Laboratoire Mer, Molécules, Santé, EA 2160, Université du Maine, Institut Universitaire de Technologie de Laval, 52 rue des Drs Calmette et Guérin, BP 2045, 53020 Laval cedex 9, France.
UR1268, Biopolymères, Interactions, Assemblages, INRA, F-44300 Nantes, France.
Carbohydr Polym. 2012 Sep 1;90(1):152-8. doi: 10.1016/j.carbpol.2012.05.008. Epub 2012 May 11.
Chlorogenic acid (5-caffeoylquinic acid) is a hydrophilic phenolic compound with antioxidant properties. Because of its high polarity, these properties may be altered when formulated in oil-based food. There is therefore an interest in trying to protect the natural antioxidant by molecular encapsulation. Amylose, the linear fraction of starch with essentially α(1-4) linkages, is well known for its ability to form semi-crystalline complexes with a variety of small ligands. Monoacyl lipids, as well as smaller ligands such as alcohols or flavor compounds, are able to induce the formation of left-handed amylose single helices. In contrast, chlorogenic acid is a bulky molecule whose topology requires the amylose helix to be distorted, which could prevent amylose complexation. An innovative strategy has been developed to overcome this problem by grafting an aliphatic chain onto chlorogenic acid then trapping this chain in the helical cavity. The lipophilization reaction was used to obtain a palmitoyl chlorogenic acid derivative and the amylose-palmitoyl chlorogenic acid assemblies were studied by X-ray diffraction, differential scanning calorimetry and NMR to elucidate the interaction. The results showed that such interactions between amylose and palmitoyl chlorogenic acid are effective.
绿原酸（5-咖啡酰奎宁酸）是一种具有抗氧化性能的亲水性酚类化合物。由于其高极性，当在油基食品中进行配方时，这些性质可能会发生改变。因此，人们有兴趣尝试通过分子包封来保护天然抗氧化剂。直链淀粉是淀粉的线性部分，其本质上具有α（1-4）键合，以其与各种小分子配体形成半结晶复合物的能力而闻名。单酰基脂质以及较小的配体，如醇或风味化合物，能够诱导左手直链淀粉单螺旋的形成。相比之下，绿原酸是一个庞大的分子，其拓扑结构要求直链淀粉螺旋发生扭曲，这可能会阻止直链淀粉的络合。通过将脂肪链接枝到绿原酸上，然后将该链捕获在螺旋腔中，开发了一种创新的策略来克服这个问题。利用脂化反应获得了棕榈酰绿原酸衍生物，并通过 X 射线衍射、差示扫描量热法和 NMR 研究了直链淀粉-棕榈酰绿原酸组装体，以阐明相互作用。结果表明，直链淀粉和棕榈酰绿原酸之间存在这种相互作用。
