Advanced Spectroscopic Detectors for Identification and Quantification: Nuclear Magnetic Resonance

Liquid Chromatography: Fundamentals and Instrumentation

Volumn , Issue , 2013, Pages 349-384

  Wolfender, J L ^a   Bohni, N ^a   Ndjoko Ioset, K ^a   Edison, A S ^b  

^a UNIVERSITY OF GENEVA   (Switzerland)

^b UNIVERSITY OF FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84901879965     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-12-415807-8.00016-X     Document Type: Chapter

References (81)

1. Wolfender J.-L. HPLC in natural product analysis: the detection issue. Planta Med 2009, 75:719-734.
2. Jaroszewski J.W. Hyphenated NMR methods in natural products research, part 1: direct hyphenation. Planta Med 2005, 71:691-700.
3. Albert K. On-line LC-NMR and related techniques 2002, John Wiley & Sons, Chichester, UK.
4. Wolfender J.-L. LC-NMR and related techniques for the rapid identification of plant metabolites. High performance liquid chromatography in phytochemical analysis 2010, 287-329. CRC Press, Boca Raton, FL. M. Waksmundzka-Hajnos, J. Sherma (Eds.).
5. Corcoran O., Spraul M. LC-NMR-MS in drug discovery. Drug Discov Today 2003, 8:624-631.
6. Dalisay D.S., Molinski T.F. NMR quantitation of natural products at the nanomole scale. J Nat Prod 2009, 72:739-744.
7. Hoult D.I., Richards R.E. Signal-to-noise ratio of nuclear magnetic-resonance experiment. J Magn Res 1976, 24:71-85.
8. Ardenkjaer-Larsen J.H., Fridlund B., Gram A., Hansson G., Hansson L., Lerche M.H., et al. Increase in signal-to-noise ratio of >10,000 times in liquid-state NMR. Proc Natl Acad Sci U S A 2003, 100:10158-10163.
9. Li Y., Logan T.M., Edison A.S., Webb A. Design of small volume HX and triple-resonance probes for improved limits of detection in protein NMR experiments. J Magn Res 2003, 164:128-135.
10. Gokay O., Albert K. From single to multiple microcoil flow probe NMR and related capillary techniques: a review. Anal Bioanal Chem 2012, 402:647-669.
11. Li Y., Wolters A.M., Malawey P.V., Sweedler J.V., Webb A.G. Multiple solenoidal microcoil probes for high-sensitivity, high-throughput nuclear magnetic resonance spectroscopy. Anal Chem 1999, 71:4815-4820.
12. Wolters A.M., Jayawickrama D.A., Webb A.G., Sweedler J.W. NMR detection with multiple solenoidal microcoils for continuous-flow capillary electrophoresis. Anal Chem 2002, 74:5550-5555.
13. Wang H., Ciobanu L., Edison A.S., Webb A.G. An eight-coil high-frequency probehead design for high-throughput nuclear magnetic resonance spectroscopy. J Magn Res 2004, 170:206-212.
14. Norcross J.A., Milling C.T., Olson D.L., Xu D., Audrieth A., Albrecht R., et al. Multiplexed NMR: an automated CapNMR dual-sample probe. Anal Chem 2010, 82:7227-7236.
15. Kovacs H., Moskau D., Spraul M. Cryogenically cooled probes-a leap in NMR technology. Prog Nucl Magn Res Spec 2005, 46:131-155.
16. Brey W.W., Edison A.S., Nast R.E., Rocca J.R., Saha S., Withers R.S. Design, construction, and validation of a 1-mm triple-resonance high-temperature-superconducting probe for NMR. J Magn Res 2006, 179:290-293.
17. Olson D.L., Norcross J.A., O'Neil-Johnson M., Molitor P.F., Detlefsen D.J., Wilson A.G., et al. Microflow NMR: concepts and capabilities. Anal Chem 2004, 76:2966-2974.
18. Hu J.F., Yoo H.D., Williams C.T., Garo E., Cremin P.A., Zeng L., et al. Miniaturization of the structure elucidation of novel natural products-two trace antibacterial acylated caprylic alcohol glycosides from Arctostaphylos pumila. Planta Med 2005, 71:176-180.
