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1.
Bioorg Chem ; 148: 107406, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38728907

ABSTRACT

Bacterial infections are the second leading cause of death worldwide, and the evolution and widespread distribution of antibiotic-resistance elements in bacterial pathogens exacerbate the threat crisis. Carbohydrates participate in bacterial infection, drug resistance and the process of host immune regulation. Numerous antimicrobials derived from carbohydrates or contained carbohydrate scaffolds that are conducive to an increase in pathogenic bacteria targeting, the physicochemical properties and druggability profiles. In the paper, according to the type and number of sugar residues contained in antimicrobial molecules collected from the literatures ranging from 2014 to 2024, the antimicrobial activities, action mechanisms and structure-activity relationships were delineated and summarized, for purpose to provide the guiding template to select the type and size of sugars in the design of oligosaccharide-based antimicrobials to fight the looming antibiotic resistance crisis.


Subject(s)
Anti-Bacterial Agents , Microbial Sensitivity Tests , Oligosaccharides , Structure-Activity Relationship , Oligosaccharides/chemistry , Oligosaccharides/pharmacology , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/chemical synthesis , Molecular Structure , Bacteria/drug effects , Humans , Monosaccharides/chemistry , Monosaccharides/pharmacology , Disaccharides/chemistry , Disaccharides/pharmacology
2.
Bioorg Med Chem ; 101: 117638, 2024 Mar 01.
Article in English | MEDLINE | ID: mdl-38394996

ABSTRACT

As a result of our continued efforts to pursue Gal-3 inhibitors that could be used to fully evaluate the potential of Gal-3 as a therapeutic target, two novel series of benzothiazole derived monosaccharides as potent (against both human and mouse Gal-3) and orally bioavailable Gal-3 inhibitors, represented by 4 and 5, respectively, were identified. These discoveries were made based on proposals that the benzothiazole sulfur atom could interact with the carbonyl oxygen of G182/G196 in h/mGal-3, and that the anomeric triazole moiety could be modified into an N-methyl carboxamide functionality. The interaction between the benzothiazole sulfur and the carbonyl oxygen of G196 in mGal-3 was confirmed by an X-ray co-crystal structure of early lead 9, providing a rare example of using a S···O binding interaction for drug design. It was found that for both the series, methylation of 3-OH in the monosaccharides caused no loss in h & mGal-3 potencies but significantly improved permeability of the molecules.


Subject(s)
Galectin 3 , Monosaccharides , Animals , Humans , Mice , Benzothiazoles/chemistry , Benzothiazoles/pharmacology , Drug Design , Galectin 3/antagonists & inhibitors , Galectins/antagonists & inhibitors , Monosaccharides/chemistry , Monosaccharides/pharmacology , Oxygen , Sulfur
3.
Int J Biol Macromol ; 263(Pt 1): 130173, 2024 Apr.
Article in English | MEDLINE | ID: mdl-38360238

ABSTRACT

Polysaccharides are biomolecules composed of monosaccharides that are widely found in animals, plants and microorganisms and are of interest for their various health benefits. Cumulative studies have shown that the modulation of radiation-induced apoptosis by polysaccharides can be effective in preventing and treating a wide range of radiation injuries with safety and few side effects. Therefore, this paper summarizes the monosaccharide compositions, molecular weights, and structure-activity relationships of natural polysaccharides that regulate radiation-induced apoptosis, and also reviews the molecular mechanisms by which these polysaccharides modulate radiation-induced apoptosis, primarily focusing on promoting cancer cell apoptosis to enhance radiotherapy efficacy, reducing radiation damage to normal tissues, and inhibiting apoptosis in normal cells. Additionally, the role of gut microbiota in mediating the interaction between polysaccharides and radiation is discussed, providing innovative ideas for various radiation injuries, including hematopoiesis, immunity, and organ damage. This review will contribute to a better understanding of the value of natural polysaccharides in the field of radiation and provide guidance for the development of natural radioprotective agents and radiosensitizers.


