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Research Articles

Charting the structural and thermodynamic determinants in phenolic acid natural product – cyclodextrin encapsulations

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Pages 2642-2658 | Received 28 Feb 2020, Accepted 30 Mar 2020, Published online: 16 Apr 2020

References

  • Abedini, A., Roumy, V., Mahieux, S., Biabiany, M., Standaert-Vitse, A., Rivière, C., Sahpaz, S., Bailleul, F., Neut, C., & Hennebelle, T. (2013). Rosmarinic acid and its methyl ester as antimicrobial components of the hydromethanolic extract of Hyptis atrorubens Poit. (Lamiaceae). Evidence-Based Complementary and Alternative Medicine, 2013, 1–11. 10.1155/2013/604536
  • Aksamija, A., Polidori, A., Plasson, R., Dangles, O., & Tomao, V. (2016). The inclusion complex of rosmarinic acid into beta-cyclodextrin: A thermodynamic and structural analysis by NMR and capillary electrophoresis. Food Chemistry, 208, 258–263. 10.1016/j.foodchem.2016.04.008
  • Astray, G., Gonzalez-Barreiro, C., Mejuto, J. C., Rial-Otero, R., & Simal-Gándara, J. (2009). A review on the use of cyclodextrins in foods. Food Hydrocolloids, 23(7), 1631–1640. 10.1016/j.foodhyd.2009.01.001
  • Berhow, M. A., Affum, A. O., & Gyan, B. A. (2012). Rosmarinic acid content in antidiabetic aqueous extract of Ocimum canum sims grown in Ghana. Journal of Medicinal Food, 15(7), 611–620. 10.1089/jmf.2011.0278
  • Case, D., Darden, T. A., Cheatham, T. E., Simmerling, C., Wang, J., Duke, R., Luo, R., Walker, R. C., Zhang, W., Merz, K. M., Roberts, B., & Kollman, P. A. (2012). AMBER 12. University of California.
  • Celik, S. E., Ozyurek, M., Tufan, A. N., Guclu, K., & Apak, R. (2011). Spectroscopic study and antioxidant properties of the inclusion complexes of rosmarinic acid with natural and derivative cyclodextrins. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 78(5), 1615–1624. 10.1016/j.saa.2011.02.017
  • Chao, C. Y., Mong, M. C., Chan, K. C., & Yin, M. C. (2010). Anti-glycative and anti-inflammatory effects of caffeic acid and ellagic acid in kidney of diabetic mice. Molecular Nutrition & Food Research, 54(3), 388–395. 10.1002/mnfr.200900087
  • Chattah, A. K., Mroue, K. H., Pfund, L. Y., Ramamoorthy, A., Longhi, M. R., & Garnero, C. (2013). Insights into novel supramolecular complexes of two solid forms of norfloxacin and β-cyclodextrin. Journal of Pharmaceutical Sciences, 102(10), 3717–3724. 10.1002/jps.23683
  • Chen, J. H., & Ho, C.-T. (1997). Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds. Journal of Agricultural and Food Chemistry, 45(7), 2374–2378. 10.1021/jf970055t
  • Christodoulou, E., Kechagia, I.-A., Tzimas, S., Balafas, E., Kostomitsopoulos, N., Archontaki, H., Dokoumetzidis, A., & Valsami, G. (2015). Serum and tissue pharmacokinetics of silibinin after per os and i.v. administration to mice as a HP-beta-CD lyophilized product. International Journal of Pharmaceutics, 493(1–2), 366–373. 10.1016/j.ijpharm.2015.07.060
  • Cockerill, F., & Clinical and Laboratory Standards Institute. (2018). Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically: Approved Standard. Clinical and Laboratory Standards Institute.
