Conversion of daidzein and genistein by an anaerobic bacterium newly isolated from the mouse intestine
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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-hydroxy-equol 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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Elevated levels of genistein and daidzein suggest reduced dietary nutrient metabolizing bacteria in the oASD microbiota.
“Elevated levels of these metabolites suggest reduced dietary nutrient metabolizing bacteria in the oASD microbiota (Matthies et al., 2008, 2009).”
From Human Gut Microbiota from Autism Spectrum Disorder Promote Behavioral Symptoms in Mice (2019) · cites this paper as Matthies et al., 2008
Cites
Dietary polyphenols and the prevention of diseases
Scalbert, A., Manach, C., Morand, C., Rémésy, C., & Jiménez, L. (2005) · Critical Reviews in Food Science and Nutrition · doi:10.1080/1040869059096 · Cited by 2,999 · see citing works
Impaired On/Off Regulation of TNF Biosynthesis in Mice Lacking TNF AU-Rich Elements
Kontoyiannis, D. L., Pasparakis, M., Pizarro, T. T., Cominelli, F., & Kollias, G. A. (1999) · Immunity · doi:10.1016/s1074-7613(00)80038-2 · Cited by 1,329 · see citing works
Dietary agents in cancer prevention: flavonoids and isoflavonoids
Birt, D. F., Hendrich, S., & Wang, W. (2001) · Pharmacology & Therapeutics · doi:10.1016/s0163-7258(01)00137-1 · Cited by 1,172 · see citing works
Dietary Isoflavones: Biological Effects and Relevance to Human Health
Setchell, K. D. R., & Cassidy, A. (1999) · Journal of Nutrition · doi:10.1093/jn/129.3.758s · Cited by 1,158 · see citing works
Phytoestrogens: the biochemistry, physiology, and implications for human health of soy isoflavones
Setchell, K. D. R. (1998) · American Journal of Clinical Nutrition · doi:10.1093/ajcn/68.6.1333s · Cited by 1,137 · see citing works
Rapid method for distinction of gram-negative from gram-positive bacteria
Gregersen, T. (1978) · Applied Microbiology and Biotechnology · doi:10.1007/bf00498806 · Cited by 948 · see citing works
Interaction of Phytoestrogens with Estrogen Receptors .ALPHA. and .BETA..
Morito, K., HIROSE, T., Kinjo, J., Hirakawa, T., Okawa, M., Nohara, T., Ogawa, S., Inoue, S., Muramatsu, M., & Masamune, Y. (2001) · Biological and Pharmaceutical Bulletin · doi:10.1248/bpb.24.351 · Cited by 615 · see citing works
Rowland, I. R., Wiseman, H., Sanders, T. A. B., Adlercreutz, H., & Bowey, E. A. (2000) · Nutrition and Cancer · doi:10.1207/s15327914nc3601_5 · Cited by 583 · see citing works
Gut Bacterial Metabolism of the Soy Isoflavone Daidzein: Exploring the Relevance to Human Health
Atkinson, C., Frankenfeld, C. L., & Lampe, J. W. (2005) · Experimental Biology and Medicine · doi:10.1177/153537020523000302 · Cited by 516 · see citing works
Setchell, K. D., Clerici, C., Lephart, E. D., Cole, S. J., Heenan, C., Castellani, D., Wolfe, B. E., Nechemias-Zimmer, L., Brown, N. M., Lund, T. D., et al. (2005) · The American Journal of Clinical Nutrition · doi:10.1093/ajcn/81.5.1072 · Cited by 471 · see citing works
Interaction of Phytoestrogens with Estrogen Receptors .ALPHA. and .BETA.(II).
Morito, K., Aomori, T., Hirose, T., Kinjo, J., Hasegawa, J., Ogawa, S., Inoue, S., Muramatsu, M., & Masamune, Y. (2002) · Biological and Pharmaceutical Bulletin · doi:10.1248/bpb.25.48 · Cited by 464 · see citing works
Equol, a natural estrogenic metabolite from soy isoflavones
Muthyala, R. S., Ju, Y. H., Sheng, S., Williams, L. D., Doerge, D. R., Katzenellenbogen, B. S., Helferich, W. G., & Katzenellenbogen, J. A. (2004) · Bioorganic & Medicinal Chemistry · doi:10.1016/j.bmc.2003.11.035 · Cited by 441 · see citing works
Antioxidant Activities of Isoflavones and Their Biological Metabolites in a Liposomal System
Arora, A., Nair, M. G., & Strasburg, G. M. (1998) · Archives of Biochemistry and Biophysics · doi:10.1006/abbi.1998.0783 · Cited by 404 · see citing works
Soybean isoflavones: effect of environment and variety on composition
Eldridge, A. C., & Kwolek, W. F. (1983) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf00116a052 · Cited by 393 · see citing works
Gut-associated bacterial microbiota in paediatric patients with inflammatory bowel disease
Conte, M. P., Schippa, S., Zamboni, I., Penta, M., Chiarini, F., Seganti, L., Osborn, J., Falconieri, P., Borrelli, O., & Cucchiara, S. (2006) · Gut · doi:10.1136/gut.2005.078824 · Cited by 383 · see citing works
Phytoestrogens: Recent Developments
