Effects and mechanism of natural phenolic acids/fatty acids on copigmentation of purple sweet potato anthocyanins

Xiaorui Lv; Jianlou Mu; Wenxiu Wang; Yaqiong Liu; Xiaomin Lu; Jianfeng Sun; Jie Wang; Qianyun Ma

doi:10.1016/j.crfs.2022.08.003

Effects and mechanism of natural phenolic acids/fatty acids on copigmentation of purple sweet potato anthocyanins

Curr Res Food Sci. 2022 Aug 13:5:1243-1250. doi: 10.1016/j.crfs.2022.08.003. eCollection 2022.

Authors

Xiaorui Lv¹, Jianlou Mu¹, Wenxiu Wang¹, Yaqiong Liu¹, Xiaomin Lu², Jianfeng Sun¹, Jie Wang¹, Qianyun Ma¹

Affiliations

¹ College of Food Science and Technology, Hebei Agricultural University, Baoding, 071000, China.
² Department of Forest Biomaterials, North Carolina State University, Raleigh, NC, 27695, USA.

Abstract

Anthocyanins are attractive alternatives to colorants; however, their low color stability hinders practical application. Copigmentation can enhance both the color intensity and color stability of complexes. Herein, we report an investigation of copigmentation reactions between purple sweet potato anthocyanins (PSA1) and phenolic acids (tannic, ferulic, and caffeic acids) or fatty acids (tartaric and malic acids) at pH 3.5. The effects of the mole ratios of the copigment and the reaction temperature were examined. In addition, quantum mechanical computations were performed to investigate molecular interactions. The optimum PSA:copigment molar ratio was found to be 1:100. The strongest bathochromic and hyperchromic effects were observed for copigmentation with tannic acid (Tan), which might be attributable to the fact that its HOMO-LUMO energy gap was the smallest among the investigated copigments, and because it has a greater number of phenolic aromatic and groups to form more van der Waals and hydrogen bond interactions. However, the formation of the PSA-caffeic acid (Caf) complex was accompanied by the greatest drop in enthalpy (-33.18 kJ/mol) and entropy (-74.55 kJ/mol), and this was the most stable complex at 90 °C. Quantum mechanical calculations indicated that hydrogen bonds and van der Waals force interactions contributed to the color intensification effect of copigmentation. These findings represent an advancement in our understanding of the properties of PSA, expanding the application scope of this natural product.

Keywords: Anthocyanin; BCPs, bond critical point; Bathochromic shift; CCPs, cage critical points; Caf, caffeic acid; Copigmentation; DFT, density functional theory; Fer, ferulic acid; HBs, hydrogen bond; Hyperchromic effect; IGM, independent gradient model; Mal, malic acid; PCG, petunidin-3-coumaroylrutinoside-5-glucoside; PSA, purple sweet potato anthocyanins; Quantum mechanic; RCPs, ring citica points; Tan, tannic acid; Tar, tartaric acid; vdWs, van der Waals.