Levuglandin

Chemical compound From Wikipedia, the free encyclopedia

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][3] 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.

Quick facts Names, Identifiers ...
Levuglandin D2
Names
IUPAC name
(5Z,8R,9R,10E,12S)-9-acetyl-8-formyl-12- hydroxyheptadeca-5,10-dienoic acid
Identifiers
3D model (JSmol)
ChemSpider
KEGG
  • 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 ☒N
    Key: MLLWPVVMXGUOHD-QNUMDXCLSA-N ☒N
  • CCCCC[C@@H](/C=C/[C@H]([C@@H](C/C=C\CCCC(=O)O)C=O)C(=O)C)O
Properties
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).
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Quick facts Names, Identifiers ...
Levuglandin E2
Names
IUPAC name
(5Z,8R,9R,10E,12S)-8-acetyl-9-formyl-12- hydroxyheptadeca-5,10-dienoic acid
Other names
LGE2
Identifiers
3D model (JSmol)
ChemSpider
KEGG
  • 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
  • CCCCC[C@@H](/C=C/[C@@H](C=O)[C@@H](C/C=C\CCCC(=O)O)C(=O)C)O
Properties
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).
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History

Though spontaneous rearrangements of PGH2 are known to generate prostaglandins (PG) PGD2 and PGE2.[4][5] Prof. Robert Salomon at Case Western Reserve University discovered that a novel alternative rearrangement also occurs that producing two γ-ketoaldehydes[6] and named them levuglandins LGD2 and LGE2 as they are derivatives of levulinaldehyde with prostanoid side chains.

References

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