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Stereospecific microbial production of isoflavanones from isoflavones and isoflavone glucosides.
Appl Microbiol Biotechnol. 2011 Aug; 91(4):1173-81.AM

Abstract

A Gram-negative anaerobic microorganism, MRG-1, isolated from human intestine showed high activities of deglycosylation and reduction of daidzin, based on rapid TLC analysis. A rod-shaped strain MRG-1 was identified as a new species showing 91.0% homology to Coprobacillus species, based on 16S rRNA sequence analysis. The strain MRG-1 showed β-glucosidase activity toward daidzin and genistin, and daidzein and genistein were produced, respectively. However, the strain MRG-1 did not react with flavone glycosides, flavanone glycosides, and isoflavone C-glucoside. Besides, MRG-1 showed stereoselective reductase activity to isoflavone, daidzein, genistein, 7-hydroxyisoflavone, and formononetin, resulting in the formation of corresponding R-isoflavanone enantiomers. The new isoflavanones of 7-hydroxyisoflavanone and dihydroformononetin were characterized by NMR, and the absolute configurations of the enantiomers were determined with CD spectroscopy. The kinetic study of the anaerobic biotransformation showed both activities were exceptionally fast compared to the reported conversion by other anaerobic bacteria.

Authors+Show Affiliations

Metalloenzyme Research Group and Department of Biotechnology, Chung-Ang University, Anseong 456-756, South Korea.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21562980

Citation

Park, Hye-Yeon, et al. "Stereospecific Microbial Production of Isoflavanones From Isoflavones and Isoflavone Glucosides." Applied Microbiology and Biotechnology, vol. 91, no. 4, 2011, pp. 1173-81.
Park HY, Kim M, Han J. Stereospecific microbial production of isoflavanones from isoflavones and isoflavone glucosides. Appl Microbiol Biotechnol. 2011;91(4):1173-81.
Park, H. Y., Kim, M., & Han, J. (2011). Stereospecific microbial production of isoflavanones from isoflavones and isoflavone glucosides. Applied Microbiology and Biotechnology, 91(4), 1173-81. https://doi.org/10.1007/s00253-011-3310-7
Park HY, Kim M, Han J. Stereospecific Microbial Production of Isoflavanones From Isoflavones and Isoflavone Glucosides. Appl Microbiol Biotechnol. 2011;91(4):1173-81. PubMed PMID: 21562980.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereospecific microbial production of isoflavanones from isoflavones and isoflavone glucosides. AU - Park,Hye-Yeon, AU - Kim,Mihyang, AU - Han,Jaehong, Y1 - 2011/05/12/ PY - 2011/03/17/received PY - 2011/04/05/accepted PY - 2011/04/01/revised PY - 2011/5/13/entrez PY - 2011/5/13/pubmed PY - 2011/11/16/medline SP - 1173 EP - 81 JF - Applied microbiology and biotechnology JO - Appl. Microbiol. Biotechnol. VL - 91 IS - 4 N2 - A Gram-negative anaerobic microorganism, MRG-1, isolated from human intestine showed high activities of deglycosylation and reduction of daidzin, based on rapid TLC analysis. A rod-shaped strain MRG-1 was identified as a new species showing 91.0% homology to Coprobacillus species, based on 16S rRNA sequence analysis. The strain MRG-1 showed β-glucosidase activity toward daidzin and genistin, and daidzein and genistein were produced, respectively. However, the strain MRG-1 did not react with flavone glycosides, flavanone glycosides, and isoflavone C-glucoside. Besides, MRG-1 showed stereoselective reductase activity to isoflavone, daidzein, genistein, 7-hydroxyisoflavone, and formononetin, resulting in the formation of corresponding R-isoflavanone enantiomers. The new isoflavanones of 7-hydroxyisoflavanone and dihydroformononetin were characterized by NMR, and the absolute configurations of the enantiomers were determined with CD spectroscopy. The kinetic study of the anaerobic biotransformation showed both activities were exceptionally fast compared to the reported conversion by other anaerobic bacteria. SN - 1432-0614 UR - https://www.unboundmedicine.com/medline/citation/21562980/Stereospecific_microbial_production_of_isoflavanones_from_isoflavones_and_isoflavone_glucosides_ L2 - https://dx.doi.org/10.1007/s00253-011-3310-7 DB - PRIME DP - Unbound Medicine ER -