Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
1020.0000
-8.5000
-8.5000
No
.0000
No
Negative
D-decamannuronic acid decasodium salt (product code BP4336) is a structurally clear marine derived oligosaccharide compound. Its chemical essence is a linear oligosaccharide chain composed of ten D-mannuronic acid units connected by glycosidic bonds, and exists in the form of decasodium salt to enhance its water solubility and stability. Although its precise molecular formula, molecular weight, and CAS number are not yet fully disclosed, it is inferred from its naming and structural units that it belongs to the enzymatic or chemical degradation products of brown algae polysaccharides (such as alginate), and is a specific polymerization degree fragment of the mannuronic acid (M) chain segment in alginate.
In the field of natural product research, polysaccharides and their oligosaccharide fragments contained in large algae derived from the ocean, such as kelp and horsetail algae, have become a hot topic in drug discovery and functional food development in recent years due to their rich biological activity and low toxicity. Mannuronic acid decaose is not directly derived from a specific plant, but is isolated and purified by controlled degradation (such as enzymatic hydrolysis, acid hydrolysis, or oxidative degradation) of alginate extracted from brown algae. This directional preparation method ensures the uniformity of its polymerization degree (decaose) and monosaccharide sequence (both mannuronic acid), providing a standard material basis for studying its structure-activity relationship and mechanism of action.
Research background shows that traditionally, alginate and its derivatives have been widely used in the food industry, pharmaceutical excipients and wound dressings due to their gel properties, biocompatibility and biodegradability. However, with the development of glycobiology and glycopharmacology, scientists have found that low molecular weight oligosaccharide fragments (such as mannuronic acid oligosaccharides) produced by the degradation of alginate exhibit more significant and specific biological activity than its high molecular weight parent. Especially oligosaccharides with specific degrees of polymerization may regulate key signaling pathways by simulating or interfering with sugar protein interactions on the cell surface. The existing pharmacological data preliminarily revealed the interaction between mannuronic acid decasaccharide and multiple targets closely related to metabolism and inflammation, suggesting that it has potential application value in the prevention and treatment of a series of major chronic diseases such as diabetes, cardiovascular disease, metabolic syndrome, etc. This article will provide a systematic professional popularization of this promising marine natural product from its chemical properties, pharmacological mechanisms, drug evaluation, and research prospects.
The chemical structure core of mannuronic acid decaose is a linear chain composed of D-mannuronic acid residues connected by ten β - (1 → 4) glycosidic bonds. D-mannuronic acid is a type of hexuronic acid, with a carboxyl group (- COOH) at the C6 position of the pyran ring. In the form of "decasodium salt", the carboxyl groups on each uronic acid unit are almost always present in the form of sodium carboxylate (- COONa), which endows the compound with strong hydrophilicity and high solubility in aqueous solution.
Molecular formula and molecular weight Although exact values are not provided, theoretical estimates can be made. The molecular weight of a D-mannuronic acid (C6H10O7) unit is approximately 194.14 Da. Ten units form glycosidic bonds through dehydration condensation, resulting in the loss of nine water molecules (9 × 18.02=162.18 Da). Therefore, the theoretical molecular weight of the free acid form of decaose is approximately (194.14 × 10) -162.18=1779.22 Da. When converted to decasodium salt, each carboxyl group (- COOH) becomes a sodium carboxylate (- COONa), equivalent to an increase of 22 Da per unit (Na atom replacing H atom), resulting in a total increase of 220 Da. Therefore, the theoretical molecular weight of its decasodium salt is approximately 1779.22+220= 1999.22 Da The molecular formula can be approximately estimated as C60H70O61Na10 (taking into account the difference between the reducing and oxidizing ends at the end, this is an estimate).
Physicochemical properties：
- solubility As a compound of polyhydroxy and polycarboxylate sodium salts, it has excellent water solubility and is almost insoluble in organic solvents such as ethanol, ethyl acetate, chloroform, etc.
- LogP (Fat Water Partition Coefficient)Expected to have extremely low negative values (such as -5 to -10 or even lower), indicating that it is a highly hydrophilic molecule that is difficult to passively diffuse through the cell membrane composed of lipid bilayers.
- acidity and alkalinity Its sodium carboxylate salt makes its aqueous solution weakly alkaline.
- Stability Under acidic conditions, sodium salts may transform into free acid forms and undergo acid catalyzed hydrolysis of glycosidic bonds. Relatively stable under neutral and alkaline conditions. It may be relatively stable to heat, but prolonged high-temperature treatment may also lead to degradation.
- Topological Polarity Surface Area (TPSA)Due to its high content of hydroxyl and carboxylate ions, its TPSA value is expected to be very high (expected to be much greater than 500 Å ²), which is a key negative factor affecting its membrane permeability.
