Covalent interaction of ascorbic acid with natural products.

Covalent interaction of ascorbic acid with natural products.
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DOI:
10.1016/j.phytochem.2009.09.028
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发表时间:
2009-12
期刊:
影响因子:
3.8
通讯作者:
Stevens JF
Stevens JF
中科院分区:
生物学2区
文献类型:
--
作者:
Kesinger NG;Stevens JF

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虽然抗坏血酸(维生素C)通常被认为是脯氨酸羟化酶的辅因子和生物抗氧化剂,但它也与天然产物形成共价键,我们在这里将其称为“抗坏血酸化”。已经从多种生物来源(从海藻到开花植物)中分离和表征了许多含有抗坏血酸部分的天然产物。这些化合物中的大多数是由于抗坏血酸盐的亲核取代或加成而形成的,例如来自芸苔属物种的抗坏血酸原是抗坏血酸化的吲哚衍生物。一些抗坏血酸化单宁似乎是由脱氢抗坏血酸亲电加成形成的。也有抗坏血酸与膳食多酚成环的实例,例如,表没食子儿茶素没食子酸酯(EGCG)和白藜芦醇衍生物。本文综述了33种抗坏血酸类天然产物及其生物活性。
While ascorbic acid (Vitamin C) is mostly known as a cofactor for proline hydroxylase and as a biological antioxidant, it also forms covalent bonds with natural products which we here refer to as ‘ascorbylation’. A number of natural products containing an ascorbate moiety has been isolated and characterized from a variety of biological sources, ranging from marine algae to flowering plants. Most of these compounds are formed as a result of nucleophilic substitution or addition by ascorbate, e.g. the ascorbigens from Brassica species are ascorbylated indole derivatives. Some ascorbylated tannins appear to be formed from electrophilic addition to dehydroascorbic acid. There are also examples of annulations of ascorbate with dietary polyphenols, e.g., epigallocatechin gallate (EGCG) and resveratrol derivatives. Herein is a survey of thirty-three ascorbylated natural products and their reported biological activities.
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