Hydroxycinnamic Acids

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Carolyn J Buttswilmsmeyer - One of the best experts on this subject based on the ideXlab platform.

V E Petrenko - One of the best experts on this subject based on the ideXlab platform.

  • Hydroxycinnamic Acids in supercritical carbon dioxide the dependence of cosolvent induced solubility enhancement on the selective solvation
    Journal of Supercritical Fluids, 2019
    Co-Authors: D L Gurina, M L Antipova, V E Petrenko
    Abstract:

    Abstract Simulation of Hydroxycinnamic Acids (caffeic, p-coumaric, ferulic, synapic) in pure and modified by polar cosolvents (methanol, acetone) supercritical carbon dioxide has been carried out using classical molecular dynamics. Dependences of solvation free energies of the Acids on the pressure and cosolvent mole fraction have been calculated using Bennett’s acceptance ratio method. When a polar cosolvent is added, the solvation free energy decreases sharply, and with a subsequent increase in its concentration, it changes slightly. The cosolvent-induced effect decreases with increasing pressure. The structural parameters characterizing the selective solvation of the Acids have been calculated. A correlation between the cosolvent-induced solubility enhancement and the average number of solute – cosolvent hydrogen bonds has been found.

  • Selective solvation in cosolvent-modified supercritical carbon dioxide on the example of Hydroxycinnamic Acids. The role of cosolvent self-association
    The Journal of Supercritical Fluids, 2018
    Co-Authors: D L Gurina, M L Antipova, Ekaterina G. Odintsova, V E Petrenko
    Abstract:

    Abstract The study of the selective solvation of Hydroxycinnamic Acids (para-coumaric, caffeic) by a polar cosolvent (acetone, methanol) in supercritical carbon dioxide at T = 328 K, ρ = 0.772 g/cm3 has been carried out using the molecular dynamics and quantum-chemical calculations. It has been shown that the selective solvation of the solute occurs by the formation of hydrogen-bonded complexes with a cosolvent. The formation of hydrogen-bonded complexes with two or more cosolvent molecules is most likely in methanol-modified supercritical carbon dioxide even at a low concentration of the methanol, whereas the formation of a complex with one cosolvent molecule is preferred in the acetone-modified fluid. If the cosolvent is capable of self-association in supercritical carbon dioxide (methanol), then hydrogen-bonded cosolvent clusters are grouped around the solvate complexes even at low concentration of it. The number of molecules in such clusters can reach 10, although methanol associates consist of no more than three molecules in the fluid bulk.

Gary Williamson - One of the best experts on this subject based on the ideXlab platform.

  • Interaction of Hydroxycinnamic Acids and their conjugates with organic anion transporters and ATP-binding cassette transporters
    Molecular nutrition & food research, 2011
    Co-Authors: Chi C. Wong, Denis Barron, Gary Williamson, Caroline Orfila, Fabiola Dionisi, Peter Krajcsi
    Abstract:

    Scope: Hydroxycinnamic Acids are abundant antioxidants in our diet. In humans, Hydroxycinnamic Acids are metabolized to form sulfates and glucuronides, with the majority recovered in urine. Methods and results: We assessed the potential roles of organic anion transporters (OATs) and ATP-binding cassette (ABC) transporters in the renal uptake and efflux of Hydroxycinnamic acid conjugates. Uptake studies using OAT1 (SLC22A6)-, OAT2 (SLC22A7)-, and OAT3 (SLC22A8)-expressing 293H embryonic kidney cells showed that OAT1 and OAT3, but not OAT2, accepted Hydroxycinnamic acid conjugates as substrates. OAT1 and OAT3 mediated the basolateral uptake of Hydroxycinnamic acid sulfates and glucuronide conjugates, respectively. Hydroxycinnamic acid sulfates are substrates of OAT4 and were capable of trans-stimulating 5-carboxyfluorescein uptake mediated by OAT4. On the other hand, Hydroxycinnamic acid conjugates are not substrates for the ABC transporters, multidrug resistance protein 2 (MRP2/ABCC2) or breast cancer resistance protein (BCRP/ABCG2), demonstrated by the inability to alter ATPase activity. Cis-inhibition studies with OATs and MRPs revealed that Hydroxycinnamic acid conjugates have limited impact on the transport of model substrates significantly at physiological concentrations. Conclusion: Concerted action of OAT1, OAT3, and OAT4 is involved in the elimination of Hydroxycinnamic acid conjugates into urine, whereas MRP2 and breast cancer resistance protein are not involved in the disposition of these conjugates.

