"Sweet Flavonoids": Glycosidase-Catalyzed Modifications.

"Sweet Flavonoids": Glycosidase-Catalyzed Modifications.
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DOI:
10.3390/ijms19072126
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发表时间:
2018-07-21
影响因子:
5.6
通讯作者:
Valentová K
Valentová K
中科院分区:
生物学2区
文献类型:
--
作者:
Slámová K;Kapešová J;Valentová K

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天然类黄酮,特别是糖基化形式的类黄酮,是植物、水果和蔬菜中含量最丰富的酚类化合物。它们表现出各种有益的生理效应,这使它们在广泛的科学领域普遍引起人们的兴趣。本文综述了近年来利用糖苷酶对不同的黄酮类化合物进行糖苷修饰的研究进展,包括糖基的选择性修剪和天然糖苷酶和突变糖苷酶对黄酮苷元的糖基化作用。黄酮类化合物的糖基化大大提高了它们的水溶性,从而提高了它们的生物利用度。抗氧化剂和大多数生物活性通常在糖苷中不那么明显,但一些特定的生物活性得到增强。L-鼠李糖(6-deoxy-α-L-甘露糖)在鼠李糖苷、芦丁苷(芦丁、橙皮苷)和新橙皮苷(柚皮苷)中的存在对黄酮苷的性质起着重要的作用,黄酮苷可被认为是“前药”。糖苷酶的天然水解性被广泛应用于生物技术脱糖基化过程中,产生相应的苷元或部分脱糖基黄酮类化合物。此外,脱糖作用在食品工业中非常常用,目的是改善饮料的感官特性,如柑橘汁的脱苦或增强葡萄酒的香气。因此,天然和突变的糖苷酶是黄酮苷类化合物修饰的极佳工具。
Natural flavonoids, especially in their glycosylated forms, are the most abundant phenolic compounds found in plants, fruit, and vegetables. They exhibit a large variety of beneficial physiological effects, which makes them generally interesting in a broad spectrum of scientific areas. In this review, we focus on recent advances in the modifications of the glycosidic parts of various flavonoids employing glycosidases, covering both selective trimming of the sugar moieties and glycosylation of flavonoid aglycones by natural and mutant glycosidases. Glycosylation of flavonoids strongly enhances their water solubility and thus increases their bioavailability. Antioxidant and most biological activities are usually less pronounced in glycosides, but some specific bioactivities are enhanced. The presence of l-rhamnose (6-deoxy-α-l-mannopyranose) in rhamnosides, rutinosides (rutin, hesperidin) and neohesperidosides (naringin) plays an important role in properties of flavonoid glycosides, which can be considered as “pro-drugs”. The natural hydrolytic activity of glycosidases is widely employed in biotechnological deglycosylation processes producing respective aglycones or partially deglycosylated flavonoids. Moreover, deglycosylation is quite commonly used in the food industry aiming at the improvement of sensoric properties of beverages such as debittering of citrus juices or enhancement of wine aromas. Therefore, natural and mutant glycosidases are excellent tools for modifications of flavonoid glycosides.
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