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At least 883 records · Page 49Linked to original sources
PubMed1979

Interfacial structure and lipase action. Characterization of taurodeoxycholate-didecanoylglycerol monolayers by physical and kinetic methods.

Surface pressure-area isotherms for 1,3-didecanoyl-glycerol (dicaprin) were determined as a function of the concentration of taurodeoxycholate in the subphase. Analysis of these curves indicates that, from 0.05 to 0.80 mM bile salt, surface structure is dependent only on the surface concentration of the diglyceride. The limiting areas for dicaprin in the presence and absence of bile salt were about 38 A2/molecule. Subjecting the monolayers to hydrolysis by pancreatic lipase yielded kinetic data which, together with the physical studies, support a model for monolayer glyceride molecules undergoing discrete changes of state. In the absence of bile salt, the relatively expanded state exhibits an area of 75 A2/diglyceride molecule and is not a substrate for pancreatic lipase B. The more condensed state exhibits an area of 38 A2/diglyceride molecule and is hydrolyzed at a rate proportional to its concentration in the monolayer. Taurodeoxybholate at 0.05 to 0.60 mM shifts the apparent area of the expanded state to 360 A2/diglyceride molecule.

Animals↗
PubMed1984

Analysis of membrane and cytosolic phorbol ester receptors.

Specific phorbol ester receptors are found in the particulate fraction of cells. In addition, cytosol contains a phorbol ester apo-receptor, which requires phospholipids for reconstitution. The apo-receptor corresponds to protein kinase C, and the quantitatively major membrane receptor appears to be a protein kinase C-phospholipid complex. The ability to reconstitute the phorbol ester apo-receptor into different lipid domains now makes it possible to begin elucidation of the role of the lipid domain in phorbol ester action. Studies reviewed here indicate that diglycerides competitively inhibit phorbol ester binding, consistent with their being the postulated endogenous phorbol ester analogues. Highly lipophilic phorbol esters inhibit effectively only if they are incorporated into the lipid phase, indicating that it is the membrane-dissolved form of the ligand which is recognized. The binding affinity of 3H-phorbol 12,13-dibutyrate for holo-receptor depends markedly (greater than 20-fold range) on the phospholipid environment, and heterogeneous phorbol ester binding (i.e., curved Scatchard plots) can be generated by use of heterogeneous lipid environments in the reconstitution. The possible existence of other phorbol ester receptors in addition to protein kinase C-phospholipid complexes remains to be resolved.

Animals↗
PubMed1984

Diphosphatidylglycerol in experimental acute alveolar injury in the dog.

Acute alveolar injury closely resembling that seen in humans was induced in dogs by subcutaneous injection of N-nitroso-N-methylurethane. Necrosis of alveolar epithelial cells was observed during early injury. Proliferation of immature epithelial cells which began during early injury and became massive after peak injury was followed by their differentiation to mature type II cells during recovery. Quantities of diphosphatidylglycerol (DPG) and of phosphatidylglycerol (PG) in alveolar lavage and in post-lavage lung tissue were measured. An increase in tissue DPG coincided with a sharp decrease in tissue and lavage PG during early injury. DPG was not detectable in the lavage. During late recovery, tissue DPG increased threefold over controls. This increase was accompanied by persistence of a 50% decrease in tissue PG and 83% decrease in lavage PG. Biosynthesis of DPG and PG in isolated lung mitochondria demonstrated that DPG was formed from PG in the presence of CDP-diglyceride. These findings suggest that the low level of PG in the surfactant complex during acute alveolar injury is due to increased turnover of PG to DPG in the lung.

Animals↗
PubMed1983

Changes in nervous system glycolipids during metamorphosis of Xenopus laevis.

