Synthesis of Biobased Phloretin Analogues: An Access to Antioxidant and Anti-Tyrosinase Compounds for Cosmetic Applications
The current cosmetic and nutraceutical markets are characterized by a strong consumer demand for a return to natural products that are less harmful to both the consumers and the environment than current petrosourced products. Phloretin, a natural dihydrochalcone (DHC) found in apple, has been widely...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-03-01
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| Series: | Antioxidants |
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| Online Access: | https://www.mdpi.com/2076-3921/10/4/512 |
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| author | Laurène Minsat Cédric Peyrot Fanny Brunissen Jean-Hugues Renault Florent Allais |
| author_facet | Laurène Minsat Cédric Peyrot Fanny Brunissen Jean-Hugues Renault Florent Allais |
| author_sort | Laurène Minsat |
| collection | DOAJ |
| description | The current cosmetic and nutraceutical markets are characterized by a strong consumer demand for a return to natural products that are less harmful to both the consumers and the environment than current petrosourced products. Phloretin, a natural dihydrochalcone (DHC) found in apple, has been widely studied for many years and identified as a strong antioxidant and anti-tyrosinase ingredient for cosmetic formulations. Its low concentration in apples does not allow it to be obtained by direct extraction from biomass in large quantities to meet market volumes and prices. Moreover, its remarkable structure prevents its synthesis through a green process. To overcome these issues, the synthesis of phloretin analogs appears as an alternative to access valuable compounds that are potentially more active than phloretin itself. Under such considerations, 12 chalcones (CHs) and 12 dihydrochalcones (DHCs) were synthesized through a green Claisen–Schmidt condensation using bio-based reagents. In order to evaluate the potential of these molecules, radical scavenging DPPH and anti-tyrosinase tests have been conducted. Moreover, the UV filtering properties and the stability of these analogs towards UV-radiations have been evaluated. Some molecules showed competitive antioxidant and anti-tyrosinase activities regarding phloretin. Two compounds in particular showed EC<sub>50</sub> lower than phloretin, one chalcone and one dihydrochalcone. |
| first_indexed | 2024-03-10T12:54:12Z |
| format | Article |
| id | doaj.art-67fc2f1f51fa476b8e10def0a1719e6a |
| institution | Directory Open Access Journal |
| issn | 2076-3921 |
| language | English |
| last_indexed | 2024-03-10T12:54:12Z |
| publishDate | 2021-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Antioxidants |
| spelling | doaj.art-67fc2f1f51fa476b8e10def0a1719e6a2023-11-21T12:01:59ZengMDPI AGAntioxidants2076-39212021-03-0110451210.3390/antiox10040512Synthesis of Biobased Phloretin Analogues: An Access to Antioxidant and Anti-Tyrosinase Compounds for Cosmetic ApplicationsLaurène Minsat0Cédric Peyrot1Fanny Brunissen2Jean-Hugues Renault3Florent Allais4URD Agro-Biotechnologies Industrielles (ABI), CEBB (Centre Européen de Biotechnologie et de Bioéconomie), AgroParisTech, 51110 Pomacle, FranceURD Agro-Biotechnologies Industrielles (ABI), CEBB (Centre Européen de Biotechnologie et de Bioéconomie), AgroParisTech, 51110 Pomacle, FranceURD Agro-Biotechnologies Industrielles (ABI), CEBB (Centre Européen de Biotechnologie et de Bioéconomie), AgroParisTech, 51110 Pomacle, FranceUniversité de Reims Champagne-Ardenne, CNRS, ICMR 7312, 51097 Reims, FranceURD Agro-Biotechnologies Industrielles (ABI), CEBB (Centre Européen de Biotechnologie et de Bioéconomie), AgroParisTech, 51110 Pomacle, FranceThe current cosmetic and nutraceutical markets are characterized by a strong consumer demand for a return to natural products that are less harmful to both the consumers and the environment than current petrosourced products. Phloretin, a natural dihydrochalcone (DHC) found in apple, has been widely studied for many years and identified as a strong antioxidant and anti-tyrosinase ingredient for cosmetic formulations. Its low concentration in apples does not allow it to be obtained by direct extraction from biomass in large quantities to meet market volumes and prices. Moreover, its remarkable structure prevents its synthesis through a green process. To overcome these issues, the synthesis of phloretin analogs appears as an alternative to access valuable compounds that are potentially more active than phloretin itself. Under such considerations, 12 chalcones (CHs) and 12 dihydrochalcones (DHCs) were synthesized through a green Claisen–Schmidt condensation using bio-based reagents. In order to evaluate the potential of these molecules, radical scavenging DPPH and anti-tyrosinase tests have been conducted. Moreover, the UV filtering properties and the stability of these analogs towards UV-radiations have been evaluated. Some molecules showed competitive antioxidant and anti-tyrosinase activities regarding phloretin. Two compounds in particular showed EC<sub>50</sub> lower than phloretin, one chalcone and one dihydrochalcone.https://www.mdpi.com/2076-3921/10/4/512phloretin analogueschalconesdihydrochalconesClaisen–Schmidt condensationDPPH testanti-tyrosinase |
| spellingShingle | Laurène Minsat Cédric Peyrot Fanny Brunissen Jean-Hugues Renault Florent Allais Synthesis of Biobased Phloretin Analogues: An Access to Antioxidant and Anti-Tyrosinase Compounds for Cosmetic Applications Antioxidants phloretin analogues chalcones dihydrochalcones Claisen–Schmidt condensation DPPH test anti-tyrosinase |
| title | Synthesis of Biobased Phloretin Analogues: An Access to Antioxidant and Anti-Tyrosinase Compounds for Cosmetic Applications |
| title_full | Synthesis of Biobased Phloretin Analogues: An Access to Antioxidant and Anti-Tyrosinase Compounds for Cosmetic Applications |
| title_fullStr | Synthesis of Biobased Phloretin Analogues: An Access to Antioxidant and Anti-Tyrosinase Compounds for Cosmetic Applications |
| title_full_unstemmed | Synthesis of Biobased Phloretin Analogues: An Access to Antioxidant and Anti-Tyrosinase Compounds for Cosmetic Applications |
| title_short | Synthesis of Biobased Phloretin Analogues: An Access to Antioxidant and Anti-Tyrosinase Compounds for Cosmetic Applications |
| title_sort | synthesis of biobased phloretin analogues an access to antioxidant and anti tyrosinase compounds for cosmetic applications |
| topic | phloretin analogues chalcones dihydrochalcones Claisen–Schmidt condensation DPPH test anti-tyrosinase |
| url | https://www.mdpi.com/2076-3921/10/4/512 |
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