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SHR Neuro Cancer Cardio Lipid Metab Microb

Pferschy-Wenzig, EM; Kunert, O; Thumann, T; Moissl-Eichinger, C; Bauer, R.
Characterization of metabolites from milk thistle flavonolignans generated by human fecal microbiota.
Phytochemistry. 2023; 215: 113834 Doi: 10.1016/j.phytochem.2023.113834
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Co-authors Med Uni Graz

Moissl-Eichinger Christine

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Abstract:

Silymarin, a mixture of diastereomeric and regioisomeric flavonolignans from milk thistle (Silybum marianum (L.) Gaertn.) fruits, is known to possess a panel of pharmacological activities. However, due to low water solubility and extensive phase II metabolism, the oral bioavailability of the flavonolignans is limited. Since their interaction with gut microbiome is likely due to their predominantly fecal excretion route, the biotransformation of milk thistle flavonolignans by gut microorganisms was studied. A 1:1 mixture of the two main silymarin flavonolignans silybins A and B was incubated in human fecal suspension from one donor for 24 h under anoxic conditions. Purification of the incubate allowed to isolate and structurally elucidate the two main metabolites as (2R, 3R)-2-{4-[2-(3,4-dihydroxy-phenyl)-(1R)-1-hydroxymethyl-ethoxy]-3-hydroxy-phenyl}-3,5,7-trihydroxy-chroman-4-one (a product of demethylation and dioxane ring cleavage) and demethylsilybin B. Furthermore, silymarin was incubated with human fecal suspension, and its biotransformation was monitored by means of LC-HRMS metabolite profiling. Apart from the two isolated and structurally elucidated metabolites, several types of biotransformation products could be annotated, including demethylation products, reduction/ring cleavage products, products of demethylation plus reduction/ring cleavage, as well as several low molecular weight aromatic metabolites. The potential pharmacological activities of these gut microbial metabolites deserve closer examination in the future.

Find related publications in this database (using NLM MeSH Indexing)

Humans - administration & dosage

Milk Thistle - administration & dosage

Silymarin - pharmacology

Fruit - administration & dosage

Microbiota - administration & dosage

Find related publications in this database (Keywords)

Silybum marianum

Asteraceae

Milk thistle

Flavonolignan

Gut microbiome

Biotransformation

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