1955-33-5Relevant academic research and scientific papers
Galactolipids from Bauhinia racemosa as a new class of antifilarial agents against human lymphatic filarial parasite, Brugia malayi
Sashidhara, Koneni V.,Singh, Suriya P.,Misra, Sweta,Gupta, Jyoti,Misra-Bhattacharya, Shailja
, p. 230 - 235 (2012)
Bioassay guided fractionation of ethanolic extract of the leaves of Bauhinia racemosa led to the isolation of galactolipid and catechin class of the compounds (1-7) from the most active n-butanol fraction (F4). Among the active galactolipids, 1 emerged as the lead molecule which was active on both forms of lymphatic filarial parasite, Brugia malayi. It was found to be better than the standard drug ivermectin and diethylcarbamazine (DEC) in terms of dose and efficacy.
Linolenic acid-modified PEG-PCL micelles for curcumin delivery
Song, Zhimei,Zhu, Wenxia,Liu, Na,Yang, Fengying,Feng, Runliang
, p. 312 - 321 (2014)
In this study, a novel linolenic acid-modified poly(ethylene glycol)-b-poly(E-caprolactone) copolymer was prepared through radical addition, ring-opening polymerization, and N-acylation reactions. Its structure was characterized by 1H NMR and GPC. Micelles were developed by thin-film hydration and used as a delivery system for curcumin with high drug loading capacity of 12.80% and entrapment efficiency of 98.53%. The water solubility of curcumin was increased to 2.05 mg/mL, which was approximately 1.87 × 105 times higher than that of free curcumin. The micelles were spherical shape with an average diameter of 20.8 ± 0.8 nm. X-ray diffraction and FT-IR studies suggested that curcumin existed in the polymeric matrices under π-π conjugation and hydrogen bond interaction with the copolymer. In vitro drug release studies indicated that the curcumin release from linolenic acid-modified copolymer micelles met controlled release, and its release rate was less than that from the linolenic acid-unmodified copolymer micelles. Cytotoxicities against Hela and A-549cells demonstrated that the additional π-π conjugation could affect curcumin's anticancer activity through reducing its release from micelles. Hemolysis test and intravenous irritation test results revealed that the linolenic acid-modified copolymer was safe for intravenous injection. The plasma AUC0-∞ and MRT0-∞ of curcumin-loaded linolenic acid-conjugated poly(ethylene glycol)-b-poly(E-caprolactone) copolymer micelles were 2.75- and 3.49-fold higher than that of control solution, respectively. The CLz was also decreased by 2.75-fold. So, this linolenic acid-modified copolymer might be a carrier candidate for curcumin delivery.
Three new sucrose fatty acid esters from Equisetum hiemale L.
Cheng, Jin-Tang,Li, Yan,He, Juan,Li, Xing-Yao,Wu, Xing-De,Shao, Li-Dong,Dong, Liao-Bin,Deng, Xu,Gao, Xiu,Peng, Li-Yan,Cheng, Xiao,Zhao, Qin-Shi
, p. 1158 - 1163 (2012)
Three new monosubstituted sucrose fatty acid esters, 1-3, were isolated from Equisetum hiemale L., together with nine known compounds, 4-12. Their structures were elucidated by spectroscopic analyses. Compounds 5, 6, and 10-12 were isolated from the title
Alteration of Chain Length Selectivity of Candida antarctica Lipase A by Semi-Rational Design for the Enrichment of Erucic and Gondoic Fatty Acids
Zorn, Katja,Oroz-Guinea, Isabel,Brundiek, Henrike,D?rr, Mark,Bornscheuer, Uwe T.
