Quantitative 1H NMR: Development and potential of a method for natural products analysis

Journal of Natural Products

Volumn 68, Issue 1, 2005, Pages 133-149

  Pauli, Guido F ^a   Jaki, Birgit U ^a   Lankin, David C ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; NATURAL PRODUCT; BIOLOGICAL PRODUCT;

ANALYTIC METHOD; EXPERIMENTAL DESIGN; INFORMATION PROCESSING; MICROORGANISM; NUCLEAR MAGNETIC RESONANCE; PARAMETER; QUALITATIVE ANALYSIS; QUANTITATIVE ANALYSIS; REVIEW; STEREOISOMERISM; VALIDATION PROCESS; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

BIOLOGICAL PRODUCTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

EID: 12944265405     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np0497301     Document Type: Review

References (195)

1. Tulp, M.; Bohlin, L. Trends Pharmacal. Sci. 2002, 23, 225-231.
2. Cordell, G. A.; Quinn-Beattie, M. L.; Farnsworth, N. R. Phytother. Res. 2001, 15, 183-205.
3. Cordell, G. A. Phytochemistry 2000, 55, 463-480.
4. Cragg, G. M.; Newman, D. J.; Snader, K. M. J. Nat. Prod. 1997, 60, 52-60.
5. Newman, D. J.; Cragg, G. M.; Snader, K. M. J. Nat. Prod. 2003, 66, 1022-1037.
6. Kinghorn, A. D. J. Pharm. Pharmacol. 2001, 53, 135-148.
7. Manly, S. P.; Padmanabha, R.; Lowe, S. E. Methods Mol. Biol. 2002, 190, 153-168.
8. Grabley, S.; Sattler, I. Natural Products for Lead Identification: Nature is a Valuable Resource for Providing Tools; Hillisch, A., Hilgenfeld, R., Eds.; Springer: New York, 2003; Vol. 93, pp 87-107.
9. Bindseil, K. U.; Jakupovic, J.; Wolf, D.; Lavayre, J.; Leboul, J.; van der Pyl, D. Drug Discovery Today 2001, 6, 840-847.
10. Khosla, C.; Keasling, J. D. Nat. Rev. Drug Discovery 2003, 2, 1019-1025.
11. Liao, Y.; Hu, Y.; Wu, J.; Zhu, Q.; Donovan, M.; Fathi, R.; Yang, Z. Curr. Med. Chem. 2003, 10, 2285-316.
12. Tietze, L. F.; Bell, H. P.; Chandrasekhar, S. Angew. Chem., Int. Ed. 2003, 42, 3996-4028.
13. Tulp, M.; Bohlin, L. Drug Discovery Today 2004, 9, 450-458.
14. Keifer, P. Varian NMR Workshop Series: Small Volume Probes and Their Applications; Varian Inc.: Palo Alto, CA, 1999.
15. Pauli, G. F. Phytochem. Anal. 2001, 12, 28-42.
16. Purcell, E. M.; Torrey, H. C.; Pound, R. V. Phys. Rev. 1946, 69, 37-38.
17. Bloch, F.; Hansen, W. W.; Packard, M. Phys. Rev. 1946, 69, 127.
18. Jeener, J. Ampere International Summer School (Basko, Yugoslavia): Two-dimensional NMR spectroscopy was first suggested conceptually by Jeener at an Ampere International Summer School held in Yugoslavia in 1971. Unfortunately, Jeener's first presentation was never published. Indeed, it was not until 1975 that the concept was experimentally realized. The first published experiments were by W. P. Aue, E. Bartholid, and R. R. Ernst (ref 19). This accomplishment was one contribution for which Professor R. R. Ernst received the Nobel Prize in Chemistry in 1991.
19. Aue, W. P.; Bartholdi, E.; Ernst, R. R. J. Chem. Phys. 1976, 64, 2229-2246.
20. Reynolds, W. F.; Enriquez, R. G. J. Nat. Prod. 2002, 65, 221-244.
21. Jaspars, M. Nat. Prod. Rep. 1999, 16, 241-248.
22. Martin, G.; Crouch, R. J. Nat. Prod. 1991, 54, 1-70.
23. Martin, G. E.; Crouch, R. C.; Sharaf, M. H. M.; Schiff, P. L. J. Nat. Prod. 1996, 59, 2-4.
24. Martin, G. E.; Guido, J. E.; Robins, R. H.; Sharaf, M. H. M.; Schiff, P. L., Jr.; Tackie, A. N. J. Nat. Prod. 1998, 61, 555-559.
