Degradation kinetics of fisetin and quercetin in solutions affected by medium pH, temperature and co-existed proteins

Wang, Jing; Zhao, Xin‐Huai

doi:10.2298/jsc150706092w

Cited by 64 publications

(56 citation statements)

References 25 publications

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“…On the other hand, quercetin showed a lower analytical response at pH 7.4, despite the acidification carried out during sample preparation; thus, it was necessary to define an independent regression model for this compound in each pH condition. The lower response of quercetin at alkaline pH could be a consequence of the poor stability of the compound as was confirmed experimentally (Figure , Table ) and supported by other authors …”

Section: Discussionsupporting

confidence: 77%

Matrix effects of the hydroethanolic extract and the butanol fraction of calyces from Physalis peruviana L. on the biopharmaceutics classification of rutin

Moré

Feltrin

Brambila

et al. 2020

Journal of Pharmacy and Pharmacology

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Objectives The Biopharmaceutics Classification System (BCS) categorizes active pharmaceutical ingredients according to their solubility and permeability properties, which are susceptible to matrix or formulation effects. The aim of this research was to evaluate the matrix effects of a hydroethanolic extract of calyces from Physalis peruviana L. (HEE) and its butanol fraction (BF), on the biopharmaceutics classification of their major compound, quercetin‐3‐O‐rutinoside (rutin, RU). Methods Rutin was quantified by HPLC‐UV, and Caco‐2 cell monolayer transport studies were performed to obtain the apparent permeability values (Papp). Aqueous solubility was determined at pH 6.8 and 7.4. Key findings The Papp values followed this order: BF > HEE > RU (1.77 ± 0.02 > 1.53 ± 0.07 > 0.90 ± 0.03 × 10−5 cm/s). The lowest solubility values followed this order: HEE > RU > BF (2.988 ± 0.07 > 0.205 ± 0.002 > 0.189 ± 0.005 mg/ml). Conclusions According to these results, rutin could be classified as BCS classes III (high solubility/low permeability) and IV (low solubility/low permeability), depending on the plant matrix. Further work needs to be done in order to establish how apply the BCS for research and development of new botanical drugs or for bioequivalence purposes.

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Section: Discussionsupporting

confidence: 77%

Matrix effects of the hydroethanolic extract and the butanol fraction of calyces from Physalis peruviana L. on the biopharmaceutics classification of rutin

Moré

Feltrin

Brambila

et al. 2020

Journal of Pharmacy and Pharmacology

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“…The reaction was shown to be pH-depended within a pH range from 4.1 to 7, exhibiting a linear correlation between k and pH. Such a phenomenon was further confirmed by more recent examinations, which showed a pH-depended degradation of quercetin within a narrower pH region of 6 to 7.5, at 37 • C, but also a temperature-dependent increase in k, within a range of 37 to 65 • C [20]. In the same line, latter investigations showed that Cu 2+ -induced quercetin oxidation at pH 8 and 97 • C also displayed first-order kinetics, with k being linearly correlated [14].…”

Section: Preliminary Oxidation Kinetics and Temperature Effectssupporting

confidence: 67%

Empirical Kinetic Modelling of the Effect of l-Ascorbic Acid on the Cu(II)-Induced Oxidation of Quercetin

et al. 2018

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This study aimed at investigating the effect of L-ascorbic acid on the Cu 2+ -induced oxidation of quercetin, within a pH range from 6.7 to 8.3 and temperatures varying from 53 to 87 • C. Initial examinations showed that quercetin degradation obeyed apparent first-order kinetics and it was significantly affected by temperature. Modelling of the effect of L-ascorbic acid by implementing response surface methodology suggested that L-ascorbic acid did not impact quercetin oxidation significantly (p < 0.05) and led to an empirical kinetic model based on temperature (T) and pH. Liquid chromatography-diode array-mass spectrometry analyses revealed the presence of typical quercetin degradation and oxidation products, including protocatechuic acid and 2-(hydroxybenzoyl)-2-hydroxybenzofuran-3(2H)-one. It was concluded that the formation of L-ascorbyl or other radicals (superoxide anion) may be involved in quercetin oxidation and this fact merits further attention to illuminate the possible beneficial or adverse nutritional consequences of such reactions in foods.ChemEngineering 2018, 2, 46 2 of 14 was shown to exhibit improved antioxidant characteristics [7]. More recent data on this particular product were in the same line, revealing a 200-fold higher cytoprotective potency [8].L-Ascorbic acid (vitamin C) is a well-known food antioxidant that may eliminate a spectrum of oxidising species, such as superoxide anion radical (O 2 •− ), hydroxyl radical (OH • ) and singlet oxygen, due to its ease of oxidation by either a one-or two-electron transfer [9,10]. Ascorbic acid may also lower the oxidation state of metals, such as iron and copper, and their valence, thus affecting oxidation catalysis. These unique features make L-ascorbic acid a powerful antioxidant, capable to protect a variety of substrates from oxidation. L-Ascorbic acid may be rapidly oxidised in the presence of bivalent copper (Cu 2+ ), but the extent of oxidation may be limited in the presence of metal-chelating flavonoids, such as quercetin [11,12]. However, L-ascorbic acid may also act as an antioxidant in such a system, protecting quercetin from Cu 2+ -induced oxidative degradation [5]. Therefore, depending on the conditions (pH, temperature, the presence of other redox species, relevant amounts of redox species implicated), in a system containing L-ascorbic acid, quercetin and Cu 2+ , one antioxidant may be sacrificed at the expense of the other, yet a prediction regarding the eventual shift of such a cascade of reactions would be rather difficult, due to the high complexity. This being the case, this study aimed at modelling the effect of L-ascorbic acid on quercetin stability in the presence of Cu 2+ , considering the kinetic behaviour of quercetin degradation as a function of pH and temperature. Following a preliminary investigation, the interactions between L-ascorbic acid and quercetin were modelled by deploying response surface methodology. Tentative characterisation of major quercetin oxidation products using liquid chromatography-mass spectrometry ...

