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抗坏血酸与天然产物的共价相互作用。

Covalent interaction of ascorbic acid with natural products.

机构信息

Department of Pharmaceutical Sciences, The Linus Pauling Institute, Oregon State University, Corvallis, OR 97331, USA.

出版信息

Phytochemistry. 2009 Dec;70(17-18):1930-9. doi: 10.1016/j.phytochem.2009.09.028. Epub 2009 Oct 28.

DOI:10.1016/j.phytochem.2009.09.028
PMID:19875138
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2787919/
Abstract

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 either 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 33 ascorbylated natural products and their reported biological activities.

摘要

虽然抗坏血酸(维生素 C)主要作为脯氨酰羟化酶的辅助因子和生物抗氧化剂为人所知,但它也与我们这里称为“抗坏血酸化”的天然产物形成共价键。已经从各种生物来源(从海洋藻类到开花植物)分离和鉴定出许多含有抗坏血酸盐部分的天然产物。这些化合物中的大多数是通过抗坏血酸的亲核取代或加成形成的,例如来自芸薹属植物的抗坏血素是抗坏血酸化吲哚衍生物。一些抗坏血酸化单宁似乎是通过去氢抗坏血酸的亲电加成形成的。也有抗坏血酸与膳食多酚(例如表没食子儿茶素没食子酸酯(EGCG)和白藜芦醇衍生物)环合的例子。本文综述了 33 种抗坏血酸化天然产物及其报道的生物活性。

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Sulforaphane but not ascorbigen, indole-3-carbinole and ascorbic acid activates the transcription factor Nrf2 and induces phase-2 and antioxidant enzymes in human keratinocytes in culture.萝卜硫素而非抗坏血酸苷、吲哚-3-甲醇和抗坏血酸可激活人角质形成细胞培养物中的转录因子 Nrf2,并诱导其Ⅱ相和抗氧化酶的表达。
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