388 results on '"rhamnose"'
Search Results
2. A sustainable and efficient strategy for bioconverting naringin to L-rhamnose, 2R-naringenin, and kaempferol.
- Author
-
Lu M, Liu S, Liu J, Zhao L, and Pei J
- Subjects
- Kaempferols, Rhamnose, Flavanones
- Abstract
The development of a sustainable and efficient bioconversion strategy is crucial for the full-component utilization of naringin. In this study, an engineering Pichia pastoris co-culture system was developed to produce L-rhamnose and 2S/2R-naringenin. By optimizing transformation conditions, the co-culture system could completely convert naringin while fully consuming glucose. The production of 2S/2R-naringenin reached 59.5 mM with a molar conversion of 99.2%, and L-rhamnose reached 59.1 mM with a molar conversion of 98.5%. In addition, an engineering Escherichia coli co-culture system was developed to produce 2R-naringenin and kaempferol from 2S/2R-naringenin. Maximal kaempferol production reached 1050 mg/L with a corresponding molar conversion of 99.0%, and 996 mg/L 2R-naringenin was accumulated. Finally, a total of 17.4 g 2R-naringenin, 18.0 g kaempferol, and 26.1 g L-rhamnose were prepared from 100 g naringin. Thus, this study provides a novel strategy for the production of value-added compounds from naringin with an environmentally safe process., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.)
- Published
- 2024
- Full Text
- View/download PDF
3. Gut commensal metabolite rhamnose promotes macrophages phagocytosis by activating SLC12A4 and protects against sepsis in mice.
- Author
-
Li D, Wei R, Zhang X, Gong S, Wan M, Wang F, Li J, Chen M, Liu R, Wan Y, Hong Y, Zeng Z, Gu P, Wang Z, Selva Nandakumar K, Jiang Y, Zhou H, and Chen P
- Abstract
Sepsis progression is significantly associated with the disruption of gut eubiosis. However, the modulatory mechanisms of gut microbiota operating during sepsis are still unclear. Herein, we investigated how gut commensals impact sepsis development in a pre-clinical model. Cecal ligation and puncture (CLP) surgery was used to establish polymicrobial sepsis in mice. Mice depleted of gut microbiota by an antibiotic cocktail (ABX) exhibited a significantly higher level of mortality than controls. As determined by metabolomics analysis, ABX treatment has depleted many metabolites, and subsequent supplementation with l-rhamnose (rhamnose, Rha), a bacterial carbohydrate metabolite, exerted profound immunomodulatory properties with a significant enhancement in macrophage phagocytosis, which in turn improved organ damage and mortality. Mechanistically, rhamnose binds directly to and activates the solute carrier family 12 (potassium-chloride symporter), member 4 (SLC12A4) in macrophages and promotes phagocytosis by activating the small G-proteins, Ras-related C3 botulinum toxin substrate1 (Rac1) and cell division control protein 42 homolog (Cdc42). Interestingly, rhamnose has enhanced the phagocytosis capacity of macrophages from sepsis patients. In conclusion, by identifying SLC12A4 as the host interacting protein, we disclosed that the gut commensal metabolite rhamnose is a functional molecular that could promote the phagocytosis capacity of macrophages and protect the host against sepsis., (© 2024 The Authors.)
- Published
- 2024
- Full Text
- View/download PDF
4. Structure elucidation and anticancer activity of a heteropolysaccharide from white tea.
- Author
-
Wang P, Zhao B, Yin Z, Gao X, and Liu M
- Subjects
- Rhamnose, Glucuronic Acid, Tea, Polysaccharides chemistry, Galactose analysis
- Abstract
White tea, one of the six traditional teas in China, is made only through natural withering and low-temperature drying processes. It demonstrates diverse pharmacological and health-promoting effects, including antioxidant, antiviral, anticancer, and hypolipidemic activities. Despite the significance of polysaccharides in white tea leaves, their fine structure and physiological functions remain unexplored. In this study, the polysaccharide fragment WTP-80a with anticancer activity was isolated and purified from white tea through water extraction, alcohol precipitation, DEAE-52 ion exchange column chromatography, and sephacryl S-200 dextran gel column chromatography. WTP-80a exhibited a molecular weight of 1.14 × 10
5 Da and consisted of galactose (Gal), arabinose (Ara), rhamnose (Rha), and glucuronic acid (Glc-UA). The main chain skeleton of WTP-80a contained 3,6)-β-Galp-(1→, 3)-α-Galp-(1→, 5)-α-Araf-(1 → and 3)-α-Glcp-UA-(1→. Branch chains included α-Araf-(1 → and β-Rhap-(1 → connected to the C3 and C6 positions of →3,6)-β-Galp-(1→, respectively. In vitro anticancer experiments revealed that WTP-80a effectively hindered the proliferation, colony formation, migration, and invasion of B16F10 cells. Additionally, it induced apoptosis in B16F10 cells by blocking the G2/M phase, increasing active oxygen content, and reducing mitochondrial membrane potential. These findings provide a solid theoretical foundation for the application of white tea polysaccharides as anticancer products., Competing Interests: Declaration of competing interest The authors declare that they have no conflict of interest., (Copyright © 2023. Published by Elsevier Ltd.)- Published
- 2024
- Full Text
- View/download PDF
5. An interlaboratory study on the detection method for Escherichia albertii in food using real time PCR assay and selective agars.
- Author
-
Arai S, Hirose S, Yanagimoto K, Kojima Y, Yamaya S, Yamanaka T, Matsunaga N, Kobayashi A, Takahashi N, Konno T, Tokoi Y, Sakakida N, Konishi N, and Hara-Kudo Y
- Subjects
- Agar, Real-Time Polymerase Chain Reaction, RNA, Ribosomal, 16S, Rhamnose, Culture Media, Meat, Food Microbiology, Lactose, Escherichia coli, Xylose, Escherichia
- Abstract
Escherichia albertii is an emerging enteropathogen. Although E. albertii-specific detection and isolation methods have been developed, their efficiency on food samples have not yet been systematically studied. To establish a series of effective methods for detecting E. albertii in food, an interlaboratory study was conducted in 11 laboratories using enrichment with modified E. coli broth supplemented with cefixime and tellurite (CT-mEC), real-time PCR assay, and plating on four kinds of selective agars. This study focused on the detection efficiency of an E. albertii-specific real-time PCR assay (EA-rtPCR) and plating on deoxycholate hydrogen sulfide lactose agar (DHL), MacConkey agar (MAC), DHL supplemented with rhamnose and xylose (RX-DHL), and MAC supplemented with rhamnose and xylose (RX-MAC). Chicken and bean sprout samples were inoculated with E. albertii either at 17.7 CFU/25 g (low inoculation level) or 88.5 CFU/25 g (high inoculation level), and uninoculated samples were used as controls. The sensitivity of EA-rtPCR was 1.000 for chicken and bean sprout samples inoculated with E. albertii at low and high inoculation levels. The Ct values of bean sprout samples were higher than those of the chicken samples. Analysis of microbial distribution by 16S rRNA gene amplicon sequencing in enriched cultures of bean sprout samples showed that approximately >96 % of the population comprised unidentified genus of family Enterobacteriaceae and genus Acinetobacter in samples which E. albertii was not isolated. The sensitivity of the plating methods for chicken and bean sprout samples inoculated with a high inoculation level of E. albertii was 1.000 and 0.848-0.970, respectively. The sensitivity of the plating methods for chicken and bean sprout samples inoculated with a low inoculation level of E. albertii was 0.939-1.000 and 0.515-0.727, respectively. The E. albertii-positive rate in all colonies isolated in this study was 89-90 % in RX-DHL and RX-MAC, and 64 and 44 % in DHL and MAC, respectively. Therefore, the sensitivity of RX-supplemented agar was higher than that of the agars without these sugars. Using a combination of enrichment in CT-mEC and E. albertii isolation on selective agars supplemented with RX, E. albertii at an inoculation level of over 17.5 CFU/25 g of food was detected with a sensitivity of 1.000 and 0.667-0.727 in chicken and bean sprouts, respectively. Therefore, screening for E. albertii-specific genes using EA-rtPCR followed by isolation with RX-DHL or RX-MAC is an efficient method for E. albertii detection in food., Competing Interests: Declaration of competing interest The authors declare that they have no competing financial interests or personal relationships that could have influenced the work reported in this article., (Copyright © 2024 Elsevier B.V. All rights reserved.)
- Published
- 2024
- Full Text
- View/download PDF
6. Onosma glomeratum Y. L. Liu polysaccharide alleviates LPS-induced pulmonary inflammation via NF-κB signal pathway.
- Author
-
Yang Q, Shen X, Zhao J, Er-Bu A, Liang X, He C, Yin L, Xu F, Li H, Tang H, Fu Y, and Lv C
- Subjects
- Mice, Animals, Lipopolysaccharides, Rhamnose, Polysaccharides pharmacology, Polysaccharides therapeutic use, Polysaccharides analysis, Signal Transduction, NF-kappa B, Pneumonia chemically induced, Pneumonia drug therapy, Hexuronic Acids
- Abstract
As a traditional Chinese medicinal and edible homologous plant, Onosma glomeratum Y. L. Liu has been used for treating lung diseases in Tibet. In this study, a pectin polysaccharide, OGY-LLPA, with a molecular weight of 62,184 Da, was isolated and characterized by GC-MS and NMR analysis. It mainly consists of galacturonic acid (GalA), galactose (Gal), rhamnose (Rha), and arabinose (Ara), with a linear main chain of galacturonic acid (homogalacturonan, HG) inserted by part of rhamnose galacturonic acid (rhamnogalacturonan, RG), attaching with arabinogalactan (AG) branches at RG-I. Both in the LPS-induced A549 cell model and LPS-induced pneumonia mouse model, OGY-LLPA demonstrated strong anti-inflammatory effects, even comparable to DEX, indicating its potential as an anti-pneumonia candidate agent. Moreover, low-dose OGY-LLPA alleviated LPS-induced pulmonary inflammation by inhibiting the NF-κB signaling pathway. Overall, these findings could not only contribute to the utilization of Onosma glomeratum Y. L. Liu., but also provides a theoretical basis for the treatment of inflammation-related diseases., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier B.V. All rights reserved.)
- Published
- 2024
- Full Text
- View/download PDF
7. Multivalent Rhamnose-Modified EGFR-Targeting Nanobody Gains Enhanced Innate Fc Effector Immunity and Overcomes Cetuximab Resistance via Recruitment of Endogenous Antibodies.
- Author
-
Li Y, Lin H, Hong H, Li D, Gong L, Zhao J, Wang Z, and Wu Z
- Subjects
- Animals, Humans, Mice, Antibodies, Monoclonal, Humanized therapeutic use, Cell Line, Tumor, Cetuximab pharmacology, Cetuximab therapeutic use, Immunity, Innate, ErbB Receptors immunology, Rhamnose, Single-Domain Antibodies pharmacology, Drug Resistance, Neoplasm immunology
- Abstract
Cetuximab resistance is a significant challenge in cancer treatment, requiring the development of novel therapeutic strategies. In this study, a series of multivalent rhamnose (Rha)-modified nanobody conjugates are synthesized and their antitumor activities and their potential to overcome cetuximab resistance are investigated. Structure-activity relationship studies reveal that the multivalent conjugate D5, bearing sixteen Rha haptens, elicits the most potent innate fragment crystallizable (Fc) effector immunity in vitro and exhibits an excellent in vivo pharmacokinetics by recruiting endogenous antibodies. Notably, it is found that the optimal conjugate D5 represents a novel entity capable of reversing cetuximab-resistance induced by serine protease (PRSS). Moreover, in a xenograft mouse model, conjugate D5 exhibits significantly improved antitumor efficacy compared to unmodified nanobodies and cetuximab. The findings suggest that Rha-Nanobody (Nb) conjugates hold promise as a novel therapeutic strategy for the treatment of cetuximab-resistant tumors by enhancing the innate Fc effector immunity and enhancing the recruitment of endogenous antibodies to promote cancer cell clearance by innate immune cells., (© 2024 The Authors. Advanced Science published by Wiley‐VCH GmbH.)
