Oligosaccharide Fragments Research Articles

Degradation of low-molecular-weight fucoidans by human intestinal microbiota and their regulation effect on intestinal microbiota and metabolites during in vitro fermentation

Fucoidan, a sulfated polysaccharide from brown algae, has been shown to improve gut microbiota balance and function. However, the relationship between molecular weight of fucoidan and colonic fermentation characteristics is still unclear. Here, the interaction between different-molecular-weight fucoidans and intestinal microbiota was analyzed via an in vitro fecal fermentation model. Results showed that fucoidan and its 2 low-molecular-weight derivatives (Dfuc1 and Dfuc2) could be utilized by intestinal microbiota after 48 h of fermentation, and among them, Dfuc2 exhibited the highest utilization efficiency of 30.1%, followed by Dfuc1 (24.5%) and fucoidan (14.4%). Notably, the components glucose, mannose and galactose, but not fucose, in different-molecular-weight fucoidans could be utilized. Moreover, intestinal microbiota could degrade Dfuc1 and Dfuc2 to produce oligosaccharide fragments, such as fucose-hexose disaccharide. In addition, fucoidan, Dfuc1 and Dfuc2 displayed different prebiotic effects on the intestinal microbiota community. Native fucoidan preferred to promote Bacteroides and Lactococcus, and low-molecular-weight fucoidans tended to promote Parabacteroides and Lactobacillus. Furthermore, metabolites analysis showed that fucoidan, Dfuc1 and Dfuc2 had similar promoting effects on acetic acid and propionic acid, and had no effect on butyric acid. But they could regulate carbohydrate metabolic pathways and amino acid pathways to varying degrees and with decreasing molecular weight, more differential metabolites were found. Thus, Dfuc2 with a lower molecular weight has more potential to become a potential prebiotics to improve intestinal health.

Divergent Synthesis and Antigenicity Evaluation of Core Oligosaccharides of the Lipopolysaccharides from Acinetobacter baumannii SMAL and ATCC 19606.

Acinetobacter baumannii poses a serious threat to human health. Pathogenic bacterial lipopolysaccharides (LPSs) are potent immunogens for the development of antibacterial vaccines. To investigate the antigenic properties of A. baumannii LPS, five well-defined core oligosaccharide fragments from the LPS of A. baumannii SMAL and ATCC 19606 were synthesized. A divergent synthesis strategy based on orthogonally protected α-(2 → 5)-linked Kdo dimer 6 was developed. Selective exposure of different positions in this key precursor and then elongation of sugar chains via stereocontrolled formation of both 1,2-trans and 1,2-cis-2-aminoglycosidic linkages permitted the efficient synthesis of the targets. The synthetic route also highlights a 4-O and then 7-O glycosylation sequence for assembly of the novel 4,7-branched Kdo framework. Antigenicity assay using the glycan microarray technique disclosed that tetrasaccharide 3 featuring both 4,7-branch and α-(2 → 5)-Kdo-Kdo structural elements was a potential antigenic determinant.

Structural characterization and immune activity evaluation of a polysaccharide from Lyophyllum Decastes

An innovative acidic hydrolysate fingerprinting workflow was proposed for the characterization of Lyophyllum Decastes polysaccharide (LDP) by ultra performance liquid chromatography-mass spectrometry (UPLC-MS). The crude polysaccharides were firstly separated and purified by using DE-52 column and the BRT GPC purification system, respectively. The molecular weight and monosaccharide content of homogeneous polysaccharides were ascertained by utilizing HPGPC and ion chromatography separately. Secondly, the linkage of LDP was identified by methylation analysis and 1D/2D NMR spectra. The UPLC-MS/MS was used to scan and identify the acidic hydrolysate products of LDP using the PGC column. The oligosaccharides were collected by chromatography and identified by mass spectrometry. Thirdly, the expression of IL-1β, IL-6, iNOS, TNF-α and IFNAR-I was measured in order to assess the immunological activity of LDP. Besides, the targeted receptors identification of polysaccharides was performed by screening the expression of TLRs family protein. The results showed that oligosaccharide fragments with different molecular weights can be obtained by partial hydrolysis, which further verified that the structures of LDP polysaccharides was a 1–6-linked β-glucan. Moreover, the LDP polysaccharide can up-regulate the content of IL-1β, IL-6, iNOS, TNF-α and IFNAR-I and plays an important immunoregulation role through TLRs family.

Synthesis of oligosaccharides from terminal B. pertussis LPS pentasaccharide and definition of the minimal epitope recognized by anti-pertussis antibodies.

