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HPLC, UV-Vis and NMR spectroscopic and DFT characterization of purpurin isolated from Rubia tinctorum L.

DOI: 10.2298/hemind120419058m

Keywords: Rubia tinctorum , HPLC-UV , antioxidant activity , anthraquinone , DFT study

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Abstract:

Purpurin (1,2,4-trihidroxyanthraquinone), a naurally occuring anthraquinone pigment present in the root of Rubia tinctorum (Mull. Arg.) Zahlbr. was isolated from the plant, purified and characterized by HPLC chromatography, UV-Vis and NMR spectroscopy. The geometries of the purpurin conformers were optimized using the B3LYP/6-311+G(d,p) level of theory. It was found that all conformations have similar energies and that the corresponding purpurin radicals are planar. In spite of their planarity, there is no significant electron delocalization over the A and C rings. The antioxidant properties of purpurin were investigated using the colorimetric assay as Trolox-equivalent antioxidant capacity, and theoretical BDE (Bond Dissociation Enthalpy). Both methods revealed that purpurin has strong antioxidant capacity.

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