Chemical transformation of xenobiotics by the human gut microbiota
Open accessAbstract
The human gut microbiota makes key contributions to the metabolism of ingested compounds (xenobiotics), transforming hundreds of dietary components, industrial chemicals, and pharmaceuticals into metabolites with altered activities, toxicities, and lifetimes within the body. The chemistry of gut microbial xenobiotic metabolism is often distinct from that of host enzymes. Despite their important consequences for human biology, the gut microbes, genes, and enzymes involved in xenobiotic metabolism are poorly understood. Linking these microbial transformations to enzymes and elucidating their biological effects is undoubtedly challenging. However, recent studies demonstrate that integrating traditional and emerging technologies can enable progress toward this goal. Ultimately, a molecular understanding of gut microbial xenobiotic metabolism will guide personalized medicine and nutrition, inform toxicology risk assessment, and improve drug discovery and development.
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The most common biotransformations carried out by the gut microbiome, hydrolysis and reduction, often undo the oxidative and conjugative chemistry and the intended eliminative purpose of host hepatic drug metabolism.
“the most common biotransformations carried out by the gut microbiome (hydrolysis and reduction) often serve to undo the oxidative and conjugative chemistry and indeed the intended eliminative purpose of host hepatic drug metabolism (Koppel et al., 2017).”
From Gut reactions: Breaking down xenobiotic–microbiome interactions (2019) · cites this paper as Koppel et al., 2017
Gut microbiome reactions frequently release small molecules or carbon sources that can be used for microbial growth.
“The reactions carried out by the gut microbiome frequently result in the release of small molecules or carbon sources that can be used for microbial growth (Koppel et al., 2017).”
From Gut reactions: Breaking down xenobiotic–microbiome interactions (2019) · cites this paper as Koppel et al., 2017
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Cites
Structure, function and diversity of the healthy human microbiome
The Human Microbiome Project Consortium (2012) · Nature · doi:10.1038/nature11234 · Cited by 11,726 · see citing works
Diversity of the Human Intestinal Microbial Flora
Eckburg, P. B., Bik, E. M., Bernstein, C. N., Purdom, E., Dethlefsen, L., Sargent, M., Gill, S. R., Nelson, K. E., & Relman, D. A. (2005) · Science · doi:10.1126/science.1110591 · Cited by 7,913 · see citing works
From Dietary Fiber to Host Physiology: Short-Chain Fatty Acids as Key Bacterial Metabolites
Koh, A., De Vadder, F., Kovatcheva-Datchary, P., & Bäckhed, F. (2016) · Cell · doi:10.1016/j.cell.2016.05.041 · Cited by 7,070 · see citing works
Revised Estimates for the Number of Human and Bacteria Cells in the Body
Sender, R., Fuchs, S., & Milo, R. (2016) · PLOS Biology · doi:10.1371/journal.pbio.1002533 · Cited by 5,425 · see citing works
Anticancer immunotherapy by CTLA-4 blockade relies on the gut microbiota
Vétizou, M., Pitt, J. M., Daillère, R., Lepage, P., Waldschmitt, N., Flament, C., Rusakiewicz, S., Routy, B., Roberti, M. P., Duong, C. P. M., et al. (2015) · Science · doi:10.1126/science.aad1329 · Cited by 3,488 · see citing works
Personalized nutrition by prediction of glycemic responses
Zeevi, D., Korem, T., Zmora, N., Israeli, D., Rothschild, D., Weinberger, A., Ben-Yacov, O., Lador, D., Avnit-Sagi, T., Lotan-Pompan, M., et al. (2015) · Cell · doi:10.1016/j.cell.2015.11.001 · Cited by 2,929 · see citing works
Metabolomics analysis reveals large effects of gut microflora on mammalian blood metabolites
Wikoff, W. R., Anfora, A. T., Liu, J., Schultz, P. G., Lesley, S. A., Peters, E. C., & Siuzdak, G. (2009) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0812874106 · Cited by 2,677 · see citing works
An integrated catalog of reference genes in the human gut microbiome
MetaHIT Consortium, Li, J., Jia, H., Cai, X., Zhong, H., Feng, Q., Sunagawa, S., Arumugam, M., Kultima, J. R., Prifti, E., et al. (2014) · Nature Biotechnology · doi:10.1038/nbt.2942 · Cited by 2,164 · see citing works
Genomic insights that advance the species definition for prokaryotes
Konstantinidis, K. T., & Tiedje, J. M. (2005) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0409727102 · Cited by 2,124 · see citing works
The microbiome and butyrate regulate energy metabolism and autophagy in the mammalian colon
Donohoe, D. R., Garge, N., Zhang, X., Sun, W., O'Connell, T. M., Bunger, M. K., & Bultman, S. J. (2011) · Cell Metabolism · doi:10.1016/j.cmet.2011.02.018 · Cited by 2,003 · see citing works
