Dataset Information

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

ABSTRACT: A newly isolated rod-shaped, gram-negative anaerobic bacterium from human feces, named Julong 732, was found to be capable of metabolizing the isoflavone dihydrodaidzein to S-equol under anaerobic conditions. The metabolite, equol, was identified by using electron impact ionization mass spectrometry, (1)H and (13)C nuclear magnetic resonance spectroscopy, and UV spectral analyses. However, strain Julong 732 was not able to produce equol from daidzein, and tetrahydrodaidzein and dehydroequol, which are most likely intermediates in the anaerobic metabolism of dihydrodaidzein, were not detected in bacterial culture medium containing dihydrodaidzein. Chiral stationary-phase high-performance liquid chromatography eluted only one metabolite, S-equol, which was produced from a bacterial culture containing a racemic mixture of dihydrodaidzein. Strain Julong 732 did not show racemase activity to transform R-equol to S-equol and vice versa. Its full 16S rRNA gene sequence (1,429 bp) had 92.8% similarity to that of Eggerthella hongkongenis HKU10. This is the first report of a single bacterium capable of converting a racemic mixture of dihydrodaidzein to enantiomeric pure S-equol.

SUBMITTER: Wang XL

PROVIDER: S-EPMC544246 | biostudies-literature | 2005 Jan

REPOSITORIES: biostudies-literature

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

Wang Xiu-Ling XL Hur Hor-Gil HG Lee Je Hyeon JH Kim Ki Tae KT Kim Su-Il SI

Applied and environmental microbiology 20050101 1

A newly isolated rod-shaped, gram-negative anaerobic bacterium from human feces, named Julong 732, was found to be capable of metabolizing the isoflavone dihydrodaidzein to S-equol under anaerobic conditions. The metabolite, equol, was identified by using electron impact ionization mass spectrometry, (1)H and (13)C nuclear magnetic resonance spectroscopy, and UV spectral analyses. However, strain Julong 732 was not able to produce equol from daidzein, and tetrahydrodaidzein and dehydroequol, whi ...[more]

PMID: 15640190

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Project description:Due to toxicity and persistence of paraquat (a widely used herbicide), eco-friendly remediation approaches to its contamination and effective antidotes to its poisoning have been highly desired and raised increasing concerns. Paraquat degradation was lesser in aerobic soil in comparison with anaerobic soil, and humic-reducing microorganisms (HRMs) play a key role in paraquat anaerobic transformation process. However, the degradation pathways and related mechanisms remain poorly understood. In this study, we investigated the specific interaction mechanisms of the paraquat transformation processes mediated by a humic-reducing strain under anaerobic conditions. A strain of pure culture, designated as PQ01, was successfully isolated from paddy soil using anaerobic enrichment procedure, and identified as Pseudomonas geniculata using phenotypic and phylogenetic analysis. Sucrose, glucose, pyruvate, formic acid, and acetic acid were shown to be favorable electron donors for the reduction of anthrahydroquinone-2,6-disulfonate (AQDS) reduction by PQ01. The strain also had the ability of reducing Fe(III) (hydr)oxides in the presence of sucrose with efficiencies in the order of ferrihydrite > α-FeOOH/γ-FeOOH > γ-Fe2O3 > α-Fe2O3. In the "PQ01 + paraquat + AQDS + sucrose" system, AQDS reduction and paraquat biotransformation by strain PQ01 occurred simultaneously, and the presence of sucrose significantly enhanced the biotransformation. Specific mechanisms of the electron transfer processes are promoted by both PQ01 and AQDS, and proceed in two aspects: (1) paraquat served as electron donor in the anaerobic reduction of AQDS by strain PQ01; (2) AQDS was reduced by PQ01 anaerobic metabolism to produce AH2QDS, which can directly react with paraquat under anaerobic conditions to generate a single crystal compound (molecular formula of the unit structure is C2 6H2 0N2O8S2), causing the paraquat to decline dramatically. In conclusion, this main mechanism included the microbial reduction of AQDS to AH2QDS, followed by the abiotic reaction between AH2QDS and paraquat. This study reported the new characteristics of P. geniculata capable of reducing humics analogs, Fe(III) (hydr)oxides, and paraquat, and proposed a novel electron transformation mechanism of the HRMs' mediated degradation of organic contaminants.

Dataset Information

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

Publications

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

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