1H-NMR as a structural and analytical tool of intra- and intermolecular hydrogen bonds of phenol-containing natural products and model compounds

Molecules

Volumn 19, Issue 9, 2014, Pages 13643-13682

  Charisiadis, Pantelis ^a   Kontogianni, Vassiliki G ^a   Tsiafoulis, Constantinos G ^a   Tzakos, Andreas G ^a   Siskos, Michael ^a   Gerothanassis, Ioannis P ^a  

^a UNIVERSITY OF IOANNINA   (Greece)

Author keywords

1H 13C HMBC; 1H NMR; Chemical shifts; Hydrogen bonding; Natural products; Phenol OH

Indexed keywords

BIOLOGICAL PRODUCT; PHENOL DERIVATIVE; SOLVENT;

CHEMISTRY; CONFORMATION; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; TEMPERATURE;

BIOLOGICAL PRODUCTS; HYDROGEN BONDING; HYDROGEN-ION CONCENTRATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PHENOLS; SOLVENTS; TEMPERATURE;

EID: 84907101342     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules190913643     Document Type: Review

References (75)

1. Jeffrey, G.A.; Sanger, S.W. Hydrogen Bonding in Biological Structures; Springer Verlag: Berlin, Germany, 1991.
2. Scheider, S. Hydrogen Bonding: A Theoretical Perspective; Oxford University Press: New York, NY, USA, 1997.
3. Perrin, C.L.; Nielson, J.B. "Strong" hydrogen bonds in chemistry and biology. Annu. Rev. Phys. Chem. 1997, 48, 511-544.
4. aslide rule: Toward the solution of a long-lasting problem. Acc. Chem. Res. 2009, 42, 33-44.
5. Gunther, H. NMR Spectroscopy: Basic Principles, Concepts and Applications in Chemistry, 2nd ed.; John Wiley & Sons: Hoboken, NJ, USA, 1995.
6. De Dios, A.C. Ab initio calculations of the NMR chemical shift. Prog. Nucl. Magn. Reson. Spectrosc. 1996, 29, 229-278.
7. Casu, B.; Reggiani, M.; Gallo, G.G.; Vigevani, A. Hydrogen bonding and conformation of glucose and polyglucoses in dimethyl-sulphoxide solution. Tetrahedron 1966, 22, 3061-3083.
8. Poppe, L.; van Halbeek, H. NMR spectroscopy of hydroxyl protons in supercooled carbohydrates. Nat. Struct. Mol. Biol. 1994, 1, 215-216.
9. Adams, B.; Lerner, L. Observation of hydroxyl protons of sucrose in aqueous solution: No evidence for persistent intramolecular hydrogen bonds. J. Am. Chem. Soc. 1992, 114, 4827-4829.
10. Bekiroglu, S.; Sandström, A.; Kenne, L.; Sandström, C. Ab initio and NMR studies on the effect of hydration on the chemical shift of hydroxy protons in carbohydrates using disaccharides and water/methanol/ethers as model systems. Org. Biomol. Chem. 2004, 2, 200-205.
11. Shapetko, N.N.; Shigorin, D.N. NMR study of intramolecular hydrogen bond protons in quinoid structures. J. Struct. Chem. 1967, 8, 474-476.
12. Hansen, P.E.; Spanget-Larsen, J. NMR and IR Spectroscopy of Phenols. In Chemistry of Phenols; Rappoport, Z., Ed.; John Wiley & Sons: Hoboken, NJ, USA, 2003.
13. Eigen, M. Proton transfer, acid-base catalysis, and enzymatic hydrolysis. Part I: Elementary processes. Angew. Chem. Int. Ed. 1964, 3, 1-19.
14. Englander, S.W.; Kallenbach, N.R. Hydrogen exchange and structural dynamics of proteins and nucleic acids. Q. Rev. Biophys. 1983, 16, 521-655.
15. Wuthrich, K. NMR of Proteins and Nucleic Acids; John Wiley & Sons: Hoboken, NJ, USA, 1986.
16. 1H-NMR spectroscopic analysis of plant extracts. J. Nat. Prod. 2011, 74, 2462-2466.