25. Martin, G. E.; Hadden, C. E. J. Nat. Prod. 2000, 63, 543-585.
26. Pinciroli, V.; Biancardi, R.; Visentin, G.; Rizzo, V. Org. Proc. Res. Dev. 2004, 8, 381-384.
27. Claridge, T. D. W. High-resolution NMR Techniques in Organic Chemistry; Pergamon: New York, 1999.
28. Derome, A. E. Modern NMR Techniques for Chemistry Research: Pergamon Press: New York, 1987.
29. Malz, F. Quantitative NMR-Spektroskopie als Referenzverfahren in der analytischen Chemie. Ph.D. Dissertation, Humboldt-Universität Berlin, Berlin, 2003, 147 pp.
30. Szantay, C. Trends Anal. Chem. 1992, 11, 332-344.
31. Evilia, R. F. Anal. Lett. 2001, 34, 2227-2236.
32. Goldwitz, B. A.; Turczan, J. W. J. Pharrn. Sci. 1973, 62, 115-117.
33. Romano, A., Jr.; Turczan, J.; Polito, M. V. J. Assoc. Off. Anal. Chem. 1965, 48, 1066-1067.
34. Turczan, J. W.; Kram, T. C. J. Pharm. Sci. 1967, 56, 1643-1645.
35. Turczan, J. W. JAOAC 1967, 50, 652-654.
36. Turczan, J. W. J. Pharm. Sci. 1968, 57, 142-144.
37. Turczan, J. W.; Goldwitz, B. A.; Nelson, J. J. Talanta 1972, 19, 1549-1554.
38. Turczan, J. W.; Goldwitz, B. A. J. Pharm. Sci. 1972, 61, 1309-1310.
39. Turczan, J. W.; Goldwitz, B. A. J. Pharm. Sci. 1972, 61, 613-615.
40. Turczan, J.; Medwick, T. J. Pharm. Sci. 1972, 61, 434-443.
41. Turczan, J. W.; Goldwitz, B. A. J. Pharm. Sci. 1973, 62, 1705-1707.
42. Turczan, J. W.; Goldwitz, B. A. J. Assoc. Off. Anal. Chem. 1973, 56, 669-673.
43. Turczan, J. W. J. Assoc. Off. Anal. Chem. 1974, 57, 893-896.
44. Turczan, J. W.; Medwick, T. J. Pharm. Sci. 1974, 63, 425-427.
45. Turczan, J. W. Anal. Chim. Acta 1974, 68, 395-400.
46. Turczan, J. W.; Medwick, T. J. Pharm. Sci. 1976, 65, 235-238.
47. Turczan, J. W.; Medwick, T. Anal. Lett. 1977, 10, 581-590.
48. Turczan, J.; Lau-Cam, C. Spectrosc. Lett. 1984, 17, 353-359.
49. Turczan, J.; Lau-Cam, C. Pharmazie 1986, 41, 775-776.
50. Turczan, J. W.; Lau-Cam, C. A. Spectrosc. Lett. 1987, 20, 45-52.
51. Turczan, J. W.; Lau-Cam, C. A. Drug Dev. Ind. Pharm. 1989, 15, 107-115.
52. Pieters, L. A.; Vlietinck, A. J. J. Pharm. Biomed. Anal. 1989, 7, 1405-1471.
53. Rackham, D. M. Talanta 1976, 23, 269-274.
54. Malet-Martino, M. C.; Martino, R. Xenobiotica 1989, 19, 583-607.
55. Corcoran, O.; Lindon, J. C.; Hall, R.; Ismail, I. M.; Nicholson, J. K. Analyst 2001, 126, 2103-2106.
56. Ratcliffe, R. G.; Roscher, A. Biodegradation 1998, 9, 411-422.
57. O'Hagan, D.; Harper, D. B. J. Fluorine Chem. 1999, 100, 127-133.
58. O'Hagan, D.; Harper, D. B. Natural Products Containing Fluorine and Recent Progress in Elucidating the Pathway of Fluorometabolite Biosynthesis in Streptomyces cattleya; Symposium Series 746; Ramachandran, P. V., Ed.; American Chemical Society: Washington, DC, 1999; pp 210-224.
