Constituents of pepper. part III. Isobutyl amides from pepper (Piper nigrum L.).

Structural and Sensory Characterization of Key Pungent and Tingling Compounds from Black Pepper (Piper nigrum L.)

“…25 showed a molecular mass of 383 Da and indicated an elemental composition of C 24 H 33 NO 3 . Careful assignment of all 1D/2D NMR data confirmed the structure of 6c as the recently reported guineensine. , The LC-MS and the NMR spectra of the compound 6b isolated from fraction 26 indicated the molecular mass of 381 Da and revealed that the structure of this compound differed from that of 6c only in the amide moiety representing a pyrrolidine ring instead of an isobutylamine residue. Comparison of spectroscopic data and 1D/2D NMR experiments as well as comparison with data found in literature allowed the identification of compound 6b as brachyamide A (Figure ).…”

“…LC-MS experiments, 1 H, 13 C, and DEPT NMR analysis revealed a molecular formula of C 22 H 41 NO, the presence of two conjugated, trans -configured double bonds, the absence of another isolated double, and an isobutylamine moiety in the structure of 9c . Taking all of the spectroscopic data into consideration, the structure of 9c was identified as (2 E ,4 E )- N -isobutyl-octadeca-2,4-dienamide (Figure ), which has been reported earlier. ,, LC-MS analysis of amides 10c and 11c showed a pseudomolecular ion with m / z 362 ([M + H] + ), thus suggesting the presence of two further methylene groups when compared to 7c/8c . NMR spectroscopic analysis revealed three terminal methyl groups H–C(3′), H–C(4′), and H–C(20), six olefinic protons assigned as H–C(2–5) and H–C­(14/15) or H–C­(15/16), and 13 methylene groups assigned as H–C(1′), H–C(6–13), or H–C(6–14) and H–C(16–19) or H–C(17–19) for each compound.…”

Chemical constituents of peppers (Piper spp.) and application to food preservation: naturally occurring antioxidative compounds.

“…A Amax of 258 nm suggested the presence of trans-oa,1,-y,8-double bond conjugated to a carbonyl group; it was confirmed by NMR analysis. The data ofthis compound were identical with those of authentic pellitorine, N-isobutyl-2E,4E-decadienamide [9] (19). We identified other components from the neutral fraction to be piperine [1], methyl piperate [7b], N-isobutyl-2E,4E,8Z-eicosatrienamide [10], and 1-sitosterol [11].…”

Powder Microscopic, Physicochemical, HPTLC and Antioxidant Studies on Noccik Kudinir Chooranam – A Polyherbal Siddha Formulation

“…The phytochemical literature of the ingredients shows that the drug has variety of phytoconstitutes. [26][27][28][29][30][31][32][33][34][35] The ingredients were reported with many pharmacological activities. [36][37][38][39][40][41][42][43][44][45][46][47][48][49][50][51] Previous epidemiological studies report that these antioxidant compounds also possess anti inflammatory, antiatherosclerotic, antitumor, antimutagenic, anticarcinogenic, antibacterial and antiviral activities to greater or lesser extent.…”