Ultrahigh Pressure Facilitates the Acylation of Malvidin and Chlorogenic Acid to Increase the Stability and Protective Effect of Malvidin Derivatives on H2O2‑Induced ARPE-19 Cells

• Published in: Journal of agricultural and food chemistry 2021-11, Vol.69 (46), p.13990-14003
• Main Authors: Liu, Xinyao, Li, Sheng, Wang, Zhitong, Wang, Xinyuan, He, Yang, Wen, Liankui
• Format: Article
• Language: English
• Subjects: Functional Structure/Activity Relationships
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/acs.jafc.1c03133

We explored the effects of ultrahigh-pressure technology and chlorogenic acid on the color stability and structure–activity relationship of malvidin (MV). Experimental conditions were optimized through single-factor experiments and response surface analysis at a pressure of 300 MPa, mass ratio of MV to chlorogenic acid of 1:3.64 (w/w), and time of 5 min. Compared with MV, MV derivatives showed higher stability and in vitro antioxidant activity. X-ray diffraction analysis, UV–vis spectroscopy, Fourier transform infrared spectroscopy, high-performance liquid chromatography, and mass spectrometry were conducted to determine the structures of MV derivatives for the first time. Ultrahigh pressure facilitated acylation of chlorogenic acid and MV and produced four new MV derivatives. Analysis of the effect of malvidin-3-O-6-(acrylic acid-(2-hydroxy, 4-carboxy-cyclohexanol) ester)-guaiacol (Mv3ACEC) on ARPE-19 cells exposed to H2O2 by RNA transcriptome sequencing showed that Mv3ACEC simultaneously inhibited various inflammatory and apoptotic signal transduction pathways, exerted a synergistic effect, and partly inhibited cell apoptosis through the MAPK signaling pathway. Therefore, the results show that ultrahigh pressure will cause acylation of chlorogenic acid and MV to produce four new MV derivatives, and MV derivatives protect ARPE-19 cells from H2O2-induced oxidative stress.