Multiple complexation of cyclodextrin with soy isoflavones present in an enriched fraction

Yatsu, Francini K.J.; Koester, Letícia Scherer; Lula, Ivana S.; Passos, Joel J.; Sinisterra, Rubén D.; Bassani, Valquíria Linck

doi:10.1016/j.carbpol.2013.06.062

Cited by 34 publications

(15 citation statements)

References 25 publications

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“…In general, CD derivatives such as HPβCD were more efficient as complexation agents compared to parent βCD and, in many cases, an increased antioxidant capacity of CD encapsulated polyphenols was observed [16,17]. Taking all of this into account, it seems that the use of CD aqueous solutions as an extraction medium could be a valid approach to efficiently extract bioactive compounds from the plant material, especially taking into account the results of Yatsu et al [18], who demonstrated the possibility of the simultaneous complexation of daidzein, genistein, and glycitein from an enriched soy fraction with the HPβCD. An additional benefit of the CD-based extraction could be in their ability to chemically stabilize sensitive molecules by inclusion complex formation, considering that ultrasound may trigger or accelerate some chemical reaction in the sample, such as degradation of phenolic acids as well as degradation and oxidation of flavonoids [19].…”

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confidence: 89%

“…The dissolved molecules would be able to interact with HPβCD present in the extraction medium according to their corresponding affinity. The simultaneous CD complexation of several different molecules was already demonstrated for isoflavones present in an enriched soy fraction [18] as well as in the case of ferulic and galic acid coencapsulation in HPβCD [30]. After equilibration of the system, the components that form the most stabile complexes with HPβCD would remain in the solution, thus being more efficiently extracted.…”

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confidence: 95%

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Therapeutic Potential of Hydroxypropyl-β-Cyclodextrin-Based Extract of Medicago sativa in the Treatment of Mucopolysaccharidoses

2016

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Mucopolysaccharidoses are inherited metabolic disorders resulting in the dysfunction of enzymes involved in the degradation of glycosaminoglycans, leading to severe clinical symptoms and a significantly shortened life span of patients. Flavonoids are recognized as glycosaminoglycan metabolism modulators, able to correct glycosaminoglycan cell storage. Therefore, the aim of this work was the development of an efficient and eco-friendly extraction process of phytochemicals from by simultaneous use of ultrasound extraction and hydroxypropyl--cyclodextrin complexation, and investigation of the potential of such an extract as a glycosaminoglycan metabolism modulator. The Box-Behnken design and response surface methodology were used in order to optimize the extraction process, considering hydroxypropyl--cyclodextrin concentration, ultrasonic power, and extraction time as the key parameters. The dependent variables included total phenolicand total flavonoid content, DPPH radical scavenging activity, and Fe chelating activity, due to the importance of oxidative stress in the pathology of mucopolysaccharidoses. The developed technology using hydroxypropyl--cyclodextrin led to more selective flavonoid extraction from than obtained either by the use of water or ethanol. The lyophilization of extracts resulted in products with high radical scavenging activity, suitable for further use. The application of 20 mM hydroxypropyl--cyclodextrin solution, 432 W ultrasonic power, and an extraction time of 45 min resulted in an extract with both the highest total flavonoid content and the lowest radical scavenging activity IC. This extract reduced the levels of glycosaminoglycans in skin fibroblasts of mucopolysaccharidose III patient in a dose-dependent manner. At concentrations of 3 and 6 µg/mL, the observed levels of glycosaminoglycans were reduced by 41.2 and 51.1 %, respectively, clearly demonstrating the validity of the selected approach.

