scholarly journals Metabolism of the diacetyl derivatives of stereoisomeric monoacyl-sn-glycerols by rat adipocytes in vitro

1986 ◽  
Vol 235 (3) ◽  
pp. 833-838 ◽  
Author(s):  
W W Christie ◽  
M L Hunter
Keyword(s):  
Oleic Acid ◽  
Significant Degree ◽  
Partial Hydrolysis ◽  
Unesterified Fatty Acid ◽  
Triacylglycerol Biosynthesis ◽  
Bonded Phase ◽  
High Degree ◽  
Hydrolysis Of ◽  
Derivatives Of

Diacetyl long-chain 1(3)- and 2-acyl-sn-glycerols containing either [9,10-3H]oleic acid or [1-14C]palmitic acid were synthesized by partial hydrolysis of the corresponding labelled triacylglycerols and acetylation. They were obtained in a high degree of stereochemical purity by preparative h.p.l.c. on a column containing a diol bonded phase. Each compound was rapidly metabolized by adipocyte preparations in vitro, and a high proportion of the label was recovered in the unesterified fatty acid and triacylglycerol fractions. Negligible amounts of intermediate products of hydrolysis were detected. Triacylglycerols were formed from [9,10-3H]oleic acid and from diacetyl-1(3)-[9,10-3H]oleoyl glycerol precursors at about the same rate, but the 2-isomer was metabolized rather more slowly. The results were consistent with the hypothesis that essentially complete hydrolysis occurred in the medium or at the plasma membrane, through the actions of lipoprotein lipase and monoacylglycerol lipase, and that subsequent esterification took place within the cell. To confirm that no putative intermediate monoacylglycerols were utilized for triacylglycerol biosynthesis via the monacylglycerol pathway, the positional distributions of fatty acids in triacylglycerols from each substrate were determined. No positional selectivity was observed. It was concluded that monoacylglycerols, of an origin exogenous to the tissue, e.g. those derived from plasma triacylglycerols, were not utilized to a significant degree for triacylglycerol biosynthesis in adipose tissue. The diacetyl derivatives of monoacylglycerols may serve as useful stereochemical probes in studies of triacylglycerol biosynthesis via the monoacylglycerol pathway in other tissues.

scholarly journals Novel Amino Acid Derivatives of Quinolines as Potential Antibacterial and Fluorophore Agents

2020 ◽  
Vol 88 (4) ◽  
pp. 57
Author(s):  
Oussama Moussaoui ◽  
Rajendra Bhadane ◽  
Riham Sghyar ◽  
El Mestafa El Hadrami ◽  
Soukaina El Amrani ◽  
...  
Keyword(s):  
Amino Acid ◽  
Methyl Esters ◽  
Amino Acid Derivatives ◽  
Bacterial Strains ◽  
Fluorescent Properties ◽  
Topoisomerase Iv ◽  
Microdilution Method ◽  
Hydrolysis Of ◽  
Derivatives Of

A new series of amino acid derivatives of quinolines was synthesized through the hydrolysis of amino acid methyl esters of quinoline carboxamides with alkali hydroxide. The compounds were purified on silica gel by column chromatography and further characterized by TLC, NMR and ESI-TOF mass spectrometry. All compounds were screened for in vitro antimicrobial activity against different bacterial strains using the microdilution method. Most of the synthesized amino acid-quinolines show more potent or equipotent inhibitory action against the tested bacteria than their correspond esters. In addition, many of them exhibit fluorescent properties and could possibly be utilized as fluorophores. Molecular docking and simulation studies of the compounds at putative bacterial target enzymes suggest that the antimicrobial potency of these synthesized analogues could be due to enzyme inhibition via their favorable binding at the fluoroquinolone binding site at the GyrA subunit of DNA gyrase and/or the ParC subunit of topoisomerase-IV.

