LC-HRMS/MS-based phytochemical profiling of Piper spices: Global association of piperamides with endocannabinoid system modulation was written by Luca, Simon Vlad;Minceva, Mirjana;Gertsch, Juerg;Skalicka-Wozniak, Krystyna. And the article was included in Food Research International in 2021.Name: (2E,4E)-N-Isobutyldeca-2,4-dienamide The following contents are mentioned in the article:
The plant genus Piper comprises extensively consumed spice taxa like black pepper (P. nigrum L.) or long pepper (P. longum L.). The chronic dietary use of different Piper spices has been associated with different health benefits, though the mol. mechanisms remain poorly understood. The aim of this work was to perform the liquid-chromatog.-high-resolution tandem mass spectrometry (LC-HRMS/MS) profiling and LC-DAD quantification of piperamides in several Piper species and varieties and study their ability to modulate the endocannabinoid system (ECS). LC-HRMS/MS anal. revealed a number of 42 piperamides grouped into six structural classes, with 22 of them, notably piperine, retrofractamide B, guineensine, piperchabamide C, being also quantified by LC-DAD. The multivariate anal. showed that P. nigrum and P. longum are very similar with respect to their piperamide profile, while the other Piper spices (P. retrofractum, P. guineense, P. cubeba, P. borbonense) might have significantly different metabolite patterns. The results from the biol. assays confirmed that guineensine and total piperamides are strongly correlated with anandamide (AEA) cellular uptake inhibition. While none of the Piper spice extracts showed binding activity at cannabinoid CB1 receptors, some P. nigrum varieties exhibited moderate binding interactions with CB2 receptors. Overall, the anal. profiling enabled global annotations of piperamides associated to cannabimimetic effects in Piper spices. This study involved multiple reactions and reactants, such as (2E,4E)-N-Isobutyldeca-2,4-dienamide (cas: 18836-52-7Name: (2E,4E)-N-Isobutyldeca-2,4-dienamide).
(2E,4E)-N-Isobutyldeca-2,4-dienamide (cas: 18836-52-7) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. Ionic, or saltlike, amides are strongly alkaline compounds ordinarily made by treating ammonia, an amine, or a covalent amide with a reactive metal such as sodium.Name: (2E,4E)-N-Isobutyldeca-2,4-dienamide
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics