Comparison of radical scavenging properties of gosypol and its derivatives in the reaction with DPPH

doi:10.26565/2220-637X-2024-42-07

Oleksii Dykun L.M. Litvinenko Institute of Physical-Organic and Coal Chemistry NAS of Ukraine, 50 Kharkivske shose, Kyiv, 02155, Ukraine https://orcid.org/0000-0003-1550-5979
Viktor Anishchenko L.M. Litvinenko Institute of Physical-Organic and Coal Chemistry NAS of Ukraine, 50 Kharkivske shose, Kyiv, 02155, Ukraine https://orcid.org/0000-0001-5076-3549
Andrii Redko L.M. Litvinenko Institute of Physical-Organic and Coal Chemistry NAS of Ukraine, 50 Kharkivske shose, Kyiv, 02155, Ukraine https://orcid.org/0000-0001-7741-1834
Volodymyr Rybachenko L.M. Litvinenko Institute of Physical-Organic and Coal Chemistry NAS of Ukraine, 50 Kharkivske shose, Kyiv, 02155, Ukraine https://orcid.org/0000-0002-5568-7335

DOI: https://doi.org/10.26565/2220-637X-2024-42-07

Keywords: gossypol, tautomerism, radical scavenging properties, DPPH, stoichiometry

Abstract

Radical scavenging activity of 7,7'-ditosyloxygossypol in reaction with 2,2'-diphenyl-1-piсrylhydrazyl (DPPH) in ethanol was evaluated by total stoichiometries and EC₅₀ values. The stoichiometric coefficient of the reaction of DPPH with 7,7'-ditosyloxygossypol is close to two. This indicates that in ethanol this compound exists mainly in the dilactol tautomeric form, and the lactol hydroxyl groups are not capable of reacting with DPPH. Such a result can be an indirect confirmation that no tautomeric transformation occurs during the reaction with DPPH due to the consumption of one of the tautomers. A comparative analysis of the radical scavenging properties of 7,7'-ditosyloxygossypol, gossypol, gossypol Schiff base with 4-methoxyaniline and gossypol hydrazone with phenylhydrazine in reactions with DPPH was carried out. The influence of tautomerism on the radical scavenging properties of the investigated compounds was determined. It was established that the presence of NH groups in the structure of gossypol Schiff base with 4-methoxyaniline and hydrazone with phenylhydrazine does not increase the radical scavenging properties in the reaction with DPPH. And the change of the tautomeric form and the appearance of additional phenolic hydroxyl groups (instead of NH groups) will lead to increased radical scavenging properties. It was shown that the most effective radical scavenging agent is the gossypol hydrazone in the diimine tautomeric form (6 phenolic hydroxyl groups). And the least effective is 7,7'-ditosyloxygossypol (2 phenolic hydroxyl groups).

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