Strategy of preparative separation of organic compounds by thin-layer chromatographic methods

Journal of Liquid Chromatography and Related Technologies

Volumn 25, Issue 13-15, 2002, Pages 2351-2386

  Waksmundzka Hajnos, M ^a   Wawrzynowicz, T ^a  

^a MEDICAL UNIVERSITY OF LUBLIN   (Poland)

Author keywords

Adsorbent characteristics; Basic planar techniques; Modes of development; Modes of sampling; Preparative layer chromatography; Solvent characteristics

Indexed keywords

INFORMATION ANALYSIS; THIN LAYER CHROMATOGRAPHY;

CHROMATOGRAPHIC METHODS; ISOLATION;

ORGANIC COMPOUNDS;

ALKALOID; ANTHOCYANIN; ANTHRAQUINONE DERIVATIVE; BENZYLISOQUINOLINE DERIVATIVE; CHOLESTEROL DERIVATIVE; CYCLOPEPTIDE; DITERPENOID; FATTY ACID; FLAVONE DERIVATIVE; FLAVONOID; GANGLIOSIDE; GUAIANOLIDE DERIVATIVE; LACTONE; LIMONOID; NAPHTHOQUINONE; OIL; ORGANIC COMPOUND; PHTHALIDE DERIVATIVE; PROTOBERBERINE DERIVATIVE; QUINOLINE DERIVATIVE; SAPONIN DERIVATIVE; SPHINGOLIPID; STEROL DERIVATIVE; TAXOID; TRIACYLGLYCEROL; TRITERPENE DERIVATIVE; TROPANE DERIVATIVE; UNINDEXED DRUG; XANTHINE; XANTHONE DERIVATIVE;

ADSORPTION; CHEMICAL ANALYSIS; PLANAR CHROMATOGRAPHY; QUANTITATIVE ASSAY; REVIEW; SAMPLING; SOLUBILITY; THIN LAYER CHROMATOGRAPHY;

EID: 0036381915     PISSN: 10826076     EISSN: None     Source Type: Journal    
DOI: 10.1081/JLC-120014009     Document Type: Review

References (155)