Cos, P., Bruyne, T. D., Apers, S., Berghe, D. V., Pieters, L. A. C., & Vlietinck, A. J. (2003) · Planta Medica · doi:10.1055/s-2003-41122 · Cited by 339 · see citing works
Maruo, T., Sakamoto, M., Ito, C., Toda, T., & Benno, Y. (2008) · INTERNATIONAL JOURNAL OF SYSTEMATIC AND EVOLUTIONARY MICROBIOLOGY · doi:10.1099/ijs.0.65404-0 · Cited by 308 · see citing works
Hwang, C. S., Kwak, H.-S., Lim, H. J., Lee, S. H., Kang, Y. S., Choe, T. B., Hur, H. G., & Han, K. O. (2006) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/j.jsbmb.2006.06.020 · Cited by 296 · see citing works
Joannou, G. E., KELLY, G. E., Reeder, A. Y., Waring, M. A., & Nelson, C. (1995) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/0960-0760(95)00131-i · Cited by 282 · see citing works
Hur, H.-G., Lay, J. O., Beger, R. D., Freeman, J. P., & Rafii, F. (2000) · Archives of Microbiology · doi:10.1007/s002030000222 · Cited by 271 · see citing works
Decroos, K., Vanhemmens, S., Cattoir, S., Boon, N., & Verstraete, W. (2004) · Archives of Microbiology · doi:10.1007/s00203-004-0747-4 · Cited by 234 · see citing works
Degradation of Quercetin and Luteolin by Eubacterium ramulus
Braune, A., Gütschow, M., Engst, W., & Blaut, M. (2001) · Applied and Environmental Microbiology · doi:10.1128/aem.67.12.5558-5567.2001 · Cited by 226 · see citing works
Self-citationPharmaceutical Prospects of Phytoestrogens
Usui, T. (2006) · Endocrine Journal · doi:10.1507/endocrj.53.7 · Cited by 210 · see citing works
Clavel, T., Henderson, G., Alpert, C.-A., Philippe, C., Rigottier‐Gois, L., Dore, J. M., & Blaut, M. (2005) · Applied and Environmental Microbiology · doi:10.1128/aem.71.10.6077-6085.2005 · Cited by 208 · see citing works
Self-citationWang, X.-L., Hur, H.-G., Lee, J. H., Kim, K. T., & Kim, S.-I. (2005) · Applied and Environmental Microbiology · doi:10.1128/aem.71.1.214-219.2005 · Cited by 196 · see citing works
Metabolism of Daidzein and Genistein by Intestinal Bacteria
Chang, Y.-C., & Nair, M. G. (1995) · Journal of Natural Products · doi:10.1021/np50126a014 · Cited by 178 · see citing works
Anaerobic C-ring cleavage of genistein and daidzein by Eubacterium ramulus
Schoefer, L., Mohan, R., Braune, A., Birringer, M., & Blaut, M. (2002) · FEMS Microbiology Letters · doi:10.1111/j.1574-6968.2002.tb11081.x · Cited by 154 · see citing works
Self-citationIsoflavones and Functional Foods Alter the Dominant Intestinal Microbiota in Postmenopausal Women
Clavel, T., Fallani, M., Lepage, P., Levenez, F., Mathey, J., Rochet, V., SEREZAT, M., Sutren, M., Henderson, G., Bennetau‐Pelissero, C., et al. (2005) · Journal of Nutrition · doi:10.1093/jn/135.12.2786 · Cited by 151 · see citing works
Self-citationBolca, S., Possemiers, S., Herregat, A., Huybrechts, I., Heyerick, A., Vriese, S. D., Verbruggen, M. A., Depypere, H. T., Keukeleire, D. D., Bracke, M., et al. (2007) · Journal of Nutrition · doi:10.1093/jn/137.10.2242 · Cited by 146 · see citing works
Clavel, T., Lippman, R., Gavini, F., Dore, J. M., & Blaut, M. (2006) · Systematic and Applied Microbiology · doi:10.1016/j.syapm.2006.02.003 · Cited by 145 · see citing works
Self-citationGenistein—A dietary compound inducing hormonal and metabolic changes
Szkudelska, K., & Nogowski, L. (2007) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/j.jsbmb.2007.01.005 · Cited by 133 · see citing works
HPLC-Mass Spectrometry Analysis of Isoflavones
Barnes, S., Coward, L. U., KIRK, M. C., & Sfakianos, J. (1998) · Experimental Biology and Medicine · doi:10.3181/00379727-217-44230 · Cited by 131 · see citing works
Possemiers, S., Bolca, S., Eeckhaut, E., Depypere, H. T., & Verstraete, W. (2007) · FEMS Microbiology Ecology · doi:10.1111/j.1574-6941.2007.00330.x · Cited by 116 · see citing works
Production of equol from daidzein by gram-positive rod-shaped bacterium isolated from rat intestine
Minamida, K., Tanaka, M., Abe, A., Sone, T., Tomita, F., Hara, H., & Asano, K. (2006) · Journal of Bioscience and Bioengineering · doi:10.1263/jbb.102.247 · Cited by 114 · see citing works
Identification of lignans and phytoestrogens in urine of chimpanzees
Adlercreutz, H., Musey, P. I., Fotsis, T., Bannwart, C., Wähälä, K., Mäkelä, T., Brunow, G., & Hase, T. (1986) · Clinica Chimica Acta · doi:10.1016/0009-8981(86)90230-5 · Cited by 113 · see citing works
Coldham, N. G., Darby, C., Hows, M. E. P., King, L. J., Zhang, A.-Q., & Sauer, M. J. (2002) · Xenobiotica · doi:10.1080/00498250110085809 · Cited by 112 · see citing works