Qualitative and quantitative changes occurring in the myelin marker glycolipids, cerebrosides, sulfatides, and monogalactosyl diglyceride, in the nervous system (brain, spinal cord, and tail) of Xenopus laevis during its metamorphic stages were analyzed by normal and reverse-phase high performance liquid chromatography. The concentration of these glycolipids increased rapidly in brain until the tadpole reached the middle of metamorphosis, fluctuated slightly, decreased until metamorphosis was completed, and increased once more as the frog matured. Similar changes were observed in the spinal cord, but the decrease of glycolipids occurred at a later stage of metamorphosis. The glycolipid level in tail nerve reached a peak at the beginning of metamorphosis and then rapidly decreased. The ratios of hydroxycerebroside and hydroxysulfatide to respective nonhydroxylipids in brain, spinal cord, and tail remained constant throughout the metamorphic change but differed in each tissue. The tail contained the highest ratio. The glycolipids in sciatic nerve generated during the metamorphosis had an even higher hydroxyl lipid/nonhydroxy lipid ratio. The cerebrosides contained extremely high concentrations of monounsaturated fatty acids with very long carbon chains (C22-C25) and this homolog composition remained almost unchanged throughout metamorphosis. These results indicate that active degradation of these glycolipids, and probably of myelin, occurs but the glycolipid composition of myelin appears to remain the same throughout the metamorphic process. The significance of these findings is discussed from a morphological standpoint.

Animals↗
PubMed1983

Molecular species of diacylphosphatidylethanolamine in rat and mouse heart given the same diet.

Diacylphosphatidylethanolamine (PE) was isolated from mouse and rat heart given the same standard diet. The molecular species of PE were determined after conversion of PE into diglycerides by means of hydrolysis with phospholipase C, subsequent hydrolysis with pancreatic lipase and separation of the products by argentation TLC and capillary gaschromatography. Docosahexaenoic acid (22:6n3) containing molecular species and arachidonic acid (20:4n6) containing molecular species represented the major fractions. A preference for stearic acid to combine with poly-unsaturated fatty acids was found. Despite an abundant presence of linoleic acid (18:2n6) in the diet, molecular species containing this fatty acid represented only a minor fraction. The possible physico-chemical and physiological meaning of the presence of molecular species containing many double bonds is discussed.

Animals↗
PubMed1982

Increased incorporation of 14C-palmitate into tissue lipids by isolated heart myocytes in endotoxic shock.

The incorporation of 14C-palmitate into various classes of tissue lipids by isolated adult dog heart myocytes was studied in an attempt to understand the pathophysiology of myocardial dysfunction during endotoxic shock. The results showed that the incorporation of 14C-palmitate into phospholipids was increased by 85.3% and 108.8% at 0.5 hours and two hours, respectively, following endotoxin (0.5 mg Escherichia coli lipopolysaccharide B per kg body weight) administration. Incorporation of radioactive palmitate into triglycerides was increased by 50.9% and 107.2% at 0.5 and two hours, respectively, postendotoxin. Incorporation of 14C-palmitate into diglycerides was stimulated by 51.9% and 64.5% at 0.5 and two hours, respectively, after endotoxin injection. The incorporation of 14C-palmitate into tissue-free fatty acids and unaltered at 0.5 hours but it was increased by 211.7% at two hours postendotoxin. These data demonstrated that myocardial membrane lipid profile was greatly altered by increased incorporation of 14C-palmitate into phospholipids and neutral lipids after endotoxin administration. An alteration in myocardial lipid profile, as reported in this study, may contribute to the development of myocardial dysfunction during shock.

Acyl Coenzyme A↗
PubMed1982

The influence of CDP-choline on brain lipid metabolism during ischemia.

The intraperitoneal administration of CDP-choline to gerbils (Meriones unguiculatus) partially prevented the changes of lipid metabolism found in brain after ischemia due to carotid occlusion. The increase of diglyceride pool and of its content of radioactivity, due to arachidonate labelling, was almost completely corrected by the treatment. The increase of the free fatty acids, due to ischemia, was unaltered. The decrease of the phosphatidylcholine labelling due to ischemia was partially corrected by the administered CDP-choline.