Pertussis vaccines have been very effective in controlling whooping-cough epidemics but are ineffective in controlling circulation in older children and adults, thus facilitating the onset of future outbreaks. Antibodies against the lipopolysaccharide could reduce the carriage of the bacteria, its circulation, and transmission. The oligosaccharide fragments from the lipopolysaccharide may become a potential complement to existing vaccines in the form of protein glycoconjugates. An important step in the development of this type of vaccine is defining the minimal oligosaccharide epitope recognized by B. pertussis anti-lipopolysaccharide antibodies. This paper describes the complete synthesis of oligosaccharides containing two to five monosaccharide units corresponding to the pentasaccharide at the nonreducing end of the lipooligosaccharide and their recognition by mice and rabbit antibodies elicited against whole-cell B. pertussis. For the first time, we report that the terminal disaccharide, α-D-GlcNAcp-(1 → 4)-(2,3-di-NAc)-D-ManAp acid is the minimal structure recognized by antibodies induced by B. pertussis.

Chemical Synthesis of Truncated Capsular Oligosaccharide of Serotypes 6C and 6D of Streptococcus pneumoniae with Their Immunological Studies.

Serotypes 6C and 6D of Streptococcus pneumoniae are two major variants that cause invasive pneumococcal disease (IPD) in serogroup 6 alongside serotypes 6A and 6B. Since the introduction of the pneumococcal conjugate vaccines PCV7 and PCV13, the number of cases of IPD caused by pneumococcus in children and the elderly population has greatly decreased. However, with the widespread use of vaccines, a replacement effect has recently been observed among different serotypes and lowered the effectiveness of the vaccines. To investigate protection against the original serotypes and to explore protection against variants and replacement serotypes, we created a library of oligosaccharide fragments derived from the repeating units of the capsular polysaccharides of serotypes 6A, 6B, 6C, and 6D through chemical synthesis. The library includes nine pseudosaccharides with or without exposed terminal phosphate groups and four pseudotetrasaccharides bridged by phosphate groups. Six carbohydrate antigens related to 6C and 6D were prepared as glycoprotein vaccines for immunogenicity studies. Two 6A and two 6B glycoconjugate vaccines from previous studies were included in immunogenicity studies. We found that the conjugates containing four phosphate-bridged pseudotetrasaccharides were able to induce good immune antibodies and cross-immunogenicity by showing superior activity and broad cross-protective activity in OPKA bactericidal experiments.

Unusual triflic acid-promoted oligomerization of arabinofuranosides during glycosylation

We discovered an unusual triflic acid-promoted oligomerization of arabinofuranosides during glycosylation of the primary hydroxy group of α-(1 → 5)-linked tetraarabinofuranoside bearing 4-(2-chloroethoxy)phenyl aglycone with α-(1 → 5), β-(1 → 2)-linked tetraarabinofuranoside containing N-phenyltrifluoroacetimidoyl leaving group, which led to octa-, dodeca- and hexadecaarabinofuranosides. The possible mechanism of triflic acid-promoted oligomerization was proposed. The choice of promoter was found to be a critical factor for the discovered oligomerization of arabinofuranosides. The obtained octa-, dodeca- and hexadecaarabinofuranosides may serve as useful blocks in the synthesis of oligosaccharide fragments of polysaccharides of Mycobacterium tuberculosis.

Study of antibody repertoire to oligosaccharide fragments of polyglucosamines and galactosaminoglycans in sera from healthy human donors

Study of antibody repertoire to oligosaccharide fragments of polyglucosamines and galactosaminoglycans in sera from healthy human donors

Sea Cucumber Polysaccharide from Stichopus japonicu and Its Photocatalytic Degradation Product Alleviate Acute Alcoholic Liver Injury in Mice.

To prevent alcoholic liver disease, the addition of bioactive substances to the alcoholic drink Baijiu has been considered a feasible option. In the present study, the hepatoprotective effects of a sea cucumber sulfated polysaccharide (SCSP) isolated from Stichopus japonicu were investigated. Moreover, in order to enhance its solubility in an alcohol solution, it was depolymerized using a photocatalytic reaction, and the photocatalytic degradation products (dSCSPs) with an average molecular weight of less than 2 kDa were studied and compared with SCSP. They were characterized by a series of chemical and spectroscopy methods and the oligosaccharide fragments in the dSCSP were further identified by HPLC-MSn analysis. Then, the in vivo experiment showed that the addition of SCSP or dSCSP to Baijiu could alleviate alcoholic liver injury in mice. Further analysis also revealed their protective effect in reducing oxidative stress damage and their regulation of the metabolism of phosphatidylcholine (PC) and phosphatidylethanolamine (PE) in the liver. Of note, dSCSP was more effective at reducing the level of malondialdehyde in the liver. These findings indicate that the addition of sea cucumber polysaccharide or its low-molecular-weight derivative in Baijiu has the potential to alleviate alcoholic liver injury.

