Relative suitability of 1-palmitoyl and 1-stearoyl homologues of 1-acyl-sn-glycerylphosphorylcholine and different acyl donors for phosphatidylcholine synthesis via acyl-CoA:1-acyl-sn-glycero-3-phosphorylcholine acyltransferase in rat lung microsomes

1980 ◽  
Vol 58 (5) ◽  
pp. 434-439 ◽  
Author(s):  
B. J. Holub ◽  
J. Plekarski ◽  
F. Possmayer
Keyword(s):  
Fatty Acids ◽  
The Other ◽  
Acyl Donor ◽  
Rat Lung ◽  
Acceptor Reaction ◽  
Acyl Acceptor ◽  
Dipalmitoyl Phosphatidylcholine ◽  
Acyl Donors ◽  
Phosphatidylcholine Synthesis ◽  
Assay Conditions

The relative suitability of the 1-palmitoyl and 1-stearoyl homologues of 1-acyl-sn-glyceryl-phosphorylcholine and different acyl donors were tested as substrates for phosphatidylcholine synthesis via the acyl-CoA:1-acyl-sn-glycero-3-phosphorylcholine acyltransferase in rat lung microsomes. The acyl acceptor was an almost equi-molar mixture of the [3H]palmitoyl plus [14C]stearoyl species of 1-acyl-sn-glycero-3-phosphorylcholine with palmitoyl-, stearoyl-, oleoyl-, linoleoyl-, or arachidonoyl-CoA serving as the acyl donor. At all concentrations of acyl acceptor, reaction velocities with 20:4-CoA ≥ 18:2-CoA > 18:1-CoA > 16:0-CoA > 18:0-CoA. Furthermore, the acyltransferase selectively utilized the 1-palmitoyl over the 1-stearoyl species of 1-acylglycerylphosphorylcholine by 4.2- to 5.7-fold under optimal assay conditions with the various acyl-CoA thiolesters. However, the degree of preference exhibited for the 1-palmitoyl-sn-glycero-3-phosphorylcholine, as acyl acceptor, versus the 1-stearoyl homologue with palmitoyl-CoA as the acyl donor was not significantly different from that obtained with the other acyl-CoA derivatives. Thus, the specificity of the acyl-CoA:1-acyl-sn-glycero-3-phosphorylcholine acyltransferase indicates an ability of this enzyme to produce dipalmitoyl phosphatidylcholine but it cannot independently explain the predominance of dipalmitoyl phosphatidylcholine in lung or the tendency of stearate at the 1-position to associate with fatty acids of increasing unsaturation at the 2-position.

Acyl specificity of CDPcholine:l,2-diacylglycerol cholinephosphotransferase in rat lung

1977 ◽  
Vol 55 (6) ◽  
pp. 609-617 ◽  
Author(s):  
F. Possmayer ◽  
G. Duwe ◽  
M. Hahn ◽  
D. Buchnea
Keyword(s):  
Fatty Acids ◽  
Unsaturated Fatty Acids ◽  
De Novo ◽  
Saturated Fatty Acids ◽  
Fetal Lung ◽  
Egg Yolk ◽  
Rat Lung ◽  
Microsomal Preparation ◽  
Dipalmitoyl Phosphatidylcholine ◽  
Egg Yolk Phosphatidylcholine

Under optimal conditions, rat lung microsomal cholinephosphotransferase (EC 2.7.8.2) activity is markedly stimulated by exogenously added 1,2-sn-diacylglycerols containing an unsaturated fatty acid at the 2-position. Diacylglycerols containing long-chain saturated fatty acids at the 1- and 2-positions did not stimulate the incorporation of CDP[14C]choline above the incorporation observed with the endogenous diacylglycerols present in the microsomal preparation. 1-Oleoyl,2-palmitoyl-sn-glycerol was also ineffective in stimulating phosphatidylcholine synthesis. Diacylglycerols containing linoleate or linolenate at the 2-position were not as effective as 1-palmitoyl,2-oleoyl-sn-glycerol. Identical stimulations were observed with the latter diacylglycerol and 'natural' diacylglycerols prepared from egg-yolk phosphatidylcholine or pig liver phosphatidylcholine. Marked selectivities were observed with diacylglycerols containing two unsaturated fatty acids. Only minor amounts of 1,2-[14C]dipalmitoyl-sn-glycerol were incorporated into phosphatidylcholine, even when this radioactive diacylglycerol was dispersed with 'egg' diacylglycerols. When CDP[14C]choline was incorporated into rat lung microsomal lipids with endogenous diacylglycerols or diacylglycerols endogenously generated by phospholipase C (EC 3.1.4.3) (Bacillus cereus), little radioactivity was associated with the disaturated species of phosphatidylcholine.It has previously been suggested that cholinephosphotransferase catalyses the rate-limiting reaction in the biosynthesis of phosphatidylcholine by lung and that this enzyme is specifically induced in fetal lung by glucocorticoids. The present results indicate that these proposals are untenable and must be reevaluated. These experiments also suggest that dipalmitoyl phosphatidylcholine is not synthesized readily by the de novo pathway for lecithin synthesis and must be produced through reacylation or transesterification mechanisms.

