Levuglandin

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IUPACName=(5"Z",8"R",9"R",10"E",12"S")-9-acetyl-8-formyl-12- hydroxyheptadeca-5,10-dienoic acid
Name=Levuglandin D₂
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Section1= Chembox Identifiers
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PubChem=9548876
SMILES=CCCCCC(C=CC(C(CC=CCCCC(=O)O)C=O)C(=O)C)O
KEGG=C13808
Section2= Chembox Properties
Formula=C₂₀H₃₂O₅
MolarMass=352.465 g/mol
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ImageFile=Levuglandin E2.svg
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IUPACName=(5"Z",8"R",9"R",10"E",12"S")-8-acetyl-9-formyl-12- hydroxyheptadeca-5,10-dienoic acid
Name=Levuglandin E₂
OtherNames= LGE2
Section1= Chembox Identifiers
CASNo=
PubChem=5771742
SMILES=CCCCCC(C=CC(C=O)C(CC=CCCCC(=O)O)C(=O)C)O
KEGG=C13807
Section2= Chembox Properties
Formula=C₂₀H₃₂O₅
MolarMass=352.465 g/mol
Appearance=
Density=
MeltingPt=
BoilingPt=
Solubility=
Section3= Chembox Hazards
MainHazards=
FlashPt=
Autoignition=

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.cite journal |author=Salomon RG |title=Isolevuglandins, oxidatively truncated phospholipids, and atherosclerosis |journal=Ann. N. Y. Acad. Sci. |volume=1043 |issue= |pages=327–42 |year=2005 |pmid=16037255 |doi=10.1196/annals.1333.040 |url=http://www.annalsnyas.org/cgi/pmidlookup?view=long&pmid=16037255 |accessdate=2008-01-16] They are nonclassic eicosanoids. One species, levuglandin E₂, (LGE₂), forms neurotoxic adducts with
amyloid beta.cite journal
author= Bautaud "et al"
format=pdf
url= http://www.blackwell-synergy.com/doi/pdf/10.1111/j.1471-4159.2005.03586.x
journal= Biochemistry |volume=38|pages=9389–9396
title = PGH -derived levuglandin adducts increase the neurotoxicity of Amyloid Β_1–42
accessdate=2007-10-02
doi = 10.1021/bi990470+
year = 1999] 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 [M. Hamberg and B. Samuelsson, Detection and isolation of an endoperoxide intermediate in prostaglandin biosynthesis, Proc. Natl. Acad. Sci. U.S.A. 70 (1973), pp. 899–903.] [D.H. Nugteren and E. Hazelhof, Isolation and properties of intermediates in prostaglandin biosynthesis, Biochim. Biophys. Acta 326 (1973) (3), pp. 448–461.] . Prof. Robert Salomon at Case Western Reserve University discovered that a novel alternative rearrangement also occurs that producing two γ-ketoaldehydes [R.G. Salomon, D.B. Miller, M.G. Zagorski and D.J. Coughlin, 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 (1984) (20), pp. 6049–6060.] and named them levuglandins LGD2 and LGE2 as they are derivatives of levulinaldehyde with prostanoid side chains.

References