Synthesis, characterisation and antioxidant features of procyanidin B4 and malvidin-3-glucoside stearic acid derivatives

卷:174

Cruz, Luis ; Fernandes, Virginia C. ; Araujo, Paula ; Mateus, Nuno ; de Freitas, Victor

关键词: Procyanidin B4;    Malvidin-3-glucoside;    Stearic acid;    Lipophilization;    NMR;    Mass spectrometry;   

DOI  :  10.1016/j.foodchem.2014.11.062

学科分类：食品科学和技术

【 摘 要 】

The acylation of procyanidin B4 with a saturated fatty acid chloride containing 18 carbon atoms was studied in order to obtain procyanidin B4 3-O-di-stearic acid conjugate. This compound was structurally characterised by mass spectrometry and 1D and 2D NMR techniques. Derivatization of malvidin-3-glucoside using stearoyl chloride in acetonitrile was also performed yielding mono-, di- and tri-stearic ester derivatives. The novel derivatives obtained revealed significant antioxidant activity, although lower than the respective precursors. However, the chemical modification of anthocyanins and procyanidins (water soluble pigments) to more lipophilic compounds has the advantage of increased bioavailability in biological matrices, and to potentiate their application in food matrices and cosmetic products. (C) 2014 Elsevier Ltd. All rights reserved.