Solid-state studies and antioxidant properties of the γ-cyclodextrin·fisetin inclusion compound

Pais, Joana; Barroca, Maria João; Marques, M. P. M.; Paz, Filipe A. Almeida; Braga, Susana S.

doi:10.3762/bjoc.13.212

Cited by 10 publications

(4 citation statements)

References 40 publications

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“…As described in the section referring to PXRD, γ-CD molecules pack, with the guest molecules lodged inside the channel cavity and also with the formation of wide inter-channel spaces that are able to retain a large number of water molecules (see inset in Figure 4). Literature examples of γ-CD complexes with a large number of hydration waters include γ-CD•quercetin•(H 2 O) 17 [29], γ-CD•fisetin•(H 2 O) 17 [30], and (γ-CD) 3 •(resveratrol) 4 •(H 2 O) 62 [31], to name only a few.…”

Section: Thermogravimetric Analysismentioning

confidence: 99%

Inclusion Compound of Efavirenz and γ-Cyclodextrin: Solid State Studies and Effect on Solubility

et al. 2021

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Efavirenz is an antiretroviral drug of widespread use in the management of infections with human immunodeficiency virus type 1 (HIV-1). Efavirenz is also used in paediatrics, but due to its very poor aqueous solubility the liquid formulations available resort to oil-based excipients. In this report we describe the interaction of γ-cyclodextrin with efavirenz in solution and in the solid state. In aqueous solution, the preferential host–guest stoichiometry was determined by the continuous variation method using 1H NMR, which indicated a 3:2 host-to-guest proportion. Following, the solid inclusion compound was prepared at different stoichiometries by co-dissolution and freeze-drying. Solid-state characterisation of the products using FT-IR, 13C{1H} CP-MAS NMR, thermogravimetry, and X-ray powder diffraction has confirmed that the 3:2 stoichiometry is the adequate starting condition to isolate a solid inclusion compound in the pure form. The effect of γ-cyclodextrin on the solubility of efavirenz is studied by the isotherm method.

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Section: Thermogravimetric Analysismentioning

confidence: 99%

Inclusion Compound of Efavirenz and γ-Cyclodextrin: Solid State Studies and Effect on Solubility

et al. 2021

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“…Note that, since cyclodextrin molecules may stack as dimers, a 1:1 proportion can correspond, in practical terms, to a 2:2 stoichiometry for the γ-CD•gingerols inclusion compound. Also noteworthy, the number of hydration water molecules per host unit is more than twice of that occurring in pure γ-CD heptahydrate, a feature that is typically associated with γ-CD inclusion compounds [41]. This is discussed with further detail in Section 3.2.2.…”

Section: Preparation and Characterisation Of γ-Cd•gingerolsmentioning

confidence: 94%

Solid γ-Cyclodextrin Inclusion Compound with Gingerols, a Multi-Component Guest: Preparation, Properties and Application in Yogurt

et al. 2020

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Gingerols from the rhizome of fresh ginger (Zingiber officinale) were obtained by a simple extraction, followed by purification. The gingerols extract was composed of 6-gingerol (54%), 8-gingerol (20%), and 10-gingerol (26%). It was included into γ-cyclodextrin by classic co-dissolution procedures. Solid-state characterisation of γ-cyclodextrin·gingerols shows that this inclusion compound features 1:1 host-to-guest stoichiometry and that it is a microcrystalline powder with a crystalline cell that belongs to the tetragonal space group 4212, having the host molecules stacked in infinite channels where the gingerols are accommodated. In chimico studies with ABTS•+ scavenging, NO• scavenging, β-carotene peroxidation, and 5-LOX inhibition show that γ-cyclodextrin is a suitable carrier for gingerols, because it does not alter their reactivity towards these substances. Yogurt was tested as a matrix for the incorporation of gingerols and γ-cyclodextrin·gingerols into foodstuff. The colour of the fortified yogurt suffered little alterations. In the case of yogurt with the inclusion compound, γ-cyclodextrin·gingerols, as fortificant, these alterations were not perceptible to the naked eye. Moreover, yogurt with γ-cyclodextrin·gingerols showed a good antioxidant activity, thus being suitable for use in nutraceutical applications.

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“…The ability to scavenge the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical was determined as previously described [73]. The DPPH radical was prepared in methanol in order to have a maximum absorption value at 515 nm in the 0.9-1.0 range.…”

Section: 2-diphenyl-1-picrylhydrazyl Radical Scavengingmentioning

confidence: 99%

Novel Insights into Corema album Berries: Vibrational Profile and Biological Activity

Marques

Martín

Amado

et al. 2021

Plants

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This study reports an evaluation of the biological properties of the edible berries from Corema album, an endemic shrub of the Portuguese coastline, aiming at its use as a nutraceutical. Different methanolic extracts were obtained from the pulp and seed of fresh berries: pulp extract, seed residue, and seed oil (extracted and characterized for the first time). For each of these, the antioxidant activity was assessed, by different methods, as well as the antimicrobial ability. Overall, the seeds were shown to be the most nutraceutical part of the berry since they showed higher antioxidant activity, while the pulp extract displayed a significant antimicrobial capacity against several clinically relevant bacterial strains. Furthermore, the extracts were fully characterized by complementary infrared and Raman spectroscopy, revealing the presence of phenolic acids, polysaccharides, sugars, and triterpenoids in the pulp, high content of unsaturated fatty acids in the seed oil, and significant amounts of phenolics and carotenoids in the seed residue. These results pave the way for a reliable correlation between chemical composition and biological activity, in edible fruit samples.

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Solid-state studies and antioxidant properties of the γ-cyclodextrin·fisetin inclusion compound

Cited by 10 publications

References 40 publications

Inclusion Compound of Efavirenz and γ-Cyclodextrin: Solid State Studies and Effect on Solubility

Inclusion Compound of Efavirenz and γ-Cyclodextrin: Solid State Studies and Effect on Solubility

Solid γ-Cyclodextrin Inclusion Compound with Gingerols, a Multi-Component Guest: Preparation, Properties and Application in Yogurt

Novel Insights into Corema album Berries: Vibrational Profile and Biological Activity

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