59. Experimental NMR Conference (ENC). Annual Meetings; available at http://www.enc-conference.org/.
60. SMASH NMR Conference; available at http://www.smashnmr.org/.
61. Patt, S. L. A Qualitative Advance in Quantitative Analysis on the XL-200; Varian Inc.: 1981; 1-5 pp.
62. Cookson, D. J.; Smith, B. E. Anal. Chem. 1982, 54, 2591-2563.
63. Ward, G. A. Am. Labor. 1970, 2, 55-61.
64. Ernst, R. R.; Anderson, W. A. Rev. Sci. Instrum. 1966, 37, 93-102.
65. Simeral, L. S. Appl. Spectrosc. 1995, 49, 400-402.
66. Simeral, L. S. Today's Chem. Work 1993, 11, 52-57.
67. Shaka, A. J.; Keeler, J.; Freeman, R. J. Magn. Reson. 1983, 53, 313-340.
68. Shaka, A. J.; Keeler, J.; Frenkiel, T.; Freeman, R. J. Magn. Reson. 1983, 52, 335-338.
69. Shaka, A. J.; Barker, P. B.; Freeman, R. J. Magn. Reson. 1985, 64, 547-552.
70. Traficante, D. D.; Raiabzadeh, M. Concepts NMR 2000, 12, 83-101.
71. Traficante, D. D.; Ziessow, D. J. Magn. Reson. 1986, 66, 182-186.
72. Traficante, D. D.; Nemeth, G. A. J. Magn. Reson. 1987, 71, 237-245.
73. Nelson, S. J.; Brown, T. R. J. Magn. Reson. 1989, 84, 95-109.
74. Bain, A. D.; Fahie, B. J.; Kozluk, T.; Leigh, W. J. Can. J. Chem. 1991, 69, 1189-1192.
75. Martin, Y. L. J. Magn. Reson. Ser. A 1994, 111, 1-10.
76. Jeannerat, D. Computer Processing Techniques in High-Resolution NMR; Academic Press (Elsevier): New York, 2002; Vol. 46, pp 151-212.
77. Krack, G.; Kotterba, W.; Schnell, H. SMASH 2003 NMR Conference: Verona, Italy, 2003, September 14-17 (#53).
78. Talebpour, Z.; Haghgoo, S.; Shamsipur, M. Anal. Chim. Acta 2004, 506, 97-104.
79. Özden, T.; Senyuva, H.; Aksahin, I. J. Pharm. Biomed. Anal. 1999, 21, 467-472.
80. Deubner, R.; Holzgrabe, U. Magn. Reson. Chem. 2002, 40, 762-766.
81. Bilia, A. R.; Bergonzi, M. C.; Lazari, D.; Vincieri, F. F. J. Agric. Food Chem. 2002, 50, 5016-5025.
82. Meyers, J. A.; Dal Cason, T. A.; Lankin, D. 32nd Experimental Nuclear Magnetic Resonance Spectroscopy Conference (ENC): St. Louis, MO, 1991, April 7-11.
83. Naqvi, A. A.; Mandai, S.; Verma, R. K. Phytochem. Anal. 1998, 9, 168-170.
84. Choi, Y. H.; Choi, H. K.; Hazekamp, A.; Bermejo, P.; Schilder, Y.; Erkelens, C.; Verpoorte, R. Chem. Pharm. Bull. 2003, 51, 158-161.