Blundell, J. E., Baker, J. L., Boyland, E. J., Blaak, E. E., Charzewska, J., Henauw, S. D., Frühbeck, G., González‐Gross, M., Hebebrand, J., Holm, L., et al. (2017) · Obesity Facts · doi:10.1159/000455952 · Cited by 1,980 · see citing works
Precision microbiome reconstitution restores bile acid mediated resistance to Clostridium difficile
Buffie, C. G., Bucci, V., Stein, R. R., McKenney, P. T., Ling, L., Gobourne, A., No, D., Liu, H., Kinnebrew, M., Viale, A., et al. (2015) · Nature · doi:10.1038/nature13828 · Cited by 1,872 · see citing works
Polysaccharide utilization by gut bacteria: potential for new insights from genomic analysis
Flint, H. J., Bayer, E. A., Rincón, M. T., Lamed, R., & White, B. A. (2008) · Nature Reviews Microbiology · doi:10.1038/nrmicro1817 · Cited by 1,710 · see citing works
The abundance and variety of carbohydrate-active enzymes in the human gut microbiota
Kaoutari, A. E., Armougom, F., Gordon, J. I., Raoult, D., & Henrissat, B. (2013) · Nature Reviews Microbiology · doi:10.1038/nrmicro3050 · Cited by 1,683 · see citing works
Shin, N.-R., Lee, J.-C., Lee, H.-Y., Kim, M.-S., Whon, T. W., Lee, M.-S., & Bae, J.-W. (2014) · Gut · doi:10.1136/gutjnl-2012-303839 · Cited by 1,550 · see citing works
The central nervous system and the gut microbiome
Sharon, G., Sampson, T. R., Geschwind, D. H., & Mazmanian, S. K. (2016) · Cell · doi:10.1016/j.cell.2016.10.027 · Cited by 1,513 · see citing works
How glycan metabolism shapes the human gut microbiota
Koropatkin, N. M., Cameron, E. A., & Martens, E. C. (2012) · Nature Reviews Microbiology · doi:10.1038/nrmicro2746 · Cited by 1,419 · see citing works
Wang, Z., Roberts, A. B., Buffa, J. A., Levison, B. S., Zhu, W., Org, E., Gu, X., Huang, Y., Zamanian-Daryoush, M., Culley, M. K., et al. (2015) · Cell · doi:10.1016/j.cell.2015.11.055 · Cited by 1,317 · see citing works
Symbiotic gut microbes modulate human metabolic phenotypes
Li, M., Wang, B., Zhang, M., Rantalainen, M., Wang, S., Zhou, H., Zhang, Y., Shen, J., Pang, X., Zhang, M., et al. (2008) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0712038105 · Cited by 1,144 · see citing works
Alleviating Cancer Drug Toxicity by Inhibiting a Bacterial Enzyme
Wallace, B. D., Wang, H., Lane, K. T., Scott, J. E., Orans, J., Koo, J. S., Venkatesh, M., Jobin, C., Yeh, L.-A., Mani, S., et al. (2010) · Science · doi:10.1126/science.1191175 · Cited by 1,080 · see citing works
Comparative metagenomics revealed commonly enriched gene sets in human gut microbiomes
Kurokawa, K., Itoh, T., Kuwahara, T., Oshima, K., Toh, H., Toyoda, A., Takami, H., Morita, H., Sharma, V. K., Srivastava, T. P., et al. (2007) · DNA Research · doi:10.1093/dnares/dsm018 · Cited by 869 · see citing works
Gerlt, J. A., Bouvier, J. T., Davidson, D. B., Imker, H. J., Sadkhin, B., Slater, D. R., & Whalen, K. L. (2015) · Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics · doi:10.1016/j.bbapap.2015.04.015 · Cited by 805 · see citing works
Role of Microbial Enzymes in the Bioremediation of Pollutants: A Review
Karigar, C. S., & Rao, S. S. (2011) · Enzyme Research · doi:10.4061/2011/805187 · Cited by 795 · see citing works
Romano, K. A., Vivas, E. I., Amador-Noguez, D., & Rey, F. E. (2015) · mBio · doi:10.1128/mbio.02481-14 · Cited by 777 · see citing works
Clayton, T. A., Baker, D., Lindon, J. C., Everett, J. R., & Nicholson, J. K. (2009) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0904489106 · Cited by 765 · see citing works
Williams, B. B., Van Benschoten, A. H., Cimermancic, P., Donia, M. S., Zimmermann, M., Taketani, M., Ishihara, A., Kashyap, P. C., Fraser, J. S., & Fischbach, M. A. (2014) · Cell Host & Microbe · doi:10.1016/j.chom.2014.09.001 · Cited by 732 · see citing works
The microbial pharmacists within us: a metagenomic view of xenobiotic metabolism
Spanogiannopoulos, P., Bess, E. N., Carmody, R. N., & Turnbaugh, P. J. (2016) · Nature Reviews Microbiology · doi:10.1038/nrmicro.2016.17 · Cited by 717 · see citing works
Haiser, H. J., Gootenberg, D. B., Chatman, K., Sirasani, G., Balskus, E. P., & Turnbaugh, P. J. (2013) · Science · doi:10.1126/science.1235872 · Cited by 704 · see citing works
Self-citationA Catalog of Reference Genomes from the Human Microbiome
The Human Microbiome Jumpstart Reference Strains Consortium, Nelson, K. E., Weinstock, G. M., Highlander, S. K., Worley, K. C., Creasy, H. H., Wortman, J. R., Rusch, D. B., Mitreva, M., Sodergren, E., et al. (2010) · Science · doi:10.1126/science.1183605 · Cited by 702 · see citing works
Microbial conversion of choline to trimethylamine requires a glycyl radical enzyme
Craciun, S., & Balskus, E. P. (2012) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1215689109 · Cited by 701 · see citing works
Self-citationThe gut microbiota: a major player in the toxicity of environmental pollutants?