On the Occurrence of Monoacylglycerol Derivatives in Lipid Metabolism of Chloroplasts

1982 ◽  
Vol 37 (3-4) ◽  
pp. 218-225 ◽  
Author(s):  
Andreas Sauer ◽  
Klaus-Peter Heise
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Lipid Fraction ◽  
Acyl Donor ◽  
Rapid Synthesis ◽  
Acid Incorporation ◽  
Fatty Acid Incorporation ◽  
Acyl Acceptors ◽  
Fatty Acid Species ◽  
Acyl Donors

Abstract The aim of this investigation was to elucidate the rapid synthesis o f monogalactosyl mono­ glycerides and their role as intermediary acyl-acceptors in galactolipid synthesis of spinach chlo­ roplasts. The problem was attacked by studying the incorporation o f sn-[14C]glycerol-3-phosphate and [l-14C]acetate into the lipid fraction o f gently shocked and reconstituted preparations. The data revealed: 1 . a concurrent accumulation o f both monoglycerides and monogalactosyl monoglycerides under acidic incubation conditions, with C16-fatty acid species predominating, 2 . similarities in the fatty acid incorporation of both monoacyllipids, 3. the occurrence o f two isomeric forms viz. 1 -and 2-O-acyl-isomers o f these lipids. Thus, it appears that monogalactosyl monoglycerides are synthesized by galactosylation o f mo­ noglycerides rather than by galactolipase hydrolysis. Both monoacyllipids are likely to be derived from the corresponding lysophosphatidic acids by dephosphorylation. Their fatty acid incorporation pattern therefore may contribute to an under­ standing of the specific esterification o f different fatty acids at the Ct-and exp osition of the gly­ cerol moiety of galactolipids. Analysis o f the specific acylation o f monoglycerides and monogalac­ tosyl monoglycerides as well as the nature of the acyl donors involved in this fatty acid transfer yielded the following observations: 5. The position of the fatty acids within the monoacyllipids seems to depend on whether acyl-ACP or acyl-CoA is the primary acyl donor. 6 . The characteristics of the fatty acid incorporation into monoglycerides and their galactosylated derivatives support the notion that a successive acylation o f sn-glycerol-3-phosphate occurs first in the C2-and then in the Q-position. 7. In contrast, the chain length o f the fatty acids incorporated seems to be determined by such fac­ tors as pH and the concentration o f sn-glycerol-3-phosphate. This observation suggests that these parameters may act by controlling the elongation o f ACP-bound C16-fatty acids to their C18-species.

Cellular distribution of enzymes involved in phosphatidylcholine synthesis in developing rat lung

1983 ◽  
Vol 61 (2-3) ◽  
pp. 107-114 ◽  
Author(s):  
Frank Chan ◽  
Paul G. R. Harding ◽  
Tanya Wong ◽  
G. Frazer Fellows ◽  
Fred Possmayer
Keyword(s):  
Microsomal Fraction ◽  
Specific Activity ◽  
Perinatal Period ◽  
Rat Lung ◽  
Developmental Profile ◽  
Dipalmitoyl Phosphatidylcholine ◽  
Choline Incorporation ◽  
Developing Rat ◽  
Phosphatidylcholine Synthesis ◽  
Nadph Cytochrome C Reductase

The incorporation of radioactive choline into phosphatidylcholine and disaturated phosphatidylcholine in rat lung slices increased markedly before term and peaked after birth. The specific activity of cholinephosphate cytidylyltransferase in the microsomal fraction increased before birth but fell after delivery. The specific activity of this enzyme in the cytosol showed a marked increase at birth. The developmental profile for the total cytosolic activity per gram lung was similar to the pattern observed with choline incorporation. Although the specific activity of cholinephosphotransferase in the whole homogenate remained relatively constant throughout pulmonary maturation, there was a marked increase in the specific activity of this enzyme in the microsomal fraction at term. Similar findings were obtained with the microsomal marker NADPH-cytochrome c reductase. The basis of this disparity in specific activity profiles is being investigated further. The specific activity of lysophosphatidylcholine: lysophosphatidylcholine transacylase in rat lung homogenates increased during gestation but rose a further 10-fold between day 3 after birth and the adult. The specific activity of lysophosphatidylcholine: palmitoyl-CoA acyltransferase remained relatively constant throughout development. At term, the specific activity of the acylation enzyme was 10- to 15-fold greater than the specific activity of the transacylation enzyme. These observations are consistent with previous studies indicating that the accumulation of phosphatidylcholine and dipalmitoyl phosphatidylcholine during the perinatal period may be due to alterations in the activity of cholinephosphate cytidylyltransferase. Cholinephosphotransferase could also play a regulatory role. The formation of dipalmitoyl phosphatidylcholine appears to occur via the acylation, rather than the transacylation pathway.