17. Charisiadis, P.; Exarchou, V.; Troganis, A.N.; Gerothanassis, I.P. Exploring the "forgotten" -OH-NMR spectral region in natural products. Chem. Commun. 2010, 46, 3589-3591.
18. Singh, N.; Ahmadd, A. Spectrophotometric and spectroscopic studies of charge transfer complex of 1-naphthylamine as an electron donor with picric acid as an electron acceptor in different polar solvents. J. Mol. Struct. 2010, 977, 197-202.
19. aawska, E.; Stürzebecher, J.; Oleksyn, B.J. Geometry of GPPE binding to picrate and to the urokinase type plasminogen activator. Biorg. Med. Chem. Lett. 2007, 17, 6212-6215.
20. 13C GE-HSQC and GE-HMBC-NMR studies of flavonols and flavones in organic and aqueous mixtures. Tetrahedron 2002, 58, 7423-7429.
21. Tolstoy, P.M.; Koeppe, B.; Denisov, G.S.; Limbach, H.H. Combined NMR and UV-vis spectroscopy in the solution state: Study of the geometries of strong OHO hydrogen bonds of phenols with carboxylic acids. Angew. Chem. Int. Ed. 2009, 48, 5745-5747.
22. Koeppe, B.; Tolstoy, P.M.; Limbach, H.-H. Reaction pathways of proton transfer in hydrogen-bonded phenol-carboxylate complexes explored by combined UV-vis and NMR spectroscopy. J. Am. Chem. Soc. 2011, 133, 7897-7908.
23. Koeppe, B.; Guo, J.; Tolstoy, P.M.; Denisov, G.S.; Limbach, H.H. Solvent and H/D isotope effects on the proton transfer pathways in heteroconjugated hydrogen-bonded phenol-carboxylic acid anions observed by the combined UV-vis and NMR spectroscopy. J. Am. Chem. Soc. 2013, 135, 7553-7566.
24. 2solution. Magn. Reson. Chem. 2001, 39, S91-S99.
25. 1H-NMR shieldings and -OH diffusion coefficients. Org. Biomol. Chem. 2013, 11, 1013-1025.
26. Porte, A.L.; Gutowsky, H.S.; Hunsberger, I.M. The determination of double-bond character in cyclic systems. V. Proton chemical shifts in chelated derivatives of benzene, naphthalene and phenanthrene. J. Am. Chem. Soc. 1960, 82, 5057-5063.
27. 1H-NMR chemical shifts. J. Chem. Soc. Perkin Trans. 2 1997, 945-952. doi:10.1039/A606862F.
28. Gilli, G.; Bellucci, F.; Ferretti, V.; Bertolasi, V. Evidence for resonance-assisted hydrogen bonding from crystal-structure correlations on the enol form of the β-diketone fragment. J. Am. Chem. Soc. 1989, 111, 1023-1028.
29. Falk, H.; Roth, L. From the photosensitizer hypericin to the photoreceptor stentorin-the chemistry of phenantroperylene quinines. Angew. Chem. Int. Ed. 1999, 38, 3117-3136.
30. Vogel, G. How the body's "garbage disposal" may inactivate drugs. Science 2001, 291, 35-37.
31. 1H-NMR. Tetrahedron 2002, 58, 4925-4929.
32. Dax, T.G.; Falk, H.; Kapinus, E.I. Ein nachweis für die struktur des 1,6-dioxo-tautomeren des hypericin. Monatch. Chem. 1999, 130, 827-831.
33. Smirnov, A.; Fulton, D.B.; Andreotti, A.; Petrich, J.W. Exploring ground-state heterogeneity of hypericin and hypocrellin A and B: Dynamic and 2D ROESY NMR study. J. Am. Chem. Soc. 1999, 121, 7979-7988.
34. Freeman, D.; Frolow, F.; Kapinus, D.; Lavie, B.; Lavie, G.; Meruelo, D.; Mazur, Y. Acidic properties of hypericin and its octahydroxy analogue in the ground and excited states. J. Chem. Soc. Chem. Commun. 1994, 7, 891-892.
35. Harris, T.K.; Zhao, Q.; Mildvan, A.S. NMR studies of strong hydrogen bonds in enzymes and in a model compound. J. Mol. Struct. 2000, 552, 97-109.
