Conformational stability, spectroscopic and computational studies, HOMO–LUMO, NBO, ESP analysis, thermodynamic parameters of natural bioactive compound with anticancer potential of 2-(hydroxymethyl)anthraquinone

• The optimized geometrical parameters of HMA were obtained by HF and B3LYP methods.
• Global minimum energy for six conformers of HMA have been studied.
• HOMO and LUMO analysis have been performed.
• Electrostatic potential surface has been performed.
• Thermodynamic parameter has been performed.

Natural product drugs play a dominant role in pharmaceutical care. Nature is an attractive source of new therapeutic candidate compounds as a tremendous chemical diversity is found in millions of species of plants, animals, marine organism and micro-organism. A antifungal activity against important opportunist micro-organism and against those involved in superficial mycosis, all from nosocomial origin. The acute in vitro cytotoxicity evaluation of each anthraquinone (AQ) isolated from these bioactive extracts, on a mammalian eukaryotic cell line (Vero cells), allowed us to establish the non-cytotoxic concentration range, which was used to evaluate the anti-microbial effect. A comprehensive ab initio calculation using the DFT/6-31+G(d) level theory showed that 2-(hydroxymethyl)anthraquinone can exist in four possible conformations, which can interchange through the OH group on the five-membered ring. Density functional theory calculations were used to predict the vibrational frequencies and to help in normal mode, assignments. Furthermore, a natural bond orbital analysis was performed describing each hydrogen bond as donor accepter interaction. The Fourier transform infrared spectra (4000–400 cm−1) and the Fourier transform Raman spectra (3500–100 cm−1) of the HMA in the solid space have been recorded. The calculated HOMO and LUMO energies show that charge transfer occurs within the molecule. The calculated ESP contour map shows the electrophilic and nucleophilic region of the molecule.

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