Enantioselective Dehydroxylation of Enterodiol and Enterolactone Precursors by Human Intestinal Bacteria

Jin, Jong-Sik; Zhao, Yu-Feng; Nakamura, Norio; Akao, Teruaki; Kakiuchi, Nobuko; Min, Byung‐Sun; Hattori, Masao

doi:10.1248/bpb.30.2113

Cited by 61 publications

(45 citation statements)

References 31 publications

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“…As shown in Table 5, the reported association between lignan polyphenols and equol suggests that they are metabolized by the same pathway [25]. It has been suggested that some of the bacterium strains, for example, Eggerthella sp, were associated with both the metabolism of daidzein to equol and that of lignan polyphenols to enterodiol and enterolactone [26,27]. However, the specific intestinal bacteria and pathway responsible for metabolism of these two groups of phytoestrogens need to be identified in the future.…”

Section: Discussionmentioning

confidence: 99%

Levels of urinary isoflavones and lignan polyphenols in Japanese women

Liu

Tanabe

Harada

2013

Environ Health Prev Med

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Objectives High consumption of soybean products has been associated with a reduced risk of hormone-sensitive tumors. Soybean products contain phytoestrogens, such as daidzein, and sesame seeds contain secoisolariciresinol. These compounds are further metabolized to equol, enterodiol, and enterolactone by intestinal bacteria. However, individual differences in the metabolizing potential remain unclear. The aim of this study was to evaluate the urinary daidzein, equol, enterodiol, and enterolactone concentrations in women from several different regions of Japan according to age group. Methods Five hundred urine samples collected from Japanese women living in Sapporo, Sendai, Kyoto, Kochi, and Naha were analyzed for daidzein, equol, enterodiol, and enterolactone concentration by gas chromatographymass spectrometry. Results The urinary isoflavone and lignan polyphenol levels did not differ significantly among the sampling sites, except for daidzein, which was highest in urine collected at Naha. The prevalence of equol producers was 39 % in the total study cohort. In equol producers, a positive correlation was observed between the urinary daidzein and equol levels (r = 0.399, p \ 0.001). However, there was no significant difference between daidzein concentrations in equol producers and non-producers. Moreover, the levels of enterodiol and enterolactone were higher in equol producers than in equol non-producers. In the multivariate logistic analyses, two factors, Sendai dwelling and current smoking, were found to be significant [equol producers to non-producers: odds ratio 2.15 (95 % confidence interval: 1.17-4.02) and odds ratio 0.32 (0.15-0.63), respectively]. Conclusions Our data suggest that geographic factors and smoking status should be considered during the evaluation of equol in urine samples and that the same pathway may be responsible for the metabolism of both isoflavones and lignan polyphenols.

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Section: Discussionmentioning

confidence: 99%

Levels of urinary isoflavones and lignan polyphenols in Japanese women

Liu

Tanabe

Harada

2013

Environ Health Prev Med

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“…The latter bacterium could transform (+)-dihydroxyenterodiol (DHEND) to (+)-END, but not (−)-DHEND to (−)-END (Jin, Zhao, Nakamura, Akao, Kakiuchi, Min, et al, 2007). The aforementioned authors isolated a different bacterium, strain ARC-1, capable of dehydroxylating (−)-DHEND to (−)-END from human faeces.…”

Section: Microbiota Responsible For the Conversion Of Plant Lignans Tmentioning

confidence: 99%

Plant and mammalian lignans: A review of source, intake, metabolism, intestinal bacteria and health

Landete

2012

Food Research International

214

167

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“…SDG-2 and strain ARC-1 enantioselectively dehydroxylate dihydroxyenterolactone (DHENL) and dihydroxyenterodiol (DHEND). 23) Eg. sp.…”

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Human Intestinal Bacterium, Strain END-2 Is Responsible for Demethylation as Well as Lactonization during Plant Lignan Metabolism

Hattori

2010

Biological & Pharmaceutical Bulletin

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Plant lignans and isoflavones that have estrogen-like properties, are classified as phytoestrogens based on their activities and chemical structures.1,2) Experimental and epidemiological studies have shown that phytoestrogens have potential health benefits in treating hormone-dependent diseases such as breast and prostate cancers. 3-7)Because ingested plant lignans undergo metabolic degradation, their transformation and metabolites have been extensively studied. [8][9][10][11][12][13] The mammalian lignans, enterolactone (ENL) and enterodiol (END), are of considerable interest since their isolation from the urine of humans and other animals in 1980.14) Subsequent studies have verified that the origins of mammalian lignans are plant lignans and that intestinal bacteria play a critical role in the formation of ENL and END. [15][16][17][18] Intestinal bacteria metabolize plant lignans by processes such as deglucosylation, demethylenation, ring cleavage, demethylation, dehydroxylation and oxidation. Several human intestinal bacteria that function in these processes have been isolated and characterized. 10,11,[19][20][21][22] However, ENL and END have two enantiomeric, mirror image forms. The ENL that is transformed via the anaerobic incubation of pinoresinol diglucoside (PDG) from Eucommia ulmoides OLIV. with intestinal bacteria, assumes the (Ϫ)-form.10) On the other hand, the ENL that is obtained via incubation with secoisolariciresinol diglucoside (SDG) from flaxseed, assumes the (ϩ)-form.13) We investigated which bacteria are involved in the transformation of the respective enantiomeric forms.The human intestinal bacteria, Eggerthella (Eg.) sp. SDG-2 and strain ARC-1 enantioselectively dehydroxylate dihydroxyenterolactone (DHENL) and dihydroxyenterodiol (DHEND). Moreover, the bacterial strains, strain END-2 and Ruminococcus (R.) sp. END-1, which oxidize END to ENL were isolated from human feces.24) When strain END-2 was incubated with a mixture of (ϩ)-END and (Ϫ)-END, only (ϩ)-END was oxidized to (ϩ)-ENL, and (Ϫ)-END remained unchanged (Fig. 1). Conversely, R. sp. END-1 converted only (Ϫ)-END to (Ϫ)-ENL.Here, we further describe the substrate specificity and cooperative behavior of strain END-2 with strain ARC-1 during the metabolism of plant lignans. MATERIALS AND METHODSGeneral Fecal suspensions and intestinal bacteria were incubated in an anaerobic model EAN-140 incubator (Tabai Co., Osaka, Japan). Optical rotations were measured in MeOH using a DIP-360 automatic polarimeter (Jasco Co., Tokyo, Japan). H-1 H-correlated spectroscopy, heteronuclear multiple-quantum coherence, heteronuclear multiple-bond coherence and nuclear Overhauser effect spectroscopy experiments were performed using a Varian Unity 500 ( 1 H: 500 MHz, 13 C: 125 MHz) and a Varian Gemini 300 ( 1 H: 300 MHz, 13 C: 75 MHz). Samples were separated by TLC on plates precoated with silica gel 60-F 254 (0.25 mm, Merck Co., Darmstadt, Germany), and spots were detected under UV excitation or by exposure to I 2 vapor. Samples were also separated by chrom...

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Enantioselective Dehydroxylation of Enterodiol and Enterolactone Precursors by Human Intestinal Bacteria

Cited by 61 publications

References 31 publications

Levels of urinary isoflavones and lignan polyphenols in Japanese women

Levels of urinary isoflavones and lignan polyphenols in Japanese women

Plant and mammalian lignans: A review of source, intake, metabolism, intestinal bacteria and health

Human Intestinal Bacterium, Strain END-2 Is Responsible for Demethylation as Well as Lactonization during Plant Lignan Metabolism

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