Acidolysis and glyceride synthesis reactions using fatty acids with two Pseudomonas lipases having different substrate specificities

2006 ◽  
Vol 102 (3) ◽  
pp. 179-183 ◽  
Author(s):  
Yuzo Kojima ◽  
Eiji Sakuradani ◽  
Sakayu Shimizu
Keyword(s):  
Fatty Acids ◽  
Substrate Specificities ◽  
Glyceride Synthesis ◽  
Synthesis Reactions

scholarly journals The regulation of glyceride synthesis in isolated white-fat cells. The effects of palmitate and lipolytic agents

1972 ◽  
Vol 128 (5) ◽  
pp. 1057-1067 ◽  
Author(s):  
E. D Saggerson
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Free Fatty Acids ◽  
Fatty Acid Synthesis ◽  
Acid Synthesis ◽  
Fat Cells ◽  
Glyceride Synthesis ◽  
Glucose Incorporation ◽  
High Concentrations ◽  
Stimulation Of

1. 0.5mm-Palmitate stimulated incorporation of [U-14C]glucose into glyceride glycerol and fatty acids in normal fat cells in a manner dependent upon the glucose concentration. 2. In the presence of insulin the incorporation of 5mm-glucose into glyceride fatty acids was increased by concentrations of palmitate, adrenaline and 6-N-2′-O-dibutyryladenosine 3′:5′-cyclic monophosphate up to 0.5mm, 0.5μm and 0.5mm respectively. Higher concentrations of these agents produced progressive decreases in the rate of glucose incorporation into fatty acids. 3. The effects of palmitate and lipolytic agents upon the measured parameters of glucose utilization were similar, suggesting that the effects of lipolytic agents are mediated through increased concentrations of free fatty acids. 4. In fat cells from 24h-starved rats, maximal stimulation of glucose incorporation into fatty acids was achieved with 0.25mm-palmitate. Higher concentrations of palmitate were inhibitory. In fat cells from 72h-starved rats, palmitate only stimulated glucose incorporation into fatty acids at high concentrations of palmitate (1mm and above). 5. The ability of fat cells to incorporate glucose into glyceride glycerol in the presence of palmitate decreased with increasing periods of starvation. 6. It is suggested that low concentrations of free fatty acids stimulate fatty acid synthesis from glucose by increasing the utilization of ATP and cytoplasmic NADH for esterification of these free fatty acids. When esterification of free fatty acids does not keep pace with their provision, inhibition of fatty acid synthesis occurs. Provision of free fatty acids far in excess of the esterification capacity of the cells leads to uncoupling of oxidative phosphorylation and a secondary stimulation of fatty acid synthesis from glucose.

scholarly journals Evidence for the regulation of guinea-pig heart microsomal phosphatidylcholine-hydrolysing phospholipase A1 by guanosine 5′-[γ-thio]triphosphate

1992 ◽  
Vol 288 (3) ◽  
pp. 965-968 ◽  
Author(s):  
K Badiani ◽  
X Lu ◽  
G Arthur
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Guinea Pig ◽  
Molecular Species ◽  
Inhibitory Effect ◽  
Phospholipase A1 ◽  
Guinea Pig Heart ◽  
Substrate Specificities ◽  
Rate Of Hydrolysis ◽  
Hydrolysis Of

We have recently characterized lysophospholipase A2 activities in guinea-pig heart microsomes and postulated that these enzymes act sequentially with phospholipases A1 to release fatty acids selectively from phosphatidylcholine (PC) and phosphatidylethanolamine, thus providing an alternative route to the phospholipase A2 mode of release. In a further investigation of the postulated pathway, we have characterized the PC-hydrolysing phospholipase A1 in guinea-pig heart microsomes. Our results show that the enzyme may have a preference for substrates with C16:0 over C18:0 at the sn-1 position. In addition, although the enzyme cleaves the sn-1 fatty acid, the rate of hydrolysis of PC substrates with C16:0 at the sn-1 position was influenced by the nature of the fatty acid at the sn-2 position. The order of decreasing preference was C18:2 > C20:4 = C18:1 > C16:0. The hydrolyses of the molecular species were differentially affected by heating at 60 degrees C. An investigation into the effect of nucleotides on the activity of the enzyme showed that guanosine 5′-[gamma-thio]triphosphate (GTP[S]) inhibited the hydrolysis of PC by phospholipase A1 activity, whereas GTP, guanosine 5′-[beta-thio]diphosphate (GDP[S]), GDP, ATP and adenosine 5′-[gamma-thio]triphosphate (ATP[S]) did not affect the activity. The inhibitory effect of GTP[S] on phospholipase A1 activity was blocked by preincubation with GDP[S]. A differential effect of GTP[S] on the hydrolysis of different molecular species was also observed. Taken together, the results of this study suggest the presence of more than one phospholipase A1 in the microsomes with different substrate specificities, which act sequentially with lysophospholipase A2 to release linoleic or arachidonic acid selectively from PC under resting conditions. Upon stimulation and activation of the G-protein, the release of fatty acids would be inhibited.

