 | |
| Names | |
|---|---|
| Other names PGH2, Endoperoxide H2, Prostaglandin R2 | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider |
|
| MeSH | Prostaglandin+H2 |
| UNII | |
| |
| |
| Properties | |
| C20H32O5 | |
| Molar mass | 352.465 g/mol |
| Density | 1.129 ± 0.06 g/mL |
| Boiling point | 490 ± 40.0 °C |
| 0.034 g/L | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Prostaglandin H2 (PGH2), orprostaglandin H2 (PGH2), is a type ofprostaglandin and a precursor for many other biologically significant molecules. It is synthesized fromarachidonic acid in a reaction catalyzed by acyclooxygenase enzyme.[2] The conversion fromarachidonic acid to prostaglandin H2 is a two-step process. First,COX-1 catalyzes the addition of two free oxygens to form the1,2-dioxane bridge and a peroxide functional group to formprostaglandin G2 (PGG2).[3] Second,COX-2 reduces the peroxide functional group to asecondary alcohol, forming prostaglandin H2. Other peroxidases likehydroquinone have been observed to reduce PGG2 to PGH2.[4] PGH2 is unstable at room temperature, with a half life of 90–100 seconds,[1] so it is often converted into a different prostaglandin. PGH2 is produced by every type of cell except for red blood cells and has a wide range of effects in the body.[5]
It is acted upon by:
It rearranges non-enzymatically to:
Functions of prostaglandin H2:
Effects ofaspirin on prostaglandin H2:
Prostaglandin H2 was discovered in 1973 by Diederik H. Nugteren and Elly Christ-Hazelhof while they were researching the formation of prostaglandin E2 from arachidonic acid using enzymes found invesicular glands.[9]
The original synthesis of prostaglandin H2 by Diederik H. Nugteren and Elly Christ-Hazelhof was performed in 1973.[9] Sheep vesicular glands were homogenized with 1MKH2PO4 and 0.001 MEDTA buffer and then centrifuged to isolate the COX-1 enzymes. Pure arachidonic acid was added to a solution containing the enzymes, and the mixture was shaken.Thin-layer chromatography was used to isolate a band of prostaglandin H2.
In 1986, due to low prostaglandin H2 product purity from thin-layer chromatography and columnchromatography,high-performance liquid chromatography withhexane andisopropanol as solvents was developed as an alternative means of isolating the prostaglandin with 98% purity.[10]
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