Demethylation of Polymethoxyflavones by Human Gut Bacterium, Blautia sp MRG-PMF1
- Authors
- Burapan, Supawadee; Kim, Mihyang; Han, Jaehong
- Issue Date
- Mar-2017
- Publisher
- AMER CHEMICAL SOC
- Keywords
- biotransformation; Blautia; Co-corrinoid; flavonoid; human intestinal bacteria; polymethoxyflavone; regioselectivity
- Citation
- JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, v.65, no.8, pp 1620 - 1629
- Pages
- 10
- Journal Title
- JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
- Volume
- 65
- Number
- 8
- Start Page
- 1620
- End Page
- 1629
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/4697
- DOI
- 10.1021/acsofc7b00408
- ISSN
- 0021-8561
1520-5118
- Abstract
- 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-hydroxy3,7-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 (5OH-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 biotransformation elucidated bioconversion pathways, including the identification of metabolic intermediates. As a robust flavonoid demethylase, regioselectivity of PMF demethylation generally followed the order C-7 > C-4' approximate to C-3' > C-5 > C-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.
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