Subject(s)
Radiation Injuries , Radiation-Protective Agents , Radiation-Sensitizing Agents , Animals , Radiation-Protective Agents/pharmacology , Radiation Injuries/drug therapy , Radiation Injuries/prevention & control , Apoptosis , Polysaccharides/pharmacology , Monosaccharides/pharmacology
4.
J Biomol Struct Dyn ; 42(7): 3563-3567, 2024 Apr.
Article in English | MEDLINE | ID: mdl-37194429

ABSTRACT

Aspergillus favus (A. flavus) is a saprophytic fungus and a pathogen affecting several important foods and crops, including maize. A. flavus produces a toxic secondary metabolite called aflatoxin. Alpha-amylase (α-amylase), a hydrolytic enzyme produced by A. Flavus helps in the production of aflatoxin by hydrolysing the starch molecules in to simple sugars such as glucose and maltose. These simple sugars induce the production of aflatoxin. Inhibition of α-amylase has been proven as a potential way to reduce the production of aflatoxin. In the present study, we investigated the effect of selected carboxylic acid derivatives such as cinnamic acid (CA), 2, 4-dichlorophenoxyacetic acid (2,4-D), and 3-(4-hydroxyphenyl)-propionic acid (3,4-HPPA) on the fungal growth and for the α-amylase inhibitory activity. The binding potentials of these compounds with α-amylase have been confirmed by enzyme kinetics and isothermal titration calorimetry. Molecular docking and MD simulation studies were also performed to deduce the atomic level interaction between the protein and selected ligands. The results indicated that CA, 2,4-D and 3,4-HPPA can inhibit the fungal growth which could be partly due to the inhibition on fungal α-amylase activity.Communicated by Ramaswamy H. Sarma.


Subject(s)
Aflatoxins , Aspergillus flavus , Aspergillus flavus/metabolism , Molecular Docking Simulation , alpha-Amylases , Monosaccharides/metabolism , Monosaccharides/pharmacology , Carboxylic Acids/metabolism , Carboxylic Acids/pharmacology , 2,4-Dichlorophenoxyacetic Acid/metabolism , 2,4-Dichlorophenoxyacetic Acid/pharmacology
5.
Exp Cell Res ; 433(2): 113849, 2023 12 15.
Article in English | MEDLINE | ID: mdl-37926343

ABSTRACT

Estrogens have been demonstrated to inhibit age-related cognitive decline via binding to estrogen receptors (ERs). As a natural flavonoid component of Cuscuta Chinensis Lam., Kaempferol-3-O-glucoside (K-3-G) not only possesses anti-neuroinflammatory potential but also functions as an agonist for ERα and ERß. This study aimed to determine whether K-3-G improved cognition during the aging process, with an emphasis on its effect on microglial inflammation. In vivo, K-3-G (5 or 10 mg/kg/day) was orally given to the senescence-accelerated mouse prone 8 (SAMP8) mice from six to eight-month old. In addition to mitigating the memory and learning deficits of SAMP8 mice, K-3-G upregulated the expression of ERα and ERß in their hippocampal CA1 region, with the higher dose being more effective. Less Iba-1+ microglial cells presented in SAMP8 mice treated with K-3-G. The formation of NLR Family Pyrin Domain Containing 3 (NLRP3) complex, production of pro-inflammatory cytokines and oxidative stress-related markers, as well as expression of pro-apoptotic proteins were reduced by K-3-G. In vitro, BV2 microglial cells exposed to oligomeric amyloid beta (Aß)1-42 were treated with 100 µM K-3-G. K-3-G showed similar anti-inflammatory effects on BV2 cells as in vivo. K-3-G-induced alterations were partly diminished by fulvestrant, an ER antagonist. Moreover, dual-luciferase reporter system demonstrated that K-3-G induced ER expression by activating the transcription of estrogen-response elements (EREs). Collectively, these findings demonstrate that K-3-G may be a novel therapeutic agent for senescence-related cognitive impairment by inhibiting microglial inflammation through its action on ERs.


Subject(s)
Aging , Anti-Inflammatory Agents, Non-Steroidal , Cognitive Dysfunction , Estrogen Receptor alpha , Estrogen Receptor beta , Kaempferols , Monosaccharides , Receptors, Estrogen , Animals , Mice , Amyloid beta-Peptides/metabolism , Cognition , Cognitive Dysfunction/drug therapy , Estrogen Receptor alpha/metabolism , Estrogen Receptor beta/metabolism , Estrogens/metabolism , Inflammation/drug therapy , Inflammation/metabolism , Microglia/metabolism , Receptors, Estrogen/metabolism , Receptors, Estrogen/therapeutic use , Monosaccharides/pharmacology , Monosaccharides/therapeutic use , Kaempferols/pharmacology , Kaempferols/therapeutic use , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Anti-Inflammatory Agents, Non-Steroidal/therapeutic use
6.
Int J Biol Macromol ; 253(Pt 8): 127647, 2023 Dec 31.
Article in English | MEDLINE | ID: mdl-37884235

