New acylated cyanidin glycosides extracted from underutilized potential sources: Enzymatic synthesis, antioxidant activity and thermostability

• Published in: Food chemistry 2020-03, Vol.309, p.125796-125796, Article 125796
• Main Authors: Fernandez-Aulis, Fernanda, Torres, Andrea, Sanchez-Mendoza, Ernesto, Cruz, Luis, Navarro-Ocana, Arturo
• Format: Article
• Language: English
• Subjects: Acylated anthocyanin; Acylation; Anthocyanins - chemistry; Anthocyanins - metabolism; Antioxidants - chemistry; Cinnamates - chemistry; Dihydrocinnamic acids; Enzymatic esterification; Esterification; Fungal Proteins - metabolism; Glucosides - chemistry; Glucosides - metabolism; Lipase - metabolism; Lipases; Magnetic Resonance Spectroscopy; Prunus domestica - chemistry; Prunus domestica - metabolism; Solvents - chemistry; Temperature
• ISSN: 0308-8146; 1873-7072
• DOI: 10.1016/j.foodchem.2019.125796

•Evaluation of five underutilized plants to obtain sources of cyanidin glycosides.•Reaction conditions of enzymatic esterification to anthocyanins for the food industry.•Synthesis of four new anthocyanins derived from dihydrocinnamic acids.•Development of cyanidin esters with more thermostability and antioxidant activity. Interest in anthocyanins has increased remarkably in recent decades, although their wider application has been hampered by instability problems. Thus, this study aimed at developing a strategy to gain access to more stable anthocyanins via enzymatic esterification. For that purpose, three cyanidin derivatives were obtained from underutilized, but easily accessible sources, and their total anthocyanin content was quantified. The purity of cyanidins obtained ranged from 40% to 88% depending on their source. Subsequently, the critical enzymatic reaction conditions were established, and the best results were found using tert-butanol as a solvent, 20 g/L of lipase B from Candida Antarctica, and vinyl cinnamate as acyl donor at ratio 250:1 (acyl donor to anthocyanin). Finally, five new acylated anthocyanin derivatives were synthesized with improved antioxidant activity and thermostability, in comparison to the cyanidin-3-glucoside, which is an advantageous feature for industrial applications.