Towards Biomimetic Recognition of Glycans by Synthetic Receptors.

Carbohydrates are abundant in Nature, where they are mostly assembled within glycans as free polysaccharides or conjugated to a variety of biological molecules such as proteins and lipids. Glycans exert several functions, including protein folding, stability, solubility, resistance to proteolysis, intracellular traffic, antigenicity, and recognition by carbohydrate-binding proteins. Interestingly, misregulation of their biosynthesis that leads to changes in glycan structures is frequently recognized as a mark of a disease state. Because of glycan ubiquity, carbohydrate binding agents (CBAs) targeting glycans can lead to a deeper understanding of their function and to the development of new diagnostic and prognostic strategies. Synthetic receptors selectively recognizing specific carbohydrates of biological interest have been developed over the past three decades. In addition to the success obtained in the effective recognition of monosaccharides, synthetic receptors recognizing more complex guests have also been developed, including di- and oligosaccharide fragments of glycans, shedding light on the structural and functional requirements necessary for an effective receptor. In this review, the most relevant achievements in molecular recognition of glycans and their fragments will be summarized, highlighting potentials and future perspectives of glycan-targeting synthetic receptors.

The Acinetobacter baumannii K70 and K9 capsular polysaccharides consist of related K-units linked by the same Wzy polymerase and cleaved by the same phage depolymerases

ABSTRACT The extensively antibiotic-resistant Acinetobacter baumannii GC1(ST1 IP ) isolate SGH0807 from Singapore carries the KL70 gene cluster. The structure of the K70 capsular polysaccharide (CPS) produced by SGH0807 was determined using sugar analysis and one- and two-dimensional 1 H and 13 C NMR spectroscopy. The K70 CPS consists of branched tetrasaccharide K-units and is closely related to the previously reported K9 CPS. The KL70 and KL9 loci differ in a short segment that encodes the initiating transferase for d -Fuc p NAc in K70 and d -Glc p NAc in K9. The two structures differ only in the identity of the “first” sugar of the K-unit, d -Fuc p NAc in K70 and d -Glc p NAc in K9. This difference alters the identity of one of the sugars involved in the linkage between K-units formed by the Wzy polymerase. However, KL70 and KL9 encode an identical Wzy polymerase, designated as Wzy KL9 , indicating that the differences between d -Fuc p NAc and d -Glc p NAc do not affect its function. Whether the difference in the first sugars was recognized by the depolymerases encoded by three K9-specific bacteriophages, AM24, BS46, and APK09, that hydrolyze the bond in K9 CPS formed by Wzy KL9 was also examined. Purified depolymerases incubated with K70 CPS purified from SGH0807 formed oligosaccharide fragments that were monomers and dimers of the CPS cleaved at the linkage between K-units. As depolymerases encoded by phage determine host specificity by hydrolyzing specific CPS types, these phages could infect and lyse the SGH0807 K70 isolate. A. baumannii carrying KL70 were found in Singapore hospitals between 2006 and 2009. IMPORTANCE Bacteriophage show promise for the treatment of Acinetobacter baumannii infections that resist all therapeutically suitable antibiotics. Many tail-spike depolymerases encoded by phage that are able to degrade A. baumannii capsular polysaccharide (CPS) exhibit specificity for the linkage present between K-units that make up CPS polymers. This linkage is formed by a specific Wzy polymerase, and the ability to predict this linkage using sequence-based methods that identify the Wzy at the K locus could assist with the selection of phage for therapy. However, little is known about the specificity of Wzy polymerase enzymes. Here, we describe a Wzy polymerase that can accommodate two different but similar sugars as one of the residues it links and phage depolymerases that can cleave both types of bond that Wzy forms.