scholarly journals Effect of Dietary Hazelnut Peels on the Contents of Fatty Acids, Cholesterol, Tocopherols, and on the Shelf-Life of Ripened Ewe Cheese

Antioxidants ◽  
2021 ◽  
Vol 10 (4) ◽  
pp. 538
Author(s):  
Vita Maria Marino ◽  
Teresa Rapisarda ◽  
Margherita Caccamo ◽  
Bernardo Valenti ◽  
Alessandro Priolo ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Dry Matter ◽  
Tocopherol Content ◽  
The Other ◽  
Cholesterol Oxidation ◽  
Cholesterol Levels ◽  
Bulk Milk ◽  
Chocolate Industry ◽  
Experimental Group ◽  
Effect Of Feeding

Hazelnut peel (HNP), a by-product from the chocolate industry, is considered to be a suitable ingredient to be included in the diet of ruminants. This study aimed to evaluate the effect of feeding dairy ewes with a diet containing HNP on ripened cheese quality, including fatty acid (FA) profile, cholesterol, and tocopherol content, as well as stability during storage under commercial conditions. In total, 10 experimental cheeses were produced with bulk milk obtained from ewes fed a commercial concentrate (C group; n = 5) or a concentrate containing 36% HNP in dry matter (HNP group; n = 5). After 40 days of aging, each cheese was sub-sampled into three slices: one was analyzed immediately (C0 and HNP0), and the other two were refrigerated and analyzed after seven days (C7 and HNP7) and 14 days (C14 and HNP14), respectively. Compared to C, HNP cheese had more than twice as many tocopherols and mono-unsaturated FA and respectively 38% and 24% less of cholesterol and saturated FA. Tocopherols and cholesterol levels remained rather stable up to 14 days of storage regardless of the experimental group, suggesting no cholesterol oxidation. Therefore, the inclusion of HNP in ewe diets could be a valid resource to produce cheese with a healthier lipid profile and higher tocopherols content.

scholarly journals Effect of Dietary Fat Composition and 2’Fucosyllactose on Neonatal Piglet Growth and Organ Lipid Composition

2020 ◽  
Vol 4 (Supplement_2) ◽  
pp. 1038-1038
Author(s):  
Michael Miklus ◽  
Pedro Prieto ◽  
Cynthia Barber ◽  
Robert Rhoads ◽  
Samer El-Kadi
Keyword(s):  
Fatty Acids ◽  
Body Weight ◽  
Fatty Acid ◽  
Body Weight Gain ◽  
Dietary Fatty Acids ◽  
The Body ◽  
The Other ◽  
Human Infant ◽  
Lps Challenge ◽  
Group 3

Abstract Objectives The objectives of this study were to determine the effect of 2’fucosyllactose (2’FL) and fat blends on growth, body composition and fatty acid profile of the liver and brain using the neonatal pig as a model for the human infant. Methods Pigs (3 d old) were randomly assigned to either: 1. control, 2. Palm Olein (PO) fat blend – Low 2'-FL, 3. PO – High 2'-FL, 4. High oleic acid (HO) – Low 2'-FL, 5. HO FB – High 2'-FL, 6. PO FB – GLA, or 7. kept with their sows. Pigs in groups 1 to 6 received 250 ml·kg−1·d−1 of formula in 5 equal meals for 15 d. On day 14 of the study, groups 1–6 received intraperitoneal E. coli LPS challenge at 100 µg·kg−1 weight. Results Body weight was greater for piglets fed by sows than those in the other groups (P < 0.001). In addition, % fat and bone mineral content were higher in the sow-fed group while lean % was less sow-fed piglets (group 7) compared with those in the other groups (P < 0.05). Only longissimus weight expressed as a % of body weight, was greater for group 7 compared with all other groups (P < 0.001). Soleus, semitendinosus, brain, heart and spleen weights as a % of body weight were similar across all groups. However, liver weight as a % of body weight was greater in groups 1–6 (3.7%) compared with group 7 (2.8%; P < 0.001). The proportion of brain 16:1 fatty acid was less (0.83%) for groups 1–6 than for group 7 pigs (1.08%; P < 0.0001). The proportion of 20:3 N6 was greatest (0.66%) for group 3 compared with groups 1 and 4 (0.55%; P < 0.05). In addition, the proportion of 20:5 N3 was greatest (0.12%) for group 3 compared with groups 1 and 7 (0.07%; P < 0.05). The proportion of liver 16:1, 18:0, and 18:1 cis-11 fatty acids were greater for group 7 (2.3, 23, 2.2%) than groups 1–6 (0.2, 20, 1.2%; P < 0.0001). Conversely, the contribution of 14:0, 18:1 cis-9, 18:3 N6 cis-6,9,12, and 22:6 N3 were greater for pigs in groups 1–6 (1.3, 0.6, and 14, 7.8%) compared with those in group 7 (0.5, 8.5, 0.2 and 3.5%; P < 0.0001). Conclusions Our data suggest that feeding 2’fucosyllactose had no effect on the body weight gain and composition in neonatal pigs. Our data also suggest that dietary fatty acids have a greater effect on liver than on brain fatty acid composition. Funding Sources Funding for the work was provided by Perrigo Nutritionals, LLC.