Claus, S. P., Guillou, H., & Ellero-Simatos, S. (2016) · npj Biofilms and Microbiomes · doi:10.1038/npjbiofilms.2016.3 · Cited by 678 · see citing works
The gastrointestinal microbiota as a site for the biotransformation of drugs
Sousa, T., Paterson, R., Moore, V., Carlsson, A., Abrahamsson, B., & Basit, A. W. (2008) · International Journal of Pharmaceutics · doi:10.1016/j.ijpharm.2008.07.009 · Cited by 618 · see citing works
PHASE II DRUG METABOLIZING ENZYMES
Jancova, P., Anzenbacher, P., & Anzenbacherová, E. (2010) · Biomedical Papers · doi:10.5507/bp.2010.017 · Cited by 611 · see citing works
Cospeciation of gut microbiota with hominids
Moeller, A. H., Caro‐Quintero, A., Mjungu, D. C., Georgiev, A. V., Lonsdorf, E. V., Muller, M. N., Pusey, A. E., Peeters, M., Hahn, B. H., & Ochman, H. (2016) · Science · doi:10.1126/science.aaf3951 · Cited by 570 · see citing works
Specialized metabolites from the microbiome in health and disease
Sharon, G., Garg, N., Debelius, J., Knight, R., Dorrestein, P. C., & Mazmanian, S. K. (2014) · Cell Metabolism · doi:10.1016/j.cmet.2014.10.016 · Cited by 544 · 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
Cross, A. J., Ferrucci, L. M., Risch, A., Graubard, B. I., Ward, M. H., Park, Y., Hollenbeck, A. R., Schatzkin, A., & Sinha, R. (2010) · Cancer Research · doi:10.1158/0008-5472.can-09-3929 · Cited by 469 · see citing works
Blachier, F., Mariotti, F., Huneau, J. F., & Tomé, D. (2007) · Amino Acids · doi:10.1007/s00726-006-0477-9 · Cited by 452 · see citing works
THE ROLE OF INTESTINAL BACTERIA IN THE METABOLISM OF SALICYLAZOSULFAPYRIDINE
PEPPERCORN, M. A., & GOLDMAN, P. (1972) · The Journal of Pharmacology and Experimental Therapeutics · doi:10.1016/s0022-3565(25)29238-2 · Cited by 450 · see citing works
Inactivation of Digoxin by the Gut Flora: Reversal by Antibiotic Therapy
Lindenbaum, J., Rund, D. G., Butler, V. P., Tse-Eng, D., & Saha, J. R. (1981) · New England Journal of Medicine · doi:10.1056/nejm198110013051403 · Cited by 423 · see citing works
Dujovne, C. A., Ettinger, M. P., McNeer, J. F., Lipka, L., LeBeaut, A., Suresh, R., Yang, B., & Veltri, E. P. (2002) · The American Journal of Cardiology · doi:10.1016/s0002-9149(02)02798-4 · Cited by 390 · see citing works
Fennema, D., Phillips, I. R., & Shephard, E. A. (2016) · Drug Metabolism and Disposition · doi:10.1124/dmd.116.070615 · Cited by 355 · see citing works
Azoreductase activity of anaerobic bacteria isolated from human intestinal microflora
Rafii, F., Franklin, W., & Cerniglia, C. E. (1990) · Applied and Environmental Microbiology · doi:10.1128/aem.56.7.2146-2151.1990 · Cited by 340 · see citing works
Melamine and the Global Implications of Food Contamination
Ingelfinger, J. R. (2008) · New England Journal of Medicine · doi:10.1056/nejmp0808410 · Cited by 334 · see citing works
Degradation of steroids in the human gut
MacDonald, I. A., Bokkenheuser, V. D., Winter, J., Cerone-McLernon, A. M., & Mosbach, E. H. (1983) · Journal of Lipid Research · doi:10.1016/s0022-2275(20)37944-x · Cited by 332 · see citing works
Lukatela, G., Krauß, N., Theis, K. W., Selmer, T., Gieselmann, V., FIGURA, K. V., & Saenger, W. (1998) · Biochemistry · doi:10.1021/bi9714924 · Cited by 326 · see citing works
Local bacteria affect the efficacy of chemotherapeutic drugs
Lehouritis, P., Cummins, J., Stanton, M., Murphy, C. T., McCarthy, F. O., Reid, G., Urbaniak, C., Byrne, W. L., & Tangney, M. (2015) · Scientific Reports · doi:10.1038/srep14554 · Cited by 313 · see citing works
Transforming berberine into its intestine-absorbable form by the gut microbiota
Feng, R., Shou, J.-W., Zhao, Z.-X., He, C.-Y., Ma, C., Huang, M., Fu, J., Tan, X.-S., Li, X.-Y., Wen, B.-Y., et al. (2015) · Scientific Reports · doi:10.1038/srep12155 · Cited by 307 · see citing works
Modulation of a Circulating Uremic Solute via Rational Genetic Manipulation of the Gut Microbiota
Devlin, A. S., Marcobal, A. M., Dodd, D., Nayfach, S., Plummer, N. S., Meyer, T., Pollard, K. S., Sonnenburg, J. L., & Fischbach, M. A. (2016) · Cell Host & Microbe · doi:10.1016/j.chom.2016.10.021 · Cited by 300 · see citing works
The response to levodopa in parkinson's disease: Imposing pharmacological law and order
Nutt, J. G., & Holford, N. H. G. (1996) · Annals of Neurology · doi:10.1002/ana.410390504 · Cited by 299 · see citing works
