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ISSN 1998-9539

Decline of Prooxidant Activity of Butyl and Phenyl Derivatives of Tin in the Presence of meso-Tetrakis(3,5-di-tert-butyl-4-hydroxyphenyl)porphyrin

Margarita N. Kolyada,а Victoriya P. Osipova,a@ Nadezhda T. Berberova,b Yuri T. Pimenov,b and Elena R. Milaevac

aSouthern Scientific Center of RAS, 344006 Rostov-on-Don, Russia

bAstrakhan State Technical University, 414025 Astrakhan, Russia

cLomonosov Moscow State University, Department of Chemistry, 119991 Moscow, Russia

@Corresponding author E-mail:


DOI: 10.6060/mhc160542o

Macroheterocycles 2017 10(1) 57-61


Lipid peroxidation (LP) is one of the major factors of pathologies of various genesis including the toxic impact of heavy metals. The promising polyfunctional hybrid antioxidants are the compounds containing both porphyrin and sterically hindered phenol moieties that act by different mechanisms of lipid peroxidation inhibition. The influence of synthetic meso-substituted porphyrins – meso-tetrakis(3,5-di-tert-butyl-4-hydroxyphenyl)porphyrin (R4PH2) and its analogue, free base of meso-tetraphenylporphyrin (TPPH2) which does not bear 2,6-di-tert-butylphenol antioxidant fragment on the lipid peroxidation of fish fodder in the presence of ((С4Н9)3SnCl, (С4Н9)2SnCl2, (С6Н5)3SnCl and (С6Н5)2SnCl2)in comparison with widely used antioxidants (α-tocopherol, 2,6-di-tert-butylphenol, 2,6-di-tert-butyl-4-methylphenol (BHT, ionol)) has been studied. Tributyl- and triphenyltin chlorides are known prooxidants, and despite the fact that their application as biocides is strongly restricted, nevertheless, they accumulate in bed silt, in aquatic media, hydrobionts and therefore are detected in various fish products including fish fodder.

In this study, we measured the level of primary LP products – hydroperoxides (LOOH) in the lipids extract of fish fodder ОТ-6A. The experiment has been performed at 25±1 C once in a week in the period of 12 weeks. The concentration of porphyrins and antioxidants was 150 mg per 1 kg of fish fodder (0.015 %) that is the normal content of antioxidants in the fodder ≤ 0.02 % (200 mg/kg). The concentration of organotins was 15 µmol/g. It has been shown that tin compounds as additives to the fish fodder lipids increase the level of LOOH that does not depend on the organic group nature,  however, is influenced by their number. Disubstituted organotin compounds (С4Н9)2SnCl2, and (C6H5)2SnCl2 demonstrate the highest activity – the level of LP products increases 6–7 times when compared to control without any additives. The free base of meso-tetraphenylporphyrin (TPPH2) which does not bear 2,6-di-tert-butylphenol antioxidant fragment acts as a prooxidant in lipids autooxidation and in the media containing organotins as well. meso-Tetrakis(3,5-di-tert-butyl-4-hydroxyphenyl)porphyrin (R4PH2) is an effective inhibitor of LP in fish fodder both in the absence of toxicants and in the presence of organotins as LP promoters. We propose that R4PH2 is oxidized to form a relatively stable biradical which is transformed to the porphodimethenediquinomethide and the main product – meso-tetrakis(3,5-di-tert-butyl-4-quinomethide)porphyrinogene. The oxidation steps are reversible that influences the high antioxidant activity of R4PH2.Moreover, the concentration of R4PH2 was less than the concentration of widely used antioxidants under investigation, however, the activity was higher. Therefore, we can conclude that inhibitory activity of R4PH2 studied in model system of LP of fish fodder is higher that the activity of widely used antioxidants (α-tocopherol, 2,6-di-tert-butylphenol, 2,6-di-tert-butyl-4-methylphenol (ionol)). These results allow one to suggest that meso-tetrakis(3,5-di-tert-butyl-4-hydroxyphenyl)porphyrin (R4PH2) is a promising antioxidant and detoxification agent which can be applied as stabilizer of fish fodder.


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