Influence of phenolic acids/aldehydes on color intensification of cyanidin-3-O-glucoside, the main anthocyanin in sugarcane (Saccharum officinarum L.)

Abstract

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.

Keywords: Color intensification; Cyanidin-3-O-glucoside; Derivatives; Phenolic acids/aldehydes; Saccharum officinarum L..