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Ergosterol
File:Ergosterol
Identifiers
CAS number 57-87-4 Y
PubChem 444679
ChemSpider 392539
UNII Z30RAY509F Y
EC number 200-352-7
MeSH Ergosterol
SMILES
InChI
InChI key
Properties
Molecular formula C28H44O
Molar mass 396.65 g/mol
Exact mass 396.339216
Melting point

160.0 °C

Boiling point

250.0 °C

 Y (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. Because ergosterol is present in fungal cell membranes yet absent in animal cell membranes, it is 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(predominantly potassium and protons) and other molecules to leak out, which will kill the cell.[3] Amphotericin B has been replaced by safer agents in most circumstances but is still used, despite its side-effects, for life-threatening fungal or protozoan infections.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 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 anti-fungal agents inhibit the enzyme that performs these demethylation steps in the biosynthetic pathway 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, in particular, the kidneys.[6]

See also

Mushrooms and vitamin D

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. PMC 1994178. 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). [Expression error: Unexpected < operator "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). [Expression error: Unexpected < operator "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 (11): 1298–1302. PMID 11085355. 
  5. ^ Takaku, T; Kimura, Y; Okuda, H (2001). [Expression error: Unexpected < operator "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

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Wiktionary

Up to date as of January 15, 2010

Definition from Wiktionary, a free dictionary

Contents

English

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Wikipedia

Noun

Singular
ergosterol

Plural
countable and uncountable; plural ergosterols

ergosterol (countable and uncountable; plural ergosterols)

  1. (biochemistry, steroids, mycology) The steroid precursor of vitamin D2. It is found in cell membranes of fungi, and is their functional equivalent of cholesterol. It is also found in the membranes of some protists.

Translations

Related terms

See also

  • viosterol

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