Blair, R. M., Appt, S. E., Clarkson, T. B., & Franke, A. A. (2003) · Journal of Nutrition · doi:10.1093/jn/133.7.2262 · Cited by 99 · see citing works
Asaccharobacter celatus gen. nov., sp. nov., isolated from rat caecum
Minamida, K., Ota, K., Nishimukai, M., Tanaka, M., Abe, A., Sone, T., Tomita, F., Hara, H., & Asano, K. (2008) · INTERNATIONAL JOURNAL OF SYSTEMATIC AND EVOLUTIONARY MICROBIOLOGY · doi:10.1099/ijs.0.64894-0 · Cited by 89 · see citing works
Coldham, N. G., Howells, L. C., Santi, A., Montesissa, C., Langlais, C., King, L. J., Macpherson, D., & Sauer, M. J. (1999) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/s0960-0760(99)00104-1 · Cited by 88 · see citing works
Isoflavones, Equol and Cardiovascular Disease: Pharmacological and Therapeutic Insights
Jackman, K. A., Woodman, O. L., & Sobey, C. G. (2007) · Current Medicinal Chemistry · doi:10.2174/092986707782360178 · Cited by 87 · see citing works
Metabolites of Daidzein and Genistein and Their Biological Activities
Chang, Y., Nair, M. G., & Nitiss, J. L. (1995) · Journal of Natural Products · doi:10.1021/np50126a016 · Cited by 85 · see citing works
Production of phytoestrogen S-equol from daidzein in mixed culture of two anaerobic bacteria
Wang, X., Kim, H.-J., Kang, S.-I., Kim, S., & Hur, H. (2006) · Archives of Microbiology · doi:10.1007/s00203-006-0183-8 · Cited by 82 · see citing works
Isolation of an isoflavone-metabolizing, Clostridium-like bacterium, strain TM-40, from human faeces
Tamura, M., Tsushida, T., & Shinohara, K. (2006) · Anaerobe · doi:10.1016/j.anaerobe.2006.10.001 · Cited by 77 · see citing works
Wang, X., Shin, K. A., Hur, H., & Kim, S. (2004) · Journal of Biotechnology · doi:10.1016/j.jbiotec.2004.08.014 · Cited by 75 · see citing works
Rafii, F., Davis, C., Park, M., Heinze, T. M., & Beger, R. D. (2003) · Archives of Microbiology · doi:10.1007/s00203-003-0551-6 · Cited by 75 · see citing works
Soy and red clover for mid-life and aging
GELLER, S. E., & Studee, L. (2006) · Climacteric · doi:10.1080/13697130600736934 · Cited by 69 · see citing works
Isolation and identification of equol-producing bacterial strains from cultures of pig faeces
Yu, Z., Yao, W., & Zhu, W. (2008) · FEMS Microbiology Letters · doi:10.1111/j.1574-6968.2008.01108.x · Cited by 66 · see citing works
Leininger, C. (2005) · Cited by 55 · see citing works
Rüfer, C. E., Glatt, H. R., & Kulling, S. E. (2005) · Drug Metabolism and Disposition · doi:10.1124/dmd.105.004929 · Cited by 55 · see citing works
Disposition and Biotransformation of the Estrogenic Isoflavone Daidzein in Rats
Bayer, T. (2001) · Toxicological Sciences · doi:10.1093/toxsci/62.2.205 · Cited by 44 · see citing works
Synthesis of Novel Mammalian Metabolites of the Isoflavonoid Phytoestrogens Daidzein and Genistein
Wähälä, K., Salakka, A., & Adlercreutz, H. (1998) · Experimental Biology and Medicine · doi:10.3181/00379727-217-44235 · Cited by 41 · see citing works
Identification of phytoestrogens in the urine of male dogs
Juniewicz, P. E., Morell, S. P., Moser, A. B., & EWING, L. L. (1988) · Journal of Steroid Biochemistry · doi:10.1016/0022-4731(88)90343-3 · Cited by 37 · see citing works
Hydrogen Transfer Reduction of Isoflavones
Hase, T. A., & W撹獲�, K. (1989) · Heterocycles · doi:10.3987/com-88-s94 · Cited by 28 · see citing works
Wang, X., Kim, K., Lee, J.-H., Hur, H.-G., & Kim, S.-I. (2004) · Journal of Microbiology and Biotechnology · Cited by 28 · see citing works
Serum equol, bone mineral density and biomechanical bone strength differ among four mouse strains
Ward, W. E., Kim, S., Chan, D., & Fonseca, D. (2005) · The Journal of Nutritional Biochemistry · doi:10.1016/j.jnutbio.2005.04.002 · Cited by 26 · see citing works
Tamura, M., & Saitoh, H. (2006) · Journal of the Science of Food and Agriculture · doi:10.1002/jsfa.2549 · Cited by 6 · see citing works
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Panche, A. N., Diwan, A. D., & Chandra, S. (2016) · Journal of Nutritional Science · doi:10.1017/jns.2016.41 · Cited by 5,644 · see citing works
Human Gut Microbiota from Autism Spectrum Disorder Promote Behavioral Symptoms in Mice
Sharon, G., Cruz, N. J., Kang, D.-W., Gandal, M. J., Wang, B., Kim, Y.-M., Zink, E. M., Casey, C. P., Taylor, B. C., Lane, C. J., et al. (2019) · Cell · doi:10.1016/j.cell.2019.05.004 · Cited by 1,182 · see citing works
Equol: History, Chemistry, and Formation
Setchell, K. D. R., & Clerici, C. (2010) · The Journal of Nutrition · doi:10.3945/jn.109.119776 · Cited by 519 · see citing works
