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Ergosterol
View on Wikipediafrom Wikipedia
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| Names | |
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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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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 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
[edit]Ergosterol (ergosta-5,7,22-trien-3β-ol) is a sterol found in fungi, and named after ergot, the common name of members of the fungal genus Claviceps from which ergosterol was first isolated. Ergosterol is a component of yeast and other fungal cell membranes, serving many of the same functions that cholesterol serves in animal cells.[1] Its specificity in higher fungi is thought to be related to the climatic instabilities (highly varying humidity and moisture conditions) encountered by these organisms in their typical ecological niches (plant and animal surfaces, soil). Thus, despite the added energy requirements of ergosterol synthesis (if compared to cholesterol), ergosterol is thought to have evolved as a nearly ubiquitous, evolutionarily advantageous fungal alternative to cholesterol.[2] This advantage could be linked to the presence of two conjugated double bonds in the structure (B-ring) of ergosterol giving it antioxidant properties.[3] Additionally, the structure of ergosterol appears to have been finely tuned towards optimal interaction with saturated lipids.[4]
Biosynthesis
[edit]The immediate precursor of ergosterol in yeasts is ergosta-5,7,22,24(28)-tetraen-3β-ol. One of its double bonds is reduced by the enzyme Δ24(241)-sterol reductase, which uses nicotinamide adenine dinucleotide phosphate (NADPH) as its cofactor.[5]
-tetraen-3%CE%B2-ol.svg)
As a vitamin D2 precursor
[edit]Ergosterol is a biological precursor of vitamin D2, the chemical name of which is ergocalciferol. Exposure of white button mushrooms to UV-C irradiation produces time-dependent increases in vitamin D2 concentrations in the mushrooms.[6][7] Fungi are grown industrially to enable ergosterol extraction and preparation as a powder for sale as a vitamin D2 dietary supplement and food additive.[8]
Preparations of irradiated ergosterol containing a mixture of previtamin and vitamin D2 were called viosterol in the 1930s.[9]
Target for antifungal drugs
[edit]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.[10] 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 protons) and other molecules to leak out, which will kill the cell.[11] 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.[12] 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.[12]
Target for antiprotozoal drugs
[edit]Some protozoa, including Trichomonas and Leishmania are inhibited by drugs that target ergosterol synthesis and function[13]
Safety
[edit]Ergosterol powder is a mechanical irritant to skin, eyes, and the respiratory tract. Ingestion may cause gastrointestinal irritation with vomiting, nausea, and diarrhea.[14]
Toxicity
[edit]Ergosterol itself has no vitamin D activity and does not cause poisioning via this mechanism. Ergosterol added to rat food at 1% dry weight did not cause toxic effects.[15] Ergosterol is not classifiable under GHS[16] or REACH.[17]
The safety data sheets for ergostrol commonly confuse it with ergocalciferol (vitamin D2),[a] which due to having vitamin D activity is hazadarous in relatively small amounts, being able to cause hypercalcemia via Vitamin D toxicity. Historical cases of poisoning are attributed to irradiated ergosterol, which contains vitamin D2 in addition to ergosterol. These do not constitute evidence for ergosterol toxicity.[20]
Metabolism
[edit]Ergosterol is converted to brassicasterol in the mammalian liver by DHCR7, the enzyme responsible for producing 7-dehydrocholesterol (provitamin D3) from cholestrol. Here the enzyme catalyzes an reaction analogous to the reverse of provitamin D3 production.[15]
Ergosterol added to a high-fat, high-sugar (HFHS) rat diet at a very high concentration of 1% increases the blood levels of vitamin D2 by about 4 ng/mL, suggesting that ergosterol that enters the mammalian skin is converted to D2 when exposed to light.[15] This same treatment approximately quartered the serum levels of D3 and halfed the serum levels of 25-OH D3.[15] At this dose ergosterol has a significant effect on sterol metabolism. It fully normalizes blood markers related to bile acid metabolism to control levels compared to the group only fed the HFHS diet. It displayed significant (but insufficient to match control) normalization of LDL-C and TBA levels.[15]
See also
[edit]References
[edit]- ^ The SDS that correctly identify this issue are already cited before. The MSDS for ergosterol from Fisher Scientific includes a misleading but correct note that "Ingestion of large amounts of vitamin D may result in . [...] Prolonged hypercalcemia may result in a deposition of calcium salts in the soft tissues, most significantly the kidney." but it does not make the claim of ergosterol having a vitamin D activity at any point.[14] The MSDS from Cayman Chem reports an unreasonably low oral LD50 of 10 mg/kg, which is not possible giving the rat feeding stufy quoted.[18] More reputable sources such as Sigma-Alderich generally report the oral LD50 of ergocalciferol at 10 mg/kg, which is strongly suggestive of confusion.[19]
- ^ Weete JD, Abril M, Blackwell M (May 2010). "Phylogenetic distribution of fungal sterols". PLOS ONE. 5 (5) e10899. Bibcode:2010PLoSO...510899W. doi:10.1371/journal.pone.0010899. PMC 2878339. PMID 20526375.
