Synthesis, Antioxidant and Antimicrobial Activity of a New Phloridzin Derivative for Dermo-Cosmetic Applications

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 kno...

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Main Authors: Silvia Vertuani, Stefano Manfredini, Chiara Beatrice Vicentini, Carlo Romagnoli, Elisa Andreotti, Emanuela Scalambra, Anna Baldisserotto, Gemma Malisardi
Format: Article
Language:English
Published: MDPI AG 2012-11-01
Series:Molecules
Subjects:
Online Access:http://www.mdpi.com/1420-3049/17/11/13275
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author Silvia Vertuani
Stefano Manfredini
Chiara Beatrice Vicentini
Carlo Romagnoli
Elisa Andreotti
Emanuela Scalambra
Anna Baldisserotto
Gemma Malisardi
author_facet Silvia Vertuani
Stefano Manfredini
Chiara Beatrice Vicentini
Carlo Romagnoli
Elisa Andreotti
Emanuela Scalambra
Anna Baldisserotto
Gemma Malisardi
author_sort Silvia Vertuani
collection DOAJ
description 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.
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spelling doaj.art-12da6d57ee34408989f61b41a57bc59a2022-12-22T01:04:38ZengMDPI AGMolecules1420-30492012-11-011711132751328910.3390/molecules171113275Synthesis, Antioxidant and Antimicrobial Activity of a New Phloridzin Derivative for Dermo-Cosmetic ApplicationsSilvia VertuaniStefano ManfrediniChiara Beatrice VicentiniCarlo RomagnoliElisa AndreottiEmanuela ScalambraAnna BaldisserottoGemma MalisardiThe 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.http://www.mdpi.com/1420-3049/17/11/13275phloridzinF2antioxidant activityPCLHPLC analysisstability in dermocosmetic formulationsantifungal activity
spellingShingle Silvia Vertuani
Stefano Manfredini
Chiara Beatrice Vicentini
Carlo Romagnoli
Elisa Andreotti
Emanuela Scalambra
Anna Baldisserotto
Gemma Malisardi
Synthesis, Antioxidant and Antimicrobial Activity of a New Phloridzin Derivative for Dermo-Cosmetic Applications
Molecules
phloridzin
F2
antioxidant activity
PCL
HPLC analysis
stability in dermocosmetic formulations
antifungal activity
title Synthesis, Antioxidant and Antimicrobial Activity of a New Phloridzin Derivative for Dermo-Cosmetic Applications
title_full Synthesis, Antioxidant and Antimicrobial Activity of a New Phloridzin Derivative for Dermo-Cosmetic Applications
title_fullStr Synthesis, Antioxidant and Antimicrobial Activity of a New Phloridzin Derivative for Dermo-Cosmetic Applications
title_full_unstemmed Synthesis, Antioxidant and Antimicrobial Activity of a New Phloridzin Derivative for Dermo-Cosmetic Applications
title_short Synthesis, Antioxidant and Antimicrobial Activity of a New Phloridzin Derivative for Dermo-Cosmetic Applications
title_sort synthesis antioxidant and antimicrobial activity of a new phloridzin derivative for dermo cosmetic applications
topic phloridzin
F2
antioxidant activity
PCL
HPLC analysis
stability in dermocosmetic formulations
antifungal activity
url http://www.mdpi.com/1420-3049/17/11/13275
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