- Maternal obesity results in decreased syncytiotrophoblast synthesis of palmitoleic acid, a fatty acid with anti-inflammatory and insulin-sensitizing properties
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The fetus is dependent on delivery of fatty acids (FAs) by the syncytiotrophoblast, the transporting epithelium of the human placenta. Obese pregnant women have dyslipidemia; however, whether obesity impacts placental lipid transport and metabolism remains to be fully established. Palmitoleic acid (POA), an FA with antiinflammatory and insulin-sensitizing properties, is synthesized from palmitic acid (PA) catalyzed by stearoyl-coenzyme A desaturase (SCD) activity. We hypothesized that the uptake and incorporation of FAs and POA synthesis are reduced in primary human trophoblasts (PHTs) isolated from pregnancies complicated by maternal obesity. Villous cytotrophoblasts were isolated from 7 placentas of obese [body mass index (BMI) = 37.5 ± 1.9] and 12 normal (BMI = 23.6 ± 0.6) mothers. FA uptake and incorporation were assessed using uniformly labeled (U[13C])–FA mixtures of PA, oleic acid (OA), linoleic acid, and docosahexaenoic acid. Cellular [13C] FAs were quantified both in total cellular lipids and in lipid classes by GC-MS. Uptake and incorporation of [13C] FAs in total cellular lipids were not different in PHTs isolated from obese mothers compared with normal mothers. Only the concentration of OA was increased in the triglyceride fraction (P 13C]-PA treatment, demonstrating SCD activity in PHT cells. Labeled POA content and the POA:PA ratio were significantly lower in PHTs isolated from placentas of obese mothers compared with normal, healthy controls. Decreased syncytiotrophoblast POA synthesis may contribute to insulin resistance and low-grade inflammation in the mother, placenta, or fetus (or a combination of the 3) in pregnancies complicated by obesity.—Ferchaud-Roucher, V., Barner, K., Jansson, T., Powell, T. L. Maternal obesity results in decreased syncytiotrophoblast synthesis of palmitoleic acid, a fatty acid with anti-inflammatory and insulin-sensitizing properties. FASEB J. 33, 6643–6654 (2019). www.fasebj.org.
- Barner, Kelsey,Ferchaud-Roucher, Véronique,Jansson, Thomas,Powell, Theresa L.
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p. 6643 - 6654
(2020/02/28)
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- N-Acylated amino acid methyl esters from marine Roseobacter group bacteria
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Bacteria of the Roseobacter group (Rhodobacteraceae) are important members of many marine ecosystems. Similar to other Gram-negative bacteria many roseobacters produce N-acylhomoserine lactones (AHLs) for communication by quorum sensing systems. AHLs regulate different traits like cell differentiation or antibiotic production. Related N-acylalanine methyl esters (NAMEs) have been reported as well, but so far only from Roseovarius tolerans EL-164. While screening various roseobacters isolated from macroalgae we encountered four strains, Roseovarius sp. D12_1.68, Loktanella sp. F13, F14 and D3 that produced new derivatives and analogs of NAMEs, namely N-acyl-2-aminobutyric acid methyl esters (NABME), N-acylglycine methyl esters (NAGME), N-acylvaline methyl esters (NAVME), as well as for the first time a methyl-branched NAME, N-(13-methyltetradecanoyl)alanine methyl ester. These compounds were detected by GC–MS analysis, and structural proposals were derived from the mass spectra and by derivatization. Verification of compound structures was performed by synthesis. NABMEs, NAVMEs and NAGMEs are produced in low amounts only, making mass spectrometry the method of choice for their detection. The analysis of both EI and ESI mass spectra revealed fragmentation patterns helpful for the detection of similar compounds derived from other amino acids. Some of these compounds showed antimicrobial activity. The structural similarity of N-acylated amino acid methyl esters and similar lipophilicity to AHLs might indicate a yet unknown function as signalling compounds in the ecology of these bacteria, although their singular occurrence is in strong contrast to the common occurrence of AHLs. Obviously the structural motif is not restricted to Roseovarius spp. and occurs also in other genera.
- Bruns, Hilke,Ziesche, Lisa,Taniwal, Nargis Khakin,Wolter, Laura,Brinkhoff, Thorsten,Herrmann, Jennifer,Müller, Rolf,Schulz, Stefan
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p. 2964 - 2973
(2018/12/13)
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- Synthesis and Characterization of Novel Acyl-Glycine Inhibitors of GlyT2
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It has been demonstrated previously that the endogenous compound N-arachidonyl-glycine inhibits the glycine transporter GlyT2, stimulates glycinergic neurotransmission, and provides analgesia in animal models of neuropathic and inflammatory pain. However, it is a relatively weak inhibitor with an IC50 of 9 μM and is subject to oxidation via cyclooxygenase, limiting its therapeutic value. In this paper we describe the synthesis and testing of a novel series of monounsaturated C18 and C16 acyl-glycine molecules as inhibitors of the glycine transporter GlyT2. We demonstrate that they are up to 28 fold more potent that N-arachidonyl-glycine with no activity at the closely related GlyT1 transporter at concentrations up to 30 μM. This novel class of compounds show considerable promise as a first generation of GlyT2 transport inhibitors.
