Ergosterol Powder CAS 57-87-4

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Ergosterol powder, also known as ergosterol, CAS 57-87-4, Molecular formula C28H44O, is a white or colorless bright lobular crystal or white crystalline powder. Soluble in ethanol, ether, benzene and chloroform, insoluble in water. Dissolve ergosterol in solvents such as chloroform, ether or cyclohexane, add it to the flask of quartz glass, and prepare vitamin D by ultraviolet irradiation. Ergosterol not only has unique physiological effects, but also is widely used in the development of drugs. Ergosterol, as an important component of fungal cell membrane, has stable structure and strong specificity. For the determination of biomass, it is more representative than glucosamine, so the fungal biomass can be measured by detecting the content of ergosterol. Ergosterol is mainly synthesized by microbial fermentation. In recent years, scholars have also extracted it from some mycelium.

At home and abroad, ergosterol is mainly produced by microbial fermentation. The main strains producing ergosterol in large quantities are yeast and Aspergillus. The type of strain affects the final ergosterol yield. There are many screening methods for high-yield strains, the most common of which are natural breeding, mutation breeding, protoplast fusion and genetic engineering.

Ergosterol powder biosynthesis:

Yeast, as the simplest eukaryote, although the sterol end products synthesized are different from other higher eukaryotes, its basic metabolic pathway is similar, and the related genes have high homology, which can realize the functional exchange. Therefore, yeast, especially Saccharomyces cerevisiae, is an ideal model system to study the sterol biosynthesis pathway and its regulation. The biosynthesis of sterols is very complex. Taking ergosterol as an example, it involves at least 23 reactions and requires the participation of 25 enzymes; At the same time, it is also a highly energy consuming biological process. Each molecule of ergosterol needs to consume at least 24 ATP and 16 NADPH molecules. The synthesis of all eukaryotic sterols starts from acetyl coenzyme A (acetyl CoA). In yeast, the biosynthesis pathway from acetyl CoA to ergosterol can be divided into three stages, which occur in different positions in the cell.

Among the above reactions, some are the speed limiting steps of ergosterol synthesis pathway. The effect of the improvement of the reaction activity of these steps on ergosterol synthesis in cells may be related to its position in the metabolic pathway. ERG11 gene encodes sterol C-14 demethylase. The high expression of this gene has no obvious effect on the content of ergosterol in cells, but the content of intermediates such as yeast sterol and episterol has increased. The sterol C-24 methyltransferase encoded by ERG6 gene catalyzes the methylation of yeast sterols to produce fecal sterols. The overexpression of this gene increases the contents of fecal sterols, episterols and ergosterol in yeast cells; However, the overexpression of erg2 gene encoding sterol C-8 isomerase inhibited ergosterol synthesis. Erg5 encoded sterol C-22 desaturase activity increased, resulting in a decrease in ergosterol content in cells, but intermediate sterol components such as yeast sterol, lanosterol, and episterol increased. Erg4 encoded sterol C-24 (28) reductase catalyzes the last step of ergosterol synthesis pathway. Overexpression of this gene can significantly increase ergosterol content in cells.

Ergosterol powder, also known as ergosterol, is an important component of fungal cell membranes and has broad application value in the field of biology.

Maintenance of cellular physiological functions

 

(1) Ensuring the integrity of cell membrane structure
As a key component of fungal cell membranes, stable membrane structures are formed by embedding phospholipid bilayers. The rigid cyclic structure and hydrophobic tail in its molecular structure interact with the fatty acid chains of phospholipid molecules, enhancing the mechanical strength of the membrane. In fungi such as yeast and mold, this substance accounts for 30% -50% of the total lipids in the cell membrane. This high proportion distribution ensures the stability of the cell membrane under environmental stress such as osmotic pressure changes and mechanical pressure.
(2) Membrane permeability regulation
By adjusting the fluidity of the membrane, it affects the efficiency of substance transmembrane transport. The changes in its content directly affect the conformation and activity of membrane proteins, for example, in the process of nutrient absorption, it can regulate the conformational changes of glucose transporters and promote the transmembrane transport of glucose. Experimental data shows that when its content decreases by 20%, the absorption rate of glucose by brewing yeast decreases by 35%.

 

(3) Maintenance of membrane-bound enzyme activity
As an anchor site for membrane-bound enzymes, the enzyme maintains its active conformation through steric hindrance and electrostatic interactions. For example, in respiratory chain complex IV, ergosterol binds to subunits of cytochrome c oxidase to ensure the continuity of the electron transport chain. Research has found that in mutant strains lacking ergosterol, the activity of respiratory chain complex IV decreases by 60%, and the efficiency of ATP synthesis decreases by 45%.
(4) Cellular material transport
Participate in vesicle transport and phagocytosis processes. In the yeast secretion pathway, ergosterol promotes the formation and transport of secretory vesicles by regulating the curvature of the Golgi apparatus membrane. Fluorescence labeling experiments showed that the number of secretory vesicles in ergosterol synthesis deficient strains decreased by 40%, and the transport speed decreased by 50%.