85. Li, C. Y.; Lin, C. H.; Wu, C. C.; Lee, K. H.; Wu, T. S. J. Agric. Food Chem. 2004, 52, 3721-3725.
86. Berregi, I.; Santos, J. I.; del Campo, G.; Miranda, J. I. Talanta 2003, 61, 139-145.
87. Berregi, I.; Santos, J. I.; Del Campo, G.; Miranda, J. I.; Aizpurua, J. M. Anal. Chim. Acta 2003, 486, 269-274.
88. Hazekamp, A.; Choi, Y. H.; Verpoorte, R. Chem. Pharm. Bull. 2004, 52, 718-721.
89. 1H NMR spectroscopy; ChemWeb.com Preprint Server 2001, available at http://www.chemweb.com/preprint?url=/analchem/ 0103002/.
90. Wells, R. J.; Hook, J. M.: Al-Deen, T. S.; Hibbert, D. B. J. Agric. Food Chem. 2002, 50, 3366-3374.
91. Al-Deen, S. T.; Hibbert, D. B.; Hook, J. M.; Wells, R. J. Anal Chim. Acta 2002, 474, 125-135.
92. De Graaf, R. A.; Behar, K. L. Anal. Chem. 2003, 75, 2100-2104.
93. Azaroual, N.; Imbenotte, M.; Cartigny, B.; Leclerc, F.; Vallee, L.; Lhermitte, M.; Vermeersch, G. Magn. Reson. Mater. Phys. Biol. Med. 2000, 10, 177-182.
94. Wittig, J.; Wittemer, S.; Veit, M. J. Chromatogr. B 2001, 761, 125-132.
95. Wittig, J.; Leipolz, I.; Graefe, E. U.; Jaki, B.; Treutter, D.; Veit, M. Arzneirn.-Forsch. 2002, 52, 89-96.
96. Jaki, B.; Sticher, O.; Veit, M.; Fröhlich, R.; Pauli, G. F. J. Nat. Prod. 2002, 65, 517-522.
97. Catchpole, O. J.; Grey, J. B.; Perry, N. B.; Burgess, E. J.; Redmond, W. A.; Porter, N. G. J. Agric. Food Chem. 2003, 51, 4853-4860.
98. Gerritz, S. W.; Sefler, A. M. J. Comb. Chem. 2000, 2, 39-41.
99. Saito, T.; Nakaie, S.; Kinoshita, M.; Ihara, T.; Kinugasa, S.; Nomura, A.; Maeda, T. Metrologia 2004, 41, 213-218.
100. Saito, T.; Iwasawa, R.; Ihara, T.; Kinugasa, S.; Nomura, A.; Maeda, T. Chromatography 2003, 24.
101. Al-Deen, T. S.; Hibbert, D. B.; Hook, J. M.; Wells, R. J. Accred. Qual. Assur. 2004, 9, 55-63.
102. Quinn, T. Metrologia 1997, 34, 61-65.
103. Jahncke, H.; Malz, F. Final Report CCQM-4; Bundesanstalt für Materialforschung- und prüning: Berlin (Germany), 2000.
104. Jancke, H.; Malz, F. GIT Lab. Fachz. 2004, 48, 492-493.
105. Lindon, J. C.; Nicholson, J. K.; Holmes, E.; Everett, J. R. Concepts Magn. Reson. 2000, 12, 289-320.
106. Lindon, J. C.; Nicholson, J. K.; Wilson, I. D. Prog. Nucl. Magn. Reson. Spectrosc. 1996, 29, 1-49.
107. Dumas, M.-E.; Debrauwer, L.; Beyet, L.; Lesage, D.; Andre, F.; Paris, A.; Tabet, J.-C. Anal. Chem. 2002, 74, 5393-5404.
108. Schoen, J.; Modha, A.; Maslow, K.; Novak, M.; Blackburn, B. J. Int. J. Parasitol. 1996, 26, 713-722.
109. Le Gall, G.; Colquhoun, I. J.; Davis, A. L.; Collins, G. J.; Verhoeyen, M. E. J. Agric. Food Chem. 2003, 51, 2447-2456.
110. Jukarainen, N.; Soininen, P.; Korolainen, M.; Laasko, M.; Niemitz, M.; Tuppurainen, K.; Vepsalainen, J.; Pirttila, T.; Laatikainen, R. SMASH 2003 NMR Conference: Verona (Italy), 2003, September 14-17 (#56).
