Malvidin 3-Glucoside–Fatty Acid Conjugates: From Hydrophilic toward Novel Lipophilic Derivatives,Journal of Agricultural and Food Chemistry

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Malvidin 3-Glucoside–Fatty Acid Conjugates: From Hydrophilic toward Novel Lipophilic Derivatives
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2017-02-16 00:00:00 , DOI: 10.1021/acs.jafc.6b05461
Luís Cruz ₁ , Marta Guimarães ₁ , Paula Araújo ₁ , Ana Évora ₁ , Victor de Freitas ₁ , Nuno Mateus ₁

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This work describes the lipophilization reactions of malvidin 3-glucoside with different saturated fatty acid chain lengths using an enzymatic synthesis and the study of their physical–chemical and antioxidant properties. The lipophilic anthocyanins were obtained with satisfactory yields (22–40%) after column chromatography purifications, and they revealed the same appealing chromatic features of the parent anthocyanin. All of the compounds were characterized by mass spectrometry, confirming the regioselective acylation on the glucose moiety. The octanol–water partition coefficients and the hydrophobicity index of the different derivatives were determined, confirming a lipophilicity increase concomitant with the fatty acid chain length. The antioxidant profile was also evaluated by using two in vitro methods (β-carotene–lineolate method and oxygen consumption assay). Overall, a maximum of antioxidant activity was achieved when malvidin 3-glucoside was conjugated with caprylic acid (C8). Altogether, the results obtained provide a good perspective for the technological application of these functionalized anthocyanins in the cosmetics and food industries.

中文翻译：

Malvidin 3-葡萄糖苷-脂肪酸结合物：从亲水性向新型亲脂性衍生物转变

这项工作描述了使用酶促合成方法对具有不同饱和脂肪酸链长的麦维达菌素3-葡萄糖苷的脂化反应，并研究了它们的理化性质和抗氧化剂性质。柱色谱纯化后，亲脂性花色苷的收率令人满意（22-40％），并且它们显示出与母体花色苷相同的吸引人的色度特征。所有化合物均通过质谱表征，证实了葡萄糖部分的区域选择性酰化。确定了不同衍生物的辛醇-水分配系数和疏水性指数，证实了亲脂性随脂肪酸链长的增加而增加。还使用两种体外方法（β-胡萝卜素-亚麻酸酯法和耗氧量测定法）评估了抗氧化剂的特性。总体而言，当麦维达菌素3-葡萄糖苷与辛酸（C8）共轭时，获得了最大的抗氧化活性。总之，获得的结果为这些功能化的花色苷在化妆品和食品工业中的技术应用提供了良好的前景。

更新日期：2017-02-16

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