ABSTRACT

Aging is a degenerative progress, accompanied by oxidative damage, metabolic disorders and intestinal flora imbalance. Natural macromolecular polysaccharides have shown excellent anti-aging and antioxidant properties, while maintaining metabolic and intestinal homeostasis. The molecular weight, monosaccharide composition, infrared spectrum and other chemical structure information of four Rehmannia glutinosa polysaccharides (RG50, RG70, RG90, RGB) were determined, and their free radical scavenging ability was assessed. Molecular weight and monosaccharide composition analysis exhibited that RG50 (2-72 kDa), RG70 (3.2-37 kDa), RG70 (3-42 kDa), and RGB (3.1-180 kDa) were heteropolysaccharide with significant different monosaccharide species and molar ratios. We found that RG70 had the best antioxidant activity in vitro and RG70 could enhance the antioxidant enzyme system of Caenorhabditis elegans, diminished lipofuscin and reactive oxygen species levels, up-regulate the expression of daf-16, skn-1 and their downstream genes, and down-regulate the expression of age-1. Metabolomics results showed that RG70 mainly influenced glycine, serine and threonine metabolism and citric acid cycle. 16S rRNA sequencing showed that RG70 significantly up-regulated the abundance of Lachnospiraceae_NK4B4_group, which were positively correlated with amino acid metabolism and energy cycling. These results suggest that RG70 may delay aging by enhancing antioxidant effects, affecting probiotics and regulating key metabolic pathways.


Subject(s)
Gastrointestinal Microbiome , Rehmannia , Animals , Caenorhabditis elegans , Antioxidants/pharmacology , Antioxidants/chemistry , Rehmannia/chemistry , RNA, Ribosomal, 16S , Polysaccharides/pharmacology , Polysaccharides/chemistry , Aging , Monosaccharides/pharmacology
7.
Int J Biol Macromol ; 249: 126461, 2023 Sep 30.
Article in English | MEDLINE | ID: mdl-37619676

ABSTRACT

Boletus auripes is edible and medicinal boletus mushrooms rich in diverse nutrients and bioactive compounds, of which indigestible dietary polysaccharides are the most abundant compounds involved the regulation of gut microbes. However, the physicochemical, digestive, and fermentation characteristics of Boletus auripes polysaccharide (BAP) are not well studied. This study aimed to investigate the influence of different digestive stages on BAP's physicochemical characteristics and biological activities, and its effect on intestinal flora. We found that mannose (0.23 %), glucose (0.31 %), galactose (0.17 %), and fucose (0.19 %) were the main monosaccharides of BAP, with a high-molecular-weight (Mw) and a low-Mw fraction of 2084.83 and 62.93 kDa, respectively. During the course of digestion, there were slight alterations in the chemical composition, monosaccharide composition, and Mw of BAP. Despite these changes, the fundamental structural features of BAP remained largely unaffected. Moreover, the antioxidant and hypoglycemic activities of BAP were weakened under simulated saliva-gastrointestinal digestion. However, gut microbiota decomposed and utilized BAP to generate various short-chain fatty acids during fermentation, which decreased the pH of fecal cultures. Meanwhile, BAP modulated the gut microbiota composition and increased the relative abundance of Bacteroidetes. These findings suggest that BAP have potential for maintaining intestinal health and protecting against interrelated diseases.


Subject(s)
Gastrointestinal Microbiome , Fermentation , Digestion , Polysaccharides/pharmacology , Polysaccharides/chemistry , Fatty Acids, Volatile/pharmacology , Monosaccharides/pharmacology
8.
Int J Biol Macromol ; 237: 123844, 2023 May 15.
Article in English | MEDLINE | ID: mdl-36858091

ABSTRACT

Few studies reported the quality evaluation and gut microbiota regulation effect of polysaccharides from Fritillaria species. In this study, polysaccharides extracted from ten Fritillaria species were compared and distinguished through multi-levels evaluation strategy and data fusion. Furthermore, the gut microbiota regulation effect of polysaccharides among different species was analyzed and evaluated. The fingerprint profiling of IR, molecular weight distribution of polysaccharides, chromatogram of partially hydrolyzed polysaccharides (oligosaccharides) and completely hydrolyzed polysaccharides (monosaccharides) were similar, and no exclusive signals were observed. However, the signal strength of functional group, oligosaccharides abundance and monosaccharides proportion showed obvious differences in inter- and intra-species. Glucan may be the main component of polysaccharides in Fritillaria species, CIRR derived from CIR, PRZ, DEL, TAI, UNI possessed higher total polysaccharides content, polymerization degree, oligosaccharides abundance (DP 2-4), and glucose content than the others. Meanwhile, data fusion model was established for identification of affinis and multi-original species, the accuracy of which proved to be 100 %. In addition, Fritillaria polysaccharides could increase the bacterial community richness and diversity, regulate the gut microbiota composition and possessed potential therapeutic effects on gastrointestinal diseases and nervous system diseases.