  • Cravotto, G., Binello, A., Baranelli, E., Carraro, P., & Trotta, F. (2006). Cyclodextrins as food additives and in food processing. Current Nutrition & Food Science, 2(4), 343–350. 10.2174/157340106778699485
  • Ekambaram, S. P., Perumal, S. S., Balakrishnan, A., Marappan, N., Gajendran, S. S., & Viswanathan, V. (2016). Antibacterial synergy between rosmarinic acid and antibiotics against methicillin-resistant Staphylococcus aureus. Journal of Intercultural Ethnopharmacology, 5(4), 358–363. 10.5455/jice.20160906035020
  • Ekor, M. (2014). The growing use of herbal medicines: Issues relating to adverse reactions and challenges in monitoring safety. Frontiers in Pharmacology, 4, 177. 10.3389/fphar.2013.00177
  • Exarchou, V., Troganis, A., Gerothanassis, I. P., Tsimidou, M., & Boskou, D. (2001). Identification and quantification of caffeic and rosmarinic acid in complex plant extracts by the use of variable-temperature two-dimensional nuclear magnetic resonance spectroscopy. Journal of Agricultural and Food Chemistry, 49(1), 2–8. 10.1021/jf990928e
  • Fadel, O., El Kirat, K., & Morandat, S. (2011). The natural antioxidant rosmarinic acid spontaneously penetrates membranes to inhibit lipid peroxidation in situ. Biochimica et Biophysica Acta (BBA) - Biomembranes, 1808(12), 2973–2980. 10.1016/j.bbamem.2011.08.011
  • Fenley, A. T., Henriksen, N. M., Muddana, H. S., & Gilson, M. K. (2014). Bridging calorimetry and simulation through precise calculations of cucurbituril-guest binding enthalpies. Journal of Chemical Theory and Computation, 10(9), 4069–4078. 10.1021/ct5004109
  • Ferlemi, A.-V., Katsikoudi, A., Kontogianni, V. G., Kellici, T. F., Iatrou, G., Lamari, F. N., Tzakos, A. G., & Margarity, M. (2015). Rosemary tea consumption results to anxiolytic- and anti-depressant-like behavior of adult male mice and inhibits all cerebral area and liver cholinesterase activity; phytochemical investigation and in silico studies. Chemico-Biological Interactions, 237, 47–57. 10.1016/j.cbi.2015.04.013
  • Figueiras, A., Carvalho, R. A., Ribeiro, L., Torres-Labandeira, J. J., & Veiga, F. J. (2007). Solid-state characterization and dissolution profiles of the inclusion complexes of omeprazole with native and chemically modified beta-cyclodextrin. European Journal of Pharmaceutics and Biopharmaceutics, 67(2), 531–539. 10.1016/j.ejpb.2007.03.005
  • Friesner, R. A., Murphy, R. B., Repasky, M. P., Frye, L. L., Greenwood, J. R., Halgren, T. A., Sanschagrin, P. C., & Mainz, D. T. (2006). Extra precision glide: Docking and scoring incorporating a model of hydrophobic enclosure for protein − ligand complexes. Journal of Medicinal Chemistry, 49(21), 6177–6196. 10.1021/jm051256o
  • Fukami, T., Ishii, T., Io, T., Suzuki, N., Suzuki, T., Yamamoto, K., Xu, J., Ramamoorthy, A., & Tomono, K. (2009). Nanoparticle processing in the solid state dramatically increases the cell membrane permeation of a cholesterol-lowering drug, probucol. Molecular Pharmaceutics, 6(3), 1029–1035. 10.1021/mp9000487
  • Fung, B. M., Khitrin, A. K., & Ermolaev, K. (2000). An improved broadband decoupling sequence for liquid crystals and solids. Journal of Magnetic Resonance, 142(1), 97–101. 10.1006/jmre.1999.1896
  • Furtado, M. A., de Almeida, L. C., Furtado, R. A., Cunha, W. R., & Tavares, D. C. (2008). Antimutagenicity of rosmarinic acid in Swiss mice evaluated by the micronucleus assay. Mutation Research/Genetic Toxicology and Environmental Mutagenesis, 657(2), 150–154. 10.1016/j.mrgentox.2008.09.003
  • Gülçin, İ. (2006). Antioxidant activity of caffeic acid (3,4-dihydroxycinnamic acid). Toxicology, 217(2–3), 213–220. 10.1016/j.tox.2005.09.011.
