Structural aspects of acylated plant pigments: stabilization of flavonoid glucosides and interpretation of their functions

Effect of acyl donor chain length on isoquercitrin acylation and biological activities of corresponding esters

“…However, chemical processes are not regioselective: they lead to the functionalization of phenolic groups, and thus possibly decrease their antioxidant activity [22,23,16]. The enzymatic acylation was shown to be more regioselective and to enhance not only flavonoids solubility in various media, but also their stability and their antioxidant activity [24][25][26]. In addition, flavonoid derivatives are expected to exhibit a higher affinity for phospholipidic membranes and could be useful to establish structure-activity relationships relating their amphiphilic and lipophilic properties to their ability to be transferred into cells.…”

“…However, in some cases, the formation of di-and tri-acylated isoquercitrin has been reported [47]. Ishihara and Nakajima [25] showed that the enzymatic synthesis of acylated isoquercitrin was accomplished by a lipasecatalyzed transesterification with carboxylic acid vinyl esters as acyl donors in acetone or acetonitrile as solvent. These authors found that acylation occurred on the primary OH of the sugar moiety and indicated that the introduction of an acyl group onto isoquercitrin structure improved its thermostability and light-stability.…”

Direct Acylation of Cyanidin-3-Glucoside with Lauric Acid in Blueberry and Its Stability Analysis

“…Acylated modification of glucoside can retain the main activity and improve lipotropism, thereby promoting fat and lipid metabolism. A previous study showed that acylated anthocyanins are more stable than unacylated anthocyanins [25] . To improve anthocyanin stability and solubility in oils and to broaden its future application in the food industry, using a chemical method to acylate anthocyanins is an optimal choice.…”

“…Thus, anthocyanins are both hydrophilic and hydrophobic. Given the many hydroxyls in flavonoid compounds, many anthocyanins have low lipotropism [25][26][27] .…”

Glycoside Hydrolases for Extraction and Modification of Polyphenolic Antioxidants

“…Problems with many flavonoids are, however, low solubility and poor stability (in both polar and non-polar media) which makes their uses difficult in many formulations of food, pharmaceutical and nutraceutical products (Ishihara and Nakajima 2003). Improvement of the hydrophilic nature, biological properties and stability of flavonoids can be achieved by enzymatic structural modification (Haddad et al 2005).…”