Phytyl Phenolipids: Structurally Modified Antioxidants with Superior Lipid Membrane Interaction
A set of procedures was developed for the simple synthesis of phytyl phenolipids, which resulted in high yields (70–95%) of phytyl esters of caffeic, protocatechuic, homoprotocatechuic, and dihydrocaffeic acids. Initial characterization revealed that these new compounds exhibited similar radical sca...
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MDPI AG
2025-05-01
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| author | Vânia Costa Marlene Costa Rute Rebelo Francisca Arques Mariana Ferreira Paula Gameiro Tomás Barros Dulce Geraldo Luís S. Monteiro Fátima Paiva-Martins |
| author_facet | Vânia Costa Marlene Costa Rute Rebelo Francisca Arques Mariana Ferreira Paula Gameiro Tomás Barros Dulce Geraldo Luís S. Monteiro Fátima Paiva-Martins |
| author_sort | Vânia Costa |
| collection | DOAJ |
| description | A set of procedures was developed for the simple synthesis of phytyl phenolipids, which resulted in high yields (70–95%) of phytyl esters of caffeic, protocatechuic, homoprotocatechuic, and dihydrocaffeic acids. Initial characterization revealed that these new compounds exhibited similar radical scavenging activity and liposolubility to α-tocopherol, a key antioxidant present in membranes. Cyclic voltammetry analysis indicated that the phytyl derivatives had lower anodic peak potentials compared to the original phenolic acids, with electron transfer following an adsorption-controlled mechanism. In phosphatidylcholine large unilamellar vesicles (LUVs), phytyl esters demonstrated remarkable efficiency in preventing liposome autoxidation when compared to α-tocopherol. Despite their strong radical scavenging capacity and membrane penetration ability, the antioxidant effectiveness of the phytyl esters in liposomes was influenced by the structure of their polyphenolic moiety. These new compounds are considered promising candidates for future pharmacological applications against oxidative stress in lipoproteins and cells, warranting further evaluation of their antioxidant and anti-inflammatory effects in cellular models and in vivo. |
| format | Article |
| id | doaj-art-c0dd53d150fe4673825ebaf7ef62b6b8 |
| institution | OA Journals |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-c0dd53d150fe4673825ebaf7ef62b6b82025-08-20T02:34:01ZengMDPI AGMolecules1420-30492025-05-013010219310.3390/molecules30102193Phytyl Phenolipids: Structurally Modified Antioxidants with Superior Lipid Membrane InteractionVânia Costa0Marlene Costa1Rute Rebelo2Francisca Arques3Mariana Ferreira4Paula Gameiro5Tomás Barros6Dulce Geraldo7Luís S. Monteiro8Fátima Paiva-Martins9Associated Laboratory for Green Chemistry (LAQV) of the Network of Chemistry and Technology (REQUIMTE), Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, PortugalAssociated Laboratory for Green Chemistry (LAQV) of the Network of Chemistry and Technology (REQUIMTE), Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, PortugalAssociated Laboratory for Green Chemistry (LAQV) of the Network of Chemistry and Technology (REQUIMTE), Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, PortugalAssociated Laboratory for Green Chemistry (LAQV) of the Network of Chemistry and Technology (REQUIMTE), Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, PortugalAssociated Laboratory for Green Chemistry (LAQV) of the Network of Chemistry and Technology (REQUIMTE), Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, PortugalAssociated Laboratory for Green Chemistry (LAQV) of the Network of Chemistry and Technology (REQUIMTE), Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, PortugalChemistry Centre, University of Minho (CQ-UM), Gualtar, 4710-057 Braga, PortugalChemistry Centre, University of Minho (CQ-UM), Gualtar, 4710-057 Braga, PortugalChemistry Centre, University of Minho (CQ-UM), Gualtar, 4710-057 Braga, PortugalAssociated Laboratory for Green Chemistry (LAQV) of the Network of Chemistry and Technology (REQUIMTE), Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, PortugalA set of procedures was developed for the simple synthesis of phytyl phenolipids, which resulted in high yields (70–95%) of phytyl esters of caffeic, protocatechuic, homoprotocatechuic, and dihydrocaffeic acids. Initial characterization revealed that these new compounds exhibited similar radical scavenging activity and liposolubility to α-tocopherol, a key antioxidant present in membranes. Cyclic voltammetry analysis indicated that the phytyl derivatives had lower anodic peak potentials compared to the original phenolic acids, with electron transfer following an adsorption-controlled mechanism. In phosphatidylcholine large unilamellar vesicles (LUVs), phytyl esters demonstrated remarkable efficiency in preventing liposome autoxidation when compared to α-tocopherol. Despite their strong radical scavenging capacity and membrane penetration ability, the antioxidant effectiveness of the phytyl esters in liposomes was influenced by the structure of their polyphenolic moiety. These new compounds are considered promising candidates for future pharmacological applications against oxidative stress in lipoproteins and cells, warranting further evaluation of their antioxidant and anti-inflammatory effects in cellular models and in vivo.https://www.mdpi.com/1420-3049/30/10/2193phenolic acidsphenolipidsphytyl estersliposomesbiomembranecaffeic acid |
| spellingShingle | Vânia Costa Marlene Costa Rute Rebelo Francisca Arques Mariana Ferreira Paula Gameiro Tomás Barros Dulce Geraldo Luís S. Monteiro Fátima Paiva-Martins Phytyl Phenolipids: Structurally Modified Antioxidants with Superior Lipid Membrane Interaction Molecules phenolic acids phenolipids phytyl esters liposomes biomembrane caffeic acid |
| title | Phytyl Phenolipids: Structurally Modified Antioxidants with Superior Lipid Membrane Interaction |
| title_full | Phytyl Phenolipids: Structurally Modified Antioxidants with Superior Lipid Membrane Interaction |
| title_fullStr | Phytyl Phenolipids: Structurally Modified Antioxidants with Superior Lipid Membrane Interaction |
| title_full_unstemmed | Phytyl Phenolipids: Structurally Modified Antioxidants with Superior Lipid Membrane Interaction |
| title_short | Phytyl Phenolipids: Structurally Modified Antioxidants with Superior Lipid Membrane Interaction |
| title_sort | phytyl phenolipids structurally modified antioxidants with superior lipid membrane interaction |
| topic | phenolic acids phenolipids phytyl esters liposomes biomembrane caffeic acid |
| url | https://www.mdpi.com/1420-3049/30/10/2193 |
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