Anticholinesterases and antioxidant alkamides from Piper nigrum fruits

Abstract

The anticholinesterase and antioxidant effects of five different extracts of Piper nigrum were evaluated. Twenty-one known alkamides were isolated from active ethyl acetate extract and investigated for their cholinesterase inhibitory and antioxidant effects. Among them, piperine (2), piperettine (5) and piperettyline (20) exhibited dual inhibition against AChE and BChE, and feruperine (18) was the most potent selective inhibitor of BChE. Molecular docking simulation was performed to get insight into the binding interactions of the ligands and enzymes. In addition, N-trans-feruloyltyramine (3) contributed to the strongest DPPH radical-scavenging activity. The self-induced Aβ aggregation inhibition of 2, 5 and 18 was further evaluated. Results indicated that some alkamides could be multifunctional lead candidates for Alzheimer's disease therapy.

Metabolites Identification of Bioactive Compounds Daturataturin A, Daturametelin I, N-Trans-Feruloyltyramine, and Cannabisin F From the Seeds of Datura metel in Rats

“…N -trans-feruloyltyramine could strongly suppress mRNA expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) via suppression of AP-1 and the JNK signaling pathway ( Jiang et al, 2015 ). Meanwhile, N -trans-feruloyltyramine exhibited the strongest DPPH radical-scavenging activity and cytotoxic effects against CCRF-CEM cell line with IC 50 values of 10.3 μg/mL ( Chen et al, 2015 ; Tu et al, 2016 ). Moreover, cannabisin F could successfully inhibit both ErbB1 and ErbB2, exhibiting better MolDock score than other selected inhibitors ( Hu et al, 2016 ).…”

Protective Effect of Acmella Ciliata Extract and Spilanthol in Streptozotocin-induced Sporadic Alzheimer's Disease Mouse Model: Possible Involvement of the of Decreased Oxidative Stress by Activating TRPV1 Receptors

“…Acetylcholine is degraded by AChE whose inhibition by AChE inhibitors is the most effective pharmacological approach for the symptomatic treatment of AD (Sorial and Sayed 2017;Weller 2018;Záborszky et al 2018;Zhang et al 2019). In the current study, the effect of treatments on AChE activity was not evaluated but we do not rule out the possibility that spilanthol, the compound we consider responsible for the plant's nootropic effects, has AChE inhibiting activity since it is reported that alkamides have such a property (Tu et al 2016).…”

“…As already reported, alkamides represent a class of natural compounds that are highly active in the CNS as they produce antinociceptive (Rios et al 2006;Gertsch et al 2008;Déciga-Campos et al 2010;Ong et al 2011;Das et al 2014), immunomodulatory (Gertsch 2008), anticholinesterases and antioxidant effects (Tu et al 2016). Previous studies suggest that these effects may be related to TRPV1 receptors modulation (Nomura et al 2013; de la Rosa-Lugo et al 2017).…”

“…Acmella ciliata, one of the plants popularly known as jambu in Brazil, is an herb used in typical northern Brazil cuisine and folk medicine. Jambu is famous for its sensorial effects, such as anesthetic, numbing, tingling and cooling feeling, due to the well-known phytochemical alkamide spilanthol [(2E,6E,8E)-N- (Gertsch 2008), anticholinesterases and antioxidant effects (Tu et al 2016). Previous studies suggest that the analgesic and antinociceptive effects could be related to TRPV1 receptors modulation (Nomura et al 2013; de la Rosa-Lugo et al 2017).…”

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“…Black pepper has been used in the Asian folk eISSN: 2550-2166 © 2020 The Authors. Published by Rynnye Lyan Resources MINI REVIEW medicine and the Indian Ayurvedic System of medicine folklore medicine of Latin America since many years ago (Tu et al, 2015). Pepper was also reported that it has been used in folk medicine to treat several ailments (Wan Salleh et al, 2014).…”