- Published
- 2024
- Full Text
- View/download PDF
8. Isolation, Purification and Tyrosinase Inhibitory Activity of Anthocyanins and Their Novel Degradation Compounds from Solanum tuberosum L.
- Author
-
Ouyang J, Hu N, and Wang H
- Subjects
- Animals, Monophenol Monooxygenase, Melanins, Molecular Docking Simulation, Rhamnose, Zebrafish, Anthocyanins pharmacology, Solanum tuberosum
- Abstract
To explore the composition of anthocyanins and expand their biological activities, anthocyanins were systematically isolated and purified from tubers of Solanum tuberosum L., and their tyrosinase inhibitory activity was investigated. In this study, two new anthocyanin degradation compounds, norpetanin ( 9 ) and 4- O -( p -coumaryl) rhamnose ( 10 ), along with 17 known anthocyanins and their derivatives, were isolated and purified from an acid-ethanolic extract of fresh purple potato tubers. Their structures were elucidated via 1D and 2D NMR and HR-ESI-MS and compared with those reported in the literature. The extracts were evaluated for anthocyanins and their derivatives using a tyrosinase inhibitor screening kit and molecular docking technology, and the results showed that petanin, norpetanin, 4- O -( p -coumaryl) rhamnose, and lyciruthephenylpropanoid D/E possessed tyrosinase inhibitory activity, with 50% inhibiting concentration (IC
50 ) values of 122.37 ± 8.03, 115.53 ± 7.51, 335.03 ± 12.99, and 156.27 ± 11.22 μM (Mean ± SEM, n = 3), respectively. Furthermore, petanin was validated against melanogenesis in zebrafish; it was found that it could significantly inhibit melanin pigmentation ( p < 0.001), and the inhibition rate of melanin was 17% compared with the normal group. This finding may provide potential treatments for diseases with abnormal melanin production, and high-quality raw materials for whitening cosmetics.- Published
- 2024
- Full Text
- View/download PDF
9. X-ray structure and characterization of a probiotic Lactobacillus rhamnosus Probio-M9 L-rhamnose isomerase.
- Author
-
Yoshida H, Yamamoto N, Kurahara LH, Izumori K, and Yoshihara A
- Subjects
- Humans, X-Rays, Rhamnose, Monosaccharides, Lacticaseibacillus rhamnosus, Aldose-Ketose Isomerases
- Abstract
A recombinant L-rhamnose isomerase (L-RhI) from probiotic Lactobacillus rhamnosus Probio-M9 (L. rhamnosus Probio-M9) was expressed. L. rhamnosus Probio-M9 was isolated from human colostrum and identified as a probiotic lactic acid bacterium, which can grow using L-rhamnose. L-RhI is one of the enzymes involved in L-rhamnose metabolism and catalyzes the reversible isomerization between L-rhamnose and L-rhamnulose. Some L-RhIs were reported to catalyze isomerization not only between L-rhamnose and L-rhamnulose but also between D-allulose and D-allose, which are known as rare sugars. Those L-RhIs are attractive enzymes for rare sugar production and have the potential to be further improved by enzyme engineering; however, the known crystal structures of L-RhIs recognizing rare sugars are limited. In addition, the optimum pH levels of most reported L-RhIs are basic rather than neutral, and such a basic condition causes non-enzymatic aldose-ketose isomerization, resulting in unexpected by-products. Herein, we report the crystal structures of L. rhamnosus Probio-M9 L-RhI (LrL-RhI) in complexes with L-rhamnose, D-allulose, and D-allose, which show enzyme activity toward L-rhamnose, D-allulose, and D-allose in acidic conditions, though the activity toward D-allose was low. In the complex with L-rhamnose, L-rhamnopyranose was found in the catalytic site, showing favorable recognition for catalysis. In the complex with D-allulose, D-allulofuranose and ring-opened D-allulose were observed in the catalytic site. However, bound D-allose in the pyranose form was found in the catalytic site of the complex with D-allose, which was unfavorable for recognition, like an inhibition mode. The structure of the complex may explain the low activity toward D-allose. KEY POINTS: • Crystal structures of LrL-RhI in complexes with substrates were determined. • LrL-RhI exhibits enzyme activity toward L-rhamnose, D-allulose, and D-allose. • The LrL-RhI is active in acidic conditions., (© 2024. The Author(s).)
- Published
- 2024
- Full Text
- View/download PDF
10. Rhamnose-PEG-induced supramolecular helices: Addressing challenges of drug solubility and release efficiency in transdermal patch.
- Author
-
Song H, Liu C, Ruan J, Cai Y, Wang J, Wang X, and Fang L
- Subjects
- Pharmaceutical Preparations, Solubility, Administration, Cutaneous, Excipients chemistry, Adhesives chemistry, Drug Liberation, Rhamnose, Transdermal Patch
- Abstract
Transdermal drug delivery systems (TDDS) demand both high drug loading capacity and efficient delivery. In order to improve both simultaneously, this study aims to develop a novel rhamnose-induced pressure-sensitive adhesive (HPR) by dispersing the drug in the supramolecular helical structure. Ten model drugs, categorized as acidic and basic compounds, were chosen to understand the characteristics of the HPR and its inner mechanism. Notably, it enhanced drug loading by 1.41 to 5 times over commercially available pressure-sensitive adhesives Duro-Tak@ 87-4098 and Duro-Tak@ 87-2287, in addition to increasing drug release efficiency by a factor of about 5. Pharmacokinetic evaluation demonstrated that the HPR group had >4-fold (Tulobuterol TUL) and 3-fold (Diclofenac DIC) more area under the blood drug concentration curve (AUC) than the commercial TUL and DIC patches in the absence of added excipients and a significantly prolonged mean residence time (MRT) of >4-fold (TUL) and 3-fold (DIC), demonstrating the potential for highly efficacious and prolonged dosing. Furthermore, its safety and mechanical properties meet the requisite standards. Mechanistic inquiries unveiled that both acidic and basic drugs establish hydrogen bonds with HPR and become encapsulated within supramolecular helical structures. The supramolecular helical structures, significantly elevated both the enthalpy of the drug-HPR and entropy of the drugs release, thereby substantially enhancing drug delivery efficiency. In summary, HPR enabled a significant simultaneous enhancement of drug loading and drug delivery, which, together with its unique spatial structure, would contribute to the development of TDDS. In addition, the establishment of rhamnose-induced supramolecular helical structures would provide innovative pathways for different drug delivery systems., (Copyright © 2024 Elsevier B.V. All rights reserved.)
- Published
- 2024
- Full Text
- View/download PDF
11. Complete composition analysis of polysaccharides based on HPAEC-PAD coupled with quantitative analysis of multi-components by single marker.
- Author
-
Yan XH, Liu XQ, Liang J, Kuang HX, and Xia YG
- Subjects
- Monosaccharides analysis, Monosaccharides chemistry, Glucose, Rhamnose, Polysaccharides analysis, Polysaccharides chemistry
- Abstract
Introduction: Monosaccharide compositions analysis (MCA) is indispensable for structural characterisations and structure-activity relationships of plant polysaccharides., Objectives: To develop a concise and direct MCA method, we established a quantitative analysis of the multi-monosaccharaides by single marker (QAMS) by high-performance anion-exchange chromatography with pulsed-amperometric detection (HPAEC-PAD) method., Methodology: A stable and reproducible HPAEC-PAD method for simultaneous determination of aldoses, ketoses and uronic acids (i.e., l-arabinose, d-xylose, d-ribose, l-rhamnose, d-fucose, d-mannose, d-glucose, d-galactose, d-fructose, d-glucuronic acid and d-galacturonic acid) was established by systematic optimisation of stationary phases, column temperatures and elution programmes. On this basis, the QAMS method was proposed through comprehensive investigations of relative correction factor (RCF) variations under different influencing factors, for example, sample concentrations, flow rates, and column temperatures., Results: Using rhamnose as an internal reference standard, the contents of the other monosaccharide components in polysaccharides from Panax quinquefolium L. and Achyranthes bidentata Bl. samples were simultaneously determined by QAMS, and there was no significant difference between the results from the QAMS and external standard method (t test, P > 0.520). In addition, a MCA fingerprinting of 30 batches of P. quinquefolium polysaccharide was established by HPAEC-PAD, and six common peaks were assigned and determined., Conclusions: The established HPAEC-PAD-QAMS method was successfully applied to the MCA of polysaccharides from P. quinquefolium and A. bidentata after optimisation of hydrolysis conditions. HPAEC-PAD-QAMS was proposed and established for MCA of plant polysaccharides for the first time., (© 2023 John Wiley & Sons Ltd.)
- Published
- 2024
- Full Text
- View/download PDF
12. A Rhamnose-PEG-Modified Dendritic Polymer for Long-Term Efficient Transdermal Drug Delivery.
- Author
-
Song H, Cai Y, Nan L, Liu J, Wang J, Wang X, Liu C, Guo J, and Fang L
- Subjects
- Humans, Animals, Swine, Rhamnose, Tissue Adhesions, Administration, Cutaneous, Skin, Pharmaceutical Preparations, Adhesives chemistry, Drug Delivery Systems, Dendrimers
- Abstract
This study introduces a dendronized pressure-sensitive adhesive, TMPE@Rha, addressing Food and Drug Administration (FDA) concerns about traditional pressure-sensitive adhesives (PSAs) in transdermal drug delivery systems. The unique formulation, composed of rhamnose, trihydroxypropane, and poly(ethylene glycol), significantly enhances cohesion and tissue adhesion. Leveraging rhamnose improves intermolecular interactions and surface chain mobility, boosting tissue adhesion. Compared to acrylic pressure-sensitive adhesive 87-DT-4098, TMPE@Rha shows substantial advantages, with up to 5 to 6 times higher peel strength on porcine and wood substrates. Importantly, it maintains strong human skin adhesion beyond 7 days without the typical "dark ring" phenomenon. When loaded with diclofenac, the adhesive exhibits 3.12 times greater peeling strength than commercial alternatives, sustaining human adhesion for up to 6 days. Rigorous analyses confirm rhamnose's role in increasing interaction strength. In vitro studies and microscopy demonstrate the polymer's ability to enhance drug loading and distribution on the skin, improving permeability. Biocompatibility tests affirm TMPE@Rha as nonirritating. In summary, TMPE@Rha establishes a new standard for PSAs in transdermal drug delivery systems, offering exceptional adhesion, robustness, and biocompatibility. This pioneering work provides a blueprint for next-generation, highly adhesive, drug-loaded PSAs that meet and exceed FDA criteria.