Isoflavones: estrogenic activity, biological effect and bioavailability
Vitale, D. C., Piazza, C., Melilli, B., Drago, F., & Salomone, S. (2012) · European Journal of Drug Metabolism and Pharmacokinetics · doi:10.1007/s13318-012-0112-y · Cited by 500 · see citing works
The Interactions between Polyphenols and Microorganisms, Especially Gut Microbiota
Makarewicz, M., Drożdż, I., Tarko, T., & Duda‐Chodak, A. (2021) · Antioxidants · doi:10.3390/antiox10020188 · Cited by 444 · see citing works
Mayo, B., Vázquez, L., & Flórez, A. B. (2019) · Nutrients · doi:10.3390/nu11092231 · Cited by 416 · see citing works
The gut microbiome: an orchestrator of xenobiotic metabolism
Collins, S. L., & Patterson, A. D. (2020) · Acta Pharmaceutica Sinica B · doi:10.1016/j.apsb.2019.12.001 · Cited by 341 · see citing works
Bangsgaard Bendtsen, K. M., Krych, L., Sørensen, D. B., Pang, W., Nielsen, D. S., Josefsen, K., Hansen, L. H., Sørensen, S. J., & Hansen, A. K. (2012) · PLoS ONE · doi:10.1371/journal.pone.0046231 · Cited by 299 · see citing works
The influence of gut microbiota on drug metabolism and toxicity
Li, H., Jiaojiao, H., & Jia, W. P. (2015) · Expert Opinion on Drug Metabolism & Toxicology · doi:10.1517/17425255.2016.1121234 · Cited by 279 · see citing works
Selma, M. V., Beltrán, D., Luna, M. C., Romo‐Vaquero, M., Garcı́a-Villalba, R., Mira, Á., Espı́n, J. C., & Tomás-Barberán, F. A. (2017) · Frontiers in Microbiology · doi:10.3389/fmicb.2017.01521 · Cited by 212 · see citing works
Bioactivation of Phytoestrogens: Intestinal Bacteria and Health
Landete, J. M., Arqués, J. L., Médina, M., Gaya, P., Rivas, B. D. L., & Múñoz, R. (2015) · Critical Reviews in Food Science and Nutrition · doi:10.1080/10408398.2013.789823 · Cited by 204 · see citing works
Emerging evidence of the health benefits of S-equol, an estrogen receptor β agonist
Jackson, R. L., Greiwe, J. S., & Schwen, R. J. (2011) · Nutrition Reviews · doi:10.1111/j.1753-4887.2011.00400.x · Cited by 195 · see citing works
Shortt, C., Hasselwander, O., Meynier, A., Nauta, A., Fernández, E. N., Putz, P., Rowland, I., Swann, J., Türk, J., Vermeiren, J., et al. (2018) · European Journal of Nutrition · doi:10.1007/s00394-017-1546-4 · Cited by 194 · see citing works
A Brief Historical Overview of the Past Two Decades of Soy and Isoflavone Research
Messina, M. J. (2010) · Journal of Nutrition · doi:10.3945/jn.109.118315 · Cited by 185 · see citing works
Isolation of a human intestinal bacterium capable of daidzein and genistein conversion
Matthies, A., Blaut, M., & Braune, A. (2009) · Applied and Environmental Microbiology · doi:10.1128/aem.01795-08 · Cited by 161 · see citing works
Self-citationPhytoestrogen Metabolism by Adult Human Gut Microbiota
Gaya, P., Médina, M., Sánchez‐Jiménez, A., & Landete, J. M. (2016) · Molecules · doi:10.3390/molecules21081034 · Cited by 150 · see citing works
Bioconversion of soy isoflavones daidzin and daidzein by Bifidobacterium strains
Raimondi, S., Roncaglia, L., Lucia, M. D., Amaretti, A., Leonardi, A., PAGNONI, U. M., & Rossi, M. (2008) · Applied Microbiology and Biotechnology · doi:10.1007/s00253-008-1719-4 · Cited by 150 · see citing works
Matthies, A., Loh, G., Blaut, M., & Braune, A. (2011) · Journal of Nutrition · doi:10.3945/jn.111.148247 · Cited by 137 · see citing works
Self-citationWienemann, T., Schmitt‐Wagner, D., Meuser, K., Segelbacher, G., Schink, B., Brune, A., & Berthold, P. R. (2011) · Systematic and Applied Microbiology · doi:10.1016/j.syapm.2011.06.003 · Cited by 129 · see citing works
Clavel, T., Lepage, P., & Charrier, C. (2014) · Springer eBooks · doi:10.1007/978-3-642-30138-4_343 · Cited by 126 · see citing works
Self-citationEnhanced cultured diversity of the mouse gut microbiota enables custom-made synthetic communities
Afrizal, A., Jennings, S. A. V., Hitch, T. C. A., Riedel, T., Basic, M., Panyot, A., Treichel, N. S., Hager, F. T., Wong, E. O.-Y., Wolter, B., et al. (2022) · Cell Host & Microbe · doi:10.1016/j.chom.2022.09.011 · Cited by 125 · see citing works
Self-citationSchröder, C., Matthies, A., Engst, W., Blaut, M., & Braune, A. (2013) · Applied and Environmental Microbiology · doi:10.1128/aem.03693-12 · Cited by 124 · see citing works
Self-citationThe effect of gut microbiota on drug metabolism
Kang, M. J., Kim, H. G., Kim, J. S., Oh, D. G., Um, Y. J., Seo, C. S., Han, J. W., Cho, H. J., Kim, G. H., Jeong, T. C., et al. (2013) · Expert Opinion on Drug Metabolism & Toxicology · doi:10.1517/17425255.2013.807798 · Cited by 120 · see citing works
