From Sea to Science: Premium Cucumarioside Production at CD BioGlyco
Cucumariosides are glycosides derived from sea cucumbers, particularly species like Cucumaria japonica and Eupentacta fraudatrix. These compounds possess complex structures featuring a triterpene backbone with various sugar moieties and sulfate groups that define different cucumariosides. At CD BioGlyco, our production process involves several stages: initially, the sea cucumbers are freeze-dried, cut into pieces, and extracted twice with refluxing ethanol. The concentrated ethanol extracts are then dissolved in water and desalting is performed using a Polychrom column to remove inorganic salts and polar impurities, with the glycoside fraction eluted using ethanol. Further purification is achieved through silica gel column chromatography followed by reverse phase high-performance liquid chromatography (HPLC). Finally, the structures of cucumariosides are elucidated using spectroscopic techniques, along with gas chromatography-mass spectrometry (GC-MS) analysis of aldononitrile peracetates to determine monosaccharide units. We also offer a range of Marine Glycoside Production Services, allowing clients to select the most suitable solution for their research needs.
Extraction
To extract cucumariosides from sea cucumbers like Cucumaria japonica and Eupentacta fraudatrix, the freeze-dried and cut pieces are subjected to ethanol extraction using a reflux apparatus. This process is performed twice to maximize yield, with the combined ethanol extracts concentrated under reduced pressure and dissolved in distilled water to prepare for desalting.
Purification
The aqueous solution containing cucumariosides undergoes desalting using a Polychrom column, where salts and impurities are washed out with distilled water, followed by elution of glycosides with 50% ethanol. The glycoside fraction is then purified through silica gel column chromatography with a gradient solvent system and further refined using reverse phase HPLC, ensuring high purity of the final product.
Characterization
Purified cucumariosides are characterized using advanced spectroscopic techniques, including 1H nuclear magnetic resonance (NMR), 13C NMR, correlated spectroscopy (COSY), heteronuclear multiple bond correlation (HMBC), heteronuclear single quantum coherence (HSQC), and total correlation spectroscopy (TOCSY), to elucidate their structure. Additionally, Matrix-assisted laser desorption ionization-time of flight-MS (MALDI-TOF-MS) is employed to determine molecular weights and confirm structural components, while GC-MS analysis of aldononitrile peracetates helps identify monosaccharide units.
Quality Control
Quality control involves assessing the purity of cucumariosides through repeated HPLC analysis and comparison with known standards, using thin-layer chromatography (TLC) and HPLC to detect impurities or degradation products. The yield of cucumariosides is quantified relative to the starting material, and optimized protocols are recorded. Please feel free to visit our Marine Biomolecule Production Service if you are also interested in other marine-related molecules.
Publication
DOI: 10.1186/s12935-023-03141-z
Technology: Fluorescence microscopy imaging, Flow cytometry, Enzyme-linked immunosorbent assay (ELISA), Reverse transcription polymerase chain reaction (RT-PCR), Prussian blue staining, Tumor model establishment and treatment
Journal: Cancer Cell International
IF: 5.3
Published: 2023
Results: The main findings demonstrated that cucumarioside A2-2 significantly activates macrophages, inducing their polarization to the M1 phenotype and enhancing their antitumor activity. The study showed that cucumarioside A2-2-treated macrophages exhibited tumor growth suppression and extended survival in mice with Ehrlich carcinoma and 4T1 syngeneic models.
Fig.1 Strategy of cellular anticancer immunotherapy. (Chuang, et al., 2023)
Applications
- Cucumariosides can modulate immune responses, useful in studying immune-related diseases and developing immunotherapies.
- Due to their bioactive properties, cucumariosides can be formulated into supplements aimed at boosting immune function and overall health.
- Researchers can explore the relationship between the structure of cucumariosides and their biological activities, aiding in the design of more effective compounds.
Advantages
- CD BioGlyco ensures the production of high-purity cucumariosides through rigorous extraction, purification, and quality control processes, meeting the high standards required for research and commercial applications.
- With extensive expertise in marine glycoside production, CD BioGlyco offers reliable and efficient services backed by years of experience and a deep understanding of the field.
- From initial extraction to final characterization and quality control, CD BioGlyco provides a complete service package, ensuring seamless production and high-quality outcomes.
Frequently Asked Questions
What are cucumariosides and why are they important?
Cucumariosides are glycosides derived from sea cucumbers, known for their complex structures featuring triterpene and carbohydrate components. They have significant biological activities, including anti-inflammatory, immunomodulatory, and antitumor properties.
Which species of sea cucumbers are used for extracting cucumariosides?
CD BioGlyco primarily uses species like Cucumaria japonica and Eupentacta fraudatrix for extracting cucumariosides due to their high glycoside content and well-documented bioactivity.
At CD BioGlyco, our cucumariosides production service supports a wide range of research and commercial endeavors, contributing to advancements in pharmaceuticals, nutraceuticals, cosmetics, and biochemical studies. Please do not hesitate to contact us for more details about our production service and feel free to get in touch for your custom solution.
References
- Chuang, W.; et al. Holothurian triterpene glycoside cucumarioside A2-2 induces macrophages activation and polarization in cancer immunotherapy. Cancer Cell International. 2023, 23(1): 292.
- From Wikipedia: https://en.wikipedia.org/wiki/Cucumaria#/media/File:Cucumaria_miniata.jpg.
- From Wikipedia: https://en.wikipedia.org/wiki/Eupentacta#/media/File:Eupentacta_quinquesemita,_Explored._Stiff-footed_Sea_Cucumber.jpg.
- From Wikipedia: https://en.wikipedia.org/wiki/Liquid%E2%80%93liquid_extraction#/media/File:Funnels.jpg.
- From Wikipedia: https://en.wikipedia.org/wiki/High-performance_liquid_chromatography#/media/File:Agilent1200HPLC.jpg.
