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

Abstract

dong Sun (2015): Direct acylation of cyanidin-3-glucoside with lauric acid in blueberry and its stability analysis, International Journal of Food Properties, ABSTRACTCyanidin-3-glucoside (C3G) is an anthocyanin that is abundant in blueberry. Lauric acid was used as the acyl donor in the acylation of C3G. Preparative high performance liquid chromatography was used to separate and purify the acylated C3G, the acylated rate was 30.78%. Fourier transform infrared spectroscopy and liquid chromatography mass spectrometry were used to confirm the basic structure of C3G. Lauric acid was combined with C3G. Lauric acid reacted with the glucoside's primary hydroxyl group and removed a molecule of water, thereby resulting in the obtained structure. The compositions of the unacylated C3G and acylated C3G were compared Downloaded by [New York University] at 00:42 22 June 2015 A c c e p t e d M a n u s c r i p t 2 under different temperatures and under illumination. The effects of different concentrations of additive compounds on the stability of acylated C3G were compared. Stability of acylated C3Gwas obviously higher than that of the unacylated C3G because of the higher stability of the ester group than the hydroxyl group. The primary hydroxyl esterification of glucoside improved C3G.

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

“…Malvidin-3-glucoside with different saturated fatty acid chain lengths using an enzymatic synthesis were obtained with low yields (22-40%) [21]. Zhao et al described direct acylation of cyanidin-3-glucoside with lauric acid in blueberry, which was essentially chemical acylation with an acylated yield of 30.8% [18]. On the other hand, the optimal reaction conditions were more economical and efficient than the conditions mentioned in previous studies.…”

“…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 ].…”

“…Current research progresses on the enzymatic acylation of cyanidin-3-glucoside by direct esterification reaction mainly focus on its synthesis, identification, evaluation of stability, and in vitro antioxidant capacities [ 18 , 23 ]. There is little information about the effects of reaction conditions, such as the molar ratio, enzyme addition, reaction temperature, and time.…”

Inhibitory effects of acylated blueberry anthocyanin on H22 murine tumors

“…The hybrid reaction was performed at 20°C and proceeded for 30 min. When the reaction was completed, methanol was used to stop the reaction (Zhao et al, 2015) Recovery of cell strains A frozen tube of H22 cell strain was taken out from liquid nitrogen tank, rapidly placed into 37°C water bath case, and shaken repetitively until no solid substance was left in the tube. The mouth of the frozen tube was cleaned with 75% ethanol on super clean bench.…”

Acylation and Stability Analysis of Blueberry Anthocyanins

“…Yawadio and Morita proved that the color of black rice anthocyanin-rich fraction enhanced by adding carboxylic acids into the anthocyanin-glucosides medium [5] . Zhao et al acylated directly cyanidin-3-glucoside with lauric acid, and found that the stability of acylated cyanidin-3-glucoside was obviously higher than that of the unacylated cyanidin-3-glucoside [6] . At present, the acylation of anthocyanins is mainly from the separation of natural products, and the use of chemical methods to synthesize acylated anthocyanins is rarely reported.…”