Modeling the Solubility of Phenolic Acids in Aqueous Media at 37 °C

Furia, Emilia; Beneduci, Amerigo; Malacaria, Luana; Fazio, Alessia; Torre, Chiara La; Plastina, Pierluigi

doi:10.3390/molecules26216500

Cited by 22 publications

(20 citation statements)

References 63 publications

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“…The extraction of phenolic compounds is related to their solubility degree and chemical structure [ 29 ]. Hydroxybenzoic acid derivatives exhibit high solubility due to the presence of hydroxyl groups in their structure, facilitating water interactions and enhancing extraction yields [ 30 ]. The differences in the phenolic profile of the CPF and the CPE were mainly due to the matrix type.…”

Section: Discussionmentioning

confidence: 99%

Understanding the Gastrointestinal Behavior of the Coffee Pulp Phenolic Compounds under Simulated Conditions

et al. 2022

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Numerous residues, such as the coffee pulp, are generated throughout coffee processing. This by-product is a source of antioxidant phytochemicals, including phenolic compounds and caffeine. However, the antioxidant properties of the phenolic compounds from the coffee pulp are physiologically limited to their bioaccessibility, bioavailability, and biotransformation occurring during gastrointestinal digestion. Hence, this study explored the phenolic and caffeine profile in the coffee pulp flour (CPF) and extract (CPE), their intestinal bioaccessibility through in vitro digestion, and their potential bioavailability and colonic metabolism using in silico models. The CPE exhibited a higher concentration of phenolic compounds than the CPF, mainly phenolic acids (protocatechuic, chlorogenic, and gallic acids), followed by flavonoids, particularly quercetin derivatives. Caffeine was found in higher concentrations than phenolic compounds. The antioxidant capacity was increased throughout the digestive process. The coffee pulp matrix influenced phytochemicals’ behavior during gastrointestinal digestion. Whereas individual phenolic compounds generally decreased during digestion, caffeine remained stable. Then, phenolic acids and caffeine were highly bioaccessible, while flavonoids were mainly degraded. As a result, caffeine and protocatechuic acid were the main compounds absorbed in the intestine after digestion. Non-absorbed phenolic compounds might undergo colonic biotransformation yielding small and potentially more adsorbable phenolic metabolites. These results contribute to establishing the coffee pulp as an antioxidant food ingredient since it contains bioaccessible and potentially bioavailable phytochemicals with potential health-promoting properties.

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Section: Discussionmentioning

confidence: 99%

Understanding the Gastrointestinal Behavior of the Coffee Pulp Phenolic Compounds under Simulated Conditions

et al. 2022

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“…24,28 Moreover, commercial AEMs are prone to organic fouling with phenolic acids which reduces separation productivity and increases the capital costs of the EDI system due to requiring a larger number of cells to make up for the fouled cells. The generally low solubility limits for phenolic acids (such as ∼1 g kg −1 in water for p-coumaric, ferulic, or caffeic acid 31,32 ) further make separating these molecules challenging. There is a need for alternative ion-exchange materials that reduce ion transport resistances and mitigate fouling with phenolic acids.…”

Section: ■ Introductionmentioning

confidence: 99%

Integrated Ion-Exchange Membrane Resin Wafer Assemblies for Aromatic Organic Acid Separations Using Electrodeionization

Jordan

Kokoszka

Dona

et al. 2023

ACS Sustainable Chem. Eng.