O-Benzylidene Derivatives of D-Arabinose Diethyl and Dipropyl Dithioacetal

1996 ◽  
Vol 49 (3) ◽  
pp. 273 ◽  
Author(s):  
J Kuszmann ◽  
E Gacsbaitz
Keyword(s):  
Hydrochloric Acid ◽  
Zinc Chloride ◽  
Partial Hydrolysis ◽  
Kinetic Control ◽  
Toluenesulfonic Acid ◽  
Thermodynamic Phase ◽  
Hydrolysis Of ◽  
Derivatives Of

Benzylidenation of D-arabinose diethyl and dipropyl dithioacetals with α,α-dimethoxytoluene in the presence of p-toluenesulfonic acid has been studied in detail. Under kinetic control the two terminal dioxolan -type 4,5-O-(R)- and 4,5-O-(S)-benzylidene diastereomers are formed first which are in equilibrium with each other In the thermodynamic phase of the reaction the corresponding dioxan -type 3,5-O-(R)- benzylidene isomer is formed too, but all three monobenzylidene isomers are gradually converted into the four possible dioxolan -type 2,3 : 4,5-di-O benzylidene diastereomers . The dioxan -type 2,4:3,5-di-O-benzylidene isomer was present only in trace amounts. When benzaldehyde was used as reagent in the presence of hydrochloric acid or zinc chloride only the 2,3: 4,5-di-O-benzylidene diastereomers were formed. Partial hydrolysis of the dibenzylidene derivatives yielded the corresponding 2,3-O-benzylidene diastereomers. Structures, including the chirality of the benzylidene groups, were determined by n.m.r. spectroscopy. A mechanism suggested for the reaction was partially supported by equilibration studies.

Hydrolytic products of 4-aryl-2,3-dicyano-1-naphthol derivatives

1981 ◽  
Vol 46 (9) ◽  
pp. 2207-2216 ◽  
Author(s):  
Jiří Křepelka ◽  
Iva Vančurová ◽  
Jiří Holubek ◽  
Jiří Roubík
Keyword(s):  
Dicarboxylic Acids ◽  
Ring Closure ◽  
Partial Hydrolysis ◽  
H Nmr ◽  
Antiviral Effects ◽  
Hydrolysis Of ◽  
Derivatives Of ◽  
Naphthol Derivatives ◽  
Intramolecular Ring

Depending on the conditions of hydrolysis, vicinal aromatic dicyano derivatives Ia-Ic gave anhydrides IIa-IIe and imides of 4-aryl-1-alkoxynaphthalene-2,3-dicarboxylic acids, IIIa,b, along with products of partial hydrolysis, decarboxylation and demethylation, IVa-IVd, IVf-IVg, and derivatives of benzo(c)fluorene, Va-Vc. The derivatives Va-Vc were also obtained by acid hydrolysis of dicyano derivatives Id-Ig. Methanolysis of the anhydride IId gave a mixture of positional isomers, IVh, which was esterified to the diester IVe. Intramolecular ring closure of the isomers IVh afforded derivatives of benzo(c)fluorene, VIa-VIb. The structures of the selected compounds were corroborated by IR and 1H NMR spectra. The compounds Va-Vc exhibited antiviral effects and interferonogenic activities in vivo.

Partial hydrolysis of acyl 1,6-anhydro-β-D-glucopyranose

1984 ◽  
Vol 49 (8) ◽  
pp. 1780-1787 ◽  
Author(s):  
Štefan Kučár ◽  
Juraj Zámocký ◽  
Juraj Zemek ◽  
Dušan Anderle ◽  
Mária Matulová
Keyword(s):  
Acid Hydrolysis ◽  
Hydrazine Hydrate ◽  
Hydrogen Chloride ◽  
Ester Group ◽  
The Other ◽  
Hydroxyl Group ◽  
Partial Hydrolysis ◽  
Substantial Influence ◽  
Hydrolysis Of ◽  
Derivatives Of

Partial hydrolysis of per-O-acetyl- and per-O-benzoyl derivatives of 1,6-anhydro-β-D-glucopyranose with methanolic hydrogen chloride and hydrazine hydrate was investigated. The acyl group at C(3) is of substantial influence on the course of hydrolysis. The esterified hydroxyl group at C(3) was found to be most stable on acid hydrolysis with methanolic hydrogen chloride when compared with that at C(2), or C(4); on the other hand, this ester group is the most labile upon hydrolysis with hydrazine hydrate. Selectivity of the respective ester groups towards hydrolysis made it possible to prepare all variations of acetyl and benzoyl derivatives of 1,6-anhydro-β-D-glucopyranose.

