+ Resolve Article
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter

+ Translate
+ Subscribe to Site Feed
GeoScience Most Shared ContentMost Shared Content

Enhancement of the peroxidase-mediated oxidation of butylated hydroxytoluene to a quinone methide by phenolic and amine compounds

, : Enhancement of the peroxidase-mediated oxidation of butylated hydroxytoluene to a quinone methide by phenolic and amine compounds. Chemico-Biological Interactions 72(1-2): 157-173

We have recently demonstrated that butylated hydroxyanisole (BHA) markedly stimulates the peroxidase-dependent oxidation of butylated hydroxytoluene (BHT) to the potentially toxic BHT-quinone methide. Using both horseradish peroxidase and prostaglandin H synthase we now report the ability of a wide variety of compounds to stimulate peroxidase-dependent activation of BHT. These compounds include several phenolic compounds commonly present in pharmacologic preparations or occurring naturally in foods. The ability of a given compound to stimulate BHT oxidation was found to depend on the type of radical it forms upon peroxidase oxidation. Compounds which have been shown to form phenoxy radicals or nitrogen-centered cation radicals were observed to enhance BHT oxidation. Conversely, compounds which are known to form peroxy radicals or semiquinone radicals either inhibited or had no effect on BHT oxidation. Compounds which enhanced BHT oxidation (monitored by covalent binding of [14C]BHT to protein) were also observed to stimulate the formation of BHT-quinone methide and stilbenequinone. This suggested a common mechanism of interaction of these compounds with BHT. The stimulation of BHT covalent binding by BHA was also seen in various human and animal tissues using either arachidonic acid or hydrogen peroxide as substrate. The possible toxicologic implications of the enhancement of peroxidase-catalyzed BHT oxidation to BHT-quinone methide are discussed.


PMID: 2510948

Other references

Michaelis, P., 1935: Investigations on the problem of cytoplasmic inheritance. Further work on cytoplasmic inheritance from experiments on Epilobium shewed that the cytoplasm affects not only gene quality but also quantity and that it is of importance for physiological development as well as genetically.

Best, P.; Findlay, K.; Sekiguchi, K.; Peddemors, V.; Rakotonirina, B.; Rossouw, A.; Gove, D., 1998: Winter distribution and possible migration routes of humpback whales Megaptera novaeangliae in the southwest Indian Ocean. ine Ecology Progress Series ruary 12; 162: 287-299

Assaha, D.V.M.; Ueda, A.; Saneoka, H.; Al-Yahyai, R.; Yaish, M.W., 2017: The Role of Na + and K + Transporters in Salt Stress Adaptation in Glycophytes. Ionic stress is one of the most important components of salinity and is brought about by excess Na<sup>+</sup> accumulation, especially in the aerial parts of plants. Since Na<sup>+</sup> interferes with K<sup>+</s...

Gutiérrez, J.Pablo.; García-Saisó, Sán.; Espinosa-de la Peña, R.; Balandrán, D.Alejandra., 2017: Monitoring of inequality in financial protection and healthcare in Mexico: an analysis of health surveys 2000, 2006 and 2012. To analyze trends in inequality in financial protection and healthcare in Mexico between 2000 and 2012, using simple and complex measures. Analysis of national health surveys 2000, 2006 and 2012, generating estimates of absolute and relative gaps...

Xu, Z.; Gao, Y., 2005: Recursion formula of energy levels for oxygen-like ions. A recursion formula of energy levels for Oxygen-like ions has been given based on the generalization of the perturbation expansion. It is found that the formula is considerably simple and accurate.

Jacobs, MR., 1980: Toxoplasmosis in southern Africa. Dissertation Abstracts International B Sciences and Engineering, 413: 825

Dipaola, G., 1972: The possibility of mechanizing almond harvesting. Methods of shaking the nuts from the tree and collecting them are discussed and results with various types of equipment are compared with manual harvesting. The results were promising and tree damage was negligible, but the proportion of fruit loo...

Vyskocil, A.; Fiala, Z.; Tejnorová, I.; Tusl, M., 1991: Stress reaction in developing rats exposed to 1% lead acetate. Effects of a three-month exposure of both male and female rats under their development to lead acetate in drinking water on the hypothalamus-pituitary gland-thyroid gland-suprarenals and sympathico-adrenal systems were evaluated by determining nor...

Maur, M.; Iorio, A.; Caffarello, J., 1965: Gastric ulcers of the upper third. Prensa Medica Argentina 52(49): 3019-3026

Hampel, D.; Mosandl, A.; Wüst, M., 2005: Biosynthesis of mono- and sesquiterpenes in carrot roots and leaves (Daucus carota L.): metabolic cross talk of cytosolic mevalonate and plastidial methylerythritol phosphate pathways. The biosynthesis of the monoterpenes terpinolene and myrcene and the sesquiterpene beta-caryophyllene in roots and leaves of two carrot varieties (Daucus carota L. cultivars Bolero and Kazan) were investigated by in vivo feeding experiments with [...