Effect of temperature, pH, β- and HP-β-cds on the solubility and stability of flavanones: Naringenin and hesperetin

Lucas-Abellán, Carmen; Pérez-Abril, Maravillas; Castillo, Juan P.; Serrano, Antonio Martínez; Mercader, M.T.; Fortea, María Isabel; Gabaldón, José Antonio; Núñez-Delicado, Estrella

doi:10.1016/j.lwt.2019.03.059

Cited by 32 publications

(28 citation statements)

References 27 publications

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“…As far as an impact of pH conditions on solubility are concerned, it can be observed that in a more basic environment (phosphate buffer pH 6.8), tested compounds are more soluble than in acidic media. This can be related to weak acid character of flavanones and the fact of dissociation in basic medium [ 26 , 47 ].…”

Section: Resultsmentioning

confidence: 99%

“…Lucas–Abellan et al prepared Het complexes with β- and HP-β-CD, which was linked to improved solubility by 30- and 467-fold, respectively. They also indicated that pH value has an impact on complexation, wherein the strongest complexes of Het were formed at pH 6.5, at which Het has the protonated form [ 26 ]. So far, cyclodextrins have helped to improve the solubility of several polyphenols such as caffeic acid [ 27 ], ellagic acid [ 28 ], quercetin [ 29 , 30 ], rutin [ 30 ], resveratrol [ 31 ], and myricetin [ 1 ].…”

Section: Introductionmentioning

confidence: 99%

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Amorphous Inclusion Complexes: Molecular Interactions of Hesperidin and Hesperetin with HP-Β-CD and Their Biological Effects

Wdowiak

Rosiak

Tykarska

et al. 2022

IJMS

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This study aimed at obtaining hesperidin (Hed) and hesperetin (Het) systems with HP-β-CD by means of the solvent evaporation method. The produced systems were identified using infrared spectroscopy (FT-IR), X-ray powder diffraction (XRPD), and differential scanning calorimetry (DSC). Moreover, in silico docking and molecular dynamics studies were performed to assess the most preferable site of interactions between tested compounds and HP-β-CD. The changes of physicochemical properties (solubility, dissolution rate, and permeability) were determined chromatographically. The impact of modification on biological activity was tested in an antioxidant study as well as with regards to inhibition of enzymes important in pathogenesis of neurodegenerative diseases. The results indicated improvement in solubility over 1000 and 2000 times for Hed and Het, respectively. Permeability studies revealed that Hed has difficulties in crossing biological membranes, in contrast with Het, which can be considered to be well absorbed. The improved physicochemical properties influenced the biological activity in a positive manner by the increase in inhibitory activity on the DPPH radical and cholinoesterases. To conclude the use of HP-β-CD as a carrier in the formation of an amorphous inclusion complex seems to be a promising approach to improve the biological activity and bioavailability of Hed and Het.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Amorphous Inclusion Complexes: Molecular Interactions of Hesperidin and Hesperetin with HP-Β-CD and Their Biological Effects

Wdowiak

Rosiak

Tykarska

et al. 2022

IJMS

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“…Their health-promoting features have been explored in vivo and in vitro models, such as antioxidant activity [ 2 , 3 ], anti-inflammatory activity [ 4 , 5 ], anticancer activity [ 6 , 7 ], anti-diabetic activity [ 8 ] and protective effects on the central nervous system [ 9 ] and the cardiovascular system [ 10 ]. However, naringenin and naringin are hydrophobic and low-soluble polyphenols with low water solubility of 38 and 500 µg/mL at room temperature, respectively [ 11 , 12 ], and taste bitter, which greatly limits their application in clinical and functional foods. To overcome these limits, the solubility and bioavailability of naringenin and naringin have been improved by encapsulation in various kinds of carefully designed colloidal delivery systems, including cyclodextrins complexation [ 12 ], nanovehicles [ 13 , 14 ], liposomal [ 15 ] and ternary complex particles [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

Encapsulation of Hydrophobic and Low-Soluble Polyphenols into Nanoliposomes by pH-Driven Method: Naringenin and Naringin as Model Compounds