1. Nyiredy, Sz. Preparative Planar Chromatography. In Handbook of Thin Layer Chromatography; Fried, B., Sherma, J., Eds.; Marcel Dekker: New York, 1996; 307-340.
2. Nyiredy, Sz. Possibilities of Preparative Planar Chromatography. In Planar Chromatography. A Retrospecive View for the Third Millenium; Nyiredy, Sz., Ed.; Springer Scientific Publisher: New York, 2001; 386-409.
3. Hostettmann, K.; Marston, A.; Hostettmann, M. Preparative Chromatography Techniques. Application in Natural Product Isolation, 2nd Ed.; Springer Verlag: Heidelberg, 1997; 12-33.
4. Grinberg, N. Modern Thin Layer Chromatography; Grinberg, N., Ed.; Marcel Dekker: New York, 1990.
5. Sherma, J.; Fried, B. Preparative Thin Layer Chromatography. In Preparative Liquid Chromatography; Bidlingmeyer, B.A., Ed.; Elsevier: Amsterdam, Oxford, New York, Tokyo, 1987.
6. Sherma, J. Anal. Chem. 1996, 68, 1R-19R.
7. Sherma, J. Anal. Chem. 1998, 70, 7R-26R.
8. Schlitt, A.; Geiss, F. J. Chromatogr. 1972, 67, 261-276.
9. Waksmundzka-Hajnos, M.; Wawrzynowicz, T. J. Planar Chromatogr. 1990, 3, 439-441.
10. Wawrzynowicz, T.; Waksmundzka-Hajnos, M. J. Liq. Chromatogr. 1990, 13, 3925-3940.
11. Wawrzynowicz, T.; Soczewinski, E. J. Chromatogr. 1979, 169, 191-203.
12. Soczewinski, E. J. Chromatogr. 1977, 138, 442-445.
13. Soczewinski, E. Equilibrium Sandwich Chamber for Continuous Development with a Glass Distributor. In Planar Chromatography; Kaiser, R.E., Ed., Huethig: Heidelberg, 1986; Vol. 1, 79-117.
14. Wawrzynowicz, T.; Soczewinski, E.; Czapinska, K. Chromatographia 1981, 20, 729-732.
15. Soczewinski, E.; Wawrzynowicz, T. J. Chromatogr. 1981, 218, 729-732.
16. Soczewinski, E.; Czapinska, K. J. Chromatogr. 1979, 168, 230-233.
17. Gołkiewicz, W.; Wolski, T. HRC&CC 1981, 4, 115-120.
18. Waksmundzka-Hajnos, M.; Wawrzynowicz, T. J. Planar Chromatogr. 1992, 5, 169-174.
19. Dzido, T.H.; Soczewiński, E. J. Chromatogr. 1990, 516, 461-466.
20. Brenner, M.; Niederwieser, A. Expeoientia (Basel) 1961, 17, 237-238.
21. Dzido, T.H. J. Planar Chromatogr. 1990, 3, 199-200.
22. Dzido, T.H. J. Planar Chromatogr. 1993, 6, 78-81.
23. Waksmundzka-Hajnos, M.; Wawrzynowicz, T. J. Planar Chromatogr. 1994, 7, 58-62.
24. Dzido, T.H.; Matysik, G.; Soczewinski, E. J. Planar Chromatogr. 1991, 4, 161-164.
25. Matysik, G.; Soczewinski, E.; Polak, B. Chromatographia 1994, 39, 491-504.
26. Tyihak, E.; Mincsovics, E. J. Planar Chromatogr. 1988, 1, 6-19.
27. Tyihak, E.; Mincsovics, E.; Kalasz, H. J. Chromatogr. 1979, 174, 75-81.
28. Nyiredy, Sz.; Erdelmeier, C.A.; Sticher, O. Instrumental Preparative Planar Chromatography. In Planar Chromatography; Kaiser, R.E., Ed.; Huethig: Heidelberg, 1986; Vol. 1, 119-164.
29. Zogg, G.C.; Nyiredy, Sz.; Sticher, O. Chromatographia 1989, 27, 591-595.