- ^ Dupont S, Lemetais G, Ferreira T, Cayot P, Gervais P, Beney L (September 2012). "Ergosterol biosynthesis: a fungal pathway for life on land?". Evolution; International Journal of Organic Evolution. 66 (9): 2961–2968. doi:10.1111/j.1558-5646.2012.01667.x. PMID 22946816.
- ^ Dupont S, Fleurat-Lessard P, Cruz RG, Lafarge C, Grangeteau C, Yahou F, Gerbeau-Pissot P, Abrahão Júnior O, Gervais P, Simon-Plas F, Cayot P, Beney L (June 2021). "Antioxidant Properties of Ergosterol and Its Role in Yeast Resistance to Oxidation". Antioxidants. 10 (7): 1024. doi:10.3390/antiox10071024. PMC 8300696. PMID 34202105.
- ^ Juarez-Contreras, Israel; Lopes, Laura J. S.; Holt, Jamie; Yu-Liao, Lorena; O'Shea, Katherine; Ruiz-Ruiz, Jose; Sodt, Alexander; Budin, Itay (2025-04-23). "Structural dissection of ergosterol metabolism reveals a pathway optimized for membrane phase separation". Science Advances. 11 (17) eadu7190. Bibcode:2025SciA...11.7190J. doi:10.1126/sciadv.adu7190. PMC 12017304. PMID 40267201.
- ^ Zweytick D, Hrastnik C, Kohlwein SD, Daum G (2000). "Biochemical characterization and subcellular localization of the sterol C-24(28) reductase, erg4p, from the yeast saccharomyces cerevisiae". FEBS Lett. 470 (1): 83–7. Bibcode:2000FEBSL.470...83Z. doi:10.1016/S0014-5793(00)01290-4. PMID 10722850.
- ^ Koyyalamudi SR, Jeong SC, Song CH, Cho KY, Pang G (April 2009). "Vitamin D2 formation and bioavailability from Agaricus bisporus button mushrooms treated with ultraviolet irradiation". Journal of Agricultural and Food Chemistry. 57 (8): 3351–3355. Bibcode:2009JAFC...57.3351K. doi:10.1021/jf803908q. 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.
- ^ Hirsch AL (12 May 2011). "Chapter 6: Industrial Aspects of Vitamin D". In Feldman D, Pike JW, Adam JS (eds.). Vitamin D: Two-Volume Set. Academic Press. ISBN 978-0-12-381978-9.
- ^ Science Service (1930). "Viosterol official name for irradiated ergosterol". Journal of Chemical Education. 7 (1): 166. Bibcode:1930JChEd...7..166S. doi:10.1021/ed007p166.
- ^ 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". Molecular and Biochemical Parasitology. 126 (2): 129–142. doi:10.1016/S0166-6851(02)00280-3. PMID 12615312.
- ^ Ellis D (February 2002). "Amphotericin B: spectrum and resistance". The Journal of Antimicrobial Chemotherapy. 49 (Suppl 1): 7–10. doi:10.1093/jac/49.suppl_1.7. PMID 11801575.