111. Ogrinc, N.; Kosir, I. J.; Spangenberg, J. E.; Kidric, J. Anal. Bioanal. Chem. 2003, 376, 424-430.
112. Duarte, I.; Barros, A.; Belton, P. S.; Righelato, R.; Spraul, M.; Humpfer, E.; Gil, A. M. J. Agric. Food Chem. 2002, 50, 2475-2481.
113. Duarte, I. F.; Barros, A.; Almeida, C.; Spraul, M.; Gil, A. M. J. Agric. Food Chem. 2004, 52, 1031-1038.
114. Duarte, I. F.; Godejohann, M.; Braumann, U.; Spraul, M.; Gil, A. M. J. Agric. Food Chem. 2003, 51, 4847-4852.
115. Nilsson, M.; Duarte, I. F.; Almeida, C.; Delgadillo, I.; Goodfellow, B. J.; Gil, A. M.; Morris, G. A. J. Agric. Food Chem. 2004, 52, 3736-3743.
116. Forveille, L.; Vercauteren, J.; Rutledge, D. N. Food Chem. 1996, 57, 441-450.
117. Mannina, L.; Patumi, M.; Proietti, N.; Bassi, D.; Segre, A. L. J. Agric. Food Chem. 2001, 49, 2687-2696.
118. Mannina, L.; Dugo, G.; Salvo, F.; Cicero, L.; Ansanelli, G.; Calcagni, C.; Segre, A. J. Agric. Food Chem. 2003, 51, 120-127.
119. Kosir, I. J.; Kidric, J. Anal. Chim. Acta 2002, 458, 77-84.
120. Kosir, I. J.; Lapornik, B.; Andrensek, S.; Wondra, A. G.; Vrhovsek, U.; Kidric, J. Anal. Chim. Acta 2004, 513, 277-282.
121. Kosir, I. J.; Kidric, J. J. Agric. Food Chem. 2001, 49, 50-56.
122. Consonni, R.; Gatti, A. J. Agric. Food Chem. 2004, 52, 3446-3450.
123. Martin, G. J.; Martin, M. L.; Mabon, F.; Michon, M. J. J. Agric. Food Chem. 1983, 31, 311-315.
124. Martin, G. J.; Zhang, B. L.; Naulet, N.; Martin, M. L. J. Am. Chem. Soc. 1986, 108, 5116-5122.
125. Ogrinc, N.; Kosir, I. J.; Kocjancic, M.; Kidric, J. J. Agric. Food Chem. 2001, 49, 1432-1440.
126. Billault, I.; Mantle, P. G.; Robins, R. J. J. Am. Chem. Soc. 2004, 126, 3250-3256.
127. Guiet, S.; Robins, R. J.; Lees, M.; Billault, I. Phytochemistry 2003, 64, 227-233.
128. Choi, Y. H.; Kim, H. K.; Hazekamp, A.; Erkelens, C.; Lefeber, A. W.; Verpoorte, R. J. Nat. Prod. 2004, 67, 953-957.
129. deGraaf, R. A.; Lammers, G.; Janssen, L.; Beenackers, A. Starch-Starke 1995, 47, 469-475.
130. Hile, A. G.; Shan, Z.; Block, E. J. Agric. Food Chem. 2004, 52, 2192-2196.
131. Erickson, N. A.; Kolodny, N. H.; Allen, M. M. Biochim. Biophys. Acta 2001, 1526, 5-9.
132. Burton, I. W.; Quilliam, M. A.; Walter, J. A. 42nd Experimental Nuclear Magnetic Resonance Spectroscopy Conference (ENC): Orlando, FL, 2001, March 11-16, 2001.
133. van de Velde, F.; Knutsen, S. H.; Usov, A. I.; Rollema, H. S.; Cerezo, A. S. Trends Food Sci. Technol. 2002, 13, 73-92.
134. Tojo, E.; Prado, J. Carbohydr. Polym. 2003, 53, 325-329.
135. Bauer, S. H. J.; Mansson, M.; Hood, D. W.; Richards, J. C.; Moxon, E. R.; Schweda, E. K. H. Carbohydr. Res. 2001, 335, 251-260.
136. van Beek, T. A.; van Veldhuizen, A.; Lelyveld, G. P.; Piron, I. Phytochem. Anal. 1993, 4, 261-268.
