116745-32-5Relevant academic research and scientific papers
Neomastoidin A, a novel monoacylglycerol with an amino acid moiety from Macrolepiota neomastoidea
Kim, Ki Hyun,Choi, Sang Un,Lee, Kang Ro
, p. 894 - 895 (2009)
A novel monoacylglycerol with an amino acid moiety, neomastoidin A (1), was isolated from the fruiting bodies of the poisonous mushroom Macrolepiota neomastoidea. The structure of 1 was established by extensive spectroscopic analysis and further confirmed
Cytotoxic ent-Abietane-type diterpenoids from the roots of Euphorbia ebracteolata
Han, Chunhui,Peng, Yulin,Wang, Yifei,Huo, Xiaokui,Zhang, Baojing,Li, Dawei,Leng, Aijing,Zhang, Houli,Ma, Xiaochi,Wang, Chao
, p. 93 - 97 (2018)
Euphoroids A–C (1–3), three new ent-abietane-type diterpenoids, together with ten known analogues (4–13) were obtained from the roots of Euphorbia ebracteolata. The structures of these compounds were determined by extensive spectroscopic data analysis, including UV, HRESIMS, 1D-, and 2D-NMR data. The inhibitory effects of compounds 1–13 on human cancer cells were determined using the MTT assay. The results revealed that new compounds 2 and 3 showed moderate cytotoxic activities against human cancer cell lines. Especially, compound 3 displayed selective cytotoxic effect agains cancer cell lines.
Enzyme-based hybrid macroporous foams as highly efficient biocatalysts obtained through integrative chemistry
Brun,Babeau Garcia,Deleuze,Achard,Sanchez,Durand,Oestreicher,Backov
, p. 4555 - 4562 (2010)
Integrative chemistry-based rational design has been used to synthesize the first lipase [C-CRl]@Glymo-Si(HIPE) and [C-TAl]@Glymo-Si(HIPE) hybrid macrocellular biocatalysts, where immobilization of crude enzymes is optimized, while circumventing the reactants' low kinetic diffusion, by the use of silica macroporous hosts. As a direct consequence, these new hybrid biocatalysts display unprecedented cycling catalysis performance, as demonstrated by the syntheses of butyloleate ester (used as biodiesel lubricant), hydrolysis of linoleic-glycero ester derivatives (end products used for detergent and soap generations), and trans-esterification (reaction involved in the synthesis of low viscosity biodiesel). Considering that the catalytic performances are given in terms of absolute conversion percentage and not just relative enzyme activity, the enzyme@Glymo-Si(HIPE) hybrid macrocellular biocatalysts presented in this study display unprecedented high yield cycling catalysis performances, where turnover numbers (TON) and turnover frequencies (TOF) show promise for real industrial applications. This study can be considered as a milestone for enzyme-based heterogeneous catalyzes, thereby enhancing their competitiveness with the supported-catalysts commonly used in industry, in total agreement with current sustainable development issues. Also, the new macrocellular biocatalysts are well-suited for large-scale industrial production because of their above-mentioned performance characteristics, further enhanced by their monolithic character, which eases the separation of the catalysts from other reaction components.
Balanoinvolin, a new steroid derivative from Balanophora involucrate
Luo, Bing,Zou, Kun,Guo, Zhiyong,Dan, Feijun,Wang, Juizhi,Wang, Hui
, p. 371 - 373 (2009)
A new compound, β-sitosterylglucoside-3'-O-linoleate, named balanoinvolin, and three known compounds coniferin, methylconiferin, and 4-O-β-D-glucopyranosylconiferyl aldehyde, were isolated from Balanophora involucrate Hook. f. and their structures were de
Radiosynthesis, in vitro and in vivo evaluation of 123I-labeled anandamide analogues for mapping brain FAAH
wyffels, Leonie,De Bruyne, Sylvie,Blanckaert, Peter,Lambert, Didier M.,De Vos, Filip
, p. 49 - 56 (2009)
Fatty acid amide hydrolase (FAAH) is one of the main enzymes responsible for terminating the signaling of endocannabinoids, including anandamide. This paper is the first report of the synthesis, [123I]-labeling and in vitro and in vivo evaluation of anandamide analogues as potential metabolic trapping radioligands for in vivo evaluation of brain FAAH. N-(2-Iodoethyl)linoleoylamide (2) and N-(2-iodoethyl)arachidonylamide (4) were synthesized with good yields (75% and 86%, respectively) in a two steps procedure starting from their respective acids. In vitro analyses, performed using recombinant rat FAAH and [3H]-anandamide, demonstrated interaction of 2 and 4 with FAAH (IC50 values of 5.78 μM and 3.14 μM, respectively). [123I]-2 and [123I]-4 were synthesized with radiochemical yields of 21% and 12%, respectively, and radiochemical purities were >90%. Biodistribution studies in mice demonstrated brain uptake for both tracers (maximum values of 1.23%ID/g at 3 min pi for [123I]-2 and 0.58%ID/g at 10 min pi for [123I]-4). However, stability studies demonstrated the sensitivity of both tracers to dehalogenation.