36. Harris, T.K.; Mildvan, A.S. High-precision measurement of hydrogen bond lengths in proteins by nuclear magnetic resonance methods. Proteins 1999, 35, 275-282.
37. 5-3-ketosteroid isomerase. Biochemistry 1997, 36, 14614-14626.
38. McDermott, A.; Ridenour, C.F. In proton chemical shift measurements in biological solids. In Encyclopedia of Nuclear Magnetic Resonance; Wiley: Sussex, England, 1996; pp. 3820-3825.
39. Yoshimi, Y.; Maeda, H.; Hatanaka, M.; Mizuno, K. Intramolecular 9-membered hydrogen bonding of 2-arylmethylphenols having carbonyl groups at 2′-position. Tetrahedron 2004, 60, 9425-9431.
40. Castelano, R.K.; Li, Y.; Homan, E.A.; Lampkins, A.J.; Marín, I.V.; Abboud, K.A. Seven-membered intramolecular hydrogen bonding of phenols: Database analysis and phloroglucinol model compounds. Eur. J. Org. Chem. 2012, 2012, 4483-4492.
41. 1H-NMR shieldings. Org. Biomol. Chem. 2013, 11, 7400-7411.
42. Saenger, W.; Betzel, C.; Hingerty, B.; Brown, G.M. Flip-flop hydrogen bonding in a partially disordered system. Nature 1982, 296, 581-583.
43. Domagala, S.; Munshi, P.; Ahmed, M.; Guillot, B.; Jelsch, C. Structural analysis and multipole modelling of quercetin monohydrate-A quantitative and comparative study. Acta Crystallogr. Sect. B Struct. Sci. 2011, 67, 63-78.
44. 1H chemical shifts and hydrogen bonding in phenols. Magn. Reson. Chem. 2007, 45, 865-877.
45. 17O NMR-chemical shifts for water. The limits of PCM theory and the role of hydrogen-bond geometry and cooperativity. J. Phys. Chem. A 2004, 108, 5851-5863.
46. Becke, A.D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 1993, 98, 5648-5652.
47. 1H spin-spin coupling to hydroxyl-protons, a complementary assignment aid. J. Chem. Soc. Chem. Commun. 1975, 16, 663-664.
48. Hansen, P.E. Carbon-hydrogen spin-spin coupling constants. Prog. NMR Spectrosc. 1981, 14, 175-295.
49. Borisov, E.V.; Agrawal, P. Keto-enol tautomerism in 2-acetyltetralone: A reinvestigation. Magn. Reson. Chem. 1994, 32, 499-499.
50. 1H) coupling constants of intramolecularly hydrogen-bonded compounds. Magn. Reson. Chem. 1998, 36, 5104-5110.
51. 17O-NMR. Helv. Chim. Acta 1986, 69, 1469-1485.
52. Gerothanassis, I.P. Oxygen-17 NMR spectroscopy: Basic principles and applications (Part II). Prog. NMR Spectrosc. 2010, 57, 1-110.
53. Gerothanassis, I.P. Oxygen-17 NMR spectroscopy: Basic principles and applications (Part I). Progr. NMR Spectrosc. 2010, 56, 95-197.
54. Cohen, Y.; Avram, L.; Frish, L. Diffusion NMR spectroscopy in supramolecular and combinatorial chemistry: An old parameter-new insights. Angew. Chem. Int. Ed. 2005, 44, 520-554.
55. Primikyri, A.; Kyriakou, E.; Charisiadis, P.; Tsiafoulis, C.; Tzakos, A.G.; Gerothanassis, I.P. Fine-tuning of the diffusion dimension of -OH groups for high resolution DOSY NMR applications in crude enzymatic transformations and mixtures of organic compounds. Tetrahedron 2012, 68, 6887-6891.
56. Hong, Y.S.; Hong, K.S.; Cho, J.H.; Volkov, V.I.; Lee, C.H. Chemical exchange of hydroxyl protons in quercetin measured by pulsed field gradient NMR. Appl. Magn. Reson. 2008, 35, 261-270.
57. Bolvig, S.; Hansen, P.E. Isotope effects on chemical shifts as an analytical tool in structural studies of intramolecular hydrogen bonded compounds. Curr. Org. Chem. 2000, 4, 19-54.
