- SOME PROPERTIES OF DIACYLGLYCEROL ACYLTRANSFERASE IN A PARTCULATE FRACTION FROM MATURING SAFFLOWER SEEDS
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The activity of diacylglycerol acyltransferase of a subcellular particulate fraction from maturing safflower seeds was remarkably stimulated by the addition of 1,2-diacylglycerols which were previously emulsified in a gelatin solution by sonication.Metal ions were inhibitory to the reaction.Deoxycholate and diisopropyl fluorophosphate were the most effective inhibitors.Sulfhydryl groups seemed to be of limited significance in the enzyme.Both 1,2-dioleoyl-sn-glycerol and 2,3-dioleoyl-sn-glycerol were good substrates of diacylglycerol acyltransferase, but the 1,3-isomer did not serve as an acyl acceptor.The enzyme showed broad specificity for synthetic rac-1,2-diacylglycerols containing various fatty acids.However, rac-1,2-diecetylglycerol and rac-1,2-dibutylglycerol, which are soluble in water, were ineffective.The enzyme exhibited no significant specificity for saturated and unsaturated fatty acyl-CoA thioesters as acyl donors.This suggests that the fatty acid composition at the 3-position of the glycerol molecule of safflower triacylglycerols may depend on the composition of the endogenous acyl-CoA pool.Key Word Index - Carthamus tinctorius; Compositae; safflower; seeds; triacylglycerol synthesis; diacylglycerol acyltransferase.
- Ichihara, Ken'ichi,Noda, Manjiro
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Read Online
- Symmetrical cationic triglycerides: An efficient synthesis and application to gene transfer
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Some cationic triglycerides 1Aa-1Cb which have a symmetrical structure were effectively synthesized and formulated into cationic liposomes with the co-lipid dioleoylphosphatidylethanolamine (DOPE) and/or dilauroylphosphatidylcholine (DLPC). The plasmid encoding a luciferase was delivered into CHO cells by using these cationic liposomes. Our symmetrical cationic triglycerides showed high transfection activity when DOPE was used as a co-lipid. Among the symmetrical cationic triglycerides synthesized here, 1Ab and 1Ac, which have an oleoyl group at the 1- and 3-position in the glycerol backbone and also have a relatively long linker connecting the 2-hydroxy group in glycerol with the quaternary ammonium head group, were found to be the most suitable for gene delivery into cells. The transfection activity of the symmetrical cationic triglyceride 1Ab was comparable with that of its asymmetrical congener 6 and several times higher than that of Lipofectin.
- Obika, Satoshi,Yu, Wei,Shimoyama, Atsuko,Uneda, Takeshi,Miyashita, Kazuyuki,Doi, Takefumi,Imanishi, Takeshi
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Read Online
- Triglyceride-mimetic structure-gated prodrug nanoparticles for smart cancer therapy
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Off-target drug release and insufficient drug delivery are the main obstacles for effective anticancer chemotherapy. Prodrug-based self-assembled nanoparticles bioactivated under tumor-specific conditions are one of the effective strategies to achieve on-demand drug release and effective tumor accumulation. Herein, stimuli-activable prodrugs are designed yielding smart tumor delivery by combination of the triglyceride-mimic (TG-mimetic) prodrug structure and disulfide bond. Surprisingly, these prodrugs can self-assemble into uniform nanoparticles (NPs) with a high drug loading (over 40%) and accumulate in tumor sites specifically. The super hydrophobic TG structure can act as a gate that senses lipase to selectively control over NP dissociation and affect the glutathione-triggered prodrug activation. In addition, the impacts of the double bonds in the prodrug NPs on parent drug release and the following cytotoxicity, pharmacokinetics, and antitumor efficiency are further demonstrated. Our findings highlight the promising potential of TG-mimetic structure-gated prodrug nanoparticles for tumor-specific drug delivery.