- Published
- 2024
- Full Text
- View/download PDF
13. Rhamnose modified antibodies show improved immune killing towards EGFR-positive solid tumor cells.
- Author
-
Hong H, Zhao J, Zhou K, Li Y, Li D, and Wu Z
- Subjects
- Animals, Humans, Mice, Cetuximab pharmacology, Antibodies, Monoclonal pharmacology, ErbB Receptors, Cell Line, Tumor, Rhamnose pharmacology, Antineoplastic Agents pharmacology, Antineoplastic Agents therapeutic use
- Abstract
Therapeutic monoclonal antibodies (mAbs) against the epidermal growth factor receptor (EGFR) have shown clinical efficacy in colorectal cancer and other solid cancers. Enhancing the effector functions of these anti-EGFR mAbs is believed to be a valuable approach to achieve improved efficacy in clinical setting. Here, we report the development of an effector function-enhanced antibody by rhamnose (Rha) functionalization. Cetuximab, a human/mouse chimeric anti-EGFR mAb, was selected and site-specifically conjugated with Rha haptens. The obtained cetuximab-Rha conjugate was shown to be able to selectively redirect amounts of endogenous anti-Rha antibodies onto EGFR-positive solid tumor cells and thereby provide more Fc domains to achieve enhancement of effector functions including complement-dependent cytotoxicity (CDC) and antibody-dependent cell-mediated phagocytosis (ADCP). Particularly, CDC, one powerful cell killing mechanism which is inactive in cetuximab, was dramatically improved. This study demonstrates the potential of rhamnose-modified antibody for EGFR-positive solid tumor immunotherapy., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.)
- Published
- 2024
- Full Text
- View/download PDF
14. Electrodialysis treatment of rhamnolipids hydrolysate and its waste water for use as water-soluble fertilizer.
- Author
-
Shen C, Li Y, Lu G, and Meng Q
- Subjects
- Rhamnose, Glycolipids, Wastewater, Fertilizers
- Abstract
Rhamnolipids can serve as a precursor for rhamnose production, but using ion exchange resin in purifying rhamnolipids hydrolysate results in excessive high-salinity wastewater, making the process environmentally and economically unfeasible. This study introduced electrodialysis technology as an alternative for purifying rhamnolipids hydrolysate, significantly reducing wastewater to less than 5 % compared to the resin method. To achieve zero wastewater discharge, the electrodialysis-treated wastewater was repurposed into a water-soluble fertilizer containing 7.1 g/L of rhamnolipids, 11.4 g/L of fatty acid, 2.4 g/L of amino acid, and 8.2 g/L of potassium. Unlike traditional fertilizers, the nutritional components with rhamnolipids showed remarkable potential in enhancing tomato plant growth, flowering, and fruit quality. Taken together, the electrodialysis treatment of rhamnolipids hydrolysate largely reduced the water volume, the economic cost, and took a full use of the final wastewater as efficient water-soluble fertilizers, making it applicable for large-scale rhamnose production., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023. Published by Elsevier Ltd.)
- Published
- 2024
- Full Text
- View/download PDF
15. Preparation of isoquercitrin and rhamnose from readily accessible rutin by a highly specific recombinant α - L -rhamnosidase ( r -Rha1).
- Author
-
Chen Y, Wang L, Guo Y, Zhang M, Xie H, Xia G, Xu L, Yang H, and Shen Y
- Abstract
Isoquercitrin has superior in vivo bioactivities with respect to its primary glycoside rutin. Its conventional preparation was ineffective, with large chemical consumption and many by-products. Rhamnose, a high value-added monosaccharide, is usually separated from acid hydrolytes of rutin. This study aimed to establish a novel enzymatic hydrolysis-based approach for their preparation. α-L -rhamnosidase was expressed in Pichia pastoris GS115 and applied to enzymolysis of rutin. Then, one-factor-at-a-time optimisation of hydrolysis conditions was performed. Two compounds were produced in 0.02 M HAc-NaAc buffer (pH4.50) containing α- L -rhamnosidase/rutin (1:4, w/w) at 60 °C. Consequently, 20.0 g/L rutin was completely hydrolysed in 2 hrs, and isoquercitrin was obtained after purification by HPD-100 resin. Additionally, rhamnose was enriched by decolorisation and crystallisation. MD simulation analysis suggested that rutin was catalysed on the hydrophobic surface of r -Rha1 with van-der-Waals force being main driving force. This strategy is an efficient approach for preparation of isoquercitrin and rhamnose.
- Published
- 2024
- Full Text
- View/download PDF
16. Latrophilin, an adhesion GPCR with galactose-binding lectin domain involved in the innate immune response of Tribolium castaneum.
- Author
-
Wang S, Bi J, Li C, and Li B
- Subjects
- Animals, Mice, Galectins, Molecular Docking Simulation, Rhamnose, Immunity, Innate genetics, Tribolium genetics
- Abstract
Latrophilin is a member of adhesion GPCRs involved in various physiological pro1cesses. The extracellular fragment of Tribolium castaneum Latrophilin (TcLph) contains a galactose-binding lectin (GBL) domain. However, the biological function of GBL domain remains mysterious. Here, we initially studied the role of TcLph in recognizing pathogens through its GBL domain and then triggering immune defense in invertebrates. Results showed that GBL domain was highly conserved, and its predicted 3D structure was similar to rhamnose-binding lectin domain of mouse Latrophilin-1 with a unique α/β fold and two long loops. Molecular docking and ELISA results revealed the GBL domain can bind to D-galactose, L-rhamnose, lipopolysaccharide and peptidoglycan. The recombinant extracellular segment of TcLph and the recombinant GBL exhibited strong agglutinating and binding activities to all tested bacteria in a Ca
2+ -dependent manner. Moreover, TcLph was markedly induced after infection by Escherichia coli or Staphylococcus aureus, while its silencing exacerbated bacterial loads and larvae mortality. TcLph-deficient larvae significantly decreased the transcription levels of antimicrobial peptides and prophenoloxidase activating system-related genes, leading to a significant reduction in phenoloxidase activity. It indicated that TcLph functioned as a pattern recognition receptor in pathogen recognition and activated immune responses to eliminate invasive microbes, suggesting a potential target for insecticides., Competing Interests: Declaration of competing interest The authors declare that they have no conflicts of interest., (Copyright © 2023. Published by Elsevier B.V.)- Published
- 2023
- Full Text
- View/download PDF
17. New l-Rhamnose-Binding Lectin from the Bivalve Glycymeris yessoensis : Purification, Partial Structural Characterization and Antibacterial Activity.
- Author
-
Mizgina TO, Chikalovets IV, Bulanova TA, Molchanova VI, Filshtein AP, Ziganshin RH, Rogozhin EA, Shilova NV, and Chernikov OV
- Subjects
- Animals, Rhamnose, Escherichia coli, Tandem Mass Spectrometry, Anti-Bacterial Agents pharmacology, Lectins pharmacology, Bivalvia
- Abstract
In this study, a new l-rhamnose-binding lectin (GYL-R) from the hemolymph of bivalve Glycymeris yessoensis was purified using affinity and ion-exchange chromatography and functionally characterized. Lectin antimicrobial activity was examined in different ways. The lectin was inhibited by saccharides possessing the same configuration of hydroxyl groups at C-2 and C-4, such as l-rhamnose, d-galactose, lactose, l-arabinose and raffinose. Using the glycan microarray approach, natural carbohydrate ligands were established for GYL-R as l-Rha and glycans containing the α-Gal residue in the terminal position. The GYL-R molecular mass determined by MALDI-TOF mass spectrometry was 30,415 Da. The hemagglutination activity of the lectin was not affected by metal ions. The lectin was stable up to 75 °C and between pH 4.0 and 12.0. The amino acid sequence of the five GYL-R segments was obtained with nano-ESI MS/MS and contained both YGR and DPC-peptide motifs which are conserved in most of the l-rhamnose-binding lectin carbohydrate recognition domains. Circular dichroism confirmed that GYL is a α/β-protein with a predominance of the random coil. Furthermore, GYL-R was able to bind and suppress the growth of the Gram-negative bacteria E. coli by recognizing lipopolysaccharides. Together, these results suggest that GYL-R is a new member of the RBL family which participates in the self-defense mechanism against bacteria and pathogens with a distinct carbohydrate-binding specificity.
- Published
- 2023
- Full Text
- View/download PDF
18. A Natural Compound Containing a Disaccharide Structure of Glucose and Rhamnose Identified as Potential N-Glycanase 1 (NGLY1) Inhibitors.
- Author
-
Liu R, Gu J, Ye Y, Zhang Y, Zhang S, Lin Q, Yuan S, Chen Y, Lu X, Tong Y, Lv S, Chen L, and Sun G
- Subjects
- Peptide-N4-(N-acetyl-beta-glucosaminyl) Asparagine Amidase, Glycoproteins metabolism, Cytosol metabolism, Rhamnose, Glucose
- Abstract
N-glycanase 1 (NGLY1) is an essential enzyme involved in the deglycosylation of misfolded glycoproteins through the endoplasmic reticulum (ER)-associated degradation (ERAD) pathway, which could hydrolyze N-glycan from N-glycoprotein or N-glycopeptide in the cytosol. Recent studies indicated that NGLY1 inhibition is a potential novel drug target for antiviral therapy. In this study, structure-based virtual analysis was applied to screen candidate NGLY1 inhibitors from 2960 natural compounds. Three natural compounds, Poliumoside, Soyasaponin Bb, and Saikosaponin B2 showed significantly inhibitory activity of NGLY1, isolated from traditional heat-clearing and detoxifying Chinese herbs. Furthermore, the core structural motif of the three NGLY1 inhibitors was a disaccharide structure with glucose and rhamnose, which might exert its action by binding to important active sites of NGLY1, such as Lys238 and Trp244. In traditional Chinese medicine, many compounds containing this disaccharide structure probably targeted NGLY1. This study unveiled the leading compound of NGLY1 inhibitors with its core structure, which could guide future drug development.
- Published
- 2023
- Full Text
- View/download PDF
19. Tumor selective self-assembled nanomicelles of carbohydrate-epothilone B conjugate for targeted chemotherapy.
- Author
-
Xu Y, Qian L, Fang M, Liu Y, Xu ZJ, Ge X, Zhang Z, Liu ZP, and Lou H
- Subjects
- Humans, Carbohydrates therapeutic use, Disulfides, Cell Line, Tumor, Epothilones, Neoplasms drug therapy, Nanoparticles chemistry
- Abstract
Epothilone B (Epo B) is a potent antitumor natural product with sub-nanomolar anti-proliferation action against several human cancer cells. However, poor selectivity to tumor cells and unacceptable therapeutic windows of Epo B and its analogs are the major obstacles to their development into clinical drugs. Herein, we present self-assembled nanomicelles based on an amphiphilic carbohydrate-Epo B conjugate that is inactive until converted to active Epo B within the tumor. Four Epo B-Rhamnose conjugates linked via two linkers containing a disulfide bond that is sensitive to GSH were synthesized. Conjugate 34 can self-assemble into nanomicelles with a high concentration of Rha on the surface, allowing for better tumor targeting. After internalization by cancer cells, the disulfide bond can be cleaved in the presence of high levels of GSH to release active Epo B, thereby exhibiting significant anticancer efficiency and selectivity in vitro and in vivo., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023 Elsevier Masson SAS. All rights reserved.)
- Published
- 2023
- Full Text
- View/download PDF
20. Structural characteristics and functional properties of a fucose containing prebiotic exopolysaccharide from Bifidobacterium breve NCIM 5671.