30. Zogg, G.C.; Nyiredy, Sz.; Sticher, O. J. Planar Chromatogr. 1988, 1, 261-264.
31. Botz, L.; Nyiredy, Sz.; Sticher, O. J. Planar Chromatogr. 1990, 3, 401-406.
32. Mincsovics, E.; Tyihak, E.; Siouffi, A.M. J. Planar Chromatogr. 1988, 1, 141-145.
33. Botz, L.; Nyiredy, Sz.; Sticher, O. J. Planar Chromatogr. 1990, 3, 352-354.
34. Botz, L.; Nyiredy, Sz.; Sticher, O. J. Planar Chromatogr. 1991, 4, 115-122.
35. DeStefano, J.J.; Kirkland, J.J. Anal. Chem. 1975, 47, 1103A-1108A.
36. Knox, J.H.; Pyper, H.M. J. Chromatogr. 1986, 363, 1-30.
37. Soczewinski, E.; Wawrzynowicz., T. Chromatographia 1978, 11, 466-468.
38. Soczewinski, E.; Kuczmierczyk, J. J. Chromatogr. 1978, 150, 53-61.
39. Botz, L.; Nyiredy, Sz.; Sticher, O. J. Planar Chromatogr. 1990, 3, 10-14.
40. Soczewinski, E.; Wawrzynowicz, T. Preparative TLC. In Encyclopedia of Chromatography; Cazes, J., Ed.; Marcel Dekker Inc.: New York, Basel, 2000; 660-662.
41. Czapinska, K.; Markowski, W.; Wawrzynowicz, T. Chem. Anal. (Warsaw) 1988, 33, 271-283.
42. Golkiewicz, W.; Werkhoven-Goewie, G.E.; Brinkman, U.A.Th.; Frei, R.W.; Colin, H.; Guiochon, G. J. Chromatogr. Sci. 1983, 21, 27-33.
43. Nyiredy, Sz.; Dallenbach-Tölke, K.; Sticher, O. J. Planar Chromatogr. 1988, 1, 336-348.
44. Waksmundzka-Hajnos, M.; Petruczynik, A.; Hawryl, A. J. Chromatogr. A 2001, 919, 39-50.
45. Snyder, L.R.; Kirkland, J.J. Introduction to Modern Liquid Chromatography; Wiley: New York, 1974; Vol. 72, 462 pp.
46. Matysik, G.; Soczewinski, E. J. Chromatogr. 1986, 369, 19-25.
47. Soczewinski, E.; Czapińska, K.; Wawrzynowicz, T. Sepn. Sci. Technol. 1987, 22 (8-10), 2101-2110.
48. Perry, J.P.; Jupille, T.H.; Glunz, J. Anal. Chem. 1975, 47, 65A-74A.
49. Poole, C.F.; Poole, S.K.; Fernando, W.P.N.; Dean, T.A.; Ahmed, H.D.; Berndt, J.A. J. Planar Chromatogr. 1989, 2, 336-345.
50. Perry, J.A.; Jupille, T.H.; Curtice, A. Sepn. Sci. 1975, 10, 571-591.
51. Wawrzynowicz, T.; Czapinska, K.; Markowski, W. J. Planar Chromatogr. 1998, 11, 388-393.
52. Quader, A.; But, P.P.; Gray, A.I.; Hartley, T.G.; Hu, H.J.; Waterman, P.G. Biochem. Syst. Ecol. 1990, 18, 251-252.
53. Golkiewicz, W.; Gadzikowska, M. Chromatographia 1999, 50, 52-56.
54. Zwickenpflug, W.; Mieger, M.; Richter, E. J. Agric. Food Chem. 1998, 46, 2703-2706.
55. Ma, Q.X.; Jiang, S.H.; Zhu, D.Y. Biochem. Syst. Ecol. 1998, 26, 2723-2728.
56. Chia, J.C.; Chang, F.R.; Li, C.M.; Wu, Y.C. Phytochemistry 1998, 48, 367-369.
57. Toro, M.J.V.; Muller, A.H.; Arruda, M.S.P.; Arruda, A.C. Phytochemistry 1997, 45, 851-853.
58. Kam, T.S.; Yoganathan, K. Phytochemistry 1996, 42, 539-541.
59. Wei, X.; Wei, B.; Zhang, J. J. Chinese Herb. Med. 1995, 26, 344-346.
60. Kanyinda, B.; Vanhaelen-Fastre, R.; Vanhaelen, M. J. Nat. Prod. 1995, 58, 1587-1589.
61. Funayama, S.; Murata, K.; Nozoe, S. Phytochemistry 1994, 36, 525-528.
