Enhancement of the water solubility and antioxidant capacities of mangiferin by transglucosylation using a cyclodextrin glycosyltransferase

Lee, Ji Yeon; Kim, Hayeong; Moon, Yedam; Kwak, So-Hyung; Kang, Choon Gil; Park, Chanho; Jo, JaeHyeok; Kim, Seung Wook; Pal, Kunal; Kang, Dong Hyun; Kim, Doman

doi:10.1016/j.enzmictec.2022.110065

Cited by 9 publications

(6 citation statements)

References 33 publications

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“…The water solubility of aglycones, such as flavonoid and phenolic compounds, depends on the types of linkages and sugar moieties . Generally, the more sugar moieties attached to flavonoids, the more water solubility is enhanced. , Interestingly, prunin with one glucoside showed 10 times higher solubility than naringin with disaccharides. This pattern was similar to previous studies showing that hesperetin 7-glucoside with a glucosyl moiety was more water soluble than hesperidin with a rhamnosyl glucosyl moiety. , Removing the glucosyl moiety from prunin decreased its water solubility.…”

Section: Resultsmentioning

confidence: 99%

“…15 The water solubility of aglycones, such as flavonoid and phenolic compounds, depends on the types of linkages and sugar moieties. 46 Generally, the more sugar moieties attached to flavonoids, the more water solubility is enhanced. 46,47 Interestingly, prunin with one glucoside showed 10 times higher solubility than naringin with disaccharides.…”

Section: Degree Of Freedommentioning

confidence: 99%

“…46 Generally, the more sugar moieties attached to flavonoids, the more water solubility is enhanced. 46,47 Interestingly, prunin with one glucoside showed 10 times higher solubility than naringin with disaccharides. This pattern was similar to previous studies showing that hesperetin 7glucoside with a glucosyl moiety was more water soluble than hesperidin with a rhamnosyl glucosyl moiety.…”

Section: Degree Of Freedommentioning

confidence: 99%

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Production of Prunin and Naringenin by Using Naringinase from Aspergillus oryzae NYO-2 and Their Neuroprotective Properties and Debitterization

Seong

Kim

et al. 2023

J. Agric. Food Chem.

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Naringin is a flavanone glycoside in citrus fruits that has various biological functions. However, its bitterness affects the quality, economic value, and consumer acceptability of citrus products. Deglycosylation of naringin using naringinase decreases its bitterness and enhances its functional properties. In this study, eight microbial strains with naringinase activity were isolated from 33 yuzu-based fermented foods. Among them, naringinase from Aspergillus oryzae NYO-2, having the highest activity, was used to produce prunin and naringenin. Under optimal conditions, 19 mM naringin was converted to 14.06 mM prunin and 1.97 mM naringenin. The bitterness of prunin and naringenin was significantly decreased compared to naringin using the human bitter taste receptor TAS2R39. The neuroprotective effects of prunin and naringenin on human neuroblastoma SH-SY5Y cells treated with scopolamine were greater than that of naringin. These findings can widen the potential applications of deglycosylation of naringin to improve sensory and functional properties.

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Section: Resultsmentioning

confidence: 99%

Section: Degree Of Freedommentioning

confidence: 99%

Section: Degree Of Freedommentioning

confidence: 99%

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Production of Prunin and Naringenin by Using Naringinase from Aspergillus oryzae NYO-2 and Their Neuroprotective Properties and Debitterization

Seong

Kim

et al. 2023

J. Agric. Food Chem.

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“…Because of this, many different strategies were proposed to address this limitation. This includes amorphization [ 28 , 29 ], formation of monocrystals [ 30 , 31 ], micronization [ 32 ] and solid dispersion formation [ 33 ], complexation with cyclodextrins [ 34 , 35 ], salts [ 36 , 37 ] and cocrystals [ 38 , 39 ] formation. Another way of improving solubility involves cosolvation techniques in which a particular amount of a solvent is added to the primary solvent [ 40 , 41 , 42 ] resulting in elevated solubility.…”

Section: Introductionmentioning

confidence: 99%

Quantification of Caffeine Interactions in Choline Chloride Natural Deep Eutectic Solvents: Solubility Measurements and COSMO-RS-DARE Interpretation

Jeliński¹,

Cysewski²

2022

IJMS

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Solubility of active pharmaceutical ingredients is an important aspect of drug processing and formulation. Although caffeine was a subject of many studies aiming to quantify saturated solutions, many applied solvents suffer from not being environmentally friendly. This work fills this gap by presenting the results of solubility measurements in choline chloride natural deep eutectic solvents, ccNADES, comprising one of seven of the following polyalcohols: glycerol, sorbitol, xylitol, glucose, sucrose, maltose and fructose. The ratio of ccNADES components was optimized for maximizing caffeine solubility at room temperature. Additionally, temperature dependent solubility was measured for the first four systems exhibiting the highest solubility potential, both in their neat forms and in mixtures with water. Results were used for intermolecular interactions assessments using the COSMO-RS-DARE approach, which led to a perfect match between experimental and computed solubility values. An important methodological discussion was provided for an appropriate definition of the systems. Surprising linear trends were observed between the values of fitting parameters and water-ccNADES composition. In addition, comments on selection of the values of the fusion thermodynamic parameters were provided, which led to the conclusion that COSMO-RS-DARE solubility computations can effectively compensate for the inaccuracies of these important physicochemical properties.

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“…The position of transglycosylation on an acceptor molecule depends on the specificity of the enzyme used and can lead to differently functionalized products [ 128 , 129 ]. Scientific studies showed that the attachment of sugar moiety can influence the biological activity of many synthetic and natural compounds [ 130 , 131 , 132 ].…”

Section: Biotechnological Modifications and Combination With Biotechn...mentioning

confidence: 99%

Fisetin—In Search of Better Bioavailability—From Macro to Nano Modifications: A Review

Szymczak,

Cielecka-Piontek

2023

IJMS

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As secondary plant metabolites, polyphenols are abundant in fruits and vegetables. They are in high demand because of their many health benefits. However, their low bioavailability makes them complex compounds to use for therapeutic purposes. Due to the limited solubility of phytocompounds, dietary supplements made from them may only be partially effective. Such molecules include fisetin, found in strawberries, and have shown great promise in treating Alzheimer’s disease and cancer. Unfortunately, because of their limited water solubility, low absorption, and poor bioavailability, the assistance of nanotechnology is required to allow them to fulfil their potential fully. Here, we provide evidence that nanodelivery methods and structure modifications can improve fisetin bioavailability, which is linked to improvements in therapeutic efficacy. An open question remains as to which nanocarrier should be chosen to meet the abovementioned requirements and be able to enhance fisetin’s therapeutic potential to treat a particular disease.

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Enhancement of the water solubility and antioxidant capacities of mangiferin by transglucosylation using a cyclodextrin glycosyltransferase

Cited by 9 publications

References 33 publications

Production of Prunin and Naringenin by Using Naringinase from Aspergillus oryzae NYO-2 and Their Neuroprotective Properties and Debitterization

Production of Prunin and Naringenin by Using Naringinase from Aspergillus oryzae NYO-2 and Their Neuroprotective Properties and Debitterization

Quantification of Caffeine Interactions in Choline Chloride Natural Deep Eutectic Solvents: Solubility Measurements and COSMO-RS-DARE Interpretation

Fisetin—In Search of Better Bioavailability—From Macro to Nano Modifications: A Review

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