, p. 4115 - 4131 (2018/10/02)
Biotechnological strategies using renewable materials as starting substrates are a promising alternative to traditional oleochemical processes for the isolation of different fatty acids. Among them, long chain mono-unsaturated fatty acids are especially interesting in industrial lipid modification, since they are precursors of several economically relevant products, including detergents, plastics and lubricants. Therefore, the aim of this study was to develop an enzymatic method in order to increase the percentage of long chain mono-unsaturated fatty acids from Camelina and Crambe oil ethyl ester derivatives, by using selective lipases. Specifically, the focus was on the enrichment of gondoic (C20:1 cisΔ11) and erucic acid (C22:1 cisΔ13) from Camelina and Crambe oil derivatives, respectively. The pursuit of this goal entailed several steps, including: (i) the choice of a suitable lipase scaffold to serve as a protein engineering template (Candida antarctica lipase A); (ii) the identification of potential amino acid targets to disrupt the binding tunnel at the adequate location; (iii) the design, creation and high-throughput screening of lipase mutant libraries; (iv) the study of the selectivity towards different chain length p-nitrophenyl fatty acid esters of the best hits found, as well as the analysis of the contribution of each amino acid change and the outcome of combining several of the aforementioned residue alterations and, finally, (v) the selection and application of the most promising candidates for the fatty acid enrichment biocatalysis. As a result, enrichment of C22:1 from Crambe ethyl esters was achieved either, in the free fatty acid fraction (wt, 78%) or in the esterified fraction (variants V1, 77%; V9, 78% and V19, 74%). Concerning the enrichment of C20:1 when Camelina oil ethyl esters were used as substrate, the best variant was the single mutant V290W, which doubled its content in the esterified fraction from approximately 15% to 34%. A moderately lower increase was achieved by V9 and its two derived triple mutant variants V19 and V20 (27%). (Figure presented.).
A nine carbon homologating system for skip-conjugated polyenes
Mustafa, Hussein H.,Baird, Mark S.,Al Dulayymi, Juma'A R.,Tverezovskiy, Viacheslav V.
, p. 34 - 42 (2014/07/08)
Ozonolysis of Z,Z,Z-cylonona-1,4,7-triene leads to a 1,9-difunctionalised Z,Z-3,6-nonadiene which is readily converted into a range of polyunsaturated pheromones and fatty acids.
Method of producing dicarboxylic acids
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Page/Page column 11; 13; 17-18, (2009/05/29)
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.
Fatty acid desaturation and elongation reactions of trichoderma sp. 1-OH-2-3
Ando, Akinori,Ogawa, Jun,Kishino, Shigenobu,Ito, Taiyo,Shirasaka, Norifumi,Sakuradani, Eiji,Yokozeki, Kenzo,Shimizu, Sakayu
experimental part, p. 227 - 233 (2010/06/16)
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.
Substrate specificity and regioselectivity of Δ12 and ω3 fatty acid desaturases from Saccharomyces kluyveri
Oura, Takahiro,Kajiwara, Susumu
experimental part, p. 3174 - 3179 (2009/04/07)
Δ12 and ω3 fatty acid desaturases are key enzymes in the synthesis of polyunsaturated fatty acids (PUFAs), which are important constituents of membrane glycerolipids and also precursors to signaling molecules in many organisms. In this study, we determined the substrate specificity and regioselectivity of the Δ12 and ω3 fatty acid desaturases from Saccharomyces kluyveri (Sk-FAD2 and Sk-FAD3). Based on heterologous expression in Saccharomyces cerevisiae, it was found that Sk-FAD2 converted C16-20 monounsaturated fatty acids to diunsaturated fatty acids by the introduction of a second double bond at the ν + 3 position, while Sk-FAD3 recognized the ω3 position of C18 and C20. Furthermore, fatty acid analysis of major phospholipids suggested that Sk-FAD2 and Sk-FAD3 have no strong substrate specificity toward the lipid polar head group or the sn-positions of fatty acyl groups in phospholipids.
Copper compositions and their use as hydrogenation catalysts
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Page/Page column 12, (2008/06/13)
Copper compositions that are useful as hydrogenation catalysts are disclosed. In particular, the copper compounds are catalysts for the selective hydrogenation of oils that contain unsaturated fatty acyl components such as unsaturated vegetable oils. Methods of preparing the copper compositions are also disclosed. Methods of hydrogenating unsaturated compositions that contain at least two sites of unsaturation using the hydrogenation catalysts, along with products obtained from the hydrogenation reactions described herein are also disclosed.
