Isolation, Identification, Molecular and Electronic Structure, Vibrational Spectroscopic Investigation, and Anti-HIV-1 Activity of Karanjin Using Density Functional Theory
“Karanjin” (3-methoxy furano-2,3,7,8-flavone) is an anti-HIV drug, and it is particularly effective in the treatment of gastric problems. The method of isolation of “Karanjin” followed the Principles of Green Chemistry (eco-friendly and effortless method). The optimized geometry of the “Karanjin” molecule has been determined by the method of density functional theory (DFT). Using this optimized structure, we have calculated the infrared wavenumbers and compared them with the experimental data. The calculated wavenumbers are in an excellent agreement with the experimental values. On the basis of fully optimized ground-state structure, TDDFT//B3LYP/LANL2DZ calculations have been used to determine the low-lying excited states of Karanjin. Based on these results, we have discussed the correlation between the vibrational modes and the crystalline structure of “Karanjin.” A complete assignment is provided for the observed FTIR spectra. This is the first report of the isolation, molecular and electronic structure using vibrational spectroscopic investigation, density functional theory, and anti-HIV-1 activity of “Karanjin.” 1. Introduction Pongamia pinnata is a medium sized glabrous tree, found throughout Indian forests [1]. Different parts of this plant have been used as a source of traditional medicine. P. pinnata seeds contain oil which is mainly used in tanning industry for dressing of leather and to some extent it is used in soap industry. Oil is employed in scabies, herpes, and leucoderma, and sometimes as stomachic and cholagogue in dyspepsia and sluggish liver [2]. “Karanjin” is an active principle responsible for the curative effects of the oil in skin disease [1]. Seed extract inhibits growth of herpes simplex virus and also possesses hypoglycemic, antioxidative, antiulcerogenic, anti-inflammatory, and analgesic properties [3]. During the course of exploration of new compounds from P. pinnata seed oil, several workers [4–6] have identified some new compounds of its seed oil apart from “Karanjin.” “Karanjin” possess pesticidal [7], insecticidal [8], and anti-inflammatory activity [9]. Considering the role of “Karanjin” in different areas, in the present communication, we have carried out isolation and identification of “Karanjin” by ecofriendly method and tested for its anti-HIV activity. The molecular structure of the well-known natural product “Karanjin” has been studied using the density functional theory. The equilibrium geometry, harmonic vibrational frequencies, and HOMO-LUMO gap have been calculated by the density functional B3LYP method
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