Abstract
Research in the field of medicinal plants including Piper species like
long pepper (Piper longum L-Piperaceae) is increasing all over the world
due to its use in traditional and Ayurvedic medicine. Piplartine
(piperlongumine,
5,6-dihydro-1-(2E)-1-oxo-3-(3,4,5-trimethoxypheny1)-2-propenyl-2(1H)
-pyridinone), a biologically active alkaloid/amide was isolated from the
phytochemical investigations of Piper species, as long pepper. This
alkaloid has cytotoxic, anti-fungal, anti-diabetic, anti-platelet
aggregation, anti-tumoral, anxiolytic, anti-depressant,
anti-leishmanial, and genotoxic activities, but, its anticancer property
is the most promising and has been widely explored. The main purpose of
the work is to present a solid state characterization of PPTN using
thermal analysis and vibrational spectroscopy. Quantum mechanical
calculations based on the density functional theory was also applied to
investigate the molecular conformation and vibrational spectrum, which
was compared with experimental results obtained by Raman scattering, far
(terahertz) and mid-infrared adsorption spectroscopy. NBO analysis has
been performed which predict that most intensive interactions in PPTN
are the hyperconjugative interactions between n(1) N6 and pi*(O1-C7)
having delocalization energy of 50.53 kcal/mol, Topological parameters
have been analyzed using `AIM' analysis which governs the three bond
critical points (BCPs), one di-hydrogen, and four ring critical points
(RCP5). MEP surface has been plotted which forecast that the most
negative region is associated with the electronegative oxygen atoms
(sites for nucleophilic activity). Theoretically, to confirm that the
title compoundhas anti-cancer, anti-diabetic and anti-platelet
aggregation activities, it was analyzed by molecular docking
interactions with the corresponding target receptors. The obtained
values of H-bonding parameters and binding affinity prove that its
anti-cancer activity is the more prominent than the other properties.
(C) 2017 Elsevier B.V. All rights reserved.
Users
Please
log in to take part in the discussion (add own reviews or comments).