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“…An example is the biochemical transformation of flavylium cation of anthocyanidin to less stable chalcone and carbinol pseudobase forms even at near-neutral pH 45 , which eventually leads to degradation of anthocyanin 42,46 . Similarly, flavonols, such as quercetin, have been reported to undergo oxidation, hydroxylation, and ring cleavage at medium pH values in a time-dependent manner resulting to the formation of complex product profiles 47 . The low chemical stability of these compounds, as a function of their chemical structure, in the mild alkaline pH condition of the small intestine could cause their degradation and inactivity 46 .…”

Section: Discussionmentioning

confidence: 99%

Bio-properties of Saba banana (Musa ‘saba’, ABB Group): Influence of maturity and changes during simulated in vitro gastrointestinal digestion

Reginio

Qin

Ketnawa

et al. 2020

Sci Rep

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Saba banana, a popular fruit crop grown in Southeast Asia, is an economical source of a variety of beneficial agents. This study examined the variations in total phenolic, flavonoid, and antioxidant activities of five maturity stages of Saba banana, and their changes during simulated in vitro gastrointestinal digestion as affected by varying structural compositions. Antioxidant activities were evaluated using ferric reducing antioxidant power (FRAP), metal ion chelating (MIC) activity, and 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays. Results of DPPH and ABTS were compared in terms of TEAC (Trolox Equivalent Antioxidant Capacity) and VCEAC (Vitamin C Equivalent Antioxidant Capacity) values. Bio-properties were found to be highest in mature green stage with values slightly decreased as ripening proceeded. Simulated digestion showed a continuous increase in total phenolic with comparatively faster release in structure-less state (slurry) than samples with intact structure (cut). The trend of antioxidant activities was increased in the gastric phase and then decreased at the onset of intestinal phase, except for MIC which showed a reverse effect. Our study indicated that the bio-properties of Saba banana were affected by maturity and modifications in its physical structure and composition could influence the release behaviors of food components during simulated digestion. Owing to its increasing demand and whole-year availability, banana is considered as one of the world's most important fruit crops in terms of commercial production and one of the most consumed staple food commodities after major cereals 1,2. An estimated of 19.2 million tons of banana had been exported globally in 2018 which accounted to the strong supply growth from the two leading exporters, Ecuador and the Philippines 3. Among the economically important banana cultivars in the Philippines, foremost of which is Saba (Musa 'saba'[Musa acuminata × Musa balbisiana]), an ABB genome group, which accounts to more than 25% of the country's banana production. This banana variety can be utilized at all stages of maturity either raw or cooked and is used primarily for manufacturing various food products such as condiments (banana ketchup), snacks (banana chips), viands, and desserts 4. Saba banana is also relished in other Southeast Asian countries 5 but is gaining popularity in Latin America 2 and Southern Nigeria 6. Banana is not only an important source of starchy staple food but could also exert a beneficial effect on human health. It contains phytonutrients, including vitamins and different classes of phenolic compounds 2,7. In plants, phenolic compounds may exist in free, soluble conjugated (esterified), and insoluble-bound forms 8,9. Research studies have shown that bound phenolics have demonstrated a significantly higher antioxidant capacity compared to free phenolics in numerous in vitro antioxidant assays carried out 10. Insoluble bound phenolics are localized in the cell wall matri...

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Degradation kinetics of fisetin and quercetin in solutions affected by medium pH, temperature and co-existed proteins

Cited by 64 publications

References 25 publications

Matrix effects of the hydroethanolic extract and the butanol fraction of calyces from Physalis peruviana L. on the biopharmaceutics classification of rutin

Matrix effects of the hydroethanolic extract and the butanol fraction of calyces from Physalis peruviana L. on the biopharmaceutics classification of rutin

Empirical Kinetic Modelling of the Effect of l-Ascorbic Acid on the Cu(II)-Induced Oxidation of Quercetin

Bio-properties of Saba banana (Musa ‘saba’, ABB Group): Influence of maturity and changes during simulated in vitro gastrointestinal digestion

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