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{{chembox
{{chembox
| Verifiedfields = changed
|ImageFile=Levuglandin D2.svg
| Watchedfields = changed
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|ImageSize=
| verifiedrevid = 367263100
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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 D<sub>2</sub>
| ImageFile=Levuglandin D2.svg
⚫
| ImageSize=
⚫
|OtherNames=
⚫
| IUPACName=(5''Z'',8''R'',9''R'',10''E'',12''S'')-9-acetyl-8-formyl-12- hydroxyheptadeca-5,10-dienoic acid
⚫
|Section1= {{Chembox Identifiers
| Name=Levuglandin D<sub>2</sub>
⚫
| CASNo=91712-44-6
⚫
| OtherNames=
⚫
| PubChem=9548876
⚫
|Section1={{Chembox Identifiers
⚫
| SMILES=CCCCCC(C=CC(C(CC=CCCCC(=O)O)C=O)C(=O)C)O
| CASNo_Ref = {{cascite|correct|??}}
⚫
| KEGG=C13808
⚫
| CASNo=91712-44-6
⚫
| PubChem=9548876
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 7827799
⚫
| SMILES = CCCCC[C@@H](/C=C/[C@H]([C@@H](C/C=C\CCCC(=O)O)C=O)C(=O)C)O
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = MLLWPVVMXGUOHD-QNUMDXCLSA-N

| KEGG_Ref = {{keggcite|correct|kegg}}
⚫
| KEGG=C13808
}}
}}
|Section2= {{Chembox Properties
|Section2={{Chembox Properties
| Formula=C<sub>20</sub>H<sub>32</sub>O<sub>5</sub>
| Formula=C<sub>20</sub>H<sub>32</sub>O<sub>5</sub>
| MolarMass=352.465 g/mol
| MolarMass=352.465 g/mol
| Appearance=
| Appearance=
| Density=
| Density=
| MeltingPt=
| MeltingPt=
| BoilingPt=
| BoilingPt=
| Solubility=
| Solubility=
}}
}}
|Section3= {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards=
| MainHazards=
| FlashPt=
| FlashPt=
| AutoignitionPt =
| Autoignition=
}}
}}
}}
}}
{{chembox
{{chembox
|ImageFile=Levuglandin E2.svg
| ImageFile=Levuglandin E2.svg
|ImageSize=
| ImageSize=
|IUPACName=(5''Z'',8''R'',9''R'',10''E'',12''S'')-8-acetyl-9-formyl-12- hydroxyheptadeca-5,10-dienoic acid
| IUPACName=(5''Z'',8''R'',9''R'',10''E'',12''S'')-8-acetyl-9-formyl-12- hydroxyheptadeca-5,10-dienoic acid
|Name=Levuglandin E<sub>2</sub>
| Name=Levuglandin E<sub>2</sub>
|OtherNames= LGE2
| OtherNames= LGE2
|Section1= {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo=91712-41-3
| CASNo=91712-41-3
| PubChem=5771742
| PubChem=5771742
| ChemSpiderID = 4696839
| SMILES=CCCCCC(C=CC(C=O)C(CC=CCCCC(=O)O)C(=O)C)O
| SMILES = CCCCC[C@@H](/C=C/[C@@H](C=O)[C@@H](C/C=C\CCCC(=O)O)C(=O)C)O
⚫
| KEGG=C13807
| StdInChI = 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
| StdInChIKey = WJWAORNTZNRHBP-QNUMDXCLSA-N
⚫
| KEGG=C13807
}}
}}
|Section2= {{Chembox Properties
|Section2={{Chembox Properties
| Formula=C<sub>20</sub>H<sub>32</sub>O<sub>5</sub>
| Formula=C<sub>20</sub>H<sub>32</sub>O<sub>5</sub>
| MolarMass=352.465 g/mol
| MolarMass=352.465 g/mol
| Appearance=
| Appearance=
| Density=
| Density=
| MeltingPt=
| MeltingPt=
| BoilingPt=
| BoilingPt=
| Solubility=
| Solubility=
}}
}}
|Section3= {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards=
| MainHazards=
| FlashPt=
| FlashPt=
| AutoignitionPt =
| Autoignition=
}}
}}
}}
}}
'''Levuglandins''' are reactive [[aldehyde]]s formed by the spontaneous rearrangement of [[Prostaglandin|prostaglandin H]] (PGH). Enantiomerically pure levuglandin (LG) E<sub>2</sub> can also be formed through the cyclooxygenase (COX) pathway by a rearrangement of the prostaglandin (PG) endoperoxide PGH <sub>2</sub>.<ref name="pmid16037255">{{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}}</ref> They are [[nonclassic eicosanoid]]s. One species, levuglandin E<sub>2</sub>, (LGE<sub>2</sub>), forms neurotoxic [[adduct]]s with
'''Levuglandins''' are reactive [[aldehyde]]s formed by the spontaneous rearrangement of [[Prostaglandin|prostaglandin H]] (PGH). Enantiomerically pure levuglandin (LG) E<sub>2</sub> can also be formed through the cyclooxygenase (COX) pathway by a rearrangement of the prostaglandin (PG) endoperoxide PGH <sub>2</sub>.<ref name="pmid16037255">{{cite journal |author=Salomon RG |title=Isolevuglandins, oxidatively truncated phospholipids, and atherosclerosis |journal=Ann. N. Y. Acad. Sci. |volume=1043 |pages=327–42 |year=2005 |issue=1 |pmid=16037255 |doi=10.1196/annals.1333.040|bibcode=2005NYASA1043..327S |s2cid=12782911 }}</ref> They are [[nonclassic eicosanoid]]s. One species, levuglandin E<sub>2</sub>, (LGE<sub>2</sub>), forms neurotoxic [[adduct]]s with