- Tian, Chutong,Guo, Jingjing,Miao, Yifan,Zheng, Shunzhe,Sun, Bingjun,Sun, Mengchi,Ye, Qing,Liu, Wenxue,Zhou, Shuang,Kamei, Ken-Ichiro,He, Zhonggui,Sun, Jin
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p. 15936 - 15948
(2021/11/18)
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- LIPID PRODRUGS OF PREGNANE NEUROSTEROIDS AND USES THEREOF
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The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, as well as methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.
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Paragraph 00420; 00422
(2020/02/23)
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- LIPID PRODRUGS OF JAK INHIBITORS AND USES THEREOF
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The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, and methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.
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Paragraph 00587; 00589
(2020/09/12)
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- LIPID PRODRUGS OF BTK INHIBITORS AND USES THEREOF
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The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, and methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.
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Paragraph 00405; 00596; 00598
(2020/09/12)
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- LIPID PRODRUGS OF GLUCOCORTICOIDS AND USES THEREOF
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The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, and methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.
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Paragraph 00580; 00582
(2020/09/12)
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- LIPID-CONTROLLED RELEASE COMPOSITIONS
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The disclosure provides a glass syringe or a glass cartridge, containing a lipid-based pre-formulation suitable for refrigerated storage.
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Page/Page column 52-53
(2020/12/11)
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- MODIFIED AMINE LIPIDS
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The disclosure provides ionizable amine lipids and salts thereof (e.g., pharmaceutically acceptable salts thereof) useful for the delivery of biologically active agents, for example delivering biologically active agents to cells to prepare engineered cells. The ionizable amine lipids disclosed herein are useful as ionizable lipids in the formulation of lipid nanoparticle-based compositions.
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Page/Page column 160-161; 288-289
(2020/07/04)
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- Stereospecific synthesis of phosphatidylglycerol using a cyanoethyl phosphoramidite precursor
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Phosphatidylglycerols (PG) are a family of naturally occurring phospholipids that are responsible for critical operations within cells. PG are characterized by an (R) configuration in the diacyl glycerol backbone and an (S) configuration in the phosphoglycerol head group. Herein, we report a synthetic route to provide control over the PG stereocenters as well as control of the acyl chain identity.
- Storch, Judith,Struzik, Zachary J.,Thompson, David H.,Weerts, Ashley N.
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- LYMPHATIC SYSTEM-DIRECTING LIPID PRODRUGS
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The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, as well as methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a provided lipid prodrug or a pharmaceutical composition thereof.
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Paragraph 00547; 00549
(2019/03/17)
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- TRIACYLGLYCEROL OLIGOMERS
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This application relates to triacylglycerol oligomers derived from the metathesis of natural oils. These oligomers are structure controlled dimers and quatrimers, and the effect of saturation, molecular size, and positional isomerization are also described herein.
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Paragraph 0049
(2015/11/27)
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- Glycerolysis of methyl oleate on MgO: Experimental and theoretical study of the reaction selectivity
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The liquid-phase MgO-promoted glycerolysis of methyl oleate, a fatty acid methyl ester (FAME), to give acylglycerol products was studied both, experimentally and by density functional theory (DFT). Catalytic results showed that strongly basic low coordination O2- surface sites participate in kinetically relevant steps of the glycerolysis reaction. Changes in the selectivity toward the different mono- and diglyceride isomers were investigated by varying the reaction conditions. The main product was always α-glyceryl monooleate (α-MG), a monoglyceride with the ester fragment at one of the terminal positions of the glycerol molecule; the β-MG isomer, with the ester substituted at position 2 was obtained in much lower amounts. The molecular modeling of glycerol (Gly) and FAME adsorptions as well as of the glycerolysis reaction was carried out using periodic DFT calculations and a model of stepped MgO surface. Results indicated that FAME was more weakly adsorbed than Gly; the latter adsorbs on a coordinatively unsaturated surface O2- site with O-H bond breaking at position 2 of the Gly molecule, giving therefore a surface β-glyceroxide species. Calculations explained the apparent contradiction between the preferential formation of the α-MG isomer and the energetically favored dissociation of the secondary OH group of Gly that leads to the β-glyceroxide species. They predict that the β-glyceroxide species participates in the pathways conducting to both, α- and β-MG isomers. Synthesis of α-MG occurs by C-O coupling of β-glyceroxide with FAME at one of the two primary OH groups of the β-glyceroxide species. Two transition states (TS) and a tetrahedral intermediate (TI) are involved in both, α-MG and β-MG isomer formation. However, the pathway toward β-MG is limited by the large sterical effects associated to the TI formation. Contrarily, the TI leading to α-MG is relatively easy to form.
