Improvement of the Color Stability of Cyanidin-3-glucoside by Fatty Acid Enzymatic Acylation

Abstract

Anthocyanins are water-soluble pigments with limited application in lipophilic matrices such as lipid-based foods and cosmetic formulations. In this work, the liposolubility improvement of cyanidin-3-glucoside (cy3glc) was performed by enzymatic esterification with saturated fatty acids with variable chain lengths, and their thermostabilities were evaluated at different pH values in a lipophilic medium (an aqueous sodium dodecyl sulfate solution) by means of UV-vis spectroscopy. Overall, lipophilic cy3glc derivatives showed improved color stability and lowered sensitivity to thermal degradation than nonmodified cy3glc in an SDS micellar solution between pH 3 and 7.

Impact of a Water‐Soluble Gallic Acid‐Based Dendrimer on the Color‐Stabilizing Mechanisms of Anthocyanins

“…cv., Touriga Nacional) and from blackberries ( Rubus fruticosus L.), respectively. All the purification procedures were followed as described elsewhere . The purity of the pigments was assessed by HPLC‐DAD and 1 H NMR spectroscopy.…”

“…[13] Other strategies for color stabilization of anthocyanins found in plants is to make acylated derivatives, which are usually used as food colorants because of their superior stabilityo vern on-acylated anthocyanins. [14,15,32,54] Supramolecular host-guest interactions have been widely applied in chemicala nd biochemical fields. Host-guest systems are formed by molecular recognition of ar eceptor (host) and a ligand (guest) by means of noncovalent interactions, such as electrostatic, hydrogen bonds, hydrophobic interactions,chemical coordination, van der Waals forces, and p-p stacking.…”

“…However, owing to the co‐pigmentation phenomena with other flavonoids and self‐association mechanism, the stabilization of the flavylium form of anthocyanins occurs . Other strategies for color stabilization of anthocyanins found in plants is to make acylated derivatives, which are usually used as food colorants because of their superior stability over non‐acylated anthocyanins . Supramolecular host–guest interactions have been widely applied in chemical and biochemical fields.…”

Kinetics of Enzymatic Synthesis of Cyanidin-3-Glucoside Lauryl Ester and Its Physicochemical Property and Proliferative Effect on Intestinal Probiotics

“…Various methods, such as acylation [ 13 ], microencapsulation [ 14 ], and adding auxiliary compounds [ 15 , 16 ], have been attempted to increase the stability of anthocyanins in past decades. Therefore, chemical and enzymatic acylation have made substantial progress in improving the liposolubility and stability of anthocyanins in recent years [ 17 , 18 , 19 , 20 , 21 , 22 , 23 ]. Procyanidin B4 and malvidin-3-glucoside stearic acid derivatives were synthesized and characterized [ 17 ], and cyanidin-3-glucoside from blueberry was chemically acylated with lauric acid in vitro to produce Cy3glc-C12, in which the reaction (acylation rate: 30.78%) was continuously stirred for 48 h at 4 °C in DMF with Cy3glc (20 mg) and acyl donors, including lauric acid (1 equiv), 1-(3-dimethylaminopropy)-3-ethycarbodiimide (1.5 equiv) and N-hydroxybenzotriazole (1 equiv) [ 18 ].…”

“…Although the conversion yield was high, pyridine, as a toxic solvent, could affect the safety of acylated products. To compensate for the solvent toxicity of pyridine, tert-butanol, tert-amyl alcohol, and acetonitrile with high hydrophobicity were used in direct esterification, such as malvidin-3-glucoside (yields: 22–40%) [ 21 , 22 ] and cyanidin-3-glucoside with different saturated fatty acids (yields: 25–47%) [ 23 ]. In the direct esterification, saturated fatty acids with different carbon chains were chosen as the acyl donors from liquid acid to solid acid.…”