2061-64-5

Usage

Uses

Used in Pharmaceutical Industry:
Ergosterol-5,8-peroxide is used as an active compound for the inhibition of Mpro, the primary protease of COVID-19. Network pharmacology and molecular docking studies have shown its potential to interfere with the replication process of the virus, making it a promising candidate for the development of antiviral treatments against COVID-19.
Used in Biotechnology Industry:
Ergosterol-5,8-peroxide can be utilized as a key component in the development of novel drug delivery systems and therapeutic applications. Its unique chemical properties allow for its integration into various biotechnological processes, potentially enhancing the efficacy and bioavailability of other pharmaceutical compounds.

InChI:InChI=1/C28H44O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26)15-16-28(23,24)31-30-27/h7-8,15-16,18-24,29H,9-14,17H2,1-6H3/b8-7+/t19-,20+,21-,22+,23+,24+,25+,26+,27+,28-/m0/s1

Upstream product

• 57-87-4 Ergosterol 
• 3957-39-9 isopyrocalcyferyl acetate 

Downstream Products

• 57-87-4 Ergosterol 
• 19254-69-4 ergosta-4,6,8(14),22-tetraen-3-one 
• 60045-90-1 3β-acetoxy-5α-ergosta-7,22t-dien-5-ol 

Relevant academic research and scientific papers

A new 5α,8α-epidioxy sterol from the Okinawan marine sponge of the Axinyssa genus

A new sterol (axinysterol) was isolated from the Okinawan marine sponge of the genus Axinyssa.The structure of axinysterol was assigned as 5α,8α-epidioxyergosta-6,22,25-trien-3β-ol based on spectroscopic analysis and chemical transformation. (Steroids 58: 410-413, 1993). Keywords: 5α,8α-epidioxyergosta-6,22,25-trien-3β-ol; axinysterol; marine sponge; Axinyssa genus; sterol; structure

Novel 26-oxygenated products in microbial degradation of ergosterol

In order to investigate the effect of the different stereochemistry of C- 24 on the microbial C-26 oxidation of sterol side-chain the genetically modified Mycobacterium sp. BCS 396 strain was used to transform ergosterol. Ergosterol was converted to 3-oxo-4,22-ergostadien-26-oic acid methyl ester, 3-oxo-1,4,22-ergostatrien-26-oic acid methyl ester, and 3-oxol-1,4,22- erogstatrien-26-oic acid, the structures of which have been determined by 1R, 1H NMR, 13C NMR, and mass spectroscopy. The X-ray structure of 3-oxo- 4,22-ergostadien-26-oic acid methyl ester revealed that oxidation at C-26 of the ergostane side-chain generates a chiral center with S-configuration at C- 25 as a result of chiral induction of the C-24 center.

Synthesis and biological evaluation of novel steroidal 5α,8α-endoperoxide derivatives with aliphatic side-chain as potential anticancer agents

By inspiration of significant anti-cancer activity of our previously screened natural ergosterol peroxide (EP), a series of novel steroidal 5α,8α-endoperoxide derivatives 5a–d and 14a–f were designed, synthesized, and biologically evaluated for their in vitro anti-proliferative inhibitory and cytotoxic activity. The results revealed that most of these compounds showed moderate-to-excellent anti-proliferative effects against the tested cancer cell lines (i.e. HepG2, SK-Hep1, MDA-MB-231 and MCF-7). Among them, compound 5b and 14d exhibited preferable inhibitory activities (IC50 of 5b and 14d are 8.07 and 9.50?μM against HepG2, respectively). The structure-activity relationships indicated that incorporation the peroxidic bridge to the steroid scaffolds at C-5 and C-8 positions together with the aliphatic side-chain at the C-17 position would provide synergistic effect for the bioactivity.

