Microbial transformation of silybin by Trichoderma koningii

Kim, Hyun Jung; Park, Hae-Suk; Lee, Ik‐Soo

doi:10.1016/j.bmcl.2005.11.022

Cited by 18 publications

(12 citation statements)

References 10 publications

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“…Various fungi have been proven to have the ability to convert structurally different foreign phenolics into their corresponding glycosides with high yields (17)(18)(19)(20)(21)(22). This glycosylation capability might be derived from the mechanism of self-protection from diverse xenobiotics.…”

Section: Discussionmentioning

confidence: 99%

“…For example, xanthohumol is glycosylated by Absidia coerulea AM93, Rhizopus nigricans UFP701, and Beauveria bassiana AM446 (17,18); quercetin, kaempferol, and isorhamnetin can be converted to their glycosides by Cunninghamella elegans ATCC 9245 (19); and Trichoderma koningii KTCC 6042 glycosylates silybins A and B to silybin A 3-O-␤-glucopyranoside, silybin A 7-O-␤-glucopyranoside, silybin B 3-O-␤-glucopyranoside, and silybin B 7-O-␤-glucopyranoside, respectively (20,21). However, the genes encoding P-UGTs in fungi have not yet been identified.…”

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confidence: 99%

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Two Novel Fungal Phenolic UDP Glycosyltransferases from Absidia coerulea and Rhizopus japonicus

Xie

Dou

Chen

et al. 2017

Appl Environ Microbiol

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In the present study, two novel phenolic UDP glycosyltransferases (PUGTs), UGT58A1 and UGT59A1, which can transfer sugar moieties from active donors to phenolic acceptors to generate corresponding glycosides, were identified in the fungal kingdom. UGT58A1 (from Absidia coerulea) and UGT59A1 (from Rhizopus japonicas) share a low degree of homology with known UGTs from animals, plants, bacteria, and viruses. These two P-UGTs are membrane-bound proteins with an N-terminal signal peptide and a transmembrane domain at the C terminus. Recombinant UGT58A1 and UGT59A1 are able to regioselectively and stereoselectively glycosylate a variety of phenolic aglycones to generate the corresponding glycosides. Phylogenetic analysis revealed the novelty of UGT58A1 and UGT59A1 in primary sequences in that they are distantly related to other UGTs and form a totally new evolutionary branch. Moreover, UGT58A1 and UGT59A1 represent the first members of the UGT58 and UGT59 families, respectively. Homology modeling and mutational analysis implied the sugar donor binding sites and key catalytic sites, which provided insights into the catalytic mechanism of UGT58A1. These results not only provide an efficient enzymatic tool for the synthesis of bioactive glycosides but also create a starting point for the identification of P-UGTs from fungi at the molecular level.IMPORTANCE Thus far, there have been many reports on the glycosylation of phenolics by fungal cells. However, no P-UGTs have ever been identified in fungi. Our study identified fungal P-UGTs at the molecular level and confirmed the existence of the UGT58 and UGT59 families. The novel sequence information on UGT58A1 and UGT59A1 shed light on the exciting and new P-UGTs hiding in the fungal kingdom, which would lead to the characterization of novel P-UGTs from fungi. Molecular identification of fungal P-UGTs not only is theoretically significant for a better understanding of the evolution of UGT families but also can be applied as a powerful tool in the glycodiversification of bioactive natural products for drug discovery.

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Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

Two Novel Fungal Phenolic UDP Glycosyltransferases from Absidia coerulea and Rhizopus japonicus

Xie

Dou

Chen

et al. 2017

Appl Environ Microbiol

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“…Although several researchers worldwide have chemically investigated T. diversifolia, compound 2 was isolated only from a Brazilian population [2]. As already mentioned, it should be emphasized that the main enzymatic reactions that Aspergillus promotes in STLs are hydrogenation, hydroxylation, reduction, and acetylation [6,11,15,17,20,27,29,31,39,40]. Interestingly, we have uncovered an unusual epoxidation between C4 and C5; a methoxy group was added at C1, and a C1,C10 ether bridge was formed in the 10-membered ring of 1.…”

Section: Resultsmentioning

confidence: 99%

“…In addition, it is a useful tool for the structural modification of bioactive natural products and the study of natural product metabolism [15,16]. Moreover, some microorganisms can transform drugs in a similar way to mammals, and the utilization of microbial systems as models which mimic the metabolism of drugs in humans has received considerable attention [7,16].…”

Section: Introductionmentioning

confidence: 99%

Microbial transformation of the sesquiterpene lactone tagitinin C by the fungus Aspergillus terreus

Rocha

Pupo

Antonucci³

et al. 2012

Journal of Industrial Microbiology and Biotechnology

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The biotransformation of the sesquiterpene lactone tagitinin C by the fungus Aspergillus terreus MT 5.3 yielded a rare derivative that was elucidated by spectrometric methods. The fungus led to the formation of a different product through an unusual epoxidation reaction between C4 and C5, formation of a C3,C10 ether bridge, and a methoxylation of the C1 of tagitinin C. The chemical structure of the product, namely 1b-methoxy-3a-hydroxy-3,10b-4,5a-diepoxy-8b-isobutyroyloxygermacr-11(13)-en6a,12-olide, is the same as that of a derivative that was recently isolated from the flowers of a Brazilian population of Mexican sunflower (Tithonia diversifolia), which is the source of the substrate tagitinin C. The in vitro cytotoxic activity of the substrate and the biotransformed product were evaluated in HL-60 cells using an MTT assay, and both compounds were found to be cytotoxic. We show that soil fungi may be useful in the biotransformation of sesquiterpene lactones, thereby leading to unusual changes in their chemical structures that may preserve or alter their biological activities, and may also mimic plant biosynthetic pathways for production of secondary metabolites.

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“…Biotransformation of silybin by microbes can be useful methods to achieve selective conversions of compounds to derivatives which are difficult to produce synthetically. Silybin is a major active constituent of silymarin, which have hepatoprotective and antioxidant activity (Kim et al, 2006a).…”

Section: Microbial Glycosylation Of Flavonoidsmentioning

confidence: 99%

Microbial Glycosylation of Flavonoids

Sordon

Popłoński

Huszcza

2016

Polish Journal of Microbiology

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A b s t r a c tFlavonoids constitute a large group of polyphenolic compounds naturally found in plants, which have a wide range of biological activity. Although flavonoids are beneficial to human health, their application is limited by their low bioavailability and poor water-solubility. Therefore, recently there has been a particular interest in glycosylated forms of flavonoids, which usually are better soluble, more stable, and more functional compared to their aglycones. Microbial transformation of natural flavonoids may be an attractive way of receiving their glycosylated derivatives in amounts sufficient for the research on the effect of glycoside group on compound properties and for further application of these compounds as ingredients of dietary supplements and pharmaceuticals.K e y w o r d s:

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Microbial transformation of silybin by Trichoderma koningii

Cited by 18 publications

References 10 publications

Two Novel Fungal Phenolic UDP Glycosyltransferases from Absidia coerulea and Rhizopus japonicus

Two Novel Fungal Phenolic UDP Glycosyltransferases from Absidia coerulea and Rhizopus japonicus

Microbial transformation of the sesquiterpene lactone tagitinin C by the fungus Aspergillus terreus

Microbial Glycosylation of Flavonoids

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