Das, D., Sarkar, S., Bordoloi, J., Wann, S. B., Kalita, J., & Manna, P. (2018) · BioFactors · doi:10.1002/biof.1439 · Cited by 119 · see citing works
Metabolic and colonic microbiota transformation may enhance the bioactivities of dietary polyphenols
Chiou, Y., Wu, J.-C., Huang, Q., Shahidi, F., Wang, Y., Ho, C., & Pan, M. (2013) · Journal of Functional Foods · doi:10.1016/j.jff.2013.08.006 · Cited by 113 · see citing works
Kumari, N., KUMARI, R. R., Dua, A., Singh, M., Kumar, R., Singh, P., Duyar‐Ayerdi, S., Pradeep, S., Ojesina, A. I., & Kumar, R. (2024) · Molecular Nutrition & Food Research · doi:10.1002/mnfr.202300688 · Cited by 113 · see citing works
Minor tropical fruits as a potential source of bioactive and functional foods
Sarkar, T., Salauddin, M., Roy, A., Sharma, N., Sharma, A., Yadav, S., Jha, V., Ребезов, М. Б., Khayrullin, M., Thiruvengadam, M., et al. (2022) · Critical Reviews in Food Science and Nutrition · doi:10.1080/10408398.2022.2033953 · Cited by 103 · see citing works
Enzymatic Metabolism of Flavonoids by Gut Microbiota and Its Impact on Gastrointestinal Cancer
AL-Ishaq, R. K., Líšková, A., Kubatka, P., & Büsselberg, D. (2021) · Cancers · doi:10.3390/cancers13163934 · Cited by 100 · see citing works
Braune, A., & Blaut, M. (2010) · Environmental Microbiology · doi:10.1111/j.1462-2920.2010.02352.x · Cited by 93 · see citing works
Self-citationRole of Flavonoids in Neurodegenerative Diseases: Limitations and Future Perspectives
Maan, G., Sikdar, B., Kumar, A., Shukla, R., & Mishra, A. (2020) · Current Topics in Medicinal Chemistry · doi:10.2174/1568026620666200416085330 · Cited by 85 · see citing works
(Poly)phenol-related gut metabotypes and human health: an update
Hu, J., Mesnage, R., Tuohy, K. M., Heiß, C., & Rodriguez‐Mateos, A. (2024) · Food & Function · doi:10.1039/d3fo04338j · Cited by 82 · see citing works
Isolation and characterization of the equol-producing bacterium Slackia sp. strain NATTS
Tsuji, H., Moriyama, K., Nomoto, K., Miyanaga, N., & Akaza, H. (2010) · Archives of Microbiology · doi:10.1007/s00203-010-0546-z · Cited by 78 · see citing works
Aboushanab, S. A., Khedr, S. M., Гетте, И. Ф., Danilova, I. G., Кольберг, Н. А., Ravishankar, G. A., Rao, A. R., & Kovaleva, E. G. (2021) · Critical Reviews in Food Science and Nutrition · doi:10.1080/10408398.2021.1946006 · Cited by 75 · see citing works
Clavel, T., Duck, W. L., Charrier, C., Wenning, M., Elson, C. O., & Haller, D. (2009) · INTERNATIONAL JOURNAL OF SYSTEMATIC AND EVOLUTIONARY MICROBIOLOGY · doi:10.1099/ijs.0.015016-0 · Cited by 75 · see citing works
Self-citationKim, M., Kim, S., Han, J., Wang, X., Song, D., & Kim, S.-U. (2009) · Applied and Environmental Microbiology · doi:10.1128/aem.02058-08 · Cited by 73 · see citing works
The metabolic effect of gut microbiota on drugs
Xie, Y., Hu, F., Xiang, D., Lu, H., Li, W., Zhao, A., Huang, L., & Wang, R. (2020) · Drug Metabolism Reviews · doi:10.1080/03602532.2020.1718691 · Cited by 72 · see citing works
Advances in the Metabolic Mechanism and Functional Characteristics of Equol
Gong, Y., Lv, J., Pang, X., Zhang, S., Zhang, G., Liu, L., Wang, Y., & Li, C. (2023) · Foods · doi:10.3390/foods12122334 · Cited by 68 · see citing works
Braune, A., Engst, W., & Blaut, M. (2015) · Environmental Microbiology · doi:10.1111/1462-2920.12864 · Cited by 64 · see citing works
Self-citationChen, L., Tai, W., & Hsiao, W. L. W. (2015) · Journal of Functional Foods · doi:10.1016/j.jff.2015.06.050 · Cited by 65 · see citing works
Cady, N. M., Peterson, S. R., Freedman, S. N., & Mangalam, A. K. (2020) · Frontiers in Neurology · doi:10.3389/fneur.2020.00150 · Cited by 60 · see citing works
Wang, S., Ju, D., & Zeng, X. L. (2024) · Biomedicines · doi:10.3390/biomedicines12010194 · Cited by 60 · see citing works
Metabolism of Daidzein and Genistein by Gut Bacteria of the Class Coriobacteriia
Soukup, S. T., Stoll, D., Danylec, N., Schoepf, A., Kulling, S. E., & Huch, M. (2021) · Foods · doi:10.3390/foods10112741 · Cited by 60 · see citing works
The role of gut microbiota in the pharmacokinetics of antihypertensive drugs
Choi, M. S., Yu, J. S., Yoo, H. H., & Kim, D. (2018) · Pharmacological Research · doi:10.1016/j.phrs.2018.01.019 · Cited by 58 · see citing works
Equol: a metabolite of gut microbiota with potential antitumor effects
Lv, J., Jin, S., Zhang, Y., Zhou, Y., Li, M., & Feng, N. (2024) · Gut Pathogens · doi:10.1186/s13099-024-00625-9 · Cited by 57 · see citing works
Does equol production determine soy endocrine effects?