- Author
-
Baruah R, Kumar PP, Gangani S, Prashanth KVH, and Halami PM
- Subjects
- Humans, Fucose, Galactose, Rhamnose, Glucose, Prebiotics, Bifidobacterium breve
- Abstract
Aim: To evaluate the structure and functions of capsular exopolysaccharide (CPS) from Bifidobacterium breve NCIM 5671., Methods and Results: A CPS produced by the probiotic bacteria B. breve NCIM 5671 was isolated and subjected to characterization through GC analysis, which indicated the presence of rhamnose, fucose, galactose, and glucose in a molar ratio of 3:1:5:3. The average molecular weight of the CPS was determined to be ∼8.5 × 105 Da. Further, NMR analysis revealed the probable CPS structure to be composed of major branched tetra- and penta-saccharide units alternately repeating and having both α- and β-configuration sugar residues. CPS displayed an encouraging prebiotic score for some of the studied probiotic bacteria. Compared to standard inulin, CPS showed better resistance to digestibility against human GI tract in vitro. DPPH, total antioxidant, and ferric reducing assays carried out for CPS displayed decent antioxidant activity too., Conclusion: This study indicates that the CPS from B. breve NCIM 5671 has the potential to be utilized as a prebiotic food supplement. It is a high-molecular-weight (∼8.5 × 105 Da) capsular heteropolysaccharide containing rhamnose, fucose, galactose, and glucose., (© The Author(s) 2023. Published by Oxford University Press on behalf of Applied Microbiology International.)
- Published
- 2023
- Full Text
- View/download PDF
21. Qualitative and quantitative analysis of triterpenoids in different tissues of Pulsatilla chinensis.
- Author
-
Zhang T, Zhang J, Chen F, Liu A, Jiang J, Yan Z, and Liu X
- Subjects
- Rhamnose, Mass Spectrometry methods, Chromatography, High Pressure Liquid methods, Pulsatilla chemistry, Triterpenes analysis, Saponins chemistry, Drugs, Chinese Herbal chemistry
- Abstract
Pulsatilla chinensis (P.chinensis) is a traditional Chinese medicine used for the treatment of intestinal amebiasis diseases, vaginal trichomoniasis and bacterial infections. Tritepenoid saponins were important components of P.chinensis. Therefore, we asssessmented expression profiling of triterpenoids in different fresh tissues of P.chinensis by ultra high performance liquid chromatography coupled to quadrupole-time-of-flight mass spectrometry (UHPLC-Q-TOF-MS) and ultra high performance liquid chromatography coupled to triple quadrupole mass spectrometry (UHPLC-QQQ-MS). Firstly, we identified 132 triterpenoids, including 119 triterpenoid saponins, 13 triterpenoid acids and forty seven of them were first determined in Pulsatilla genus, including new aglycones and new ways of rhamnose linking to the aglycone. Secondly, we established the analytical method to analysis triterpenoids content of P.chinensis and comprehensively verified the analytical method by linearity, precision, repeatability, stability and recovery. At last, we quantified 119 triterpenoids simultaneously based on UHPLC-QQQ-MS. The results show that the types and contents of triterpenoids had obvious tissue distribution. New components like rhamnose directly linked to the aglycone mainely distributed in aboveground tissues. Additionally, We identified 15 chemical ingredients as differential components between the aboveground and underground tissues of P.chinensis. This study provides an efficient analysis strategy for the qualitative and quantitative analysis of triterpenoids in P.chinensis even in other traditional Chinese medicines. At the same time, it provides important informations to explain the biosynthetic pathway of triterpenoid saponins in P.chinensis., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023 Elsevier B.V. All rights reserved.)
- Published
- 2023
- Full Text
- View/download PDF
22. Intestinal permeability in patients undergoing stem cell transplantation correlates with systemic acute phase responses and dysbiosis.
- Author
-
Wang YM, Abdullah S, Luebbering N, Langenberg L, Duell A, Lake K, Lane A, Hils B, Vazquez Silva O, Trapp M, Nalapareddy K, Koo J, Denson LA, Jodele S, Haslam DB, Faubion WA, Davies SM, and Khandelwal P
- Subjects
- Young Adult, Humans, Child, Rhamnose, Acute-Phase Reaction, Dysbiosis, Permeability, Lactulose metabolism, Hematopoietic Stem Cell Transplantation adverse effects
- Abstract
Intestinal permeability may correlate with adverse outcomes during hematopoietic stem cell transplantation (HSCT), but longitudinal quantification with traditional oral mannitol and lactulose is not feasible in HSCT recipients because of mucositis and diarrhea. A modified lactulose:rhamnose (LR) assay is validated in children with environmental enteritis. Our study objective was to quantify peri-HSCT intestinal permeability changes using the modified LR assay. The LR assay was administered before transplant, at day +7 and +30 to 80 pediatric and young adult patients who received allogeneic HSCT. Lactulose and rhamnose were detected using urine mass spectrometry and expressed as an L:R ratio. Metagenomic shotgun sequencing of stool for microbiome analyses and enzyme-linked immunosorbent assay analyses of plasma lipopolysaccharide binding protein (LBP), ST2, REG3α, claudin1, occludin, and intestinal alkaline phosphatase were performed at the same timepoints. L:R ratios were increased at day +7 but returned to baseline at day +30 in most patients (P = .014). Conditioning regimen intensity did not affect the trajectory of L:R (P = .39). Baseline L:R ratios did not vary with diagnosis. L:R correlated with LBP levels (r2 = 0.208; P = .0014). High L:R ratios were associated with lower microbiome diversity (P = .035), loss of anaerobic organisms (P = .020), and higher plasma LBP (P = .0014). No adverse gastrointestinal effects occurred because of LR. Intestinal permeability as measured through L:R ratios after allogeneic HSCT correlates with intestinal dysbiosis and elevated plasma LBP. The LR assay is well-tolerated and may identify transplant recipients who are more likely to experience adverse outcomes., (© 2023 by The American Society of Hematology. Licensed under Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0), permitting only noncommercial, nonderivative use with attribution. All other rights reserved.)
- Published
- 2023
- Full Text
- View/download PDF
23. The Separation, Purification, Structure Identification, and Antioxidant Activity of Elaeagnus umbellata Polysaccharides.
- Author
-
Zhang J, Xu X, Liu X, Chen M, Bai B, Yang Y, Bo T, and Fan S
- Subjects
- Galactose, Rhamnose, Spectroscopy, Fourier Transform Infrared, Polysaccharides pharmacology, Antioxidants pharmacology, Elaeagnaceae
- Abstract
In order to investigate the antioxidant activity of Elaeagnus umbellata polysaccharides, the physicochemical characteristics of purified Elaeagnus umbellata polysaccharides (EUP, consisting of two fractions, EUP1 and EUP2) were investigated using UV spectrophotometry, high-performance liquid chromatography (HPLC), high-performance gel permeation chromatography (HPGPC), and Fourier transform infrared spectroscopy (FT-IR). This revealed that EUP1 and EUP2 were acidic polysaccharides with an average molecular weight (MW) of 63 and 38 kDa, respectively. EUP1 mainly consisted of L-rhamnose and D-galactose in a molar ratio of 2.05:1, and EUP2 consisted of D-mannose, L-rhamnose, D-galactose, and D-arabinose in a molar ratio of 2.06:1:2.78:1. Furthermore, EUP exhibited considerable antioxidant potential for scavenging hydroxyl, superoxide anion, DPPH, and ABTS radicals. Therefore, EUP can be developed as a potential antioxidant for the functional food or pharmaceutical field.
- Published
- 2023
- Full Text
- View/download PDF
24. Bifunctionalized Betulinic Acid Conjugates with C-3-Monodesmoside and C-28-Triphenylphosphonium Moieties with Increased Cancer Cell Targetability.
- Author
-
Tsepaeva OV, Salikhova TI, Ishkaeva RA, Kundina AV, Abdullin TI, Laikov AV, Tikhomirova MV, Idrisova LR, Nemtarev AV, and Mironov VF
- Subjects
- Male, Humans, Betulinic Acid, Mannose, Chromatography, Liquid, Rhamnose, Tandem Mass Spectrometry, Glycosides, Triterpenes pharmacology, Triterpenes chemistry, Neoplasms
- Abstract
A convenient synthesis is presented for a new class of bioactive bifunctionalized conjugates of lupane-type triterpenoids with triphenylphosphonium (TPP) and glycopyranosyl targeting moieties. The main synthesis steps include glycosylation of haloalkyl esters of the triterpene acid at the C-3 position by the imidate derivatives of glycopyranose followed by the product modification at the C-28 position with triphenylphosphine. The conjugates of betulinic acid (BetA) with TPP and d-glucose, l-rhamnose, or d-mannose moieties were thus synthesized as potential next-generation BetA-derived anticancer compounds. LC-MS/MS analysis in glucose-free physiological solution indicated that the glycosides showed better accumulation in PC-3 prostate cancer cells than both BetA and TPP-BetA conjugate, while the transporting effect of monosaccharide residues increased as follows: d-mannose < l-rhamnose ≈ d-glucose. At saturated concentrations, the glycosides caused a disturbing effect on mitochondria with a more drastic drop in transmembrane potential but weaker overproduction of mitochondrial reactive oxygen species (ROS) compared to TPP-BetA conjugate. Cytotoxicity of the glycosides in culture medium was comparable with or higher than that of the nonglycosylated conjugate, depending on the cancer cell line, whereas the compounds were less active toward primary fibroblasts. Glycosylation tended to increase pro-apoptotic and decrease pro-autophagic activities of the BetA derivatives. Cytotoxicity of the synthesized glycosides was considered in comparison with the summarized data on the natural and modified BetA glycosides. The results obtained are important for the development of bifunctionalized conjugates of triterpenoids with an increased cancer cell targetability.
- Published
- 2023
- Full Text
- View/download PDF
25. Straightforward synthesis of the hexasaccharide repeating unit of the O-specific polysaccharide of Salmonella arizonae O62.
- Author
-
Rana A, Shit P, and Misra AK
- Subjects
- Glycosylation, Monosaccharides, Rhamnose, Oligosaccharides chemistry, Salmonella arizonae, O Antigens chemistry
- Abstract
A straightforward synthesis of the hexasaccharide repeating unit of the O-specific polysaccharide of Salmonella arizonae O62 was achieved in very good yield applying sequential glycosylation strategy. Successful regioselective glycosylation of the di-hydroxylated L-rhamnose moiety allowed achieving the desired compound in minimum number of synthetic steps. TEMPO catalyzed and [bis(acetoxy)iodo]benzene (BAIB) mediated late stage regioselective oxidation of a primary hydroxyl group into carboxylic acid was achieved in the hexasaccharide derivative. The glycosylation steps were high yielding with high stereochemical outcome. The desired hexasaccharide was obtained in 7% over all yield in fourteen steps starting from suitably functionalized monosaccharide intermediates., (© 2023. The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.)
- Published
- 2023
- Full Text
- View/download PDF
26. Structure Characterization and Immunomodulatory Activity of Misgurnus anguillicaudatus Carbohydrates.
- Author
-
Yun L, Han C, He X, Li Q, Fersht V, and Zhang M
- Subjects
- Animals, Mice, Interleukin-6, Rhamnose, Tumor Necrosis Factor-alpha, Monoamine Oxidase, Fucose, Cypriniformes
- Abstract
Misgurnus anguillicaudatus, also known as oriental weather loach, is widely consumed and favored in East Asia due to its superior nutritional values and excellent flavor. In this study, a crude Misgurnus anguillicaudatus carbohydrates (MAC) was isolated from Misgurnus anguillicaudatus . Subsequently, two parts, which were named MAO and MAP, respectively, were separated from MAC, and their primary structures and immunomodulatory activity were investigated. The results showed that MAO had a molecular weight of 2854 Da, and principally consisted of arabinose (77.11%) and rhamnose (21.97%), together with minor levels of fucose (0.92%); MAP, with a molecular weight of 3873 Da, was mainly composed of fucose (87.55%) and a small amount of rhamnose (8.86%) and galactose (3.59%). The in vitro assay showed that MAC could significantly enhance the proliferation of macrophages without cytotoxicity and increase the production of immune substances (TNF-α, IL-6). Together with Western blot results, we speculated that MAC could stimulate RAW264.7 murine macrophage cells to secrete TNF-α and IL-6 through up-regulating TLR4-MAPK-p38 signaling pathways. The results indicated that MAC could be a potential immune agent and might provide meaningful information for further chain conformation and immune mechanism research.
- Published
- 2023
- Full Text
- View/download PDF
27. Identification, Chemical Synthesis, and Sweetness Evaluation of Rhamnose or Xylose Containing Steviol Glycosides of Stevia ( Stevia rebaudiana ) Leaves.
- Author
-
Watanabe T, Fujikawa K, Urai S, Iwaki K, Hirai T, Miyagawa K, Uratani H, Yamagaki T, Nagao K, Yokoo Y, and Shimamoto K
- Subjects
- Rhamnose, Xylose, Glycosides chemistry, Sweetening Agents chemistry, Plant Leaves chemistry, Stevia chemistry, Diterpenes, Kaurane chemistry
- Abstract
Steviol glycosides obtained from Stevia rebaudiana leaves are increasingly used in the food industry as natural low-calorie sweeteners. Among them, the sweetness of major glycosides composed of glucose residues (e.g., stevioside and rebaudioside A) has been widely studied. However, the properties of minor natural products containing rhamnose or xylose residues are poorly investigated. In this study, five unreported steviol glycosides containing rhamnose or xylose were extracted from our developing stevia leaves, and their sweetness was evaluated. The highly glycosylated steviol glycosides were identified, and their structures were examined by fragmentation analysis using mass spectrometry. Chemical synthesis of these glycosides confirmed their structures and allowed sensory evaluation of minor steviol glycosides. Our study revealed that a xylose-containing glycoside, rebaudioside FX1, exhibits a well-balanced sweetness, and thus, it is a promising candidate for natural sweeteners used in the food industry.
- Published
- 2023
- Full Text
- View/download PDF
28. Pectins from the sea grass Enhalus acoroides (L.f.) Royle: Structure, biological activity and ability to form nanoparticles.
- Author
-
Thinh PD, Rasin AB, Silchenko AS, Trung VT, Kusaykin MI, Hang CTT, Menchinskaya ES, Pislyagin EA, and Ermakova SP
- Subjects
- Pectins chemistry, Poaceae, Rhamnose, Chitosan pharmacology, Chitosan chemistry, Nanoparticles chemistry
- Abstract
Two pectins from the seagrass Enhalus acoroides (L.f.) Royle were isolated for the first time. Their structures and biological activities were investigated. NMR spectroscopy showed one of them to consist exclusively from the repeating →4-α-d-GalpUA→ residue (Ea1), while the other had a much more complex structure that also included 1→3-linked α-d-GalpUA residues, 1→4-linked β-apiose residues and small amounts of galactose and rhamnose (Ea2). The pectin Ea1 showed noticeable dose-dependent immunostimulatory activity, the Ea2 fraction was less effective. Both pectins were used to create pectin-chitosan nanoparticles for the first time, and the influence of pectin/chitosan mass ratio on their size and zeta potential was investigated. Ea1 particles were slightly smaller than Ea2 particles (77 ± 16 nm vs 101 ± 12 nm) and less negatively charged (-23 mV vs -39 mV). Assessment of their thermodynamic parameters showed that only the second pectin could form nanoparticles at room temperature., Competing Interests: Declaration of competing interest The authors declare no conflict of interest., (Copyright © 2023 Elsevier B.V. All rights reserved.)
- Published
- 2023
- Full Text
- View/download PDF
29. The Systemic Availability of Indispensable Amino Acids from Orally Ingested Algal and Legume Protein in Young Children at Risk of Environmental Enteric Dysfunction.
- Author
-
Shivakumar N, Kashyap S, Jahoor F, Devi S, Preston T, Thomas T, and Kurpad AV
- Subjects
- Humans, Child, Child, Preschool, Amino Acids metabolism, Lactulose, Rhamnose, Vegetables metabolism, Phenylalanine, Digestion, Fabaceae metabolism, Vigna
- Abstract
Background: The digestion and absorption of ingested protein may be reduced in children with environmental enteric dysfunction (EED), reducing systemic amino acid availability for protein synthesis with resultant growth faltering. This has not been directly measured in children with EED and associated growth faltering., Objectives: To evaluate the systemic availability of algal (spirulina) and legume (mung bean) indispensable amino acids (IAAs) in children with EED., Methods: Indian children (18-24 mo) from urban slums were assigned to EED (n = 24) or no-EED (control, n = 17) groups based on the lactulose rhamnose test, where the lactulose rhamnose ratio cutoff for diagnosing EED (≥0.068) was the mean + 2SD of its distribution in healthy, age-, and sex-matched children of high socioeconomic status. Fecal biomarkers of EED were also measured. Systemic IAA availability was calculated from the plasma: meal IAA enrichment ratio for each protein. True ileal mung bean IAA digestibility was measured by the dual isotope tracer method using spirulina protein as reference. Co-administration of free
13 C6 -phenylalanine allowed for estimating true ileal phenylalanine digestibility of both proteins, and a phenylalanine absorption index., Results: There was no significant difference (independent t-test) in the systemic IAA availability from spirulina or mung bean protein between EED and no-EED groups. There was no between-group difference in true ileal phenylalanine digestibility and its absorption index, or in mung bean IAA digestibility., Conclusions: The systemic IAA availability of algal and legume protein, or the latter's IAA/phenylalanine digestibility, is not significantly reduced in children with EED and does not correlate with linear growth. This study was registered in Clinical Trials Registry of India (CTRI) with registration number: CTRI/2017/02/007921., (Copyright © 2023 American Society for Nutrition. Published by Elsevier Inc. All rights reserved.)- Published
- 2023
- Full Text
- View/download PDF
30. L-Rhamnose and Phenolic Esters-Based Monocatenar and Bolaform Amphiphiles: Eco-Compatible Synthesis and Determination of Their Antioxidant, Eliciting and Cytotoxic Properties.
- Author
-
Kordkatooli E, Bacha K, Villaume S, Dorey S, Monboisse JC, Brassart-Pasco S, Mbakidi JP, and Bouquillon S
- Subjects
- Esters pharmacology, Phenols pharmacology, Glycosylation, Coumaric Acids, Antioxidants pharmacology, Antioxidants metabolism, Rhamnose
- Abstract
Symmetrical and dissymmetrical bolaforms were prepared with good to high yields from unsaturated L-rhamnosides and phenolic esters (ferulic, phloretic, coumaric, sinapic and caffeic) using two eco-compatible synthetic strategies involving glycosylation, enzymatic synthesis and cross-metathesis under microwave activation. The plant-eliciting activity of these new compounds was investigated in Arabidopsis model plants. We found that the monocatenar rhamnosides and bolaforms activate the plant immune system with a response depending on the carbon chain length and the nature of the hydrophilic heads. Their respective antioxidant activities were also evaluated, as well as their cytotoxic properties on dermal cells for cosmetic uses. We showed that phenolic ester-based compounds present good antioxidant activities and that their cytotoxicity is low. These properties are also dependent on the carbon chains used.
- Published
- 2023
- Full Text
- View/download PDF
31. Practical Antibody Recruiting by Metabolic Labeling with Caged Glycans.
- Author
-
Milawati H, Manabe Y, Matsumoto T, Tsutsui M, Ueda Y, Miura A, Kabayama K, and Fukase K
- Subjects
- Cell Membrane metabolism, Rhamnose, Polysaccharides metabolism, Antibodies
- Abstract
We propose a de novo glycan display approach that combines metabolic labeling and a glycan-caging strategy as a facile editing method for cell-surface glycans. This method enables the introduction of antigen glycans onto cancer cells to induce immune responses through antibody recruiting. The caging strategy prevents the capture of α-rhamnose (an antigen glycan) by endogenous antibodies during the introduction of the glycan to the targeted cell surface, and subsequent uncaging successfully induces immune responses. Therefore, this study proposes a practical method for editing the cell-surface glycocalyx under promiscuous conditions, such as those in vivo, which paves the way for the development of glycan function analysis and regulation., (© 2023 Wiley-VCH GmbH.)
- Published
- 2023
- Full Text
- View/download PDF
32. Cell-free expression and characterization of multivalent rhamnose-binding lectins using bio-layer interferometry.
- Author
-
Warfel KF, Laigre E, Sobol SE, Gillon E, Varrot A, Renaudet O, Dejeu J, Jewett MC, and Imberty A
- Subjects
- Carbohydrates chemistry, Recombinant Proteins genetics, Interferometry methods, Lectins chemistry, Rhamnose
- Abstract
Lectins are important biological tools for binding glycans, but recombinant protein expression poses challenges for some lectin classes, limiting the pace of discovery and characterization. To discover and engineer lectins with new functions, workflows amenable to rapid expression and subsequent characterization are needed. Here, we present bacterial cell-free expression as a means for efficient, small-scale expression of multivalent, disulfide bond-rich, rhamnose-binding lectins. Furthermore, we demonstrate that the cell-free expressed lectins can be directly coupled with bio-layer interferometry analysis, either in solution or immobilized on the sensor, to measure interaction with carbohydrate ligands without purification. This workflow enables the determination of lectin substrate specificity and estimation of binding affinity. Overall, we believe that this method will enable high-throughput expression, screening, and characterization of new and engineered multivalent lectins for applications in synthetic glycobiology., (© The Author(s) 2023. Published by Oxford University Press. All rights reserved. For permissions, please e-mail: journals.permissions@oup.com.)
- Published
- 2023
- Full Text
- View/download PDF
33. Novel polysaccharide and polysaccharide-peptide conjugate from Rosa rugosa Thunb. pseudofruit - Structural characterisation and nutraceutical potential.
