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Volumn 194, Issue , 2016, Pages 1156-1163

Interaction of cinnamic acid derivatives with β-cyclodextrin in water: Experimental and molecular modeling studies

Author keywords

Cinnamic acid derivatives (CAs); Inclusion complex; ONIOM (our Own N layer Integrated Orbital molecular Mechanics) calculations; Cyclodextrin ( CD)

Indexed keywords

CYCLODEXTRINS; MECHANICS; MOLECULAR MECHANICS; MOLECULAR MODELING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORBITAL CALCULATIONS; QUANTUM THEORY; SOLUBILITY; SOLUTIONS;

EID: 84941335155     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2015.09.001     Document Type: Article
Times cited : (43)

References (40)
  • 3
    • 0031209054 scopus 로고    scopus 로고
    • A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics
    • E. Cancès, B. Mennucci, and J. Tomasi A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics Journal of Chemical Physics 107 1997 3032 3041
    • (1997) Journal of Chemical Physics , vol.107 , pp. 3032-3041
    • Cancès, E.1    Mennucci, B.2    Tomasi, J.3
  • 4
    • 0345179962 scopus 로고    scopus 로고
    • The stability of cyclodextrin complexes in solution
    • K.A. Connors The stability of cyclodextrin complexes in solution Chemical Reviews 97 1997 1325 1357
    • (1997) Chemical Reviews , vol.97 , pp. 1325-1357
    • Connors, K.A.1
  • 5
    • 0033515394 scopus 로고    scopus 로고
    • A new ONIOM implementation in Gaussian98. Part I. The calculation of energies, gradients, vibrational frequencies and electric field derivatives
    • S. Dapprich, I. Komaromi, K.S. Byun, K. Morokuma, and M.J. Frisch A new ONIOM implementation in Gaussian98. Part I. The calculation of energies, gradients, vibrational frequencies and electric field derivatives Journal of Molecular Structure: THEOCHEM 461 1999 1 21
    • (1999) Journal of Molecular Structure: THEOCHEM , vol.461 , pp. 1-21
    • Dapprich, S.1    Komaromi, I.2    Byun, K.S.3    Morokuma, K.4    Frisch, M.J.5
  • 6
    • 66349087989 scopus 로고    scopus 로고
    • Molecular dynamics of large-ring cyclodextrins: Principal component analysis of the conformational interconversions
    • M.G. Gotsev, and P.M. Ivanov Molecular dynamics of large-ring cyclodextrins: Principal component analysis of the conformational interconversions Journal of Physical Chemistry B 113 2009 5752 5759
    • (2009) Journal of Physical Chemistry B , vol.113 , pp. 5752-5759
    • Gotsev, M.G.1    Ivanov, P.M.2
  • 7
    • 84908428984 scopus 로고    scopus 로고
    • Bioactivity of phenolic acids: Metabolites versus parent compounds: A review
    • S.A. Heleno, A. Martins, M.J. Queiroz, and I.C. Ferreira Bioactivity of phenolic acids: Metabolites versus parent compounds: A review Food Chemistry 173 2015 501 513
    • (2015) Food Chemistry , vol.173 , pp. 501-513
    • Heleno, S.A.1    Martins, A.2    Queiroz, M.J.3    Ferreira, I.C.4
  • 8
    • 74849132985 scopus 로고    scopus 로고
    • Structural characterization of the Brooker's merocyanine/beta-cyclodextrin complex using NMR spectroscopy and molecular modeling
    • J.S. Holt Structural characterization of the Brooker's merocyanine/beta-cyclodextrin complex using NMR spectroscopy and molecular modeling Journal of Molecular Structure 965 2010 31 38
    • (2010) Journal of Molecular Structure , vol.965 , pp. 31-38
    • Holt, J.S.1
  • 9
    • 42549121294 scopus 로고    scopus 로고
    • Supramolecular nanoencapsulation as a tool: Solubilization of the anticancer drug trans-dichloro(dipyridine)platinum(II) by complexation with beta-cyclodextrin
    • G. Horvath, T. Premkumar, A. Boztas, E. Lee, S. Jon, and K.E. Geckeler Supramolecular nanoencapsulation as a tool: solubilization of the anticancer drug trans-dichloro(dipyridine)platinum(II) by complexation with beta-cyclodextrin Molecular Pharmaceutics 5 2008 358 363
    • (2008) Molecular Pharmaceutics , vol.5 , pp. 358-363
    • Horvath, G.1    Premkumar, T.2    Boztas, A.3    Lee, E.4    Jon, S.5    Geckeler, K.E.6