Subject(s)
Fritillaria , Gastrointestinal Microbiome , Polysaccharides/pharmacology , Glucans/pharmacology , Monosaccharides/pharmacology
9.
Nutrients ; 14(19)2022 Oct 05.
Article in English | MEDLINE | ID: mdl-36235789

ABSTRACT

In recent decades, traditional eating habits have been replaced by a more globalized diet, rich in saturated fatty acids and simple sugars. Extensive evidence shows that these dietary factors contribute to cognitive health impairment as well as increase the incidence of metabolic diseases such as obesity and diabetes. However, how these nutrients modulate synaptic function and neuroplasticity is poorly understood. We review the Western, ketogenic, and paleolithic diets for their effects on cognition and correlations with synaptic changes, focusing mainly (but not exclusively) on animal model studies aimed at tracing molecular alterations that may contribute to impaired human cognition. We observe that memory and learning deficits mediated by high-fat/high-sugar diets, even over short exposure times, are associated with reduced arborization, widened synaptic cleft, narrowed post-synaptic zone, and decreased activity-dependent synaptic plasticity in the hippocampus, and also observe that these alterations correlate with deregulation of the AMPA-type glutamate ionotropic receptors (AMPARs) that are crucial to neuroplasticity. Furthermore, we explored which diet-mediated mechanisms modulate synaptic AMPARs and whether certain supplements or nutritional interventions could reverse deleterious effects, contributing to improved learning and memory in older people and patients with Alzheimer's disease.


Subject(s)
Cognition , Receptors, AMPA , Aged , Animals , Diet, High-Fat , Fatty Acids/metabolism , Glutamates/pharmacology , Hippocampus/metabolism , Humans , Monosaccharides/pharmacology , Neuronal Plasticity , Nutrients , Receptors, AMPA/metabolism , Sugars/metabolism , alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid/metabolism , alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid/pharmacology
10.
Int J Mol Sci ; 23(18)2022 Sep 18.
Article in English | MEDLINE | ID: mdl-36142831

ABSTRACT

The purpose of this study was to investigate the anti-fatigue effect of natural Lycium barbarum polysaccharide (LBP) during exercise, develop a functional anti-fatigue effervescent tablet by applying LBP to practical products, and help patients who have difficulty swallowing conventional tablets or capsules. LBP was extracted with water, and DEAE-52 cellulose was used for purification. The chemical structure and monosaccharide composition of LBP by Fourier transform infrared spectroscopy (FI-IR) and ion chromatography (IC). Lycium barbarum polysaccharide effervescent tablets (LBPT) were prepared by mixing LBP and an excipient. Animal experiments showed that LBP and LBPT significantly increased the exhaustive swimming time in rats. LBP and LBPT improved biochemical markers in rat serum, such as lactic acid and creatine kinase, enhanced the antioxidant capacity of rat muscle, and reversed the decrease in serum glucose, ATP and glycogen content caused by exercise. Transmission electron microscopy showed that LBP and LBPT increased the density of mitochondria in rat liver. In addition, molecular experiments showed that LBP and LBPT could improve oxidative stress caused by exercise by regulating the Nrf2/HO-1 signaling pathway and regulating energy metabolism via the AMPK/PGC-1α signaling pathway.


Subject(s)
Drugs, Chinese Herbal , Lycium , AMP-Activated Protein Kinases/metabolism , Adenosine Triphosphate/metabolism , Animals , Antioxidants/pharmacology , Cellulose/metabolism , Creatine Kinase/metabolism , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , Energy Metabolism , Excipients/pharmacology , Glucose/metabolism , Glycogen/metabolism , Lactic Acid/pharmacology , Lycium/metabolism , Monosaccharides/pharmacology , NF-E2-Related Factor 2/metabolism , Oxidative Stress , Rats , Tablets/pharmacology , Water/pharmacology
11.
Int J Mol Sci ; 23(15)2022 Aug 08.
Article in English | MEDLINE | ID: mdl-35955962