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Aromatic acids, such as p-coumaric acid, are valuable chemical intermediates that are used in the specialty chemical industries because they are precursors to phenylpropanoid compounds. The separation of p-coumaric acid from fermentation broths is a critical step in the biochemical production process and more broadly the circular carbon economy. Electrodeionization (EDI) has been applied toward separations of low-carbon chain acids, but purifying p-coumaric acid has been challenging due to fouling and irreversible binding with ion-exchange membranes and resins. Here, we report a new membrane wafer assembly (MWA) consisting of laminated ion exchange membranes to porous ionomer-binder resin wafers for EDI. The MWAs in an EDI stack showed a 7-fold increase in p-coumaric acid capture while also using 70% less specific energy consumption when benchmarked against state-of-the-art resin wafer EDI modules. The more efficient p-coumaric acid recovery was ascribed to (i) the 38% reduction in interfacial transport resistance between the membrane and resin wafer and (ii) using imidazolium anion exchange membranes and ionomer binders in the MWA. MD simulations revealed enhanced transport rates for p-coumarate in imidazolium ionomers through π–π interactions. Adopting the new MWA significantly reduced the amount of ion-exchange membranes in EDI and may lead to drastic capital cost savings.

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“…6−8 However, the poor water solubility of phenolic acids has significantly hindered their practical use. 9,10 Although this problem can be resolved through formulation design, such as encapsulation and cosolvents, the process is generally complicated or with limited application scenarios. 11,12 Salt formation is a simple and cost-effective method for solubilizing poorly soluble drugs and does not require molecular modifications or complex formulations; thus, this method has been widely used in oral, transdermal, and parenteral drug delivery.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, phenolic acids have received considerable attention due to their wide range of bioactive and pharmaceutical efficacies. In addition to their well-known antioxidant and anti-inflammatory effects, phenolic acids can also exhibit antibacterial, antiviral, and anticancer properties and are also useful in preventive and adjuvant therapies for various cardiovascular diseases. − Furthermore, when phenolic acids are combined with other specific substances, a synergistic effect with enhanced efficacy is obtained, resulting in many potential applications in the food, medical, and cosmetic industries. − However, the poor water solubility of phenolic acids has significantly hindered their practical use. , Although this problem can be resolved through formulation design, such as encapsulation and cosolvents, the process is generally complicated or with limited application scenarios. , …”

Section: Introductionmentioning

confidence: 99%

Sustainable Bioactive Salts Fully Composed of Natural Products for Enhanced Pharmaceutical Applicability

Wang

Wang²,

Zhan³

et al. 2022

ACS Sustainable Chem. Eng.

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Phenolic acids are attractive plant-derived bioactive substances owing to their wide range of pharmaceutical properties for the prevention of various human diseases as well as their applications in adjuvant therapy. However, phenolic acids exhibit poor water solubility, which limits their bioavailability and applications. In this study, phenolic acids were combined with matrine to form salts. Matrine is an alkaloid from a traditional Chinese herb that also has abundant pharmaceutical features and was employed to enhance the water solubility and pharmaceutical applicability of phenolic acids. Five bioactive salts, i.e., matrinium syringate, matrinium vanillate, matrinium protocatechuate, matrinium caffeinate, and matrinium gallate, were synthesized and characterized. The results show that all the salts have a hydrogenbonding-stabilized orthorhombic crystal structure and exhibit a synergistic effect between the anions and cations. Compared with their raw materials, the salts display reduced melting points, higher water solubility (several to hundreds of times greater), lower cytotoxicity for normal human cells, as well as better anticancer, antibacterial, antioxidant, and anti-inflammatory capabilities, accompanied by relatively high thermal stability (>140 °C). This indicates that formation of salts by combining phenolic acids and matrine is an effective method for enhancing pharmaceutical applicability, which may be further used to develop new nutrients or drugs.

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Modeling the Solubility of Phenolic Acids in Aqueous Media at 37 °C

Cited by 22 publications

References 63 publications

Understanding the Gastrointestinal Behavior of the Coffee Pulp Phenolic Compounds under Simulated Conditions

Understanding the Gastrointestinal Behavior of the Coffee Pulp Phenolic Compounds under Simulated Conditions

Integrated Ion-Exchange Membrane Resin Wafer Assemblies for Aromatic Organic Acid Separations Using Electrodeionization

Sustainable Bioactive Salts Fully Composed of Natural Products for Enhanced Pharmaceutical Applicability

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