Demethylation of Polymethoxyflavones by Human Gut Bacterium, Blautia sp. MRG-PMF1
| Autor: | Supawadee Burapan, Mihyang Kim, Jaehong Han |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
0301 basic medicine
Flavonoid Firmicutes 01 natural sciences Methylation 03 medical and health sciences chemistry.chemical_compound Humans Chrysin Biotransformation Demethylation chemistry.chemical_classification Flavonoids 010401 analytical chemistry General Chemistry 0104 chemical sciences Gastrointestinal Microbiome Galangin Intestines 030104 developmental biology chemistry Biochemistry Apigenin General Agricultural and Biological Sciences Kaempferol Quercetin Luteolin |
| Zdroj: | Journal of agricultural and food chemistry. 65(8) |
| ISSN: | 1520-5118 |
| Popis: | Polymethoxyflavones (PMFs) were biotransformed to various demethylated metabolites in the human intestine by the PMF-metabolizing bacterium, Blautia sp. MRG-PMF1. Because the newly formed metabolites can have different biological activities, the pathways and regioselectivity of PMF bioconversion were investigated. Using an anaerobic in vitro study, 12 PMFs, 5,7-dimethoxyflavone (5,7-DMF), 5-hydroxy-7-methoxyflavone (5-OH-7-MF), 3,5,7-trimethoxyflavone (3,5,7-TMF), 5-hydroxy-3,7-dimethoxyflavone (5-OH-3,7-DMF), 5,7,4'-trimethoxyflavone (5,7,4'-TMF), 5-hydroxy-7,4'-dimethoxyflavone (5-OH-7,4'-DMF), 3,5,7,4'-tetramethoxyflavone (3,5,7,4'-TMF), 5-hydroxy-3,7,4'-trimethoxyflavone (5-OH-3,7,4'-TMF), 5,7,3',4'-tetramethoxyflavone (5,7,3',4'-TMF), 3,5,7,3',4'-pentamethoxyflavone (3,5,7,3',4'-PMF), 5-hydroxy-3,7,3',4'-tetramethoxyflavone (5-OH-3,7,3',4'-TMF), and 5,3'-dihydroxy-3,7,4'-trimethoxyflavone (5,3'-diOH-3,7,4'-TMF), were converted to chrysin, apigenin, galangin, kaempferol, luteolin, and quercetin after complete demethylation. The time-course monitoring of PMF biotransformations elucidated bioconversion pathways, including the identification of metabolic intermediates. As a robust flavonoid demethylase, regioselectivity of PMF demethylation generally followed the order C-7C-4' ≈ C-3'C-5C-3. PMF demethylase in the MRG-PMF1 strain was suggested as a Co-corrinoid methyltransferase system, and this was supported by the experiments utilizing other methyl aryl ether substrates and inhibitors. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|