- Belelli,Ferretti,Apesteguía,Ferullo,Di Cosimo
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p. 132 - 144
(2015/09/28)
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- An insight into the solvent effect on the positional selectivity of the immobilized lipase from Burkholderia cepacia in 1,3-diolein synthesis
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The solvent effect on the positional selectivity of the immobilized lipase from Burkholderia cepacia in 1,3-diolein synthesis was investigated for the first time. The results indicated that the preferential selectivity to sn-1 hydroxyl of the glycerol molecule over sn-2 hydroxyl was weaker in solvents with higher logP values.
- Bi, Yan-Hong,Wang, Zhao-Yu,Duan, Zhang-Qun,Zhao, Xiang-Jie,Chen, Xiao-Ming,Nie, Ling-Hong
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p. 23122 - 23124
(2015/06/02)
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- Highly efficient solvent-free synthesis of 1,3-diacylglycerols by lipase immobilised on nano-sized magnetite particles
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Recently, 1,3-DAGs (1,3-diacylglycerols) have attracted considerable attention as healthy components of food, oil and pharmaceutical intermediates. Generally, 1,3-DAG is prepared by lipase-mediated catalysis in a solvent free system. However, the system's high reaction temperature (required to reach the reactants' melting point), high substrate concentration and high viscosity severely reduce the lipase's activity, selectivity and recycling efficiency. In this report, MjL (Mucor javanicus lipase) was found to have the best performance in the solvent-free synthesis of 1,3-DAGs of several common commercial lipases. By covalent binding to amino-group-activated NSM (nano-sized magnetite) particles and cross-linking to form an enzyme aggregate coat, MjL's specific activity increased 10-fold, and was able to be reused for 10 cycles with 90% residual activity at 55 °C. 1,3-DAGs of lauric, myristic, palmitic, stearic, oleic and linoleic acid were prepared using the resulting immobilised enzyme, all with yields greater than 90%, and the reaction time was also greatly reduced.
- Meng, Xiao,Xu, Gang,Zhou, Qin-Li,Wu, Jian-Ping,Yang, Li-Rong
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p. 319 - 324
(2013/10/08)
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- 1-O-Alkyl (di)glycerol ethers synthesis from methyl esters and triglycerides by two pathways: Catalytic reductive alkylation and transesterification/reduction
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From available and bio-sourced methyl esters, monoglycerides or oleic sunflower refined oil, the corresponding 1-O-alkyl (di)glycerol ethers were obtained in both high yields and selectivity by two different pathways. With methyl esters, a reductive alkylation with (di)glycerol was realized under 50 bar hydrogen pressure in the presence of 1 mol% of Pd/C and an acid co-catalyst. A second two step procedure was evaluated from methyl esters or triolein and consisted of a first transesterification to the corresponding monoglyceride with a BaO/Al2O3 catalyst, then its reduction to the desired glycerol monoether with a recyclable heterogeneous catalytic system Pd/C and Amberlyst 35 under H2 pressure. In addition, a mechanism for the reaction was also proposed.