Drug development and application

 

(1) Antifungal drug targets
It is an important target of antifungal drugs. Polyene antibiotics (such as amphotericin B) bind with ergosterol to form transmembrane pores, leading to the leakage of cellular contents; Azole antifungal drugs (such as ketoconazole) inhibit the key enzyme lanosterol 14 α - demethylase (CYP51) in the ergosterol synthesis pathway, blocking ergosterol synthesis. Clinical data shows that the MIC value of amphotericin B against Candida can reach 0.1-0.5 μ g/mL, while the MIC value of azole drugs against Aspergillus is in the range of 0.5-2 μ g/mL.

(2) Raw materials for vitamin D2 production
After irradiation with ultraviolet light (280-320nm), its B ring undergoes cleavage to produce vitamin D2 (ergocalciferol). This process involves photolysis and isomerization reactions, and the conversion rate of the final product vitamin D2 can reach 60% -70%.

 

In the field of medicine, vitamin D2 is used to prevent and treat rickets and osteoporosis, with a recommended daily dose of 400-800IU.

(3) Hormonal drug intermediates
It is an important precursor for the synthesis of steroid hormones. It can be converted into hormone drugs such as progesterone and hydrocortisone through chemical modification. Taking progesterone synthesis as an example, ergosterol undergoes 17 enzymatic reactions, among which the key steps include breaking the C20-C22 bond and hydroxylation at the C17 position. These hormone drugs have wide applications in fields such as reproductive regulation and anti-inflammatory treatment.

Application of biomarkers

 

(1) Fungal biomass detection
The content of ergosterol is significantly positively correlated with fungal biomass (R ²=0.98). The fungal biomass can be calculated by measuring the ergosterol content in the sample using high-performance liquid chromatography (HPLC). This method has high sensitivity (detection limit of 0.1 μ g/g) and good reproducibility (RSD<5%), and has been widely used in fields such as food microbiological detection and environmental fungal contamination assessment.

(2) Fungal classification and identification
There are significant differences in ergosterol content among different fungal genera and species. For example, yeast has a ergosterol content of 2-5mg/g dry weight, while Aspergillus can reach 8-12mg/g dry weight. By combining gas chromatography-mass spectrometry (GC-MS) technology to analyze the structural differences of ergosterol side chains, precise identification of fungal genera and species can be achieved.

 

(3) Disease diagnostic indicators
Abnormal metabolism of ergosterol is associated with various diseases. In the serum of patients with fungal infections, the content of ergosterol derivatives is significantly increased (3-5 times higher than that of healthy individuals), which can be used as early diagnostic markers for invasive fungal infections. In addition, the levels of ergosterol oxidation products (such as 24,25-dihydroergosterol) are correlated with oxidative stress status and can be used to evaluate the degree of cell damage.

Agriculture and Biological Control

 

(1) Plant growth regulation
Exogenous addition of ergosterol can promote plant growth and development. In wheat seed treatment experiments, soaking seeds in a 0.1mg/L ergosterol solution can increase germination rate by 15% and seedling height by 20%. Its mechanism of action includes regulating endogenous hormone balance, enhancing photosynthetic efficiency, etc.

(2) Biological pesticide development
Inhibitors of ergosterol synthesis, such as tebuconazole and tebuconazole, exert bactericidal effects by inhibiting fungal ergosterol synthesis. This type of fungicide has significant control effects on fungal diseases such as powdery mildew and rust. Field trials have shown that the control effect can reach 80% -90%, and the toxicity to non target organisms is low.

(3) Microbial fertilizer enhances efficiency
Adding ergosterol powder can improve the stability of bacterial fertilizer formulations. Adding 0.5% ergosterol to rhizobium preparations can increase bacterial survival rate by 30% and nitrogen fixation efficiency by 25%. Its mechanism of action includes protecting cell membrane integrity and enhancing environmental adaptability.

Nutrition and Health Promotion

 

(1) Antioxidant effect
Ergosterol has the ability to scavenge free radicals. In vitro experiments have shown that ergosterol has an IC50 value of 12 μ g/mL for DPPH radicals and a clearance rate of 75% for hydroxyl radicals (at a concentration of 50 μ g/mL). Its antioxidant mechanism includes direct quenching of free radicals, chelation of metal ions, etc.

(2) Immune regulation
Ergosterol can enhance the body's immune function. Animal experiments have shown that feeding mice with a diet containing 0.05% ergosterol increases macrophage phagocytic index by 40% and lymphocyte proliferation rate by 35%. Its mechanism of action involves activating the TLR4 signaling pathway and promoting cytokine secretion.

(3) Cardiovascular protection
It has the function of regulating blood lipids. Clinical studies have found that daily supplementation of 200mg ergosterol can reduce LDL-C levels by 15% and increase HDL-C levels by 10%. Its lipid-lowering mechanism includes inhibiting cholesterol absorption and promoting bile acid excretion.

Ergosterol (ergosterol, chemical formula C ₂₈ H ₄₄ O) is a key component of fungal and protozoan cell membranes. Its structure is similar to cholesterol in animal cells, and it plays a role in maintaining membrane fluidity and stability. Due to the high dependence of fungi on the synthesis of Ergosterol, its synthases (such as lanosterol 14 α - demethylase) have become important targets for antifungal drugs (such as azoles and amphotericin B). In addition, Ergostelol can be converted into vitamin D ₂ under ultraviolet irradiation, and is therefore also used as a food nutrition enhancer.

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