62. Anzi, A.A.; Gray, A.I.; Hartley, T.G.; Waigh, R.D.; Watermann, P.G. Phytochemistry 1994, 36, 535-536.
63. Golkiewicz, W.; Gadzikowska, M.; Kuczynski, J.; Jusiak, L. J. Planar. Chromatogr. 1993, 6, 382-385.
64. Ghedira, K.; Chemli, R.; Richard, B.; Nuzillard, J.M.; Zeches, E.; Le Men-Olivier, L. Phytochemistry 1993, 32, 1591-1594.
65. Houghton, P.J.; Osibogun, I.M. Phytochem. Anal. 1990, 1, 22-25.
66. Houghton, P.J.; Latiff, A.; Said, I.M. Phytochemistry 1991, 30, 347-350.
67. El-Imam, Y.M.A.; Evans, W.C.; Grout, R.J. Phytochemistry 1988, 27, 2181-2184.
68. Joshi, B.S.; Desai, H.K.; Pelletier, S.W.; Snyder, J.K.; Zhang, K.; Chen, S.Y. Phytochemistry 1990, 29, 357-358.
69. Kaonadji, M. J. Nat. Prod. 1988, 51, 376-378.
70. Tarr, F. Magyar Kemiai Folyorat 1993, 99, 89-92.
71. Crawford, L.; McDonald, G.M.; Friedman, M. J. Agric. Food Chem. 1990, 38, 2169-2175.
72. Yankep, E.; Mbafor, M.T.; Fomum, Z.T.; Steinbeck, C.; Messanga, B.B. Phytochemistry 2001, 56, 363-368.
73. Huck, C.W.; Huber, G.G.; Bonn, G.K. J. Chromatogr. A 2000, 870, 453-462.
74. Lin, L.; He, X.; Lindenmaier, M.; Nolan, G.; Yang, J.; Cleary, M.; Qiu, S. J. Chromatogr. A 2000, 876, 87-95.
75. Guz, N.R.; Lorenz, P.; Stermitz, F.R. Tetrahedron Lett. 2001, 42, 6491-6494.
76. Melzer, R.; Fricke, U.; Hölzl, J. Arzneim.-Forsch. Drug Res. 1991, 41, 481-483.
77. LeMeu-Olivier, L.; Renault, J.H.; Thepenier, P.; Jacquier, M.J.; Zaches-Hanrot, M.; Foucault, M.P. J. Liq. Chromatogr. 1995, 18, 1663-1670.
78. Hano, Y.; Matsumoto, Y.; Shinohara, K.; Sun, J.Y.; Nomura, T. Planta Med. 1991, 57, 172-175.
79. Nagy, G.; Yang, M.H.; Gunther, G.; Mathi, I.; Blunden, G.; Crabb, T.A. Biochem. Syst. Ecol. 1998, 26, 797-799.
80. Jakupovic, J.; Jeske, F.; Morgenstern, T.; Marco, J.A.; Berendsohn, W. Phytochemistry 1998, 47, 1583-1600.
81. El-Babili, F.; Moulis, C.; Bon, M.; Respaud, M.J.; Fouraste, I. Phytochemistry 1998, 48, 165-169.
82. Ryu, S.Y.; Lee, C.O.; Choi, S.U. Planta Med. 1997, 63, 339-342.
83. Olafsson, K.; Jaroszewski, J.W.; Smitt, U.W.; Nyman, U. Planta Med. 1997, 63, 352-355.
84. Kawabata, J.; Fukushi, E.; Mizutani, J. Phytochemistry 1998, 47, 231-235.
85. Souto-Baciller, F.A.; Mielendez, P.A.; Romero-Ramsey, L. Phytochemistry 1997, 44, 1077-1086.
86. Sattar, E.A.; Mossa, J.S.; Muhammad, I.; El-Faraly, F.S. Phytochemistry 1995, 40, 1737-1741.
87. Sarker, S.D.; Armstrong, J.A.; Waterman, P.G. Phytochemistry 1995, 40, 1159-1162.
88. Reher, G.; Budesinsky, M. Phytochemistry 1992, 31, 3909-3914.
89. Ayer, W.A.; Trifonov, L.S. J. Nat. Prod. 1992, 55, 1454-1461.
90. Alonso-Amilot, M.E.; Perez-Mena, M.; Calcagno, M.P.; Jaimes-Ėspinoza, R. Phytochem. Anal. 1992, 3, 160-164.
91. Tu, Y.Q. Phytochemistry 1992, 31, 2155-2157.