- Sutter, Marc,Dayoub, Wissam,Metay, Estelle,Raoul, Yann,Lemaire, Marc
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supporting information
p. 786 - 797
(2013/04/24)
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- Evaluation of Rhizopus oryzae lipase for the determination of regiodistribution in triacylglycerols with medium chain fatty acids
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The nutritional profile and rheological behaviors of lipids is both due to fatty acid composition and regiodistribution on external and internal positions of triacylglycerol. Actual methods for regiodistribution analysis having some restrictions, there is still a need for investigating a safe, simple and environmentally friendly method for the sn-2 position analysis that could especially be used for the analysis of fats containing medium and short chain fatty acids. The objective of this study was to evaluate the 1,3-selectivity and typoselectivity of Rhizopus oryzae lipase in the presence of short/medium chain fatty acids in partial hydrolysis conditions used for regiodistribution analysis. Structured triacylglycerols containing eight-carbon-chain length fatty acids in the sn -2 position were chemically synthesized using DCC/DMAP coupling agent and purification steps by flash-chromatography. The final product showed very high purity and was used as the substrate for 1,3-selectivity evaluation. Typoselectivity was assessed by investigating partial hydrolysis of equimolar blends of homogeneous TAG. This study confirmed the 1,3-selectivity of Rhizopus oryzae lipase in the hydrolysis conditions used, and revealed that this lipase was less influenced by fatty acids chain length than pancreatic lipase. Considering this, Rhizopus oryzae lipase appeared to be a good candidate for regiodistribution analysis of fats containing medium and short chain fatty acids.
- Perignon, Marlene,Lecomte, Jerome,Pina, Michel,Renault, Anne,Simonneau-Deve, Camille,Villeneuve, Pierre
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experimental part
p. 89 - 96
(2012/04/04)
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- Optimization of Candida sp. 99-125 lipase catalyzed esterification for synthesis of monoglyceride and diglyceride in solvent-free system
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Esterification of glycerol and oleic acid catalyzed by lipase Candida sp. 99-125 was carried out to synthesize monoglyceride (MAG) and diglyceride (DAG) in solvent-free system. Beta-cyclodextrin as an assistant was mixed with the lipase powder. Six reaction variables, initial water content (0-14 wt% of the substrate mass), the glycerol/oleic acid molar ratio (1:1-6:1), catalyst load (3-15 wt% of the substrate mass), reaction temperature (30-60 °C), agitator speed (130-250 r/min) and beta-cyclodextrin/lipase mass ratio (0-2) were optimized. The optimal conditions to the synthesis of MAG and DAG were different: the optimal glycerol/oleic acid molar ratio, beta-cyclodextrin/lipase mass ratio, catalyst load and reaction temperature were 6:1, 0, 5%, 50 °C for MAG, and 5:1, 1.5, 10%, 40 °C for DAG, respectively. The optimal water content and agitator speed for both MAG and DAG were 10% and 190 r/min, respectively. Under the optimal conditions, 49.6% MAG and 54.3% DAG were obtained after 8 h and 4 h, respectively, and the maximum of 81.4% MAG plus DAG (28.1% MAG and 53.3% DAG) was obtained after 2 h under the DAG optimal condition. Above 90% purity of MAG and DAG can be obtained by silica column separation.
- Zhao, Yanjun,Liu, Junfeng,Deng, Li,Wang, Fang,Tan, Tianwei
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body text
p. 157 - 162
(2012/07/01)
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- MgO-based catalysts for monoglyceride synthesis from methyl oleate and glycerol: Effect of Li promotion
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The synthesis of monoglycerides (glyceryl monooleates) by heterogeneously catalyzed glycerolysis of an unsaturated fatty acid methyl ester (methyl oleate) was studied on MgO and Li-promoted MgO catalysts. Several MgO-based catalysts with different Li loadings were prepared by incipient wetness impregnation and characterized by XRD, N2 physisorption, and FTIR and TPD of CO 2 among other techniques. Promotion of MgO with lithium, a basic promoter, affected the textural and structural properties of the resulting oxides so that more crystalline MgO phases with decreased surface area were obtained at increasing Li contents. Furthermore, the addition of Li generated new strong base sites because of formation of dispersed surface Li2O species, and thereby increased the total base site density of parent MgO. Li-containing MgO catalysts efficiently promoted the glycerolysis reaction, achieving high monoglyceride yields (70-73%) at 493 K. The initial monoglyceride formation rate increased linearly with the Li content on the sample following the enhanced overall catalyst base strength. Although conversions at the end of the run were ≈100% for all the catalysts, the monoglyceride selectivity slightly decreased with the Li loading, probably as a consequence of the less surface affinity for glycerol adsorption that facilitates competing monoglyceride re-adsorption and transformation to diglycerides by consecutive glycerolysis or disproportionation reactions.