  • 11
    • 73349100639 scopus 로고    scopus 로고
    • Comparative evaluation of quercetin, isoquercetin and rutin as inhibitors of alpha-glucosidase
    • Y.Q. Li, F.C. Zhou, F. Gao, J.S. Bian, and F. Shan Comparative evaluation of quercetin, isoquercetin and rutin as inhibitors of alpha-glucosidase Journal of Agricultural and Food Chemistry 57 2009 11463 11468
    • (2009) Journal of Agricultural and Food Chemistry , vol.57 , pp. 11463-11468
    • Li, Y.Q.1    Zhou, F.C.2    Gao, F.3    Bian, J.S.4    Shan, F.5
  • 12
    • 0001696434 scopus 로고    scopus 로고
    • Applications of computational chemistry to the study of cyclodextrins
    • K.B. Lipkowitz Applications of computational chemistry to the study of cyclodextrins Chemical Reviews 98 1998 1829 1873
    • (1998) Chemical Reviews , vol.98 , pp. 1829-1873
    • Lipkowitz, K.B.1
  • 13
    • 84891598077 scopus 로고    scopus 로고
    • Physicochemical characterisation of the supramolecular structure of luteolin/cyclodextrin inclusion complex
    • B. Liu, W. Li, J. Zhao, Y. Liu, X. Zhu, and G. Liang Physicochemical characterisation of the supramolecular structure of luteolin/cyclodextrin inclusion complex Food Chemistry 141 2013 900 906
    • (2013) Food Chemistry , vol.141 , pp. 900-906
    • Liu, B.1    Li, W.2    Zhao, J.3    Liu, Y.4    Zhu, X.5    Liang, G.6
  • 14
    • 84862824954 scopus 로고    scopus 로고
    • Empirical, thermodynamic and quantum-chemical investigations of inclusion complexation between flavanones and (2-hydroxypropyl)-cyclodextrins
    • B. Liu, J. Zhao, Y. Liu, X. Zhu, and J. Zeng Empirical, thermodynamic and quantum-chemical investigations of inclusion complexation between flavanones and (2-hydroxypropyl)-cyclodextrins Food Chemistry 134 2012 926 932
    • (2012) Food Chemistry , vol.134 , pp. 926-932
    • Liu, B.1    Zhao, J.2    Liu, Y.3    Zhu, X.4    Zeng, J.5
  • 15
    • 1942470488 scopus 로고    scopus 로고
    • Cyclodextrins and their uses: A review
    • E.M. Martin Del Valle Cyclodextrins and their uses: A review Process Biochemistry 39 2004 1033 1046
    • (2004) Process Biochemistry , vol.39 , pp. 1033-1046
    • Martin Del Valle, E.M.1
  • 16
    • 79953804077 scopus 로고    scopus 로고
    • Permeation and distribution of ferulic acid and its α-cyclodextrin complex from different formulations in hairless rat skin
    • D. Monti, S. Tampucci, P. Chetoni, S. Burgalassi, V. Saino, and M. Centini C. Anselmi Permeation and distribution of ferulic acid and its α-cyclodextrin complex from different formulations in hairless rat skin AAPS PharmSciTech 12 2011 514 520
    • (2011) AAPS PharmSciTech , vol.12 , pp. 514-520
    • Monti, D.1    Tampucci, S.2    Chetoni, P.3    Burgalassi, S.4    Saino, V.5    Centini, M.6    Anselmi, C.7
  • 17
    • 84908314961 scopus 로고    scopus 로고
    • Analytical techniques for characterization of cyclodextrin complexes in aqueous solution: A review
    • P. Mura Analytical techniques for characterization of cyclodextrin complexes in aqueous solution: A review Journal of Pharmaceutical and Biomedical Analysis 101 2014 238 250
    • (2014) Journal of Pharmaceutical and Biomedical Analysis , vol.101 , pp. 238-250
    • Mura, P.1
  • 18
    • 67650045767 scopus 로고    scopus 로고
    • Validating a strategy for molecular dynamics simulations of cyclodextrin inclusion complexes through single-crystal X-ray and NMR experimental data: A case study
    • G. Raffaini, F. Ganazzoli, L. Malpezzi, C. Fuganti, G. Fronza, W. Panzeri, and A. Mele Validating a strategy for molecular dynamics simulations of cyclodextrin inclusion complexes through single-crystal X-ray and NMR experimental data: A case study The Journal of Physical Chemistry B 113 2009 9110 9122
    • (2009) The Journal of Physical Chemistry B , vol.113 , pp. 9110-9122
    • Raffaini, G.1    Ganazzoli, F.2    Malpezzi, L.3    Fuganti, C.4    Fronza, G.5    Panzeri, W.6    Mele, A.7
  • 19
    • 0011083499 scopus 로고
    • Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint
    • A.E. Reed, L.A. Curtiss, and F. Weinhold Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint Chemical Reviews 88 1988 899 926
    • (1988) Chemical Reviews , vol.88 , pp. 899-926
    • Reed, A.E.1    Curtiss, L.A.2    Weinhold, F.3
  • 20
    • 0038408778 scopus 로고    scopus 로고
    • Phenolic acids in foods: An overview of analytical methodology
    • R.J. Robbins Phenolic acids in foods: An overview of analytical methodology Journal of Agricultural and Food Chemistry 51 2003 2866 2887
    • (2003) Journal of Agricultural and Food Chemistry , vol.51 , pp. 2866-2887
    • Robbins, R.J.1
  • 21
    • 84912557560 scopus 로고    scopus 로고
    • Preferential molecular encapsulation of an ICT fluorescence probe in the supramolecular cage of cucurbit[7]uril and β-cyclodextrin: An experimental and theoretical approach
    • A. Samanta, N. Guchhait, and S.C. Bhattacharya Preferential molecular encapsulation of an ICT fluorescence probe in the supramolecular cage of cucurbit[7]uril and β-cyclodextrin: An experimental and theoretical approach The Journal of Physical Chemistry B 118 2014 13279 13289
    • (2014) The Journal of Physical Chemistry B , vol.118 , pp. 13279-13289
    • Samanta, A.1    Guchhait, N.2    Bhattacharya, S.C.3
  • 22
  • 23
    • 84920973064 scopus 로고    scopus 로고
    • Antioxidant and DNA damage protection potentials of selected phenolic acids
    • K. Sevgi, B. Tepe, and C. Sarikurkcu Antioxidant and DNA damage protection potentials of selected phenolic acids Food and Chemical Toxicology 77 2015 12 21
    • (2015) Food and Chemical Toxicology , vol.77 , pp. 12-21
    • Sevgi, K.1    Tepe, B.2    Sarikurkcu, C.3
  • 25
    • 84861227064 scopus 로고    scopus 로고
    • Theoretical study on chiral recognition mechanism of methyl mandelate enantiomers on permethylated β-cyclodextrin
    • J.H. Shi, Z.J. Ding, and Y. Hu Theoretical study on chiral recognition mechanism of methyl mandelate enantiomers on permethylated β-cyclodextrin Journal of Molecular Modeling 18 2012 803 813
    • (2012) Journal of Molecular Modeling , vol.18 , pp. 803-813
    • Shi, J.H.1    Ding, Z.J.2    Hu, Y.3
  • 26
    • 30244527819 scopus 로고    scopus 로고
    • How does basis set superposition error change the potential surfaces for hydrogen bonded dimers?
    • S. Simon, M. Duran, and J.J. Dannenberg How does basis set superposition error change the potential surfaces for hydrogen bonded dimers? The Journal of Chemical Physics 105 1996 11024 11031
    • (1996) The Journal of Chemical Physics , vol.105 , pp. 11024-11031
    • Simon, S.1    Duran, M.2    Dannenberg, J.J.3
  • 27
    • 42649106457 scopus 로고    scopus 로고
    • Effect of β-cyclodextrin on antioxidant activity of coumaric acids
    • M. Stražišar, S. Andrenšek, and A. Šmidovnik Effect of β-cyclodextrin on antioxidant activity of coumaric acids Food Chemistry 110 2008 636 642
    • (2008) Food Chemistry , vol.110 , pp. 636-642
    • Stražišar, M.1    Andrenšek, S.2    Šmidovnik, A.3
  • 28
    • 0346461917 scopus 로고    scopus 로고
    • Introduction and general overview of cyclodextrin chemistry
    • J. Szejtli Introduction and general overview of cyclodextrin chemistry Chemical Reviews 98 1998 1743 1753
    • (1998) Chemical Reviews , vol.98 , pp. 1743-1753
    • Szejtli, J.1
  • 29
    • 79955700916 scopus 로고    scopus 로고
    • Ascorbic acid, phenolic acid, flavonoid, and carotenoid profiles of selected extracts from Ribes nigrum
    • J. Tabart, C. Kevers, D. Evers, and J. Dommes Ascorbic acid, phenolic acid, flavonoid, and carotenoid profiles of selected extracts from Ribes nigrum Journal of Agricultural and Food Chemistry 59 2011 4763 4770
    • (2011) Journal of Agricultural and Food Chemistry , vol.59 , pp. 4763-4770
    • Tabart, J.1    Kevers, C.2    Evers, D.3    Dommes, J.4
  • 30
    • 84868563783 scopus 로고    scopus 로고
    • 2D solid-state NMR analysis of inclusion in drug-cyclodextrin complexes