Shor, D., Sathyapalan, T., Atkin, S. L., & Thatcher, N. J. (2012) · European Journal of Nutrition · doi:10.1007/s00394-012-0331-7 · Cited by 56 · see citing works
Zhang, X., Veliky, C. V., Birru, R. L., Barinas‐Mitchell, E., Magnani, J. W., & Sekikawa, A. M. (2021) · Nutrients · doi:10.3390/nu13113739 · Cited by 54 · see citing works
Kawada, Y., Yokoyama, S., Yanase, E., Niwa, T., & Suzuki, T. (2016) · Bioscience of Microbiota Food and Health · doi:10.12938/bmfh.2015-023 · Cited by 55 · see citing works
Gardana, C., Canzi, E., & Simonetti, P. (2008) · The Journal of Nutritional Biochemistry · doi:10.1016/j.jnutbio.2008.08.006 · Cited by 54 · see citing works
Braune, A., Gütschow, M., & Blaut, M. (2019) · Applied and Environmental Microbiology · doi:10.1128/aem.01233-19 · Cited by 53 · see citing works
Self-citationTrapping Methylglyoxal by Genistein and Its Metabolites in Mice
Wang, P., Chen, H., & Sang, S. (2016) · Chemical Research in Toxicology · doi:10.1021/acs.chemrestox.5b00516 · Cited by 52 · see citing works
Identification of Two Novel Reductases Involved in Equol Biosynthesis in Lactococcus Strain 20–92
Shimada, Y., Takahashi, M., Miyazawa, N., Ohtani, T., Abiru, Y., Uchiyama, S., & Hishigaki, H. (2011) · Microbial Physiology · doi:10.1159/000335049 · Cited by 49 · see citing works
Gao, X., Mu, P., Zhu, X., Chen, X., Tang, S., Wu, Y., Miao, X., Wang, X., Wen, J., & Deng, Y. (2020) · Toxins · doi:10.3390/toxins12020085 · Cited by 49 · see citing works
The degradation of curcuminoids in a human faecal fermentation model
Tan, S., Calani, L., Bresciani, L., Dall’Asta, M., Faccini, A., Augustin, M. A., Gras, S. L., & Rio, D. D. (2015) · International Journal of Food Sciences and Nutrition · doi:10.3109/09637486.2015.1095865 · Cited by 48 · see citing works
Flavonoid-Based Cancer Therapy: An Updated Review.
Hosseinzadeh, E., Hassanzadeh, A., Marofi, F., Alivand, M., & Solali, S. (2020) · Anti-Cancer Agents in Medicinal Chemistry · doi:10.2174/1871520620666200423071759 · Cited by 42 · see citing works
Potential Impact of Probiotic Consumption on the Bioactivity of Dietary Phytochemicals
Rossi, M., Amaretti, A., Leonardi, A., Raimondi, S., Simone, M., & Quartieri, A. (2013) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf402722m · Cited by 45 · see citing works
Lee, P., Kim, J., Kim, E., Lee, S.-H., Choi, K.-Y., Kazlauskas, R. J., & Kim, B. (2017) · ACS Chemical Biology · doi:10.1021/acschembio.7b00624 · Cited by 44 · see citing works
Leonard, L. M., Choi, M. S., & Cross, T.-W. (2022) · Nutrients · doi:10.3390/nu14030553 · Cited by 43 · see citing works
Antihyperglycemic effect of equol, a daidzein derivative, in cultured L6 myocytes and ob/ob mice
Cheong, S. H., Furuhashi, K., Ito, K., Nagaoka, M., Yonezawa, T., Miura, Y., & Yagasaki, K. (2013) · Molecular Nutrition & Food Research · doi:10.1002/mnfr.201300272 · Cited by 40 · see citing works
Anticancer Mechanism of Flavonoids on High-Grade Adult-Type Diffuse Gliomas
Wong, S. C., Kamarudin, M. N. A., & Naidu, R. (2023) · Nutrients · doi:10.3390/nu15040797 · Cited by 40 · see citing works
Prebiotic Potential of Culinary Spices Used to Support Digestion and Bioabsorption
Peterson, C. T., Rodionov, D. A., Iablokov, S. N., Pung, M. A., Chopra, D., Mills, P. J., & Peterson, S. N. (2019) · Evidence-based Complementary and Alternative Medicine · doi:10.1155/2019/8973704 · Cited by 38 · see citing works
Garg, S. K., Shukla, A. K., & Choudhury, S. (2019) · Springer eBooks · doi:10.1007/978-3-030-04624-8_13 · Cited by 37 · see citing works
Luminal Conversion and Immunoregulation by Probiotics
Ganesh, B. P., & Versalovic, J. A. (2015) · Frontiers in Pharmacology · doi:10.3389/fphar.2015.00269 · Cited by 37 · see citing works
Flórez, A. B., Vázquez, L., Rodríguez, J., Redruello, B., & Mayo, B. (2019) · Nutrients · doi:10.3390/nu11050993 · Cited by 36 · see citing works
Combination of Genistin and Fructooligosaccharides Prevents Bone Loss in Ovarian Hormone Deficiency
Hooshmand, S., Juma, S., & Arjmandi, B. H. (2010) · Journal of Medicinal Food · doi:10.1089/jmf.2009.0059 · Cited by 33 · see citing works
Clavel, T., & Mapesa, J. O. (2013) · Springer eBooks · doi:10.1007/978-3-642-22144-6_94 · Cited by 31 · see citing works
Self-citationWang, X., Chen, B., Fang, X., Zhong, Q., Liao, Z., Wang, J., Wu, X., Ma, Y., Li, P., Feng, X., et al. (2022) · Critical Reviews in Food Science and Nutrition · doi:10.1080/10408398.2022.2154744 · Cited by 31 · see citing works
