2825-79-8Relevant academic research and scientific papers
Unexpected AChE inhibitory activity of (2E)α,β-unsaturated fatty acids
Loesche, Anne,Wiemann, Jana,Al Halabi, Zayan,Karasch, Julia,Sippl, Wolfgang,Csuk, René
, p. 3315 - 3319 (2018/09/17)
A small library of (E) α,β-unsaturated fatty acids was prepared, and 20 different saturated and mono-unsaturated fatty acids differing in chain length were subjected to Ellman's assays to determine their ability to act as inhibitors for AChE or BChE. While the compounds were only very weak inhibitors of BChE, seven molecules were inhibitors of AChE holding IC50 = 4.3–12.8 M with three of them as significant inhibitors of this enzyme. The results have shown trans 2-mono-unsaturated fatty acids are better inhibitors for AChE than their saturated analogs. Furthermore, the screening results indicate that the chain length is crucial for obtaining an inhibitory efficacy. The best results were obtained for (2E) eicosenoic acid (14) showing inhibition constants Ki = 1.51 ± 0.09 M and Ki′ = 7.15 ± 0.55 M. All tested compounds were mixed-type inhibitors with a dominating competitive part. Molecular modelling calculations indicate a different binding mode of active/inactive compounds for the enzymes AChE and BChE.
Piperlongumine B and analogs are promising and selective inhibitors for acetylcholinesterase
Wiemann, Jana,Karasch, Julia,Loesche, Anne,Heller, Lucie,Brandt, Wolfgang,Csuk, René
, p. 222 - 231 (2017/08/14)
Piperlongumine B (19), an alkaloid previously isolated from long pepper (Piper longum) has been synthesized for the first time in a short sequence and in good yield together with 19 analogs. Screening of these compounds in Ellman's assays showed several of them to be good inhibitors of acetylcholinesterase while being less active for butyrylcholinesterase. Activity of the compounds increased with the ring size of the heterocycle, and a maximum of activity was observed for an analog holding 12 methylene groups in the aliphatic side chain. These compounds may be regarded as promising candidates for the development of efficient inhibitors of acetylcholinesterase being useful for the treatment of Alzheimer's disease.
Biosynthesis-Assisted Structural Elucidation of the Bartolosides, Chlorinated Aromatic Glycolipids from Cyanobacteria
Le?o, Pedro N.,Nakamura, Hitomi,Costa, Margarida,Pereira, Alban R.,Martins, Rosário,Vasconcelos, Vitor,Gerwick, William H.,Balskus, Emily P.
supporting information, p. 11063 - 11067 (2016/07/06)
The isolation of the bartolosides, unprecedented cyanobacterial glycolipids featuring aliphatic chains with chlorine substituents and C-glycosyl moieties, is reported. Their chlorinated dialkylresorcinol (DAR) core presented a major structural-elucidation challenge. To overcome this, we discovered the bartoloside (brt) biosynthetic gene cluster and linked it to the natural products through in vitro characterization of the DAR-forming ketosynthase and aromatase. Bioinformatic analysis also revealed a novel potential halogenase. Knowledge of the bartoloside biosynthesis constrained the DAR core structure by defining key pathway intermediates, ultimately allowing us to determine the full structures of the bartolosides. This work illustrates the power of genomics to enable the use of biosynthetic information for structure elucidation.
(Z) 1'-propylbutyl 3-octadecenoate from Fagara budrunga fruits
Naik,Katke, Sujata,Banhatti, Padmini,Natu
, p. 122 - 124 (2007/10/03)
Chemical constituents of the Indian medicinal plant Fagara budrunga commonly known as mullilam, have been isolated. In addition to the known compounds a new ester has been obtained. It has been assigned the structure (Z) 1'-propylbutyl 3-octadecenoate 1 from chemical conversions and spectral analysis.
