Phalluside: Precision and Innovation in Production
Marine cerebrosides, a class of Marine Glycosphingolipids, are vital to eukaryotic cells and are also present in certain prokaryotic organisms and viruses. Predominantly localized in cellular membranes, cerebrosides contribute to structural integrity and texture. Their biological significance spans a wide array of functions, including mediating cell-cell communication, recognition, and adhesion. Furthermore, the metabolites of cerebrosides function as second messengers within cellular signaling pathways. Therefore, CD BioGlyco provides production services for these important substances. Here, we would like to introduce our phalluside production service by using rich marine resources.
Based on customer needs, we offer two production strategies.
Production by Extraction
- We use the marine organism Phallusia fumigata from the southern coast of Clidiz as the raw material. The raw material is frozen to preserve the chemical integrity and stability of its components until it is used.
- The frozen tissue is exhaustively extracted with an acetone-methanol mixture at room temperature.
- The filtered extract is evaporated under reduced pressure to remove solvents, leaving an aqueous residue.
- Subsequently, we extract the aqueous residue with diethyl ether to yield an oil residue.
- The oil residue is chromatographed on a SiO2 column using solvents of increasing polarity, ranging from hexane to diethyl ether, ethyl acetate, and eventually mixtures of increasing polarity from chloroform to methanol.
- Then collect fractions eluted with chloroform/methanol for further separation.
- We subject the collected fractions to reversed-phase high-performance liquid chromatography (HPLC) with a methanol/water elution system to yield target compounds, phallusides. Phalluside undergoes final purification by reversed-phase HPLC using a methanol/water elution system to achieve high purity.
Production by Synthesis
We also provide the production of phalluside by advanced synthetic techniques to synthesize its complex structure. Our synthesis process typically starts with the synthesis of the sphingatrienine backbone through precise chemical reactions, including the copper(I)-mediated rearrangement. This step is crucial for constructing the correct stereochemistry and functionality of the molecule. Once synthesized, the compound undergoes further transformations to yield phalluside.
Identification and Analysis
- Optical rotations are measured using a polarimeter to confirm the stereochemical properties of the compounds.
- Our researchers utilize infrared (IR) and ultraviolet (UV) spectroscopy to verify structural features.
- 1H nuclear magnetic resonance (NMR) and 13C NMR spectra are used to identify their structures.
- Mass spectra are recorded on a spectrometer to confirm molecular weight and structural information.
Publication Data
Technology: Layer chromatography, 1H NMR spectroscopy, Reversed-phase HPLC, Infrared spectroscopy, Ultraviolet spectroscopy
Journal: Ciencias marinas
Published: 2018
IF: 1.1
Results: In this study, the authors conducted a chemical study of marine ascidians from the Gibraltar Strait. They performed the isolation and characterization of new natural products with potential antitumor properties. Specifically, they extracted and isolated novel glycosphingolipids, termed phallusides 1-4, from P. fumigata. The structures of these compounds were determined using spectroscopic techniques and the Mosher method for absolute stereochemistry. The authors also evaluated the cytotoxicity of these compounds against several cancer cell lines to assess their antitumor potential.
Applications
- Phallusides are studied for their potential therapeutic effects, including their impact on cell signaling and their role as bioactive compounds in drug development.
- Phallusides can be used as tools for studying sphingolipid metabolism and the role of sphingolipids in cellular processes.
- Phallusides can be applied to investigate their structure and synthesis, helping to understand their chemical properties and potential applications in synthetic chemistry.
Advantages
- We offer advanced synthetic techniques for phalluside production, enabling the creation of complex structures with precise stereochemistry.
- We provide flexible production options based on customer needs, including extraction from natural sources and synthetic production.
- Our extraction processes utilize state-of-the-art methods to ensure the purity and efficacy of the phallusides obtained from marine organisms.
Frequently Asked Questions
What types of phallusides can we produce?
- Phallusides 1
- Phallusides 2
- Phallusides 3
- Phallusides 4
What are the benefits of synthetic production of phalluside?
Synthetic production provides precise control over the structure and purity of phalluside, allowing for the creation of complex and specific variants that may be challenging to obtain through natural extraction.
At CD BioGlyco, we ensure that all compounds meet the desired purity and quality standards before delivery to clients for research or application purposes. This comprehensive workflow ensures that we have the ability to produce high-purity Marine Biomolecules. If you want to obtain other Marine Glycolipids that meet the rigorous demands of research and application, contact us.
Reference
- Zubía, E.; et al. Antitumor potential of natural products from marine ascidians of the Gibraltar Strait: a survey. Ciencias marinas. 2003, 29(2): 251-260.
