Deglycosylation of Two Typical Plant-Generated Glycoconjugates of Tetrabromobisphenol A through In Vitro Digestion Processes

Abstract

Tetrabromobisphenol A (TBBPA) is extensively detected in various environmental media. Its typical glycosylation products in plants, TBBPA mono-β-D-glucopyranoside (TBBPA MG) and TBBPA di-β-D-glucopyranoside (TBBPA DG), are likely to enter the human body through the oral route. The deglycosylation processes of TBBPA MG and TBBPA DG in both simulated gastric fluid (SGF) and simulated intestinal fluid (SIF) were studied. Results showed that 68% of TBBPA MG was transformed to TBBPA after 6 h incubation in gastrointestinal fluid, about 31% and 7% of TBBPA DG were transformed to TBBPA MG and TBBPA, respectively. In SGF, strong acid hydrolysis mainly contributed to the deglycosylation of TBBPA MG and TBBPA DG. In SIF, the bacteria, the synergistic effect of bacteria and pancreatin, and the bile led to the deglycosylation of TBBPA MG and TBBPA DG. The results indicated glycosylation products of TBBPA formed in vegetables or crops will be partially transformed into TBBPA and partially retained in the forms of glycosylation products in the human digestion system and may enter into the circulation system. These TBBPA glycoconjugates and the released TBBPA will cause health risks. This finding improved our understanding on the environmental fates, exposures, and health risks of TBBPA and its important phytometabolites.

α-Glucosidase Inhibitors from Cold-Pressed Black Sesame (Sesamum indicum) Meal: Characterization of New Furofuran Lignans, Kinetic Study, and In Vitro Gastrointestinal Digestion

“…One possible explanation for these structures was the action of pancreatin from the pancreas, which could catalyze deglycosylation and demethylation processes. 43,44 In our investigation, we observed significant levels of metabolized STG during small intestinal digestion, aligning with earlier studies that indicate the presence of STG in the digestive pathway and its efficient metabolism by microorganisms in the excretory tract. 35,36,42,45 In summary, this study presents the first comprehensive investigation of α-glucosidase inhibitors isolated from black sesame meal using bioassay-guided isolation.…”

“…The detection of the [M + H] + ion at 685.43671 indicated the removal of one glucose and two methylene groups, resulting in the proposed structures of SIF-1 (Figure ). One possible explanation for these structures was the action of pancreatin from the pancreas, which could catalyze deglycosylation and demethylation processes. , In our investigation, we observed significant levels of metabolized STG during small intestinal digestion, aligning with earlier studies that indicate the presence of STG in the digestive pathway and its efficient metabolism by microorganisms in the excretory tract. ,,, …”

Phloem Redistribution of Pesticide Phenamacril in Plants Followed by Extensive Biotransformation

“…Conjugation reactions are usually reversible, and deconjugation has been proved in human digestive systems. 52,53 Specifically, phase-II conjugation product M-392 might be deconjugated to phenamacril in human gut after intake. Furthermore, metabolite like M-157 was estimated to be more toxic and persistence than phenamacril.…”

“…This study demonstrated that phloem translocation and plant excretion were important pathways to transport phenamacril from shoots to roots and rhizosphere environments, resulting in a prolonged cycling contamination, which should be considered in developing more accurate prediction models for assessing the risks of phloem-transported chemicals to ecosystems. − After being taken up, phenamacril was extensively transformed (e.g., 76.4%) in plants, with nine metabolites newly identified. Conjugation reactions are usually reversible, and deconjugation has been proved in human digestive systems. , Specifically, phase-II conjugation product M-392 might be deconjugated to phenamacril in human gut after intake. Furthermore, metabolite like M-157 was estimated to be more toxic and persistence than phenamacril.…”

Angiogenic Activity and Mechanism for Bisphenols on Endothelial Cell and Mouse: Evidence of a Structural-Selective Effect

“…14 Our previous studies found that BPA with different halogenation patterns distinctly affects the activities toward the peroxisome proliferator-activated receptor and estrogen receptor (ER). 15 Brominated bisphenols including tetrabromobisphenol A (TBBPA) and TBBPS, the mostly used bisphenols as flame retardants in plastics, textiles, and electronic equipment, 16 T h i s c o n t e n t i s showed stronger thyroid disruption than BPA and BPS. Structural moiety differences of bisphenols are suspected to affect a variety of physiological signaling, responsible for subsequent biological defects.…”