Convergent synthesis and immunological study of oligosaccharide derivatives related to galactomannan from Antrodia cinnamomea

The galactomannan from Antrodia cinnamomea (AC) is characterized as one of the important bioactive components that exhibits potential immunostimulatory propriety. The biological function of its corresponding oligosaccharide fragments has not been revealed yet. In this study, we reported the first chemical synthesis of the series of oligosaccharide fragments related to AC galactomannan via the convergent glycosylation strategy. The preliminary immunological evaluation of these synthesized AC oligosaccharides disclosed that the backbone tetrasaccharide 1d showed the best immunomodulatory ability on enhancing proliferation, phagocytosis and cytokines secretion of Raw264.7 macrophages in vitro, indicating its immense potential as an immunostimulant candidate.

An integrated strategy for rapid discovery and identification of the potential effective fragments of polysaccharides from Saposhnikoviae Radix

Ethnopharmacological relevanceSaposhnikoviae Radix (SR) is a traditional Chinese medicine, known as “Fangfeng”. As one of the main active components, Saposhnikoviae Radix polysaccharides (SP) demonstrated a range of biological activities, especially immunity regulation activity. Aims of the studyThis study aimed at exploring whether polysaccharides have activity after degradation, then discovering the potential effective fragments of SP. Materials and methodsHere we establish the chromatographic fingerprints method for 32 batches of 1-phenyl-3-methyl-5-pyrazolone (PMP) derivatives of oligosaccharides by HPLC, meanwhile evaluating its immunomodulatory activity in vivo. Then, the potential effective fragments of SP were screened out based on the spectrum-effect relationship analysis between fingerprints and the pharmacological results. Besides, liquid chromatography ion trap-time of flight mass spectrometry (LC-IT-TOF MS) coupled with multiple data-mining techniques was used to identify the potential effective oligosaccharides. ResultsThese findings showed that the hydrolysate of SP have significant immunomodulatory, and the immunity regulation activity varies under different hydrolysis conditions. The 4 potential effective peaks of the hydrolysate of SP were mined by spectrum-effect relationship. Finally, the chemical structure of 4 potential effective oligosaccharide fragments of SP was elucidated based on LC-IT-TOF MS. F10 was inferred tentatively to be Hex1→6Hex1→6Hex1→6Hex1→6Hex1→6Gal; F18 was confirmed to be Rhamnose; F14 was inferred tentatively to be Hex1→4Hex1→ 4Hex1→4Gal and F25 was tentatively inferred to be Ara1→6Gal. ConclusionsThis study may provide a sound experimental foundation in the exploration of the active fragments from macromolecular components with relatively complex structures such as polysaccharides.

Fingerprinting of Underivatized Monosaccharide Stereoisomers Using High-Resolution Ion Mobility Spectrometry and Its Implications for Carbohydrate Sequencing.

Although carbohydrates are the most abundant biopolymers on Earth, there is currently no streamlined method to elucidate their complete sequence. Mass spectrometry (MS) alone is blind to many cases of isomerism and thus gives incomplete information for carbohydrates. Notably, the coexistence of numerous stereoisomeric monosaccharide subunits is of special concern. Over the last 10 years, the coupling of ion mobility spectrometry (IMS) with MS has kept gaining momentum─especially with the advent of high-resolution (HR) IMS devices such as cyclic IMS (cIMS). In fact, IMS is sensitive to the gas-phase conformations of molecules and, thus, to stereoisomerisms. In this article, we present innovative ion mobility methods on a cIMS instrument that allowed us to build a database of HR-IMS fingerprints for various underivatized monosaccharide stereoisomers. The conditions were fully compatible with MS/MS fragmentation approaches. We further verify that these fingerprints afford the identification of monosaccharidic fragments released upon collisional fragmentation of oligosaccharides. Overall, these results pave the way toward direct sequencing of carbohydrates at the monosaccharide level using HR-IMS.

Friunavirus Phage-Encoded Depolymerases Specific to Different Capsular Types of Acinetobacter baumannii.

Acinetobacter baumannii is a critical priority nosocomial pathogen that produces a variety of capsular polysaccharides (CPSs), the primary receptors for specific depolymerase-carrying phages. In this study, the tailspike depolymerases (TSDs) encoded in genomes of six novel Friunaviruses, APK09, APK14, APK16, APK86, APK127v, APK128, and one previously described Friunavirus phage, APK37.1, were characterized. For all TSDs, the mechanism of specific cleavage of corresponding A. baumannii capsular polysaccharides (CPSs) was established. The structures of oligosaccharide fragments derived from K9, K14, K16, K37/K3-v1, K86, K127, and K128 CPSs degradation by the recombinant depolymerases have been determined. The crystal structures of three of the studied TSDs were obtained. A significant reduction in mortality of Galleria mellonella larvae infected with A. baumannii of K9 capsular type was shown in the example of recombinant TSD APK09_gp48. The data obtained will provide a better understanding of the interaction of phage-bacterial host systems and will contribute to the formation of principles of rational usage of lytic phages and phage-derived enzymes as antibacterial agents.

