Prostaglandin H2
Page Template:Chembox/styles.css has no content.
Template:Chembox IndexlistTemplate:Chembox CompToxTemplate:Chembox Datapage check| Lua error in package.lua at line 80: module 'Module:InfoboxImage/data' not found. | |
| Names | |
|---|---|
| Other names
PGH2, Endoperoxide H2, Prostaglandin R2
| |
| Identifiers | |
| Page Template:Plainlist/styles.css has no content. | |
3D model (JSmol)
|
Page Template:Plainlist/styles.css has no content. |
| ChEBI | Page Template:Plainlist/styles.css has no content. |
| ChemSpider | Page Template:Plainlist/styles.css has no content. |
| EC Number | Page Template:Plainlist/styles.css has no content. |
| Page Template:Plainlist/styles.css has no content. | |
| MeSH | Prostaglandin+H2 |
PubChem CID
|
Page Template:Plainlist/styles.css has no content. |
| RTECS number | Page Template:Plainlist/styles.css has no content. |
| UNII | Page Template:Plainlist/styles.css has no content. |
| |
| |
| 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 their standard state (at 25 °C [77 °F], 100 kPa).
| |
Template:Chembox Footer/trackingTemplate:Short description
Prostaglandin H2 (PGH2), or prostaglandin H2 (PGH2), is a type of prostaglandin and a precursor for many other biologically significant molecules. It is synthesized from arachidonic acid in a reaction catalyzed by a cyclooxygenase enzyme.[2] The conversion from arachidonic acid to prostaglandin H2 is a two-step process. First, COX-1 catalyzes the addition of two free oxygens to form the 1,2-dioxane bridge and a peroxide functional group to form prostaglandin G2 (PGG2).[3] Second, COX-2 reduces the peroxide functional group to a secondary alcohol, forming prostaglandin H2. Other peroxidases like hydroquinone 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:
- prostacyclin synthase to create prostacyclin
- thromboxane-A synthase to create thromboxane A2 and 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid (HHT) (see 12-Hydroxyheptadecatrienoic acid)
- prostaglandin D2 synthase to create prostaglandin D2
- prostaglandin E synthase to create prostaglandin E2
- prostaglandin F synthase to create prostaglandin F2α[6]
It rearranges non-enzymatically to:
- A mixture of 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid (HHT) and 12-(S)-hydroxy-5Z,8Z,10E-heptadecatrienoic acid (see 12-hydroxyheptadecatrienoic acid)
- These breakdown products are associated with increased aggregation of Amyloid beta peptides and Alzheimer's disease.[7]
Functions of prostaglandin H2:
- regulating the constriction and dilation of blood vessels
- stimulating platelet aggregation
- binds to thromboxane receptor on platelets' cell membranes to trigger platelet migration and adhesion to other platelets[8]
Effects of aspirin on prostaglandin H2:
- Aspirin has been hypothesized to block the conversion of arachidonic acid to prostaglandin
History
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 in vesicular glands.[9]
Synthesis
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 1M KH2PO4 and 0.001 M EDTA 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 column chromatography, high-performance liquid chromatography with hexane and isopropanol as solvents was developed as an alternative means of isolating the prostaglandin with 98% purity.[10]
References
Page Template:Reflist/styles.css has no content.
- ^ a b Template:Cite HMDB
- ^ Page Module:Citation/CS1/styles.css has no content.van der Donk WA, Tsai AL, Kulmacz RJ (December 2002). "The cyclooxygenase reaction mechanism". Biochemistry. 41 (52): 15451–8. doi:10.1021/bi026938h. PMID 12501173.
- ^ Page Module:Citation/CS1/styles.css has no content.Salomon RG, Miller DB, Zagorski MG, Coughlin DJ (October 1984). "Prostaglandin endoperoxides. 14. Solvent-induced fragmentation of prostaglandin endoperoxides. New aldehyde products from PGH2 and a novel intramolecular 1,2-hydride shift during endoperoxide fragmentation in aqueous solution". Journal of the American Chemical Society. 106 (20): 6049–6060. doi:10.1021/ja00332a049. ISSN 0002-7863.
- ^ Page Module:Citation/CS1/styles.css has no content.Hla T, Neilson K (August 1992). "Human cyclooxygenase-2 cDNA". Proceedings of the National Academy of Sciences of the United States of America. 89 (16): 7384–8. Bibcode:1992PNAS...89.7384H. doi:10.1073/pnas.89.16.7384. PMC 49714. PMID 1380156.
- ^ Page Module:Citation/CS1/styles.css has no content.Miller, Stephen B. (2006-08-01). "Prostaglandins in Health and Disease: An Overview". Seminars in Arthritis and Rheumatism. 36 (1): 37–49. doi:10.1016/j.semarthrit.2006.03.005. ISSN 0049-0172.
- ^ Page Module:Citation/CS1/styles.css has no content.Hirata, Takako; Narumiya, Shuh (2011-08-05). "Prostanoid Receptors". ACS Publications. doi:10.1021/cr200010h. Retrieved 2025-11-16.
- ^ Page Module:Citation/CS1/styles.css has no content.Boutaud, Olivier; Ou, Joyce J.; Chaurand, Pierre; Caprioli, Richard M.; Montine, Thomas J.; Oates, John A. (2002). "Prostaglandin H2 (PGH2) accelerates formation of amyloid β1−42 oligomers". Journal of Neurochemistry. 82 (4): 1003–1006. doi:10.1046/j.1471-4159.2002.01064.x. ISSN 1471-4159.
- ^ Page Module:Citation/CS1/styles.css has no content.Woodward DF, Jones RL, Narumiya S (September 2011). "International Union of Basic and Clinical Pharmacology. LXXXIII: classification of prostanoid receptors, updating 15 years of progress". Pharmacological Reviews. 63 (3): 471–538. doi:10.1124/pr.110.003517. PMID 21752876.
- ^ a b Page Module:Citation/CS1/styles.css has no content.Nugteren, D. H.; Hazelhof, E. (1973-12-20). "Isolation and properties of intermediates in prostaglandin biosynthesis". Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism. 326 (3): 448–461. doi:10.1016/0005-2760(73)90145-8. ISSN 0005-2760.
- ^ Page Module:Citation/CS1/styles.css has no content.Zulak, I. M.; Puttemans, M. L.; Schilling, A. B.; Hall, E. R.; Venton, D. L. (1986-04-01). "A fast, nondestructive purification scheme for prostaglandin H2 using a nonaqueous, bonded-phase high-performance liquid chromatography system". Analytical Biochemistry. 154 (1): 152–161. doi:10.1016/0003-2697(86)90509-9. ISSN 0003-2697.
Lua error in package.lua at line 80: module 'Module:Navbox/configuration' not found. Lua error in package.lua at line 80: module 'Module:Navbox/configuration' not found.