Lipase-catalyzed esterification of glycerol with n-3 polyunsaturated fatty acids from winterized fish oil Esterificación catalítica de glicerol con ácidos grasos 3-n poliinsaturados de aceite de pescado

1998 ◽  
Vol 4 (6) ◽  
pp. 401-405 ◽  
Author(s):  
V.J. Robles ◽  
H.S. García ◽  
J.A. Monroy ◽  
O. Angulo
Keyword(s):  
Fatty Acids ◽  
Docosahexaenoic Acid ◽  
Polyunsaturated Fatty Acids ◽  
Eicosapentaenoic Acid ◽  
Phosphate Buffer ◽  
Esterification Reaction ◽  
Pseudomonas Sp ◽  
Menhaden Oil ◽  
Glyceride Synthesis ◽  
Esterified Fatty Acids

Menhaden oil was hydrolyzed using a lipase from Pseudomonas sp. The hydrolysate was cold frac tionated at-72°C. Glyceride synthesis was performed using the same lipase under different reaction environments. The best conditions for the esterification reaction were 39 °C for 18 h in a reaction mixture containing anhydrous glycerol, n-3 polyunsaturated fatty acids (PUFA) enriched solution (2% lipids in hexane), hexane, and phosphate buffer-lipase solution (1% w/v). Product composition was 81.33% triacylglycerides and 18.67% of free fatty acids (w/w). Eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) accounted for 36.18% of the esterified fatty acids, of which 58% was EPA and 42% was DHA. This method offers an alternative to produce glycerides rich in n-3 PUFA.

scholarly journals Studies on the role of insulin in the regulation of glyceride synthesis in rat epididymal adipose tissue

1975 ◽  
Vol 150 (3) ◽  
pp. 441-451 ◽  
Author(s):  
S R Sooranna ◽  
E D Saggerson
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Fatty Acid Synthesis ◽  
Acid Synthesis ◽  
Synthesis Process ◽  
Epididymal Adipose Tissue ◽  
Fat Cells ◽  
Fat Cell ◽  
Glyceride Synthesis

1. When rat isolated fat-cells were incubated with fructose and palmitate, insulin significantly stimulated glyceride synthesis as measured by either [14C]fructose incorporation into the glycerol moiety or of [3H]palmitate incorporation into the acyl moiety of tissue glycerides. Under certain conditions the effect of insulin on glyceride synthesis was greater than the effect of insulin on fructose uptake. 2. In the presence of palmitate, insulin slightly stimulated (a) [14C]pyruvate incorporation into glyceride glycerol of fat-cells and (b) 3H2O incorporation into glyceride glycerol of incubated fat-pads. 3. At low extracellular total concentrations of fatty acids (in the presence of albumin), insulin stimulated [14C]fructose, [14C]pyruvate and 3H2O incorporation into fat-cell fatty acids. Increasing the extracellular fatty acid concentration greatly inhibited fatty acid synthesis from these precursors and also greatly decreased the extent of apparent stimulation of fatty acid synthesis by insulin. 4. These results are discussed in relation to the suggestion [A.P. Halestrap & R.M Denton (1974) Biochem. J. 142, 365-377] that the tissue may contain a specific acyl-binding protein which is subject to regulation. It is suggested that an insulin-sensitive enzyme component of the glyceride-synthesis process may play such a role.

scholarly journals The regulation of glyceride synthesis in isolated white-fat cells. The effects of acetate, pyruvate, lactate, palmitate, electron-acceptors, uncoupling agents and oligomycin