Unsaturated fatty acids in the postnatally developing rat lung

Lipids ◽  
1983 ◽  
Vol 18 (1) ◽  
pp. 50-54
Author(s):  
James P. Kehrer ◽  
Anne P. Autor
Keyword(s):  
Fatty Acids ◽  
Unsaturated Fatty Acids ◽  
Rat Lung ◽  
Developing Rat

scholarly journals The Aminolysis Reaction of Streptomyces S9 Aminopeptidase Promotes the Synthesis of Diverse Prolyl Dipeptides

2010 ◽  
Vol 76 (12) ◽  
pp. 4109-4112 ◽  
Author(s):  
Jiro Arima ◽  
Masazumi Morimoto ◽  
Hirokazu Usuki ◽  
Nobuhiro Mori ◽  
Tadashi Hatanaka
Keyword(s):  
Conversion Ratio ◽  
Acyl Donor ◽  
Acyl Acceptor ◽  
Broad Specificity

ABSTRACT Prolyl dipeptide synthesis by S9 aminopeptidase from Streptomyces thermocyaneoviolaceus (S9AP-St) has been demonstrated. In the synthesis, S9AP-St preferentially used l-Pro-OBzl as the acyl donor, yielding synthesized dipeptides having an l-Pro-Xaa structure. In addition, S9AP-St showed broad specificity toward the acyl acceptor. Furthermore, S9AP-St produced cyclo (l-Pro-l-His) with a conversion ratio of substrate to cyclo (l-Pro-l-His) higher than 40%.

scholarly journals Production of Structured Phosphatidylcholine with High Content of Myristic Acid by Lipase-Catalyzed Acidolysis and Interesterification

Catalysts ◽  
2018 ◽  
Vol 8 (7) ◽  
pp. 281 ◽  
Author(s):  
Anna Chojnacka ◽  
Witold Gładkowski
Keyword(s):  
Myristic Acid ◽  
Rhizomucor Miehei ◽  
Egg Yolk ◽  
Thermomyces Lanuginosus ◽  
Molar Ratio ◽  
Acyl Donor ◽  
Thermomyces Lanuginosus Lipase ◽  
Screening Experiments ◽  
Miehei Lipase ◽  
Acyl Donors

Synthesis of structured phosphatidylcholine (PC) enriched with myristic acid (MA) was conducted by acidolysis and interesterification reactions using immobilized lipases as catalysts and two acyl donors: trimyristin (TMA) isolated from ground nutmeg, and myristic acid obtained by saponification of TMA. Screening experiments indicated that the most effective biocatalyst for interesterification was Rhizomucor miehei lipase (RML), whereas for acidolysis, the most active were Thermomyces lanuginosus lipase (TLL) and RML. The effect of the molar ratio of substrates (egg-yolk PC/acyl donor), enzyme loading, and different solvent on the incorporation of MA into PC and on PC recovery was studied. The maximal incorporation of MA (44 wt%) was achieved after 48 h of RML-catalyzed interesterification in hexane using substrates molar ratio (PC/trimyristin) 1/5 and 30% enzyme load. Comparable results were obtained in toluene with 1/3 substrates molar ratio. Interesterification of PC with trimyristin resulted in significantly higher MA incorporation than acidolysis with myristic acid, particularly in the reactions catalyzed by RML.

Enantioselective Enzymatic Synthesis of ( R )‐Phenyl Alkyl Esters and Their Analogue Amides using Fatty Acids as Green Acyl Donors.

2021 ◽  
Vol 6 (48) ◽  
pp. 13941-13946
Author(s):  
Nour ElHouda Benamara ◽  
Mounia Merabet‐Khelassi ◽  
Samia Guezane Lakoud ◽  
Louisa Aribi‐Zouioueche ◽  
Olivier Riant
Keyword(s):  
Fatty Acids ◽  
Enzymatic Synthesis ◽  
Alkyl Esters ◽  
Acyl Donors
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