- Ferretti,Apesteguía,Di Cosimo
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experimental part
p. 146 - 153
(2012/02/01)
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- The pronounced effect of water activity on the positional selectivity of Novozym 435 during 1,3-diolein synthesis by esterification
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We have investigated the effect of water activity on the positional selectivity of the immobilized lipase Novozym 435 during the esterification of oleic acid with glycerol for 1,3-diolein preparation. The highest preferential selectivity of Novozym 435 to
- Duan, Zhang-Qun,Du, Wei,Liu, De-Hua
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experimental part
p. 356 - 358
(2010/11/16)
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- Biochemical characterization of the cutinases from Thermobifida fusca
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Thermobifida fusca produces two cutinases which share 93% identity in amino acid sequence. In the present study, we investigated the detailed biochemical properties of T. fusca cutinases for the first time. For a better comparison between bacterial and fungal cutinases, recombinant Fusarium solani pisi cutinase was subjected to the similar analysis. The results showed that both bacterial and fungal cutinases are monomeric proteins in solution. The bacterial cutinases exhibited a broad substrate specificity against plant cutin, synthetic polyesters, insoluble triglycerides, and soluble esters. In addition, the two isoenzymes of T. fusca and the F. solani pisi cutinase are similar in substrate kinetics, the lack of interfacial activation, and metal ion requirements. However, the T. fusca cutinases showed higher stability in the presence of surfactants and organic solvents. Considering the versatile hydrolytic activity, good tolerance to surfactants, superior stability in organic solvents, and thermostability demonstrated by T. fusca cutinases, they may have promising applications in related industries.
- Chen, Sheng,Su, Lingqia,Billig, Susan,Zimmermann, Wolfgang,Chen, Jian,Wu, Jing
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experimental part
p. 121 - 127
(2010/10/19)
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- Study on acyl migration kinetics of partial glycerides: Dependence on temperature and water activity
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Acyl migration phenomenon was often observed during 1,3-positional specificity lipase-catalyzed reactions from triglycerides and partial glycerides, including acyl migration of 1,2-diglyceride (1,2-DG) to 1,3-diglyceride (1,3-DG) and 2-monoglyceride (2-MG) to 1-monoglyceride (1-MG). However, the acyl migration mechanism and kinetics were seldom studied despite of numerous researches on process optimization of 1,3-positional specificity lipase-catalyzed reaction. In this paper, the influence of related factors on acyl migration process as well as their influencing mechanism was further studied. It was found that temperature and water activity were two crucial factors that would influence acyl migration kinetics. Determination of the kinetic parameters under different temperatures revealed that the acyl migration reaction rates were greatly promoted by the increasing of temperature. The acyl migration rates of 1,2-diglyceride and 2-monoglyceride were quite different from each other, which was found to be due to the different activation energies. Further study of how would water influence the acyl migration process showed that water activity rather than water content was a key factor that influenced acyl migration and the acyl migration rate would decrease with the increase of water activity. It was further revealed that water activity influenced the charge dispersion of the transition state, which ultimately influenced the reaction activation energy and then influenced the acyl migration rate.
