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Open AccessArticle

Biotransformation of Silymarin Flavonolignans by Human Fecal Microbiota

Laboratory of Biotransformation, Institute of Microbiology of the Czech Academy of Sciences, Vídeňská 1083, 14220 Prague, Czech Republic
Department of Food Science, Czech University of Life Sciences Prague, Kamýcká 129, 16500 Prague, Czech Republic
Department of Medical Chemistry and Biochemistry, Faculty of Medicine and Dentistry, Palacký University, Hněvotínská 3, 77515 Olomouc, Czech Republic
Regional Centre of Advanced Technologies and Materials, Department of Analytical Chemistry, Faculty of Science, Palacký University, 17. listopadu 12, 77146 Olomouc, Czech Republic
Department of Biochemistry and Microbiology, University of Chemistry and Technology Prague, Technická 5, CZ 16628 Prague, Czech Republic
Author to whom correspondence should be addressed.
Metabolites 2020, 10(1), 29;
Received: 1 December 2019 / Revised: 4 January 2020 / Accepted: 7 January 2020 / Published: 9 January 2020
(This article belongs to the Special Issue Gut Metabolism of Natural Products)
Flavonolignans occur typically in Silybum marianum (milk thistle) fruit extract, silymarin, which contains silybin, isosilybin, silychristin, silydianin, and their 2,3-dehydroderivatives, together with other minor flavonoids and a polymeric phenolic fraction. Biotransformation of individual silymarin components by human microbiota was studied ex vivo, using batch incubations inoculated by fecal slurry. Samples at selected time points were analyzed by ultrahigh-performance liquid chromatography equipped with mass spectrometry. The initial experiment using a concentration of 200 mg/L showed that flavonolignans are resistant to the metabolic action of intestinal microbiota. At the lower concentration of 10 mg/L, biotransformation of flavonolignans was much slower than that of taxifolin, which was completely degraded after 16 h. While silybin, isosilybin, and 2,3-dehydrosilybin underwent mostly demethylation, silychristin was predominantly reduced. Silydianin, 2,3-dehydrosilychristin and 2,3-dehydrosilydianin were reduced, as well, and decarbonylation and cysteine conjugation proceeded. No low-molecular-weight phenolic metabolites were detected for any of the compounds tested. Strong inter-individual differences in the biotransformation profile were observed among the four fecal-material donors. In conclusion, the flavonolignans, especially at higher (pharmacological) doses, are relatively resistant to biotransformation by gut microbiota, which, however, depends strongly on the individual structures of these isomeric compounds, but also on the stool donor. View Full-Text
Keywords: silymarin; flavonolignans; biotransformation; metabolites; gut microbiota; UHPLC–MS; inter-individual differences silymarin; flavonolignans; biotransformation; metabolites; gut microbiota; UHPLC–MS; inter-individual differences
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Valentová, K.; Havlík, J.; Kosina, P.; Papoušková, B.; Jaimes, J.D.; Káňová, K.; Petrásková, L.; Ulrichová, J.; Křen, V. Biotransformation of Silymarin Flavonolignans by Human Fecal Microbiota. Metabolites 2020, 10, 29.

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