92. Sharma, O.P; Sharma, S.; Dawra, R.K. J. Chromatogr. A 1997, 786, 181-184.
93. Cangiano, T.; Della-Greca, M.; Fiorentino, A.; Isadori, M.; Monaco, P. Phytochemistry 2001, 56, 469-473.
94. Gu, J.G.; Park, E.J.; Luygeni, L.; Hawthorne, M.E.; Mehta, R.G. Phytochemistry 2001, 58, 121-127.
95. Nawaz, R.H.; Malik, A.; Ali, M.S. Phytochemistry 2001, 56, 99-102.
96. Hohmann, J.; Evanics, F.; Dombi, G.; Molnar, P.; Szabo, P. Tetrahedron 2001, 57, 211-215.
97. Trute, A.; Gross, J.; Mutschler, E.; Nahrstedt, A. Planta Med. 1997, 63, 125-129.
98. Sun, W.; Sha, Z.; Yang, J. Chin. J. Herb. Med. 1993, 24, 619-622.
99. Seifert, K.; Preiss, A.; Johne, S.; Schmidt, J.; Lien, N.T.; Lavaud, C.; Massiot, G. Phytochemistry 1991, 30, 3395-3400.
100. Zhang, X. Chin. J. Chromatogr. 1996, 4, 183-185.
101. Caboni, M.F.; Costa, J.; Rodriguez-Estrade, M.F.; Lercker, G. Chromatographia 1997, 46, 151-155.
102. Van Boven, G.; Daenkens, P.; Maes, K.; Coklaere, M. J. Agric. Food Chem. 1997, 45, 1180-1184.
103. Heltzel, C.E.; Gunatilaka, A.A.L.; Kingston, D.G.I.; Hoffmann, G.A.; Johnson, R.K. J. Nat. Prod. 1994, 57, 620-628.
104. Guantilaka, A.A.L.; Samaranayake, G.; Kingston, D.G.I.; Hoffmann, G.A.; Johnson, R.K. J. Nat. Prod. 1992, 55, 1648-1654.
105. Gopalakrishinan, M.; Narayanan, C.S.; Granz, M. J. Agric. Food Chem. 1990, 38, 2133-2136.
106. Garcia Regueiro, J.A.; Maraschiello, C. J. Chromatogr. A 1997, 764, 279-293.
107. Glowniak, K.; Mroczek, T. J. Liq. Chromatogr. & Rel. Technol. 1999, 22, 2483-2502.
108. Wawrzynowicz, T.; Glowniak, K.; Hajnos, M.L.; Mroczek, T. J. Planar Chromatogr. 1999, 12, 328-335.
109. Hajnos, M.L.; Glowniak, K.; Waksmundzka-Hajnos, M.; Kogut, P. J. Planar Chromatogr. 2001, 14, 119-125.
110. Hajnos, M.L.; Waksmundzka-Hajnos, M.; Glowniak, K.; Piasecka, S. Chromatographia 2002, 55, in press.
111. Bulatovic, V.; Vajs, V.; Matura, S.; Milosauljevic, S.; J. Natural Prod. 1997, 60, 1222-1228.
112. Lin, L.Z.; He, X.G.; Lian, L.Z.; King, W.; Eliott, J. J. Chromatogr. A 1997, 810, 71-79.
113. Tsevegsören, N.; Aitzetmöller, K. J. High Resol. Chromatogr. 1997, 20, 315-320.
114. Tauaka, T.; Shibata, K.; Hino, H.; Murashita, T.; Kayama, M.; Satouche, K. J. Chromatogr. B 1997, 700, 1-8.
115. Muthing, J.; Kemminer, S.E. Anal. Biochem. 1996, 238, 195-202.
116. Taki, T.; Kasama, T.; Handa, Sh.; Ishikawa, D. Anal. Biochem. 1994, 223, 232-238.
117. Aries, E.; Doumenq, P.; Artaud, J.; Molinet, J.; Bertrand, J.C. Org. Geochem. 2001, 32, 193-197.
118. Nguyen, H.; Ndjiiska, H. Fat. Sci. Technol. 1995, 97, 20-23.
119. Molkentin, J.; Precht, D. Chromatographia 1995, 41, 267-272.
120. Daulatabad, C.D.; Mulla, G.M.; Mirajkar, A.M. Fat. Sci. Technol. 1995, 97, 453-454.
121. Teng, J.I.; Made Gowda, N.M. Chromatographia 1993, 35, 627-630.
122. Sliwiok, J.; Kozera, A. J. Planar Chromatogr. 1991, 4, 336-337.