- Li, Wei,Du, Wei,Li, Qiang,Sun, Ting,Liu, Dehua
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scheme or table
p. 17 - 22
(2010/10/19)
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- Enzymatic synthesis of monoglycerides by esterification reaction using Penicillium camembertii lipase immobilized on epoxy SiO2-PVA composite
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Glycerol-fatty acid esterification has been conducted with lipase from Penicillium camembertii lipase immobilized on epoxy SiO2-PVA in solvent-free media, with the major product being 1-monoglyceride, a useful food emulsifier. For a given set of initial conditions, the influence of reaction was measured in terms of product formation and selectivity using different fatty acids as acyl donors. Results were found to be relatively dependent of the chain length of the fatty acids, showing high specificity for both myristic and palmytic acids attaining final mixture that fulfills the requirements established by the World Health Organization to be used as food emulsifiers.
- Freitas, Larissa,Paula, Ariela V.,dos Santos, Julio C.,Zanin, Gisella M.,de Castro, Heizir F.
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experimental part
p. 87 - 90
(2010/10/19)
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- Characterization of lipases and esterases from metagenomes for lipid modification
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Three hundred and fifty novel lipases and esterases discovered from environmental DNA samples were characterized for their fatty acid profile using GC-analysis. Enzymes were selected for further study based on activity and fatty acid chain length specificity. Additional characterization was based on enzyme activity towards tributyrin and 4-methylumbelliferyl butyrate, and enzyme heat stability. Several lipases were identified, which show high specificity towards short-chain fatty acids similar to pregastric lipases from kid and calf and a lipase from Mucor javanicus. Additionally, the metagenome-derived enzymes were thermostable. Selected metagenomic lipases were immobilized on Celite and used for the synthesis of structured triglycerides.
- Bertram, Mark,Hildebrandt, Petra,Weiner, David P.,Patel, Jesal S.,Bartnek, Flash,Hitchman, Timothy S.,Bornscheuer, Uwe T.
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- GALACTOSE DERIVATIVE, DRUG CARRIER AND MEDICINAL COMPOSITION
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The object of the invention is to provide a novel and useful galactose derivative constituting a drug carrier by which a medicine can be efficiently transferred into the liver, a drug carrier comprising the derivative, and a pharmaceutical composition comprising the carrier and a medicine. The present invention relates to a galactose derivative made up of galactose, a suitable spacer and a certain lipid, a drug carrier comprising the derivative and a cationic lipid, and a pharmaceutical composition comprising the carrier and a medicine (preferably a double strand RNA, a double strand DNA, an oligo nucleic acid) .
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Page/Page column 19
(2010/11/27)
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- Therapeutic use of acyl glycerols and the nitrogen- and sulphur- containing analogues thereof
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The invention relates to the use of acyl glycerols and the nitrogen- and sulfur-containing analogues thereof in the therapeutic field, particularly in human health. The inventive compounds have advantageous pharmacological properties and are particularly of use for the prevention or treatment of neurodegenerative diseases.
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Page/Page column 29-30
(2008/06/13)
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- Therapeutic use of of acyglycerols and the nitrogen-and sulphur-containing analogues thereof
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The invention relates to the use of acylglycerols and the nitrogen- and sulfur-containing analogues thereof in therapy, particularly for the treatment of cerebral ischemia. The invention further relates to methods for preparing said derivatives, novel compounds, in particular acylglycerols, the nitrogen- and sulfur-containing analogues thereof and methods for preparing same.
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Page/Page column 14
(2010/11/24)
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- TREATMENT OF NEURODEGENERATIVE CONDITIONS
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A method is provided for treating a patient in need of therapy for a neurodegenerative disease comprising administering to that patient a therapeutically effective dose of a lipid glyceride comprising a glycerol moiety and a fatty acid moiety, the fatty acid moiety being selected from the group consisting of γ-linolenic acid, dihomo-γ-linolenic acid and arachidonic acid characterised in that the selected fatty acid moiety is attached to the glycerol moiety at its sn-2 position. Preferably the method is that wherein the lipid is administered for a duration and at a dose sufficient to maintain or elevate TGF-β1 levels in the patient to therapeutic levels.