Strictly speaking, mannuronic acid decaose is not a single component directly extracted from a certain plant, but a derivative of alginate, a cell wall polysaccharide derived from large marine brown algae. Therefore, its' source 'should be traced back to brown algae and their traditional applications.
Plant-based Alginate is mainly extracted from various types of seaweed in the Phaeophyceae phylum, including:
- Kelp genus（Laminaria SPP: Seaweed widely cultivated and consumed in China and East Asia.
- macrocystis（Macrocystis Spp.: such as giant brown algae along the Pacific coast.
- Sargassum genus（Sargassum SPP: Widely distributed in temperate and tropical waters.
These algae produce block copolymers composed of two units, β - D-mannuronic acid (M) and α - L-guluronic acid (G), arranged in different proportions and sequences through biosynthesis, known as alginates.
Traditional Applications：
1. Eating history Seaweed, seaweed, and other brown algae have a long history of consumption in East Asia (China, Japan, South Korea) and are often used to make soups, salads, and side dishes. They are believed to have traditional effects such as clearing heat and phlegm, softening hardness and dispersing lumps.
2. Industrial and pharmaceutical excipients Since alginate was separated at the end of the 19th century, its sodium salt, calcium salt and other derivatives have been widely used as food additives, textile printing and dyeing pastes, and auxiliary materials in the medical field (such as tablet adhesives, disintegrants, and hydrogel matrices for wound dressings) due to their gelling, thickening, stability and film forming properties.
3. Potential health benefits Traditional medicine and folk experience believe that consuming seaweed is beneficial to health. Preliminary modern research suggests that alginate and its partially degraded products may have potential benefits in regulating intestinal health (dietary fiber function), adsorbing heavy metals, assisting in weight and blood sugar control, and so on.
However, traditional applications are mainly based on bulk mixtures or high molecular weight forms of alginate. Mannuronic acid decaose, as a specific oligosaccharide with uniform structure prepared by modern biotechnology or chemical methods, often has clearer and more efficient biological activity, representing a modern research direction for exploring high-value functional molecules from traditional natural materials.
The pharmacological activity data of mannuronic acid decaose is mainly reflected in its interactions with eight key biological targets, which are widely involved in inflammatory response, metabolic regulation, insulin signaling, and immune regulation. Its mechanism of action may not be through direct inhibition or activation of enzyme activity, but rather as a "signaling molecule" that binds to pattern recognition receptors (such as TLR4) or other signaling proteins on the cell membrane to initiate or regulate downstream signaling cascades, thereby exerting beneficial effects on various related diseases.
Core target and mechanism analysis:
Anti inflammatory and immune regulatory core: TLR4/NF - κ B/MAPK/cytokine axis
Disease association This series of effects makes it effective Inflammatory diseases(such as rheumatoid arthritis, inflammatory bowel disease)Metabolic syndrome、Non alcoholic fatty liver disease (NAFLD)(Its onset is closely related to liver inflammation) and cardiovascular disease(Atherosclerosis is a chronic inflammatory disease in essence) has potential therapeutic value.
Metabolic regulation and insulin sensitization
Disease association By acting on targets such as PPARG, SLC2A4, and AdipoR1, mannuronic acid decasaccharides have the potential to improve insulin resistance, promote glucose utilization, and regulate lipid metabolism through multiple pathways, thereby improving Type 2 diabetes、obesity、Metabolic syndrome and NAFLD Generate comprehensive benefits.
Mechanism of Action Integration Landscape：
Mannuronic acid decaose may first be recognized by TLR4 on the cell membrane of immune cells (such as macrophages) or metabolically active tissues (such as adipose tissue, liver) through its sugar chain structure. Unlike the activation effect of LPS, it may act as an "antagonist" or "modulator" to inhibit the excessive activation of TLR4, thereby Reduce chronic low-grade inflammatory state The alleviation of inflammation helps to restore the sensitivity of the insulin signaling pathway (improve SLC2A4 function) and may synergistically regulate the function of metabolic nuclear receptors such as PPARG. Meanwhile, it may directly or indirectly affect receptors such as AdipoR1. This multi target, network type regulation mode just fits in with the pathological characteristics of multiple causes of complex chronic diseases such as diabetes, cardiovascular disease, etc., that is, through both anti-inflammatory and metabolic regulation, to achieve comprehensive therapeutic effects.
Drug efficacy assessment aims to predict the likelihood of a compound developing into an oral or injectable drug. Based on the Lipinski Rule of Five (primarily applicable to oral medications) and known physicochemical properties, we can conduct a preliminary analysis of the pharmacological potential of mannuronic acid decaose.