123. Mossoba, M.M.; McDonald, R.E.; Armstrong, D.J.; Page, S.W. J. Agric. Food Chem. 1991, 39, 695-699.
124. Aubourg, S.P.; Sotelo, C.G.; Gallordo, J.M. J. Agric. Food Chem. 1990, 38, 255-257.
125. Browsw, J.; Somerville, Ch.; Slack, C.R. Plant Sci. 1988, 56, 15-20.
126. Bandi, Z.L.; Ansari, G.A.S. J. Chromatogr. 1988, 435, 513-517.
127. Reine, A.H.; Stegnik, S.J. J. Chromatogr. 1988, 437, 211-219.
128. Tarandjilska, R.; Marekov, I.; Damyanov, B.N.; Amidzhin, B. J. Liquid Chromatogr. 1995, 18, 859-872.
129. Liu, Q.T.; Kinderlerer, J.L. J. Chromatogr. A. 1999, 855, 617-624.
130. Ilinov, P.P.; Deleva, D.D.; Dimov, S.I.; Zaprianova, E.T. J. Liq. Chromatogr. 1997, 20, 1149-1157.
131. Muthing, J.; Heitmann, D. Anal. Biochem. 1993, 208, 121-124.
132. Muthing, J.; Unland, F. Biomed. Chromatogr. 1993, 6, 227-230.
133. Muthing, J. Glycoconj. J. 1993, 10, 337-340.
134. Ilinov, P.; Katzarowa, E.; Dimov, S.; Zaprianova, E. J. Liq. Chromatogr. 1990, 13, 1921-1931.
135. Fujiwara, A.; Mori, T.; Iida, A.; Veda, S.; Hano, Y.; Nishino, H. J. Nat. Prod. 1998, 61, 629-632.
136. Broomhead, A.J.; Dewick, P.M. Phytochemistry 1991, 30, 1511-1517.
137. Jamazaki, T.; Flores, H.E.; Shimomura, K.; Yoshihira, K. J. Nat. Prod. 1991, 54, 986-992.
138. Chen, C.J.; Chang, F.R.; Chin, H.F.; Wu, M.J.; Wu, J.C. Phytochemistry 1999, 51, 429-433.
139. Hornero-Mendez, D.; Minhuez-Misquera, M.I. J. Agric. Food Chem. 1998, 46, 4087-4090.
140. Haugan, J.A.; Liaaen-Jensen, S. Biochem. Syst. Ecol. 1994, 22, 31-41.
141. Aczel, A. Acta Aliment. 1988, 17, 37-41.
142. Avato, P.; Vitali, C.; Mongelli, P.; Tava, A. Planta Med. 1997, 63, 503-507.
143. Bencsik, K.; Kremmer, T.; Boldizsar, M.; Tamás, J.; Mak, B.; Paldi, E. J. Chromatogr. A 1998, 824, 175-180.
144. He, X.; Lin, L.; Bernart, M.W.; Lian, L. J. Chromatogr. A 1998, 815, 205-211.
145. He, X.; Bernart, M.W.; Lian, L.; Lin, L. J. Chromatogr. A 1998, 796, 327-334.
146. Machida, K.; Trifonov, L.S.; Ayer, W.A.; Lu, Z.X.; Laroche, A. Phytochemistry 2001, 58, 173-177.
147. Tanahashi, T.; Takenaka, Y.; Nagakura, K.; Hamada, N. Phytochemistry 2001, 58, 1129-1134.
148. Macias, M.; Gamboa, A.; Ulloa, M.; Toscano, A.; Mata, R. Phytochemistry 2001, 58, 751-758.
149. Gliszczynska, A.; Koziolowa, A. J. Chromatogr. A 2000, 881, 285-297.
150. Gliszczynska, A.; Koziolowa, A. J. Chromatogr. A 1998, 822, 59-66.
151. Vela, J.; Vebolla, V.L.; Membrado, L.; Ferrando, A.C. J. Planar Chromatogr. 1998, 11, 277-282.
152. Fabianska, M.J. J. Planar Chromatogr. 1998, 11, 108-113.
153. Trypien, K.; Bodzek, D.; Janoszka, B. J. Planar Chromatogr. 1995, 8, 75-77.
154. Zulalian, J. J. Agric. Food Chem. 1990, 38, 1743-1754.
155. Mallipudi, N.M.; Stout, S.J.; Conha, A.R.; Lee, A.U. J. Agric. Food Chem. 1991, 39, 412-417.