TitleCovalent interaction of ascorbic acid with natural products.
Publication TypeJournal Article
Year of Publication2009
AuthorsKesinger NG, Stevens JF
Date Published2009 Dec
KeywordsAscorbic Acid, Eukaryota, Flavonoids, Molecular Structure, Phenols, Plant Extracts, Polyphenols

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.

Alternate JournalPhytochemistry
PubMed ID19875138
PubMed Central IDPMC2787919
Grant ListR01 HL081721 / HL / NHLBI NIH HHS / United States
R01 HL081721-04 / HL / NHLBI NIH HHS / United States
R01HL081721 / HL / NHLBI NIH HHS / United States