Metabolites of Daidzein and Genistein and Their Biological Activities

Chang, Yu-Tang; Nair, Muraleedharan G.; Nitiss, John L.

doi:10.1021/np50126a016

Cited by 85 publications

(59 citation statements)

References 16 publications

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“…strain Niu-O16 (52), the C-ring cleavage yielding 6Ј-hydroxy-O-desmethylangolensin and subsequently 2-(4-hydroxyphenyl)propionic acid is catalyzed by Eubacterium ramulus (39,51). Although proposed to be a metabolite of microbial genistein conversion (2,11), so far, 5-hydroxy-equol has been detected neither in vitro nor in vivo as a product of the human or rat intestinal microbiota. This suggests that strain Mt1B8 is not common in humans and rats but is specific to mice.…”

Section: Resultsmentioning

confidence: 99%

Conversion of Daidzein and Genistein by an Anaerobic Bacterium Newly Isolated from the Mouse Intestine

Matthies¹,

Clavel

Gütschow

et al. 2008

Appl Environ Microbiol

120

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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-hydroxyequol 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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Section: Resultsmentioning

confidence: 99%

Conversion of Daidzein and Genistein by an Anaerobic Bacterium Newly Isolated from the Mouse Intestine

Matthies¹,

Clavel

Gütschow

et al. 2008

Appl Environ Microbiol

120

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show abstract

“…This hypothesis may be sup-ported by some previous findings. Namely, genistein was found to act as an inhibitor of DNA topoisomerases type I (Chang et al 1995) and type II (Azuma et al 1995;Chang et al 1995;Constantinou et al 1995;Yamagishi et al 2001;Snyder & Gillies 2002;Verdrengh et al 2004). It was revealed that daidzein possesses the inhibitory activity against topoisomerase I and weakly inhibits topoisomerase II (Chang et al 1995;Sun et al 1998;Yamagishi et al 2001), while kaempferol undoubtedly inhibits topoisomerase II (Constantinou et al 1995).…”

Section: Discussionmentioning

confidence: 99%

Assessment of antibacterial effects of flavonoids by estimation of generation times in liquid bacterial cultures

et al. 2007

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Antibacterial activities of various flavonoids, a group of natural plant substances, have been reported previously, however, there are contradictory data, published by various authors, regarding sensitivity of particular bacterial species to these compounds. These problems arose apparently because of using different methods by various researchers. Here we tested sensitivity of several bacterial species (Gram-positive: Bacillus subtilis, Micrococcus luteus, Sarcina sp. and Staphylococcus aureus; and Gram-negative: Citrobacter freundii, Escherichia coli, Klebsiella pneumoniae, Proteus vulgaris, Pseudomonas aeruginosa, Salmonella enterica, Serratia marcescens and Vibrio harveyi) to various flavonoids: genistein and daidzein (isoflavones), apigenin (a flavone), naringenin (a flavanone) and kaempferol (a flavonol) by measurement of generation times of bacteria in liquid cultures. The presented results indicate that this simple method is adequate for unambiguous assessment of sensitivity of bacterial strains to flavonoids.

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“…Many ASR-regulated CYPs also are classified with electron transport functions (GO:0006118) and, thus, their involvement in the phenylpropanoid pathway also may cause the overrepresentation of electron transport functions. The phenylpropanoid pathway is involved in the biosynthesis of phytoalexins and antimicrobial compounds, including diadzein, genistein, glyceollin, tannins, and cell-wall-reinforcing compounds such as lignans and lignins (Abbasi et al 2001;Chang et al 1995;Chiang and Norris 1983;Hahlbrock and Scheel 1989). In both resistant and susceptible plants, mRNAs encoding these enzymes were induced during the early, general defense response against ASR infection, but most genes returned to mock levels by 24 hai.…”

Section: Potential Biological Roles Of Asr-regulated Genesmentioning

confidence: 99%

Distinct Biphasic mRNA Changes in Response to Asian Soybean Rust Infection

Mortel¹,

Recknor²,

Graham³

et al. 2007

MPMI

117

125

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Asian soybean rust (ASR), caused by Phakopsora pachyrhizi, is now established in all major soybean-producing countries. Currently, there is little information about the molecular basis of ASR–soybean interactions, which will be needed to assist future efforts to develop effective resistance. Toward this end, abundance changes of soybean mRNAs were measured over a 7-day ASR infection time course in mock-inoculated and infected leaves of a soybean accession (PI230970) carrying the Rpp2 resistance gene and a susceptible genotype (Embrapa-48). The expression profiles of differentially expressed genes (ASR-infected compared with the mock-inoculated control) revealed a biphasic response to ASR in each genotype. Within the first 12 h after inoculation (hai), which corresponds to fungal germination and penetration of the epidermal cells, differential gene expression changes were evident in both genotypes. mRNA expression of these genes mostly returned to levels found in mock-inoculated plants by 24 hai. In the susceptible genotype, gene expression remained unaffected by rust infection until 96 hai, a time period when rapid fungal growth began. In contrast, gene expression in the resistant genotype diverged from the mock-inoculated control earlier, at 72 h, demonstrating that Rpp2-mediated defenses were initiated prior to this time. These data suggest that ASR initially induces a non-specific response that is transient or is suppressed when early steps in colonization are completed in both soybean genotypes. The race-specific resistance phenotype of Rpp2 is manifested in massive gene expression changes after the initial response prior to the onset of rapid fungal growth that occurs in the susceptible genotype.

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Metabolites of Daidzein and Genistein and Their Biological Activities

Cited by 85 publications

References 16 publications

Conversion of Daidzein and Genistein by an Anaerobic Bacterium Newly Isolated from the Mouse Intestine

Conversion of Daidzein and Genistein by an Anaerobic Bacterium Newly Isolated from the Mouse Intestine

Assessment of antibacterial effects of flavonoids by estimation of generation times in liquid bacterial cultures

Distinct Biphasic mRNA Changes in Response to Asian Soybean Rust Infection

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