19. Dalisay D.S., Rogers E.W., Edison A.S., Molinski T.F. Structure elucidation at the nanomole scale. 1. Trisoxazole macrolides and thiazole-containing cyclic peptides from the nudibranch Hexabranchus sanguineus. J Nat Prod 2009, 72:732-738.
20. Queiroz E.F., Wolfender J.-L., Atindehou K.K., Traore D., Hostettmann K. On-line identification of the antifungal constituents of Erythrina vogelii by liquid chromatography with tandem mass spectrometry, ultraviolet absorbance detection and nuclear magnetic resonance spectrometry combined with liquid chromatographic micro-fractionation. J Chromatogr A 2002, 974:123-134.
21. Mishkovsky M., Frydman L. Principles and progress in ultrafast multidimensional nuclear magnetic resonance. Annual review of physics and chemistry 2009, 60:429-448.
22. Shockcor J.P., Unger S.E., Savina P., Nicholson J.K., Lindon J.C. Application of directly coupled LC-NMR-MS to the structural elucidation of metabolites of the HIV-1 reverse-transcriptase inhibitor BW935U83. J Chromatogr B 2000, 748:269-279.
23. Smallcombe S.H., Patt S.L., Keiffer P.A. WET solvent suppression and its application to LC-NMR and high-resolution NMR spectroscopy. J Magn Res Series A 1995, 117:295-303.
24. Cavin A., Potterat O., Wolfender J.-L., Hostettmann K., Dyatmyko W. Use of on-flow LC/H-1 NMR for the study of an antioxidant fraction from Orophea enneandra and isolation of a polyacetylene, lignans, and a tocopherol derivative. J Nat Prod 1998, 61:1497-1501.
25. Wilson S.R., Malerod H., Petersen D., Rise F., Lundanes E., Greibrokk T. An alternative multiple-trapping LC-SPE-NMR system. J Sep Sci 2007, 30:322-328.
26. Jaroszewski J.W. Hyphenated NMR methods in natural products research, Part 2: HPLC-SPE-NMR and other new trends in NMR hyphenation. Planta Med 2005, 71:795-802.
27. Clarkson C., Sibum M., Mensen R., Jaroszewski J.W. Evaluation of on-line solid-phase extraction parameters for hyphenated, high-performance liquid chromatography-solid-phase extraction-nuclear magnetic resonance applications. J Chromatogr A 2007, 1165:1-9.
28. Wilson S.R., Malerod H., Petersen D., Simic N., Bobu M.M., Rise F., et al. Controlling LC-SPE-NMR systems. J Sep Sci 2006, 29:582-589.
29. Wolfender J.-L., Queiroz E.F., Hostettmann K. Phytochemistry in the microgram domain-a LC-NMR perspective. Magn Reson Chem 2005, 43:697-709.
30. Lin Y.Q., Schiavo S., Orjala J., Vouros P., Kautz R. Microscale LC-MS-NMR platform applied to the identification of active cyanobacterial metabolites. Anal Chem 2008, 80:8045-8054.
31. Rehbein J., Dietrich B., Grynbaum M.D., Hentschel P., Holtin K., Kuehnle M., et al. Characterization of bixin by LC-MS and LC-NMR. J Sep Sci 2007, 30:2382-2390.
32. Lang G., Mayhudin N.A., Mitova M.I., Sun L., van der Sar S., Blunt J.W., et al. Evolving trends in the dereplication of natural product extracts: new methodology for rapid, small-scale investigation of natural product extracts. J Nat Prod 2008, 71:1595-1599.
33. Schuetz C., Quitschau M., Hamburger M., Potterat O. Profiling of isoflavonoids in Iris germanica rhizome extracts by microprobe NMR and HPLC-PDA-MS analysis. Fitoterapia 2011, 82:1021-1026.
34. Williams R.B., Martin S.M., Hu J.-F., Garo E., Rice S.M., Norman V.L., et al. Isolation of apoptosis-inducing stilbenoids from four members of the Orchidaceae family. Planta Med 2012, 78:160-165.