  • Genaro-Mattos, T. C., Mauricio, A. Q., Rettori, D., Alonso, A., & Hermes-Lima, M. (2015). Antioxidant activity of caffeic acid against iron-induced free radical generation–a chemical approach. PLoS One, 10(6), e0129963. 10.1371/journal.pone.0129963
  • Gerogianni, P. S., Chatziathanasiadou, M. V., Diamantis, D. A., Tzakos, A. G., & Galaris, D. (2018). Lipophilic ester and amide derivatives of rosmarinic acid protect cells against H2O2-induced DNA damage and apoptosis: The potential role of intracellular accumulation and labile iron chelation. Redox Biology, 15, 548–556. 10.1016/j.redox.2018.01.014
  • Ghaffari, H., Venkataramana, M., Jalali Ghassam, B., Chandra Nayaka, S., Nataraju, A., Geetha, N. P., & Prakash, H. S. (2014). Rosmarinic acid mediated neuroprotective effects against H2O2-induced neuronal cell damage in N2A cells. Life Sciences, 113(1–2), 7–13. 10.1016/j.lfs.2014.07.010
  • Kellici, T. F., Chatziathanasiadou, M. V., Diamantis, D., Chatzikonstantinou, A. V., Andreadelis, I., Christodoulou, E., Valsami, G., Mavromoustakos, T., & Tzakos, A. G. (2016). Mapping the interactions and bioactivity of quercetin-(2-hydroxypropyl)-beta-cyclodextrin complex. International Journal of Pharmaceutics, 511(1), 303–311. 10.1016/j.ijpharm.2016.07.008
  • Kellici, T. F., Ntountaniotis, D., Leonis, G., Chatziathanasiadou, M., Chatzikonstantinou, A. V., Becker-Baldus, J., Glaubitz, C., Tzakos, A. G., Viras, K., Chatzigeorgiou, P., Tzimas, S., Kefala, E., Valsami, G., Archontaki, H., Papadopoulos, M. G., & Mavromoustakos, T. (2015). Investigation of the interactions of silibinin with 2-hydroxypropyl-beta-cyclodextrin through biophysical techniques and computational methods. Molecular Pharmaceutics, 12(3), 954–965. 10.1021/mp5008053
  • Kępa, M., Miklasińska-Majdanik, M., Wojtyczka, R. D., Idzik, D., Korzeniowski, K., Smoleń-Dzirba, J., & Wąsik, T. J. (2018). Antimicrobial potential of caffeic acid against Staphylococcus aureus clinical strains. Biomed Research International, 2018, 1–9. 10.1155/2018/7413504
  • Kollman, P. A., Massova, I., Reyes, C., Kuhn, B., Huo, S., Chong, L., Lee, M., Lee, T., Duan, Y., Wang, W., Donini, O., Cieplak, P., Srinivasan, J., Case, D. A., & Cheatham, T. E. (2000). Calculating structures and free energies of complex molecules: Combining molecular mechanics and continuum models. Accounts of Chemical Research, 33(12), 889–897. 10.1021/ar000033j
  • Lee, H. J., Jeong, Y.-I., Lee, T.-H., Jung, I. D., Lee, J. S., Lee, C.-M., Kim, J.-I., Joo, H., Lee, J.-D., & Park, Y.-M. (2007). Rosmarinic acid inhibits indoleamine 2,3-dioxygenase expression in murine dendritic cells. Biochemical Pharmacology, 73(9), 1412–1421. 10.1016/j.bcp.2006.12.018
  • Li, H., Xu, X., Liu, M., Sun, D., & Li, L. (2010). Microcalorimetric and spectrographic studies on host–guest interactions of α-, β-, γ- and Mβ-cyclodextrin with resveratrol. Thermochimica Acta, 510(1–2), 168–172. 10.1016/j.tca.2010.07.011
  • Li, J., Jiang, Q., Deng, P., Chen, Q., Yu, M., Shang, J., & Li, W. (2017). The formation of a host-guest inclusion complex system between beta-cyclodextrin and baicalin and its dissolution characteristics. Journal of Pharmacy and Pharmacology, 69(6), 663–674. 10.1111/jphp.12708
  • Li, Y., Chen, L. J., Jiang, F., Yang, Y., Wang, X. X., Zhang, Z., Li, Z., & Li, L. (2015). Caffeic acid improves cell viability and protects against DNA damage: Involvement of reactive oxygen species and extracellular signal-regulated kinase. Brazilian Journal of Medical and Biological Research, 48(6), 502–508. 10.1590/1414-431x20143729
