Structural features of procyanidin interactions with salivary proteins
Structural features of procyanidin interactions with salivary proteins
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DOI：
10.1021/jf000981z
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发表时间：
2001-02-01
影响因子：
6.1
通讯作者：
Mateus, N
中科院分区：
文献类型：
--
作者：
de Freitas, V;Mateus, N
合成了原花青素二聚体和三聚体C1，而从葡萄籽中分离出（-）-表儿茶素O-没食子酸酯和B2-3”-O-没食子酸酯。将人唾液分成两个部分。其中一种主要是α-淀粉酶，另一种主要是富含脯氨酸的蛋白质（PRP）。将原花青素化合物与每个唾液蛋白级分和牛血清白蛋白组合。使用浊度法观察蛋白质-多酚相互作用。（+）-儿茶素对PRP具有比（-）-表儿茶素更高的单宁比活性（TSA）（1.45对0.65 nephelos浊度单位/mg多酚）。这表明黄烷-3-醇的立体化学对它们与蛋白质的相互作用的影响。通过C（4）-C（8）类间黄烷键连接的原花青素二聚体比通过C（4）-C（6）键连接的对应物具有更大的TSA。没食子酰基与（-）-表儿茶素的C（3）羟基官能团或原花青素二聚体B2的表儿茶素部分酯化可增加TSA。这对二聚体的影响没有那么强，可能是由于B2-3”-O-没食子酸酯的预期“闭合”结构。
Procyanidin dimers and trimer C1 were synthesized, whereas (-)-epicatechin O-gallate and B2-3"-O-gallate were isolated from grape seeds. Human saliva was separated into two fractions. One of these was mainly a-amylase and the other mainly proline-rich proteins (PRPs). The procyanidin compounds were combined with each of the saliva protein fractions and with bovine serum albumin. The protein-polyphenol interactions were observed using nephelometry. (+)-Catechin had a higher tannin specific activity (TSA) for PRPs than (-)-epicatechin (1.45 versus 0.65 nephelos turbidity units/mg of polyphenol). This indicated the effect of the stereochemistry of flavan-3-ols on their interaction with proteins. Procyanidin dimers linked through a C(4)-C(8) interflavanoid bond had consistently greater TSA than their counterparts with a C(4)-C(6) linkage. Esterification of a galloyl group to the C(3) hydroxyl function of(-)-epicatechin or to the epicatechin moiety of procyanidin dimer B2 increased TSA. This was not as strong an effect for the dimer, probably as a result of the expected "closed" structure of B2-3"-O-gallate.