Charakterisierung von <i>aci</i>‐Reduktonen mit Xanthydrol

Schwall, Horst; Regitz, Manfred; Urtel, Rolf

doi:10.1002/jlac.19707340108

Cited by 2 publications

(1 citation statement)

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“…Intermediate adducts can dissociate or form stable products by subsequent reactions, e.g., oxidation, dehydration, or hemiacetal or hemiketal formation. For instance, C-alkylated products can be formed via Michael addition, such as the reaction of ascorbate with acrolein (Fodor et al, 1983), or via S N 1 substitution provided the carbocation is sufficiently stabilized via resonance (such as in the reaction of ascorbate with xanthydrol (Schwall et al, 1970) (Fig. 1).…”

Section: Ascorbate As Nucleophilementioning

confidence: 99%

Covalent interaction of ascorbic acid with natural products

Kesinger

Stevens

2009

Phytochemistry

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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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Section: Ascorbate As Nucleophilementioning

confidence: 99%