γ-Cyclodextrin Inclusion of Phloroglucinol: Solid State Studies and Antioxidant Activity throughout the Digestive Tract
Phloroglucinol is a powerful antioxidant compound and an active pharmaceutical ingredient used in the management of intestinal spasms. In this report, we describe the interaction of γ-cyclodextrin with phloroglucinol to readily form a solid inclusion compound with 1:1 by co-dissolution and freeze-dr...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-02-01
|
| Series: | Applied Sciences |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2076-3417/12/5/2340 |
| _version_ | 1827652009709273088 |
|---|---|
| author | Marcelo D. Catarino Beatriz S. Baía Costa Ana Rita Circuncisão Artur M. S. Silva Susana M. Cardoso Susana Santos Braga |
| author_facet | Marcelo D. Catarino Beatriz S. Baía Costa Ana Rita Circuncisão Artur M. S. Silva Susana M. Cardoso Susana Santos Braga |
| author_sort | Marcelo D. Catarino |
| collection | DOAJ |
| description | Phloroglucinol is a powerful antioxidant compound and an active pharmaceutical ingredient used in the management of intestinal spasms. In this report, we describe the interaction of γ-cyclodextrin with phloroglucinol to readily form a solid inclusion compound with 1:1 by co-dissolution and freeze-drying. Solid-state characterisation using FT-IR, thermal analyses (TGA and DTA) and X-ray powder diffraction confirmed the formation of a true inclusion compound (γ-CD·PG) in which the molecules of γ-CD are stacked into channels. This spatial arrangement is typical of γ-CD inclusion compounds, and it allows for the guest molecules to be located inside these channels. The evaluation of the antiradical potential of γ-CD·PG (against O<sub>2</sub><sup>•</sup>− and NO<sup>•</sup>) on different steps of the digestive process (mouth, gastric and intestinal phases) led us to conclude that the inclusion of phloroglucinol promoted better antioxidant activity at the end of the digestion when compared to the free phloroglucinol. |
| first_indexed | 2024-03-09T20:48:32Z |
| format | Article |
| id | doaj.art-4edc07efb5454440839de7e1eabd46a2 |
| institution | Directory Open Access Journal |
| issn | 2076-3417 |
| language | English |
| last_indexed | 2024-03-09T20:48:32Z |
| publishDate | 2022-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Applied Sciences |
| spelling | doaj.art-4edc07efb5454440839de7e1eabd46a22023-11-23T22:39:13ZengMDPI AGApplied Sciences2076-34172022-02-01125234010.3390/app12052340γ-Cyclodextrin Inclusion of Phloroglucinol: Solid State Studies and Antioxidant Activity throughout the Digestive TractMarcelo D. Catarino0Beatriz S. Baía Costa1Ana Rita Circuncisão2Artur M. S. Silva3Susana M. Cardoso4Susana Santos Braga5LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, PortugalLAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, PortugalLAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, PortugalLAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, PortugalLAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, PortugalLAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, PortugalPhloroglucinol is a powerful antioxidant compound and an active pharmaceutical ingredient used in the management of intestinal spasms. In this report, we describe the interaction of γ-cyclodextrin with phloroglucinol to readily form a solid inclusion compound with 1:1 by co-dissolution and freeze-drying. Solid-state characterisation using FT-IR, thermal analyses (TGA and DTA) and X-ray powder diffraction confirmed the formation of a true inclusion compound (γ-CD·PG) in which the molecules of γ-CD are stacked into channels. This spatial arrangement is typical of γ-CD inclusion compounds, and it allows for the guest molecules to be located inside these channels. The evaluation of the antiradical potential of γ-CD·PG (against O<sub>2</sub><sup>•</sup>− and NO<sup>•</sup>) on different steps of the digestive process (mouth, gastric and intestinal phases) led us to conclude that the inclusion of phloroglucinol promoted better antioxidant activity at the end of the digestion when compared to the free phloroglucinol.https://www.mdpi.com/2076-3417/12/5/2340cyclodextrin inclusionsolid statepolyphenolantioxidantgastrointestinal tractphloroglucinol |
| spellingShingle | Marcelo D. Catarino Beatriz S. Baía Costa Ana Rita Circuncisão Artur M. S. Silva Susana M. Cardoso Susana Santos Braga γ-Cyclodextrin Inclusion of Phloroglucinol: Solid State Studies and Antioxidant Activity throughout the Digestive Tract Applied Sciences cyclodextrin inclusion solid state polyphenol antioxidant gastrointestinal tract phloroglucinol |
| title | γ-Cyclodextrin Inclusion of Phloroglucinol: Solid State Studies and Antioxidant Activity throughout the Digestive Tract |
| title_full | γ-Cyclodextrin Inclusion of Phloroglucinol: Solid State Studies and Antioxidant Activity throughout the Digestive Tract |
| title_fullStr | γ-Cyclodextrin Inclusion of Phloroglucinol: Solid State Studies and Antioxidant Activity throughout the Digestive Tract |
| title_full_unstemmed | γ-Cyclodextrin Inclusion of Phloroglucinol: Solid State Studies and Antioxidant Activity throughout the Digestive Tract |
| title_short | γ-Cyclodextrin Inclusion of Phloroglucinol: Solid State Studies and Antioxidant Activity throughout the Digestive Tract |
| title_sort | γ cyclodextrin inclusion of phloroglucinol solid state studies and antioxidant activity throughout the digestive tract |
| topic | cyclodextrin inclusion solid state polyphenol antioxidant gastrointestinal tract phloroglucinol |
| url | https://www.mdpi.com/2076-3417/12/5/2340 |
| work_keys_str_mv | AT marcelodcatarino gcyclodextrininclusionofphloroglucinolsolidstatestudiesandantioxidantactivitythroughoutthedigestivetract AT beatrizsbaiacosta gcyclodextrininclusionofphloroglucinolsolidstatestudiesandantioxidantactivitythroughoutthedigestivetract AT anaritacircuncisao gcyclodextrininclusionofphloroglucinolsolidstatestudiesandantioxidantactivitythroughoutthedigestivetract AT arturmssilva gcyclodextrininclusionofphloroglucinolsolidstatestudiesandantioxidantactivitythroughoutthedigestivetract AT susanamcardoso gcyclodextrininclusionofphloroglucinolsolidstatestudiesandantioxidantactivitythroughoutthedigestivetract AT susanasantosbraga gcyclodextrininclusionofphloroglucinolsolidstatestudiesandantioxidantactivitythroughoutthedigestivetract |