- Author
-
Olech M, Cybulska J, Nowacka-Jechalke N, Szpakowska N, Masłyk M, Kubiński K, Martyna A, Zdunek A, and Kaczyński Z
- Subjects
- Rhamnose, Mannose, Arabinose, Spectroscopy, Fourier Transform Infrared, Proteomics, Monosaccharides chemistry, Glucose, Polysaccharides chemistry, Dietary Supplements, Uronic Acids chemistry, Peptides pharmacology, Galactose, Rosa chemistry
- Abstract
A novel bioactive polysaccharopeptide (C1) and polysaccharide (C2) with an average molecular weight of 180 kDa and 70 kDa were isolated from R. rugosa pseudofruit. The composition of the macromolecules was established using
1 H NMR, FT-IR, GC-MS, SDS-PAGE coupled with enzymatic cleavage, and proteomic analyses (LC-MS). C1 was found to contain 60.56 ± 1.82 % of sugars and 21.17 ± 0.47 % of uronic acids. Its main neutral monosaccharides were arabinose, rhamnose, galactose, glucose, fucose, and mannose. C1 was found to be a polysaccharopeptide containing pectinesterase-like protein. C2 was composed of 32.85 ± 0.97 % of sugars and 48.77 ± 1.15 % of uronic acids. Its main neutral monosaccharides were galactose, glucose, rhamnose, arabinose, and mannose. A promising nutraceutical value of the polysaccharides was revealed. Assays showed strong α-glucosidase inhibitory activity of both macromolecules and considerable antiradical potential and moderate lipoxygenase inhibitory activity of the crude polysaccharide. Moreover, antiproliferative activity of C2 was observed., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2022 Elsevier Ltd. All rights reserved.)- Published
- 2023
- Full Text
- View/download PDF
34. Glycan Stability and Flexibility: Thermodynamic and Kinetic Characterization of Nonconventional Hydrogen Bonding in Lewis Antigens.
- Author
-
Kwon J, Ruda A, Azurmendi HF, Zarb J, Battistel MD, Liao L, Asnani A, Auzanneau FI, Widmalm G, and Freedberg DI
- Subjects
- Hydrogen Bonding, Thermodynamics, Polysaccharides, Hydrogen, Lewis Blood Group Antigens, Rhamnose
- Abstract
We provide evidence for CH-based nonconventional hydrogen bonds (H-bonds) for 10 Lewis antigens and two of their rhamnose analogues. We also characterize the thermodynamics and kinetics of the H-bonds in these molecules and present a plausible explanation for the presence of nonconventional H-bonds in Lewis antigens. Using an alternative method to simultaneously fit a series of temperature-dependent fast exchange nuclear magnetic resonance (NMR) spectra, we determined that the H-bonded conformation is favored by ∼1 kcal/mol over the non-H-bonded conformation. Additionally, a comparison of temperature-dependent
13 C linewidths in various Lewis antigens and the two rhamnose analogues reveals H-bonds between the carbonyl oxygen of the N -acetyl group of N -acetylglucosamine and the OH2 group of galactose/fucose. The data presented herein provide insight into the contribution of nonconventional H-bonding to molecular structure and could therefore be used for the rational design of therapeutics.- Published
- 2023
- Full Text
- View/download PDF
35. Synthesis and Evaluation of Fluorine-18-Labeled L-Rhamnose Derivatives.
- Author
-
Zhang X, Basuli F, Shi ZD, Shah S, Shi J, Mitchell A, Lai J, Wang Z, Hammoud DA, and Swenson RE
- Subjects
- Mice, Animals, Tissue Distribution, Cell Line, Tumor, Positron-Emission Tomography methods, Radiopharmaceuticals, Rhamnose, Fluorine Radioisotopes
- Abstract
The use of radiolabeled glucose for PET imaging resulted in the most commonly used tracer in the clinic, 2-deoxy-2-[
18 F]fluoroglucose (FDG). More recently, other radiolabeled sugars have been reported for various applications, including imaging tumors and infections. Therefore, in this study, we developed a series of fluorine-18-labeled L-rhamnose derivatives as potential PET tracers of various fungal and bacterial strains. Acetyl-protected triflate precursors of rhamnose were prepared and radiolabeled with fluorine-18 followed by hydrolysis to produce L-deoxy [18 F]fluororhamnose. The overall radiochemical yield was 7-27% in a 90 min synthesis time with a radiochemical purity of 95%. In vivo biodistribution of the ligands using PET imaging showed that 2-deoxy-2-[18 F]fluoro-L-rhamnose is stable for at least up to 60 min in mice and eliminated via renal clearance. The tracer also exhibited minimal tissue or skeletal uptake in healthy mice resulting in a low background signal., Competing Interests: The authors declare no conflict of interest.- Published
- 2023
- Full Text
- View/download PDF
36. Polysaccharide-Based Composite Scaffolds for Osteochondral and Enthesis Regeneration.
- Author
-
Baawad A, Jacho D, Hamil T, Yildirim-Ayan E, and Kim DS
- Subjects
- Humans, Tendons physiology, Cartilage, Osteogenesis, Tissue Scaffolds chemistry, Tissue Engineering methods, Bone and Bones
- Abstract
The rotator cuff and Achilles tendons along with the anterior cruciate ligament (ACL) are frequently injured with limited healing capacity. At the soft-hard tissue interface, enthesis is prone to get damaged and its regeneration in osteochondral defects is essential for complete healing. The current clinical techniques used in suturing procedures to reattach tendons to bones need much improvement for the generation of the native interface tissue, that is, enthesis, for patients to regain their full functions. Recently, inspired by the composite native tissue, much effort has been made to fabricate composite scaffolds for enthesis tissue regeneration. This review first focuses on the studies that used composite scaffolds for the regeneration of enthesis. Then, the use of polysaccharides for osteochondral tissue engineering is reviewed and their potential for enthesis regeneration is presented based on their supporting effects on osteogenesis and chondrogenesis. Gellan gum (GG) is selected and reviewed as a promising polysaccharide due to its unique osteogenic and chondrogenic activities that help avoid the inherent weakness of dissimilar materials in composite scaffolds. In addition, original preliminary results showed that GG supports collagen type I production and upregulation of osteogenic marker genes. Impact Statement Enthesis regeneration is essential for complete and functional healing of tendon and ligament tissues. Current suturing techniques to reattach the tendon/ligament to bones have high failure rates. This review highlights the studies on biomimetic scaffolds aimed to regenerate enthesis. In addition, the potential of using polysaccharides to regenerate enthesis is discussed based on their ability to regenerate osteochondral tissues. Gellan gum is presented as a promising biopolymer that can be modified to simultaneously support bone and cartilage regeneration by providing structural continuity for the scaffold.
- Published
- 2023
- Full Text
- View/download PDF
37. Physicochemical, structural and emulsifying properties of RG-I enriched pectin extracted from unfermented or fermented cherry pomace.
- Author
-
Du Y, Zhang S, Sun-Waterhouse D, Zhou T, Xu F, Waterhouse GIN, and Wu P
- Subjects
- Pectins, Glucose, Galactose, Rhamnose
- Abstract
This study explores cherry waste valorization through sustainable green approaches. Two low-methoxy rhamnogalacturonan I (RG-I) enriched pectins were produced via mild aqueous extraction from cherry pomaces before and after yeast fermentation (RCUP and RCFP: RG-I, 52.02% and 48.81%; methylation degree, 44.71% and 37.55%). Both pectins contained galacturonic acid, arabinose, galactose, rhamnose and glucose. Compared with RCFP, RCUP was a more linear pectin with higher Mw, wider Mw distribution, longer homogalacturonans (HGs) and shorter side chains. Fermentation increased protein, mannose, glucose and galactose contents, and decreased pectin yield, total phenolic/anthocyanin and rhamnose contents, melting temperature and enthalpy, degradation enthalpy, viscosity, storage and loss moduli. Fermentation induced a much greater loss of HG (from 43.55% to 14.65%) than RG-I (from 52.02% to 48.81%). RCUP and RCFP possessed significant antioxidant activities and exhibited satisfactory emulsifying effects at 2%. RCUP was a more effective emulsifier. RCFP had a higher hydroxyl radical scavenging capacity., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2022 Elsevier Ltd. All rights reserved.)
- Published
- 2023
- Full Text
- View/download PDF
38. A novel l-rhamnose-binding lectin participates in defending against bacterial infection in zebrafish.
- Author
-
Wang J, Guo XL, Chen HY, Xiao LX, Yang GW, and Yang HT
- Subjects
- Animals, Zebrafish, Rhamnose, Lipopolysaccharides, Amino Acid Sequence, Sequence Alignment, Gram-Negative Bacteria, Bacteria genetics, Immunity, Innate genetics, Lectins, C-Type genetics, Phylogeny, Lectins genetics, Bacterial Infections
- Abstract
l-rhamnose-binding lectin (RBL), which is a class of animal lectins independent of Ca
2+ , can specifically bind l-rhamnose or d-galactose. Although several lectins in zebrafish have been reported, their functional mechanisms have not been fully uncovered. In this study, we discovered a novel l-rhamnose binding lectin (DrRBL) and studied its innate immune function. The DrRBL protein contains only one carbohydrate-recognition domain (CRD), which includes two strictly conserved motifs, "YGR" and "DPC". DrRBL was detected in all tested tissues and was present at high levels in the spleen, hepatopancreas and skin. After Aeromonas hydrophila challenge, the DrRBL mRNA level was significantly upregulated. Additionally, DrRBL was secreted into the extracellular matrix. Recombinant DrRBL (rDrRBL) could significantly inhibit the growth of gram-positive/negative bacteria, bind to several bacteria and cause obvious agglutination. The rDrRBL protein could combine with polysaccharides, such as PGN and LPS, rather than LTA. A more detailed study showed that rDrRBL could combine with monosaccharides, such as mannose, rhamnose and glucose, which are important components of PGN and LPS. However, rDrRBL could not bind to ribitol, which is an important component of LTA. The DrRBL deletion mutants, DrRBLΔ144-150 and DrRBLΔ198-200 , were also constructed. DrRBLΔ144-150 ("ANYGRTD" deficient) showed weak bacterial inhibiting ability. However, DrRBLΔ198-200 ("DPC" deficient) showed weak agglutination ability. These results suggest that the "DPC" domain is important for agglutination. The conserved domain "ANYGRTD" is essential for inhibiting bacterial growth., (Copyright © 2023 Elsevier Ltd. All rights reserved.)- Published
- 2023
- Full Text
- View/download PDF
39. Intestinal permeability in patients with IgA nephropathy and other glomerular diseases: an observational study.
- Author
-
Seikrit C, Schimpf JI, Wied S, Stamellou E, Izcue A, Pabst O, Rauen T, Lenaerts K, and Floege J
- Subjects
- Humans, Prospective Studies, Cross-Sectional Studies, Pilot Projects, Rhamnose, Permeability, Erythritol, Glomerulonephritis, IGA
- Abstract
Background: A dysregulated 'gut-kidney axis' may contribute to immunoglobulin A nephropathy (IgAN). We studied whether IgAN patients have disturbed intestinal permeability., Methods: In a prospective, cross sectional, pilot study we assessed intestinal permeability in 35 IgAN patients, 18 patients with non-IgAN glomerulonephritides (GNs) and 19 healthy controls. After an overnight fast, trial participants ingested a multi-sugar solution and samples were obtained from 0 to 2, 2 to 5- and 5 to 24-h urine portions. Urinary sugar concentrations were quantified using isocratic ion-exchange high performance liquid chromatography. Indices of small intestinal permeability (0-2-h lactulose/L-rhamnose (L/R) ratio), distal small intestinal and proximal colonic permeability (2-5-h sucralose/erythritol (S/E) ratio) and colonic permeability (5-24-h sucralose/erythritol (S/E) ratio) were evaluated. Associations between groups and indices of intestinal permeability were investigated by a linear mixed model., Results: Small intestinal permeability (0-2 h L/R-ratio) was significantly increased in patients with glomerular diseases versus healthy controls. More precisely, increased small intestinal permeability was exclusively noted in non-IgAN GN patients, whereas IgAN patients exhibited a trend towards elevated small intestinal permeability. In total, 54% of patients with IgAN and 67% of non-IgAN GN patients had increased small intestinal permeability. Neither distal small intestinal and proximal colonic permeability nor colonic gut permeability indices (i.e., 2-5 h and 5-24 h S/E ratios) were significantly different between controls and any of the GN patient groups., Conclusion: The present single center pilot study suggests that disturbed intestinal permeability is common in patients with glomerular diseases and is not specific for IgAN., Trial Registration Number: German Clinical Trials Register DRKS00021533, Date: 24.04.2020., (© 2022. The Author(s).)