Linhardt, R. J., Galliher, P. M., & Cooney, C. L. (1987) · Applied Biochemistry and Biotechnology · doi:10.1007/bf02798420 · Cited by 289 · see citing works
Wallace, B. D., Roberts, A. B., Pollet, R. M., Ingle, J. D., Biernat, K. A., Pellock, S. J., Venkatesh, M. K., Guthrie, L., O’Neal, S. K., Robinson, S. J., et al. (2015) · Chemistry & Biology · doi:10.1016/j.chembiol.2015.08.005 · Cited by 285 · see citing works
Functional metagenomics to mine the human gut microbiome for dietary fiber catabolic enzymesPreprint
Tasse, L., Bercovici, J., Pizzut‐Serin, S., Robe, P., Tap, J., Klopp, C., Cantarel, B. L., Coutinho, P. M., Henrissat, B., Leclerc, M., et al. (2010) · Genome Research · doi:10.1101/gr.108332.110 · Cited by 276 · see citing works
The importance of the gut microbiota after bariatric surgery
Aron‐Wisnewsky, J., Dore, J. M., & Clément, K. (2012) · Nature Reviews Gastroenterology & Hepatology · doi:10.1038/nrgastro.2012.161 · Cited by 259 · see citing works
Digoxin-Inactivating Bacteria: Identification in Human Gut Flora
Dobkin, J. F., Saha, J. R., Butler, V. P., Neu, H. C., & Lindenbaum, J. (1983) · Science · doi:10.1126/science.6836275 · Cited by 259 · see citing works
Caminero, A., Galipeau, H. J., McCarville, J. L., Johnston, C. W., Bernier, S. P., Russell, A. K., Jury, J., Herran, A. R., Casqueiro, J., Tye-Din, J. A., et al. (2016) · Gastroenterology · doi:10.1053/j.gastro.2016.06.041 · Cited by 250 · see citing works
Host-compound foraging by intestinal microbiota revealed by single-cell stable isotope probing
Berry, D., Stecher, B., Schintlmeister, A., Reichert, J., Brugiroux, S., Wild, B., Wanek, W., Richter, A., Rauch, I., Decker, T., et al. (2013) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1219247110 · Cited by 246 · see citing works
A Clinical Trial of Amygdalin (Laetrile) in the Treatment of Human Cancer
Moertel, C. G., Fleming, T. R., Rubin, J., et al. (1982) · New England Journal of Medicine · doi:10.1056/nejm198201283060403 · Cited by 246 · see citing works
The relationship between phenolic compounds from diet and microbiota: impact on human health
Valdés, L., Cuervo, A. J. V., Salazar, N., Ruas‐Madiedo, P., Gueimonde, M., & González, S. (2015) · Food & Function · doi:10.1039/c5fo00322a · Cited by 236 · see citing works
Martínez-del Campo, A., Bodea, S., Hamer, H. A., Marks, J. A., Haiser, H. J., Turnbaugh, P. J., & Balskus, E. P. (2015) · mBio · doi:10.1128/mbio.00042-15 · Cited by 224 · see citing works
Self-citationGenomic sequencing of uncultured microorganisms from single cells
Lasken, R. S. (2012) · Nature Reviews Microbiology · doi:10.1038/nrmicro2857 · Cited by 221 · see citing works
Trimethylamine- N -Oxide: Friend, Foe, or Simply Caught in the Cross-Fire?
Cho, C. E., & Caudill, M. A. (2016) · Trends in Endocrinology and Metabolism · doi:10.1016/j.tem.2016.10.005 · Cited by 218 · see citing works
Rafii, F., Hall, J., & Cerniglia, C. E. (1997) · Food and Chemical Toxicology · doi:10.1016/s0278-6915(97)00060-4 · Cited by 216 · see citing works
Selmer, T., & Andrei, P. I. (2001) · European Journal of Biochemistry · doi:10.1046/j.1432-1327.2001.02001.x · Cited by 214 · see citing works
Drug Delivery: Principles and Applications
Wang, B., Siahaan, T. J., & Soltero, R. A. (2005) · Cited by 209 · see citing works
Clavel, T., Henderson, G., Engst, W., Dore, J. M., & Blaut, M. (2006) · FEMS Microbiology Ecology · doi:10.1111/j.1574-6941.2005.00057.x · Cited by 209 · see citing works
Time course production of urolithins from ellagic acid by human gut microbiota
García-Villalba, R., Beltrán, D., Espín, J. C., Selma, M. V., & Tomás-Barberán, F. A. (2013) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf402498b · Cited by 207 · see citing works
Kolmeder, C. A., de Been, M., Nikkilä, J., Ritamo, I., Mättö, J., Valmu, L., Salojärvi, J., Palva, A., Salonen, A., & de Vos, W. M. (2012) · PLoS ONE · doi:10.1371/journal.pone.0029913 · Cited by 199 · see citing works
Buckel, W., & Golding, B. T. (2006) · Annual Review of Microbiology · doi:10.1146/annurev.micro.60.080805.142216 · Cited by 193 · see citing works
Saitta, K. S., Zhang, C., Lee, K. K., Fujimoto, K., Redinbo, M. R., & Boelsterli, U. A. (2014) · Xenobiotica · doi:10.3109/00498254.2013.811314 · Cited by 165 · see citing works
