Ergosterol
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IUPAC name
(22E)-Ergosta-5,7,22-trien-3β-ol
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Systematic IUPAC name
(1R,3aR,7S,9aR,9bS,11aR)-1-[(2R,3E,5R)-5,6-Dimethylhept-3-en-2-yl]-7-hydroxy-9a,11a-dimethyl-2,3,3a,6,7,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[a]phenanthren-7-ol | |
Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.000.320 |
EC Number |
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MeSH | Ergosterol |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C28H44O | |
Molar mass | 396.65 g/mol |
Melting point | 160 °C (320 °F; 433 K) |
Boiling point | 250 °C (482 °F; 523 K) |
-279.6·10−6 cm3/mol | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ergosterol (ergosta-5,7,22-trien-3β-ol) is a mycosterol found in cell membranes of fungi and protozoa, serving many of the same functions that cholesterol serves in animal cells. Because many fungi and protozoa cannot survive without ergosterol, the enzymes that synthesize it have become important targets for drug discovery. In human nutrition, ergosterol is a provitamin form of vitamin D2; exposure to ultraviolet (UV) light causes a chemical reaction that produces vitamin D2.
Role in fungi
Ergosterol (ergosta-5,7,22-trien-3β-ol) is a sterol found in fungi, and named after
Target for antifungal drugs
Because ergosterol is present in cell membranes of fungi, yet absent in those of animals, it is a useful target for antifungal drugs. Ergosterol is also present in the cell membranes of some protists, such as trypanosomes.[4] This is the basis for the use of some antifungals against West African sleeping sickness.
Amphotericin B, an antifungal drug, targets ergosterol. It binds physically to ergosterol within the membrane, thus creating a polar pore in fungal membranes. This causes ions (predominantly potassium and hydrons) and other molecules to leak out, which will kill the cell.[5] Amphotericin B has been replaced by safer agents in most circumstances, but is still used, despite its side effects, for life-threatening fungal or protozoan infections.
Fluconazole, miconazole, itraconazole, clotrimazole, and myclobutanil work in a different way, inhibiting synthesis of ergosterol from lanosterol by interfering with 14α-demethylase.[6] Ergosterol is a smaller molecule than lanosterol; it is synthesized by combining two molecules of farnesyl pyrophosphate, a 15-carbon-long terpenoid, into lanosterol, which has 30 carbons. Then, two methyl groups are removed, making ergosterol. The "azole" class of antifungal agents inhibit the enzyme that performs these demethylation steps in the biosynthetic pathway between lanosterol and ergosterol.[6]
Target for antiprotozoal drugs
Some protozoa, including Trichomonas and Leishmania are inhibited by drugs that target ergosterol synthesis and function[7]
As a vitamin D2 precursor
Ergosterol is a
This happens naturally to a certain extent, and many mushrooms are irradiated after harvest to increase their vitamin D content. Fungi are also grown industrially so that ergosterol can be extracted and converted to Vitamin D for sale as a dietary supplement and food additive.[10]
Preparations of irradiated ergosterol containing a mixture of previtamin and vitamin D2 were called viosterol in the 1930s.[11]
Toxicity
Ergosterol powder is an irritant to skin, eyes, and the respiratory tract. Ingestion of large amounts can cause
See also
- Mushrooms and vitamin D
References
- PMID 20526375.
- PMID 22946816.
- PMID 34202105.
- PMID 12615312.
- PMID 11801575.
- ^ PMID 27221657.
- S2CID 24585556.
- PMID 19281276.
- ^ Haytowitz, DB. "Vitamin D in mushrooms" (PDF). US Department of Agriculture. Archived (PDF) from the original on 2013-05-12. Retrieved 2014-08-23.
- ^ ISBN 978-0123819789.
- .
- ^ "Material Safety Data Sheet for Ergosterol". Fisher Scientific. Archived from the original on 2016-03-03. Retrieved 2009-06-16.