Animals↗
PubMedDate not supplied

The effect of transient ischemia on fatty acid and lipid metabolism in the gerbil brain.

Brain ischemia was produced in gerbils by contemporary occlusion of both carotid arteries. Definite changes of the energy state in brain demonstrated that carotid occlusion was effective. At short time intervals from occlusion the free fatty acid content, their distribution, and their concentration and specific activity in arachidonate were determined in brain. A noticeable increase of the arachidonate pool and that of other free fatty acids was detected at very early times from occlusion. Specific activity by arachidonate increased after 30-60 seconds from ligation. By examining arachidonate distribution and specific activity in neutral and polar lipids of brain, it is concluded that phosphatidylcholine and phosphatidylinositol represent the more important source for the release of arachidonate during ischemia. Enzymic-mediated phenomena produced free arachidonate from lipids by a mechanism yielding diglycerides further transformed into fatty acids and by lipid degradation through phospholipase A activity.

Animals↗
PubMed1994

Hepatic phosphatidylcholines: evidence for synthesis in the rat by extensive reutilization of endogenous acylglycerides.

Studies were performed to compare the extent of fatty acid incorporation into liver phosphatidylcholines (PCs) by acyl remodeling and by de novo synthesis. To this end, isolated rat livers were first perfused with palmitoleic acid (16:1) and [2-3H]glycerol and then with 17:1 fatty acid and nonradiolabeled glycerol that resulted in the formation of new molecular species of radiolabeled PCs containing 16:1 and 17:1 acyl groups. The specific activities of newly formed molecular species of the de novo precursors of acylglyceride synthesis, phosphatidic acids (PAs) and diglycerides (DGs), and the products of synthesis, PCs and triglycerides (TGs), were measured at periods during both the labeling period of perfusion with 16:1 (first 15 min) and the more prolonged chase period with 17:1 (up to 120 min). At the end of the labeling period, the specific activity of all the 16:1-containing PAs, DGs, and 16:1-16:1-16:1 and 16:1-16:1-18:2 TGs were the same and were much higher than any molecular species that did not contain 16:1. The specific activities of these molecular species are indicative of the specific activity of molecular species synthesized exclusively by de novo synthesis (i.e., by acylation of glycerol 3-phosphate) during the labeling period. In contrast, the specific activity of 16:1-16:1 PC was only 2/3 that of the other 16:1-16:1 glycerides, and the specific activities of the other 16:1-containing PCs were only about 1/3 that of the corresponding 16:1-containing PAs, DGs, and 16:1-16:1 TGs. After the labeling period and during the chase period with perfusion of 17:1 and nonradiolabeled glycerol, the specific activities of major 16:1 PCs exceeded the specific activities of their corresponding PAs and DGs and remained considerably higher than these precursors of de novo synthesis for the duration of perfusions. However, during this period, the specific activities of major 16:1 PCs were less than their corresponding molecular species of TGs. During the chase period, new 17:1 molecular species of PCs were formed that were also radiolabeled. The specific activity of 16:1-17:1 PC, the 17:1 PC with the highest specific activity, always exceeded its corresponding PA and DG precursors. During the chase period, non-16:1 and non-17:1 molecular species of PCs that comprised the bulk of hepatic PCs were also radiolabeled and the specific activities of these molecular species progressively increased during this period.(ABSTRACT TRUNCATED AT 400 WORDS)

Acylation↗
PubMed1994

Polyphosphoinositide-derived diacylglycerol stimulates the hydrolysis of phosphatidylcholine by phospholipase C during exocytosis of the ram sperm acrosome. Effect is not mediated by protein kinase C.