Melamine-Induced Renal Toxicity Is Mediated by the Gut Microbiota
Zheng, X., Zhao, A., Xie, G., Chi, Y., Zhao, L., Li, H., Wang, C., Bao, Y., Jia, W., Luther, M., et al. (2013) · Science Translational Medicine · doi:10.1126/scitranslmed.3005114 · Cited by 151 · see citing works
Liu, Y., Zhang, J.-W., Li, W., et al. (2006) · Toxicological Sciences · doi:10.1093/toxsci/kfj164 · Cited by 145 · see citing works
A prominent glycyl radical enzyme in human gut microbiomes metabolizes trans -4-hydroxy- l -proline
Levin, B. J., Huang, Y. Y., Peck, S. C., Wei, Y., Campo, A. M.-D., Marks, J. A., Franzosa, E. A., Huttenhower, C., & Balskus, E. P. (2017) · Science · doi:10.1126/science.aai8386 · Cited by 142 · see citing works
Self-citationThe metabolism of intense sweeteners
Renwick, A. G. C. (1986) · Xenobiotica · doi:10.3109/00498258609038983 · Cited by 139 · see citing works
Characterization of Choline Trimethylamine-Lyase Expands the Chemistry of Glycyl Radical Enzymes
Craciun, S., Marks, J. A., & Balskus, E. P. (2014) · ACS Chemical Biology · doi:10.1021/cb500113p · Cited by 139 · see citing works
Self-citationLiebert, C. A., Wireman, J., Smith, T., & Summers, A. O. (1997) · Applied and Environmental Microbiology · doi:10.1128/aem.63.3.1066-1076.1997 · Cited by 135 · see citing works
Sutton, D., Butler, A. M., Nadin, L., et al. (1997) · Journal of Pharmacology and Experimental Therapeutics · doi:10.1016/s0022-3565(24)36788-6 · Cited by 134 · see citing works
Tang, J., Zheng, J., Fang, L., Jin, Y., Cai, W., & Li, D. (2015) · British Journal Of Nutrition · doi:10.1017/s0007114515002329 · Cited by 125 · see citing works
Deloménie, C., Fouix, S., Longuemaux, S., Brahimi, N., Bizet, C., Picard, B., Denamur, E., & Dupret, J.-M. (2001) · Journal of Bacteriology · doi:10.1128/jb.183.11.3417-3427.2001 · Cited by 117 · see citing works
Mechanism of cholesterol reduction to coprostanol by Eubacterium coprostanoligenes ATCC 51222
Ren, D., Li, L., Schwabacher, A. W., Young, J. W., & Beitz, D. C. (1996) · Steroids · doi:10.1016/0039-128x(95)00173-n · Cited by 116 · see citing works
Lethal drug interactions of sorivudine, a new antiviral drug, with oral 5-fluorouracil prodrugs.
Okuda, H., Nishiyama, T., Ogura, K., Nagayama, S., Ikeda, K., Yamaguchi, S., Nakamura, Y., KAWAGUCHI, Y., Watabe, T., & Ogura, Y. (1997) · PubMed · Cited by 106 · see citing works
Ulmer, J. E., Vilén, E. M., Namburi, R. B., et al. (2014) · Journal of Biological Chemistry · doi:10.1074/jbc.m114.573303 · Cited by 105 · see citing works
Cooper, A. J. L., Krasnikov, B. F., Niatsetskaya, Z. V., et al. (2010) · Amino Acids · doi:10.1007/s00726-010-0552-0 · Cited by 104 · see citing works
Rafii, F., & Cerniglia, C. E. (1995) · Environmental Health Perspectives · doi:10.1289/ehp.95103s417 · Cited by 104 · see citing works
Textile industry and occupational cancer
Singh, Z., & Chadha, P. (2016) · Journal of Occupational Medicine and Toxicology · doi:10.1186/s12995-016-0128-3 · Cited by 103 · see citing works
Kim, K.-S., Lee, Y., Kim, S. G., et al. (2013) · Chemosphere · doi:10.1016/j.chemosphere.2013.09.066 · Cited by 102 · see citing works
Humblot, C., Murkovic, M., Rigottier-Gois, L., Bensaada, M., Bouclet, A., Andrieux, C., Anba, J., & Rabot, S. (2007) · Carcinogenesis · doi:10.1093/carcin/bgm170 · Cited by 98 · see citing works
Microbial hydrolysis of steviol glycosides
RENWICK, A. G., & Tarka, S. M. (2008) · Food and Chemical Toxicology · doi:10.1016/j.fct.2008.05.008 · Cited by 96 · see citing works
Calne, D. B., Reid, J. L., Vakil, S. D., et al. (1971) · BMJ · doi:10.1136/bmj.3.5777.729 · Cited by 94 · see citing works
On serum-cholesterol levels and neutral fecal sterols in germ-free rats. Bile acids and steroids 59
Danielsson, H., & Gustafsson, B. E. (1959) · Archives of Biochemistry and Biophysics · doi:10.1016/0003-9861(59)90056-6 · Cited by 92 · see citing works
Toxicological aspects of cyclamate and cyclohexylamine
Bopp, B. A., Sonders, R. C., Kesterson, J. W., et al. (1986) · Critical Reviews in Toxicology · doi:10.3109/10408448609037465 · Cited by 92 · see citing works
CONTRIBUTIONS OF HOST AND INTESTINAL MICROFLORA IN THE METABOLISM OF l-DOPA BY THE RAT
Goldin, B. R., Peppercorn, M. A., & Goldman, P. (1973) · Journal of Pharmacology and Experimental Therapeutics · doi:10.1016/s0022-3565(25)29577-5 · Cited by 91 · see citing works
