title: Vibrational spectra, structure and antioxidant activity of gossypol imine derivatives.
abstract: The structures and tautomeric equilibria of natural polyphenol gossypol and four its imine derivatives were studied by FT-IR-, NMR-spectroscopy and quantum chemistry methods. It was shown that gossypol Schiff bases exist in solution as enamine-enamine tautomer and hydrazones as imine-imine tautomer. Infrared absorption spectra of studied compounds were simulated using the PM3 method. The fundamental vibrational frequencies were evaluated using various scale factors which yield a good agreement between observed and calculated frequencies. Free radical scavenging activity of gossypol and its imine derivatives was evaluated using DPPH method. Antioxidant activity of studied compounds was characterized. Gossypol hydrazones were shown to be more efficient, while Schiff base to be less efficient as antioxidants in comparison with gossypol itself.
authors.affiliation: L.M. Litvinenko Institute of Physical-Organic and Coal Chemistry NAS of Ukraine, Donetsk 83-114, R. Luxemburg 70, Ukraine. ilkevych@list.ru
authors.forename: N S
authors.initials: NS
authors.lastname: Ilkevych
authors.forename: G
authors.initials: G
authors.lastname: Schroeder
authors.forename: V I
authors.initials: VI
authors.lastname: Rybachenko
authors.forename: K Y
authors.initials: KY
authors.lastname: Chotiy
authors.forename: R A
authors.initials: RA
authors.lastname: Makarova
mesh_terms: D000975:Antioxidants / Q000737:chemistry*; D001713:Biphenyl Compounds / Q000737:chemistry; D006072:Gossypol / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010851:Picrates / Q000737:chemistry; D059808:Polyphenols / Q000737:chemistry*; D012997:Solvents; D017550:Spectroscopy, Fourier Transform Infrared; D013816:Thermodynamics; D014732:Vibration
chemical_list: D000975:Antioxidants; D001713:Biphenyl Compounds; D007097:Imines; D010851:Picrates; D059808:Polyphenols; D012997:Solvents; C004931:1,1-diphenyl-2-picrylhydrazyl; D006072:Gossypol