[[amyloid beta]].<ref name=boutand>{{cite journal
[[amyloid beta]].<ref>{{cite journal
|doi = 10.1111/j.1471-4159.2005.03586.x|title = PGH2-derived levuglandin adducts increase the neurotoxicity of amyloid beta1-42|year = 2006|last1 = Boutaud|first1 = Olivier|last2 = Montine|first2 = Thomas J.|last3 = Chang|first3 = Lei|last4 = Klein|first4 = William L.|last5 = Oates|first5 = John A.|journal = Journal of Neurochemistry|volume = 96|issue = 4|pages = 917–923|pmid = 16412101|pmc = 1621054}}</ref><ref>{{cite journal|doi=10.1021/bi990470+|pmid=10413514|year=1999|last1=Boutaud|first1=O.|last2=Brame|first2=C. J.|last3=Salomon|first3=R. G.|last4=Roberts Lj|first4=2nd|last5=Oates|first5=J. A.|title=Characterization of the lysyl adducts formed from prostaglandin H2 via the levuglandin pathway|journal=Biochemistry|volume=38|issue=29|pages=9389–96}}</ref>
|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 &Beta;<sub>1&ndash;42</sub>
|accessdate=2007-10-02
|doi = 10.1021/bi990470
|year = 1999
|pmid= 10413514
|last2= Brame
|first2= CJ
|last3= Salomon
|first3= RG
|last4= Roberts Lj
|first4= 2nd
|last5= Oates
|first5= JA
|issue= 29}}</ref>
Levuglandins and isolevuglandins can damage proteins by covalent adduction, thereby interfering with their normal functions.
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.
These lipid-derived protein modifications may serve as dosimeters of oxidative injury.
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==History==
==History==
Though spontaneous rearrangements of PGH2 are known to generate prostaglandins (PG) PGD2 and PGE2.<ref>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.</ref><ref>D.H. Nugteren and E. Hazelhof, Isolation and properties of intermediates in prostaglandin biosynthesis, Biochim. Biophys. Acta 326 (1973) (3), pp. 448–461.</ref> Prof. Robert Salomon at Case Western Reserve University discovered that a novel alternative rearrangement also occurs that producing two γ-ketoaldehydes<ref>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.</ref> and named them levuglandins LGD2 and LGE2 as they are derivatives of levulinaldehyde with prostanoid side chains.
Though spontaneous rearrangements of PGH2 are known to generate prostaglandins (PG) PGD2 and PGE2.<ref>{{cite journal | author = Hamberg M., Samuelsson B. | year = 1973 | title = Detection and isolation of an endoperoxide intermediate in prostaglandin biosynthesis | journal = Proc. Natl. Acad. Sci. U.S.A. | volume = 70 | issue = 3| pages = 899–903 | doi=10.1073/pnas.70.3.899| pmc = 433384 | pmid=4514999| bibcode = 1973PNAS...70..899H | doi-access = free }}</ref><ref>{{cite journal | author = Nugteren D.H., Hazelhof E. | year = 1973 | title = Isolation and properties of intermediates in prostaglandin biosynthesis | journal = Biochim. Biophys. Acta | volume = 326 | issue = 3| pages = 448–461 | doi=10.1016/0005-2760(73)90145-8| pmid = 4776443 }}</ref> Prof. Robert Salomon at Case Western Reserve University discovered that a novel alternative rearrangement also occurs that producing two γ-ketoaldehydes<ref>{{cite journal |author1=Salomon R.G. |author2=Miller D.B. |author3=Zagorski M.G. |author4=Coughlin D.J. | year = 1984 | title = 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 = J. Am. Chem. Soc. | volume = 106 | issue = 20| pages = 6049–6060 | doi=10.1021/ja00332a049}}</ref> and named them levuglandins LGD2 and LGE2 as they are derivatives of levulinaldehyde with prostanoid side chains.


==References==
==References==
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