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

Applied and Environmental Microbiology

Volumn 78, Issue 14, 2012, Pages 4902-4907

  Shimada, Yoshikazu ^a   Takahashi, Masayuki ^a   Miyazawa, Norihiro ^a   Abiru, Yasuhiro ^a   Uchiyama, Shigeto ^a   Hishigaki, Haretsugu ^a  

^a OTSUKA PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DAIDZEIN; DIHYDRODAIDZEIN; GUT MICROFLORA; IN-VITRO; ISOFLAVONES; LACTIC ACID BACTERIA; LACTOCOCCUS; METABOLIC PATHWAYS; RACEMASE; RECOMBINANT ENZYMES;

AMINO ACIDS; BIOSYNTHESIS; LACTIC ACID;

BIOCHEMISTRY;

BACTERIAL PROTEIN; DAIDZEIN; DIHYDRODAIDZEIN; EQUOL; ISOFLAVONE DERIVATIVE; ISOMERASE; RECOMBINANT PROTEIN;

BACTERIUM; DIGESTIVE SYSTEM; ENZYME ACTIVITY; IDENTIFICATION METHOD; METABOLISM; METABOLITE; NUMERICAL MODEL; ORGANIC COMPOUND; RECOMBINATION;

ARTICLE; BIOSYNTHESIS; DNA SEQUENCE; ENZYMOLOGY; GENETICS; LACTOCOCCUS; METABOLISM; MOLECULAR GENETICS; NUCLEOTIDE SEQUENCE; STEREOISOMERISM;

BACTERIAL PROTEINS; EQUOL; ISOFLAVONES; LACTOCOCCUS; METABOLIC NETWORKS AND PATHWAYS; MOLECULAR SEQUENCE DATA; RACEMASES AND EPIMERASES; RECOMBINANT PROTEINS; SEQUENCE ANALYSIS, DNA; STEREOISOMERISM;

BACTERIA (MICROORGANISMS); LACTOCOCCUS; LACTOCOCCUS SP.;

EID: 84863746870     PISSN: 00992240     EISSN: 10985336     Source Type: Journal    
DOI: 10.1128/AEM.00410-12     Document Type: Article

References (18)

1. Altschul SF, Gish W, Miller W, Myers EW, Lipman DJ. 1990. Basic local alignment search tool. J. Mol. Biol. 215:403-410.
2. Arai Y, et al. 2000. Comparison of isoflavones among dietary intake, plasma concentration and urinary excretion for estimation of phytoestrogen intake. J. Epidemiol. 10:127-135.
3. Bobik TA, Rasche ME. 2004. Purification and partial characterization of the Pyrococcus horikoshii methylmalonyl-CoA epimerase. Appl. Microbiol. Biotechnol. 63:682-685.
4. Bowey E, Adlercreutz H, Rowland I. 2003. Metabolism of isoflavones and lignans by the gut microflora: a study in germ-free and human flora associated rats. Food Chem. Toxicol. 41:631-636.
5. Chenna R, et al. 2003. Multiple sequence alignment with the Clustal series of programs. Nucleic Acids Res. 31:3497-3500.
6. Fortina MG, et al. 2003. Genetic characterization of some lactic acid bacteria occurring in an artisanal protected denomination origin (PDO) Italian cheese, Toma piemontese. Food Microbiol. 20:397-404.
7. Kim M, et al. 2009. Stereospecific biotransformation of dihydrodaidzein into (3S)-equol by the human intestinal bacterium Eggerthella strain Julong 732. Appl. Environ. Microbiol. 75:3062-3068.
8. Kim M, Marsh EN, Kim SU, Han J. 2010. Conversion of (3S,4R)-tetrahydrodaidzein to (3S)-equol by THD reductase: proposed mechanism involving a radical intermediate. Biochemistry 49:5582-5587.
9. Kostelac D, Rechkemmer G, Briviba K. 2003. Phytoestrogens modulate binding response of estrogen receptors alpha and beta to the estrogen response element. J. Agric. Food Chem. 51:7632-7635.
10. Morito K, et al. 2001. Interaction of phytoestrogens with estrogen receptors alpha and beta. Biol. Pharm. Bull. 24:351-356.
11. Ochman H, Gerber AS, Hartl DL. 1988. Genetic applications of an inverse polymerase chain reaction. Genetics 120:621-623.
12. Park HY, Kim M, Han J. 2011. Stereospecific microbial production of isoflavones from isoflavones and isoflavone glucosides. Appl. Microbiol. Biotechnol. 91:1173-1181.
13. Setchell KD, Brown NM, Olsen EL. 2002. The clinical importance of the metabolite equol-a clue to the effectiveness of soy and its isoflavone. J. Nutr. 132:3577-3584.
14. Shimada Y, et al. 2011. Identification of two novel reductases involved in equol biosynthesis for Lactococcus strain 20-92. J. Mol. Microbiol. Biotechnol. 21:160-172.
15. Shimada Y, et al. 2010. Cloning and expression of a novel NADP(H)-dependent daidzein reductase, an enzyme involved in the metabolism of daidzein, from equol-producing Lactococcus garvieae 20-92. Appl. Environ. Microbiol. 76:5892-5901.
16. Uchiyama S, Ueno T, Suzuki T. 2007. Identification of a newly isolated equol-producing lactic acid bacterium from the human feces. J. Intestinal Microbiol. 21:217-220.
17. Wang XL, Hur HG, Lee JH, Kim KT, Kim SI. 2005. Enantioselective synthesis of S-equol from dihydrodaidzein by a newly isolation anaerobic human intestinal bacterium. Appl. Environ. Microbiol. 71:214-219.
18. Wang XL, Shin KH, Hur HG, Kim SI. 2005. Enhanced biosynthesis of dihydrodaidzein and dihydrogenistein by a newly isolated bovine rumen anaerobic bacterium. J. Biotechnol. 115:261-269.