Phosphorylating polyphenols: Polyphenols are among the botanicals reported to possess substantial anticarcinogenic and antimutagenic activities because of their antioxidant and anti-inflammatory properties . Ajinomoto Omnichem and Estée Lauder disclose topical compositions containing phosphorylated polyphenols in combination with a topically acceptable carrier. The compositions enable delayed delivery of the polyphenol to keratinous tissues, where enzymes in the tissue dephosphorylate the polyphenol and return it to its native active form.
The compositions are particularly useful in the regulation of skin conditions. For example, in order to increase the stability of resveratrol in formulations, the reactive hydroxy groups of resveratrol were replaced by phosphate groups to give resveratrol triphosphate. HPLC analysis of the phosphorylated resveratrol shows that the degree of phosphorylation is very high; only very small amounts of the nonphosphorylated resveratrol are detected. Acid phosphatase from wheat germ was able to dephosphorylate resveratrol triphosphate and replace the phosphate groups of resveratrol triphosphate by hydroxy groups and as such converts the phosphorylated resveratrol to the original hydroxy-containing resveratrol.Cosmetic formulations were prepared containing 0.1% unmodifi ed resveratrol or 0.2% of phosphorylated resveratrol. At the end of four weeks, the phosphorylated resveratrol showed less color development than the unmodifi ed resveratrol, confi rming the enhanced color stability of the phosphorylated material. When applied to the skin, phosphorylated resveratrol was dephosphorylated, resulting in a time-dependent formation of resveratrol and a corresponding decrease of resveratrol triphosphate, thereby supporting the concept of delayed release of the active resveratrol, or any phosphorylated polyphenol, by the action of stratum corneum enzymes.
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