Chen

Gao

et al. 2021

Foods

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Naringenin and naringin are a class of hydrophobic polyphenol compounds and both have several biological activities containing antioxidant, anti-inflammatory and anti-tumor properties. Nevertheless, they have low water solubility and bioavailability, which limits their biological activity. In this study, an easy pH-driven method was applied to load naringenin or naringin into nanoliposomes based on the gradual reduction in their water solubility after the pH changed to acidity. Thus, the naringenin or naringin can be embedded into the hydrophobic region within nanoliposomes from the aqueous phase. A series of naringenin/naringin-loaded nanoliposomes with different pH values, lecithin contents and feeding naringenin/naringin concentrations were prepared by microfluidization and a pH-driven method. The naringin-loaded nanoliposome contained some free naringin due to its higher water solubility at lower pH values and had a relatively low encapsulation efficiency. However, the naringenin-loaded nanoliposomes were predominantly nanometric (44.95–104.4 nm), negatively charged (−14.1 to −19.3 mV) and exhibited relatively high encapsulation efficiency (EE = 95.34% for 0.75 mg/mL naringenin within 1% w/v lecithin). Additionally, the naringenin-loaded nanoliposomes still maintained good stability during 31 days of storage at 4 °C. This study may help to develop novel food-grade colloidal delivery systems and apply them to introducing naringenin or other lipophilic polyphenols into foods, supplements or drugs.

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“…Compared to the digested PPE sample, pectolinaringenin content was approximately 2.8 times higher in the primary digested sample of P-liposomes. This situation may be explained by the fact that poor water solubility of pectolinaringenin increases by increasing pH up 8.5 ( Lucas-Abellán et al., 2019 ). Naringenin, a derivative of pectolinaringenin, was reported to be the most efficiently encapsulated with β-cyclodextrin at pH 8.5.…”

Section: Resultsmentioning

confidence: 99%

Liposomal nanodelivery systems generated from proliposomes for pollen extract with improved solubility and in vitro bioaccessibility

Hızır-Kadı

Gültekin-Özgüven

Altın

et al. 2020

Heliyon

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This study offers a suitable and easy proliposome-liposome method that enhances the encapsulation ability of liposome structures on poor water-soluble extracts. Pollen phenolic extract (PPE) was studied to show applicability in the proposed method. The poor water-soluble PPE (0.2%, w/v) was encapsulated by liposomes generated from proliposomes (P-liposomes) that were prepared via high-pressure homogenization technique without using any organic solvents and high temperature. Only a few drops of ethanol were used to dissolve poor water-soluble compounds in PPE during the preparation of P-liposomes. The trace amount of ethanol maintained the improvement of PPE solubility in P-liposome dispersion, hence the in vitro bioaccessibility and bioactivity of PPE incorporated in P-liposomes increased. Thus, higher encapsulation efficiency was found in P-liposomes compared to conventional liposomes (C-liposomes) in which the EE was 75 and 73%, respectively. To increase the physical stability of liposome structures, the surface of both P-liposomes and C-liposomes was covered with chitosan. There were found small changes between P-liposomes and C-liposomes in terms of mean diameter size and zeta potential. On the other hand, the bioactivity of encapsulated PPE showed differences in P-liposomes and C-liposomes. The antioxidant capacity of PPE in P-liposomes enhanced approximately two times in CUPRAC and three times in DPPH assays. Also, in vitro bioaccessibility of PPE in P-liposomes increased approximately 4 and 2 folds, respectively, regarding total phenolics and flavonoids. To our knowledge, this is the first report about the increment of encapsulation behavior of liposome structures on low water-soluble extract within an aqueous media.

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Effect of temperature, pH, β- and HP-β-cds on the solubility and stability of flavanones: Naringenin and hesperetin

Cited by 32 publications

References 27 publications

Amorphous Inclusion Complexes: Molecular Interactions of Hesperidin and Hesperetin with HP-Β-CD and Their Biological Effects

Amorphous Inclusion Complexes: Molecular Interactions of Hesperidin and Hesperetin with HP-Β-CD and Their Biological Effects

Encapsulation of Hydrophobic and Low-Soluble Polyphenols into Nanoliposomes by pH-Driven Method: Naringenin and Naringin as Model Compounds

Liposomal nanodelivery systems generated from proliposomes for pollen extract with improved solubility and in vitro bioaccessibility

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