In ram spermatozoa, treatment with the ionophore A23187 and Ca2+ led to an increase in total diacylglycerol mass and to exocytosis of the acrosomal granule. If sperm cells were prelabeled with [3H]palmitic acid, stimulation with A23187/Ca2+ resulted in the generation of [3H]diacylglycerols with a mixture of saturated and unsaturated fatty acids. When cells were prelabeled with 1-O-[3H]octadecylglycerophosphocholine, stimulation led to the generation of [3H]alkylacylglycerol. No rise in [3H]diacyl- or [3H]alkylacylphosphatidic acid was detected under these conditions. Moreover, no changes in the mass of phosphatidic acid have been previously noted under similar conditions. Thus, these results indicate that diradylglycerols are generated via phospholipase C (PLC). Increases in diradylglycerols were paralleled by rises in monoacyl- or monoalkylglycerols labeled at position 1, but not in free [3H]palmitic acid or [3H]octadecanol, implying that, unlike somatic cells, spermatozoa catabolize diradylglycerols via a 2-diglyceride lipase. Activation of PLC appears to be effected by phosphoinositide-derived diacylglycerol: exposure to Mg2+, a cation known to inhibit phosphoinositide hydrolysis, resulted in less PLC activity upon stimulation, and addition of exogenous 1,2-diacylglycerols enhanced the enzyme's activity. However, 1,3-diacylglycerol and alkylacylglycerol also stimulated PLC activity, suggesting that the effect is unlikely to be mediated via protein kinase C. Since diradylglycerols are known to be essential in the molecular sequence leading to membrane fusion in mammalian spermatozoa, these results suggest that their generation via PLC constitutes a fundamental event during acrosomal exocytosis in response to physiological agonists.

Acrosome↗
PubMed1993

Transient temporal relationship between 1-oleoyl-2-acetyl-sn-glycerol (OAG)-activated synthesis and hydrolysis of polyphosphoinositides: desensitization of phospholipase C and the inositol lipid kinases upon long-term treatment of ascites cells by exogenous OAG.

In ascites tumor cells, phosphoinositide metabolism can be activated by short-term treatment with exogenously added 1-oleoyl-2-acetyl-sn-glycerol (OAG), which is the membrane-permeable analog of diacylglycerides (DAG). Quiescent cells prelabeled with D-myo-2-[3H]inositol and then stimulated with OAG (20 micrograms/ml of medium) reveal transient increases in the liberation of inositol 1,4-bis- and inositol 1,4,5-trisphosphate with peaks at 30 min, and a sustained accumulation of inositol phosphate 30 min after stimulation. The labeling patterns of the corresponding inositol lipids show transient activity profiles for phosphatidylinositol 4-phosphate (PtdIns(4)P) and phosphatidylinositol 4,5-bisphosphate (PtdIns(4,5)P2), and a sustained high activity level for PtdIns 30 min after OAG treatment. These data demonstrate a temporal relationship between synthesis and phospholipase C (PLC)-induced hydrolysis of these lipids. Simultaneous labeling of the cellular inositol phospholipids with [1-14C]arachidonic acid reveals modest accumulations after OAG stimulation. The relative 3H radioactivity distribution between the lipids and their inositol metabolites show that about 10% of the polyphosphoinositide pools are metabolically active. Long-term culturing of the cells (> 24 h) under OAG supplementation produces significant reductions in the catalytic activities of PLC and the PtdIns and PtdIns(4)P-specific kinases which is paralleled by a reduced radioactive labeling of PtdIns(4)P and PtdIns(4,5)P2 under these conditions. These data suggest that diglycerides affect the phosphoinositide metabolism by controlling PLC and phosphoinositide kinase activities probably via modification of membrane properties, and by functioning as modulator of other events.

1-Phosphatidylinositol 4-Kinase↗
PubMed1994

Bombesin, platelet-derived growth factor, and diacylglycerol induce selective membrane association and down-regulation of protein kinase C isotypes in Swiss 3T3 cells.