35. Wilson I.D., Brinkman U.A.T. Hyphenation and hypernation-the practice and prospects of multiple hyphenation. J Chromatogr A 2003, 1000:325-356.
36. Claridge T.D.W. One-dimensional techniques. High-resolution NMR techniques in organic chemistry 2009, 99-128. Elsevier, Oxford, UK. D.W.C. Timothy (Ed.).
37. Pauli G.F., Jaki B.U., Lankin D.C. Quantitative 1H NMR: development and potential of a method for natural products analysis. J Nat Prod 2004, 68:133-149.
38. Godejohann M., Preiss A. Quantitive measurements in continuous flow HPLC/NMR. Anal Chem 1998, 70:590-595.
39. Akoka S., Barantin L., Trierweiler M. Concentration measurement by proton NMR using the ERETIC method. Anal Chem 1999, 71:2554-2557.
40. Farrant R.D., Hollerton J.C., Lynn S.M., Provera S., Sidebottom P.J., Upton R.J. NMR quantification using an artificial signal. Magn Res Chem 2010, 48:753-762.
41. Pierens G.K., Carroll A.R., Davis R.A., Palframan M.E., Quinn R.J. Determination of analyte concentration using the residual solvent resonance in 1H NMR spectroscopy. J Nat Prod 2008, 71:810-813.
42. Wider G., Dreier L. Measuring protein concentrations by NMR spectroscopy. J Am Chem Soc 2006, 128:2571-2576.
43. Kim S.J., Kim S.M., Kim M.C., Kang S.W., Um B.H. Fast identification of flavonoids in the roots of Sophora flavescens by on-flow LC-NMR. J Med Plants Res 2010, 4:2452-2459.
44. Lambert M., Wolfender J.-L., Staerk D., Christensen B., Hostettmann K., Jaroszewski J.W. Identification of natural products using HPLC-SPE combined with CapNMR. Anal Chem 2007, 79:727-735.
45. Glauser G., Guillarme D., Grata E., Boccard J., Thiocone A., Carrupt P.-A., et al. Optimized liquid chromatography-mass spectrometry approach for the isolation of minor stress biomarkers in plant extracts and their identification by capillary nuclear magnetic resonance. J Chromatogr A 2008, 1180:90-98.
46. Glauser G., Gindro K., Fringeli J., de Joffrey J.-P., Rudaz S., Wolfender J.-L. Differential analysis of mycoalexins in confrontation zones of grapevine fungal pathogens by ultra-high pressure liquid chromatography/time-of-flight mass spectrometry and capillary nuclear magnetic resonance. J Agric Food Chem 2009, 57:1127-1134.
47. Sandvoss M., Pham L.H., Levsen K., Preiss A., Mugge C., Wunsch G. Isolation and structural elucidation of steroid oligoglycosides from the starfish Asterias rubens by means of direct online LC-NMR-MS hyphenation and one- and two-dimensional NMR investigations. Eur J Org Chem 2000, 7:1253-1262.
48. Sandvoss M., Weltring A., Preiss A., Levsen K., Wuensch G. Combination of matrix solid-phase dispersion extraction and direct on-line liquid chromatography-nuclear magnetic resonance spectroscopy-tandem mass spectrometry as a new efficient approach for the rapid screening of natural products: application to the total asterosaponin fraction of the starfish Asterias rubens. J Chromatogr A 2001, 917:75-86.
49. Mitova M.I., Murphy A.C., Lang G., Blunt J.W., Cole A.L.J., Ellis G., et al. Evolving trends in the dereplication of natural product extracts, 2. The isolation of chrysaibol, an antibiotic peptaibol from a New Zealand sample of the mycoparasitic fungus Sepedonium chrysospermum. J Nat Prod 2008, 71:1600-1603.
50. Nicholls A.W., Wilson I.D., Godejohann M., Nicholson J.K., Shockcor J.P. Identification of phenacetin metabolites in human urine after administration of phenacetin-(CH3)-H-2: measurement of futile metabolic deacetylation via HPLC/MS-SPE-NMR and HPLC-ToF MS. Xenobiotica 2006, 36:615-629.
