Influence of phenolic acids/aldehydes on color intensification of cyanidin-3-O-glucoside, the main anthocyanin in sugarcane (Saccharum officinarum L.)
2022
Xu, Zhengming | Wang, Chengtao | Yan, Huaifeng | Zhao, Zhengang | You, Lijun | Ho, Chi-Tang
Sugarcane contains various anthocyanins, which are responsible for the colors present in sugarcane. In this study, the color intensification of the major anthocyanin, cyanidin-3-O-glucoside, by phenolic acids/aldehydes (ferulic acid, vanillic acid, p-coumaric acid, syringic aldehyde and vanillic aldehyde) was investigated. The color enhancement of cyanidin-3-O-glucoside (hyperchromic effect and bathochromic shift) was affected by the temperature and concentration of phenolic acids/aldehydes present. Reactions were spontaneous and exothermic, as determined using different thermodynamic parameters (ΔG⁰, ΔH⁰, ΔS⁰). Quantum chemical calculations demonstrated their intermolecular interaction differences, and AIM analysis indicated that hydrogen bonds and van der Waals force interactions contributed to color. Pyranoanthocyanins derived from cyanidin-3-O-glucoside and ferulic/p-coumaric acids during storage were recognized as cyanidin-3-O-glucoside-vinylphenol and cyanidin-3-O-glucoside-vinylguaiacol, respectively, by UPLC-ESI-QTOF-MS/MS. The electron-donating substituents on the aromatic ring of ferulic/p-coumaric acids stabilized the intermediately formed carbenium ion. Decarboxylation and further oxidation of the pyran moieties to the aromatic heterocycles resulted in the final products.
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