Complexation of rosmarinic acid with hydroxypropyl-β-cyclodextrin and methyl-β-cyclodextrin: Formation of 2:1 complexes with improved antioxidant activity
| Autor: | Letícia Scherer Koester, Kleyton Santos Veras, Helder Ferreira Teixeira, Flávia Nathiely Silveira Fachel, Thiago Barcellos, Valquiria Linck Bassani, Amélia T. Henriques, Maria Gabriele Delagustin |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Cyclodextrin 010405 organic chemistry DPPH Rosmarinic acid Electrospray ionization Organic Chemistry Infrared spectroscopy 010402 general chemistry 01 natural sciences 0104 chemical sciences Analytical Chemistry Inorganic Chemistry chemistry.chemical_compound Differential scanning calorimetry chemistry Stability constants of complexes Solubility Spectroscopy Nuclear chemistry |
| Zdroj: | Journal of Molecular Structure. 1195:582-590 |
| ISSN: | 0022-2860 |
| Popis: | Rosmarinic acid (RA) is a phenolic compound with remarkable antioxidant activity; however it presents low bioavailability. Cyclodextrin (CD) derivatives, such as hydroxypropyl-β-CD (HPβCD) and methyl-β-CD (MβCD), have been used to solve the low bioavailability of drugs, increasing their solubility or permeability. The aim of the present study was to investigate the complexation of RA with two derivative CDs, HPβCD and MβCD, and the resulting antioxidant activity. A phase-solubility study was performed to determine the stoichiometric ratio and apparent stability constant, and electrospray ionization coupled to mass spectroscopy (ESI–MS) was used to confirm the stoichiometric ratio. The freeze-dried (FD) complexes were characterized by liquid chromatography (LC), differential scanning calorimetry (DSC), Fourier-transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), and nuclear magnetic resonance (NMR). The antioxidant activity of RA and the FD complexes was evaluated by the DPPH method. A 2:1 (RA:CD) stoichiometric ratio and strong apparent constant stability were found for both complexes using a phase-solubility study, and ESI-MS spectra confirmed a signal corresponding to the 2:1 complex. The FD complexes showed high yield and RA content. The results of DSC, FTIR and SEM demonstrate changes in the physical-chemical characteristics of RA, suggesting its interaction with CDs. These interactions were confirmed by NMR, which revealed the formation of inclusion and non-inclusion complexes. The antioxidant activity of the RA:HPβCD and RA:MβCD FD complexes were higher than that of RA. The results suggest that FD complexes can be a technological approach to the development of formulations containing high content of RA with a view to increasing antioxidant potential. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect