Divergent metabolism of two lychee (Litchi chinensis Sonn.) pulp flavonols and their modulatory effects on gut microbiota: Discovery of hydroxyethylation in vitro colonic fermentation

Quercetin 3-O-rutinose-7-O-α-l-rhamnoside (QRR), a characteristic lychee pulp flavonoid, has been linked to diverse bioactivities involving microbial metabolism. By integrating colonic fermentation and mass spectrometry, the catabolites including 7-O-hydroxyethyl-isorhamnetin and 3'-amino-4'-O-methyl-7-O-hydroxyethyl-isorhamnetin were unprecedently identified and unique to QRR metabolism, relative to the structural analog quercetin 3-O-rutinoside (QR) metabolism. These above-described metabolites highlighted a special biotransformation hydroxyethylation in QRR catabolism. QRR was partially deglycosylated into quercetin 3-O-glucoside-7-O-α-l-rhamnoside potentially catalyzed by Bacteroides. QR was more directly degradable to aglycone during colonic fermentation than are QRR. Unlike with QR fermentation, equivalent QRR effectively upregulated concentrations of propionic and butyric acids that were highly relevant with Faecalibacterium and Coprococcus. After fermentation, the relative abundances of Bacteroides uniformis (0.03%) and Akkermansia muciniphila (0.13%) were only upregulated by QRR among all fermentation groups, leading to the enrichments of the corresponding genera. These results further reveal the relationship between flavonoid structures and metabolic characteristics.