2466-36-6Relevant articles and documents
BIOSYNTHESIS OF PIPERLONGUMINE
Prabhu, Bharathi R.,Mulchandani, Newand B.
, p. 2589 - 2592 (1985)
The incorporation of L-lysine and L-phenylalanine into piperlongumine has been demonstrated in Piper longum.The subsequent stepwise degradation to methyl-(3,4,5-trimethoxyphenyl)-propanoate and δ-aminovaleric acid revealed that the C6-C3 moiety of the alkamide arises from phenylalanine; the heterocyclic ring is biosynthesized from lysine.It has also been shown that DL-tyrosine and sodium acetate are poor precursors for piperlongumine. Key Word Index - Piper longum; Piperaceae; alkamides; piperlongumine; biosynthesis.
Fragmentation pattern of amides by EI and HRESI: Study of protonation sites using DFT-3LYP data
Fokoue,Marques,Correia,Yamaguchi,Qu,Aires-De-Sousa,Scotti,Lopes,Kato
, p. 21407 - 21413 (2018/06/26)
Amides are important natural products which occur in a few plant families. Piplartine and piperine, major amides in Piper tuberculatum and P. nigrum, respectively, have shown a typical N-CO cleavage when analyzed by EI-MS or HRESI-MS. In this study several synthetic analogs of piplartine and piperine were subjected to both types of mass spectrometric analysis in order to identify structural features influencing fragmentation. Most of the amides showed an intense signal of the protonated molecule [M + H]+ when subjected to both HRESI-MS and EI-MS conditions, with a common outcome being the cleavage of the amide bond (N-CO). This results in the loss of the neutral amine or lactam and the formation of aryl acylium cations. The mechanism of N-CO bond cleavage persists in α,β-unsaturated amides because of the stability caused by extended conjugation. Computational methods determined that the protonation of the piperamides and their derivatives takes place preferentially at the amide nitrogen supporting the dominant the N-CO bond cleavage.
Synthesis of Piperlongumine Analogues and Discovery of Nuclear Factor Erythroid 2-Related Factor 2 (Nrf2) Activators as Potential Neuroprotective Agents
Peng, Shoujiao,Zhang, Baoxin,Meng, Xianke,Yao, Juan,Fang, Jianguo
, p. 5242 - 5255 (2015/08/03)
The cellular antioxidant system plays key roles in blocking or retarding the pathogenesis of adult neurodegenerative disorders as elevated oxidative stress has been implicated in the pathophysiology of such diseases. Molecules with the ability in enhancing the antioxidant defense thus are promising candidates as neuroprotective agents. We reported herein the synthesis of piperlongumine analogues and evaluation of their cytoprotection against hydrogen peroxide- and 6-hydroxydopamine-induced neuronal cell oxidative damage in the neuron-like PC12 cells. The structure-activity relationship was delineated after the cytotoxicity and protection screening. Two compounds (4 and 5) displayed low cytotoxicity and confer potent protection of PC12 cells from the oxidative injury via upregulation of a panel of cellular antioxidant molecules. Genetically silencing the transcription factor Nrf2, a master regulator of the cellular stress responses, suppresses the cytoprotection, indicating the critical involvement of Nrf2 for the cellular action of compounds 4 and 5 in PC12 cells.
