Formation of inclusion compounds of (+)catechin with β-cyclodextrin in different complexation media: Spectral, thermal and antioxidant properties

Valarini, Osvaldo; Dantas, João Henrique; Barão, Carlos Eduardo; Zanoelo, Éverton Fernando; Cardozo‐Filho, Lúcio; Moraes, Flávio Faria de

doi:10.1016/j.supflu.2016.06.005

Cited by 21 publications

(12 citation statements)

References 42 publications

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“…2a) is characterized by an endothermic peak at 191 °C associated to its melting with decomposition. On the contrary, as already reported by Junior et al. (2017) and Ferreira-Nunes et al.…”

Section: Resultssupporting

confidence: 47%

Synthesis and characterization of a (+)-catechin and L-(+)-ascorbic acid cocrystal as a new functional ingredient for tea drinks

Spizzirri

Carullo

Cicco

et al. 2019

Heliyon

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Tea (Camellia Sinensis) is one of the most popular drink, consumed as infusion or bottled ready to drink beverages. Although tea leaves contain many antioxidants compounds, after processing they can drastically decrease, sometimes up to a full degradation, as in the case of catechin, a very healthy flavan-3-ol. In this context, the synthesis of a cocrystal between (þ)-catechin and L-(þ)-ascorbic acid, was proved to be a useful strategy to make a new ingredient able to ameliorate the antioxidant profile of both infusions and bottled teas. The obtained cocrystal showed a threefold higher solubility than (þ)catechin and its formation was elucidated unambiguously by FT-IR, thermal (DSC) and diffraction (PXRD) analyses. Antioxidant characteristics of the samples were evaluated by colorimetric assays. As expected, infusions showed much better antioxidant features than ready-to-use lemon and peach teas. The same trend was confirmed after the addition of the cocrystal at two concentration levels. In particular, supplementation at concentration of 2 mg mL À1 improved the bottled tea antioxidant values to the level showed by the not-added infusion tea.

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“…2a) is characterized by an endothermic peak at 191 °C associated to its melting with decomposition. On the contrary, as already reported by Junior et al. (2017) and Ferreira-Nunes et al.…”

Section: Resultssupporting

confidence: 47%

Synthesis and characterization of a (+)-catechin and L-(+)-ascorbic acid cocrystal as a new functional ingredient for tea drinks

Spizzirri

Carullo

Cicco

et al. 2019

Heliyon

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“…Flavonoid is a class of phytogenic polyphenolic compounds, including in many kinds of human diet, and has various physicochemical characters and chemical structures. The high-resolution mass spectrometry and NMR results revealed the presence of catechin in the roots of A. unedo extract, and these results are similar to those which were conducted by Junior et al [ 22 ].…”

Section: Discussionsupporting

confidence: 88%

“…The 1 H NMR (300 MHz) and 13 C NMR (75 MHz) spectra were recorded on Bruker spectrometer with chemical shift values (δ) given in part per million (ppm) relative to TMS (0.00 ppm) and using MeOD as a solvent, the coupling constants (J) are expressed in hertz (Hz) and singlet (s), doublet (d), and doublet of a doublet (dd) as well as the multiplet (m). The high-resolution mass spectra (HRMS) analysis was performed in a negative mode in full mass scan ( m/z 100 to 600 amu) using a Thermo Scientific Orbitrap Mass Spectrometer Exactive equipped with a heated electrospray ionization source (HESI), and the used resolution was 1000 [ 22 , 33 ].…”

Section: Methodsmentioning

confidence: 99%

Separation, Identification, and Antidiabetic Activity of Catechin Isolated from Arbutus unedo L. Plant Roots