51. Dear G.J., Plumb R.S., Sweatman B.C., Parry P.S., Roberts A.D., Lindon J.C., et al. Use of directly coupled ion-exchange liquid chromatography-mass spectrometry and liquid chromatography-nuclear magnetic resonance spectroscopy as a strategy for polar metabolite identification. J Chromatogr B 2000, 748:295-309.
52. Vishwanathan K., Babalola K., Wang J., Espina R., Yu L., Adedoyin A., et al. Obtaining exposures of metabolites in preclinical species through plasma pooling and quantitative NMR: addressing metabolites in safety testing (MIST) guidance without using radiolabeled compounds and chemically synthesized metabolite standards. Chem Res Toxicol 2008, 22:311-322.
53. Cardoza L.A., Almeida V.K., Carr A., Larive C.K., Graham D.W. Separations coupled with NMR detection. TrAC, Trends Anal Chem 2003, 22:766-775.
54. Simpson A.J., Tseng L.-H., Simpson M.J., Spraul M., Braumann U., Kingery W.L., et al. The application of LC-NMR and LC-SPE-NMR to compositional studies of natural organic matter. Analyst 2004, 129:1216-1222.
55. Tode C., Maoka T., Sugiura M. Application of LC-NMR to analysis of carotenoids in foods. J Sep Sci 2009, 32:3659-3663.
56. Kreiss W., Froede R., Moehrle V., Eberz G. Chromatography-bioluminescence coupling reveals surprising bioactivity of inthomycin A. Anal Bioanal Chem 2010, 398:2081-2088.
57. Pendela M., Béni S., Haghedooren E., Van den Bossche L., Noszál B., Van Schepdael A., et al. Combined use of liquid chromatography with mass spectrometry and nuclear magnetic resonance for the identification of degradation compounds in an erythromycin formulation. Anal Bioanal Chem 2012, 402:781-790.
58. Murakami T., Kawasaki T., Takemura A., Fukutsu N., Kishi N., Kusu F. Identification of degradation products in loxoprofen sodium adhesive tapes by liquid chromatography-mass spectrometry and dynamic pressurized liquid extraction-solid-phase extraction coupled to liquid chromatography-nuclear magnetic resonance spectroscopy. J Chromatogr A 2008, 1208:164-174.
59. Provera S., Guercio G., Turco L., Curcuruto O., Alvaro G., Rossi T., et al. Application of LC-NMR to the identification of bulk drug impurities in NK1 antagonist GW597599 (vestipitant). Magn Res Chem 2010, 48:523-530.
60. Seo J., Kang S.-I., Won D., Kim M., Ryu J.-Y., Kang S.-W., et al. Absolute configuration-dependent epoxide formation from isoflavan-4-ol stereoisomers by biphenyl dioxygenase of Pseudomonas pseudoalcaligenes strain KF707. Appl Microbiol Biotech 2011, 89:1773-1782.
61. Corcoran O., Spraul M., Hofmann M., Ismail I.M., Lindon J.C., Nicholson J.K. 750 MHz HPLC-NMR spectroscopic identification of rat microsomal metabolites of phenoxypyridines. J Pharm Biomed Anal 1997, 16:481-489.
62. Robinette S.L., Ajredini R., Rasheed H., Zeinomar A., Schroeder F.C., Dossey A.T., et al. Hierarchical alignment and full resolution pattern recognition of 2D NMR spectra: application to nematode chemical ecology. Anal Chem 2011, 83:1649-1657.
63. Wolfender J.-L., Marti G., Queiroz E.F. Advances in techniques for profiling crude extracts and for the rapid identification of natural products: dereplication, quality control and metabolomics. Curr Org Chem 2010, 14:1808-1832.
64. Brkljaca R., Urban S. Recent advancements in HPLC-NMR and applications for natural product profiling and identification. J Liq Chromatogr Rel Tech 2011, 34:1063-1076.