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confidence: 89%

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confidence: 95%

Therapeutic Potential of Hydroxypropyl-β-Cyclodextrin-Based Extract of Medicago sativa in the Treatment of Mucopolysaccharidoses

2016

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“…Genistein ability to cross biological membranes was also improved by the encapsulation with the CDs [59]. β-CD and HP-β-CD IC formation was investigated with a mixture of daidzein, genistein and glycitein [60]. All the isoflavones showed the highest affinity with HP-β-CD and the interaction between the CD and the bioactive molecules occur by insertion of the B-ring into the CD cavity [60].…”

Section: Cyclodextrins Inclusion Complexesmentioning

confidence: 99%

Flavonoids Loaded in Nanocarriers: An Opportunity to Increase Oral Bioavailability and Bioefficacy

Bilia¹,

Isacchi²,

Righeschi³

et al. 2014

FNS

100

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Flavonoids are among the biggest group of polyphenols, widely distributed in plant-based foods. A plethora of evidence supports the health benefits and value of flavonoids can play in the physiological function treatment and in the prevention of disease particularly in the prevention of degenerative conditions including cancers, cardiovascular and neurodegenerative diseases. Hence, flavonoids represent the active constituents of many dietary supplements and herbal remedies, as well as there is an increasing interest in this class of polyphenols as functional ingredients of beverages, food grains and dairy products. Conversely, various studies have also shown that flavonoids have some drawbacks after oral administration such as stability, bioavailability and bioefficacy. This article reviews the current status of novel nanodelivery systems including nanospheres, nanocaspsules, micro-and nanoemulsions, micelles, solid lipid nanoparticles and nanostructured lipid capsules, successfully developed for overcoming the delivery challenges of flavonoids.

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“…One of the major limitations of using natural products is a reduced water solubility and bioavailability of the molecules of interest. An innovative strategy to overcome such challenges is their complexation with cyclodextrins; in other words, the formation of inclusion complexes to increase the water solubility of the plant compound [23]. This molecular property has enabled the use of cyclodextrins in different applications in science and technology, mainly in the pharmaceutical industry, by virtue of obtaining new drugs with different physical and chemical properties with the same active compounds [24].…”

Section: Introductionmentioning

confidence: 99%

Effect of α-Bisabolol and Its β-Cyclodextrin Complex as TetK and NorA Efflux Pump Inhibitors in Staphylococcus aureus Strains

et al. 2020

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Efflux pumps are proteins present in the plasma membrane of bacteria, which transport antibiotics and other compounds into the extracellular medium, conferring resistance. The discovery of natural efflux pump inhibitors is a promising alternative. α-Bisabolol is a sesquiterpene isolated from several plants such as Matricaria chamomilla L. and has important properties such as antibacterial and anti-inflammatory activity. Currently, the formation of inclusion complexes with β-Cyclodextrin has been used for improving the physicochemical characteristics of the host molecule. This study evaluated the effect of α-Bisabolol, in isolation and in complexation with β-Cyclodextrin, as TetK and NorA efflux pump inhibitors in Staphylococcus aureus strains. The minimum inhibitory concentration (MIC) was determined. Subsequently, inhibitory activity over the pumps was observed by an MIC reduction for the antibiotics, by using subinhibitory concentrations (MIC/8) in combination with tetracycline and norfloxacin. The MIC of the compounds was ≥1024 μg/mL. α-Bisabolol potentiated the action of tetracycline and reduced the MIC of norfloxacin to a clinically relevant concentration. The complexed substance showed synergism however, the effect of the isolated α-Bisabolol was superior to the complex. These results indicate α-Bisabolol is a potential substance to be used as an efflux pump inhibitor.

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Multiple complexation of cyclodextrin with soy isoflavones present in an enriched fraction

Cited by 34 publications

References 25 publications

Therapeutic Potential of Hydroxypropyl-β-Cyclodextrin-Based Extract of Medicago sativa in the Treatment of Mucopolysaccharidoses

Therapeutic Potential of Hydroxypropyl-β-Cyclodextrin-Based Extract of Medicago sativa in the Treatment of Mucopolysaccharidoses

Flavonoids Loaded in Nanocarriers: An Opportunity to Increase Oral Bioavailability and Bioefficacy

Effect of α-Bisabolol and Its β-Cyclodextrin Complex as TetK and NorA Efflux Pump Inhibitors in Staphylococcus aureus Strains

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