Shuyao Wang

Structural characterization and anticoagulant activity of a sulfated polysaccharide from the green alga Codium divaricatum

A sulfated polysaccharide, designated CP2-1, was isolated from the green alga Codium divaricatum by water extraction and purified by anion-exchange and size-exclusion chromatography. CP2-1 is a galactan which is highly sulfated and substituted with pyruvic acid ketals. On the basis of chemical and spectroscopic analyses, the backbone of CP2-1 was mainly composed of (1→3)-β-d-galactopyranose residues, branched by single (1→)-β-d-galactopyranose units attached to the main chain at C-4 positions. The degree of branching was estimated to be about 12.2%. Sulfate groups were at C-4 of (1→3)-β-d-galactopyranose and C-6 of non-reducing terminal galactose residues. In addition, the ketals of pyruvic acid were found at 3,4- of non-reducing terminal galactose residues forming a five-membered ring. CP2-1 possessed a high anticoagulant activity as assessed by the activated partial thromboplastin time and thrombin time assays. The investigation demonstrated that CP2-1 was an anticoagulant-active sulfated polysaccharide distinguishing from other sulfated polysaccharides from marine green algae.

Galactomannan with novel structure produced by the coral endophytic fungus Aspergillus ochraceus

The homogeneous extracellular polysaccharide, AW1, was obtained from the fermented broth of the fungus Aspergillus ochraceus derived from coral Dichotella gemmacea. AW1 was a galactomannan with a molar ratio of mannose and galactose of 2.16:1.00 and a molecular weight of about 29.0kDa. The structure of AW1 was investigated by chemical and spectroscopic methods, including methylation analysis, one- and two-dimensional nuclear magnetic resonance (1D, 2D NMR) and electrospray mass spectrometry with collision-induced dissociation (ES-CID MS/MS) spectroscopic analyses. The results showed that the backbone of AW1 consisted of (1⟶2)-linked α-d-mannopyranose residues. The mannopyranose residues in the backbone were substituted at C-6 by the (1⟶)-linked α-d-mannopyranose units and (1⟶5)-linked β-d-galactofuranose oligosaccharides with different degrees of polymerization. The investigation demonstrated that AW1 was a novel galactomannan with different structural characteristics from other fungal galactomannans, and could be a potential resource of the (1⟶5)-linked β-d-galactofuranose oligosaccharides.

Structure and anticoagulant property of a sulfated polysaccharide isolated from the green seaweed Monostroma angicava

An anticoagulant-active polysaccharide PF2 was extracted with boiling water from the green seaweed Monostroma angicava, further purified by anion-exchange and size-exclusion chromatography. PF2 was a rhamnan-type sulfated polysaccharide with molecular weight of about 88.1kDa. Results of chemical and spectroscopic analyses demonstrated that PF2 consisted of→3)-α-l-Rhap-(1→ and →2)-α-l-Rhap-(1→residues, with partially branches at C-2 of→3)-α-l-Rhap-(1→residues. Sulfate groups were substituted at C-3 of →2)-α-l-Rhap-(1→ residues. The sulfated polysaccharide PF2 had a high anticoagulant action, and the mechanism of anticoagulant activity mediated by PF2 was mainly attributed to strong potentiation thrombin by heparin cofactor II. PF2 also exhibited weak effect on antithrombin-dependent thrombin or factor Xa inhibition. The fibrin(ogen)olytic activity and thrombolytic activity of PF2 were also evaluated. The investigation revealed that PF2 was a novel sulfated rhamnan differing from previously described sulfated polysaccharides from green seaweed and could be a potential anticoagulant polysaccharide.

Extracellular polysaccharide with novel structure and antioxidant property produced by the deep-sea fungus Aspergillus versicolor N2bc.

An extracellular polysaccharide, N1, was obtained from the culture medium of the deep-sea fungus Aspergillus versicolor N2bc by a combination of ethanol precipitation, ion-exchange and gel filtration chromatography. N1 was a mannoglucogalactan with molecular weight of about 20.5kDa. Results of chemical and spectroscopic analyses, including Fourier-transform infrared, one- and two-dimensional nuclear magnetic resonance spectroscopy showed that the main chain of N1 consisted of →2)-α-d-Glcp-(1→, →2)-β-d-Glcp-(1→ and →6)-β-d-Manp-(1→ units, substituted at C-6 position of →2)-α-d-Glcp-(1→ units. The branches were composed of galactofuranose-oligosaccharides built up of →5)-β-d-Galf-(1→, →6)-β-d-Galf-(1→ and terminal β-d-Galf units. At an average, there were two branching points for every five sugar residues in the backbone. N1 possessed a high in vitro antioxidant activity as evaluated by scavenging assays involving superoxide, 1,1-diphenyl-2-picrylhydrazyl, hydroxyl radicals and reducing power. The investigation revealed that N1 was a novel antioxidant polysaccharide differing from previously described extracellular polysaccharides and could be a potential antioxidant.

Structural elucidation of the exopolysaccharide produced by the mangrove fungus Penicillium solitum.

A water soluble extracellular polysaccharide, designated GW-12, was obtained from the liquid culture broth of the mangrove fungus Penicillium solitum by ethanol precipitation, anion-exchange and size-exclusion chromatography. Reversed-phase high performance liquid chromatography analysis showed that GW-12 mainly consisted of d-mannose, and its molecular weight was estimated to be about 11.3 kDa determined by high performance gel permeation chromatography. On the basis of chemical and spectroscopic analyses, including methylation analysis and nuclear magnetic resonance (NMR) spectroscopy, the structure of GW-12 may be represented as a mannan with branches. The main chain of GW-12 was composed of (1 → 2)-linked α-D-mannopyranose and (1 → 6)-linked α-D-mannopyranose residues, branched by single α-d-mannopyranose units attached to the main chain at C-6 positions of (1 → 2)-linked α-D-mannopyranose residues. There was three branch points for every seven sugar residues in the backbone.