137. Lichtblau, D.; Berger, J. M.; Nakanishi, K. J. Nat. Prod. 2002, 65, 1501-1504.
138. Bilia, A. R.; Bergonzi, M. C.; Mazzi, G.; Vincieri, F. F. J. Agric. Food Chem. 2001, 49, 2115-2124.
139. Bilia, A. R.; Bergonzi, M. C.; Mazzi, G.; Vincieri, F. F. J. Pharm. Biomed. Anal. 2002, 30, 321-330.
140. Bilia, A. R.; Bergonzi, M. C.; Morgenni, F.; Mazzi, G.; Vincieri, F. F. Int. J. Pharmazeut. 2001, 213, 199-208.
141. Knothe, G.; Kenar, J. A. Eur. J. Lipid Sci. Technol. 2004, 106, 88-96.
142. Belloque, J.; Ramos, M. Trends Food Sci. Technol. 2000, 10, 313-320.
143. Frederich, M.; Choi, Y. H.; Verpoorte, R. Planta Med. 2003, 89, 1169-1171.
144. Krebs, H. C.; Carl, T.; Habermehl, G. G. Phytochemistry 1996, 43, 1227-1229.
145. Aboutabl, E. A.; Ei-Azzouny, A. A.; Afifi, M. S. Phytochem. Anal. 2002, 13, 301-304.
146. Gil, A. M.; Duarte, I. F.; Godejohann, M.; Braumann, U.; Maraschin, M.; Spraul, M. Anal. Chim. Acta 2003, 488, 35-51.
147. Meusinger, R. Fuel 1996, 75, 1235-1243.
148. Meusinger, R. Anal. Chim. Acta 1999, 391, 277-288.
149. Albert, K. J. Chromatogr., A 1995, 703, 123-147.
150. Vogler, B.; Halber, I.; Roos, G.; Walter, C. U.; Killer, W.; Sandor, P.; Kraus, W. J. Nat. Prod. 1998, 61, 175-178.
151. Weifender, J. L.; Ndjoko, K.; Hostettmann, K. Phytochem. Anal. 2001, 12, 2-22.
152. Keifer, P. A. Prog. Drug Res. 2000, 55, 137-211.
153. Albert, K.; Dachtier, M.; Glaser, T.; Handel, H.; Lacker, T.; Schlotterbeck, G.; Strohschein, S.; Tseng, L. H.; Braumann, U. J. High Resolut. Chromatogr. 1999, 22, 135-143.
154. Subramanian, R.; Sweedler, J. V.; Webb, A. G. J. Am. Chem. Soc. 1999, 121, 2333-2334.
155. Olson, D. L.; Lacey, M. E.; Sweedler, J. V. Anal. Chem. 1998, 70, 257A-264A.
156. Olson, D. L.; Lacey, M. E.; Sweedler, J. V. Anal. Chem. 1998, 70, 645-650.
157. Lacey, M. E.; Subramanian, R.; Olson, D. L.; Webb, A. G.; Sweedler, J. V. Chem. Rev. 1999, 99, 3133-3152.
158. Martin, G. E.; Hadden, C. E.; Russell, D. J.; Kaluzny, B. D.; Guido, J. E.; Duholke, W. K.; Stiemsma, B. A.; Thamann, T. J.; Crouch, R. C.; Blinov, K.; Elyashberg, M.; Martirosian, E. R.; Molodtsov, S. G.; Williams, A. J.; Schiff, P. L., Jr. J. Heterocycl. Chem. 2002, 39, 1241-1250.