- Published
- 2023
- Full Text
- View/download PDF
40. Variability of biochemical compounds in surface sediments along the eastern margin of the Arabian Sea.
- Author
-
Khodse VB, Amberkar U, Khandeparker R, and Ramaiah N
- Subjects
- Arabinose, Ribose, Fucose, Rhamnose, Environmental Monitoring, Hexoses, Glucose, Uronic Acids, Geologic Sediments analysis, Galactose, Mannose
- Abstract
Different fractions of organic matter in surface sediments from three transects along the eastern margin of the Arabian Sea (AS) were quantified to determine the sources of organic matter, and also to study its impact on microbial community structure. From the extensive analyses of different biochemical parameters, it was evident that the distribution of total carbohydrate (TCHO), total neutral carbohydrate (TNCHO), proteins, lipids, and uronic acids (URA) concentrations and yield (% TCHO-C/TOC) are affected by organic matter (OM) sources and microbial degradation of sedimentary OM. Monosaccharide compositions from surface sediment was quantified to assess the sources and diagenetic fate of carbohydrates, suggesting that the deoxysugars (rhamnose plus fucose) had significant inverse relationship (r = 0.928, n = 13, p < 0.001) with hexoses (mannose plus galactose plus glucose) and positive relationship (r = 0.828, n = 13, p < 0.001) with pentoses (ribose plus arabinose plus xylose). This shows that marine microorganisms are the source of carbohydrates and there is no influence of terrestrial OM along the eastern margin of AS. During the degradation of algal material, the hexoses seem to be preferentially used by heterotrophic organisms in this region. Arabinose plus galactose (glucose free wt %) values between 28 and 64 wt% indicate that OM was derived from phytoplankton, zooplankton, and non-woody tissues. In the principal component analysis, rhamnose, fucose, and ribose form one cluster of positive loadings while glucose, galactose, and mannose form another cluster of negative loadings which suggest that during OM sinking process, hexoses were removed resulting in increase in bacterial biomass and microbial sugars. Results indicate sediment OM to be derived from marine microbial source along the eastern margin of AS., (© 2023. The Author(s), under exclusive licence to Springer Nature Switzerland AG.)
- Published
- 2023
- Full Text
- View/download PDF
41. Hesperidin, Hesperetin, Rutinose, and Rhamnose Act as Skin Anti-Aging Agents.
- Author
-
Novotná R, Škařupová D, Hanyk J, Ulrichová J, Křen V, Bojarová P, Brodsky K, Vostálová J, and Franková J
- Subjects
- Humans, Collagenases metabolism, Hyaluronoglucosaminidase, Pancreatic Elastase, Hesperidin pharmacology, Rhamnose pharmacology, Skin Aging drug effects
- Abstract
Aging is a complex physiological process that can be accelerated by chemical (high blood glucose levels) or physical (solar exposure) factors. It is accompanied by the accumulation of altered molecules in the human body. The accumulation of oxidatively modified and glycated proteins is associated with inflammation and the progression of chronic diseases (aging). The use of antiglycating agents is one of the recent approaches in the preventive strategy of aging and natural compounds seem to be promising candidates. Our study focused on the anti-aging effect of the flavonoid hesperetin, its glycoside hesperidin and its carbohydrate moieties rutinose and rhamnose on young and physiologically aged normal human dermal fibroblasts (NHDFs). The anti-aging activity of the test compounds was evaluated by measuring matrix metalloproteinases (MMPs) and inflammatory interleukins by ELISA. The modulation of elastase, hyaluronidase, and collagenase activity by the tested substances was evaluated spectrophotometrically by tube tests. Rutinose and rhamnose inhibited the activity of pure elastase, hyaluronidase, and collagenase. Hesperidin and hesperetin inhibited elastase and hyaluronidase activity. In skin aging models, MMP-1 and MMP-2 levels were reduced after application of all tested substances. Collagen I production was increased after the application of rhamnose and rutinose.
- Published
- 2023
- Full Text
- View/download PDF
42. Dendrobium officinale Xianhu 2 polysaccharide helps forming a healthy gut microbiota and improving host immune system: An in vitro and in vivo study.
- Author
-
Zhou W, Tao W, Wang M, Liu W, Xing J, and Yang Y
- Subjects
- Mice, Animals, Mannose, Tumor Necrosis Factor-alpha, Galactose, Rhamnose, Butyric Acid, Polysaccharides, Dietary Carbohydrates, Glucose, Immune System, Dendrobium, Gastrointestinal Microbiome
- Abstract
Dendrobium officinale is widely consumed owing to its numerous beneficial effects. We aimed to characterize polysaccharides of Dendrobium officinale (DOP) from the stems of Dendrobium officinale Xianhu 2 and clarify whether it benefit the intestinal microbiota and the immune system. The DOP weighed 291 kDa and comprised mannose, glucose, galactose, and rhamnose at 59.31:33.31:1.00:0.51 M ratio. In in vitro/vivo studies, DOP significantly increased benign intestinal microbe proportion (Lactobacillus, etc.), but reduced harmful bacteria (Escherichia_Shigella) (P < 0.05), and significantly increased butyric acid production (P < 0.05). Concentrations of 2 g/L DOP for in vitro fermentation and 100 mg/kg body weight for the mouse model were effective. In mice, DOP significantly reduced CRP, CD3, CD4, and TNF-α levels and increased C4 levels (P < 0.05). DOP might influence the immune system indirectly through regulation of the gut microbiota. Its possible regulation mechanism was that DOP reduced CD4+ Th cells proliferation so that reduced the secretion of TNF-α., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2022 Elsevier Ltd. All rights reserved.)
- Published
- 2023
- Full Text
- View/download PDF
43. Rhamnopyranoside-Based Fatty Acid Esters as Antimicrobials: Synthesis, Spectral Characterization, PASS, Antimicrobial, and Molecular Docking Studies.
- Author
-
Sanaullah AFM, Devi P, Hossain T, Sultan SB, Badhon MMU, Hossain ME, Uddin J, Patwary MAM, Kazi M, and Matin MM
- Subjects
- Molecular Docking Simulation, Fluconazole, Rhamnose, Spectroscopy, Fourier Transform Infrared, Stearates, Molecular Structure, Antifungal Agents pharmacology, Antifungal Agents chemistry, Anti-Infective Agents pharmacology, Anti-Infective Agents chemistry
- Abstract
The most widely used and accessible monosaccharides have a number of stereogenic centers that have been hydroxylated and are challenging to chemically separate. As a result, the task of regioselective derivatization of such structures is particularly difficult. Considering this fact and to get novel rhamnopyranoside-based esters, DMAP-catalyzed di- O -stearoylation of methyl α-l-rhamnopyranoside ( 3 ) produced a mixture of 2,3-di- O - ( 4 ) and 3,4-di- O -stearates ( 5 ) (ratio 2:3) indicating the reactivity of the hydroxylated stereogenic centers of rhamnopyranoside as 3-OH > 4-OH > 2-OH. To get novel biologically active rhamnose esters, di- O -stearates 4 and 5 were converted into six 4- O - and 2- O -esters 6 - 11 , which were fully characterized by FT-IR,
1 H, and13 C NMR spectral techniques. In vitro antimicrobial assays revealed that fully esterified rhamnopyranosides 6 - 11 with maximum lipophilic character showed better antifungal susceptibility than antibacterial activity. These experimental findings are similar to the results found from PASS analysis data. Furthermore, the pentanoyl derivative of 2,3-di- O -stearate (compound 6 ) showed better antifungal functionality against F. equiseti and A. flavus , which were found to be better than standard antibiotics. To validate the better antifungal results, molecular docking of the rhamnose esters 4 - 11 was performed with lanosterol 14α-demethylase (PDB ID: 3LD6), including the standard antifungal antibiotics ketoconazole and fluconazole. In this instance, the binding affinities of 10 (-7.6 kcal/mol), 9 (-7.5 kcal/mol), and 7 (-6.9 kcal/mol) were better and comparable to fluconazole (-7.3 kcal/mol), indicating the likelihood of their use as non-azole type antifungal drugs in the future.- Published
- 2023
- Full Text
- View/download PDF
44. Bipartite rgp Locus Diversity in Streptococcus thermophilus Corresponds to Backbone and Side Chain Differences of Its Rhamnose-Containing Cell Wall Polysaccharide.
- Author
-
Lavelle K, Sadovskaya I, Vinogradov E, Kelleher P, Lugli GA, Ventura M, van Sinderen D, and Mahony J
- Subjects
- Cell Wall, Polysaccharides, Yogurt, Streptococcus thermophilus genetics, Rhamnose
- Abstract
The rhamnose-glucose polysaccharide (Rgp) of Streptococcus thermophilus represents a major cell wall component, and the gene cluster responsible for its biosynthesis (termed rgp ) has recently been identified. Significant genetic diversity among these loci has previously been reported, with five distinct rgp genotypes identified (designated rgp1 through - 5 ). In the present study, two additional genotypes were identified (designated rgp6 and rgp7 ) through comparative analysis of the rgp loci of 78 Streptococcus thermophilus genomes. The rgp locus of a given S. thermophilus strain encoded the biosynthetic machinery for a rhamnan-rich backbone and a variable side chain component, the latter being associated with the highly specific interactions with many bacteriophages that infect this species. The chemical structure of the Rgp from three S. thermophilus strains, representing the rgp2 , -3 , and -4 genotypes, was elucidated, and based on bioinformatic and biochemical analyses we propose a model for Rgp biosynthesis in dairy streptococci. Furthermore, we exploited the genetic diversity within the S. thermophilus bipartite rgp locus to develop a two-step multiplex PCR system to classify strains based on gene content associated with the biosynthesis of the variable side chain structure as well as the rhamnan backbone. IMPORTANCE Streptococcus thermophilus is present and applied in industrial and artisanal dairy fermentations for the production of various cheeses and yogurt. During these fermentations, S. thermophilus is vulnerable to phage predation, and recent studies have identified the rhamnose-glucose polymer (Rgp) as the definitive receptor for at least one problematic phage species. Detailed analysis of S. thermophilus rgp loci has revealed an unprecedented level of genetic diversity, particularly within the glycosyltransferase-encoding gene content of a given locus. Our study shows that this genetic diversity reflects the biochemical structure(s) of S. thermophilus Rgp. As such, we harnessed the genetic diversity of S. thermophilus rgp loci to develop a two-step multiplex PCR method for the classification of strain collections and, ultimately, the formation of phage-robust rational starter sets.
