Enzymatic fatty acid acylation of cyanidin-3-O-glucoside extracted from black rice bran: thermostability, lipophilicity, cytotoxicity and absorption studies

IF 8.5 1区农林科学 Q1 CHEMISTRY, APPLIED

Food Chemistry Pub Date : 2025-04-15 DOI:10.1016/j.foodchem.2025.144353

Eduardo Leonarski , Karina Cesca , Débora de Oliveira , Acácio A.F. Zielinski , Nuno Mateus , Victor de Freitas , Hélder Oliveira , Luís Cruz

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Abstract

Lipophilization technique has been a promising alternative to reduce anthocyanin's chemical instability and to increase their lipid affinity. Enzymatic acylation of cyanidin-3-O-glucoside (C3G) extracted from black rice bran was optimized towards the fatty acid donor, solvent, enzyme concentration, and temperature parameters. The most promising lipophilic conjugate (C3G-C8) was obtained with 53 % yield at 60 °C, 15 g/L enzyme in acetonitrile:DMSO (10:1). Regarding the thermostability, an increase in the half-life time for C3G-C8 at different pH values (3, 5, and 7) compared to C3G was observed. The octanol−water partition coefficients confirmed its superior lipophilicity (log P = 1.37) compared to its precursor (log P = −1.59). No cytotoxicity was observed for both compounds at concentrations up to 200 μM for NCI-N87 cells and Caco-2:HT29-MTX coculture. Both anthocyanins presented similar transepithelial transport efficiency using the coculture (about 1.2 %). Overall, C3G-C8 showed higher affinity than its precursor for application in lipid-based products.

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来源期刊

Food Chemistry 工程技术-食品科技

CiteScore

16.30

自引率

10.20%

发文量

3130

审稿时长

122 days

期刊介绍： Food Chemistry publishes original research papers dealing with the advancement of the chemistry and biochemistry of foods or the analytical methods/ approach used. All papers should focus on the novelty of the research carried out.