Glycerol as Alternative Co-Solvent for Water Extraction of Polyphenols from <i>Carménère</i> Pomace: Hot Pressurized Liquid Extraction and Computational Chemistry Calculations
Glycerol is a co-solvent for water extraction that has been shown to be highly effective for obtaining polyphenol extracts under atmospheric conditions. However, its efficacy under subcritical conditions has not yet been studied. We assessed different water-glycerol mixtures (15%, 32.5%, and 50%) in...
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MDPI AG
2020-03-01
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| Series: | Biomolecules |
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| Online Access: | https://www.mdpi.com/2218-273X/10/3/474 |
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| author | Nils Leander Huamán-Castilla María Salomé Mariotti-Celis Maximiliano Martínez-Cifuentes José Ricardo Pérez-Correa |
| author_facet | Nils Leander Huamán-Castilla María Salomé Mariotti-Celis Maximiliano Martínez-Cifuentes José Ricardo Pérez-Correa |
| author_sort | Nils Leander Huamán-Castilla |
| collection | DOAJ |
| description | Glycerol is a co-solvent for water extraction that has been shown to be highly effective for obtaining polyphenol extracts under atmospheric conditions. However, its efficacy under subcritical conditions has not yet been studied. We assessed different water-glycerol mixtures (15%, 32.5%, and 50%) in a hot pressurized liquid extraction system (HPLE: 10 MPa) at 90 °C, 120 °C, and 150 °C to obtain extracts of low molecular weight polyphenols from <i>Carménère</i> grape pomace. Under the same extraction conditions, glycerol as a co-solvent achieved significantly higher yields in polyphenols than ethanol. Optimal extraction conditions were 150 °C, with 32.5% glycerol for flavonols and 50% for flavanols, stilbenes, and phenolic acids. Considering gallic acid as a model molecule, computational chemistry calculations were applied to explain some unusual extraction outcomes. Furthermore, glycerol, methanol, ethanol, and ethylene glycol were studied to establish an incipient structure−property relationship. The high extraction yields of gallic acid obtained with water and glycerol solvent mixtures can be explained not only by the additional hydrogen bonds between glycerol and gallic acid as compared with the other alcohols, but also because the third hydroxyl group allows the formation of a three-centered hydrogen bond, which intensifies the strongest glycerol and gallic acid hydrogen bond. The above occurs both in neutral and deprotonated gallic acid. Consequently, glycerol confers to the extraction solvent a higher solvation energy of polyphenols than ethanol. |
| first_indexed | 2024-04-12T03:51:17Z |
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| id | doaj.art-eacb1e4c99ba48f9a3cd07791fa2ee11 |
| institution | Directory Open Access Journal |
| issn | 2218-273X |
| language | English |
| last_indexed | 2024-04-12T03:51:17Z |
| publishDate | 2020-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Biomolecules |
| spelling | doaj.art-eacb1e4c99ba48f9a3cd07791fa2ee112022-12-22T03:48:58ZengMDPI AGBiomolecules2218-273X2020-03-0110347410.3390/biom10030474biom10030474Glycerol as Alternative Co-Solvent for Water Extraction of Polyphenols from <i>Carménère</i> Pomace: Hot Pressurized Liquid Extraction and Computational Chemistry CalculationsNils Leander Huamán-Castilla0María Salomé Mariotti-Celis1Maximiliano Martínez-Cifuentes2José Ricardo Pérez-Correa3Chemical and Bioprocess Engineering Department, School of Engineering, Pontificia Universidad Católica de Chile, Vicuña Mackenna 4860, P.O. Box 306, Santiago 7820436, ChilePrograma Institucional de Fomento a la Investigación, Desarrollo e Innovación, Universidad Tecnológica Metropolitana, Ignacio Valdivieso 2409, P.O. Box 9845, Santiago 8940577, ChileCentro Integrativo de Biología y Química Aplicada (CIBQA), Escuela de Tecnología Médica, Facultad de Ciencias de la Salud, Universidad Bernardo O’Higgins, General Gana 1702, Santiago 8370993, ChileChemical and Bioprocess Engineering Department, School of Engineering, Pontificia Universidad Católica de Chile, Vicuña Mackenna 4860, P.O. Box 306, Santiago 7820436, ChileGlycerol is a co-solvent for water extraction that has been shown to be highly effective for obtaining polyphenol extracts under atmospheric conditions. However, its efficacy under subcritical conditions has not yet been studied. We assessed different water-glycerol mixtures (15%, 32.5%, and 50%) in a hot pressurized liquid extraction system (HPLE: 10 MPa) at 90 °C, 120 °C, and 150 °C to obtain extracts of low molecular weight polyphenols from <i>Carménère</i> grape pomace. Under the same extraction conditions, glycerol as a co-solvent achieved significantly higher yields in polyphenols than ethanol. Optimal extraction conditions were 150 °C, with 32.5% glycerol for flavonols and 50% for flavanols, stilbenes, and phenolic acids. Considering gallic acid as a model molecule, computational chemistry calculations were applied to explain some unusual extraction outcomes. Furthermore, glycerol, methanol, ethanol, and ethylene glycol were studied to establish an incipient structure−property relationship. The high extraction yields of gallic acid obtained with water and glycerol solvent mixtures can be explained not only by the additional hydrogen bonds between glycerol and gallic acid as compared with the other alcohols, but also because the third hydroxyl group allows the formation of a three-centered hydrogen bond, which intensifies the strongest glycerol and gallic acid hydrogen bond. The above occurs both in neutral and deprotonated gallic acid. Consequently, glycerol confers to the extraction solvent a higher solvation energy of polyphenols than ethanol.https://www.mdpi.com/2218-273X/10/3/474polyphenolsglycerolhot pressurized liquid extractionhydrogen bondquantum chemical calculations |
| spellingShingle | Nils Leander Huamán-Castilla María Salomé Mariotti-Celis Maximiliano Martínez-Cifuentes José Ricardo Pérez-Correa Glycerol as Alternative Co-Solvent for Water Extraction of Polyphenols from <i>Carménère</i> Pomace: Hot Pressurized Liquid Extraction and Computational Chemistry Calculations Biomolecules polyphenols glycerol hot pressurized liquid extraction hydrogen bond quantum chemical calculations |
| title | Glycerol as Alternative Co-Solvent for Water Extraction of Polyphenols from <i>Carménère</i> Pomace: Hot Pressurized Liquid Extraction and Computational Chemistry Calculations |
| title_full | Glycerol as Alternative Co-Solvent for Water Extraction of Polyphenols from <i>Carménère</i> Pomace: Hot Pressurized Liquid Extraction and Computational Chemistry Calculations |
| title_fullStr | Glycerol as Alternative Co-Solvent for Water Extraction of Polyphenols from <i>Carménère</i> Pomace: Hot Pressurized Liquid Extraction and Computational Chemistry Calculations |
| title_full_unstemmed | Glycerol as Alternative Co-Solvent for Water Extraction of Polyphenols from <i>Carménère</i> Pomace: Hot Pressurized Liquid Extraction and Computational Chemistry Calculations |
| title_short | Glycerol as Alternative Co-Solvent for Water Extraction of Polyphenols from <i>Carménère</i> Pomace: Hot Pressurized Liquid Extraction and Computational Chemistry Calculations |
| title_sort | glycerol as alternative co solvent for water extraction of polyphenols from i carmenere i pomace hot pressurized liquid extraction and computational chemistry calculations |
| topic | polyphenols glycerol hot pressurized liquid extraction hydrogen bond quantum chemical calculations |
| url | https://www.mdpi.com/2218-273X/10/3/474 |
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