ABSTRACT

Autism spectrum disorder (ASD) is often associated with several intestinal and/or metabolic disorders as well as neurological manifestations such as epilepsy (ASD-E). Those presenting these neuropathological conditions share common aspects in terms of gut microbiota composition. The use of microbiota intervention strategies may be an approach to consider in the management of these cases. We describe the case of a 17-year-old girl affected by ASD, reduced growth, neurological development delay, mutations in the PGM1 and EEF1A2 genes (in the absence of clinically manifested disease) and, intestinal disorders such as abdominal pain and diarrhea associated with weight loss. As she demonstrated poor responsiveness to the therapies provided, we attempted two specific dietary patterns: a ketogenic diet, followed by a low fermentable oligosaccharides, disaccharides, monosaccharides and polyols (FODMAP) diet, with the aim of improving her neurological, metabolic, and intestinal symptoms through modulation of the gut microbiota's composition. The ketogenic diet (KD) provided a reduction in Firmicutes, Bacteroidetes, and Proteobacteria. Although her intestinal symptoms improved, KD was poorly tolerated. On the other hand, the passage to a low FODMAPs diet produced a significant improvement in all neurological, intestinal, and metabolic symptoms and was well-tolerated. The following gut microbiota analysis showed reductions in Actinobacteria, Firmicutes, Lactobacilli, and Bifidobacteria. The alpha biodiversity was consistently increased and the Firmicutes/Bacteroidetes ratio decreased, reducing the extent of fermentative dysbiosis. Gut microbiota could be a therapeutic target to improve ASD-related symptoms. Further studies are needed to better understand the correlation between gut microbiota composition and ASD, and its possible involvement in the physiopathology of ASD.


Subject(s)
Autism Spectrum Disorder , Autistic Disorder , Epilepsy , Gastrointestinal Microbiome , Irritable Bowel Syndrome , Adolescent , Autism Spectrum Disorder/microbiology , Diet, Carbohydrate-Restricted , Disaccharides/pharmacology , Epilepsy/therapy , Female , Humans , Irritable Bowel Syndrome/microbiology , Monosaccharides/pharmacology , Oligosaccharides/pharmacology , Peptide Elongation Factor 1
12.
Int J Pharm ; 625: 122039, 2022 Sep 25.
Article in English | MEDLINE | ID: mdl-35902059

ABSTRACT

Hepatospecific delivery by ligand based receptor targeting is an established strategy to augment therapy associated with liver diseases and disorders. Previously, we have investigated the effect of ligand headgroup on cellular uptake mediated by the asialoglycoprotein receptor by in silico and in vitro approach. In this paper, we report the design of agarose based liposomes for delivery to liver cancer cells and provide a proof of concept of the targeting efficiency against galactose liposomes using an in vivo approach. Sorafenib Tosylate loaded targeting liposomes were developed and optimized using factorial design. Comparative evaluation including cell cytotoxicity, pharmacokinetics and biodistribution and hepatospecific uptake was performed for both the liposomal systems. The formulations possessed a particle size of 150 - 180 nm and a zeta potential of 30 - 60 mV depending on the amount of ligand and drug loading, with more than 90% entrapment efficiency. A two-fold increase in cytotoxicity was observed with agarose-based liposomes as compared to galactose based liposomes. In vivo PK evaluation indicated a reduction in half life of drug when loaded in agarose ligand loaded system, probably due to greater uptake in the liver as evidenced in biodistribution study. Intrahepatic disposition revealed a higher PC/NPC uptake ratio with the targeted systems as compared to conventional liposomes, although the agarose-based system resulted in highest uptake ratio. A biocompatible platform for specific delivery of drugs to hepatocytes was established validating a rational approach to design liver targeting systems.


Subject(s)
Galactose , Liposomes , Drug Delivery Systems , Ligands , Liposomes/pharmacokinetics , Liver/metabolism , Monosaccharides/metabolism , Monosaccharides/pharmacology , Particle Size , Polysaccharides/pharmacology , Sepharose/metabolism , Sepharose/pharmacology , Sorafenib/pharmacology , Tissue Distribution
13.
Int J Biol Macromol ; 188: 245-252, 2021 Oct 01.
Article in English | MEDLINE | ID: mdl-34384800