Identification of Pseudomonas aeruginosa exopolysaccharide Psl in biofilms using 3D OrbiSIMS.

Secondary ion mass spectrometry (SIMS) offers advantages over both liquid extraction mass spectrometry and matrix assisted laser desorption mass spectrometry in that it provides the direct in situ analysis of molecules and has the potential to preserve the 3D location of an analyte in a sample. Polysaccharides are recognized as challenging analytes in the mass spectrometry of liquids and are also difficult to identify and assign using SIMS. Psl is an exopolysaccharide produced by Pseudomonas aeruginosa, which plays a key role in biofilm formation and maturation. In this Letter, we describe the use of the OrbiTrap analyzer with SIMS (3D OrbiSIMS) for the label-free mass spectrometry of Psl, taking advantage of its high mass resolving power for accurate secondary ion assignment. We study a P. aeruginosa biofilm and compare it with purified Psl to enable the assignment of secondary ions specific to the Psl structure. This resulted in the identification of 17 peaks that could confidently be ascribed to Psl fragments within the biofilm matrix. The complementary approach of the following neutral loss sequences is also shown to identify multiple oligosaccharide fragments without the requirement of a biological reference sample.

Multiple Fingerprint-Activity Relationship Assessment of Immunomodulatory Polysaccharides from Ganoderma lucidum Based on Chemometric Methods.

Polysaccharides with molecular weights ranging from 1.75 × 103 to 1.14 × 104 g/mol were obtained from the fruit bodies of Ganoderma lucidum. The multiple fingerprints and macrophage immunostimulatory activity of these fractions were analyzed as well as the fingerprint-activity relationship. The correlation analysis of molecular weight and immune activity demonstrated that polysaccharides with molecular weights of 4.27 × 103~5.27 × 103 and 1 × 104~1.14 × 104 g/mol were the main active fractions. Moreover, the results showed that galactose, mannose, and glucuronic acid were positively related to immunostimulatory activity. Additionally, partial least-squares regression and grey correlation degree analyses indicated that three peaks (P2, P3, P8) in the oligosaccharide fragment fingerprint significantly affected the immune activity of the polysaccharides. Hence, these ingredients associated with activity could be considered as markers to assess Ganoderma lucidum polysaccharides and their related products, and the study also provides a reference for research on the spectrum-effect relationship of polysaccharides in the future.

Bioactivity of Walnut: Investigating the Triterpenoid Saponin Extracts of Juglans regia Kernels for Antioxidant, Anti-diabetic, and Antimicrobial Properties

The increasing demand for plant-based medicines makes plant research attractive to find natural alternatives that can replace synthetic products or at least reduce their use. Saponins are a group of natural phytochemical compounds in most herbs, vegetables, and legumes. There are two different types of saponin compounds, which can be classified based on the nature of the aglycone bound to the oligosaccharide fragments, whether it is a steroid or triterpenoid. This paper is devoted to saponins with triterpenoid aglycone and aims to study the relationship between their content and several biological activities in different Juglans regia kernel extracts, including antioxidant, antimicrobial and antibacterial activities. Antioxidant activity was assessed against two free radicals: DPPH and ABTS. Oleanolic acid was used as a standard to quantify triterpenoid saponins, measured by the vanillin method, whereas Acarbose and Tetracycline were used as positive controls to evaluate the α-glucosidase inhibitory and antimicrobial activities, respectively, of walnut kernel extracts. Findings show that hydroalcoholic extract (EtOH 70%) has a considerable content of phenolic compounds, with 59.51 ± 0.26 mg GAE/g in total polyphenol contents, while the content of total flavonoids and condensed tannins were 3.14 ± 0.27 mg QE/g and 85.65 ± 0.37 mg CE/g of crude extract, respectively. In terms of antioxidant activity, the butanolic extract proved to be the most effective against DPPH with IC50 = 7.74 ± 1.49 µg/mL, while the precipitated extract showed the highest scavenging activity against the ABTS free radical with IC50 = 33.14 ± 2.96 µg/mL. In addition, butanolic and hydroalcoholic extracts of Juglans regia kernels showed an α-glucosidase inhibitory activity even more efficiently than synthetic drugs such as Acarbose, with IC50 values of 11.66 µg/mL and 16.17 µg/mL, respectively, versus 18.01 µg/mL in Acarbose. The evaluation of the antimicrobial activity against Bacillus subtilis, Escherichia coli and Klebsiella pneumonia strains revealed that some extracts could inhibit these bacteria. This study successfully assessed the bioactivities of the extracts, suggesting that the extracts of medicinal plants can demonstrate stronger bioactivity than pure synthetic compounds.