Swiss 3T3 cells contain protein kinase C (PKC) isotypes alpha, delta, epsilon and zeta (Olivier, A. R., and Parker, P. J. (1992) J. Cell. Physiol. 152, 240-244). Acute stimulation of quiescent cells with the neuropeptide bombesin decreases the mobility of PKC-delta and PKC-epsilon on SDS-polyacrylamide gels. These slower migrating forms of PKC-delta and PKC-epsilon rapidly (within 1 s) and selectively are found associated with the Triton X-100-soluble membrane fraction. No change in the mobility or distribution of PKC-alpha or PKC-zeta is detected. Long-term treatment of cells with bombesin induces selective membrane association and down-regulation of PKC-delta and PKC-epsilon (decreasing 70 and 65%, respectively). No change in the long-term distribution of PKC-alpha and PKC-zeta was detected. Bombesin did, however, increase PKC-alpha protein levels by 60% compared to control cells. PKC-zeta levels remained unchanged. Both the shift in mobility and down-regulation of PKC-delta and PKC-epsilon were only induced by mitogenic doses of bombesin. The potent mitogen platelet-derived growth factor induced similar effects on the PKC isotypes delta and epsilon. PKC-alpha and PKC-zeta levels were unaffected. Repeated doses of the synthetic diglyceride 1-oleoyl-2-acetyl-sn-glycerol induced PKC-delta and PKC-epsilon down-regulation and stimulated the cells to divide. Again PKC-alpha and PKC-zeta levels were unaffected. These results show a correlation between the membrane association and down-regulation of PKC-delta and PKC-epsilon and the entry of cells into S phase.

3T3 Cells↗
PubMed1993

Signaling properties of CR3 (CD11b/CD18) and CR1 (CD35) in relation to phagocytosis of complement-opsonized particles.

Human neutrophils preincubated with antibodies against complement receptor type 1 (CR1) (anti-CD35) and/or complement receptor type 3 (CR3) (anti-CD11b or anti-CD18) exhibited a reduced ability to engulf complement-opsonized yeast particles, whereas cellular adhesion of these particles was reduced only in the presence of anti-CD35 antibodies. These data support the idea that CR1 primarily promotes the adhesion of particles and CR3 mediates the subsequent engulfment. However, the effects of anti-CR1 and anti-CR3 antibodies on particle-induced diglyceride production correlate with the effects of these antibodies on the cellular uptake of the particles. Hence, it seems reasonable to suggest that CR1 also participates in mediating the signal(s) that induce particle uptake. This idea is further supported by the findings that cross-linking surface-bound anti-CD11b, anti-CD18 as well as anti-CD35 antibodies results in activation of phospholipase D (PLD), a signal closely associated with phagocytosis of complement-opsonized yeast particles in human neutrophils. The signaling property of CR1 was further revealed by the observation that cross-linking of surface-bound anti-CD35 triggered a rapid and transient mobilization of intracellular Ca2+, a signal most likely involved in the phagosome-lysosome fusion that occurs after the uptake of a particle. Pretreatment with PMA, which positively modulates CR-mediated engulfment of particles, was found to potentiate the CR3- and CR1-induced activation of PLD but impair the activation of phospholipase C, giving added support to the idea that PLD activation is the principal signal for the engulfment process. The activation of PLD was also increased by stimulating the cells with anti-CD18 or anti-CD35 antibodies prefixed on Staphylococcus aureus particles, instead of cross-linking cellular-bound antibodies, suggesting that the form of ligand presentation is a critical parameter of phagocytic signaling. Taken together, the present results demonstrate that both CR1 and CR3 can initiate transmembrane signaling in human neutrophils and, in particular, activation of PLD. This activation was also further recognized as an important signal regulating the engulfment of complement-opsonized particles.

Complement System Proteins↗
PubMed1993

Clinical and analytical evaluation of a continuous enzymatic method for measuring pancreatic lipase activity.