Wang, Q., Spenkelink, B., Boonpawa, R., Rietjens, I. M. C. M., & Beekmann, K. (2020) · Molecular Nutrition & Food Research · doi:10.1002/mnfr.201900912 · Cited by 29 · see citing works
The effect of equol injection in ovo on posthatch growth, meat quality and antioxidation in broilers
Wei, X. J., Ni, Y., Lu, L., Grossmann, R., & Zhao, R. (2010) · animal · doi:10.1017/s1751731110001771 · Cited by 28 · see citing works
Abiru, Y., Ueno, T., & Uchiyama, S. (2013) · International Journal of Food Sciences and Nutrition · doi:10.3109/09637486.2013.816936 · Cited by 28 · see citing works
Germán-Ponciano, L. J., Rosas-Sánchez, G. U., Cueto‐Escobedo, J., Fernández-Demeneghi, R., Guillén-Ruiz, G., Soria-Fregozo, C., Herrera-Huerta, E. V., & Rodríguez‐Landa, J. F. (2022) · International Journal of Molecular Sciences · doi:10.3390/ijms231810896 · Cited by 26 · see citing works
Flavonoids: Health Benefits and Their Potential Use in Food Systems
Manzoor, A., Dar, I. H., Bhat, S. A., & Ahmad, S. (2020) · Springer eBooks · doi:10.1007/978-981-15-4716-4_15 · Cited by 25 · see citing works
Singla, N., Gupta, G., Kulshrestha, R., Sharma, K., Bhat, A. A., Mishra, R., Patel, N. K., Thapa, R., Ali, H., Mishra, A., et al. (2024) · Pharmacological Research - Modern Chinese Medicine · doi:10.1016/j.prmcm.2024.100460 · Cited by 26 · see citing works
Treatment strategies for psoriasis using flavonoids from traditional Chinese medicine
Gupta, A., Jain, P., Nagori, K., Adnan, M., & Ajazuddin, M. (2024) · Pharmacological Research - Modern Chinese Medicine · doi:10.1016/j.prmcm.2024.100463 · Cited by 24 · see citing works
Recent advances in the microbial hydroxylation and reduction of soy isoflavones
Lee, P., Lee, U., Song, H., Choi, K., & Kim, B. (2018) · FEMS Microbiology Letters · doi:10.1093/femsle/fny195 · Cited by 23 · see citing works
Yusakul, G., Sakamoto, S., Juengwatanatrakul, T., Putalun, W., Tanaka, H., & Morimoto, S. (2015) · Phytochemical Analysis · doi:10.1002/pca.2604 · Cited by 22 · see citing works
Advances in equol production: Sustainable strategies for unlocking soy isoflavone benefits
Ortíz, C., & Manta, B. (2024) · Results in Chemistry · doi:10.1016/j.rechem.2023.101288 · Cited by 19 · see citing works
Huang, P., Mou, Q., Yang, Y., Li, J., Xu, M., Huang, J., Li, J., Yang, H., Liang, X., & Yin, Y. (2021) · Veterinary Medicine and Science · doi:10.1002/vms3.450 · Cited by 19 · see citing works
Zhao, H., Wang, X., Zhang, H., Li, C.-D., & Wang, S. (2011) · Applied Microbiology and Biotechnology · doi:10.1007/s00253-011-3278-3 · Cited by 17 · see citing works
Gut microbiota: what is its place in pharmacology?
Tarasiuk, A., & Fichna, J. (2019) · Expert Review of Clinical Pharmacology · doi:10.1080/17512433.2019.1670058 · Cited by 17 · see citing works
Pharmacokinetics of Dietary Isoflavones
Annie Aglin, A. (2013) · Journal of Steroids & Hormonal Science · doi:10.4172/2157-7536.s12-004 · Cited by 17 · see citing works
Braune, A., & Blaut, M. (2017) · Journal of Applied Microbiology · doi:10.1111/jam.13616 · Cited by 17 · see citing works
Self-citationFlavonoids and anticancer activity: Structure–activity relationship
Çetinkaya, S., Akça, K. T., & Süntar, I. P. (2022) · Studies in natural products chemistry · doi:10.1016/b978-0-323-91099-6.00017-7 · Cited by 16 · see citing works
A mechanism-based understanding of altered drug pharmacokinetics by gut microbiota
Gulnaz, A., Chang, J., Maeng, H., Shin, K., Lee, K., & Chae, Y. (2022) · Journal of Pharmaceutical Investigation · doi:10.1007/s40005-022-00600-z · Cited by 17 · see citing works
Bioavailability and Nutritional Analysis of Flavonoids
Meena, N. L., Verma, P., Pande, R., Kumar, M., Watts, A., & Gupta, O. P. (2020) · Springer eBooks · doi:10.1007/978-981-15-4890-1_6 · Cited by 12 · see citing works
Zhang, X., Fujiyoshi, A., Kadota, A., Kondo, K., Torii, S., Okami, Y., Hisamatsu, T., Yano, Y., Barinas‐Mitchell, E., Magnani, J. W., et al. (2022) · Scientific Reports · doi:10.1038/s41598-022-24659-8 · Cited by 12 · see citing works
Gao, Y., Hao, Q.-H., Zhang, H., Zhou, B., Yu, X.-M., & Wang, X.-L. (2016) · Letters in Applied Microbiology · doi:10.1111/lam.12594 · Cited by 12 · see citing works
Flavonoid-derived Privileged Scaffolds in anti-Trypanosoma brucei Drug Discovery
Kamdem, B. P., & Elizabeth, F. I. (2019) · Current Drug Targets · doi:10.2174/1389450120666190618114857 · Cited by 12 · see citing works