Ticak, T., Kountz, D. J., Girosky, K. E., Krzycki, J. A., & Ferguson, D. J. (2014) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1409642111 · Cited by 88 · see citing works
Laue, H., Friedrich, M., Ruff, J., & Cook, A. M. (2001) · Journal of Bacteriology · doi:10.1128/jb.183.5.1727-1733.2001 · Cited by 87 · see citing works
Role of the gastrointestinal microflora in amygdalin (laetrile)-induced cyanide toxicity
Carter, J. H., McLafferty, M. A., & Goldman, P. (1980) · Biochemical Pharmacology · doi:10.1016/0006-2952(80)90504-3 · Cited by 85 · see citing works
Tozaki, H., Emi, Y., Horisaka, E., Fujita, T., Yamamoto, A., & Muranishi, S. (1997) · Journal of Pharmacy and Pharmacology · doi:10.1111/j.2042-7158.1997.tb06773.x · Cited by 84 · see citing works
Escolá‐Gil, J. C., Llaverı́as, G., Julve, J., et al. (2011) · Arteriosclerosis Thrombosis and Vascular Biology · doi:10.1161/atvbaha.111.236075 · Cited by 79 · see citing works
Xenobiotic Metabolism and Gut Microbiomes
Das, A., Srinivasan, M., Ghosh, T. S., & Mande, S. S. (2016) · PLoS ONE · doi:10.1371/journal.pone.0163099 · Cited by 78 · see citing works
Gérard, P., Béguet, F., Lepercq, P., Rigottier‐Gois, L., Rochet, V., Andrieux, C., & Juste, C. (2004) · FEMS Microbiology Ecology · doi:10.1016/s0168-6496(03)00285-x · Cited by 76 · see citing works
Ryan, A. J., Kaplan, E., Nebel, J., et al. (2014) · PLoS ONE · doi:10.1371/journal.pone.0098551 · Cited by 74 · see citing works
(2016) · Wiley eBooks · doi:10.1002/9781118833322 · Cited by 74 · see citing works
Ellrott, K., Jaroszewski, L., Li, W., Wooley, J., & Godzik, A. (2010) · PLoS Computational Biology · doi:10.1371/journal.pcbi.1000798 · Cited by 73 · see citing works
Molecular Basis of C–N Bond Cleavage by the Glycyl Radical Enzyme Choline Trimethylamine-Lyase
Bodea, S., Funk, M. A., Balskus, E. P., & Drennan, C. L. (2016) · Cell chemical biology · doi:10.1016/j.chembiol.2016.07.020 · Cited by 73 · see citing works
Self-citationCaminero, A., Nistal, E., Herrán, A. R., Pérez-Andrés, J., Ferrero, M. A., Vaquero Ayala, L., Vivas, S., Ruiz de Morales, J. M. G., Albillos, S. M., & Casqueiro, F. J. (2015) · British Journal of Nutrition · doi:10.1017/s0007114515002767 · Cited by 70 · see citing works
The reduction of sulphinpyrazone and sulindac by intestinal bacteria
Strong, H. A., RENWICK, A. G., George, C. F., Liu, Y. F., & Hill, M. J. (1987) · Xenobiotica · doi:10.3109/00498258709043976 · Cited by 70 · see citing works
Kassie, F. (2001) · Carcinogenesis · doi:10.1093/carcin/22.10.1721 · Cited by 70 · see citing works
The role of gut microbiota in fetal methylmercury exposure: Insights from a pilot study
Rothenberg, S. E., Keiser, S., Ajami, N. J., Wong, M. C., Gesell, J. R., Petrosino, J. F., & Johs, A. (2015) · Toxicology Letters · doi:10.1016/j.toxlet.2015.11.022 · Cited by 69 · see citing works
Lifetime toxicity/carcinogenicity studies of FD & C blue No. 1 (Brilliant blue FCF) in rats and mice
Borzelleca, J. F., Depukat, K., & Hallagan, J. B. (1990) · Food and Chemical Toxicology · doi:10.1016/0278-6915(90)90034-k · Cited by 62 · see citing works
Metabolism of Methylmercuric Chloride by the Gastro-Intestinal Flora of the Rat
Rowland, I., DAVIES, M. J., & GRASSO, P. (1978) · Xenobiotica · doi:10.3109/00498257809060381 · Cited by 61 · see citing works
Tyrosine decarboxylase from Lactobacillus brevis: Soluble expression and characterization
Zhang, K., & Ni, Y. (2013) · Protein Expression and Purification · doi:10.1016/j.pep.2013.10.018 · Cited by 61 · see citing works
Stability of peptide drugs in the colon
Wang, J., Yadav, V., Smart, A. L., Tajiri, S., & Basit, A. W. (2015) · European Journal of Pharmaceutical Sciences · doi:10.1016/j.ejps.2015.06.018 · Cited by 59 · see citing works
Lavrijsen, K., Dyck, D. V., Houdt, J. V., Hendrickx, J., Monbaliu, J. G., Woestenborghs, R. J. H., Meuldermans, W., & Heykants, J. (1995) · Drug Metabolism and Disposition · doi:10.1016/s0090-9556(25)06545-6 · Cited by 59 · see citing works
ROSSOL, I., & Pühler, A. (1992) · Journal of Bacteriology · doi:10.1128/jb.174.9.2968-2977.1992 · Cited by 47 · see citing works
Diaz-Bone, R. A., & de Wiele, T. R. V. (2009) · Environmental Science & Technology · doi:10.1021/es900544c · Cited by 45 · see citing works
