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• A new glycosaminoglycan (LF-GAG) was obtained from the slug Limacus flavus. • Physicochemical properties of LF-GAG were analyzed. • Four oligosaccharides were obtained by deacetylation-deamination and purification. • The precise structure of LF-GAG was determined. • Structure and heparinase inhibitory activity relationships were discussed. A new glycosaminoglycan (LF-GAG) was purified from the slug Limacus flavus. Its unique chemical structure and heparanase inhibitory activity were studied in this work. The native LF-GAG was composed of L-iduronic acid (L-IdoA) and N -acetyl-D-glucosamine (D-GlcNAc), with a Mw of 22,700 Da. To elucidate the precise structure and structure-activity relationship, its deacetylation-deaminative depolymerized product (dLF-GAG) was prepared, and from which four oligosaccharides were purified. Combining the NMR spectral analysis of LF-GAG and its derived oligosaccharides, the structure of LF-GAG was deduced to be -4)-L-IdoA 2R -(α1,4)-D-GlcNAc-(α1-, in which R was −OH (˜80%) or –OSO 3 − (˜20%). Bioactivity assays showed that LF-GAG could potently inhibit human heparanase (IC 50 , 0.10 μM). dLF-GAG and LF-3 were less potent but also active for heparanase inhibition. Structure-activity relationship analysis indicated that the chain length and sulfate substitution of LF-GAG are essential for its heparanase inhibitory activity. [ABSTRACT FROM AUTHOR]

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

Edible snails have been widely used as a health food and medicine in many countries. A unique glycosaminoglycan (AF-GAG) was purified from Achatina fulica . Its structure was analyzed and characterized by chemical and instrumental methods, such as Fourier transform infrared spectroscopy, analysis of monosaccharide composition, and 1D/2D nuclear magnetic resonance spectroscopy. Chemical composition analysis indicated that AF-GAG is composed of iduronic acid (IdoA) and N -acetyl-glucosamine (GlcNAc) and its average molecular weight is 118 kDa. Structural analysis clarified that the uronic acid unit in glycosaminoglycan (GAG) is the fully epimerized and the sequence of AF-GAG is →4)-α-GlcNAc (1 → 4)-α-IdoA2S (1→. Although its structure with a uniform repeating disaccharide is similar to those of heparin and heparan sulfate, this GAG is structurally highly regular and homogeneous. Anticoagulant activity assays indicated that AF-GAG exhibits no anticoagulant activities, but considering its structural characteristic, other bioactivities such as heparanase inhibition may be worthy of further study. [ABSTRACT FROM AUTHOR]

• Oligosaccharide fractions H1 – H4 from depolymerized HcFG was purified and characterized. • HcFG was deduced as -{→4)-[ l -FucS-α(1→3)]- d -GlcA-β(1→3)- d -GalNAc 4S6S - β(1}n-. • FG branched with Fuc 3S4S was susceptible to β -eliminative depolymerization. • Anticoagulant activities of native and depolymerized HcFG were assessed. A glycosaminoglycan was isolated from the sea cucumber Holothuria coluber (HcFG). A series of oligosaccharide fragments (dp range 3–11) were prepared from its β -eliminative depolymerized product (dHcFG). Extensive NMR characterization of the oligosaccharides indicated the d -GlcA- β 1,3- d -GalNAc 4S6S repeating disaccharide backbone was substituted by monosaccharide branches comprising of Fuc 2S4S , Fuc 3S4S and Fuc 4S , linked to O-3 of d -GlcA. For the prevailing Fuc 3S4S at nonreducing end of dHcFG, the β- eliminative depolymerization process of HcFG was compared with those of the FGs from Actinopyga miliaris (AmFG, branched with Fuc 3S4S) and Stichopus variegatus (SvFG, branched with Fuc 2S4S). The result suggested that d -GlcA substituted with Fuc 3S4S was more susceptible to depolymerization than that with Fuc 2S4S. It might be due to the larger steric hindrance effects from Fuc 2S4S on the esterification of GlcA. Biological assays confirmed that the minimum chain length (dp8), regardless of the Fuc branch types, was required for the potent anti-iXase and anticoagulant activities in FG fragments. [ABSTRACT FROM AUTHOR]