1972 ◽  
Vol 128 (5) ◽  
pp. 1069-1078 ◽  
Author(s):  
E. D Saggerson
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Fatty Acid Synthesis ◽  
Acid Synthesis ◽  
Fat Cells ◽  
Dependent Manner ◽  
Concentration Dependent Manner ◽  
Normal Cells ◽  
Glyceride Synthesis ◽  
Glucose Incorporation

1. The incorporation of 5mm-[U-14C]glucose into glyceride fatty acids by fat cells from normal rats incubated in the presence of 20munits of insulin/ml was increased by acetate, pyruvate, palmitate, NNN′N′-tetramethyl-p-phenylenediamine, phenazine methosulphate, dinitrophenol, tetrachlorotrifluoromethyl benzimidazole and oligomycin. Lactate did not stimulate glucose incorporation into fatty acids. The effects of these agents were concentration-dependent. 2. In the presence of 5mm-glucose+insulin, [U-14C]acetate, [U-14C]pyruvate and [U-14C]lactate were incorporated into fatty acids in a concentration-dependent manner, thereby further increasing the total rate of fatty acid synthesis. 3. NNN′N′-tetramethyl-p-phenylenediamine decreased the incorporation of [U-14C]pyruvate into fatty acids in normal cells and increased the incorporation of [U-14C]lactate into fatty acids. 4. In fact cells from 72h-starved rats the stimulatory effects of NNN′N′-tetramethyl-p-phenylenediamine upon glucose and lactate incorporation into fatty acids were totally and partially abolished respectively whereas the stimulatory effects of acetate upon glucose incorporation were retained. 5. Combinations of the optimum concentrations of the substances that stimulate glucose incorporation into fatty acids were tested and compared. The effects of acetate+NNN′N′-tetramethyl-p-phenylenediamine and acetate+palmitate upon normal cells were additive. The effects of NNN′N′-tetramethyl-p-phenylenediamine+palmitate were not additive. It was found that total fatty acid synthesis in the presence of glucose was most effectively increased by raising the concentration of pyruvate in the incubation system. 6. The significance of these results in supporting the proposal that fatty acid synthesis from glucose in adipose tissue is a ‘self-limiting process’ is discussed.

GLYCERIDE SYNTHESIS: I. SYNTHESIS OF SYMMETRICAL DIGLYCERIDES FROM DIHYDROXY ACETONE AND ALLYL ALCOHOL

1955 ◽  
Vol 33 (4) ◽  
pp. 716-721 ◽  
Author(s):  
P. J. Barry ◽  
B. M. Craig
Keyword(s):  
Fatty Acids ◽  
Allyl Alcohol ◽  
Methyl Esters ◽  
Ketone Group ◽  
Glyceride Synthesis ◽  
Tetrahydropyranyl Ether

1,3-Distearoxy acetone and 1,3-dipalmitoxy acetone were prepared by interesterification of the methyl esters of the fatty acids with 1,3-dipropionoxy acetone diethyl mercaptal. The 1,3-diglycerides were obtained by hydrogenation of the ketone group. Allyl tetrahydropyranyl ether was oxidized to 1-tetra-hydropyranyl glycerol which was acetylated and interesterified with methyl esters of fatty acids to produce 1,3-diglycerides.

Effects of glucose on palmitate esterification by isolated rat diaphragms

1961 ◽  
Vol 200 (5) ◽  
pp. 1047-1050 ◽  
Author(s):  
Irving B. Fritz ◽  
Eli Kaplan
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Neutral Lipids ◽  
Acid Oxidation ◽  
Glyceride Synthesis ◽  
Sites Of Action ◽  
Palmitate Metabolism ◽  
Isolated Rat ◽  
Stimulation Of

The uptake of palmitate -1-C14 and its conversion to various products by hemidiaphragm preparations incubated for 2 hours was measured in the presence and absence of added glucose or insulin. Following glucose and insulin addition, oxidation of palmitate to CO2 by muscle obtained from either fed or starved rats was decreased, and incorporation of palmitate into neutral lipids freed of unesterified fatty acids was enhanced. The data indicate that the glucose sparing action on fatty acid oxidation by isolated muscle is related to stimulation of glyceride synthesis. Insulin alone was without effect on palmitate metabolism, but insulin addition in the presence of glucose accentuated the glucose sparing action. The data are discussed in relation to the overall effects of glucose on lipid metabolism in vivo, and possible sites of action of glucose on the stimulation of net glyceride synthesis are considered.

Sign in / Sign up

Export Citation Format

Share Document