ABSTRACT

To increase the value of yeast-fermented Korean liquor by-products, we obtained crude polysaccharide (CPS) fractions via ultrasound-assisted extraction and stepwise-gradient ethanol precipitation and investigated their functionality. Nitric oxide production in RAW 264.7 cells was increased following treatment with the CPSs derived from extract. Analysis of the monosaccharide and amino acid composition of the CPS fractions using HPLC revealed that the polysaccharides were mainly composed of glucose (57.2%), mannose (22.6%), and galactose (17.6%), and no amino acids were detected. In addition, a higher concentration of ethanol solvent for fractionation yielded polysaccharides with lower molecular weights (<15 kDa). CPS 3 and 4 fractions increased the production of TNF-α (15 and 17-fold, respectively) and IL-6 (20 and 18-fold, respectively) and iNOS (65 and 35-fold, respectively) expression at concentration 12.5 µg/mL compared with levels in non-treated RAW 264.7 cells. Especially, CPS 4 at 200 and 400 µg/mL significantly increased the proliferation of mouse spleen cells by 126% and 153%, respectively. These results indicated that CPS 4 enhanced the proliferation of mouse spleen cells in vivo, indicating its immune-enhancing effects. Therefore, this research can contribute to the development of eco-friendly extraction techniques and immune-enhancing materials.


Subject(s)
Monosaccharides/chemistry , Polysaccharides/chemistry , Saccharomyces cerevisiae/chemistry , Animals , Chemical Fractionation , Fermentation/drug effects , Mice , Molecular Weight , Monosaccharides/pharmacology , Nitric Oxide/chemistry , Nitric Oxide Synthase Type II/genetics , Polysaccharides/pharmacology , RAW 264.7 Cells , Republic of Korea , Saccharomyces cerevisiae/genetics , Tumor Necrosis Factor-alpha/genetics
14.
Int J Biol Macromol ; 188: 215-225, 2021 Oct 01.
Article in English | MEDLINE | ID: mdl-34371040

ABSTRACT

Extraction processes significantly alter the structural and functional properties of polysaccharides. In this study, we extracted polysaccharides from Chroogomphis rutilus fruiting bodies (designated as CRP) using four methods, including hot water, ultrasound, microwave and sequential ultrasound-microwave, and designated these polysaccharides as CRP-H, CRP-M, CRP-U and CRP-UM, respectively. All CRPs were heteropolysaccharides with semblable monosaccharide types of glucose, mannose and galactose, mainly constituted of α-d-glucopyranosyl-(1 â†’ 4). The extraction processes significantly affected the molecular weights, monosaccharide proportions, glycosidic bond ratios, branching degrees, triple-helix conformation and surface morphology of the CRPs. Among them, CRP-UM showed the highest yield and most potent antioxidative capacity in vitro and in HL-7702 cells, but the weakest activation of immunostimulatory response in RAW264.7 cells. In contrast, CRP-H exhibited the lowest yield but strongest immunostimulatory activity. Overall, microwave extraction could be utilized as a general and practical CRP extraction approach, based on its relatively high yield and bioactivities.


Subject(s)
Adjuvants, Immunologic/chemistry , Antioxidants/chemistry , Basidiomycota/chemistry , Polysaccharides/chemistry , Adjuvants, Immunologic/pharmacology , Animals , Antioxidants/pharmacology , Fruit/chemistry , Humans , Mannose/chemistry , Mice , Molecular Weight , Monosaccharides/chemistry , Monosaccharides/pharmacology , Plant Extracts/chemistry , Plant Extracts/pharmacology , Polysaccharides/isolation & purification , Polysaccharides/pharmacology , RAW 264.7 Cells , Water/chemistry
15.
Molecules ; 26(6)2021 Mar 19.
Article in English | MEDLINE | ID: mdl-33808719

ABSTRACT

Rare sugars are monosaccharides with a limited availability in the nature and almost unknown biological functions. The use of industrial enzymatic and microbial processes greatly reduced their production costs, making research on these molecules more accessible. Since then, the number of studies on their medical/clinical applications grew and rare sugars emerged as potential candidates to replace conventional sugars in human nutrition thanks to their beneficial health effects. More recently, the potential use of rare sugars in agriculture was also highlighted. However, overviews and critical evaluations on this topic are missing. This review aims to provide the current knowledge about the effects of rare sugars on the organisms of the farming ecosystem, with an emphasis on their mode of action and practical use as an innovative tool for sustainable agriculture. Some rare sugars can impact the plant growth and immune responses by affecting metabolic homeostasis and the hormonal signaling pathways. These properties could be used for the development of new herbicides, plant growth regulators and resistance inducers. Other rare sugars also showed antinutritional properties on some phytopathogens and biocidal activity against some plant pests, highlighting their promising potential for the development of new sustainable pesticides. Their low risk for human health also makes them safe and ecofriendly alternatives to agrochemicals.