58. Etzlstorfer, C.; Falk, H.; Mayr, E.; Schwarzinger, S. Concerning the acidity and hydrogen bonding of hydroxyphenanthroperylene quinones like fringelite D, hypericin, and stentorian. Monatch. Chem. 1996, 127, 1229-1237.
59. Albert, K. On Line LC-NMR and Related Techniques; John Wiley & Sons: Hoboken, NJ, USA 2002.
60. Hostettmann, K.; Wolfender, J.L. Bioactive Compounds from Natural Sources-Isolation, Characterization and Biological Properties; Tringali, C., Ed.; Taylor & Francis: New York, NY, USA, 2004.
61. Exarchou, V.; Godejohann, M.; van Beek, T.A.; Gerothanassis, I.P.; Vervoort, J. LC-UV-solid phase extraction-NMR-MS combined with a cryogenic flow probe and its application to the identification of compounds present in Greek oregano. Anal. Chem. 2003, 75, 6288-6294.
62. Exarchou, V.; Krucker, M.; van Beek, T.A.; Vervoort, J.; Gerothanassis, I.P.; Albert, K. LC-NMR coupling technology: Recent advancements and applications in natural products analysis. Magn. Reson. Chem. 2005, 43, 681-687.
63. 13C-NMR spectra. Anal. Chem. 2007, 79, 9385-9390.
64. 13C HMBC gradient enhanced NMR spectroscopy: Application to methanolic extracts of several oregano species. J. Agric. Food Chem. 2001, 49, 2-8.
65. Kontogianni, V.G.; Exarchou, V.; Troganis, A.; Gerothanassis, I.P. Rapid and novel discrimination and quantification of oleanolic and ursolic acids in complex plant extracts using two-dimensional nuclear magnetic resonance spectroscopy-comparison with HPLC methods. Anal. Chim. Acta 2009, 635, 188-195.
66. Novoa-Carballal, R.; Fernandez-Megia, E.; Jimenez, C.; Riguera, R. NMR methods for unravelling the spectra of complex mixtures. Nat. Prod. Rep. 2011, 28, 78-98.
67. Robinette, S.L.; Brüschweiler, R.; Schroeder, F.C.; Edison, A.S. NMR in metabolomics and natural products research: Two sides of the same coin. Acc. Chem. Res. 2012, 45, 288-297.
68. Charisiadis, P.; Tsiafoulis, C.G.; Exarchou, V.; Tzakos, A.G.; Gerothanassis, I.P. Rapid and direct low micromolar NMR method for the simultaneous detection of hydrogen peroxide and phenolics in plant extracts. J. Agric. Food Chem. 2012, 60, 4508-4513.
69. Kyriakou, E.; Primikyri, A.; Charisiadis, P.; Katsoura, M.; Gerothanassis, I.P.; Stamatis, H.; Tzakos, A.G. Unexpected enzyme-catalyzed regioselective acylation of flavonoid aglycones and rapid product screening. Org. Biomol. Chem. 2012, 10, 1739-1742.
70. 1H-NMR of the -OH spectral region. Anal. Chim. Acta 2011, 688, 54-60.
71. Tsiafoulis, C.; Gerothanassis, I.P. A novel NMR method for the determination and monitoring of evolution of hydrogen peroxide in aqueous solution. Anal. Bioanal. Chem. 2014, 406, 3371-3375.
72. 1H-NMR determination of hypericin and pseudohypericin in complex natural mixtures by the use of strongly deshielded OH groups. Anal. Chim. Acta 2008, 607, 219-226.
73. Tatsis, E.C.; Boeren, S.; Exarchou, V.; Troganis, A.N.; Vervoort, J.; Gerothanassis, I.P. Identification of the major constituents of hypericum perforatum by LC/SPE/NMR and/or LC/MS. Phytochemistry 2007, 68, 383-393.
74. 1H-NMR spectra of butane-1,4-diol and other 1,4-diols: DFT calculation of shifts and coupling constants. Magn. Reson. Chem. 2014, 52, 87-97.
75. 3JCCOH spin-couplings in saccharides: C-O torsional bias and H-bonding in aqueous solution. J. Am. Chem. Soc. 2007, 72, 7071-7082.