Oxidation products of arachidonic acid II. The synthesis of methyl 8R,9S,11R-trihydroxy-5Z,12E,14Z-eicosatrienoate

1980 ◽  
Vol 58 (17) ◽  
pp. 1799-1805 ◽  
Author(s):  
George Just ◽  
Corinne Luthe
Keyword(s):  
Arachidonic Acid ◽  
Total Synthesis ◽  
Title Compound ◽  
Oxidation Products ◽  
Important Intermediate

A stereospecific total synthesis of the title compound, 37, starting from diacetone glucose (9), is described. Key intermediates in the synthesis are 3-deoxy-5,6-anhydro-1,2-O-isopropylidene-glucofuranose (15), obtained in 55% yield from 9, and methyl 8-tert-butyldiphenylsilyl-9,11-O-isopropylidene-8R,9S,11R-trihydroxy-12-oxo-dodeca-5Z-enoate (33), an important intermediate in the synthesis of other oxidation products of arachidonic acid.

Ozone toxicity: Hormone-like oxidation products from arachidonic acid by ozone-catalyzed autoxidation

1977 ◽  
Vol 1 (2) ◽  
pp. 75-82 ◽  
Author(s):  
J.H Roycroft ◽  
W.B Gunter ◽  
D.B Menzel
Keyword(s):  
Arachidonic Acid ◽  
Oxidation Products ◽  
Ozone Toxicity

Synthesis of 14-hydroxy steroids. Total synthesis of methyl 14β-hydroxy-1,7,17-trioxo-5β,8-androstene-10β-oate and related compounds

1990 ◽  
Vol 68 (11) ◽  
pp. 1917-1922 ◽  
Author(s):  
Réjean Ruel ◽  
Pierre Deslongchamps
Keyword(s):  
Total Synthesis ◽  
Ammonium Salt ◽  
Michael Addition ◽  
Title Compound ◽  
Steroid Synthesis ◽  
Related Compounds ◽  
Acetylenic Ketone

The total synthesis of the title compound 22 and methyl 14α-hydroxy-5β,13α,8-androstene-1,7,17-trioxo-10β-oate 21 isomer is reported. We also describe the 1,6-Michael addition of 2-methyl-1,3-cyclopentanedione on dienone 14 and the protic ammonium salt catalyzed intramolecular Michael addition of cyclic β-ketoester on the conjugated acetylenic ketone 13. Keywords: cardenolides, steroid synthesis, aldol, Michael addition.

Abstract 413: Inhibition of Phospholipase A2 Preserves Endothelial Cell Migration in Presence of Lipid Oxidation Products

2020 ◽  
Vol 127 (Suppl_1) ◽  
Author(s):  
Priya Putta ◽  
Andrew H Smith ◽  
Pinaki Chaudhuri ◽  
Linda M Graham
Keyword(s):  
Arachidonic Acid ◽  
Endothelial Cell ◽  
Transient Receptor Potential ◽  
Phospholipase A ◽  
Oxidation Products ◽  
Endothelial Cell Migration ◽  
Enzyme Activity Assay ◽  
Vascular Intervention ◽  
Lipid Oxidation Products

During vascular intervention oxidized low-density lipoprotein (oxLDL) and lysophosphatidylcholine (lysoPC) accumulate at the site of arterial injury, which inhibits endothelial cell (EC) migration, and impedes endothelium healing. We have previously shown that lysoPC activates canonical transient receptor potential 6 (TRPC6) channel that leads to a prolonged [Ca2+]i influx, causing the inhibition in EC migration. We hypothesize that lysoPC activates phospholipase A 2 (PLA 2 ) crucial for TRPC6 activation; PLA 2 acts on cellular membranes to release arachidonic acid that opens arachidonate regulated calcium channel to release the initial calcium required to trigger TRPC6, blocking PLA 2 will prevent the opening of TRPC6 channels, preserve migration and promote endothelium healing. After incubation of bovine aortic EC with ATK or Ax048 to block PLA2G4, or with BEL, FKGK11, or FKGK18 to block PLA2G6, the effect of lysoPC-induced TRPC6 externalization and EC migration was assessed. Reversible PLA2G6 pharmacological inhibitors maximally blocked lysoPC-induced TRPC6 externalization, arachidonic acid release and preserved EC migration; exemplified with biotinylation assay, arachidonate enzyme assay, and razor scrape migration assay respectively. Immunofluorescence microscopy for TRPC6 plasma membrane translocation and PLA 2 enzyme activity assay supported these findings. To further verify the specific isoforms involved in blocking TRPC6 externalization, siRNA mediated transient knockdown studies were performed with PLA2G4A, PLA2G4C, PLA2G6A, and PLA2G6B siRNAs in EA.hy926— human endothelial cell line. PLA2G6A and not PLAG6B/4A/4C downregulation completely blocked TRPC6 externalization and preserved migration comparable to control levels. These studies confirmed the role of PLA2G6A (a calcium-independent cytosolic phospholipase A 2 group VI β isoform) in blocking lysoPC-induced TRPC6 activation and preservation of EC migration. Additional studies are in progress to confirm in vivo relevance of these findings. Our results show the potential for developing PLA 2 targeted therapies to block TRPC6 activation and promote endothelium healing, thus improving the outcomes for patients undergoing cardiovascular intervention.

3-Methoxy-2,4-di-O-methylgyrophoric acid: a novel tridepside from the lichen Parmelia subfatiscens

1981 ◽  
Vol 34 (5) ◽  
pp. 1153 ◽  
Author(s):  
JA Elix ◽  
VK Jayanthi
Keyword(s):  
Total Synthesis ◽  
Title Compound

The title compound has been isolated, characterized and the structure confirmed by total synthesis.

Oxidation products of arachidonic acid I. The synthesis of methyl 8R, 11R, 15-trihydroxy-9S, 12-oxyeicosa-5Z, 13E-dienoate (19)

1980 ◽  
Vol 21 (11) ◽  
pp. 1001-1004 ◽  
Author(s):  
George Just ◽  
Corinne Luthe ◽  
Hunseung Oh
Keyword(s):  
Arachidonic Acid ◽  
Oxidation Products

scholarly journals Methyl 1-[(Z)-2-(benzyloxycarbonyl)hydrazin-1-ylidene]-5-chloro-2-hydroxyindane-2-carboxylate

2014 ◽  
Vol 70 (5) ◽  
pp. o527-o527
Author(s):  
Kun Dong ◽  
Yifeng Wang
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Double Bond ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Compound C ◽  
Important Intermediate

The title compound, C19H17ClN2O5, is an important intermediate for the synthesis of the pesticide Indoxacarb [systematic name: (S)-methyl 7-chloro-2-{[(methoxycarbonyl)[4-(trifluoromethoxy)phenyl]amino]carbonyl}-2H,3H,4aH,5H-indeno[1,2-e][1,3,4]oxadiazine-4a-carboxylate] The C=N double bond has aZconformation. An intramolecular N—H...O hydrogen bond occurs. In the crystal structure, O—H...O hydrogen bonds result in the formation of 12-membered rings lying about inversion centers withR44(12) motifs.

The effects of oxidation products of arachidonic acid and n3 fatty acids on vascular and platelet function

2011 ◽  
Vol 45 (4) ◽  
pp. 469-476 ◽  
Author(s):  
Anne Barden ◽  
Emilie Mas ◽  
Peter Henry ◽  
Thierry Durand ◽  
Jean-Marie Galano ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Arachidonic Acid ◽  
Platelet Function ◽  
Oxidation Products
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