Subject(s)
Agrochemicals , Crop Protection , Ecosystem , Monosaccharides , Plant Development/drug effects , Agrochemicals/chemistry , Agrochemicals/pharmacology , Monosaccharides/chemistry , Monosaccharides/pharmacology
16.
Mini Rev Med Chem ; 21(17): 2551-2566, 2021.
Article in English | MEDLINE | ID: mdl-33550971

ABSTRACT

Derivatives of monosaccharides and oligosaccharides play important roles in biological processes. Monosaccharides are the single carbohydrate building blocks, such as glucose, xylose, and fructose. Oligosaccharides are composed of 2-10 monosaccharides, including disaccharides and trisaccharides. Moreover, monosaccharides, oligosaccharides and their derivatives are vital molecules with various biological properties, including anticancer activity, antiviral activity, insecticidal activity, antimicrobial activity, and antioxidant activity. This review covers a survey of structural modifications, biological activities, and mechanisms of action of monosaccharides, oligosaccharides and their derivatives. Additionally, their structure-activity relationships are also concluded.


Subject(s)
Monosaccharides/chemistry , Monosaccharides/pharmacology , Oligosaccharides/chemistry , Oligosaccharides/pharmacology , Animals , Disaccharides/chemistry , Disaccharides/pharmacology , Fructose , Glucose , Humans , Xylose
17.
Vet Microbiol ; 252: 108908, 2021 Jan.
Article in English | MEDLINE | ID: mdl-33254056

ABSTRACT

The objective was to identify the active fractions of polysaccharide against replication of ALV-J and elucidate their structure activity relationship. The optimal extraction conditions were extracting temperature 90℃, pH 9 and the ratio of liquid to solid 30:1. Under these conditions, extraction yield of total polysaccharide was 6.5 % ± 0.19 %. Total polysaccharide was then purified by DEAE-52 cellulose and Sephadex G-200 gel. Three fractions, PPP-1, PPP-2, and PPP-3, were identified with molecular weight of 463.70, 99.41, and 26.97 kDa, respectively. Three polysaccharide fractions were all composed of 10 monosaccharides in different proportions. Compared with PPP-1, which was mainly composed of glucose, PPP-2 and PPP-3 contained a higher proportion of galactose, glucuronic acid and galacturonic acid. The Congo red assay indicated that the PPP-2 may have a triple helical structure, while PPP-1 and PPP-3 were absent. In vitro assay showed that there was no significant cytotoxicity among the polysaccharide fractions under the concentration of 800 µg mL-1 (P > 0.05). The antiviral test showed that PPP-2 had the strongest activity, indicating PPP-2 was the major antiviral component. The structure-activity relationship showed that the antiviral activities of polysaccharide fractions were affected by their monosaccharide composition, molecular weight, and triple helical structure, which was a result of a combination of multiple molecular structural factors. These results showed that the PPP-2 could be exploited as a valued product for replacing synthetic antiviral drugs, and provided support for future applications of polysaccharide from Pinus massoniana pollen as a useful source for antiviral agent.


Subject(s)
Antiviral Agents/pharmacology , Avian Leukosis Virus/drug effects , Avian Leukosis/drug therapy , Pinus/chemistry , Polysaccharides/pharmacology , Virus Replication/drug effects , Animals , Antiviral Agents/chemistry , Antiviral Agents/isolation & purification , Avian Leukosis/virology , Avian Leukosis Virus/physiology , Cell Line , Chick Embryo , Monosaccharides/chemistry , Monosaccharides/isolation & purification , Monosaccharides/pharmacology , Pollen/chemistry , Polysaccharides/chemistry , Polysaccharides/isolation & purification , Structure-Activity Relationship
18.
Int J Biol Macromol ; 168: 251-260, 2021 Jan 31.
Article in English | MEDLINE | ID: mdl-33309662

ABSTRACT

In this research, a novel polysaccharide (PCP) was extracted from Pleurotus citrinopileatus and purified by Sephadex G-150 gel column, and its antitumor activity was investigated using the model H22 tumor-bearing mice. PCP was found to be composed of arabinose, galactose, glucose, xylose, mannose and glucuronic acid in a proportion of 0.66: 14.59: 10.77: 1: 0.69: 0.23 with average molecular weight of 7.30 × 105 Da. Further analysis suggested that PCP was a pyranose with α-type and ß-type glycosidic residues. The antitumor assays in vivo indicated that PCP could effectively suppress H22 solid tumor growth, protect immune organs and improve inflammation and anemia. Besides, Annexin V-FITC/PI double staining and JC-1 staining demonstrated that PCP could induce apoptosis of H22 hepatoma cells. The PI staining assay revealed that PCP induced H22 hepatoma cells apoptosis by arresting cell cycle in S phase. These results suggest that the polysaccharide from Pleurotus citrinopileatus possesses potential value in the treatment of liver cancer.