    • F.G. Vogt, and M. Strohmeier 2D solid-state NMR analysis of inclusion in drug-cyclodextrin complexes Molecular Pharmaceutics 9 2012 3357 3374
    • (2012) Molecular Pharmaceutics , vol.9 , pp. 3357-3374
    • Vogt, F.G.1    Strohmeier, M.2
  • 31
    • 77956619465 scopus 로고    scopus 로고
    • Characterisation of inclusion complex of trans-ferulic acid and hydroxypropyl-b-cyclodextrin
    • J. Wang, Y. Cao, B. Sun, and C. Wang Characterisation of inclusion complex of trans-ferulic acid and hydroxypropyl-b-cyclodextrin Food Chemistry 124 2011 1069 1075
    • (2011) Food Chemistry , vol.124 , pp. 1069-1075
    • Wang, J.1    Cao, Y.2    Sun, B.3    Wang, C.4
  • 32
    • 69249157246 scopus 로고    scopus 로고
    • Study on the complexation of isoquercitrin with β-cyclodextrin and its derivatives by spectroscopy
    • Y. Wang, X. Qiao, W. Li, Y. Zhou, Y. Jiao, and C. Yang S. Shuang Study on the complexation of isoquercitrin with β-cyclodextrin and its derivatives by spectroscopy Analytica Chimica Acta 650 2009 124 130
    • (2009) Analytica Chimica Acta , vol.650 , pp. 124-130
    • Wang, Y.1    Qiao, X.2    Li, W.3    Zhou, Y.4    Jiao, Y.5    Yang, C.6    Shuang, S.7
  • 33
    • 34047205388 scopus 로고    scopus 로고
    • Effect of heat treatment on the phenolic compounds and antioxidant capacity of citrus peel extract
    • G. Xu, X. Ye, J. Chen, and D. Liu Effect of heat treatment on the phenolic compounds and antioxidant capacity of citrus peel extract Journal of Agricultural and Food Chemistry 55 2007 330 335
    • (2007) Journal of Agricultural and Food Chemistry , vol.55 , pp. 330-335
    • Xu, G.1    Ye, X.2    Chen, J.3    Liu, D.4
  • 34
    • 51649096578 scopus 로고    scopus 로고
    • Theoretical study for quercetin/β-cyclodextrin complexes: Quantum chemical calculations based on the PM3 and ONIOM2 method
    • C. Yan, Z. Xiu, X. Li, H. Teng, and C. Hao Theoretical study for quercetin/β-cyclodextrin complexes: quantum chemical calculations based on the PM3 and ONIOM2 method Journal of Inclusion Phenomena and Macrocyclic Chemistry 58 2007 337 344
    • (2007) Journal of Inclusion Phenomena and Macrocyclic Chemistry , vol.58 , pp. 337-344
    • Yan, C.1    Xiu, Z.2    Li, X.3    Teng, H.4    Hao, C.5
  • 36
    • 84884288497 scopus 로고    scopus 로고
    • Cyclodextrin-based supramolecular systems for drug delivery: Recent progress and future perspective
    • J. Zhang, and P.X. Ma Cyclodextrin-based supramolecular systems for drug delivery: Recent progress and future perspective Advanced Drug Delivery Reviews 65 2013 1215 1233
    • (2013) Advanced Drug Delivery Reviews , vol.65 , pp. 1215-1233
    • Zhang, J.1    Ma, P.X.2
  • 37
    • 43049141516 scopus 로고    scopus 로고
    • The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: Two new functionals and systematic testing of four M06-class functionals and 12 other functionals
    • Y. Zhao, and D. Truhlar The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals Theoretical Chemistry Accounts 120 2008 215 241
    • (2008) Theoretical Chemistry Accounts , vol.120 , pp. 215-241
    • Zhao, Y.1    Truhlar, D.2
  • 38
    • 74849127611 scopus 로고    scopus 로고
    • Identification of cyclodextrin inclusion complex of chlorogenic acid and its antimicrobial activity
    • M. Zhao, H. Wang, B. Yang, and H. Tao Identification of cyclodextrin inclusion complex of chlorogenic acid and its antimicrobial activity Food Chemistry 120 2010 1138 1142
    • (2010) Food Chemistry , vol.120 , pp. 1138-1142
    • Zhao, M.1    Wang, H.2    Yang, B.3    Tao, H.4
  • 39
    • 0013602932 scopus 로고
    • Activation hardness - New index for describing the orientation of electrophilic aromatic-substitution
    • Z.X. Zhou, and R.G. Parr Activation hardness - New index for describing the orientation of electrophilic aromatic-substitution Journal of the American Chemical Society 112 1990 5720 5724
    • (1990) Journal of the American Chemical Society , vol.112 , pp. 5720-5724
    • Zhou, Z.X.1    Parr, R.G.2


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