Literature DB >> 22582059

Identification of a novel dihydrodaidzein racemase essential for biosynthesis of equol from daidzein in Lactococcus sp. strain 20-92.

Yoshikazu Shimada1, Masayuki Takahashi, Norihiro Miyazawa, Yasuhiro Abiru, Shigeto Uchiyama, Haretsugu Hishigaki.   

Abstract

Equol is metabolized from daidzein, a soy isoflavone, by the gut microflora. In this study, we identified a novel dihydrodaidzein racemase (L-DDRC) that is involved in equol biosynthesis in a lactic acid bacterium, Lactococcus sp. strain 20-92, and confirmed that histidine-tagged recombinant L-DDRC (L-DDRC-His) was able to convert both the (R)- and (S)-enantiomers of dihydrodaidzein to the racemate. Moreover, we showed that recombinant L-DDRC-His was essential for in vitro equol production from daidzein by a recombinant enzyme mixture and that efficient in vitro equol production from daidzein was possible using at least four enzymes, including L-DDRC. We also proposed a model of the metabolic pathway from daidzein to equol in Lactococcus strain 20-92.

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Year:  2012        PMID: 22582059      PMCID: PMC3416379          DOI: 10.1128/AEM.00410-12

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


  16 in total

Review 1.  The clinical importance of the metabolite equol-a clue to the effectiveness of soy and its isoflavones.

Authors:  Kenneth D R Setchell; Nadine M Brown; Eva Lydeking-Olsen
Journal:  J Nutr       Date:  2002-12       Impact factor: 4.798

2.  Multiple sequence alignment with the Clustal series of programs.

Authors:  Ramu Chenna; Hideaki Sugawara; Tadashi Koike; Rodrigo Lopez; Toby J Gibson; Desmond G Higgins; Julie D Thompson
Journal:  Nucleic Acids Res       Date:  2003-07-01       Impact factor: 16.971

3.  Basic local alignment search tool.

Authors:  S F Altschul; W Gish; W Miller; E W Myers; D J Lipman
Journal:  J Mol Biol       Date:  1990-10-05       Impact factor: 5.469

4.  Identification of two novel reductases involved in equol biosynthesis in Lactococcus strain 20-92.

Authors:  Yoshikazu Shimada; Masayuki Takahashi; Norihiro Miyazawa; Tadaaki Ohtani; Yasuhiro Abiru; Shigeto Uchiyama; Haretsugu Hishigaki
Journal:  J Mol Microbiol Biotechnol       Date:  2012-01-31

5.  Comparison of isoflavones among dietary intake, plasma concentration and urinary excretion for accurate estimation of phytoestrogen intake.

Authors:  Y Arai; M Uehara; Y Sato; M Kimira; A Eboshida; H Adlercreutz; S Watanabe
Journal:  J Epidemiol       Date:  2000-03       Impact factor: 3.211

6.  Genetic applications of an inverse polymerase chain reaction.

Authors:  H Ochman; A S Gerber; D L Hartl
Journal:  Genetics       Date:  1988-11       Impact factor: 4.562

7.  Enantioselective synthesis of S-equol from dihydrodaidzein by a newly isolated anaerobic human intestinal bacterium.

Authors:  Xiu-Ling Wang; Hor-Gil Hur; Je Hyeon Lee; Ki Tae Kim; Su-Il Kim
Journal:  Appl Environ Microbiol       Date:  2005-01       Impact factor: 4.792

8.  Phytoestrogens modulate binding response of estrogen receptors alpha and beta to the estrogen response element.

Authors:  Drazen Kostelac; Gerhard Rechkemmer; Karlis Briviba
Journal:  J Agric Food Chem       Date:  2003-12-17       Impact factor: 5.279

9.  Metabolism of isoflavones and lignans by the gut microflora: a study in germ-free and human flora associated rats.

Authors:  E Bowey; H Adlercreutz; I Rowland
Journal:  Food Chem Toxicol       Date:  2003-05       Impact factor: 6.023

10.  Purification and partial characterization of the Pyrococcus horikoshii methylmalonyl-CoA epimerase.

Authors:  T A Bobik; M E Rasche
Journal:  Appl Microbiol Biotechnol       Date:  2003-10-29       Impact factor: 4.813

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  25 in total

1.  The Chemistry of Gut Microbial Metabolism of Polyphenols.

Authors:  Jan F Stevens; Claudia S Maier
Journal:  Phytochem Rev       Date:  2016-03-11       Impact factor: 5.374

2.  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 3.  Bacterial species involved in the conversion of dietary flavonoids in the human gut.

Authors:  Annett Braune; Michael Blaut
Journal:  Gut Microbes       Date:  2016-03-10

4.  P212A Mutant of Dihydrodaidzein Reductase Enhances (S)-Equol Production and Enantioselectivity in a Recombinant Escherichia coli Whole-Cell Reaction System.

Authors:  Pyung-Gang Lee; Joonwon Kim; Eun-Jung Kim; EunOk Jung; Bishnu Prasad Pandey; Byung-Gee Kim
Journal:  Appl Environ Microbiol       Date:  2016-01-22       Impact factor: 4.792

5.  Complete Genome Sequence of the Equol-Producing Bacterium Adlercreutzia equolifaciens DSM 19450T.

Authors:  Hidehiro Toh; Kenshiro Oshima; Takehito Suzuki; Masahira Hattori; Hidetoshi Morita
Journal:  Genome Announc       Date:  2013-09-19

Review 6.  The role of colonic bacteria in the metabolism of the natural isoflavone daidzin to equol.

Authors:  Fatemeh Rafii
Journal:  Metabolites       Date:  2015-01-14

7.  Development and Use of a Real-Time Quantitative PCR Method for Detecting and Quantifying Equol-Producing Bacteria in Human Faecal Samples and Slurry Cultures.

Authors:  Lucía Vázquez; Lucía Guadamuro; Froilán Giganto; Baltasar Mayo; Ana B Flórez
Journal:  Front Microbiol       Date:  2017-06-30       Impact factor: 5.640

8.  Heterologous expression of equol biosynthesis genes from Adlercreutzia equolifaciens.

Authors:  Lucía Vázquez; Ana Belén Flórez; Javier Rodríguez; Baltasar Mayo
Journal:  FEMS Microbiol Lett       Date:  2021-07-07       Impact factor: 2.742

9.  Isoflavone metabolism and bone-sparing effects of daidzein-metabolites.

Authors:  Mariko Uehara
Journal:  J Clin Biochem Nutr       Date:  2013-05-01       Impact factor: 3.114

10.  The production of S-equol from daidzein is associated with a cluster of three genes in Eggerthella sp. YY7918.

Authors:  Yuika Kawada; Shinichiro Yokoyama; Emiko Yanase; Toshio Niwa; Tohru Suzuki
Journal:  Biosci Microbiota Food Health       Date:  2016-03-31
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