394, 2022 10 28.
Artigo em Inglês | MEDLINE | ID: mdl-36162138

RESUMO

Operculina hamiltonii is a vine native to the north and northeast region of Brazil, where its roots are traded as a depurative and laxative remedy with the name of Brazilian jalap in traditional medicine. Procedures for the isolation, purification by recycling HPLC, and structure elucidation of three undescribed resin glycosides are presented herein. Hamiltonin I (1) represents a macrocyclic structure of a tetrasaccharide of (11S)-hydroxyhexadecanoic acid. Additionally, two acyclic pentasaccharides, named hamiltoniosides I (2) and II (3), were also isolated, which are related structurally to the known compounds 4 and 5, macrocyclic lactone-type batatinosides. The tetrasaccharide core of 1 was diacylated by n-decanoic acid and the unusual n-hexadecanoic acid moiety, while the pentasaccharides 2-5 were esterified by one unit of n-decanoic or n-dodecanoic acid. All the isolated compounds were found to be inactive as cytotoxic agents. However, when they were evaluated (1-25 µM) in combination with a sublethal concentration of the anticancer agent vinblastine (0.003 µM), a significant enhancement of the resultant cytotoxicity was produced, especially for multidrug-resistant breast carcinoma epithelial cells. Such combined synergistic potency may be beneficial for chemotherapy, making resin glycosides potential candidates for drug repurposing of conventional chemotherapeutic drugs to reduce their side effects.


Assuntos
Convolvulaceae , Neoplasias , Humanos , Glicosídeos/farmacologia , Glicosídeos/química , Vimblastina/farmacologia , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Resinas Vegetais/química , Oligossacarídeos/química
18.
Carbohydr Res ; 519: 108627, 2022 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-35803019

RESUMO

This study reports the enzymatic upgrading of fucosylated xyloglucan from depectinized citrus residues into 2'-fucosyllactose, a fucosylated human milk oligosaccharide. Alkaline and enzymatic xyloglucan extractions were compared. Of the original fucose present in the depectinized residues of lemon and orange, 35-36% and 48-51% were extracted as fucosylated xyloglucan by enzyme- or alkaline treatment, respectively. Furthermore, the enzymatically extracted xyloglucan structures had a narrower molecular weight distribution around 1 kDa, contrary to a more polydisperse distribution of the alkaline extracted xyloglucans, ranging from 1 to 500 kDa. The applicability of the fucosylated-xyloglucan extracts in transfucosylation reactions, was determined by use of a selected fungal fucosidase, resulting in yields of 10.2-11.4% enzymatic extracts, and 6.5-7.4% for alkaline extracts (orange and lemon respectively). The results demonstrate that depectinized citrus side streams are a useful source of fucosylated xyloglucan, preferably extracted by an enzyme catalyzed approach.


Assuntos
Leite Humano , Pectinas , Fucose/química , Humanos , Leite Humano/química , Oligossacarídeos/química , Xilanos
19.
Compr Rev Food Sci Food Saf ; 21(4): 3033-3095, 2022 07.
Artigo em Inglês | MEDLINE | ID: mdl-35765769

RESUMO

Garlic is a common food, and many of its biological functions are attributed to its components including functional carbohydrates. Garlic polysaccharides and oligosaccharides as main components are understudied but have future value due to the growing demand for bioactive polysaccharides/oligosaccharides from natural sources. Garlic polysaccharides have molecular weights of 1 × 103 to 2 × 106  Da, containing small amounts of pectins and fructooligosaccharides and large amounts of inulin-type fructans ((2→1)-linked ß-d-Fruf backbones alone or with attached (2→6)-linked ß-d-Fruf branched chains). This article provides a detailed review of research progress and identifies knowledge gaps in extraction, production, composition, molecular characteristics, structural features, physicochemical properties, bioactivities, and structure-function relationships of garlic polysaccharides/oligosaccharides. Whether the extraction processes, synthesis approaches, and modification methods established for other non-garlic polysaccharides are also effective for garlic polysaccharides/oligosaccharides (to preserve their desired molecular structures and bioactivities) requires verification. The metabolic processes of ingested garlic polysaccharides/oligosaccharides (as food ingredients/dietary supplements), their modes of action in healthy humans or populations with chronic conditions, and molecular/chain organization-bioactivity relationships remain unclear. Future research directions related to garlic polysaccharides/oligosaccharides are discussed.


Assuntos
Alho , Antioxidantes , Alho/química , Humanos , Oligossacarídeos/química , Oligossacarídeos/farmacologia , Polissacarídeos/química , Polissacarídeos/farmacologia , Relação Estrutura-Atividade
20.
J Agric Food Chem ; 70(16): 5207-5217, 2022 Apr 27.
Artigo em Inglês | MEDLINE | ID: mdl-35434993

RESUMO

Human milk oligosaccharides (HMOs) are the second most abundant carbohydrates in colostrum. In this study, we performed a quantitative analysis of 13 oligosaccharides in 99 colostrum samples obtained from mothers living in Northwest China. The analysis combined liquid chromatography-mass spectrometry (LC-MS) with 2-amino-N-(2-aminoethyl)benzamide (AEAB) labeling and nonsecretors accounted for 17%. Compared with healthy secretor mothers, those with gestational diabetes mellitus presented lower levels of sialylated oligosaccharides, especially 3'-sialyllactose. Colostrum from mothers with pregnancy-induced hypertension had higher levels of fucosylated oligosaccharides, but the difference was not significant, and hypothyroidism appeared to have no effect on HMOs. Most HMOs (especially 6'-sialyllactose) were more abundant in colostrum from mothers who underwent vaginal delivery than a C-section. These findings show that the concentration of total or individual HMOs is affected by multiple factors. These findings provide a reference for evaluating variations in HMO expression among different populations and potential guidance for providing personalized clinical nutrition.


Assuntos
Leite Humano , Oligossacarídeos , Cromatografia Líquida , Colostro/química , Feminino , Humanos , Leite Humano/química , Mães , Oligossacarídeos/química , Gravidez
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