Microbial Transformation of 14‐Anhydrodigoxigenin by <i>Alternaria alternata</i>

Liu, Jimei; Tang, Wanxia; Chen, Ridao; Dai, Jungui

doi:10.1002/cbdv.201500024

Cited by 3 publications

(3 citation statements)

References 27 publications

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“…Steroids (compounds 14 to 16) (see Fig. S3 in the supplemental material) were purchased from Sigma-Aldrich Co. LLC (St. Louis, MO, USA), and compound 17 was isolated previously by our laboratory (32). UDP-Glc, UDP-GA, and UDP-Gal were purchased from SigmaAldrich Co. LLC (St. Louis, MO, USA).…”

Section: Methodsmentioning

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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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: Methodsmentioning

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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“…C-11 and C-12 oxygenations are more common in steroid chemistry; however, C-8 is at an encumbered position on the steroid skeleton, and modification of this stereocenter is rare due to steric hindrance. Based on the literature, only Alternaria alternata and Corynespora cassiicada CYP450s are capable of performing this unique oxygenation. , …”

Section: Resultsmentioning

confidence: 99%

“…Based on the literature, only Alternaria alternata and Corynespora cassiicada CYP450s are capable of performing this unique oxygenation. 48,49 The other striking reaction occurring in compound 1 was epoxidation at the Δ 5 (6) olefinic bond to afford 15. Even though there are several reports of microbial 50−53 or semisynthetic 54,55 epoxidation products of steroids, this is the first study demonstrating a Δ 5 (6) epoxidation on a steroidal skeleton by a microbial enzyme system.…”

Section: Journal Of Natural Productsmentioning

confidence: 99%

Biotransformation of Neoruscogenin by the Endophytic Fungus Alternaria eureka

Özçınar

Tag̀²,

Yusufoğlu

et al. 2018

J. Nat. Prod.

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Biotransformation of neoruscogenin (NR, 1, spirosta-5,25(27)-diene-1β,3β-diol), the major bioactive sapogenin of Ruscus preparations, was carried out with the endophytic fungus Alternaria eureka. Fourteen new biotransformation products (2-15) were isolated, and their structures were elucidated by NMR and HRESIMS data analyses. A. eureka affected mainly oxygenation, oxidation, and epoxidation reactions on the B and C rings of the sapogenin to afford compounds 8-15. In addition to these, cleavage of the spiroketal system as in compounds 2-7 and subsequent transformations provided unusual metabolites. This is the first study reporting conversion of the spirostanol skeleton to cholestane-type metabolites 2-5. Additionally, the cleavage of the C-22/C-26 oxygen bridge yielding a furostanol-type steroidal framework and subsequent formation of the epoxy bridge between C-18 and C-22 in 7 was encountered for the first time in steroid chemistry.

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Biotransformation of selected secondary metabolites by Alternaria species and the pharmaceutical, food and agricultural application of biotransformation products

Tembeni,

Idowu,

Benrkia

et al. 2024

Nat. Prod. Bioprospect.

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Biotransformation is a process in which molecules are modified in the presence of a biocatalyst or enzymes, as well as the metabolic alterations that occur in organisms from exposure to the molecules. Microbial biotransformation is an important process in natural product drug discovery as novel compounds are biosynthesised. Additionally, biotransformation products offer compounds with improved efficacy, solubility, reduced cytotoxic and allows for the understanding of structure activity relationships. One of the driving forces for these impeccable findings are associated with the presence of cytochrome P450 monooxygenases that is present in all organisms such as mammals, bacteria, and fungi. Numerous fungal strains have been used and reported for their ability to biotransform different compounds. This review focused on studies using Alternaria species as biocatalysts in the biotransformation of natural product compounds. Alternaria species facilitates reactions that favour stereoselectivity, regioselectivity under mild conditions. Additionally, microbial biotransformation products, their application in food, pharmaceutical and agricultural sector is discussed in this review. Graphical Abstract

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Microbial Transformation of 14‐Anhydrodigoxigenin by Alternaria alternata

Cited by 3 publications

References 27 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

Biotransformation of Neoruscogenin by the Endophytic Fungus Alternaria eureka

Biotransformation of selected secondary metabolites by Alternaria species and the pharmaceutical, food and agricultural application of biotransformation products

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