Literature DB >> 18539813

Conversion of daidzein and genistein by an anaerobic bacterium newly isolated from the mouse intestine.

Anastasia Matthies1, Thomas Clavel, Michael Gütschow, Wolfram Engst, Dirk Haller, Michael Blaut, Annett Braune.   

Abstract

The metabolism of isoflavones by gut bacteria plays a key role in the availability and bioactivation of these compounds in the intestine. Daidzein and genistein are the most common dietary soy isoflavones. While daidzein conversion yielding equol has been known for some time, the corresponding formation of 5-hydroxy-equol from genistein has not been reported previously. We isolated a strictly anaerobic bacterium (Mt1B8) from the mouse intestine which converted daidzein via dihydrodaidzein to equol as well as genistein via dihydrogenistein to 5-hydroxy-equol. Strain Mt1B8 was a gram-positive, rod-shaped bacterium identified as a member of the Coriobacteriaceae. Strain Mt1B8 also transformed dihydrodaidzein and dihydrogenistein to equol and 5-hydroxy-equol, respectively. The conversion of daidzein, genistein, dihydrodaidzein, and dihydrogenistein in the stationary growth phase depended on preincubation with the corresponding isoflavonoid, indicating enzyme induction. Moreover, dihydrogenistein was transformed even more rapidly in the stationary phase when strain Mt1B8 was grown on either genistein or daidzein. Growing the cells on daidzein also enabled conversion of genistein. This suggests that the same enzymes are involved in the conversion of the two isoflavones.

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Year:  2008        PMID: 18539813      PMCID: PMC2519357          DOI: 10.1128/AEM.00555-08

Source DB:  PubMed          Journal:  Appl Environ Microbiol        ISSN: 0099-2240            Impact factor:   4.792


  50 in total

1.  Metabolism of daidzein and genistein by intestinal bacteria.

Authors:  Y C Chang; M G Nair
Journal:  J Nat Prod       Date:  1995-12       Impact factor: 4.050

2.  Identification of phytoestrogens in the urine of male dogs.

Authors:  P E Juniewicz; S Pallante Morell; A Moser; L L Ewing
Journal:  J Steroid Biochem       Date:  1988-12       Impact factor: 4.292

3.  Degradation of quercetin and luteolin by Eubacterium ramulus.

Authors:  A Braune; M Gütschow; W Engst; M Blaut
Journal:  Appl Environ Microbiol       Date:  2001-12       Impact factor: 4.792

4.  Soybean isoflavones: effect of environment and variety on composition.

Authors:  A C Eldridge; W F Kwolek
Journal:  J Agric Food Chem       Date:  1983 Mar-Apr       Impact factor: 5.279

5.  Identification of lignans and phytoestrogens in urine of chimpanzees.

Authors:  H Adlercreutz; P I Musey; T Fotsis; C Bannwart; K Wähälä; T Mäkelä; G Brunow; T Hase
Journal:  Clin Chim Acta       Date:  1986-07-30       Impact factor: 3.786

6.  Anaerobic C-ring cleavage of genistein and daidzein by Eubacterium ramulus.

Authors:  Lilian Schoefer; Ruchika Mohan; Annett Braune; Marc Birringer; Michael Blaut
Journal:  FEMS Microbiol Lett       Date:  2002-03-05       Impact factor: 2.742

7.  Treatment with antibiotics reduces plasma equol concentration in cynomolgus monkeys (Macaca fascicularis).

Authors:  Robert M Blair; Susan E Appt; Adrian A Franke; Thomas B Clarkson
Journal:  J Nutr       Date:  2003-07       Impact factor: 4.798

8.  Variations in metabolism of the soy isoflavonoid daidzein by human intestinal microfloras from different individuals.

Authors:  Fatemeh Rafii; Christy Davis; Miseon Park; Thomas M Heinze; Richard D Beger
Journal:  Arch Microbiol       Date:  2003-05-29       Impact factor: 2.552

9.  Equol, a natural estrogenic metabolite from soy isoflavones: convenient preparation and resolution of R- and S-equols and their differing binding and biological activity through estrogen receptors alpha and beta.

