Microbial Glycosylation of Daidzein, Genistein and Biochanin A: Two New Glucosides of Biochanin A

Abstract

Biotransformation of daidzein, genistein and biochanin A by three selected filamentous fungi was investigated. As a result of biotransformations, six glycosylation products were obtained. Fungus Beauveria bassiana converted all tested isoflavones to 4″-O-methyl-7-O-glucosyl derivatives, whereas Absidia coerulea and Absidia glauca were able to transform genistein and biochanin A to genistin and sissotrin, respectively. In the culture of Absidia coerulea, in addition to the sissotrin, the product of glucosylation at position 5 was formed. Two of the obtained compounds have not been published so far: 4″-O-methyl-7-O-glucosyl biochanin A and 5-O-glucosyl biochanin A (isosissotrin). Biotransformation products were obtained with 22%–40% isolated yield.

Methylglucosylation of aromatic amino and phenolic moieties of drug-like biosynthons by combinatorial biosynthesis

“…S15B and Table S7.4). The observed regioselectivity for OH-5 in RALs and radilarin (17) is coincident with a stronger acidity of that group [e.g., for DLD (1), a pK a of 8.7 for OH-5 vs. 9.8 for OH-3]. However, the preference of the GT for OH-7 in lasilarin (18) is contrary to a weaker acidity of that group (e.g., pK a of 8.9 for OH-7 vs. 7.8 for OH-5 in 18).…”

“…The entomopathogenic ascomycetous fungus Beauveria bassiana is a useful biocatalyst due to its ability to catalyze various biotransformations, including methylation, hydroxylation, and oxidation (11)(12)(13)(14)(15)(16)(17)(18)(19). It also readily glycosylates a large variety of phenolic compounds, such as flavonoids, anthraquinones, and other polyketides (15-17, 20, 21), including benzenediol lactones (BDLs), such as curvularin (21) (14 in SI Appendix, Fig.…”

“…Although "druglikeness" for oral drug candidates is a multidimensional property, reduced ClogP values (in the range of 2.5-3.0) have been correlated with higher success rates in market introduction due to more favorable drug potency, bioavailability, pharmacokinetics, and toxicity profiles (50). In particular, flavonoid glycosides are often considered more valuable due to their better solubility and stability, although their bioavailability and absorption from the small intestine is variable, and may be influenced by their differential deglycosylation by the intestinal microflora (17,51).…”

Entomopathogenic fungi: unconventional applications

“…For example, M. robertsii and M. brunneum species can degrade nonylphenols, triazines, tin compounds, synthetic estrogen, hydrocarbons, and even industrial dyes. These microorganisms also interact with heavy Sordon et al (2017) metals, which sometimes adversely affect their growth or hyphae morphology; however, these fungi possess the ability to remove heavy metals from the environment, for example, from contaminated waters (zinc, copper, cadmium, nickel, and chromium) and indirectly by improving the phytoremediation properties of plants (copper, manganese, and zinc). On the basis of this current review article, the authors conclude that EPF have great potential in the biosynthesis of biologically active compounds used in medicine, for example, hydroxylated steroids and glycated flavonoids or for bioproduction of silver nanoparticles with antibacterial and antifungal properties.…”

“…These are glycosides with O-and C-glycosidic bonds connecting the base with sugar residues (Dymarska et al 2018a, b;Dou et al 2019), including most often glucose, rhamnose, galactose, xylose, and arabinose (Yang et al 2018). It is believed that the sugar group of flavonoids is the main factor affecting the absorption of these compounds by the human body (Sordon et al 2017). There are six classes of flavonoids: flavones, isoflavones, flavanones, flavanols, flavanonols, and flavan-3-ols.…”