Systematic investigation and molecular modelling of complexation between several groups of flavonoids and HP-β-cyclodextrins
Flavonoids play an important role in the food and pharmaceutical industries and its molecular structure is responsible for their bioavailability and activity. Their very low water-solubility reduces their bioavailability. HP-β-cyclodextrins have been used to improve this parameter. Our results permi...
| Main Authors: | , , , , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2017-09-01
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| Series: | Journal of Functional Foods |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1756464617303687 |
| _version_ | 1819044282860830720 |
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| author | Maravillas Pérez-Abril Carmen Lucas-Abellán Julián Castillo-Sánchez Horacio Pérez-Sánchez José P. Cerón-Carrasco Isabel Fortea José A. Gabaldón Estrella Núñez-Delicado |
| author_facet | Maravillas Pérez-Abril Carmen Lucas-Abellán Julián Castillo-Sánchez Horacio Pérez-Sánchez José P. Cerón-Carrasco Isabel Fortea José A. Gabaldón Estrella Núñez-Delicado |
| author_sort | Maravillas Pérez-Abril |
| collection | DOAJ |
| description | Flavonoids play an important role in the food and pharmaceutical industries and its molecular structure is responsible for their bioavailability and activity. Their very low water-solubility reduces their bioavailability. HP-β-cyclodextrins have been used to improve this parameter. Our results permit a better understanding of the influence of flavonoid molecular skeletons on the cyclodextrin complexation process. Molecular docking analysis showed that the most stable complex with HP-β-CD is that formed by kaempferol, being its stability mainly due to the hydrogen bonds network established between oxygen at positions 3, 4, 5 and 7 and to the hydrophobic stabilization of its aromatic scaffold within the inner cavity of HP-β-CD. The highest relative effect of the different substructures on inclusion efficacy is, primarily, the result of the conjugation between three elements on the flavonoid C-ring: the carbonyl group in C-4 position, the double bond C2C3 and the hydroxyl group in C-3 position. |
| first_indexed | 2024-12-21T10:10:12Z |
| format | Article |
| id | doaj.art-37f0d2df8ab84835907ac9eee6485d43 |
| institution | Directory Open Access Journal |
| issn | 1756-4646 |
| language | English |
| last_indexed | 2024-12-21T10:10:12Z |
| publishDate | 2017-09-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Functional Foods |
| spelling | doaj.art-37f0d2df8ab84835907ac9eee6485d432022-12-21T19:07:44ZengElsevierJournal of Functional Foods1756-46462017-09-0136122131Systematic investigation and molecular modelling of complexation between several groups of flavonoids and HP-β-cyclodextrinsMaravillas Pérez-Abril0Carmen Lucas-Abellán1Julián Castillo-Sánchez2Horacio Pérez-Sánchez3José P. Cerón-Carrasco4Isabel Fortea5José A. Gabaldón6Estrella Núñez-Delicado7Dpto. Tecnología de la Alimentación y Nutrición, Universidad Católica San Antonio de Murcia (UCAM), Campus de los Jerónimos, N° 135 Guadalupe, 30107 Murcia, SpainDpto. Tecnología de la Alimentación y Nutrición, Universidad Católica San Antonio de Murcia (UCAM), Campus de los Jerónimos, N° 135 Guadalupe, 30107 Murcia, SpainDpto. Tecnología de la Alimentación y Nutrición, Universidad Católica San Antonio de Murcia (UCAM), Campus de los Jerónimos, N° 135 Guadalupe, 30107 Murcia, Spain; Research & Development Department, Nutrafur S.A., Grupo-Frutarom, 30820 Alcantarilla, Murcia, SpainBioinformatics and High Performance Computing Research Group (BIO-HPC), Dpto. Ciencias Politécnicas, Universidad Católica San Antonio de Murcia (UCAM), Campus de los Jerónimos, N° 135 Guadalupe, 30107 Murcia, SpainBioinformatics and High Performance Computing Research Group (BIO-HPC), Dpto. Ciencias Politécnicas, Universidad Católica San Antonio de Murcia (UCAM), Campus de los Jerónimos, N° 135 Guadalupe, 30107 Murcia, SpainDpto. Tecnología de la Alimentación y Nutrición, Universidad Católica San Antonio de Murcia (UCAM), Campus de los Jerónimos, N° 135 Guadalupe, 30107 Murcia, SpainDpto. Tecnología de la Alimentación y Nutrición, Universidad Católica San Antonio de Murcia (UCAM), Campus de los Jerónimos, N° 135 Guadalupe, 30107 Murcia, SpainDpto. Tecnología de la Alimentación y Nutrición, Universidad Católica San Antonio de Murcia (UCAM), Campus de los Jerónimos, N° 135 Guadalupe, 30107 Murcia, Spain; Corresponding author.Flavonoids play an important role in the food and pharmaceutical industries and its molecular structure is responsible for their bioavailability and activity. Their very low water-solubility reduces their bioavailability. HP-β-cyclodextrins have been used to improve this parameter. Our results permit a better understanding of the influence of flavonoid molecular skeletons on the cyclodextrin complexation process. Molecular docking analysis showed that the most stable complex with HP-β-CD is that formed by kaempferol, being its stability mainly due to the hydrogen bonds network established between oxygen at positions 3, 4, 5 and 7 and to the hydrophobic stabilization of its aromatic scaffold within the inner cavity of HP-β-CD. The highest relative effect of the different substructures on inclusion efficacy is, primarily, the result of the conjugation between three elements on the flavonoid C-ring: the carbonyl group in C-4 position, the double bond C2C3 and the hydroxyl group in C-3 position.http://www.sciencedirect.com/science/article/pii/S1756464617303687CyclodextrinFlavonoidInclusion complexMicroencapsulationMolecular modelling |
| spellingShingle | Maravillas Pérez-Abril Carmen Lucas-Abellán Julián Castillo-Sánchez Horacio Pérez-Sánchez José P. Cerón-Carrasco Isabel Fortea José A. Gabaldón Estrella Núñez-Delicado Systematic investigation and molecular modelling of complexation between several groups of flavonoids and HP-β-cyclodextrins Journal of Functional Foods Cyclodextrin Flavonoid Inclusion complex Microencapsulation Molecular modelling |
| title | Systematic investigation and molecular modelling of complexation between several groups of flavonoids and HP-β-cyclodextrins |
| title_full | Systematic investigation and molecular modelling of complexation between several groups of flavonoids and HP-β-cyclodextrins |
| title_fullStr | Systematic investigation and molecular modelling of complexation between several groups of flavonoids and HP-β-cyclodextrins |
| title_full_unstemmed | Systematic investigation and molecular modelling of complexation between several groups of flavonoids and HP-β-cyclodextrins |
| title_short | Systematic investigation and molecular modelling of complexation between several groups of flavonoids and HP-β-cyclodextrins |
| title_sort | systematic investigation and molecular modelling of complexation between several groups of flavonoids and hp β cyclodextrins |
| topic | Cyclodextrin Flavonoid Inclusion complex Microencapsulation Molecular modelling |
| url | http://www.sciencedirect.com/science/article/pii/S1756464617303687 |
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