  • Liossi, Α. S., Ntountaniotis, D., Kellici, T. F., Chatziathanasiadou, M. V., Megariotis, G., Mania, M., Becker-Baldus, J., Kriechbaum, M., Krajnc, A., Christodoulou, E., Glaubitz, C., Rappolt, M., Amenitsch, H., Mali, G., Theodorou, D. N., Valsami, G., Pitsikalis, M., Iatrou, H., Tzakos, A. G., & Mavromoustakos, T. (2017). Exploring the interactions of irbesartan and irbesartan-2-hydroxypropyl-beta-cyclodextrin complex with model membranes. Biochimica et Biophysica Acta, 1859(6), 1089–1098. 10.1016/j.bbamem.2017.03.003
  • Malanga, M., Szemán, J., Fenyvesi, É., Puskás, I., Csabai, K., Gyémánt, G., Fenyvesi, F., & Szente, L. (2016). “Back to the future”: A new look at hydroxypropyl beta-cyclodextrins. Journal of Pharmaceutical Sciences, 105(9), 2921–2931. 10.1016/j.xphs.2016.04.034
  • Medronho, B., Valente, A. J. M., Costa, P., & Romano, A. (2014). Inclusion complexes of rosmarinic acid and cyclodextrins: Stoichiometry, association constants, and antioxidant potential. Colloid and Polymer Science, 292(4), 885–894. 10.1007/s00396-013-3124-5
  • Mendes, C., Buttchevitz, A., Kruger, J. H., Bernardi, L. S., Oliveira, P. R., & Silva, M. A. (2015). Quantitative analysis of norfloxacin in beta-cyclodextrin inclusion complexes–development and validation of a stability-indicating HPLC method. Analytical Sciences, 31(10), 1083–1089. 10.2116/analsci.31.1083
  • Miller, B. R., 3rd, McGee, T. D., Jr., Swails, J. M., Homeyer, N., Gohlke, H., & Roitberg, A. E. (2012). MMPBSA.py: An efficient program for end-state free energy calculations. Journal of Chemical Theory and Computation, 8(9), 3314–3321. 10.1021/ct300418h
  • Mitropoulou, G., Fitsiou, E., Spyridopoulou, K., Tiptiri-Kourpeti, A., Bardouki, H., Vamvakias, M., Panas, P., Chlichlia, K., Pappa, A., & Kourkoutas, Y. (2017). Citrus medica essential oil exhibits significant antimicrobial and antiproliferative activity. LWT, 84, 344–352. 10.1016/j.lwt.2017.05.036
  • Pierce, M. M., Raman, C. S., & Nall, B. T. (1999). Isothermal titration calorimetry of protein–protein interactions. Methods, 19(2), 213–221. 10.1006/meth.1999.0852
  • Pinho, E., Soares, G., & Henriques, M. (2015). Evaluation of antibacterial activity of caffeic acid encapsulated by beta-cyclodextrins. Journal of Microencapsulation, 32(8), 804–810. 10.3109/02652048.2015.1094531
  • Pitha, J., Milecki, J., Fales, H., Pannell, L., & Uekama, K. (1986). Hydroxypropyl-β-cyclodextrin: Preparation and characterization; effects on solubility of drugs. International Journal of Pharmaceutics, 29(1), 73–82. 10.1016/0378-5173(86)90201-2
  • Qiang, Z., Ye, Z., Hauck, C., Murphy, P. A., McCoy, J.-A., Widrlechner, M. P., Reddy, M. B., & Hendrich, S. (2011). Permeability of rosmarinic acid in Prunella vulgaris and ursolic acid in Salvia officinalis extracts across Caco-2 cell monolayers. Journal of Ethnopharmacology, 137(3), 1107–1112. 10.1016/j.jep.2011.07.037
  • Rajendra Prasad, N., Karthikeyan, A., Karthikeyan, S., & Reddy, B. V. (2011). Inhibitory effect of caffeic acid on cancer cell proliferation by oxidative mechanism in human HT-1080 fibrosarcoma cell line. Molecular and Cellular Biochemistry, 349(1–2), 11–19. 10.1007/s11010-010-0655-7
  • Rocha, J., Eduardo-Figueira, M., Barateiro, A., Fernandes, A., Brites, D., Bronze, R., Duarte, C. M. M., Serra, A. T., Pinto, R., Freitas, M., Fernandes, E., Silva-Lima, B., Mota-Filipe, H., & Sepodes, B. (2015). Anti-inflammatory effect of rosmarinic acid and an extract of Rosmarinus officinalis in rat models of local and systemic inflammation. Basic & Clinical Pharmacology & Toxicology, 116(5), 398–413. 10.1111/bcpt.12335
  • Sfihi, H., Legrand, A. P., Doussot, J., & Guy, A. (1996). Solid-state 13C NMR study of β-cyclodextrin/substituted aromatic ketone complexes: Evidence for two kinds of complexation of the guest molecules. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 115, 115–126. 10.1016/0927-7757(96)03614-x