Antimycobacterial ergosterol-5,8-endoperoxide from Ajuga remota

In a bioassay-guided search for antimycobacterial natural products from higher plants, we have chemically investigated the methanol extract of aerial parts of Ajuga remota Benth. (Labiatae) for its active constituent(s). Bioactive chromatographic fractions of the crude extract provided the known triterpene ergosterol-5,8-endoperoxide plus the diterpenes clerodin, ajugarin-I, and ajugarin-II, which had been previously isolated from A. remota. This is the first report on the isolation of ergosterol-5,8- endoperoxide from this plant. The above compounds were tested in a radiorespirometric bioassay for activity against Mycobacterium tuberculosis. Ergosterol-5,8-endoperoxide showed a minimum inhibitory concentration (MIC) of 1 μg/ml. while ergosterol-5,8-endoperoxide acetate, ergosterol, and ergosta-5,7,9(11),22-tetraen-3β-ol gave MICs of 8 μg/ml, > 128 μg/ml, and 128 μg/ml. respectively. Clerodin, ajugarin-I, and ajugarin-II were inactive with MICs of > 128 μg/ml.

Development of ergosterol peroxide probes for cellular localisation studies

Ergosterol peroxide selectively exhibits biological activity against a wide range of diseases; however, its mode of action remains unknown. Here, we present an efficient synthesis of ergosterol peroxide chemical probes for in vitro anticancer evaluation,

Synthesis of 5α,8α-Ergosterol Peroxide 3-Carbamate Derivatives and a Fluorescent Mitochondria-Targeting Conjugate for Enhanced Anticancer Activities

Inspired by the significant anticancer activity of our previously screened natural ergosterol peroxide (1), we synthesized and characterized a series of novel ergosterol peroxide 3-carbamate derivatives. The antiproliferative activities of the synthesized

New biologically active marine sesquiterpenoid and steroid from the okinawan sponge of the genus Axinyssa

A new bisabolane-type sesquiterpenoid, (E)-3-isocyanobisabolane-7,10-diene (1), and a new epidioxyergostane-type steroid, 9(11)-dehydroaxinysterol (2), were isolated from the Okinawan sponge of the genus Axinyssa. Their structures were elucidated based on

Synthesis of ergosterol peroxide conjugates as mitochondria targeting probes for enhanced anticancer activity

Inspired by the significant bioactivity of ergosterol peroxide, we designed and synthesized four fluorescent coumarin and ergosterol peroxide conjugates 8a-d through the combination of ergosterol peroxide with 7-N,N-diethylamino coumarins fluorophore. The cytotoxicity of synthesized conjugates against three human cancer cells (HepG2, SK-Hep1, and MCF-7) was evaluated. The results of fluorescent imaging showed that the synthesized conjugates 8a-d localized and enriched mainly in mitochondria, leading to significantly enhanced cytotoxicity over ergosterol peroxide. Furthermore, the results of biological functions of 8d showed that it could suppress cell colony formation, invasion, and migration; induce G2/M phase arrest of HepG2 cells, and increase the intracellular ROS level.

Minor and Trace Sterols in Marine Invertebrates. 26. Isolation and Structure Elucidation of Nine New 5α,8α-Epidioxy Sterols from Four Marine Organisms

Sixteen 5α,8α-epidioxy Δ6 and Δ6,9(11) sterols, of which nine are new, have been isolated from the marine organisms Ascidia nigra, Dendrogyra cylindrus, Thalysias juniperina, and Aplysia dactylomela by reverse-phase high-performance liquid chromatography and characterized by high-resolution mass spectrometry and 360-MHz proton NMR spectroscopy.Attention is drawn to some unusual concentration-dependent NMR shifts of methyl signals.The probable biological significance of these epidioxy sterols is discussed with special reference to sterol biosynthesis.

New biologically active epidioxysterols from Stereum hirsutum

From the fungus Stereum hirsutum have been isolated and identified two new epidioxysterols 1, 4, together with two known ones 2 and 3. Their structures were elucidated on the basis of spectroscopic analysis and chemical reactions. Epidioxysterols 1-4 have been shown to possess a significant activity against Mycobacterium tuberculosis.