Перекись эргостерола

Description

Ergosterol peroxide (5α,8α-epidioxyergosta-6,22-dien-3β-ol) is an oxysterol, a product of photochemical oxidation of ergosterol with singlet oxygen, which accumulates in the fruiting bodies of edible and medicinal mushrooms, including chaga (Inonotus obliquus). An extremely extensive list of synonyms reflects the long history of studying the substance under different names: ergosterol endoperoxide, peroxyergosterol, ergosterol 5α,8α-epidioxide, etc.; NSC number 31324; additional CAS numbers of related formulations - 22321-17-1, 49759-24-2, 64907-19-3 and others.

Basic Attributes

• CAS No.: 2061-64-5
• Chemical formula: C28H44O3
• Molecular weight: 428.6
• Exact weight: 428.65
• PSA specification: 38.69
• XLogP3: 7.68

Physico-chemical characteristics

• Density: 1.1±0.1 g/cm3
• Melting point: 178 °C
• Boiling point: 499.7±45.0 °C

Chemical class and biological activity

Ergosterol peroxide belongs to oxysterols - derivatives of ergosterol with a characteristic endoperoxide bridge between the C5 and C8 atoms of the steroid core. It is recognized as the main antitumor sterol of a number of edible and medicinal mushrooms and is responsible for the anti-inflammatory, antitumor and antiviral effects of mushroom extracts. The anti-inflammatory mechanism is associated with the suppression of NF-κB and C/EBPβ activity and MAPK phosphorylation, which reduces TNF-α secretion and IL-1α/β expression in macrophages; Chaga extract has additionally been described to suppress the NF-κB/iNOS-COX-2 pathway. Antitumor effects have been demonstrated against colorectal cancer, hepatocellular carcinoma, prostate cancer, myeloma and leukemia through mechanisms of suppression of β-catenin signaling, induction of apoptosis and antiangiogenic effects on the JAK2/STAT3 pathway; in the concentration range of 10–60 μM, inhibition of AKT and c-Myc with activation of Foxo3-mediated death of human hepatocellular carcinoma cells was shown.

Scope of application

The substance is used as an object for pharmacological studies of the antitumor and anti-inflammatory properties of mushroom extracts, as well as a reference standard for the quantitative determination of oxysterols in raw materials of edible and medicinal mushrooms (shiitake, chaga, oyster mushroom and other species) by HPLC and LC-MS. The compound is also described as a fermentation product of the fungus Paecilomyces cicadae, expanding the range of biotechnological sources of the compound beyond the traditional fruiting bodies of basidiomycetes.

Storage and handling

Store in an airtight container, in a cool, dry place, protected from light - the endoperoxide bridge of the molecule is thermally and photochemically unstable and can decompose when heated or long-term storage in the light. Work using standard personal protective equipment for laboratory assistants - gloves, safety glasses, avoiding contact with reducing agents, taking into account the proven biological activity of the substance and its peroxide functional group.