Ergosterol


Ergosterol

Chembox new
ImageFile = Ergosterol structure.svg
ImageSize = 250px
IUPACName = (3"S",9"S",10"R",13"R",14"R",17"R")-17-((2"R",5"R","E")-5,6-
dimethylhept-3-en-2-yl)-10,13-
dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-
dodecahydro-1"H"-cyclopenta ["a"] phenanthren-3-ol
OtherNames =
Section1 = Chembox Identifiers
CASNo = 57-87-4
PubChem =
SMILES = CC(C) [C@@H] (C)C=C [C@@H]
(C) [C@H] 1CC [C@H] 2C3=C
C=C4C [C@@H] (O)CC [C@] 4
(C) [C@H] 3CC [C@] 12C
InChI=1/C28H44O/c1-18(2) 19(3)7-8-20(4)24-11-12- 25-23-10-9-21-17-22(29) 13-15-27(21,5)26(23)14- 16-28(24,25)6/h7-10, 18-20,22,24-26,29H,11- 17H2,1-6H3/b8-7+/t19-, 20+,22-,24+,25-,26-, 27-,28+/m0/s1
MeSHName = Ergosterol

Section2 = Chembox Properties
Formula = C28H44O
MolarMass = 396.66 g/mol
Appearance =
Density =
MeltingPt = 160.0 °C
BoilingPt = 250.0 °C

Section3 = Chembox Hazards
Solubility =
MainHazards =
FlashPt =
Autoignition =

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. [cite journal |author=Rajakumar K, Greenspan SL, Thomas SB, Holick MF |title=SOLAR ultraviolet radiation and vitamin D: a historical perspective |journal=Am J Public Health |volume=97 |issue=10 |pages=1746–54 |year=2007 |month=October |pmid=17761571 |doi=10.2105/AJPH.2006.091736 |url=http://www.ajph.org/cgi/pmidlookup?view=long&pmid=17761571]

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. [cite journal |author=Roberts CW, McLeod R, Rice DW, Ginger M, Chance ML, Goad LJ |title=Fatty acid and sterol metabolism: potential antimicrobial targets in apicomplexan and trypanosomatid parasitic protozoa |journal=Mol. Biochem. Parasitol. |volume=126 |issue=2 |pages=129–42 |year=2003 |month=February |pmid=12615312 |doi=10.1016/S0166-6851(02)00280-3] 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. [cite journal |author=Ellis D |title=Amphotericin B: spectrum and resistance |journal=J. Antimicrob. Chemother. |volume=49 Suppl 1 |issue= |pages=7–10 |year=2002 |month=February |pmid=11801575 |url=http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=11801575 |doi=10.1093/jac/49.suppl_1.7 |doi_brokendate=2008-07-02] Amphotericin B has been replaced by safer agents in most circumstances but is still used, despite its side effects, for life-threatening fungal 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.

References

External links

[http://ptcl.chem.ox.ac.uk/MSDS/ER/ergosterol.html Safety (MSDS) data for ergosterol] Oxford University (2005)


Wikimedia Foundation. 2010.

Look at other dictionaries:

  • Ergosterol — Ergostérol Ergostérol Molécule d ergostérol Général No CAS …   Wikipédia en Français

  • Ergostérol — Molécule d ergostérol Général No CAS …   Wikipédia en Français

  • ergosterol — ERGOSTERÓL, ergosteroli, s.m. Substanţă prezentă în diverse ţesuturi animale şi vegetale, a cărei activare, prin iradiere cu raze ultraviolete, produce vitamina D2; ergosterină. – Din fr. ergostérol. Trimis de LauraGellner, 13.09.2007. Sursa: DEX …   Dicționar Român

  • ergostérol — [ ɛrgosterɔl ] n. m. • 1933; de ergot (de seigle) et stérol, d apr. ergostérine (fin XIXe) ♦ Biochim. Alcool stérolique préparé autrefois à partir de l ergot (II, 1o) et aujourd hui de la levure, qui se transforme en vitamine D antirachitique… …   Encyclopédie Universelle

  • ergosterol — n. a plant sterol that is converted into vitamin D by ultraviolet radiation. [WordNet 1.5] …   The Collaborative International Dictionary of English

  • ergosterol — Esterol insaturado del grupo de la vitamina D aislado de las levaduras, champiñones, cornezuelo de centeno y otros hongos. Cuando se trata con radiación ultravioleta se convierte en vitamina D2. Diccionario Mosby Medicina, Enfermería y Ciencias… …   Diccionario médico

  • ergosterol — ergostèrōl m <G ergosteróla> DEFINICIJA kem. C28H44O, kristalni spoj sterolske strukture koji djelovanjem ultravioletnog zračenja prelazi u vitamin D; ima ga u kvascu, u biljnim i životinjskim mastima ETIMOLOGIJA v. ergot + v. sterol …   Hrvatski jezični portal

  • ergosterol — [ʉr gäs′tər ôl΄, ʉr gäs′tərōl΄] n. [< ERGOT + STEROL] a crystalline plant sterol, C28H43OH, formerly prepared from ergot but now chiefly from yeast: when exposed to ultraviolet rays it produces a vitamin (D2) used to prevent or cure rickets …   English World dictionary

  • ergosterol — /err gos teuh rohl , rawl/, n. Biochem. a colorless, crystalline, water insoluble sterol, C28H43OH, that occurs in ergot and yeast and that, when irradiated with ultraviolet light, is converted to vitamin D. [1885 90; ERGO 2 + STEROL] * * * ▪… …   Universalium

  • Ergosterol — Strukturformel Allgemeines Freiname Ergosterin Andere …   Deutsch Wikipedia