The Occurrence and Distribution of Cholesterol and allied Bodies in the Animal Kingdom

Glyceryl-ether monooxygenase [EC 1.14.16.5]. A microsomal enzyme of ether lipid metabolism

“…31 Enantiomerically pure glyceryl ethers (12, chiral at C2) were prepared from the corresponding chiral 1,2-isopropylidene glycerols, 13,26,31,139 and by using radiolabeled ( 14 C and/or 3 H) reactive alkyl derivatives and/or radioactive isopropylidene glycerol appropriately labeled, radiolabeled ␣-alkyl glycerols have been prepared. 136 No inversion of configuration occurs at the prochiral carbon atom C3 in (10) or (11) in this reaction, but inversion at the ␣-carbon atom of the reactive alkyl derivative does take place. We have shown this by condensing the sodium salt (9, 2RS) with R-[1-2 H]-hexadecyl tosylate which gave (1ЈS)-[1Ј-2 H]-3-hexadecyloxy-(2RS)-propane-1,2-diol, whereas condensation of (2RS)-isopropylidene tosylate with the sodi-…”

“…Today racemic isopropylidene glycerol, as well as its pure chiral enantiomers, are readily available commercially and have increased the popularity of this method considerably. Its metal salts (10) were prepared by reaction with sodium naphthalene, 13 dispersed sodium metal, 134 potassium metal, [135][136][137] and more recently sodium hydride (from a 60% dispersion in mineral oil) 31,138 in anhydrous inert solvents such as benzene, xylene, tetrahydrofuran or dimethyl formamide under dry nitrogen. After complete conversion to the salt (10), the reactive alkyl derivative such as the bromide, 138 137 in an inert solvent as above was added, and the mixture refluxed for several hours (4-48 h).…”

Historical perspective: phosphatidylserine and phosphatidylethanolamine from the 1800s to the present

“…The existence of a unique class of phosphorus-containing lipids that contain an O-alkyl group was first proposed by Doree (221) in 1909 in England. Later, in 1929, Feulgen, Imhauser, and Behrens (222) discovered that when a phosphatide fraction was stained with fuchsin sulfurous acid, a purple color developed that was characteristic of an aldehyde; the presence of the aldehyde was apparently due to the degradation of the alkyl or alkenyl bond of this novel class of lipids.…”

Pharmacological Developments Obtained from Marine Natural Products and Current Pipeline Perspective

“…Two years later, he published the chemical structure of some pigments, and isolated a uridine nucleotide from several marine organisms [7][8][9]. The work of Krukenberg inspired new researchers to investigate and isolate new molecules from marine organisms, such as cholesterol-related compounds and some marine pigments [10]. In this case, the most salient work was the isolation of spongosterin (1) and spongosterol (2) from the sponge Suberites domuncula [11,12].…”