- Published
- 2022
- Full Text
- View/download PDF
45. The variation on structure and immunomodulatory activity of polysaccharide during the longan pulp fermentation.
- Author
-
Hu TG, Zhu WL, Yu YS, Zou B, Xu YJ, Xiao GS, and Wu JJ
- Subjects
- Fermentation, Rhamnose, Acetic Acid, Phosphatidylinositol 3-Kinases, Polysaccharides pharmacology, Polysaccharides chemistry, Glucose, Mannose, Arabinose
- Abstract
In the current study, the effects of fermentation manners on the structure and immunomodulatory activity of polysaccharide in longan wine or vinegar were investigated. Compared to longan polysaccharide (CP1), polysaccharide in longan wine (CP2) or vinegar (CP3 and CP4) had smaller molecular weights, and was consisted of more mannose, arabinose, rhamnose, galactose and less glucose. After purification, the major fraction (P1-P4) was obtained from CP1-CP4, respectively. The structures and immunoregulatory activities of P1-P4 were characterized. Fermentation and purification were favorable to increase the immunoregulatory activities of P2-P4, which were contributed to their different structural features. The structure-activity relationship analysis indicated that molecular weight, mannose, rhamnose, glucuronic acid, glucose and arabinose were significantly associated with the cytokines secretion. Compared with other polysaccharides, P3 displayed better immunomodulatory activity due to its lower molecular weight, lower contents of rhamnose and glucose, and higher levels of mannose and arabinose by activating MAPK and PI3K/Akt signaling pathways., Competing Interests: Declaration of competing interest There are no conflicts to declare., (Copyright © 2022. Published by Elsevier B.V.)
- Published
- 2022
- Full Text
- View/download PDF
46. A water-soluble polysaccharide from Eucommia folium: the structural characterization and anti-tumor activity in vivo.
- Author
-
Yan ZQ, Ding SY, Chen P, Liu HP, Chang ML, and Shi SY
- Subjects
- Mice, Animals, Galactose, Rhamnose, Molecular Weight, Water, Polysaccharides chemistry
- Abstract
In this study, a water-soluble polysaccharide from Eucommia folium was extracted by hot water and purified using Sephadex G-200 gel columns. The results showed that the purified fraction (EFP) has a molecular weight of 9.98 × 10
5 Da and consisted of rhamnose, arabinose, galactose, glucose, mannose, xylose, galacturonic acid, and glucuronic acid (molar ratio: 0.226: 1.739: 2.183: 1: 0.155: 0.321: 0.358: 0.047). The combination of infrared spectroscopy and NMR analysis proved that EFP is an acidic polysaccharide whose main chain consists of α-L-Araf-(1 → , → 3,5)-α-Araf-(1 → , → 3)-β-Galp-(1 → , → 3,6)-β-Glcp-(1 → , → 2)-α-D-Manp-(1 → , → 4)-α-GalpA-(1 → , → 2,4)-α-Rhap-(1 → . In addition, the in vivo antitumoral activity of EFP was studied using a H22 tumor-bearing mice model. EFP effectively inhibited tumor growth in mice following intragastric administration. By Combining with the results of the apoptosis assay and JC-1 staining analysis, we confirmed that EFP induces apoptosis through the mitochondrial pathway. Furthermore, cell cycle analysis demonstrated that EFP blocks the cell cycle at S phase., (© 2022. The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.)- Published
- 2022
- Full Text
- View/download PDF
47. The effect of rugby training on indirect markers of gut permeability and gut damage in academy level rugby players.
- Author
-
Chantler S, Griffiths A, Phibbs P, Roe G, Ramírez-López C, Davison G, Jones B, and Deighton K
- Subjects
- Humans, Male, Young Adult, Fatty Acid-Binding Proteins, Lactulose, Permeability, Physical Fitness physiology, Rhamnose, Rugby, Intestines, Football physiology
- Abstract
Purpose: To assess indirect markers of intestinal endothelial cell damage and permeability in academy rugby players in response to rugby training at the beginning and end of preseason., Methods: Blood and urinary measures (intestinal fatty acid binding protein and lactulose:rhamnose) as measures of gastrointestinal cell damage and permeability were taken at rest and after a standardised collision-based rugby training session in 19 elite male academy rugby players (age: 20 ± 1 years, backs: 89.3 ± 8.4 kg; forwards: 111.8 ± 7.6 kg) at the start of preseason. A subsample (n = 5) repeated the protocol after six weeks of preseason training. Gastrointestinal symptoms (GIS; range of thirteen standard symptoms), aerobic capacity (30-15 intermittent fitness test), and strength (1 repetition maximum) were also measured., Results: Following the rugby training session at the start of preseason, there was an increase (median; interquartile range) in intestinal fatty acid binding protein (2140; 1260-2730 to 3245; 1985-5143 pg/ml, p = 0.003) and lactulose:rhamnose (0.31; 0.26-0.34 to 0.97; 0.82-1.07, p < 0.001). After six weeks of preseason training players physical qualities improved, and the same trends in blood and urinary measures were observed within the subsample. Overall, the frequency and severity of GIS were low and not correlated to markers of endothelial damage., Conclusions: Rugby training resulted in increased intestinal endothelial cell damage and permeability compared to rest. A similar magnitude of effect was observed after six weeks of pre-season training. This was not related to the experience of GIS., (© 2022. The Author(s).)
- Published
- 2022
- Full Text
- View/download PDF
48. Macroalgal biomass as a potential resource for lactic acid fermentation.
- Author
-
Nagarajan D, Chen CY, Ariyadasa TU, Lee DJ, and Chang JS
- Subjects
- Biomass, Carbon metabolism, Sugars metabolism, Fermentation, Lactic Acid metabolism, Seaweed metabolism
- Abstract
Lactic acid is an essential platform chemical with various applications in the chemicals, food, pharmaceutical, and cosmetic industries. Currently, the demand for lactic acid is driven by the role of lactic acid as the starting material for the production of bioplastic polylactide. Microbial fermentation for lactic acid production is favored due to the production of enantiomerically pure lactic acid required for polylactide synthesis, as opposed to the racemic mixture obtained via chemical synthesis. The utilization of first-generation feedstock for commercial lactic acid production is challenged by feedstock costs and sustainability issues. Macroalgae are photosynthetic benthic aquatic plants that contribute tremendously towards carbon capture with subsequent carbon-rich biomass production. Macroalgae are commercially cultivated to extract hydrocolloids, and recent studies have focused on applying biomass as a fermentation feedstock. This review provides comprehensive information on the design and development of sustainable and cost-effective, algae-based lactic acid production. The central carbon regulation in lactic acid bacteria and the metabolism of seaweed-derived sugars are described. An exhaustive compilation of lactic acid fermentation of macroalgae hydrolysates revealed that lactic acid bacteria can effectively ferment the mixture of sugars present in the hydrolysate with comparable yields. The environmental impacts and economic prospects of macroalgal lactic acid are analyzed. Valorization of the vast amounts of spent macroalgal biomass residue post hydrocolloid extraction in a biorefinery is a viable strategy for cost-effective lactic acid production., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2022 Elsevier Ltd. All rights reserved.)
- Published
- 2022
- Full Text
- View/download PDF
49. Isolation, characterisation and complement fixation activity of acidic polysaccharides from Argemone mexicana used as antimalarials in Mali.
- Author
-
Dénou A, Togola A, Inngjerdingen KT, Moussavi N, Rise F, Zou YF, Dafam DG, Nep EI, Ahmed A, Alemika TE, Diallo D, Sanogo R, and Paulsen BS
- Subjects
- Arabinose, Complement System Proteins, Galactose, Humans, Mali, Monosaccharides, Polymers, Polysaccharides isolation & purification, Polysaccharides pharmacology, Rhamnose, Antimalarials isolation & purification, Antimalarials pharmacology, Argemone chemistry
- Abstract
Context: Global studies on Argemone mexicana L. (Papaveraceae) traditionally used against malaria in Mali are limited to its low-mass compounds activities, and little information on its bioactive polysaccharides is available., Objective: This study determines the structure and the immunomodulatory activity of polysaccharides from aerial parts of A. mexicana ., Materials and Methods: Acidic polysaccharides from this plant material named HMAmA1 and HMAmA2 were isolated from water extracts. Their monosaccharide composition was determined by gas chromatography. Glycosidic linkages were determined using GC-MS. NMR was also applied. The polymers were tested for effects on the human complement system in vitro at different doses., Results: The monosaccharide composition showed that the two polysaccharides contained in different amounts the following monomers: arabinose, rhamnose, galactose, and galacturonic acid. Overall structural analysis showed the presence of a low ratio of 1,2-linked rhamnose compared to 1,4-linked galacturonic acid with arabinogalactans substituted on position 4 of rhamnose. NMR data showed the presence of galacturonans alternated by rhamnogalacturonans bearing arabinose and galactose units. α-Linkages were found for l-arabinose, l-rhamnose and d-galacturonic acid, while β-linkages were found for d-galactose. The two polysaccharides exhibited strong complement fixation activities, with HMAmA1 being the highest potent fraction. ICH
50 value of HMAmA1 was 5 µg/mL, compared to the control BPII being 15.9 µg/mL., Discussion and Conclusions: Polysaccharides form A. mexicana presented a complement fixation effect. The complement system is an important part of the immune defense, and compounds acting on the cascade are of interest. Therefore, these polymers may be useful as immunodulatory agents.- Published
- 2022
- Full Text
- View/download PDF
50. Extracellular polymeric substance profiling and biophysical analysis reveal influence factors of spontaneous flocculation in rich lipid alga Heveochlorella sp. Yu.
- Author
-
Cui N, Feng Y, He X, Gu H, and Zhao P
- Subjects
- Biofuels, Biomass, Extracellular Polymeric Substance Matrix, Flocculation, Fructose, Galactose, Glucose, Lipids, Mannose, Polysaccharides, Rhamnose, Chlorophyta, Microalgae
- Abstract
Microalgae harvest and lipid accumulation were important factors influencing commercialized development of microalgae biodiesel. Spontaneous flocculation was an ideal method in microalgae harvest, but few rich lipid microalgae could be harvested by spontaneous flocculation. Rich lipid alga Heveochlorella sp. Yu has a characteristic of spontaneous flocculation to be harvested. Heveochlorella sp. Yu has high lipid productivity (105.24 mg L
-1 d-1 ) and fine spontaneous flocculation efficiency (82.93 %, 2 h) on early stationary phase (day 9). The polysaccharides consisting of glucose, mannose, galactose, rhamnose and fructose (8.67:4.90:3.27:2.16:1) in loose-bound extracellular polymeric substance (LB-EPS) might make great contribution in microalgae flocculation. Meanwhile, the zeta potential close to zero was also beneficial to microalgae flocculation. Besides, the adhesion free energy related with cells adhesion was detected by thermomechanical analysis. Afterward, Extended Derjaguin-Landau-Verwey-Overbeek (XDLVO) theory was utilized to quantitatively evaluate short-range interactions involved in the spontaneous aggregation among cells. Collectively, biophysical analyses indicated that content and composition of EPS, Zeta potential, thermodynamic parameter and total interaction based on XDLVO theory were closely connected with spontaneous flocculation in microalga Yu. Our study provided a harvest-simplified process of rich microalgae, which proposes a new idea for commercial development of microalgae biodiesel., Competing Interests: Declaration of competing interest The authors declared that they have no conflicts of interest to this work. We declare that we do not have any commercial or associative interest that represents a conflict of interest in connection with the work submitted., (Copyright © 2022 Elsevier B.V. All rights reserved.)- Published
- 2022
- Full Text
- View/download PDF
Catalog
Discovery Service for Jio Institute Digital Library
For full access to our library's resources, please sign in.