Microbial metabolism. Part 13. Metabolites of hesperetin

Herath, Wimal; Khan, Ikhlas A.

doi:10.1016/j.bmcl.2011.08.004

Cited by 7 publications

(7 citation statements)

References 31 publications

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“…Ibrahim et al [ 66 ] reported that incubation of kaempferol with Cunninghamella blakesleeana (ATCC 8688A) led to the production of kaempferol-4'-sulfate. A similar result was observed by Herath et al [ 80 ] indicating that Mucor ramannianus (ATCC 2628) was able to convert hesperitin into hesperetin-7-sulfate.…”

Section: Microbial Metabolism Of Flavonoids During Fermentationsupporting

confidence: 88%

“…Sulfate conjugation is a major pathway for the phase II metabolism of phenolic compounds in humans via the bile using arylsulphotransferase, originating from human colonic bacteria [ 1 ]. However, recent studies have shown that bioconversion of phenolic compounds into their sulfated conjugated form could also be performed by a few fungal strains including Cunninghamella echinulata [ 78 ], Cunninghamella blakesleeana [ 66 ], Streptomyces fulvissimus [ 2 ], and Mucor ramannianus [ 80 ]. Rutin incubated with Cunninghamella echinulata induced rutin sulfate [ 78 ].…”

Section: Microbial Metabolism Of Flavonoids During Fermentationmentioning

confidence: 99%

See 1 more Smart Citation

Improved Release and Metabolism of Flavonoids by Steered Fermentation Processes: A Review

Huynh

Camp

Smagghe

et al. 2014

IJMS

178

120

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This paper provides an overview on steered fermentation processes to release phenolic compounds from plant-based matrices, as well as on their potential application to convert phenolic compounds into unique metabolites. The ability of fermentation to improve the yield and to change the profile of phenolic compounds is mainly due to the release of bound phenolic compounds, as a consequence of the degradation of the cell wall structure by microbial enzymes produced during fermentation. Moreover, the microbial metabolism of phenolic compounds results in a large array of new metabolites through different bioconversion pathways such as glycosylation, deglycosylation, ring cleavage, methylation, glucuronidation and sulfate conjugation, depending on the microbial strains and substrates used. A whole range of metabolites is produced, however metabolic pathways related to the formation and bioactivities, and often quantification of the metabolites are highly underinvestigated. This strategy could have potential to produce extracts with a high-added value from plant-based matrices. OPEN ACCESSInt. J. Mol. Sci. 2014, 15 19370

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Section: Microbial Metabolism Of Flavonoids During Fermentationsupporting

confidence: 88%

Section: Microbial Metabolism Of Flavonoids During Fermentationmentioning

confidence: 99%

Improved Release and Metabolism of Flavonoids by Steered Fermentation Processes: A Review

Huynh

Camp

Smagghe

et al. 2014

IJMS

178

120

View full text Add to dashboard Cite

show abstract

“…The structures of the obtained compounds were confirmed by NMR spectra analysis. Spectroscopic data of the products 6 – 12 are in agreement with literature data. ,,− …”

Section: Methodssupporting

confidence: 87%

Regioselective ortho-Hydroxylations of Flavonoids by Yeast

Sordon

Anna

Popłoński

et al. 2016

J. Agric. Food Chem.

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Natural flavonoids, such as naringenin, hesperetin, chrysin, apigenin, luteolin, quercetin, epicatechin, and biochanin A, were subjected to microbiological transformations by Rhodotorula glutinis. Yeast was able to regioselectively C-8 hydroxylate hesperetin, luteolin, and chrysin. Naringenin was transformed to 8- and 6-hydroxyderivatives. Quercetin, epicatechin, and biochanin A did not undergo biotransformation. A metabolic pathway for the degradation of chrysin has been elucidated. The metabolism of chrysin proceeds via an initial C-8 hydroxylation to norwogonin, followed by A-ring cleavage to 4-hydroxy-6-phenyl-2H-pyran-2-one.

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“…However, sulfation in microbial systems is rare and reports on this topic are limited. So far, in addition to the list of microorganisms reported by Khan [22][23][24][25][26], several fungi including Absidia coerulea [40],…”

Section: Microbial Transformation Of Licochalcones a B C H And Xanthohumol By A Coeruleamentioning

confidence: 99%

“…Such processes can provide sufficient amounts of metabolites for structure elucidation and pharmacological activity evaluation [21]. Khan and colleagues have reported that Absidia glauca [22], Aspergillus alliaceus [23], Beauveria bassiana [24], Chaetomium cochlioides, Cunninghamella blakesleeana [23], Cunninghamella echinulata [25], Mortierella zonata [23], and Mucor ramannianus [26] could transform the flavones and flavanones to their corresponding sulfated metabolites. Thus, biotransformation conducted by microorganisms could be used as a simple and efficient method for obtaining not only phase I but also phase II metabolites of chalcones [20].…”

Section: Introductionmentioning

confidence: 99%

Microbial Conjugation Studies of Licochalcones and Xanthohumol

Han

Xiao

Lee

2021

IJMS

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Microbial conjugation studies of licochalcones (1–4) and xanthohumol (5) were performed by using the fungi Mucor hiemalis and Absidia coerulea. As a result, one new glucosylated metabolite was produced by M. hiemalis whereas four new and three known sulfated metabolites were obtained by transformation with A. coerulea. Chemical structures of all the metabolites were elucidated on the basis of 1D-, 2D-NMR and mass spectroscopic data analyses. These results could contribute to a better understanding of the metabolic fates of licochalcones and xanthohumol in mammalian systems. Although licochalcone A 4′-sulfate (7) showed less cytotoxic activity against human cancer cell lines compared to its substrate licochalcone A, its activity was fairly retained with the IC50 values in the range of 27.35–43.07 μM.

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Microbial metabolism. Part 13. Metabolites of hesperetin

Cited by 7 publications

References 31 publications

Improved Release and Metabolism of Flavonoids by Steered Fermentation Processes: A Review

Improved Release and Metabolism of Flavonoids by Steered Fermentation Processes: A Review

Regioselective ortho-Hydroxylations of Flavonoids by Yeast

Microbial Conjugation Studies of Licochalcones and Xanthohumol

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