Biological evaluation of natural and synthesized homovanillic acid esters as inhibitors of intestinal fatty acid uptake in differentiated Caco-2 cells was written by Lieder, Barbara;Hans, Joachim;Hentschel, Fabia;Geissler, Katrin;Ley, Jakob. And the article was included in Molecules in 2019.Formula: C14H25NO The following contents are mentioned in the article:
The modulation of fatty acid uptake by enterocytes represents a promising target for body weight maintenance. Recent results demonstrated that the trigeminal active compounds capsaicin, nonivamide, and trans-pellitorine dose-dependently reduce fatty acid uptake in differentiated Caco-2 cells as a model for the intestinal barrier. However, non-pungent alternatives have not been investigated and structural determinants for the modulation of intestinal fatty acid uptake have not been identified so far. Thus, based on the previous results, we synthesized 23 homovanillic acid esters in addition to the naturally occurring capsiate and screened them for their potential to reduce intestinal fatty acid uptake using the fluorescent fatty acid analog Bodipy-C12 in differentiated Caco-2 cells as an enterocyte model. Whereas pre-incubation with 100μM capsiate did not change fatty acid uptake by Caco-2 enterocytes, a maximum inhibition of -47% was reached using 100μM 1-methylpentyl-2-(4-hydroxy-3-methoxy-phenyl)acetate. Structural anal. of the 24 structural analogs tested in the present study revealed that a branched fatty acid side chain, independent of the chain length, is one of the most important structural motifs associated with inhibition of fatty acid uptake in Caco-2 enterocytes. The results of the present study may serve as an important basis for designing potent dietary inhibitors of fatty acid uptake. This study involved multiple reactions and reactants, such as (2E,4E)-N-Isobutyldeca-2,4-dienamide (cas: 18836-52-7Formula: C14H25NO).
(2E,4E)-N-Isobutyldeca-2,4-dienamide (cas: 18836-52-7) belongs to amides. Amides can be viewed as a derivative of a carboxylic acid RC(=O)OH with the hydroxyl group –OH replaced by an amine group −NR′R″; or, equivalently, an acyl (alkanoyl) group RC(=O)− joined to an amine group. Amides are stable compounds. The lower-melting members (such as acetamide) can be readily purified by fractional distillation. Most amides are solids which have low solubilities in water.Formula: C14H25NO
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics