Abstract
Entomopathogenic filamentous fungi of the genus Isaria are effective biocatalysts in the biotransformation of flavonoids as well as steroids. In the present study, the species Isaria fumosorosea and Isaria farinosa isolated from the environment were used. Their catalytic capacity to carry out biotransformations of flavones—unsubstituted, with hydroxy- and amino-substituents as well as a hydroxylated isoflavone—was investigated. Biotransformations of flavone, 5-hydroxyflavone, 6-hydroxyflavone, 7-hydroxyflavone, and daidzein resulted in the formation of O-methylglucosides, in the case of flavone and 5-hydroxyflavone with additional hydroxylations. 7-Aminoflavone was transformed into two acetamido derivatives. The following products were obtained: From flavone–flavone 2′-O-β-d-(4′′-O-methyl)-glucopyranoside, flavone 4′-O-β-d-(4′′-O-methyl)-glucopyranoside and 3′-hydroxyflavone 4′-O-β-d-(4′′-O-methyl)-glucopyranoside; from 5-hydroxyflavone–5-hydroxyflavone 4′-O-β-d-(4′′-O-methyl)-glucopyranoside; from 6-hydroxyflavone–flavone 6-O-β-d-(4′′-O-methyl)-glucopyranoside; from 7-hydroxyflavone–flavone 7-O-β-d-(4′′-O-methyl)-glucopyranoside; from daidzein–daidzein 7-O-β-d-(4′′-O-methyl)-glucopyranoside; and from 7-aminoflavone–7-acetamidoflavone and 7-acetamido-4′-hydroxyflavone. Seven of the products obtained by us have not been previously reported in the literature.
Highlights
Flavonoid compounds are used in pharmacy [1] and the food industry [2], and their effectiveness in the prevention and treatment of a number of diseases, including civilization diseases, is confirmed by many studies both in vitro on cell lines and in vivo [3,4,5,6,7,8]
The majority of flavonoid compounds that are taken along with the diet pass to the large intestine, where they undergo intense bacterial metabolism [9,12]. The effect of these transformations is often the creation of products with higher activity than the starting compound. This is the case of soy isoflavones, which can be metabolized to equol—a compound with significantly higher estrogenic activity [13]
The main aim of this study was to evaluate the catalytic capacity of Isaria fumosorosea KCH J2, I. farinosa J1.4, I. farinosa J1.6 and I. farinosa KW1.2 to carry out biotransformations of flavone, 5-hydroxyflavone, 6-hydroxyflavone, 7-hydroxyflavone, daidzein, and 7-aminoflavone
Summary
Flavonoid compounds are used in pharmacy [1] and the food industry [2], and their effectiveness in the prevention and treatment of a number of diseases, including civilization diseases, is confirmed by many studies both in vitro on cell lines and in vivo [3,4,5,6,7,8]. The majority of flavonoid compounds that are taken along with the diet pass to the large intestine, where they undergo intense bacterial metabolism [9,12] The effect of these transformations is often the creation of products with higher activity than the starting compound. This is the case of soy isoflavones, which can be metabolized to equol—a compound with significantly higher estrogenic activity [13]
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