We report the evaluation of a new commercial kit for the determination of pancreatic lipase activity. The kit is based on the use of a 1,2-diglyceride as substrate and a specific monoglyceride lipase. The detection step is the continuous colorimetric measurement of hydrogen peroxide produced from glycerol by glycerol kinase, glycerol-3-phosphate oxidase, and peroxidase reactions. The procedure appears to be precise (between-day CV < 9%) and the results show good correlation with those obtained by alternative procedures (vs turbidimetry, r = 0.965; vs ultraviolet absorbance-enzymatic method, r = 0.995; vs Ektachem, r = 0.976; vs immunometry, r = 0.970). However, the method is susceptible to interference by increased concentrations (> 4.5 mmol/L) of serum triglycerides. We estimated the reference interval for healthy adults to be 8-44 U/L. When we evaluated clinical efficacy by using receiver-operating characteristic curves and the overlap index, no significant differences were found between the commercial kit and a common turbidimetric assay for diagnosing patients with acute pancreatitis; both methods performed satisfactorily.

Adult↗
PubMed1997

Alterations in serum phosphatidylcholine fatty acyl species by eicosapentaenoic and docosahexaenoic ethyl esters in patients with severe hypertriglyceridemia.

A new and sensitive method has been developed to analyze the molecular species of glycerophospholipids. This method was used to examine the effects of hypolipidemic intervention with n-3 fatty acids on the serum phosphatidylcholine species in severely hypertriglyceridemic patients. The drug treated group (n = 19) received 4 g/day of an 85% concentrate of the ethyl esters of eicosapentenoic and docosahexaenoic acids for 6 weeks. Control patients (n = 21) received 4 g/day of ethyl esters of corn oil fatty acids. To evaluate the effects of n-3 fatty acids upon serum phosphatidylcholines (PCs), sera from treated and control patients were analyzed before and after 6 weeks of intervention. PCs isolated from sera were digested with phospholipase C to diglycerides, derivatized with 7-methoxycoumarin-3-carbonyl azide, and analyzed by reverse phase high performance liquid chromatography (HPLC) with fluorescence detection. Pre-intervention serum PC species were, in order of decreasing concentration C16:0,18:2, C16:0,18:1, C18:0,18:2, C16:0,20:1, C16:0,22:0, C18:0,20:4, C16:0,16:0, C18:0,18:1, C18:1,18:2, C16:0,20:5, and C18:1,20:5. In the treated patients, mean increases of 300% in C16:0,20:5 and of 160% in C16:0,22:6 species were observed. There were no significant changes in the molecular species of the serum phosphatidylcholines in the group receiving the corn oil ethyl esters. The cumulative relative percentages for each of the individual fatty acids measured by HPLC were comparable to those determined by gas-liquid chromatography (GLC). In the treated group plasma triglycerides were reduced 26%, while they were increased by 7% in the placebo group. Our data showed that incorporation of eicosapentaenoic and docosahexaenoic acid into the serum PCs occurred within 6 weeks primarily in the C16:0,20:5 and C16:0,22:6 species and were usually accompanied by a reduction in plasma triglyceride.

Administration, Oral↗
PubMed1997

Erythromycin A-derived macrolides modify the functional activities of human neutrophils by altering the phospholipase D-phosphatidate phosphohydrolase transduction pathway: L-cladinose is involved both in alterations of neutrophil functions and modulation of this transductional pathway.

