Synthesis of hydroxycinnamic acid glucuronides and investigation of their affinity for human serum albumin

Abstract

Hydroxycinnamic acids (HCAs) are among the most abundant dietary polyphenols. Recent bioavailability studies have shown that HCAs enter the blood circulation mainly as glucuronides, which are thus most likely to express their potential health effects. In this work, an efficient synthesis of HCA O-arylglucuronides is developed. As for many xenobiotics, the resilience of HCA O-arylglucuronides in plasma and subsequent delivery to tissues could be governed by their binding to human serum albumin (HSA). Hence, the affinity of HCA O-arylglucuronides for HSA and its possible binding site were investigated by fluorescence spectroscopy. HCA O-arylglucuronides turn out to be moderate HSA ligands (K in the range 1–4 × 10⁴ M⁻¹) that bind HSA in sub-domain IIA, competitively or noncompetitively with other sub-domain IIA ligands such as dansylamide and the flavonol quercetin.