Authors:  Rajeev S Muthyala; Young H Ju; Shubin Sheng; Lee D Williams; Daniel R Doerge; Benita S Katzenellenbogen; William G Helferich; John A Katzenellenbogen
Journal:  Bioorg Med Chem       Date:  2004-03-15       Impact factor: 3.641

10.  A urinary profile study of dietary phytoestrogens. The identification and mode of metabolism of new isoflavonoids.

Authors:  G E Joannou; G E Kelly; A Y Reeder; M Waring; C Nelson
Journal:  J Steroid Biochem Mol Biol       Date:  1995-08       Impact factor: 4.292

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  30 in total

Review 1.  Equol: history, chemistry, and formation.

Authors:  Kenneth D R Setchell; Carlo Clerici
Journal:  J Nutr       Date:  2010-06-02       Impact factor: 4.798

Review 2.  Does equol production determine soy endocrine effects?

Authors:  Dana Shor; Thozhukat Sathyapalan; Stephen L Atkin; Natalie J Thatcher
Journal:  Eur J Nutr       Date:  2012-02-25       Impact factor: 5.614

Review 3.  The Interactions between Polyphenols and Microorganisms, Especially Gut Microbiota.

Authors:  Małgorzata Makarewicz; Iwona Drożdż; Tomasz Tarko; Aleksandra Duda-Chodak
Journal:  Antioxidants (Basel)       Date:  2021-01-28

4.  Identification and expression of genes involved in the conversion of daidzein and genistein by the equol-forming bacterium Slackia isoflavoniconvertens.

Authors:  Christine Schröder; Anastasia Matthies; Wolfram Engst; Michael Blaut; Annett Braune
Journal:  Appl Environ Microbiol       Date:  2013-03-29       Impact factor: 4.792

Review 5.  Isoflavones: estrogenic activity, biological effect and bioavailability.

Authors:  Daniela Cristina Vitale; Cateno Piazza; Barbara Melilli; Filippo Drago; Salvatore Salomone
Journal:  Eur J Drug Metab Pharmacokinet       Date:  2013-03       Impact factor: 2.441

6.  An NADH-Dependent Reductase from Eubacterium ramulus Catalyzes the Stereospecific Heteroring Cleavage of Flavanones and Flavanonols.

Authors:  Annett Braune; Michael Gütschow; Michael Blaut
Journal:  Appl Environ Microbiol       Date:  2019-09-17       Impact factor: 4.792

7.  Isolation of a human intestinal bacterium capable of daidzein and genistein conversion.

Authors:  Anastasia Matthies; Michael Blaut; Annett Braune
Journal:  Appl Environ Microbiol       Date:  2009-01-09       Impact factor: 4.792

Review 8.  The influence of gut microbiota on drug metabolism and toxicity.

Authors:  Houkai Li; Jiaojiao He; Wei Jia
Journal:  Expert Opin Drug Metab Toxicol       Date:  2015-12-10       Impact factor: 4.481

9.  Stereospecific biotransformation of dihydrodaidzein into (3S)-equol by the human intestinal bacterium Eggerthella strain Julong 732.

Authors:  Mihyang Kim; Su-Il Kim; Jaehong Han; Xiu-Ling Wang; Dae-Geun Song; Soo-Un Kim
Journal:  Appl Environ Microbiol       Date:  2009-03-20       Impact factor: 4.792

10.  Gut microbiota composition is correlated to grid floor induced stress and behavior in the BALB/c mouse.

Authors:  Katja Maria Bangsgaard Bendtsen; Lukasz Krych; Dorte Bratbo Sørensen; Wanyong Pang; Dennis Sandris Nielsen; Knud Josefsen; Lars H Hansen; Søren J Sørensen; Axel Kornerup Hansen
Journal:  PLoS One       Date:  2012-10-02       Impact factor: 3.240

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