All erythromycin A derivatives, irrespective of the size of the lactone ring and the nature of the substituent, inhibit oxidant production by neutrophils and promote their degranulation. We demonstrate in this study that the L-cladinose at position 3 of the lactone ring is a key structure in the modulation of these two neutrophil functions, suggesting that this sugar (alone or combined with a lactone structure) interferes with cell target(s) involved in both oxidant production and exocytosis. Taking roxithromycin as an example of erythromycin A derivatives, we also found that these molecules interfered with the phospholipase D (PLD)-phosphatidate phosphohydrolase pathway in two ways. In nonstimulated neutrophils, roxithromycin and all L-cladinose-bearing molecules activated PLD, as reflected by 1-O-[3H]alkyl-2-acyl-phosphatidyl-ethanol production. In addition, these drugs induced an accumulation of 1-O-[3H]alkyl-2-acyl-phosphatidic acid (PA), but not 1-O-[3H]alkyl-2-acylglycerol. PA accumulation seems to be involved in the induction of exocytosis by macrolides, as the roxithromycin-induced release of granular enzymes was impaired strongly in the presence of ethanol. By contrast, in stimulated neutrophils, roxithromycin inhibited PLD activity and totally impaired 1-O-[3H]alkyl-2-acylglycerol production. The inhibition of diglyceride production by roxithromycin (not its descladinosyl derivative) could explain its inhibitory effect on oxidant production. The relevance of our data to the clinical situation, particularly the anti-inflammatory activity of these drugs, requires further investigation.

Diglycerides↗
PubMed1996

Modulation of colon tumor oncogene expression by cancer patient-derived lipids.

In an effort to understand the role of specific fats on carcinogenesis, we have studied the effects of lipids derived from cancer patients on components associated with the regulation of proliferation. The treatment of tumor cells with patient-derived fats produced increased cell proliferation, as indicated by shorter doubling times. The effects of patient-derived lipids on the expression of ras, c-jun, c-erbB-2, and p53 gene products were examined. The cellular expression of the ras proto-oncogene product was increased in both colon tumor cell lines, following lipid treatment. However, c-jun proto-oncogene expression was elevated in HT-29 cells and appeared unchanged in SK-Co-1 cells after lipid treatment. Treatment of HT-29 tumor cells with patient-derived fats produced an enhancement of the p53 gene product, whereas fat treatment reduced p53 expression in SK-Co-1 tumor cells. Further separation of the patient-derived fats indicated that the amplification of p53 gene expression in HT-29 cells could be achieved primarily by addition of the diacylglycerides fraction. Addition of the purified fatty acids, comprising the diglyceride fraction, indicated that the fatty acids, 16:1, 18:0, and 18:1, induced the most significant increases in p53 expression by HT-29 cells. These alterations caused by cancer patient-derived fats are consistent with the loss of normal growth regulation and may explain the epidemiologic association between certain fats and carcinogenesis.

Adenocarcinoma, Papillary↗
PubMed2000

New Syntheses with Oils and Fats as Renewable Raw Materials for the Chemical Industry.

Oils and fats are the most important renewable raw materials for the chemical industry. Hitherto, industrial oleochemistry has concentrated predominantly on the carboxy functionality of fatty acids but, more recently, modern synthetic methods have been applied extensively to fatty compounds for the selective functionalization of the alkyl chain. Radical, electrophilic, nucleophilic, and pericyclic as well as transition metal catalyzed additions to the C-C double bond of, for example, oleic acid as the prototype of a readily accessible, unsaturated fatty acid have led to a large number of novel fatty compounds from which interesting properties are expected. Functionalization of C-H bonds in the alkyl chain is also feasible with remarkable selectivity. Effective and highly versatile catalysts for the metathesis of esters of unsaturated fatty acids have been developed, which lead to new and interesting omega-unsaturated fatty acids. The epoxidation of unsaturated fatty acids has been developed extensively. Enzymatic reactions allow syntheses with high selectivity and yield of mono- and diglycerides and esters of carbohydrates with a variety of surfactant properties. Regio- and enantioselective microbial hydrations and hydroxylations widen the spectrum of selective reactions. Of considerable significance is that, with the use of gene technology, natural oils and fats have been improved significantly and will be improved still further, insofar as they show a more uniform and often unusual fatty acid spectrum. Numerous fatty acids are now available in a purity which makes them attractive for synthesis and as raw materials for the chemical industry.

Journal Article↗