Stelleralides D-J and Anti-HIV Daphnane Diterpenes from Stellera chamaejasme
Yan, Min,Lu, Yan,Chen, Chin-Ho,Zhao, Yu,Lee, Kuo-Hsiung,Chen, Dao-Feng
, p. 2712 - 2718 (2015)
Bioassay-guided fractionation of a petroleum ether extract of the roots of Stellera chamaejasme led to the isolation of seven new (stelleralides D-J, 1-7) and 12 known (8-19) daphnane diterpenoids. The structures and relative configurations of 1-7 were established on the basis of extensive spectroscopic analysis, including HRESIMS and comprehensive NMR techniques. All isolates were evaluated for anti-HIV activity in MT4 cells. All compounds tested, except 2, showed anti-HIV activity, and, especially, five 1α-alkyldaphnane diterpenoids (3, 4, 5, 10, and 11) exhibited extremely potent anti-HIV activity, with EC50 values of 0.06-1.1 nM and selectivity index values of more than 10000.
Antiparasitic Ovalicin Derivatives from Pseudallescheria boydii, a Mutualistic Fungus of French Guiana Termites
Elie, Nicolas,Eparvier, Véronique,Grayfer, Tatyana,Grellier, Philippe,Hebra, Téo,Leman-Loubière, Charlotte,Sorres, Jonathan,Stien, Didier,Touboul, David
, (2022/02/19)
Social insects are in mutualism with microorganisms, contributing to their resistance against infectious diseases. The fungus Pseudallescheria boydii SNB-CN85 isolated from termites produces ovalicin derivatives resulting from the esterification of the less hindered site of the ovalicin epoxide by long-chain fatty acids. Their structures were elucidated using spectroscopic analysis and semisynthesis from ovalicin. For ovalicin, these compounds displayed antiprotozoal activities against Plasmodium falciparum and Trypanosoma brucei, with IC50 values of 19.8 and 1.1 μM, respectively, for the most active compound, i.e., ovalicin linoleate. In parallel, metabolomic profiling of a collection of P. boydii strains associated with termites made it possible to highlight this class of compounds together with tyroscherin derivatives in all strains. Finally, the complete genome of P. boydii strains was obtained by sequencing, and the cluster of potential ovalicin and ovalicin biosynthesis genes was annotated. Through these metabolomic and genomic analyses, a new ovalicin derivative named boyden C, in which the 6-membered ring of ovalicin was opened by oxidative cleavage, was isolated and structurally characterized.
Identification and α -Glucosidase Inhibitory Activity of Meroterpenoids from Hericium erinaceus
Bao, Li,Chen, Baosong,Han, Junjie,Liu, Hongwei,Ma, Ke,Wang, Wenzhao
, p. 571 - 578 (2020/06/03)
Hericium erinaceus is a very popular edible and medicinal mushroom used for the treatment of enervation and gastrointestinal diseases in Eastern Asia. Chemical investigation on the fruiting body of Hericium erinaceus led to the isolation of 4 new (1 - 4) and 10 known meroterpenoids (5 - 14). The structures of new compounds were determined via analysis of NMR and MS data in combination with chemical derivatization. The inhibitory activities of 1 - 14 against α -glucosidase were evaluated using p -nitrophenyl- α -D-glucopyranoside, sucrose, or maltose as substrate. Compounds 6, 9, 11 - 13 were demonstrated to show the α -glucosidase inhibitory activities. This work confirms the potential of H. erinaceus in the treatment of diabetes.
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 fully enzymatic esterification/transesterification sequence for the preparation of symmetrical and unsymmetrical trehalose diacyl conjugates
Prabhakar, Sunchu,Vivès, Thomas,Ferrières, Vincent,Benvegnu, Thierry,Legentil, Laurent,Lemiègre, Lo?c
supporting information, p. 987 - 995 (2017/08/14)
Monoacyl and diacyl trehalose were synthesized in two steps from trehalose and carboxylic acids. The carboxylic acids were converted first into the corresponding 2,2,2-trifluoroethyl esters through a biocatalyzed esterification. The acyl donor was then transferred to the disaccharide through biocatalyzed transesterification. Thanks to microwave reaction conditions the transesterification proceeded selectively to the monoacyl trehalose or to the diacyl counterparts depending on the sole amount of the acyl donor. These reaction conditions were also applied for the preparation of unsymmetrical diacyl trehalose in a fully enzymatic sequence.