- ^ a b Lv QZ, Yan L, Jiang YY (August 2016). "The synthesis, regulation, and functions of sterols in Candida albicans: Well-known but still lots to learn". Virulence. 7 (6): 649–659. doi:10.1080/21505594.2016.1188236. PMC 4991322. PMID 27221657.
- ^ Carrillo-Muñoz AJ, Tur-Tur C, Giusiano G, Marcos-Arias C, Eraso E, Jauregizar N, Quindós G (April 2013). "Sertaconazole: an antifungal agent for the topical treatment of superficial candidiasis". Expert Review of Anti-Infective Therapy. 11 (4): 347–358. doi:10.1586/eri.13.17. hdl:11336/8943. PMID 23566144. S2CID 24585556.
- ^ a b "Material Safety Data Sheet for Ergosterol". Fisher Scientific. Archived from the original on 2016-03-03. Retrieved 2009-06-16.
- ^ a b c d e Kuwabara, Naoko; Sato, Shinji; Nakagawa, Saori (1 December 2023). "Effects of Long-Term High-Ergosterol Intake on the Cholesterol and Vitamin D Biosynthetic Pathways of Rats Fed a High-Fat and High-Sucrose Diet". Biological and Pharmaceutical Bulletin. 46 (12): 1683–1691. doi:10.1248/bpb.b23-00348.
- ^ "Ergosterol, Safety data sheet acc. to Regulation (EC) No. 1907/2006 (REACH)" (PDF). Carl Roth/Astech. 2022-08-19. Retrieved 28 January 2026.
- ^ Sigma-Aldrich (October 2022). "Ergosterol, according to Regulation (EC) No. 1907/2006, Version 6.3".
- ^ Cayman Chemical (July 2023). "Ergosterol, Safety Data Sheet acc. to OSHA HCS" (PDF).
- ^ Sigma-Aldrich (December 2025). "Ergocalciferol, according to Regulation (EC) No. 1907/2006, as amended by Commission Regulation (EU) 2020/878, Version 7.1".
- ^ Tumulty, Philip A.; Howard, John Eager (16 May 1942). "IRRADIATED ERGOSTEROL POISONING: REPORT OF TWO CASES". Journal of the American Medical Association. 119 (3): 233. doi:10.1001/jama.1942.02830200001001.
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Ergosterol
View on Grokipediafrom Grokipedia
Ergosterol is a sterol lipid with the molecular formula C28H44O, consisting of an ergostane skeleton featuring double bonds at the 5-6, 7-8, and 22-23 positions, along with a 3β-hydroxy group, and it serves as the primary sterol in the cell membranes of fungi.[1] Unlike cholesterol, which predominates in animal cells, ergosterol is unique to fungi and certain protists, where it constitutes approximately 30–40% of the plasma membrane lipids in species like yeast.[2]
In fungal cells, ergosterol plays a crucial role in maintaining membrane fluidity, permeability, and structural integrity, enabling essential processes such as nutrient transport and signal transduction.[3] It forms lipid rafts that facilitate protein localization and membrane organization, and its levels are tightly regulated through biosynthetic pathways involving enzymes like lanosterol 14α-demethylase.[4] Additionally, upon exposure to ultraviolet (UV) light, particularly UV-B, ergosterol is converted into ergocalciferol (vitamin D2), making fungi and mushrooms a natural dietary source of this provitamin in humans.[5]
Ergosterol's fungal specificity has made its biosynthesis a prime target for antifungal therapies, with drugs such as azoles (e.g., fluconazole) inhibiting key enzymes in the pathway to disrupt membrane function and induce fungal cell death.[6] Polyenes like amphotericin B bind directly to ergosterol, forming pores that compromise membrane integrity, while allylamines block earlier steps in sterol production.[7] This therapeutic strategy is vital for treating systemic infections, though emerging resistance highlights the need for novel inhibitors targeting ergosterol-related processes.[8]