An Overview of the Protective Effects of Chitosan and Acetylated Chitosan Oligosaccharides against Neuronal Disorders

Chitin is the second most abundant biopolymer on Earth and is mainly comprised of a marine invertebrate, consisting of repeating β-1,4 linked N-acetylated glucosamine units, whereas its N-deacetylated product, chitosan, has broad medical applications. Interestingly, chitosan oligosaccharides have therapeutic effects on different types of neuronal disorders, including, but not limited to, Alzheimer’s disease, Parkinson’s disease, and nerve crush injury. A common link among neuronal disorders is observed at a sub-cellular level, such as atypical protein assemblies and induced neuronal death. Chronic activation of innate immune responses that lead to neuronal injury is also common in these diseases. Thus, the common mechanisms of neuronal disorders might explain the general therapeutic effects of chitosan oligosaccharides and their derivatives in these diseases. This review provides an update on the pathogenesis and therapy for neuronal disorders and will be mainly focused on the recent progress made towards the neuroprotective properties of chitosan and acetylated chitosan oligosaccharides. Their structural features and the underlying molecular mechanisms will also be discussed.

A rhamnan-type sulfated polysaccharide with novel structure from Monostroma angicava Kjellm (Chlorophyta) and its bioactivity

A homogeneous polysaccharide was obtained from Monostroma angicava Kjellm by water extraction, preparative anion-exchange and size-exclusion chromatography. Results of chemical and spectroscopic analyses showed that the polysaccharide was a glucuronic acid-containing rhamnan-type sulfated polysaccharide. The backbone mainly consisted of →3)-α-l-Rhap-(1→ and →2)-α-l-Rhap-(1→ residues, partially sulfated at C-2 of →3)-α-l-Rhap-(1→ and C-3/C-4 of →2)-α-l-Rhap-(1→. The branching contained unsulfated or monosulfated 3-linked, 2-linked, 4-linked α-l-rhamnose and terminal β-d-glucuronic acid residues. The polysaccharide had strong antidiabetic activity assessed by glucose consumption, total cholesterol and triglyceride levels using human hepatocellular carcinoma (HepG2) and insulin-resistant HepG2 cells. The polysaccharide exhibited high anticoagulant property by activated partial thromboplastin time and thrombin time assays, and possessed high fibrin(ogen)olytic activity evaluated by plasminogen activator inhibitior-1, fibrin(ogen) degradation products and D-dimer levels using rats plasma. The investigation demonstrated that the polysaccharide from Monostroma angicava Kjellm was a novel sulfated rhamnan and could be a potential antidiabetic and anticoagulant polysaccharide.

Structural Characteristics and Anticoagulant Property In Vitro and In Vivo of a Seaweed Sulfated Rhamnan

Great diversity and metabolite complexity of seaweeds offer a unique and exclusive source of renewable drug molecules. Polysaccharide from seaweed has potential as a promising candidate for marine drug development. In the present study, seaweed polysaccharide (SPm) was isolated from Monostroma angicava, the polymeric repeat units and anticoagulant property in vitro and in vivo of SPm were investigated. SPm was a sulfated polysaccharide which was mainly constituted by 3-linked, 2-linked-α-l-rhamnose residues with partially sulfate groups at C-2 of 3-linked α-l-rhamnose residues and C-3 of 2-linked α-l-rhamnose residues. Small amounts of xylose and glucuronic acid exist in the forms of β-d-Xylp(4SO4)-(1→ and β-d-GlcA-(1→. SPm effectively prolonged clotting time as evaluated by the activated partial thromboplastin time and thrombin time assays, and exhibited strong anticoagulant activity in vitro and in vivo. The fibrin(ogen)olytic and thrombolytic properties of SPm were evaluated by plasminogen activator inhibitior-1, fibrin degradation products, D-dimer and clot lytic rate assays using rats plasma, and the results showed that SPm possessed high fibrin(ogen)olytic and thrombolytic properties. These results suggested that SPm has potential as a novel anticoagulant agent.

Antiviral activity against enterovirus 71 of sulfated rhamnan isolated from the green alga Monostroma latissimum

Polysaccharide from Monostroma latissimum PML is a sulfated rhamnan, which consists of →3)-α-L-Rhap-(1→ and →2)-α-L-Rhap-(1→ residues with partial branches and sulfate groups at C-2 of →3)-α-L-Rhap-(1→ and/or C-3 of →2)-α-L-Rhap-(1→. The anti-enterovirus 71 (EV71) activity in vitro of PML was assessed by cytopathic effect inhibition and plaque reduction assays, and the results showed that PML was non-cytotoxic and significantly inhibited EV71 infection. The mechanism analysis of anti-EV71 activity demonstrated that PML largely inhibited viral replication before or during viral adsorption, mainly by targeting the capsid protein VP1. PML may also inhibit some early steps of infection after viral adsorption by modulating signaling through the epidermal growth factor receptor (EGFR)/phosphoinositide 3-kinase (PI3K)/protein kinase B (Akt) pathway. Moreover, PML markedly improved survival and decreased viral titers in EV71-infected mice. The investigation revealed that PML has potential as a novel anti-EV71 agent targeting the viral capsid protein as well as cellular EGFR/PI3K/Akt pathway.