Levuglandin

Levuglandin E₂
Names
	IUPAC name (5Z,8R,9R,10E,12S)-8-acetyl-9-formyl-12- hydroxyheptadeca-5,10-dienoic acid
	Other names LGE2
Identifiers
CAS Number	91712-41-3;
3D model (JSmol)	Interactive image;
ChemSpider	4696839;
KEGG	C13807;
PubChem CID	5771742;
CompTox Dashboard (EPA)	DTXSID30429543 ;
	InChI InChI=1S/C20H32O5/c1-3-4-7-10-18(23)14-13-17(15-21)19(16(2)22)11-8-5-6-9-12-20(24)25/h5,8,13-15,17-19,23H,3-4,6-7,9-12H2,1-2H3,(H,24,25)/b8-5-,14-13+/t17-,18-,19-/m0/s1 Key: WJWAORNTZNRHBP-QNUMDXCLSA-N;
	SMILES CCCCC[C@@H](/C=C/[C@@H](C=O)[C@@H](C/C=C\CCCC(=O)O)C(=O)C)O;
Properties
Chemical formula	C20H32O5
Molar mass	352.465 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Levuglandin D₂
Names
	IUPAC name (5Z,8R,9R,10E,12S)-9-acetyl-8-formyl-12- hydroxyheptadeca-5,10-dienoic acid
Identifiers
CAS Number	91712-44-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	7827799 ;
KEGG	C13808 ;
PubChem CID	9548876;
CompTox Dashboard (EPA)	DTXSID30429543 ;
	InChI InChI=1S/C20H32O5/c1-3-4-7-11-18(23)13-14-19(16(2)22)17(15-21)10-8-5-6-9-12-20(24)25/h5,8,13-15,17-19,23H,3-4,6-7,9-12H2,1-2H3,(H,24,25)/b8-5-,14-13+/t17-,18-,19-/m0/s1 Key: MLLWPVVMXGUOHD-QNUMDXCLSA-N ;
	SMILES CCCCC[C@@H](/C=C/[C@H]([C@@H](C/C=C\CCCC(=O)O)C=O)C(=O)C)O;
Properties
Chemical formula	C20H32O5
Molar mass	352.465 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

Levuglandins are reactive aldehydes formed by the spontaneous rearrangement of prostaglandin H (PGH). Enantiomerically pure levuglandin (LG) E₂ can also be formed through the cyclooxygenase (COX) pathway by a rearrangement of the prostaglandin (PG) endoperoxide PGH ₂.[1] They are nonclassic eicosanoids. One species, levuglandin E₂, (LGE₂), forms neurotoxic adducts with amyloid beta.[2] Levuglandins and isolevuglandins can damage proteins by covalent adduction, thereby interfering with their normal functions. These lipid-derived protein modifications may serve as dosimeters of oxidative injury. Elevated plasma levels of isoLG-protein epitopes are associated with atherosclerosis but are independent of total cholesterol, a classical risk factor.

History

Though spontaneous rearrangements of PGH2 are known to generate prostaglandins (PG) PGD2 and PGE2.[3][4] Prof. Robert Salomon at Case Western Reserve University discovered that a novel alternative rearrangement also occurs that producing two γ-ketoaldehydes[5] and named them levuglandins LGD2 and LGE2 as they are derivatives of levulinaldehyde with prostanoid side chains.

References

Salomon RG (2005). "Isolevuglandins, oxidatively truncated phospholipids, and atherosclerosis". Ann. N. Y. Acad. Sci. 1043: 327–42. Bibcode:2005NYASA1043..327S. doi:10.1196/annals.1333.040. PMID 16037255. Retrieved 2008-01-16.
Bautaud; Brame, CJ; Salomon, RG; Roberts Lj, 2nd; Oates, JA; et al. (1999). "PGH -derived levuglandin adducts increase the neurotoxicity of Amyloid Β_1–42" (pdf). Biochemistry. 38 (29): 9389–9396. doi:10.1021/bi990470+. PMID 10413514. Retrieved 2007-10-02.
Hamberg M., Samuelsson B. (1973). "Detection and isolation of an endoperoxide intermediate in prostaglandin biosynthesis". Proc. Natl. Acad. Sci. U.S.A. 70 (3): 899–903. Bibcode:1973PNAS...70..899H. doi:10.1073/pnas.70.3.899. PMC 433384. PMID 4514999.
Nugteren D.H., Hazelhof E. (1973). "Isolation and properties of intermediates in prostaglandin biosynthesis". Biochim. Biophys. Acta. 326 (3): 448–461. doi:10.1016/0005-2760(73)90145-8. PMID 4776443.
Salomon R.G.; Miller D.B.; Zagorski M.G.; Coughlin D.J. (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". J. Am. Chem. Soc. 106 (20): 6049–6060. doi:10.1021/ja00332a049.

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[pmid16037255-1] Salomon RG (2005). "Isolevuglandins, oxidatively truncated phospholipids, and atherosclerosis". Ann. N. Y. Acad. Sci. 1043: 327–42. Bibcode:2005NYASA1043..327S. doi:10.1196/annals.1333.040. PMID 16037255. Retrieved 2008-01-16.

[boutand-2] Bautaud; Brame, CJ; Salomon, RG; Roberts Lj, 2nd; Oates, JA; et al. (1999). "PGH -derived levuglandin adducts increase the neurotoxicity of Amyloid Β_1–42" (pdf). Biochemistry. 38 (29): 9389–9396. doi:10.1021/bi990470+. PMID 10413514. Retrieved 2007-10-02.

[3] Hamberg M., Samuelsson B. (1973). "Detection and isolation of an endoperoxide intermediate in prostaglandin biosynthesis". Proc. Natl. Acad. Sci. U.S.A. 70 (3): 899–903. Bibcode:1973PNAS...70..899H. doi:10.1073/pnas.70.3.899. PMC 433384. PMID 4514999.

[4] Nugteren D.H., Hazelhof E. (1973). "Isolation and properties of intermediates in prostaglandin biosynthesis". Biochim. Biophys. Acta. 326 (3): 448–461. doi:10.1016/0005-2760(73)90145-8. PMID 4776443.

[5] Salomon R.G.; Miller D.B.; Zagorski M.G.; Coughlin D.J. (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". J. Am. Chem. Soc. 106 (20): 6049–6060. doi:10.1021/ja00332a049.