Aromatic hydroxylation and sulfation of 5-hydroxyflavone by Streptomyces fulvissimus

Abstract

The conversion of 5-hydroxyflavone by various microorganisms was studied. Among them, Streptomyces fulvissimus was the sole microbe which produced a new polar metabolite from 5-hydroxyflavone in addition to 5,4'-dihydroxyand 5,3',4'-trihydroxyflavone. The structure of this polar metabolite was determined to be 5,4'-dihydroxyflavone-4'-sulfate on the basis of mass, infrared, and nuclear magnetic resonance spectroscopies. These results demonstrate that S. fulvissimus catalyzes sulfation at the 4' position of 5,4'-dihydroxyflavone.

The biodegradation of halogenated organic compounds

“…1983). conjugation is apparently uncommon in bacteria though it has been clearly established in Streptomycesjulvissimus (Ibrahim & Abul-Hajj 1989).…”

Improved Release and Metabolism of Flavonoids by Steered Fermentation Processes: A Review

“…Aglycones can be effectively absorbed through the small intestine, while the glycosidic forms, due to their complex structures and large molecular weights, reach the large intestine and are metabolized by human gut microbiota into different more simplified metabolites, which can be later absorbed [ 1 , 13 , 14 ]. Currently, phase I/II metabolites of phenolic compounds such as deglucosides [ 15 , 16 , 17 ], sulfoconjugates [ 18 , 19 ] and glucuronides [ 20 ], can be obtained by a fermentation process. It is therefore interesting to use bacterial or fungal fermentation processes, which not only enhance the release of bound phenolic compounds from the plant cell walls, but also convert phenolic compounds into different metabolites, which can exert other bioactivities.…”

Microbial transformation of zearalenone to a zearalenone sulfate

“…Sulfation by a microbial system is extremely rare. Phenolic hydroxyl groups are good substrates for sulfate conjugation (3), and sulfate conjugates of phenolic hydrocar-bons have been reported (4,14). Zearalenone metabolic studies on turkeys indicated the formation of zearalenone sulfate, but no further structural elucidation was reported (20).…”