Clarhammoside from the marine sponge Agelas clathrodes is a specialized glycosphingolipid that has attracted the attention of scientists due to its novel structure with a terminal rhamnose unit. CD BioGlyco has a team of experts dedicated to Marine Glycosphingolipid research to provide trusted clarhammoside services to our clients.
The sponge is pulverized and a specific amount of methanol and chloroform mixture is added to it to extract the clarhammoside. After some time, the sponge residue is filtered and removed. At this point, the methanol and chloroform mixture containing clarhammoside is partitioned between water and BuOH, and the organic layer is collected. After concentrating on the organic layer, a crude product of clarhammoside will be obtained.
Initial purification of crude clarhammoside on silica gel and SiO2 columns led to a mixture of clarhammoside and other glycolipids. The mixture of clarhammoside and other glycolipids is acetylated, the other glycolipids are removed by high-performance liquid chromatography (HPLC), and the fraction containing acetylated clarhammoside is collected. Finally, the acetylated clarhammoside is deacetylated to obtain a pure product of clarhammoside.
On the other hand, our professional Marine Glycolipid R&D team also provides the chemical synthesis solution of clarhammoside for our clients.
Since the structure of the glycan chain of clarhammoside is characterized by the fact that the inner galactose is connected to ceramide via an α-glycosidic bond, and the 2-position of this glycan is connected to another galactose via an α-glycosidic bond, we synthesize clarhammoside by dividing it into four blocks and synthesizing them individually, and by connecting the four blocks in sequence via the stepwise extension method. For chemically synthesized clarhammoside, we similarly use the above analysis method to analyze the properties of clarhammoside.
Technology: Solvent extraction, NMR, ESI-MS
Journal: Marine Drugs
IF: 4.9
Published: 2018
Results: In this article, the authors show the extraction and isolation of marine natural glycosphingolipid clarhammoside from sponges. The extraction and isolation of clarhammoside was carried out by organic solvent extraction and its purification was carried out by chromatographic techniques. Finally, the structure of clarhammoside was characterized by NMR and ESI-MS. Clarhammoside is an α-galactosyl sphingolipid with an l-rhamnose unit at the end of the sugar chain, and two consecutive 1,2-cis-α-d-galactopyranoside bonds are also present.
Fig.1 The structure of clarhammoside. (Cheng-Sánchez & Sarabia, 2018)
What are the structural features of clarhammoside?
The structure of clarhammoside is α-L-Rhap-(1→3)-β-D-NHAcGalp-(1→6)-α-Galp-(1→2)-α-Galp-ceramide. The structure of the glycan chain of this compound is characterized by the connection of the inner galactose to ceramide via an α-glycosidic bond, and the 2-position of this glycan is connected to another galactose via an α-glycosidic bond.
What are the biological activities of clarhammoside?
Clarhammoside is an important biologically active molecule that contains a variety of biological activities. For example, clarhammoside is involved in neuronal and glial cell recognition and adhesion, and the regulation of intercellular signaling and cellular communication. Clarhammoside also plays an important role in the immune system, participating in the regulation of immune response and pathogen recognition by interacting with receptors on the surface of immune cells.
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