159. Godejohann, M.; Preiss, A.; Levsen, K.; Wollin, K. M.; Mugge, C. Acta Hydrochim. Hydrobiol. 1998, 26, 330-337.
160. Fischer, H.; Tseng, L. H.; Raitza, M.; Aibert, K. Magn. Reson. Chem. 2000, 38, 336-342.
161. Maiwald, M.; Fischer, H. H.; Kim, Y.-K.; Albert, K.; Hasse, H. J. Magn. Reson. 2004, 166, 135-146.
162. Chiu, P. L.; Patterson, G. W.; Fenner, G. P. Phytochemistry 1985, 24, 263-266.
163. Thunhorst, M.; Holzgrabe, U. Magn. Reson. Chem. 1998, 36, 211-216.
164. Hanna, G. M.; Lau-Cam, C. A.; Plank, W. M. Pharmazie 1989, 44 321-325.
165. Hanna, G. M.; Lau-Cam, C. A. J. Pharm. Biomed. Anal. 1989, 7, 919-928.
166. Hanna, G. M.; Lau-Cam, C. A. J. Assoc. Off. Anal. Chem. 1989, 72, 552-555.
167. Hanna, G. M.; Lau-Cam, C. A. Pharm. Res. 1990, 7, 726-729.
168. Hanna, G. M.; Lau-Cam, C. A. J. Pharm. Biomed. Anal. 1993, 11, 855-859.
169. Hanna, G. M.; Lau-Cam, C. A. J. Pharm. Biomed. Anal. 1995, 13, 1313-1319.
170. Hanna, G. M. J. Pharm. Biomed. Anal. 1997, 15, 1805-1811.
171. Hanna, G. M. Enantiomer 2000, 5, 303-312.
172. Hanna, G. M.; Evans, F. E. J. Pharm. Biomed. Anal. 2000, 24, 189-196.
173. Hanna, G. M. Pharmazie 2001, 56, 314-317.
174. Whitesides, G. M.; Lewis, D. W. J. Am. Chem. Soc. 1970, 92, 6979.
175. Wenzel, T. J. NMR Shift Reagents; CRC Press: Boca Raton, FL, 1987.
176. Jaki, B.; Franzblau, S. G.; Pauli, G. F. Phytochem. Anal. 2004, 15, 213-219.
177. Jaki, B.; Franzblau, S. G.; Chadwick, L.; Wang, Y.; Zhang, F.; Pauli, G. F. Unpublished data.
178. Maniara, G.; Rajamoorthi, K.; Rajan, S.; Stockton, G. W. Anal. Chem. 1998, 70, 4921-4928.
179. Soininen, P.; Haarala, J.; Niemitz, M.; Laatikainen, R. SMASH 2003 NMR Conference: Verona (Italy), 2003, September 14-17 (#19).
180. Jaki, B.; Glodny, B.; Pauli, G. F. 2nd ASP/CRN Interim Meeting on Botanical Supplements: Asilomar, 2001, November 8-11, 2001 (O-24).
181. Pauli, G. F. Planta Med. 2000, 66, 299-302.
182. Jaki, B.; Franzblau, S.; Pauli, G. F. SMASH 2003: Verona (Italy), 2003, September 14-17 (#11).
183. Hanna, G. M. Pharmazie 2004, 59, 170-174.
184. Hanna, G. M.; Lau-Cam, C. A. J. Assoc. Off. Anal. Chem. 1988, 71, 1118-1121.
185. Hanna, G. M. J. Assoc. Off. Anal. Chem. 1995, 78, 946-954.
186. Guerrini, M.; Bisio, A.; Torri, G. Semin. Thromb. Hemostasis 2001, 27, 473-482.
187. Hanna, G. M.; Lau-Cam, C. A. J. Assoc. Off. Anal. Chem. 1987, 70, 557-559.
188. Hanna, G. M.; Lau-Cam, C. A. J. Assoc. Off. Anal. Chem. 1993, 76, 526-530.
189. Hanna, G. M. J. Assoc. Off. Anal. Chem. 1984, 67, 222-224.
190. Hanna, G. M.; Lau-Cam, C. A. Pharmazie 2001, 56, 700-703.
191. Hanna, G. M.; Lau-Cam, C. A. Pharmazie 1984, 39, 816-818.
192. Hanna, G. M.; Lau-Cam, C. A. Pharmazie 2001, 56, 152-155.
193. Oezden, T.; Senyuva, H.; Aksahin, I. J. Pharm. Biomed. Anal. 1999, 21, 467-472.
194. Gobas, J. C.; Sardina, F. J. Concepts Magn. Reson. 2003, 19A, 80-96.
195. Additional information on this subject may be found at http://qnmr.org.