Efficiently regioselective glucosylation of estrogen analogues mediated by fungus Rhizopus oryzae AS 3.2380

Li, Ping; Sun, Cheng‐Peng; Wang, Yan; Wang, Shumei; Yan, Chunyan; Deng, Sa; Huo, Xiaokui; Feng, Lei; Wang, Chao; Tian, Ye; Zhang, Baojing; Ma, Xiaochi

doi:10.1016/j.catcom.2017.04.027

Cited by 6 publications

(5 citation statements)

References 19 publications

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“…Steroid glycosides are known as biotransformation products obtained from the cultures of Syncephalastrum racemosum AS 3.264 26 , Mucor hiemalis 27 and many plants 28 . Glucosyloestrogens were obtained in the cultures of Rhizopus oryzae AS 3.2380 14 and microalgae of the genus Selenastrum 15 . In the culture of R .…”

Section: Resultsmentioning

confidence: 99%

“…Only in a few studies there were observed glycosides of steroid compounds formed as a result of biotransformation. Regioselective glucosylation of estrogen analogues mediated by the fungus Rhizopus oryzae AS 3.2380 14 and hydroxylation with glucosylation by microalgae Selenastrum capricornutum strains 15 were described. In our previous studies, we presented the Isaria fumosorosea KCh J2 strain, which provides glycosylation of flavonoid compounds 16–18 .…”

Section: Introductionmentioning

confidence: 99%

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Cascade biotransformation of estrogens by Isaria fumosorosea KCh J2

Kozłowska

Dymarska

Kostrzewa-Susłow

et al. 2019

Sci Rep

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Estrone, estradiol, ethynylestradiol and estrone 3-methyl ether underwent a biotransformation process in the submerged culture of Isaria fumosorosea KCh J2. Estrone was transformed into seven metabolites, four of which were glycosylated. Estradiol was selectively glycosylated at C-3 and then transformed to D-ring lactone. Ethynylestradiol was coupled with methylglucoside and 6β-hydroxyderivative was obtained. Estrone 3-methyl ether was not transformed indicating that a free hydroxyl group at C-3 is necessary for glycosylation. Baeyer–Villiger oxidation combined with hydroxylation and glycosylation was observed. All glycosides obtained in this study are 3- O -β-methylglucosides.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Cascade biotransformation of estrogens by Isaria fumosorosea KCh J2

Kozłowska

Dymarska

Kostrzewa-Susłow

et al. 2019

Sci Rep

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“…For example, R. microsporus converted zearalenone to its more soluble 4-β-D-glucopyranoside [42]. Of note, the presence of glucosyltransferases in the genus Rhizopus is not scarce, and these enzymes are used, e.g., in estrogen biotransformation [43].…”

Section: Discussionmentioning

confidence: 99%

“…J. Fungi 2020, 6, x FOR PEER REVIEW 7 of 10 presence of glucosyltransferases in the genus Rhizopus is not scarce, and these enzymes are used, e.g., in estrogen biotransformation [43]. RHF itself is an analytically difficult molecule for direct detection in patients with invasive mucormycoses, and its metabolic fate in the host body remains obscure.…”

Section: Discussionmentioning

confidence: 99%

Rhizoferrin Glycosylation in Rhizopus microsporus

Škríba

Patil

Hubáček

et al. 2020

JoF

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Rhizopus spp. are the most common etiological agents of mucormycosis, causing over 90% mortality in disseminated infections. The diagnosis relies on histopathology, culture, and/or polymerase chain reaction. For the first time, the glycosylation of rhizoferrin (RHF) was described in a Rhizopus microsporus clinical isolate by liquid chromatography and accurate tandem mass spectrometry. The fermentation broth lyophilizate contained 345.3 ± 13.5, 1.2 ± 0.03, and 0.03 ± 0.002 mg/g of RHF, imido-RHF, and bis-imido-RHF, respectively. Despite a considerable RHF secretion rate, we did not obtain conclusive RHF detection from a patient with disseminated mucormycosis caused by the same R. microsporus strain. We hypothesize that parallel antimycotic therapy, RHF biotransformation, and metabolism compromised the analysis. On the other hand, the full profile of posaconazole metabolites was retrieved by our in house software CycloBranch.

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“…Middle chromatogram isolated (MCI) gel, usually combined with column chromatography, has been widely used in the purication and enrichment of complex components in TTM. [20][21][22] Herein, we used a mid-pressure chromatographic tower containing the MCI gel as the preparation column to connect with the preparation liquid to construct a medium pressure preparation chromatographic separation system for the pretreatment of the crude extract. Next, ve different types of preparation columns, namely HT-ODS-P, ZORBAX SB-C18, ZORBAX SB-CN, ZORBAX SB-AQ and Xamide, were selected to analyze the samples, and nally the ZORBAX SB-AQ column with the best separation effect was selected for the nal preparation and separation.…”

Section: Introductionmentioning

confidence: 99%