Oligosaccharide analysis of the backbone structure of the characteristic polysaccharide of Dendrobium officinale

The backbone of Dendrobium officinale polysaccharide (DOP) was reported to be glucomannan. But the dispute continues due to the limitation of conventional analysis methods (e.g., the overlapped NMR signals). Herein, we describe an oligosaccharide sequencing analysis that successfully corrects the backbone to mannan. This analysis involves producing oligosaccharide fragments from mild acid hydrolysis of DOP followed by p -aminobenzoic ethyl ester (ABEE) derivatization. Then, a series of oligosaccharides with varied polymerization degrees (DP = 2–10) were isolated and identified by LC-MS profiling, monosaccharide composition analysis, linkage analysis, and 1D-/2D-NMR elucidation. Finally, we conclude that the backbone of DOP is a β -D-1,4-mannan which is confirmed by other analyses such as comparison with reference mannan. This oligosaccharide analysis is more straightforward and reliable by transforming the complicated polymers into oligomers which have more accurate and convincing MS and NMR data. • An oligosaccharide analysis method was proposed to characterize the DOP. • A series of oligomers and isomers from hydrolyzed DOP were isolated and identified. • An LC-MS method was established to test the oligomers' sugar sequence. • The backbone structure of DOP was corrected to be a β -D-1,4-Mannan.

Characterization and Comparison of Bioactive Polysaccharides from Grifola frondosa by HPSEC-MALLS-RID and Saccharide Mapping Based on HPAEC-PAD

Grifola frondosa polysaccharides (GFPs) from different regions in China were characterized and compared using HPSEC-MALLS-RID and saccharide mapping based on HPAEC-PAD analysis for achieving and improving its quality control. The results showed that HPSEC chromatograms and molecular weight distributions of GFPs were similar. The average contents of each polysaccharide fraction (Peaks 1, 2, and 3) showed that Peak 3 was the main component and much higher than the other two polysaccharide fractions, which also contained protein. The result of saccharide mapping showed that α-1,4-glycosidic, β-1,4-glycosidic and few β-1,3-glycosidic linkages were existed in GFPs. The similarity result showed that HPAEC-PAD fingerprints of the oligosaccharide fragments after hydrolysis by endoglycosidase were certainly different, especially α-amylase with a mean similar index of only 0.781 ± 0.207. The result of hierarchical cluster analysis (HCA) showed that different batches of GFPs from China can be divided into different clusters. Furthermore, immune-enhancing activity based on RAW 264.7 cells showed significant differences among different GFPs. Based on grey relational analysis (GRA), the fractions of Peak 3 were regarded as the major contributors to its immuno-enhancing activity in GFPs. Overall, the implications from these results were found to be stable, comprehensive, and valid for improving the quality control of GFPs.

Changes in the content of fucoglycoproteins in the mucous membranes and walls of the stomach and small intestine of alcoholized rats under immobilization stress

The article highlights the features of the metabolism of fucoglycoproteins in liver homogenates, the wall and mucous membrane of the stomach and small intestine in experimental models: alcoholic liver disease and prolonged alcoholization of rats under immobilization stress. Fucoglycoprotein metabolism was assessed for 90 days by the level of total fucose and fucosidase activity. To evaluate the implementation of the experiments, a biochemical analysis of markers of liver pathology was carried out. In the dynamics of experiments, there was an increase in transaminases and dyslipidemia in the blood serum of rats, as well as an increase in the level of corticosterone, especially in rats against the background of immobilization stress. In the exchange of fucose-containing glycoproteins in the blood serum, in the tissues of the liver, stomach and small intestine of experimental animals, multidirectional metabolic changes were monitored, namely, an increase in catabolism processes in the first days of observations in alcoholized rodents, which may be associated with the cytolytic effect of ethanol in the studied tissues. In these organs, the total amount of fucose is higher in the mucosa layer than in the organ wall. At the same time, in a series of experiments with immobilization stress against the background of ethanol administration, activation of anabolism of oligosaccharide fragments for the synthesis of fucoglycoproteins was noted in the second half of the experiment, associated with compensatory adaptive mechanisms.