Thiobarbituric acid reactivity of autoxidized candicidin

Add time:09/08/2019    Source:sciencedirect.com

The antifungal polyene antibiotic candicidin isolated from soil actinomyces is produced by Streptomyces sp. It is one of many macrocyclic ring compounds which display potent antifungal properties with no apparent antibacterial activity. These antibiotics are characterized by the possession of a large macrolide ring containing a series of conjugated double bonds (1). These double bonds confer potential instability to the molecule similar to that seen with both squalene and the polyunsaturated fatty acids (PUFA) (2). This type of oxidative instability in the presence of molecular oxygen is characterized by free-radical-mediated chain reactions. Consequently, autoxidation of polyene antibiotics has been recognized as a problem of handling and storage which results in loss of antifungal activity (3).Several studies have shown that autoxidation of polyene antibiotics results in the formation of peroxides, epoxides, low-molecular-weight carbonyls, and carboxylic acids (4–6). The thiobarbituric acid (TBA) reaction has been extensively used in the food industry as well as in basic biology for the detection of aldehyde by-products of oxidative reactions. The pink chromogen formed is an adduct of malondialdehyde (MDA) and two molecules of TBA. When the thiobarbituric acid reaction is applied to autoxidized candicidin a 532-nm absorbing chromogen is produced with spectral properties similar to those of malondialdehyde. The purpose of this study has been the characterization of the chromogen.

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