65. Molinski T.F. NMR of natural products at the "nanomole-scale.". Nat Prod Rep 2010, 27:321-329.
66. Hu J.F., Eldridge G.R., Yu Y.H., O'Neil-Johnson M. High-throughput natural product chemistry methods and the application of the capillary NMR probe. Progr Chem 2008, 20:429-440.
67. Gronquist M., Meinwald J., Eisner T., Schroeder F.C. Exploring uncharted terrain in Nature's structure space using capillary NMR spectroscopy: 13 steroids from 50 fireflies. J Am Chem Soc 2005, 127:10810-10811.
68. Srinivasan J., Kaplan F., Ajredini R., Zachariah C., Alborn H.T., Teal P.E.A., et al. A blend of small molecules regulates both mating and development in Caenorhabditis elegans. Nature 2008, 454:1115-U1146.
69. Dachtler M., Glaser T., Kohler K., Albert K. Combined HPLC-MS and HPLC-NMR on-line coupling for the separation and determination of lutein and zeaxanthin stereoisomers in spinach and in retina. Anal Chem 2001, 73:667-674.
70. Cogne A.L., Queiroz E.F., Marston A., Wolfender J.L., Mavi S., Hostettmann K. On-line identification of unstable iridoids from Jamesbrittenia fodina by HPLC-MS and HPLC-NMR. Phytochem Anal 2005, 16:429-439.
71. Nicholson J.K., Lindon J.C. Systems biology-metabonomics. Nature 2008, 455:1054-1056.
72. Grimes J.H., O'Connell T.M. he application of micro-coil NMR probe technology to metabolomics of urine and serum. J Biomol NMR 2011, 49:297-305.
73. Wolfender J.L., Glauser G., Boccard J., Rudaz S. MS-based plant metabolomic approaches for biomarker discovery. Nat Prod Comm 2009, 4:1417-1430.
74. Eldridge S.L., Korir A.K., Merrywell C.E., Larive C.K. Hyphenated chromatographic techniques in nuclear magnetic resonance spectroscopy. Advances in chromatography 2008, vol. 4:351-390. CRC Press, Boca Raton, FL. N. Grinberg, E. Grushka (Eds.).
75. Espina R., Yu L., Wang J., Tong Z., Vashishtha S., Talaat R., et al. Nuclear magnetic resonance spectroscopy as a quantitative tool to determine the concentrations of biologically produced metabolites: implications in metabolites in safety testing. Chem Res Toxicol 2009, 22:299-310.
76. Do N.M., Olivier M.A., Salisbury J.J., Wager C.B. Application of quantitative 19F and 1H NMR for reaction monitoring and in situ yield determinations for an early stage pharmaceutical candidate. Anal Chem 2011, 83:8766-8771.
77. Mutlib A., Espina R., Atherton J., Wang J., Talaat R., Scatina J., Chandrasekaran A. Alternate strategies to obtain mass balance without the use of radiolabeled compounds: application of quantitative fluorine (19F) nuclear magnetic resonance (NMR) spectroscopy in metabolism studies. Chem Res Toxicol 2012, 25:572-583.
78. Pan C., Liu F., Motto M. Identification of pharmaceutical impurities in formulated dosage forms. J. Pharm. Sci. 2011, 100:1228-1259.
79. Fukutsu N., Kawasaki T., Saito K., Nakazawa H. Application of high-performance liquid chromatography hyphenated techniques for identification of degradation products of cefpodoxime proxetil. J Chromatogr A 2006, 1129:153-159.
80. Murakami T., Kawasaki T., Takemura A., Fukutsu N., Kishi N., Kusu F. Identification of degradation products in loxoprofen sodium adhesive tapes by liquid chromatography-mass spectrometry and dynamic pressurized liquid extraction-solid-phase extraction coupled to liquid chromatography-nuclear magnetic resonance spectroscopy. J Chromatogr A 2008, 1208:164-174.
81. Wolfender J.-L., Queiroz E.F., Hostettmann K. Development and application of LC/NMR techniques to the identification of bioactive natural products. Bioactive natural products; detection, isolation and structural determination 2008, 143-190. CRC Press, London. S.M. Colegate, R.J. Molyneux (Eds.).