  • in vitro and in vivo conjugation of dietary Hydroxycinnamic Acids by udp glucuronosyltransferases and sulfotransferases in humans
    Journal of Nutritional Biochemistry, 2010
    Co-Authors: Chi Chun Wong, Angelique Stalmach, Walter Meinl, Hans Rudolf Prof Glatt, Denis Barron, Heike Steiling, Alan Crozier, Gary Williamson
    Abstract:

    Hydroxycinnamic Acids are a class of phenolic antioxidants found widely in dietary plants. Their biotransformation in the human organism primarily involves Phase II conjugation reactions. In this study, activities of UDP-glucuronosyltransferases (UGTs) and sulfotransferases (SULTs) towards major dietary Hydroxycinnamic Acids (caffeic, dihydrocaffeic, dihydroferulic, ferulic and isoferulic Acids) were investigated. Conjugate formation was evaluated using human liver and intestinal S9 homogenates, and in vitro characterization was carried out using recombinant human UGTs and SULTs. Analysis of the kinetics of Hydroxycinnamic acid conjugation in human S9 homogenates revealed that intrinsic clearance (Vmax/Km) is much greater for sulfation than for glucuronidation. Assessment of activity using a panel of recombinant human SULTs showed that SULT1A1 is most active in the sulfation of caffeic, dihydrocaffeic and isoferulic Acids, while SULT1E1 is most active in the sulfation of ferulic and dihydroferulic Acids. Only isoferulic acid was significantly glucuronidated by human liver S9 homogenates, explained by the high activity of liver-specific UGT1A9. Studies on the kinetics of active SULTs and UGTs demonstrated a markedly lower Km for SULTs. To further corroborate our findings, we carried out an intervention study in healthy humans to determine the Hydroxycinnamic acid conjugates in urine after consumption of hydroxycinnamate-rich coffee (200 ml). Analysis showed that sulfates are the main conjugates in urine, with the exception of isoferulic acid, which is mainly glucuronidated. These data suggest that sulfates are the predominant Hydroxycinnamic acid conjugates in humans, and that SULT mediated sulfation is a major factor determining the bioavailability of Hydroxycinnamic Acids in vivo.

Martin O Bohn - One of the best experts on this subject based on the ideXlab platform.

D L Gurina - One of the best experts on this subject based on the ideXlab platform.

  • Hydroxycinnamic Acids in supercritical carbon dioxide the dependence of cosolvent induced solubility enhancement on the selective solvation
    Journal of Supercritical Fluids, 2019
    Co-Authors: D L Gurina, M L Antipova, V E Petrenko
    Abstract:

    Abstract Simulation of Hydroxycinnamic Acids (caffeic, p-coumaric, ferulic, synapic) in pure and modified by polar cosolvents (methanol, acetone) supercritical carbon dioxide has been carried out using classical molecular dynamics. Dependences of solvation free energies of the Acids on the pressure and cosolvent mole fraction have been calculated using Bennett’s acceptance ratio method. When a polar cosolvent is added, the solvation free energy decreases sharply, and with a subsequent increase in its concentration, it changes slightly. The cosolvent-induced effect decreases with increasing pressure. The structural parameters characterizing the selective solvation of the Acids have been calculated. A correlation between the cosolvent-induced solubility enhancement and the average number of solute – cosolvent hydrogen bonds has been found.

  • Selective solvation in cosolvent-modified supercritical carbon dioxide on the example of Hydroxycinnamic Acids. The role of cosolvent self-association
    The Journal of Supercritical Fluids, 2018
    Co-Authors: D L Gurina, M L Antipova, Ekaterina G. Odintsova, V E Petrenko
    Abstract:

    Abstract The study of the selective solvation of Hydroxycinnamic Acids (para-coumaric, caffeic) by a polar cosolvent (acetone, methanol) in supercritical carbon dioxide at T = 328 K, ρ = 0.772 g/cm3 has been carried out using the molecular dynamics and quantum-chemical calculations. It has been shown that the selective solvation of the solute occurs by the formation of hydrogen-bonded complexes with a cosolvent. The formation of hydrogen-bonded complexes with two or more cosolvent molecules is most likely in methanol-modified supercritical carbon dioxide even at a low concentration of the methanol, whereas the formation of a complex with one cosolvent molecule is preferred in the acetone-modified fluid. If the cosolvent is capable of self-association in supercritical carbon dioxide (methanol), then hydrogen-bonded cosolvent clusters are grouped around the solvate complexes even at low concentration of it. The number of molecules in such clusters can reach 10, although methanol associates consist of no more than three molecules in the fluid bulk.