The Full Wiki

More info on Ergosterol

Ergosterol: Wikis

Advertisements
  

Note: Many of our articles have direct quotes from sources you can cite, within the Wikipedia article! This article doesn't yet, but we're working on it! See more info or our list of citable articles.

Encyclopedia

From Wikipedia, the free encyclopedia

Ergosterol
Identifiers
CAS number 57-87-4 Yes check.svgY
PubChem 4835
EC number 200-352-7
MeSH Ergosterol
SMILES
InChI
Properties
Molecular formula C28H44O
Molar mass 396.65 g/mol
Exact mass 396.339216
Melting point

160.0 °C

Boiling point

250.0 °C

 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.[1]

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.[2] 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 physically to ergosterol within the membrane , and thus creates a polar pore in fungal membranes. This causes ions (predominantly potassium and protons) and other molecules to leak out, which will kill the cell.[3] Amphotericin B has been replaced by safer agents in most circumstances but is still used, despite its side effects, for life-threatening fungal or protozoa infections.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, Itraconazole, and Clotrimazole work in a different way, inhibiting synthesis of ergosterol from lanosterol. Ergosterol is a smaller molecule than lanosterol; it is synthesized by combining two molecules of farnisyl pyrophosphate, a 15 carbon long protein into lanosterol which has 30 carbons. Then two carbon groups are clipped off, making ergosterol. The " azoles" inhibit one of the enzymes which removes a methyl from lanosterol, one of the steps between lanosterol and 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.

Research has shown ergosterol may have anti-tumor properties.[4][5]

Ergosterol powder is an irritant to skin, eyes, and the respiratory tract. Ingestion of large amounts can cause hypercalcemia, which (if prolonged) can lead to calcium salt deposits in the soft tissues, and particularly the kidneys.[6]

References

  1. ^ 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. http://www.ajph.org/cgi/pmidlookup?view=long&pmid=17761571. 
  2. ^ 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. 
  3. ^ 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. http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=11801575. 
  4. ^ Yazawa Y, Yokota M, Sugiyama K. (2000). "Antitumor promoting effect of an active component of Polyporus, ergosterol and related compounds on rat urinary bladder carcinogenesis in a short-term test with concanavalin A.". Biol Pharm Bull 11: 1298–1302. PMID 11085355. 
  5. ^ Takaku, T; Kimura; Okuda (2001). "Isolation of an antitumor compound from Agaricus blazei Murill and its mechanism of action.". The Journal of nutrition 131 (5): 1409–13. PMID 11340091. 
  6. ^ Material Safety Data Sheet, Fisher Scientific

External links

Advertisements

Advertisements






Got something to say? Make a comment.
Your name
Your email address
Message