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Page/Page column 41
(2008/06/13)
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- An isozyme of earthworm serine proteases acts on hydrolysis of triacylglycerol
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An enzyme catalyzing the hydrolysis of triacylglycerol was purified from an earthworm. The N-terminal amino acid sequence and the catalytic function of the purified enzyme were identical to those of Isozyme C, an isozyme of the earthworm-serine proteases. No other lipase proteins were found in the earthworm cells. The isozyme might act on the hydrolysis of triacylglycerol as well as the protein decomposition.
- Nakajima, Nobuyoshi,Sugimoto, Manabu,Tsuboi, Sadao,Tsuji, Hideaki,Ishihara, Kohji
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p. 2009 - 2011
(2008/02/03)
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- Fatty acid compounds, preparation and uses thereof
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The invention concerns novel molecules, their preparation and their uses, in particular in the field of human and veterinary medicine and cosmetics. The inventive compounds are partly fatty acid derivatives and exhibit advantageous pharmacological and cosmetic properties. The invention also concerns various uses of said compounds, the pharmaceutical compositions containing them and methods for preparing them. The inventive compounds are useful in particular for preventing and/or treating dyslipidemiae, cardiovascular diseases, syndrome X, restenosis, diabetes, obesity, hypertension, certain cancers, dermatological diseases and in cosmetics, for fighting against skin aging and its effects notably against wrinkles and the like
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- Enzymatic synthesis of symmetrical 1,3-diacylglycerols by direct esterification of glycerol in solvent-free system
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1,3-Diacylglycerols were synthesized by direct esterification of glycerol with free fatty acids in a solvent-free system. Free fatty acids with relatively low melting points (45°C) such as unsaturated and medium-chain saturated fatty acids were used. With stoichiometric ratios of the reactants and water removal by evaporation at 3 mm Hg vacuum applied at 1 h and thereafter, the maximal 1,3-diacylglycerol content in the reaction mixture was: 84.6% for 1,3-dicaprylin, 84.4% for 1,3-dicaprin, 74.3% for 1,3-dilinolein, 71.7% for 1,3-dieicosapentaenoin, 67.4% for 1,3-dilaurin, and 61.1% for 1,3-diolein. Some of the system's parameters (temperature, water removal, and molar ratio of the reactants) were optimized for the production of 1,3-dicaprylin, and the maximal yield reached 98%. The product was used for the chemical synthesis of 1,3-dicapryloyl-2-eicosapentaenoylglycerol. The yield after purification was 42%, and the purity of the triacylglycerol was 98% (both 1,3-dicapryloyl-2-eicosapentaenoylglycerol and 1,2-dicapryloyl-3-eicosapentaenoylglycerol included) by gas chromatographic analysis, of which 90% was the desired structured triacylglycerol (1,3-dicapryloyl-2-eicosapentaenoylglycerol) as determined by silver ion high-performance liquid chromatographic analysis.
- Rosu, Roxana,Yasui, Mamoru,Iwasaki, Yugo,Yamane, Tsuneo
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p. 839 - 843
(2007/10/03)
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- Enzyme, medium, and reaction engineering to design a low-cost, selective production method for mono- and dioleoylglycerols
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The selective enzymic production of mono- and diolein (MO, DO) was optimized at high yields. A comparative study of the following distinct enzymic reactions was conducted: ethyl oleate glycerolysis, triolein (TO) glycerolysis, and direct esterification. Solvent-free systems were compared with media that contained different solvents. Native, modified (with polyethylene glycol), and immobilized lipases were used. Mechanical resistance, the support effect on enzyme and glycerol dispersion and on process reproducibility, and hydrophilicity of the support were considered in the process optimization. We report the use of an immobilized lipase on an inorganic support (Celite), which has high activities in both solid-phase glycerolysis (99% reaction conversion) and esterification (100% conversion). The optimum conditions for the distinct reactions were compared by considering their selectivities, conversions, yields, and cost of the substrates. We found less costly and more selective processes in the absence of solvents for glycerolysis of triolein and direct esterification. Although glycerolysis was the most interesting process to produce diolein, esterification was better for monoolein preparation with this biocatalyst. The esterification reaction yielded 93 wt% of MO, in the absence of either TO or oleic acid (OA), at low cost because of the 100% reaction conversion. Similar costs of the substrates (10.6 and 10.1 $/g) were necessary to obtain 67 and 80 wt% of DO in esterification and glycerolysis, respectively. The glycerolysis conversion was 96%. In esterification, the product mixture was impure, with a high amount of residual OA due to the low conversion (59%). The high activity of PSL-Celite in these solid-phase reactions has an advantage over the reactions with nonimmobilized lipases due to the ease of enzyme recovery. The absence of organic solvents reduces the need for solvent removal from the reaction mixtures.
