Ergosterol

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Ergosterol

IUPAC name	(3S,9S,10R,13R,14R,17R)-17-((2R,5R,E)-5,6- dimethylhept-3-en-2-yl)-10,13- dimethyl-2,3,4,9,10,11,12,13,14,15,16,17- dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Identifiers
CAS number	57-87-4
MeSH	Ergosterol
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
Properties
Molecular formula	C₂₈H₄₄O
Molar mass	396.66 g/mol
Melting point	160.0 °C
Boiling point	250.0 °C
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 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causes ions (predominantly K⁺ and H⁺) and other molecules to leak out, which will kill the cell.^[3] Amphotericin B has been replaced by safer agents in most circumstances but is still used, despite its side effects, for life-threatening fungal infections.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.

[edit] References

^ 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.
^ 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.
^ 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 2 July 2008). PMID 11801575, http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=11801575.

[edit] External links

Safety (MSDS) data for ergosterol Oxford University (2005)

This biochemistry article is a stub. You can help Wikipedia by expanding it.

v • d • e Vitamins (A11)

Fat soluble	A: Retinol - Beta-carotene - Tretinoin - Alpha-carotene D3: 7-Dehydrocholesterol → Previtamin D3 → Cholecalciferol (D3) → Calcidiol → Calcitriol (active form) → Calcitroic acid D2: Ergosterol → Ergocalciferol (D2) D analogues: Dihydrotachysterol - Calcipotriol - Tacalcitol D4: Dihydroergocalciferol E: Tocopherol - Tocotrienol K: Naphthoquinone - Phylloquinone/K1 - Menatetrenone/K2

Water soluble: B vitamins	B₁ (Thiamine) - B₂ (Riboflavin) - B₃ (Niacin, Nicotinamide) - B₅ (Pantothenic acid, Dexpanthenol, Pantethine) - B₆ (Pyridoxine, Pyridoxal phosphate, Pyridoxamine) - B₇ (Biotin) - B₉ (Folic acid, Folinic acid) - B₁₂ (Cyanocobalamin, Hydroxocobalamin, Methylcobalamin, Cobamamide)

Water soluble: other	C (Ascorbic acid) - Choline

see also enzyme cofactors

v • d • e Cholesterol metabolic intermediates

to HMG-CoA	Acetyl-CoA - Acetoacetyl-CoA - HMG-CoA

to Dimethylallyl pyrophosphate	Mevalonic acid - Phosphomevalonic acid - 5-Diphosphomevalonic acid - Isopentenyl pyrophosphate - Dimethylallyl pyrophosphate

Geranyl-	Geranyl pyrophosphate - Geranylgeranyl pyrophosphate

To Cholesterol	Farnesyl pyrophosphate - Squalene - 2,3-Oxidosqualene - Lanosterol - (to Ergosterol in fungi)

see also enzymes

v • d • e Phytosterols

Beta-sitosterol • Campesterol • Stigmasterol • Brassicasterol • Delta-7-stigmasterol • Delta-7-avenasterol • Ergosterol (Vitamin D2)

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