Ergosterol

From DrugPedia: A Wikipedia for Drug discovery

Contents 1 Description 2 General Properties 3 PhysioChemical Properties 4 External Links 5 References

[edit] Description

Show 3-D Structure

A steroid of interest both because its biosynthesis in FUNGI is a target of ANTIFUNGAL AGENTS, notably AZOLES, and because when it is present in SKIN of animals, ULTRAVIOLET RAYS break a bond to result in ERGOCALCIFEROL. Ergosterol (ergosta-5,7,22-trien-3β-ol), a sterol, is a biological precursor (a provitamin) to Vitamin D₂. It is turned into viosterol by ultraviolet light, and is then converted into ergocalciferol, which is a form of Vitamin D.<ref>Rajakumar K, Greenspan SL, Thomas SB, Holick MF (October 2007). "SOLAR ultraviolet radiation and vitamin D: a historical perspective". Am J Public Health 97 (10): 1746–54. doi:10.2105/AJPH.2006.091736. PMID 17761571. </ref>

Ergosterol is a component of fungal cell membranes, serving the same function that cholesterol serves in animal cells. The presence of ergosterol in fungal cell membranes coupled with its absence in animal cell membranes makes it a useful target for antifungal drugs. Ergosterol is also present in the cell membranes of some protists, such as trypanosomes.<ref>Roberts CW, McLeod R, Rice DW, Ginger M, Chance ML, Goad LJ (February 2003). "Fatty acid and sterol metabolism: potential antimicrobial targets in apicomplexan and trypanosomatid parasitic protozoa". Mol. Biochem. Parasitol. 126 (2): 129–42. doi:10.1016/S0166-6851(02)00280-3. PMID 12615312. </ref> This is the basis for the use of some antifungals against West African sleeping sickness.

Amphotericin B is an antifungal drug that targets ergosterol. It binds to ergosterol and creates a polar pore in fungal membranes. This causes ions (predominantly K⁺ and H⁺) and other molecules to leak out, which will kill the cell.<ref>Ellis D (February 2002). "Amphotericin B: spectrum and resistance". J. Antimicrob. Chemother. 49 Suppl 1: 7–10. doi:10.1093/jac/49.suppl_1.7 (inactive 2008-07-02). PMID 11801575. </ref> Amphotericin B has been replaced by safer agents in most circumstances but is still used, despite its side effects, for life-threatening fungal or protozoa infections. Miconazole and Clotrimazole also inhibit synthesis of ergosterol.

Ergosterol is also used as an indicator of fungal biomass in soil. Though ergosterol does degrade over time, if kept below freezing in a dark environment, this degradation can be slowed or even stopped completely.

[edit] General Properties

*Molecular Weight

396.65

*Molecular Formula

C₂₈H₄₄O

*IUPAC NAME

(3S,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol

*Canonical Smiles

CC(C)C(C)C=CC(C)C1CCC2C1(CCC3C2=CC=C4C3(CCC(C4)O)C)C

*Isomeric Smiles

CC(C)[C@@H](C)C=C[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3C2=CC=C4[C@@]3(CC[C@@H](C4)O)C)C

[edit] PhysioChemical Properties

*Melting Point

*LogP

*Water Solubility

[edit] External Links

• [1]Pubchem
• [2]]1BXM,
• [3]KEGG Compound
• [4]Human Metabolome DataBase
• Safety (MSDS) data for ergosterol Oxford University (2005)

[edit] References

Template:Vitamin Template:Cholesterol metabolism intermediates Template:Phytosterols