Metabolism of the Soy Isoflavones Daidzein and Genistein by Fungi Used in the Preparation of Various Fermented Soybean Foods

Chang, Te‐Sheng; Ding, Hsiou-Yu; Tai, Sorgan Shou-Ku; Wu, Ching‐Yi

doi:10.1271/bbb.60573

Cited by 38 publications

(31 citation statements)

References 9 publications

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“…To the best of our knowledge, this is the first report describing catalytic activities of CYP57B3 against genistein and suggesting its possible roles in production of hydroxygenistein during soybean fermentation processes (6,11). Based on sequence comparison, CYP57B3 seems phylogenetically close to a CYP from the plant pathogen Nectria haematococca; a fungus involved in biodegradation of phytoalexin pisatin (22).…”

Section: )mentioning

confidence: 83%

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Construction and Application of a Functional Library of Cytochrome P450 Monooxygenases from the Filamentous Fungus Aspergillus oryzae

Nazir

Ichinose

Wariishi

2011

Appl Environ Microbiol

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A functional library of cytochrome P450 monooxygenases from Aspergillus oryzae (AoCYPs) was constructed in which 121 isoforms were coexpressed with yeast NADPH-cytochrome P450 oxidoreductase in Saccharomyces cerevisiae. Using this functional library, novel catalytic functions of AoCYPs, such as catalytic potentials of CYP57B3 against genistein, were elucidated for the first time. Comprehensive functional screening promises rapid characterization of catalytic potentials and utility of AoCYPs.

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Section: )mentioning

confidence: 83%

“…Genistein is one of the major isoflavonoids found in soybean. Because of its biological and pharmacological activities, genistein derivatives are likely to have various useful applications (6,10,11,15,17,41). When genistein was utilized as a substrate, significant product formations were achieved by S. cerevisiae expressing CYP57B3 (Fig.…”

mentioning

confidence: 99%

Construction and Application of a Functional Library of Cytochrome P450 Monooxygenases from the Filamentous Fungus Aspergillus oryzae

Nazir

Ichinose

Wariishi

2011

Appl Environ Microbiol

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“…FSeS and FSS are prepared by fermenting sesame seeds or soybeans, respectively, with Aspergillus oryzae and other starters at 30℃ for over 180 d. Several studies have reported that FSS has many beneficial properties [1][2][3][4][5][6][7][8][9]. During soy sauce fermentation, the soy isoflavones daidzin and genistin are transformed into daidzein and genistein, respectively, by Asperillus fungi [28,29]. In addition, sesame seeds used to make sesame sauce contain high levels of sesamin and sesaminol along with their glycosides [30,31].…”

Section: Discussionmentioning

confidence: 99%

Antioxidative effects of fermented sesame sauce against hydrogen peroxide-induced oxidative damage in LLC-PK1 porcine renal tubule cells

Song

Choi²,

Seo³

et al. 2014

Nutr Res Pract

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BACKGROUND/OBJECTIVES:This study was performed to investigate the in vitro antioxidant and cytoprotective effects of fermented sesame sauce (FSeS) against hydrogen peroxide (H2O2)-induced oxidative damage in renal proximal tubule LLC-PK1 cells. MATERIALS/METHODS: 1,1-diphenyl-2-picrylhydrazyl (DPPH), hydroxyl radical (• OH), and H2O2 scavenging assay was used to evaluate the in vitro antioxidant activity of FSeS. To investigate the cytoprotective effect of FSeS against H2O2-induced oxidative damage in LLC-PK1 cells, the cellular levels of reactive oxygen species (ROS), lipid peroxidation, and endogenous antioxidant enzymes including catalase (CAT), superoxide dismutase (SOD), and glutathione peroxidase (GSH-px) were measured. RESULTS: The ability of FSeS to scavenge DPPH,• OH and H2O2 was greater than that of FSS and AHSS. FSeS also significantly inhibited H2O2-induced (500 μM) oxidative damage in the LLC-PK1 cells compared to FSS and AHSS (P < 0.05). Following treatment with 100 μg/mL of FSeS and FSS to prevent H2O2-induced oxidation, cell viability increased from 56.7% (control) to 83.7% and 75.6%, respectively. However, AHSS was not able to reduce H2O2-induced cell damage (viability of the AHSS-treated cells was 54.6%). FSeS more effectively suppressed H2O2-induced ROS generation and lipid peroxidation compared to FSS and AHSS (P < 0.05). Compared to the other sauces, FSeS also significantly increased cellular CAT, SOD, and GSH-px activities and mRNA expression (P < 0.05). CONCULUSIONS: These results from the present study suggest that FSeS is an effective radical scavenger and protects against H2O2-induced oxidative damage in LLC-PK1 cells by reducing ROS levels, inhibiting lipid peroxidation, and stimulating antioxidant enzyme activity.

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“…The microorganism used is a key point for this study since not all of the fungal strains from dou-chi, miso, sake, soy sauce or sufu have the ability to process the biotransformation (Chang et al, 2007a). Even among the Aspergillus species, only some can metabolize daidzin; for example, Aspergillus sojae, Aspergillus tamari and Aspergillus oryzae.…”

Section: -Hydroxydaidzein From Soybean Fermented With Aspergillus Samentioning

confidence: 99%

“…Even among the Aspergillus species, only some can metabolize daidzin; for example, Aspergillus sojae, Aspergillus tamari and Aspergillus oryzae. In this study, we used Aspergillus oryzae BCRC 32288 since its transformability was the best in the previous report (Chang et al, 2007a).…”

Section: -Hydroxydaidzein From Soybean Fermented With Aspergillus Samentioning

confidence: 99%

Production of 8-hydroxydaidzein Polyphenol Using Biotransformation by <i>Aspergillus oryzae</i>

Chang

Lin

et al. 2015

FSTR

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Several polyphenolic compounds which were derived from the fermented soybean had been identified and investigated for their potential effects on some diseases. However, such a biotransformation phenomenon is seldom discussed and has not been studied by using submerged culture with isoflavone, such as pure daidzein, as a substrate.In this study, the conditions for hydroxylation of pure daidzein into 8-hydroxydaidzein by Aspergillus oryzae were systemically investigated. Our results indicated that the optimal culture conditions for the hydroxylation were 200 rpm and pH 6. Moreover, the production was significantly increased 57.4% by an optimized concentration of 3 g/L MgSO 4 . On the other hand, 77.8% high biotransformation efficiency of 8-hydroxydaidzein could be obtained by providing pure daidzein; that can avoid many derived polyphenolic compounds were generated by isoflavone biotransformation. Our results suggest that the biotransformation of 8-hydroxydaidzein can be performed through a highly selected catalysis under specified conditions using certain microorganisms.

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Metabolism of the Soy Isoflavones Daidzein and Genistein by Fungi Used in the Preparation of Various Fermented Soybean Foods

Cited by 38 publications

References 9 publications

Construction and Application of a Functional Library of Cytochrome P450 Monooxygenases from the Filamentous Fungus Aspergillus oryzae

Construction and Application of a Functional Library of Cytochrome P450 Monooxygenases from the Filamentous Fungus Aspergillus oryzae

Antioxidative effects of fermented sesame sauce against hydrogen peroxide-induced oxidative damage in LLC-PK1 porcine renal tubule cells

Production of 8-hydroxydaidzein Polyphenol Using Biotransformation by <i>Aspergillus oryzae</i>

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