- Mostyn, Shannon N.,Carland, Jane E.,Shimmon, Susan,Ryan, Renae M.,Rawling, Tristan,Vandenberg, Robert J.
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p. 1949 - 1959
(2017/09/26)
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- PROCEDURE FOR THE OBTAINMENT OF FATTY ACIDS OF PHARMACOLOGICAL AND NUTRITIONAL INTEREST
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This invention refers to a procedure for obtaining fatty acids of pharmacological and nutritional interest that comprises the steps of feeding a gas comprising CO2 into a reactor that contains a culture that comprises at least one species of microalgae capable of photosynthesis, the process of photosynthesis by the species of microalgae from the CO2 supplied, producing a biomass that contains a general formula (I) compound: extraction of the general formula (I) compound from the biomass obtained and concentration and/or purification of this compound.
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Paragraph 0161-0170
(2013/08/14)
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- ESTERAMINES AND DERIVATIVES FROM NATURAL OIL METATHESIS
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Esteramine compositions and their derivatives are disclosed. The esteramines comprise a reaction product of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with a tertiary alkanolamine. Derivatives made by quaternizing, sulfonating, alkoxylating, sulfating, and/or sulfitating the esteramines are also disclosed. In one aspect, the ester derivative of the C10-C17 monounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin. The esteramines and derivatives are valuable for a wide variety of end uses, including cleaners, fabric treatment, hair conditioning, personal care (liquid cleansing products, conditioning bars, oral care products), antimicrobial compositions, agricultural uses, and oil field applications.
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Page/Page column 25-26
(2012/05/20)
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- Purification and characterization of OleA from Xanthomonas campestris and demonstration of a non-decarboxylative claisen condensation reaction
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OleA catalyzes the condensation of fatty acyl groups in the first step of bacterial long-chain olefin biosynthesis, but the mechanism of the condensation reaction is controversial. In this study, OleA from Xanthomonas campestris was expressed in Escherichia coli and purified to homogeneity. The purified protein was shown to be active with fatty acyl-CoA substrates that ranged from C 8 to C16 in length. With limiting myristoyl-CoA (C 14), 1 mol of the free coenzyme A was released/mol of myristoyl-CoA consumed. Using [14C]myristoyl-CoA, the other products were identified as myristic acid, 2-myristoylmyristic acid, and 14-heptacosanone. 2-Myristoylmyristic acid was indicated to be the physiologically relevant product of OleA in several ways. First, 2-myristoylmyristic acid was the major condensed product in short incubations, but over time, it decreased with the concomitant increase of 14-heptacosanone. Second, synthetic 2-myristoylmyristic acid showed similar decarboxylation kinetics in the absence of OleA. Third, 2-myristoylmyristic acid was shown to be reactive with purified OleC and OleD to generate the olefin 14-heptacosene, a product seen in previous in vivo studies. The decarboxylation product, 14-heptacosanone, did not react with OleC and OleD to produce any demonstrable product. Substantial hydrolysis of fatty acyl-CoA substrates to the corresponding fatty acids was observed, but it is currently unclear if this occurs in vivo. In total, these data are consistent with OleA catalyzing a non-decarboxylative Claisen condensation reactionin the first step of the olefin biosynthetic pathway previously found to be presentin at least 70 different bacterial strains.
- Frias, Janice A.,Richman, Jack E.,Erickson, Jasmine S.,Wackett, Lawrence P.
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experimental part
p. 10930 - 10938
(2012/03/26)
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- Method of producing dicarboxylic acids
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A method of producing dicarboxylic acids (e.g., α,ω dicarboxylic acids) by reacting a compound having a terminal COOH (e.g., unsaturated fatty acid such as oleic acid) and containing at least one carbon-carbon double bond with a second generation Grubbs catalyst in the absence of solvent to produce dicarboxylic acids. The method is conducted in an inert atmosphere (e.g., argon, nitrogen). The process also works well with mixed unsaturated fatty acids obtained from soybean, rapeseed, tall, and linseed oils.
