Isolation and purification of two antioxidant isomers of resveratrol dimer from the wine grape by counter-current chromatography
Isolation and purification of two antioxidant isomers of resveratrol dimer from the wine grape by counter-current chromatography
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逆流色谱法分离纯化酿酒葡萄中白藜芦醇二聚体的两种抗氧化异构体
DOI：
10.1002/jssc.201600004
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发表时间：
2016-06-01
影响因子：
3.1
通讯作者：
Pan, Yuanjiang
中科院分区：
文献类型：
--
作者：
Kong, Qingjun;Ren, Xueyan;Pan, Yuanjiang
白藜芦醇二聚体属于二苯乙烯类化合物，它与原花青素、花青素、儿茶素和黄酮醇一起是在葡萄和红葡萄酒中发现的天然酚类化合物。二苯乙烯类化合物有多种结构异构体，所有这些异构体都具有不同的生物学性质。采用逆流色谱技术，以正己烷/乙酸乙酯/甲醇/水(2：5：4：5，v/v)为溶剂，从酿酒葡萄茎中分离纯化二苯乙烯类化合物。从白藜芦醇二聚体的粗品中一步分离得到两个异构体反式-β-长春花素和反式-长春花素，经高效液相色谱法测定，其纯度分别为93.2%和97.5%。两个化合物的结构经H-1和C-13核磁共振谱确证。此外，通过1，1-二苯基-2-苦基肼(DPPH)测定了它们的抗氧化活性。在该模型中，反式-β-长春花素的抗氧化活性高于反式-β-长春花素。结果表明，逆流层析是一种分离纯化酿酒葡萄多酚的有效方法。此外，DPPH自由基活性测定表明，在相同浓度下，分离得到的成分反式-β-长春花素具有比反式-g-长春花素更强的抗氧化活性，略弱于维生素E。
Resveratrol dimers belong to a group of compounds called stilbenes, which along with proanthocyanidins, anthocyanins, catechins, and flavonols are natural phenolic compounds found in grapes and red wine. Stilbenes have a variety of structural isomers, all of which exhibit various biological properties. Counter-current chromatography with a two-phase solvent system composed of n-hexane/ethyl acetate/methanol/water (2:5:4:5, v/v/v/v) was applied to isolate and purify stilbene from the stems of wine grape. Two isomers of resveratrol dimers trans-epsilon-viniferin and trans-delta-viniferin were obtained from the crude sample in a one-step separation, with purities of 93.2 and 97.5%, respectively, as determined by high-performance liquid chromatography. The structures of these two compounds were identified by H-1 and C-13 NMR spectroscopy. In addition, their antioxidant activities were assessed by 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. The antioxidant activities of trans-delta-viniferin were higher than that of trans-epsilon-viniferin in this model. This work demonstrated that counter-current chromatography is a powerful and effective method for the isolation and purification of polyphenols from wine grape. Additionally, the DPPH radical assay showed that the isolated component trans-delta-viniferin exhibited stronger antioxidant activities than trans-g-viniferin and a little bit weaker than vitamin E at the same concentration.