- Arcos,Otero
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p. 673 - 682
(2007/10/03)
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- Enzymatic esterification of glycerol III. Lipase-catalyzed synthesis of regioisomerically pure 1,3-sn-diacylglycerols and 1(3)-rac-monoacylglycerols derived from unsaturated fatty acids
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Lipases that display high regioselectivities and broad substrate tolerance were used as catalysts for the efficient esterification of glycerol under the conditions of irreversible acyl transfer. A variety of unsaturated fatty acids, such as oleic, linoleic, erucic, ricinolic, hydroxystearic and coriolic acid, were used for this purpose in the form of their vinyl esters. Suitable biocatalysts were chosen on the basis of systematic screening experiments regarding their regioselectivities (RE) and substrate tolerances. Distinct differences were found and expressed in numerical RE values as a measure for differences of these biocatalysts as being specific, selective, and nonspecific. Based on these experiments, a variety of molecules were synthesized on a preparative scale (>150 mmol) in good yield (ca. 85%) and with high regioisomerical purities (>95% RE).
- Waldinger,Schneider
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p. 1513 - 1519
(2007/10/03)
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- Synthesis of Mono- and Diglycerides In Water-in-Oil Microemulsions
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Enzyme-Catalyzed esterification was carried out in single-phase, oil-continuous microemulsions.The lipozyme was solubilized, along with glycerol and water, in the aqueous core of water / diethylhexyl sodium sulfosuccinate / hydrocarbon microemulsion system.Upon addition of fatty acid, mono- and diglycerides were formed, due to the esterification reaction taking place at the interface of the droplets in the microemulsion.The initial rate of conversion of oleic acid increases with oil chainlength of the continuous phase whereas final conversion is maximum for hexane.The conversion of stearic acid is 30percent whereas conversion of oleic acid is 70percent.The percent conversion of various fatty acids in the same continuous medium increases with fatty acid chainlength.The oleic acid / glycerol ratio is an important parameter for optimum conversion of oleic acid into glycerides.The yield can be increased by subsequent addition of glycerol after equilibrium is reached.High-performance liquid chromatography analysis of samples from microemulsions showes the presence of mono- and diglycerides.Possible mechanisms for the abovementioned effects are discussed. KEY WORDS: AOT, diglyceride, esterification, fatty acid, glycerol, hydrolysis, lipase, microemulsion, monoglyceride, reversed micelle.
- Singh, C. P.,Shah, D. O.,Holmberg, Krister
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p. 583 - 587
(2007/10/02)
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- A new catalyst for the preparation of oleate of glycerin
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In this investigation sulfate promoted titanium oxide (SPTO) is used to prepare oleate of glycerin, an excellent internal lubricant for manufacturing transparent sheet materials of polyvinylchloride (PVC).Experimental results show that the occasional saponification caused by the conventional sodalye catalyst for preparing oleate of glycerin can be avoided completely.SPTO can be used repeatedly without any special treatment.Its activity is comparable with that of sodalye.Also the use of SPTO can produce the desirable product composition.SPTO is likely to become a new catalyst for the production of oleate of glycerin.
- Rongsheng, Li,Hua, Yang,Wuyang, Zhang,Quan, Wei,Naixiang, Wei
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p. 449 - 451
(2007/10/02)
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