In vitro hydrolysis of polyunsaturated fatty acid N-acyloxymethyl derivatives of theophylline

1998 ◽  
Vol 165 (1) ◽  
pp. 87-96 ◽  
Author(s):  
Peter Redden ◽  
Jo-Anne E Douglas ◽  
Michael J Burke ◽  
David F Horrobin
Keyword(s):  
Fatty Acid ◽  
Polyunsaturated Fatty Acid ◽  
In Vitro Hydrolysis ◽  
Hydrolysis Of ◽  
Derivatives Of

Partial Hydrolysis of Cowʼs Milk Proteins by Human Trypsins and Elastases In Vitro

1983 ◽  
Vol 2 (4) ◽  
pp. 613-616 ◽  
Author(s):  
Irene Jakobsson ◽  
Stefan Borulf ◽  
Tor Lindberg ◽  
Birgitta Benediktsson
Keyword(s):  
Milk Proteins ◽  
Partial Hydrolysis ◽  
Hydrolysis Of

scholarly journals Synthesis and In Vitro Evaluation of Caffeoylquinic Acid Derivatives as Potential Hypolipidemic Agents

Molecules ◽  
2019 ◽  
Vol 24 (5) ◽  
pp. 964 ◽  
Author(s):  
Yu Tian ◽  
Xiao-Xue Cao ◽  
Hai Shang ◽  
Chong-Ming Wu ◽  
Xi Zhang ◽  
...  
Keyword(s):  
Oleic Acid ◽  
Chlorogenic Acid ◽  
Positive Control ◽  
Biological Evaluation ◽  
Lipid Lowering ◽  
Caffeoylquinic Acid ◽  
Hypolipidemic Agents ◽  
Derivatives Of ◽  
Lipid Lowering Effect

A series of novel caffeoylquinic acid derivatives of chlorogenic acid have been designed and synthesized. Biological evaluation indicated that several synthesized derivatives exhibited moderate to good lipid-lowering effects on oleic acid-elicited lipid accumulation in HepG2 liver cells. Particularly, derivatives 3d, 3g, 4c and 4d exhibited more potential lipid-lowering effect than the positive control simvastatin and chlorogenic acid. Further studies on the mechanism of 3d, 3g, 4c and 4d revealed that the lipid-lowering effects were related to their regulation of TG levels and merit further investigation.

In vitro hydrolysis of novel gamma-linolenoyloxyalkyl derivatives of theophylline

1997 ◽  
Vol 157 (1) ◽  
pp. 81-91 ◽  
Author(s):  
Michael Burke ◽  
Peter R. Redden ◽  
Jo-Anne Douglas ◽  
Arthur Dick ◽  
David F. Horrobin
Keyword(s):  
In Vitro Hydrolysis ◽  
Hydrolysis Of ◽  
Derivatives Of

The hydrolytic activity of L-ascorbic acid

1976 ◽  
Vol 54 (11) ◽  
pp. 1018-1021
Author(s):  
J. N. Kanfer ◽  
C. H. Spielvogel
Keyword(s):  
Ascorbic Acid ◽  
Oleic Acid ◽  
Hydrolytic Activity ◽  
In Vitro Systems ◽  
Hydrolysis Of

The ability of L-ascorbic acid to catalyze the liberation of 4-methylumbelliferone from 4-methylumbelliferyl-β-D-N-acetylgiucosaminide, 4-methylumbelliferyl-β-D-glucuronide, 4-methlumbelliferyl-α-D-mannoside, and 4-methylumbelliferyl-β-D-galactoside is documented. There is an apparent metal and oxygen dependency. The cleavage of two lipids was shown in addition to the hydrolysis of these fluorogenic glycosides. Galactose was liberated from galactosyl-6-[3H]ceramide and oleic acid from cholesterol-[1-14C]oleate by L-ascorbic acid under conditions usually used for in vitro incubations. In common with most in vitro systems, only a small percentage of substrate was degraded.

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