Tamura, M., Hori, S., & Nakagawa, H. (2014) · Food Science and Technology Research · doi:10.3136/fstr.20.309 · Cited by 12 · see citing works
Nguyen, V. D., Min, B.-C., Kyung, M.-O., Park, J., Lee, B. H., Choi, C., Seo, N.-S., Kim, Y.-R., Ahn, D. U., Lee, S., et al. (2009) · Phytochemical Analysis · doi:10.1002/pca.1146 · Cited by 11 · see citing works
Bastos, T. S., Souza, C. M. M., Kaelle, G. C. B., do Nascimento, M. Q., de Oliveira, S. G., & Félix, A. P. (2023) · Journal of Animal Physiology and Animal Nutrition · doi:10.1111/jpn.13824 · Cited by 9 · see citing works
A Review on the Role of Phytoconstituents Chrysin on the Protective Effect on Liver and Kidney
Sarmah, D. K., & Sengupta, R. (2023) · Current Drug Discovery Technologies · doi:10.2174/0115701638242317231018144944 · Cited by 9 · see citing works
Flavonoids, an Overview: Chemical Structures, Dietary Sources, and Biological Properties
Kim, J.-S. (2020) · Food Engineering Progress · doi:10.13050/foodengprog.2020.24.3.151 · Cited by 9 · see citing works
Guo, X., Zang, X., Dou, S., Wang, D., & Wang, X. (2022) · Journal of the Science of Food and Agriculture · doi:10.1002/jsfa.12087 · Cited by 9 · see citing works
Potential of Flavonoids as Anticancer Drugs
Kumar, P., Dixit, J., Saini, R., Verma, P., Mishra, A. K., & NathTiwari, K. (2021) · doi:10.1002/9781119682059.ch7 · Cited by 9 · see citing works
The Preparation of Gen-NH2-MCM-41@SA Nanoparticles and Their Anti-Rotavirus Effects
Song, L., Chen, J., Feng, Y., Zhou, Y., Li, F., Dai, G., Yuan, Y., Yi, H., Qian, Y., Yang, S., et al. (2022) · Pharmaceutics · doi:10.3390/pharmaceutics14071337 · Cited by 8 · see citing works
Ni, Y., Wei, X., Zhang, C. X., Zhong, Y., Lu, L. Z., Grossmann, R., & Zhao, R. (2012) · animal · doi:10.1017/s1751731112000468 · Cited by 8 · see citing works
Flavonoids: a key component of cosmeceuticals
Andrabi, N. I., Kumar, D., & Sawhney, G. (2024) · Elsevier eBooks · doi:10.1016/b978-0-443-19148-0.00003-6 · Cited by 7 · see citing works
Kim, M., & Han, J. (2014) · Bulletin of the Korean Chemical Society · doi:10.5012/bkcs.2014.35.6.1883 · Cited by 7 · see citing works
Bioactive Flavonoid Apigenin and Its Nanoformulations: A Promising Hope for Diabetes and Cancer
Mukherjee, B., Banerjee, S., Mondal, L., Chakraborty, S., Chanda, D., & Perera, J. A. C. (2020) · Springer eBooks · doi:10.1007/978-981-15-1664-1_13 · Cited by 7 · see citing works
Advances on resource, biosynthesis pathway, bioavailability, and bioactivity of dihydrodaidzein
Zou, P., Chen, S., Otero, P., & Cao, H. (2025) · Phytochemistry Reviews · doi:10.1007/s11101-025-10124-7 · Cited by 6 · see citing works
- Authors
- Matthies, A., Clavel, T., Gütschow, M., Engst, W., Haller, D., Blaut, M., & Braune, A.
- Affiliations
- German Institute of Human Nutrition (DE)
- Technical University of Munich (DE)
- Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany
- Department of Gastrointestinal Microbiology
- Corresponding author
- Braune, Annett
- Venue
- Applied and Environmental Microbiology
- Publisher
- American Society for Microbiology
- Published
- 2008-08
- Volume
- 74
- Issue
- 15
- Pages
- 4847-4852
- ISSN
- 0099-2240 (ISSN-L)
- 1098-5336
- PMC
- PMC2519357
- OpenAlex
- W2067334985
- Cited by
- 141
- References
- 57
- Citations by year
- 2026: 7 · 2025: 4 · 2024: 16 · 2023: 9 · 2022: 15 · 2021: 9 · 2020: 10 · 2019: 11 · 2018: 5 · 2017: 5 · 2016: 6 · 2015: 8 · 2014: 5 · 2013: 8 · 2012: 6
- FWCI
- 4.02
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- Applied and Environmental Microbiology (publishedVersion)
- Europe PMC (PubMed Central) (publishedVersion)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Deutsche Forschungsgemeinschaft
- Topics
- Health Sciences › Medicine › Pathology and Forensic Medicine › Phytoestrogen effects and research
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Gut microbiota and health
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biotechnology › Biochemical and biochemical processes
- Keywords
- daidzein, genistein, isoflavone metabolism, equol, dihydrodaidzein, gut microbiota, Coriobacteriaceae, anaerobic bacteria, enzyme induction, soy isoflavones, mouse intestine, metabolic activation
- MeSH terms
- Animals, Bacteria, Anaerobic, Biotransformation, Chromatography, High Pressure Liquid, Female, Gram-Positive Bacteria, Ileum, Isoflavones, Mice, Inbred C57BL, Molecular Sequence Data, Genistein, Spectrometry, Mass, Electrospray Ionization, Mice
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