  • Swarup, V., Ghosh, J., Ghosh, S., Saxena, A., & Basu, A. (2007). Antiviral and anti-inflammatory effects of rosmarinic acid in an experimental murine model of Japanese encephalitis. Antimicrobial Agents and Chemotherapy, 51(9), 3367–3370. 10.1128/AAC.00041-07
  • Tiwari, G., Tiwari, R., & Rai, A. K. (2010). Cyclodextrins in delivery systems: Applications. Journal of Pharmacy and Bioallied Sciences, 2(2), 72–79. 10.4103/0975-7406.67003
  • Trinadha, C., Pitha, J., Lindberg, B., & Lindberg, J. (1992). Distribution of substituents in O-(2-hydroxypropyl) derivatives of cyclomalto-oligosaccharides (cyclodextrins: Influence of increasing substitution of the base used in the preparation, and of macrocyclic size. Carbohydrate Research, 223, 99–107. 10.1016/0008-6215(92)80009-P
  • Vinayagam, R., Jayachandran, M., & Xu, B. (2016). Antidiabetic effects of simple phenolic acids: A comprehensive review. Phytotherapy Research, 30(2), 184–199. 10.1002/ptr.5528
  • Vujicic, M., Nikolic, I., Kontogianni, V. G., Saksida, T., Charisiadis, P., Orescanin-Dusic, Z., Blagojevic, D., Stosic-Grujicic, S., Tzakos, A. G., & Stojanovic, I. (2015). Methanolic extract of Origanum vulgare ameliorates type 1 diabetes through antioxidant, anti-inflammatory and anti-apoptotic activity. British Journal of Nutrition, 113(5), 770–782. 10.1017/S0007114514004048
  • Wang, S. J., Zeng, J., Yang, B. K., & Zhong, Y. M. (2014). Bioavailability of caffeic acid in rats and its absorption properties in the Caco-2 cell model. Pharmaceutical Biology, 52(9), 1150–1157. 10.3109/13880209.2013.879906
  • Wei, Y., Zhang, J., Zhou, Y., Bei, W., Li, Y., Yuan, Q., & Liang, H. (2017). Characterization of glabridin/hydroxypropyl-β-cyclodextrin inclusion complex with robust solubility and enhanced bioactivity. Carbohydrate Polymers, 159(Supplement C), 152–160. 10.1016/j.carbpol.2016.11.093
  • Wszelaka-Rylik, M., & Gierycz, P. (2015). Isothermal titration calorimetry (ITC) study of natural cyclodextrins inclusion complexes with tropane alkaloids. Journal of Thermal Analysis and Calorimetry, 121(3), 1359–1364. 10.1007/s10973-015-4658-1
  • Zhang, M., Li, J., Zhang, L., & Chao, J. (2009a). Preparation and spectral investigation of inclusion complex of caffeic acid with hydroxypropyl-beta-cyclodextrin. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 71(5), 1891–1895. 10.1016/j.saa.2008.07.014
  • Zhang, M., Li, J., Zhang, L., & Chao, J. (2009b). Preparation and spectral investigation of inclusion complex of caffeic acid with hydroxypropyl-β-cyclodextrin. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 71(5), 1891–1895. 10.1016/j.saa.2008.07.014
  • Zhang, Y., He, L., Yue, S., Huang, Q., Zhang, Y., & Yang, J. (2017). Characterization and evaluation of a self-microemulsifying drug delivery system containing tectorigenin, an isoflavone with low aqueous solubility and poor permeability. Drug Delivery, 24(1), 632–640. 10.1080/10717544.2017.1284946
  • Zheng, Y., Dong, L. N., Liu, M., Chen, A., Feng, S., Wang, B., & Sun, D. (2014). Effect of pH on the complexation of kaempferol-4’-glucoside with three beta-cyclodextrin derivatives: Isothermal titration calorimetry and spectroscopy study. Journal of Agricultural and Food Chemistry, 62(1), 244–250. 10.1021/jf404320w
  • Zhu, F., Asada, T., Sato, A., Koi, Y., Nishiwaki, H., & Tamura, H. (2014). Rosmarinic acid extract for antioxidant, antiallergic, and α-glucosidase inhibitory activities, isolated by supramolecular technique and solvent extraction from perilla leaves. Journal of Agricultural and Food Chemistry, 62(4), 885–892. 10.1021/jf404318j

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