Discovery of a sesamin-metabolizing microorganism and a new enzyme
Kumano, T., Fujiki, E., Hashimoto, Y., et al. (2016) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1605050113 · Cited by 45 · see citing works
Emerging Aspects of Food and Nutrition on Gut Microbiota
He, X. M., Marco, M. L., & Slupsky, C. M. (2013) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf4029046 · Cited by 43 · see citing works
van Hogezand, R. A., Kennis, H. M., van Schaik, A., Koopman, J. P., van Hees, P. A. M., & van Tongeren, J. H. M. (1992) · European Journal of Clinical Pharmacology · doi:10.1007/bf01740669 · Cited by 40 · see citing works
Mechanism-Based Inhibitors of Glycosidases
Kallemeijn, W. W., Witte, M. D., Wennekes, T., et al. (2014) · Advances in carbohydrate chemistry and biochemistry · doi:10.1016/b978-0-12-800128-8.00004-2 · Cited by 34 · see citing works
Intestinal first pass metabolism of amygdalin in the rat in vitro
Strugala, G. J., Rauws, A. G., & Elbers, R. (1986) · Biochemical Pharmacology · doi:10.1016/0006-2952(86)90580-0 · Cited by 31 · see citing works
Comparative Developmental Toxicity and Metabolism of Nitrazepam in Rats and Mice
Takeno, S., Hirano, Y., Kitamura, A., et al. (1993) · Toxicology and Applied Pharmacology · doi:10.1006/taap.1993.1150 · Cited by 30 · see citing works
Bos, R. P., van der Krieken, W., Smeijsters, L. J., et al. (1986) · Toxicology · doi:10.1016/0300-483x(86)90080-6 · Cited by 27 · see citing works
Relman, A. S. (1982) · New England Journal of Medicine · doi:10.1056/nejm198201283060410 · Cited by 27 · see citing works
Rafii, F., & Cerniglia, C. E. (1995) · Environmental Health Perspectives · doi:10.2307/3432471 · Cited by 27 · see citing works
THE EFFECT OF DIETARY XYLITOL ON THE ABILITY OF RAT CAECAL FLORA TO METABOLISE XYLITOL
Krishnan, R., Wilkinson, I. J., Joyce, L., et al. (1980) · Immunology and Cell Biology · doi:10.1038/icb.1980.66 · Cited by 26 · see citing works
Partial Purification and Some Properties of Cyclamate Sulfamatase*
Niimura, T., TOKIEDA, T., & Yamaha, T. (1974) · The Journal of Biochemistry · doi:10.1093/oxfordjournals.jbchem.a130407 · Cited by 24 · see citing works
Decarboxylation of orally administered l-dopa in the human digestive tract
Bergmark, J., Carlsson, A., Granérus, A., JAGENBURG, R., Magnusson, T., & Svanborg, A. (1972) · Naunyn-Schmiedeberg s Archives of Pharmacology · doi:10.1007/bf00501249 · Cited by 23 · see citing works
Wang, H., Geng, C., Li, J., et al. (2013) · Applied Microbiology and Biotechnology · doi:10.1007/s00253-013-5363-2 · Cited by 18 · see citing works
Sulphoxide reduction by rat intestinal flora and by Escherichia coli in vitro
Lee, S. C., & Renwick, A. G. C. (1995) · Biochemical Pharmacology · doi:10.1016/0006-2952(95)00093-f · Cited by 18 · see citing works
Rowland, I. R., Davies, M. J., & Jg, E. (1980) · PubMed · Cited by 12 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
The gut-liver axis and the intersection with the microbiome
Tripathi, A., Debelius, J., Brenner, D. A., Karin, M., Loomba, R., Schnabl, B., & Knight, R. (2018) · Nature Reviews Gastroenterology & Hepatology · doi:10.1038/s41575-018-0011-z · Cited by 1,480 · see citing works
Dietary metabolism, the gut microbiome, and heart failure
Tang, W. H. W., Li, D. Y., & Hazen, S. L. (2019) · Nature Reviews Cardiology · doi:10.1038/s41569-018-0108-7 · Cited by 789 · see citing works
A metabolic pathway for bile acid dehydroxylation by the gut microbiome
Funabashi, M., Grove, T. L., Wang, M., Varma, Y., McFadden, M. E., Brown, L. C., Guo, C., Higginbottom, S., Almo, S. C., & Fischbach, M. A. (2020) · Nature · doi:10.1038/s41586-020-2396-4 · Cited by 590 · see citing works
Gut microbiota-mediated inflammation in obesity: a link with gastrointestinal cancer
Cani, P. D., & Jordan, B. F. (2018) · Nature Reviews Gastroenterology & Hepatology · doi:10.1038/s41575-018-0025-6 · Cited by 383 · see citing works
Gut microbial molecules in behavioural and neurodegenerative conditions
Needham, B. D., Kaddurah-Daouk, R., & Mazmanian, S. K. (2020) · Nature Reviews Neuroscience · doi:10.1038/s41583-020-00381-0 · Cited by 379 · see citing works
Gut reactions: Breaking down xenobiotic–microbiome interactions
