Structures of berberine and its metabolites. (1) Berberine; (2) berberrubine; (3) thalifendine; (4) demethyleneberberine; (5) jathorrhizine; (6) columbamine; (7) palmatine; (8) 3,9-demethylpalmatine; (9) 3,10-demethylpalmatine; (10) 2,3,9-trihydroxiberberine; (11) 2,3,10-trihydroxiberberine; (12) berberrubine-9-O-β-D-glucuronide; (13) thalifendine-10-O-β-D-glucuronide; (14) demethyleneberberine-2,3-di-O-β-D-glucuronide; (15) jatrorrhizine-3-O-β-D-glucuronide; (16) columbamine-3-O-β-D-glucuronide; (17) demethyleneberberine-2-O-sulfate; (18) thalifendine-10-O-sulfate; (19) jatrorrhizine-3-O-sulfate; (20) 3,10-demethylpalmatine-10-O-sulfate; (21) 2,3,10-trihydroxyberberine-2-O-sulfate; (22) glucuronide of demethyleneberberine; (23) glucuronide of 3,9-demethylpalmatine; (24) hydroxylated berberine; (25) dihydroberberine [40].