Isolation and Structural Elucidation of Allantoin a Bioactive Compound from Cleome viscosa L.: A Combined Experimental and Computational Investigation

Abstract

Allantoin, a crystalline compound was isolated from the methanolic extract of Cleome viscosa and it was reported for first time from this plant. The structure of Allantoin was elucidated by single crystal XRD and it was further confirmed through FTIR and ESI-MS spectroscopy techniques. It was crystallized in monoclinic crystal system with the space group P2i/c. Electronic structure characterization of the isolated Allantoin was done through density functional theory calculation. The atomic charges, dipole moment, frontier molecular orbital and the electrostatic potential map of the molecule in the gaseous phase and in the active site have also been analyzed. The optimized geometry was used for molecular docking to identify the possible binding mode. Furthermore, the in vitro antibacterial activity of the isolated Allantoin against Gram-positive and Gram-negative bacteria was evaluated. Maximum Inhibitory Concentrations (MIC) of isolated Allantoin results showed 4 µg/mL for B. subtilis and 8 µg/mL for S. aureus, E. coli and K. pneumoniae.

Experimental and computational studies of an antiplasmodial derivative of allantoin; antimycobacterial essential oil from Cordia batesii WERNHAM (Boraginaceae)

“…It is shown in Fig. 4 and takes in account previous reports on 1 [ 44 , 49 ]. The five membered ring is almost planar as observed in the case of allantoin ( 1 ) [ 19 ].…”

“…Its molecular formula was deduced as C 7 H 8 N 6 O 5 from the ESI-MS signal at m/z 257.4 [M+H] + and from the HR-LC/MS signal at m/z 279.1603 [M+Na] + , in accordance with seven degrees of unsaturations. Additional data from the ESI-MS spectrum displayed other peaks at m/z 159.4 [M 1 +H] + and 181.6 [M 1 + Na] + which are characteristics of allantoin ( 1 ) [ 44 ]. These preliminary data suggested a close relationship between allantoin ( 1 ) and compound 2 .…”

“…Lakshmanan et al [ 44 ] confirmed through an X-ray analysis that the occurring enantiomer of 1 is its ( S ) one. A thorough analysis of all the spectra and comparison with data from the literature revealed that compound 2 is described for the first time as a new derivative of allantoin ( 1 ); it was identified as ( S , S )-1,3-bis(2,5-dioxoimidazolidin-4-yl)urea, trivially named batesiin ( 2 ).…”

Density Functional Theory of a New Derivative of Allantoin with Antiplasmodial Properties, Antimycobacterial Activities of Essential Oil from Cordia Batesii WERNHAM (Boraginaceae)

“…The structure of compound 2 was assigned based on spectroscopic analyses including, UV, 1 Fig. 3 and takes in account previous reports of 1 [39,41]. The five membered ring is almost planar as observed in the case of allantoin (1) [19].…”

“…UV-visible spectrum of 1 displayed two maxima at λmax 183 and 195 nm (representing the absorption bands of amide and imide functions) [19] in one case or a maximum at 265 nm in another case [39]. Despite on the fact that batesiin (2) is characterized by the same chromophore groups, its UV-visible spectrum ( Fig.…”