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Page/Page column 11; 13; 17-18
(2009/05/29)
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- Fatty acid desaturation and elongation reactions of trichoderma sp. 1-OH-2-3
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The fatty acid desaturation and elongation reactions catalyzed by Trichoderma sp. 1-OH-2-3 were investigated. This strain converted palmitic acid (16:0) mainly to stearic acid (18:0), and further to oleic acid (c9-18:1), linoleic acid (c9,c12-18:2), and α-linolenic acid (c9,c12,c15-18:3) through elongation, and Δ9, Δ12, and Δ15 desaturation reactions, respectively. Palmitoleic acid (c9-16:1) and cis-9,cis-12- hexadecadienoic acid were also produced from 16:0 by the strain. This strain converted n-tridecanoic acid (13:0) to cis-9-heptadecenoic acid and further to cis-9,cis-12-heptadecadienoic acid through elongation, and Δ9 and Δ12 desaturation reactions, respectively. trans-Vaccenic acid (t11-18:1) and trans-12-octadecenoic acid (t12-18:1) were desaturated by the strain through Δ9 desaturation. The products derived from t11-18:1 were identified as the conjugated linoleic acids (CLAs) of cis-9,trans-11-octadecadienoic acid and trans-9,trans-11-octadecadienoic acid. The product derived from t12-18:1 was identified as cis-9,trans-12-octadecadienoic acid. cis-6,cis-9-Octadecadienoic acid was desaturated to cis-6,cis-9,cis-12-octadecatrienoic acid by this strain through Δ12 desaturation. The broad substrate specificity of the elongation, and Δ9 and Δ12 desaturation reactions of the strain is useful for fatty acid biotransformation.
- Ando, Akinori,Ogawa, Jun,Kishino, Shigenobu,Ito, Taiyo,Shirasaka, Norifumi,Sakuradani, Eiji,Yokozeki, Kenzo,Shimizu, Sakayu
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experimental part
p. 227 - 233
(2010/06/16)
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- Method for preparing unsaturated fatty acids
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Disclosed relates to a method for preparing unsaturated fatty acids and, more particularly, to a method for preparing unsaturated fatty acids in a high purity of at least 99% by isolating and purifying unsaturated fatty acids via a secondary nucleation mechanism using fatty acid-urea inclusion compounds.
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Page/Page column 3; Sheet 2
(2008/06/13)
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- Process
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A process for producing a conjugated di- or poly-unsaturated fatty acid having from 12 to 24 carbon atoms, or a salt or ester thereof, comprises reacting a non-conjugated free fatty acid, or a salt or ester thereof with a base in the presence of a solvent comprising a monohydric alcohol having from 1 to 6 carbon atoms, wherein the reaction is carried out at a temperature of from 120° C. to 200° C. in the presence of water in an amount of at least 4% by weight based on alcohol.
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Page/Page column 4-5
(2008/06/13)
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- New eudesmane derivatives from Melampodium camphoratum from the suriname rainforest
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Bioassay-guided fractionation of an EtOAc extract of the leaves of Melampodium camphoratum using an assay for inhibitors of the degradation of hemin resulted in the isolation of six new eudesmane sesquiterpenes (1-6) and the known 6-epi-β-verbesinol coumarate (7). The structures of compounds 1-6 were established as 6α-(4′-O-methyl-7′E-coumaryloxy)eudesm- 4(14)-ene (1), 6α-({4′-O-stearyl}-7′E-coumaryloxy)eudesm-4(14) -ene (2), 6α-({4′-O-palmityl}-7′E-coumaryloxy)eudesm-4(14)-ene (3), 6α-({4′-O-[9″Z-hexadecenoyl]}-7′E-coumaryloxy) eudesm-4(14)-ene (4), 6α-(7′Z-coumaryloxy)eudesm-4(14)-ene (5), and 6α-({4′-acetoxy}-7′Z-coumaryloxy)eudesm-4(14)-ene (6). Compounds 1-4 showed weak activity in the hemin degradation assay, while compounds 5-7 were inactive.
- Chaturvedula, V. S. Prakash,Farooq, Afgan,Schilling, Jennifer K.,Malone,Derveld, Iwan,Werkhoven, Marga C. M.,Wisse, Jan H.,Ratsimbason, Michel,Kingston, David G. I.
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p. 2053 - 2057
(2008/04/18)
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- HIGHLY CHEMO-,REGIO-,and STEREOSELECTIVE INTRODUCTION OF A CIS-DOUBLE BOND INTO A THIA-ANALOGUE OF STEARIC ACID
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Replacement of a methylene group by a sulfur atom at the 5-position of stearic acid does not prevent the introduction of a cis-double bond at the 9-,10-positions.
- Buist, Peter H.,Dallmann, Garry H.,Rymerson, Robert T.,Siegel, Peter M.
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p. 857 - 860
(2007/10/02)
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- Phosphonium Iodide in Organic Synthesis
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Phosphonium iodide is found useful in the stereospecific conversion of some vicinal diols to olefins.Synthesis of cis-hexadec-9-enolide has been achieved.
- Chatterjea, J. N.,Majee, R. N.,Mukherjee, S. N.
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p. 733 - 735
(2007/10/02)
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- Unsaturated fatty acid hydrazides
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Mono- or poly-unsaturated fatty acid hydrazides, e.g. cis,-9-octadecenoic acid, 2-(o-methylphenyl)-hydrazide are useful as pharmaceutical agents and are obtainable by reacting a derivative, e.g. mixed anhydride, of a long chain unsaturated carboxylic acid with an appropriate hydrazine compound.
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