Abstract
The phenolic compound phloridzin (phloretin 2′-O-glucoside, variously named phlorizin, phlorrhizin, phlorhizin or phlorizoside) is a prominent member of the chemical class of dihydrochalcones, which are phenylpropanoids. Phloridzin is specifically found in apple and apple juice and known for its biological properties. In particular we were attracted by potential dermo-cosmetic applications. Here we report the synthesis, stability studies and antimicrobial activity of compound F2, a new semi-synthetic derivative of phloridzin. The new derivative was also included in finished formulations to evaluate its stability with a view to a potential topical use. Stability studies were performed by HPLC; PCL assay and ORAC tests were used to determine the antioxidant activity. F2 presented an antioxidant activity very close to that of the parent phloridzin, but, unlike the latter, was more stable in formulations. To further explore potential health claims, antifungal activity of phloridzin and its derivative F2 were determined; the results, however, were rather low; the highest value was 31,6% of inhibition reached by F2 on Microsporum canis at the highest dose.
Highlights
IntroductionPhloridzin (phloretin 2′-glucoside, phlorhizin, phlorrhizin) belongs to the chemical class of dihydrochalcones, phenylpropanoids with structures closely related to those of the immediate flavonoid precursors, the chalcones, and it is the major phenolic glucoside found in apple trees
Phloridzin belongs to the chemical class of dihydrochalcones, phenylpropanoids with structures closely related to those of the immediate flavonoid precursors, the chalcones, and it is the major phenolic glucoside found in apple trees.Phloridzin has a bitter taste that contributes to the characteristic tang of cider [1], the color of the apple juices derives from its dimerized oxidation products [2]
The Oxygen Radical Absorbance Capacity (ORAC) test results show a high antioxidant activity with respect to the peroxyl radical, with the best results seen for phloridzin as compared to F2 (8.78 and 4.27 μmol Trolox/mmol product respectively) probably due to the fact that, being more lipophilic, within 24 h of analysis it might precipitate in the PBS (Figure 4)
Summary
Phloridzin (phloretin 2′-glucoside, phlorhizin, phlorrhizin) belongs to the chemical class of dihydrochalcones, phenylpropanoids with structures closely related to those of the immediate flavonoid precursors, the chalcones, and it is the major phenolic glucoside found in apple trees. These effects, based on the antioxidant activity, are very interesting to the dermo-cosmetic field in view of the increasing attention of dermatologists to the solar DNA induced damages In this application, the protective role was assessed against ultraviolet B rays in comparison. Polyphenols-like structures offer interesting dermo-cosmetic applications as potential antifungal agents, and this aspect has been investigated in extracts from Mallus species [34] Due to this latter information we focused our attention on the antifungal activities of phloridzin. In line with our recent strategy applied on other natural phenylpropanoids derivatives [35] we investigated novel phoridzin semi-synthetic derivatives in order to devise possible pro-drug forms The latter were investigated for stability in solutions at different pH and storage conditions and in finished dermo-cosmetic formulations. The leading concept was that derivatization will increase the range of applications
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