Glycosylation of (–)-maackiain byBeauveria bassianaandCunninghamella echinulatavar.elegans

Wei, Yuan; Wang, Ping; Zhang, Zhizhen; Li, Shiyou

doi:10.3109/10242420903497354

Cited by 9 publications

(7 citation statements)

References 20 publications

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“…Summarizing, the course of the biotransformation of isoflavones by three selected filamentous fungi known from their ability to O -glycosylation was investigated. High regioselectivity maintaining low substrate specificity was observed in biotransformation conducted by Beauveria bassiana , which is typical for this species and has been shown in previous studies [ 22 , 23 , 24 , 30 , 31 , 32 ]. Whilst, the substrate specificity of enzymes from Absidia genus is higher.…”

Section: Resultssupporting

confidence: 69%

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

Sordon¹,

Popłoński²,

Tronina³

et al. 2017

Molecules

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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.

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Section: Resultssupporting

confidence: 69%

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

Sordon¹,

Popłoński²,

Tronina³

et al. 2017

Molecules

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“…bassiana , which resulted in obtaining a 4′-methylglucose derivative at a high yield (93%). This leads to the conclusion that 4′-methylglycosylation is a two-step process [ 32 ].…”

Section: Resultsmentioning

confidence: 99%

Glycosylation of 6-methylflavone by the strain Isaria fumosorosea KCH J2

et al. 2017

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Entomopathogenic fungi are known for their ability to carry out glycosylation of flavonoids, which usually results in the improvement of their stability and bioavailability. In this study we used a newly isolated strain of the entomopathogenic filamentous fungus Isaria fumosorosea KCH J2 as a biocatalyst. Our aim was to evaluate its ability to carry out the biotransformation of flavonoids and to obtain new flavonoid derivatives. The fungus was isolated from a spider’s carcass and molecularly identified using analysis of the ITS1-ITS2 rDNA sequence. As a result of biotransformation of 6-methylflavone two new products were obtained: 6-methylflavone 8-O-β-D-(4”-O-methyl)-glucopyranoside and 6-methylflavone 4’-O-β-D-(4”-O-methyl)-glucopyranoside. Chemical structures of the products were determined based on spectroscopic methods (1H NMR, 13C NMR, COSY, HMBC, HSQC). Our research allowed us to discover a new species of filamentous fungus capable of carrying out glycosylation reactions and proved that I. fumosorosea KCH J2 is an effective biocatalyst for glycosylation of flavonoid compounds. For the first time we describe biotransformations of 6-methylflavone and the attachment of the sugar unit to the flavonoid substrate having no hydroxyl group. The possibility of using flavonoid aglycones is often limited by their low bioavailability due to poor solubility in water. The incorporation of a sugar unit improves the physical properties of tested compounds and thus increases the chance of using them as pharmaceuticals.

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“…It is able to catalyze wide range of reactions including hydroxylation, oxidation, reduction and hydrolysis [ 39 ]. It is also known that B. bassiana catalyzes reaction of glycosylation of numerous compounds by attaching 4- O -methylated derivative of glucopyranose to the substrate molecule [ 40 , 41 , 42 , 43 , 44 ]. Our previous studies showed that conjugation of 4- O -methyl-glucopyranose with prenylated and none-prenylated flavonoids was the major reaction in case of biotransformation conducted by B. bassiana [ 7 , 12 , 13 , 15 , 27 ] .…”

Section: Resultsmentioning

confidence: 99%

The Influence of Glycosylation of Natural and Synthetic Prenylated Flavonoids on Binding to Human Serum Albumin and Inhibition of Cyclooxygenases COX-1 and COX-2

et al. 2017

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The synthesis of different classes of prenylated aglycones (α,β-dihydroxanthohumol (2) and (Z)-6,4’-dihydroxy-4-methoxy-7-prenylaurone (3)) was performed in one step reactions from xanthohumol (1)—major prenylated chalcone naturally occurring in hops. Obtained flavonoids (2–3) and xanthohumol (1) were used as substrates for regioselective fungal glycosylation catalyzed by two Absidia species and Beauveria bassiana. As a result six glycosides (4–9) were formed, of which four glycosides (6–9) have not been published so far. The influence of flavonoid skeleton and the presence of glucopyranose and 4-O-methylglucopyranose moiety in flavonoid molecule on binding to main protein in plasma, human serum albumin (HSA), and inhibition of cyclooxygenases COX-1 and COX-2 were investigated. Results showed that chalcone (1) had the highest binding affinity to HSA (8.624 × 104 M−1) of all tested compounds. It has also exhibited the highest inhibition of cyclooxygenases activity, and it was a two-fold stronger inhibitor than α,β-dihydrochalcone (2) and aurone (3). The presence of sugar moiety in flavonoid molecule caused the loss of HSA binding activity as well as the decrease in inhibition of cyclooxygenases activity.

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Glycosylation of (–)-maackiain byBeauveria bassianaandCunninghamella echinulatavar.elegans

Cited by 9 publications

References 20 publications

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

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

Glycosylation of 6-methylflavone by the strain Isaria fumosorosea KCH J2

The Influence of Glycosylation of Natural and Synthetic Prenylated Flavonoids on Binding to Human Serum Albumin and Inhibition of Cyclooxygenases COX-1 and COX-2

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