Phosphorylation of Isoflavones by Bacillus subtilis BCRC 80517 May Represent Xenobiotic Metabolism
Journal
Journal of Agricultural and Food Chemistry
Journal Volume
66
Journal Volume
66
Journal Issue
1
Journal Issue
1
Pages
127-137
Start Page
127
End Page
137
ISSN
00218561
Date Issued
2018-01-10
Author(s)
Abstract
The soy isoflavones daidzein (DAI) and genistein (GEN) have beneficial effects on human health. However, their oral bioavailability is hampered by their low aqueous solubility. Our previous study revealed two water-soluble phosphorylated conjugates of isoflavones, daidzein 7-O-phosphate and genistein 7-O-phosphate, generated via biotransformation by Bacillus subtilis BCRC80517 cultivated with isoflavones. In this study, two novel derivatives of isoflavones, daidzein 4′-O-phosphate and genistein 4′-O-phosphate, were identified by HPLC-ESI-MS/MS and 1H, 13C, and 31P NMR, and their biotransformation roadmaps were proposed. Primarily, isoflavone glucosides were deglycosylated and then phosphorylated predominantly into 7-O-phosphate conjugates with traces of 4′-O-phosphate conjugates. Inevitably, trace quantities of glucosides were converted into 6″-O-succinyl glucosides. GEN was more efficiently phosphorylated than DAI. Nevertheless, the presence of GEN prolonged the time until the exponential phase of cell growth, whereas the other isoflavones showed little effect on cell growth. Our findings provide new insights into the novel microbial phosphorylation of isoflavones involved in xenobiotic metabolism.
Subjects
Bacillus subtilis
biotransformation
isoflavone
phosphorylation
xenobiotic metabolism
Other Subjects
Bacteriology; Biochemistry; Bioconversion; Carbohydrates; Cell growth; Growth kinetics; Metabolism; Phosphorylation; Physiology; Aqueous solubility; Bacillus Subtilis; Beneficial effects; biotransformation; Exponential phase; Isoflavones; Oral bioavailabilities; Xenobiotic metabolism; Flavonoids; isoflavone derivative; xenobiotic agent; Bacillus subtilis; biotransformation; drug effects; electrospray mass spectrometry; growth, development and aging; high performance liquid chromatography; isolation and purification; metabolism; nuclear magnetic resonance spectroscopy; phosphorylation; Bacillus subtilis; Biotransformation; Chromatography, High Pressure Liquid; Isoflavones; Magnetic Resonance Spectroscopy; Phosphorylation; Spectrometry, Mass, Electrospray Ionization; Xenobiotics
Publisher
American Chemical Society
Type
journal article