Malvidin 3-Glucoside–Fatty Acid Conjugates: From Hydrophilic toward Novel Lipophilic Derivatives

Abstract

This work describes the lipophilization reactions of malvidin 3-glucoside with different saturated fatty acid chain lengths using an enzymatic synthesis and the study of their physical-chemical and antioxidant properties. The lipophilic anthocyanins were obtained with satisfactory yields (22-40%) after column chromatography purifications, and they revealed the same appealing chromatic features of the parent anthocyanin. All of the compounds were characterized by mass spectrometry, confirming the regioselective acylation on the glucose moiety. The octanol-water partition coefficients and the hydrophobicity index of the different derivatives were determined, confirming a lipophilicity increase concomitant with the fatty acid chain length. The antioxidant profile was also evaluated by using two in vitro methods (β-carotene-lineolate method and oxygen consumption assay). Overall, a maximum of antioxidant activity was achieved when malvidin 3-glucoside was conjugated with caprylic acid (C8). Altogether, the results obtained provide a good perspective for the technological application of these functionalized anthocyanins in the cosmetics and food industries.

Selective enzymatic lipophilization of anthocyanin glucosides from blackcurrant (Ribes nigrum L.) skin extract and characterization of esterified anthocyanins

“…The reactions started with the addition of the CalB enzyme (20 g L 1 ). The reactions were stirred at 60 ºC over a 9 h period and their progression was followed by HPLC-DAD, as demonstrated in earlier research (Cruz et al, 2017). At the maximum products formation, the reaction was filtered to remove the molecular sieves, CalB and the solvent was evaporated under vacuum.…”

“…The more lipophilic derivative did not show any reduction in antioxidant potential and protected more effectively a lipidic substrate from oxidation. Enzymatic catalysis using CalB in reactions between pure Mv3glc and different fatty acids (C 4 , C 6 , C 8 , C 10 , C 12 , C 14 , C 16 ) gives yields of acylated ANC of 22 40%, which could be separated by column chromatography (Cruz et al, 2017). All acylated ANCs with fatty acid chain length C8 and above showed particularly enhanced lipophilicity and preferentially partitioned into octanol in an octanolwater biphasic system.…”

Effects of magnetic fields on the enzymatic synthesis of naringin palmitate

“…Acylation with non-magnetized I-CALB and non-magnetized I-CALB solution was performed as the control. The concentrations of naringin and naringin palmitate were measured using HPLC as described by Zhang et al 3,10 All the experiments were performed in triplicate.…”

“…7 Some naringin esters such as naringin lauroyl ester, naringin octanoic acid ester, naringin decanoic acid ester and naringin palmitate have previously been synthesized through lipase-catalyzed acylation in organic solvents. 3,[8][9][10] However, the practical application of enzymatic methods is limited by low conversion yield. 11,12 An external eld such as a magnetic eld may be used to improve enzymatic naringin derivatization in organic solvents.…”

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

“…[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.…”