Evaluation based on existing information:
Lipinski's Five Rules Analysis：
Conclusion Mannuronic acid decaose seriously violates multiple of Lipinski's five rules (molecular weight, HBD, HBA), clearly indicating its Oral bioavailability will be very low It is difficult to enter the bloodstream through passive diffusion across the epithelial cell membrane of the gastrointestinal tract.
Other key pharmacological parameters：
Comprehensive drug evaluation and development strategy:
Mannuronic acid decaose as a Highly polar and high molecular weight oligosaccharide compounds, its Oral administration faces significant challenges The conventional oral small molecule drug development model is not applicable. However, this does not mean that it has no potential as a drug. Its development strategy should shift towards:
Therefore, although it does not comply with the "Five Principles of Similar Drugs", as a special category Carbohydrate Drugs or Therapeutic oligosaccharides It still has clear development value, especially in the field of injectable formulations. The safety background and clear multi-target pharmacological effects are important foundations for promoting its research and development.
Research status：
At present, there may not be abundant public and systematic research literature on the precise structure of oligosaccharides such as "mannuronic acid decaose", and its data (such as target information) is likely to come from preliminary screening by suppliers or internal research. This reflects that the compound is currently in Early stages of preclinical research However, the study of alginate oligosaccharides (AOS), especially fragments with different M/G ratios and polymerization degrees, has become an active direction in the field of marine drugs and functional sugars.
- basic research Numerous studies have confirmed that low molecular weight alginate oligosaccharides (especially fragments with a polymerization degree of 2-10) have activities in anti-inflammatory, antioxidant, regulating gut microbiota, enhancing immunity, anti-tumor, and promoting plant growth. Its function is closely related to the degree of polymerization, monosaccharide composition, and sequence.
- Mechanism Exploration The study has preliminarily linked the biological activity of AOS with signaling pathways such as TLR4, MAPK, NF - κ B, which is consistent with the target information provided in this article. The research on metabolic effects is gradually expanding, involving insulin signaling and lipid metabolism.
- Standardized substances Providing compounds with clear product codes such as BP4336 can help promote standardized research in this field and clarify the structure-activity relationships of specific structures (decasaccharides, full M sequences).
Application Prospects：
1. drug development：
- Metabolic disease treatment drugs As a multi target anti-inflammatory and metabolic regulator, it is developed as a new drug for injection for the treatment of type 2 diabetes, non-alcoholic fatty liver disease and metabolic syndrome. Its potential to improve insulin resistance and alleviate liver steatosis is worthy of further exploration.
- antiinflammatory drug Used to treat acute and chronic inflammatory diseases driven by excessive activation of the TLR4/NF - κ B pathway, such as sepsis, acute lung injury, arthritis, etc.
- adjuvant therapy Combining with existing hypoglycemic or lipid-lowering drugs may produce synergistic effects and improve treatment efficacy.
High end functional food/health products On the basis of proving its safety and effectiveness, it can be used as a functional food ingredient to regulate blood sugar, blood lipids, and enhance immunity. Although oral bioavailability is low, it may exert local effects in the intestine (such as regulating intestinal immunity, affecting microbiota), or still have a small amount absorbed to exert systemic effects.
Medical Aesthetics and Skin Care Based on its anti-inflammatory and moisturizing properties, it can be used to develop cosmetics or medical dressings that soothe skin inflammation and repair skin barriers.
Future research directions：
- In depth mechanism research Using techniques such as gene knockout and reporter genes, confirm the details of its direct interaction with targets such as TLR4 and downstream signaling networks in cell and animal models.
- Pharmacodynamic evaluation: In diabetes NAFLD、 In atherosclerosis and other animal models, the efficacy and dose effect relationship were systematically evaluated.
- Pharmacokinetic study Clarify its absorption, distribution, metabolism, and excretion characteristics under different administration routes, providing a basis for dosage form design.
- safety evaluation Complete preclinical toxicology studies of the system.
- structural optimization Explore the modification of its sugar chain (such as sulfation, acetylation) in order to enhance activity, stability, or improve pharmacokinetic properties.
Conclusion：
Mannuronic acid decaose represents a successful example of extracting oligosaccharides with specific biological activity from abundant marine biological resources. Through acting on TLR4, PPARG, NF - κ B and other key targets, it shows unique anti-inflammatory and metabolic regulation network pharmacological effects, and has attractive potential in addressing global chronic health challenges such as diabetes and cardiovascular disease. Despite facing challenges in terms of oral absorption in terms of drug properties, it is expected to develop into a new class of sugar based therapeutic drugs through strategies such as switching to injection administration. With the continuous deepening of sugar science and marine drug research, these structurally clear and functionally specific marine oligosaccharides are expected to occupy a place in the future pharmaceutical and health industries.
Batch can search by a CAS number,one per line