Subject(s)
Pleurotus/metabolism , Polysaccharides/chemistry , Polysaccharides/isolation & purification , Animals , Antineoplastic Agents/pharmacology , Apoptosis/drug effects , Arabinose/pharmacology , Cell Cycle/drug effects , Cell Division/drug effects , China , Galactose/pharmacology , Glucuronic Acid/pharmacology , Glycosides/pharmacology , Liver Neoplasms/pathology , Male , Mannose/pharmacology , Mice , Molecular Weight , Monosaccharides/pharmacology , Polysaccharides/pharmacology , Xylose/pharmacology
19.
Bioorg Med Chem ; 29: 115854, 2021 01 01.
Article in English | MEDLINE | ID: mdl-33223464

ABSTRACT

Kinsenoside is the major bioactive component from herbal medicine with a broad range of pharmacological functions. Goodyeroside A, an epimer of kinsenoside, remains less explored. In this report we chemically synthesized kinsenoside, goodyeroside A and their analogues with glycan variation, chirality inversion at chiral center(s), and bioisosteric replacement of lactone with lactam. Among these compounds, goodyeroside A and its mannosyl counterpart demonstrated superior anti-inflammatory efficacy. Furthermore, goodyeroside A was found to suppresses inflammatory through inhibiting NF-κB signal pathway, effectively. Structure-activity relationship is also explored for further development of more promising kinsenoside analogues as drug candidates.


Subject(s)
4-Butyrolactone/analogs & derivatives , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Biological Products/pharmacology , Inflammation/drug therapy , Monosaccharides/pharmacology , NF-kappa B/antagonists & inhibitors , 4-Butyrolactone/chemical synthesis , 4-Butyrolactone/chemistry , 4-Butyrolactone/pharmacology , Animals , Anti-Inflammatory Agents, Non-Steroidal/chemical synthesis , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Biological Products/chemical synthesis , Biological Products/chemistry , Cell Survival/drug effects , Dose-Response Relationship, Drug , Inflammation/metabolism , Lipopolysaccharides/antagonists & inhibitors , Lipopolysaccharides/pharmacology , Mice , Molecular Structure , Monosaccharides/chemical synthesis , Monosaccharides/chemistry , NF-kappa B/metabolism , Nitric Oxide/antagonists & inhibitors , Nitric Oxide/biosynthesis , RAW 264.7 Cells , Signal Transduction/drug effects , Structure-Activity Relationship
20.
Carbohydr Polym ; 252: 117186, 2021 Jan 15.
Article in English | MEDLINE | ID: mdl-33183633

ABSTRACT

Pomelo fruitlets contain various active substances that are easily collected and processed. Here, the biological effects of pomelo fruitlet dietary fiber were investigated in vivo and in vitro. Total dietary fiber (TDF), soluble dietary fiber (SDF), and insoluble dietary fiber (IDF) values of pomelo fruitlets were 75.64 ± 3.65 %, 10.10 ± 1.39 %, and 62.48 ± 3.68 %, respectively. The main monosaccharides identified were rhamnose, arabinose, galactose, and glucose. All fibers scavenged free 2,2'-diphenyl-1-picrylhydrazyl radicals and reduced ferric cations. The water-holding, oil-holding, and swelling capacities of the fibers retarded glucose diffusion, inhibited α-amylase, and influenced cholesterol micelle formation. In a mouse model of alloxan-induced diabetes, SDF improved glucose tolerance, controlled blood glucose, and reduced serum insulin better than TDF or IDF. All fiber types decreased the total cholesterol content and the prevalence of Bacteroidetes, Proteobacteria, and Ruminococcaceae, but increased the abundance of Firmicutes, Lactobacillus, and Prevotellaceae in hyperglycemic mice.


Subject(s)
Citrus/chemistry , Diabetes Mellitus, Experimental/drug therapy , Dietary Fiber , Fruit/chemistry , Gastrointestinal Microbiome/drug effects , Monosaccharides , Animals , Blood Glucose , Cholesterol/blood , Dietary Fiber/pharmacology , Dietary Fiber/therapeutic use , Glycemic Control , Insulin/blood , Male , Mice , Monosaccharides/chemistry , Monosaccharides/pharmacology , Monosaccharides/therapeutic use , Solubility
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