Mrabti

Jaradat

Fichtali

et al. 2018

Plants

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Phytopharmaceuticals play an essential role in medicine, since the need to investigate highly effective and safe drugs for the treatment of diabetes mellitus disease remains a significant challenge for modern medicine. Arbutus unedo L. root has various therapeutic properties, and has been used widely in the traditional medicine as an antidiabetic agent. The current study aimed to isolate the pharmacologically active compound from A. unedo roots using accelerated solvent extraction technology, to determine its chemical structure using different instrumental analytical methods, and also to evaluate the α-glucosidase inhibitory activity. The roots of A. unedo were exhaustively extracted by high-pressure static extraction using the Zippertex® technology (Dionex-ASE, Paris, France), and the extract was mixed with XAD-16 resin to reach quantifiable amounts of active compounds which were identified by high-pressure liquid chromatography (HPLC), 1H NMR (300 MHz), and 13C NMR. The antidiabetic activity of the isolated compound was evaluated using the α-glucosidase inhibitory assay. The active compound was isolated, and its structure was identified as catechin using instrumental analysis.The results revealed that the isolated compound has potential α-glucosidase inhibitory activity with an IC50 value of 87.55 ± 2.23 μg/mL greater than acarbose. This was used as a positive control, which has an IC50 value of 199.53 ± 1.12 μg/mL. According to the results achieved, the roots of A. unedo were considered the best source of catechin and the Zippertex® technology method of extraction is the best method for isolation of this therapeutic active compound. In addition, the α-glucosidase inhibitory activity results confirmed the traditional use of A. unedo roots as an antidiabetic agent. Future clinical trials and investigations of antidiabetic and other pharmacological effects such as anticancer are required.

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“…Examples of successful applications of the use of cyclodextrins include encapsulation substrates such as drugs, food products, and natural pesticides [ 2 , 3 , 4 , 5 , 6 , 7 ]. The synthesis of β-cyclodextrin inclusion complexes can be accomplished through methods such as co-precipitation [ 8 , 9 ], kneading [ 10 , 11 ], ultrasonication [ 12 , 13 ], freeze-drying [ 14 ], spray-drying [ 15 ], and the use of supercritical fluids [ 16 ]. Synthetic methods currently available are simple, require no (or limited amount of) organic solvents and no additional purification or cleanup steps, and use non-toxic materials, which makes the preparation of β-cyclodextrin inclusion complexes a desired and environmentally friendly process that falls into the green-synthesis approach [ 17 , 18 ].…”

Section: Introductionmentioning

confidence: 99%

Novel β-Cyclodextrin and Catnip Essential Oil Inclusion Complex and Its Tick Repellent Properties

2021

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Cyclodextrin inclusion complexes have been successfully used to encapsulate essential oils, improving their physicochemical properties and pharmacological effects. Besides being well-known for its effects on cats and other felines, catnip (Nepeta cataria) essential oil demonstrates repellency against blood-feeding pests such as mosquitoes. This study evaluates the tick repellency of catnip oil alone and encapsulated in β-cyclodextrin, prepared using the co-precipitation method at a 1:1 molar ratio. The physicochemical properties of this inclusion complex were characterized using GC-FID for encapsulation efficiency and yield and SPME/GC-MS for volatile emission. Qualitative assessment of complex formation was done by UV-Vis, FT-IR, 1H NMR, and SEM analyses. Catnip oil at 5% (v/v) demonstrated significant tick repellency over time, being comparable to DEET as used in commercial products. The prepared [catnip: β-CD] inclusion complex exerted significant tick repellency at lower concentration of the essential oil (equivalent of 1% v/v). The inclusion complex showed that the release of the active ingredient was consistent after 6 h, which could improve the effective repellent duration. These results demonstrated the effective tick repellent activity of catnip essential oil and the successful synthesis of the inclusion complex, suggesting that β-CDs are promising carriers to improve catnip oil properties and to expand its use in repellent formulations for tick management.

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Formation of inclusion compounds of (+)catechin with β-cyclodextrin in different complexation media: Spectral, thermal and antioxidant properties

Cited by 21 publications

References 42 publications

Synthesis and characterization of a (+)-catechin and L-(+)-ascorbic acid cocrystal as a new functional ingredient for tea drinks

Synthesis and characterization of a (+)-catechin and L-(+)-ascorbic acid cocrystal as a new functional ingredient for tea drinks

Separation, Identification, and Antidiabetic Activity of Catechin Isolated from Arbutus unedo L. Plant Roots

Novel β-Cyclodextrin and Catnip Essential Oil Inclusion Complex and Its Tick Repellent Properties

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