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Usage

Uses

Used in Pharmaceutical Industry:
CEREVISTEROL is used as a pharmaceutical compound for its potential therapeutic properties. Its unique structure and origin from endophytic fungi suggest that it may possess bioactive properties that can be harnessed for the development of new drugs or treatments.
Used in Research and Development:
CEREVISTEROL is used as a research compound for studying its chemical properties, biological activities, and potential applications in various fields. Its isolation from the fungus, Xylaria species, makes it an interesting subject for exploring the relationship between endophytic fungi and their host plants, as well as their potential role in producing bioactive compounds.
Used in Drug Discovery:
CEREVISTEROL is used as a starting material or a lead compound in drug discovery processes. Its unique ergostanoid structure and hydroxy group substitutions may provide a foundation for the development of new drugs with novel mechanisms of action, particularly in the areas of cancer treatment, inflammation, and other diseases where ergostanoids have shown potential.

InChI:InChI=1/C28H46O3/c1-17(2)18(3)7-8-19(4)22-9-10-23-21-15-25(30)28(31)16-20(29)11-14-27(28,6)24(21)12-13-26(22,23)5/h7-8,15,17-20,22-25,29-31H,9-14,16H2,1-6H3/b8-7+

Upstream product

• 481-23-2 (22E)-5α-hydroxyergosta-7,22-dien-6-on-3β-yl acetate 
• 96646-08-1 5,6β-dihydroxy-5α-ergosta-7,22-dien-3β-yl acetate 
• 57-87-4 Ergosterol 
• 23637-31-2 5α,6α-epoxy-24(R)-methylcholesta-7,22-dien-3β-ol 
• 7001-69-6 (22E,24R)-methylcholesta-6,22-diene-3β,5α,8α-triol 

Downstream Products

• 14858-07-2 3β,5α-dihydroxy-(22E,24R)-ergosta-7,22-dien-6-one 
• 38774-65-1 (22E,24R)-5-hydroxy-5α-ergosta-7,22-diene-3,6-dione 

Relevant academic research and scientific papers

Antioxidant and anti-osteoporotic activities of aromatic compounds and sterols from Hericium erinaceum

Hericium erinaceum, commonly called lion's mane mushroom, is a traditional edible mushroom widely used in culinary applications and herbal medicines in East Asian countries. In this study, a new sterol, cerevisterol 6-cinnamate (6), was isolated from the fruiting bodies of H. erinaceum together with five aromatic compounds 1-5 and five sterols 7-11. The chemical structures of these compounds were elucidated using chemical and physical methods and comparison of HRESIMS, 1D-NMR (1H, 13C, and DEPT) and 2D-NMR (COSY, HMQC, HMBC, and NOESY) spectra with previously reported data. The antioxidant and anti-osteoporotic activities of extracts and the isolated compounds 1-11 were investigated. All compounds exhibited peroxyl radical-scavenging capacity but only compounds 1, 3, and 4 showed potent reducing capacity. Moreover, compounds 1, 2, 4, and 5 showed moderate effects on cellular antioxidant activity and inhibited the receptor activator of nuclear factor κB ligand (RANKL)-induced osteoclastic differentiation. These results suggested that H. erinaceum could be utilized in the development of natural antioxidant and anti-osteoporotic nutraceuticals and functional foods.

Synthesis of the Alleged Structures of Fortisterol and Herbarulide and Structural Revision of Herbarulide

The alleged structures of 5,6-epoxy-5,6-secosteroids fortisterol and herbarulide differ only in the stereoconfiguration of C24. Applying insights into the hypothetical biosynthesis of this class of natural products, we devised a short synthetic access (four and eight steps, respectively) starting from commercial ergosterol and featuring an alkoxy radical rearrangement. The comparison of nuclear magnetic resonance spectroscopic data revealed herbarulide having the proposed structure of fortisterol, whereas synthesis of another two diastereomers could not conclusively prove the true structure of fortisterol. Along the way, a high-yielding and scalable access to the infamous Burawoy's ketone not requiring chromium(VI) reagents was developed.

Discoveries and Challenges en Route to Swinhoeisterol A

In this work, a full account of the authors’ synthetic studies is reported that culminated in the first synthesis of 13(14→8),14(8→7)diabeo-steroid swinhoeisterol A as well as the related dankasterones A and B, 13(14→8)abeo-steroids, and periconiastone A, a 13(14→8)abeo-4,14-cyclo-steroid. Experiments are described in detail that provided further insight into the mechanism of the switchable radical framework reconstruction approach. By discussing failed strategies and tactics towards swinhoeisterol A, the successful route that also allowed an access to structurally closely related analogues, such as Δ22-24-epi-swinhoeisterol A, is eventually presented.

METHODS AND COMPOSITIONS FOR THE TREATMENT OF ESTROGEN-DEPENDENT HYPERPROLIFERATIVE UTERINE DISORDERS

The present invention relates to the treatment of estrogen-dependent hyperproliferative uterine disorders including endometriosis, uterine fibroids, endometrial hyperplasia, uterine cancer, and their related symptoms by intravaginally administering at least two active agents selected from an aromatase inhibitor,an antiinflammatory agent, and a uterine-selective estrogen receptor antagonist. This combination therapy reduces local estrogen production, blocks local estrogen action, and suppresses inflammation locally, resulting in starvation of the estrogen-dependent diseased tissues, relief of related symptoms, and retardation of disease progression. Intravaginal delivery maximizes local inhibition of estrogen production without significantly affecting systemic circulating estogen levels. This results in enhanced clinical ellicacy and reduced side effects.

Synthesis and bioevaluation of Δ7-5-desaturase inhibitors, an enzyme late in the biosynthesis of the fungal sterol ergosterol

Ergosterol, the predominant sterol of fungi, is postulated to have many cellular functions which include a bulk membrane role and a regulatory role. Studies with sterol auxotrophs show that, even in the presence of sterols which can fulfill the bulk membrane requirements, a small concentration of ergosterol is absolutely necessary for growth. The Δ5-double bond appears to be required for the regulatory role of ergosterol; therefore, development of inhibitors of the enzyme that introduce this double bond, Δ7-sterol 5- desaturase (5-desaturase), may lead to effective antifungal agents. Within is the first reported synthesis of inhibitors of fungal 5-desaturase and the development of an in vitro tritium efficacy radioassay. The inhibitors were of the general structure 7,22(E)-ergostadien-3β-ol with α-face heteroatom substituents in the vicinity of C-5. They exhibited IC50 values of 47-149 μM.