Clarke, G., Sandhu, K. V., Griffin, B. T., Dinan, T. G., Cryan, J. F., & Hyland, N. P. (2019) · Pharmacological Reviews · doi:10.1124/pr.118.015768 · Cited by 319 · see citing works
Leveraging diet to engineer the gut microbiome
Wolter, M., Grant, E. T., Boudaud, M., Steimle, A., Pereira, G. V., Martens, E. C., & Desai, M. S. (2021) · Nature Reviews Gastroenterology & Hepatology · doi:10.1038/s41575-021-00512-7 · Cited by 211 · see citing works
Epigenetic Regulation at the Interplay Between Gut Microbiota and Host Metabolism
Miro-Blanch, J., & Yanes, O. (2019) · Frontiers in Genetics · doi:10.3389/fgene.2019.00638 · Cited by 195 · see citing works
Sharpton, S. R., Schnabl, B., Knight, R., & Loomba, R. (2021) · Cell Metabolism · doi:10.1016/j.cmet.2020.11.010 · Cited by 194 · see citing works
Microbiota and cancer immunotherapy: in search of microbial signals
Gharaibeh, R. Z., & Jobin, C. (2019) · Gut · doi:10.1136/gutjnl-2018-317220 · Cited by 144 · see citing works
Precision medicine using microbiota
Jobin, C. (2018) · Science · doi:10.1126/science.aar2946 · Cited by 133 · see citing works
Dashnyam, P., Mudududdla, R., Hsieh, T.-J., Lin, T.-C., Lin, H.-Y., Chen, P.-Y., Hsu, C.-Y., & Lin, C.-H. (2018) · Scientific Reports · doi:10.1038/s41598-018-34678-z · Cited by 108 · see citing works
The emerging roles of bacterial proteases in intestinal diseases
Caminero, A., Guzman, M., Libertucci, J., & Lomax, A. E. (2023) · Gut Microbes · doi:10.1080/19490976.2023.2181922 · Cited by 92 · see citing works
Engineering microphysiological immune system responses on chips
Miller, C. P., Shin, W., Ahn, E. H., Kim, H. J., & Kim, D.-H. (2020) · Trends in biotechnology · doi:10.1016/j.tibtech.2020.01.003 · Cited by 74 · see citing works
A data-driven approach for predicting the impact of drugs on the human microbiome
Algavi, Y. M., & Borenstein, E. (2023) · Nature Communications · doi:10.1038/s41467-023-39264-0 · Cited by 54 · see citing works
Tyagi, P., Tasleem, M., Prakash, S., & Chouhan, G. (2020) · Food Research International · doi:10.1016/j.foodres.2020.109489 · Cited by 42 · see citing works
Wang, Y., Tan, W., Li, X., Yang, G., Wang, Y., Liao, J., Lu, A., Zhang, G., Chen, K., Yang, L., et al. (2025) · Frontiers in Cellular and Infection Microbiology · doi:10.3389/fcimb.2025.1455735 · Cited by 2 · see citing works
- Authors
- Koppel, N., Maini Rekdal, V., & Balskus, E. P.
- Affiliations
- Harvard University (US)
- Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02138, USA.
- Broad Institute (US)
- Corresponding author
- Balskus, Emily P.
- Venue
- Science
- Published
- 2017-06-23
- Volume
- 356
- Issue
- 6344
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- PMC
- PMC5534341
- OpenAlex
- W2716699759
- Cited by
- 1,080
- References
- 129
- Citations by year
- 2026: 115 · 2025: 149 · 2024: 130 · 2023: 128 · 2022: 139 · 2021: 123 · 2020: 118 · 2019: 85 · 2018: 75 · 2017: 18
- FWCI
- 7.52
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Locations
- Science (publishedVersion)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- Funders
- National Science Foundation (award311960, MCB-1650086, award311961, DGE1144152)
- National Institutes of Health (award311959, CA208834, award311962, 5T32GM007598)
- David and Lucile Packard Foundation (award311955, Packard Fellowship for Science and Engineering)
- Defense Advanced Research Projects Agency (award311958, HR0011-16-2-0013)
- Bill and Melinda Gates Foundation (award312457)
- Richard and Susan Smith Family Foundation (award311953, Smith Family Award for Excellence in Biomedical Research)
- Takeda Pharmaceutical Company (award311957)
- George W. Merck Fellowship (award311954, N/A)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Gut microbiota and health
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Pharmacogenetics and Drug Metabolism
- Health Sciences › Medicine › Oncology › Drug Transport and Resistance Mechanisms
- Keywords
- gut microbiota, xenobiotic metabolism, microbial transformation, dietary compounds, pharmaceuticals, industrial chemicals, microbial enzymes, personalized medicine, drug discovery
- MeSH terms
- Gastrointestinal Microbiome, Bacteria, Pharmaceutical Preparations, Environmental Pollutants, Food, Humans, Research, Xenobiotics
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
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