Analysis of tropane and related alkaloids

Fodor, 1990, Nat. Prod. Rep., 7, 539, 10.1039/np9900700539 Fodor, 1991, Nat. Prod. Rep., 8, 604, 10.1039/np9910800603 Fodor, 1993, Nat. Prod. Rep., 10, 199, 10.1039/np9931000199 Fodor, 1994, Nat. Prod. Rep., 11, 443, 10.1039/np9941100443 O’Hagan, 1997, Nat. Prod. Rep., 14, 637, 10.1039/np9971400637 Woolley, 1993, Vol. 8, 133 A. Baerheim Svendsen, R. Verpoorte, Chromatography of Alkaloids, Part A: TLC, Elsevier, Amsterdam, 1983, p. 91. A. Baerheim Svendsen, R. Verpoorte, Chromatography of Alkaloids, Part B: GC, HPLC, Elsevier, Amsterdam, 1984, p. 61. Baerheim Svendsen, 1989, J. Planar. Chromatogr. Modern TLC, 2, 8 Popl, 1990 1994, 113 Verpoorte, 1994, Phytochem. Anal., 5, 217, 10.1002/pca.2800050502 Clarke, 1977, Vol. 16, 83 Lounasmaa, 1988, 2 Lounasmaa, 1993, Vol. 44, 1 Griffin, 2000, Phytochemistry, 53, 623, 10.1016/S0031-9422(99)00475-6 Robinson, 1981, 58 Cordell, 1981, 80 Hemscheidt, 2000, Topics Curr. Chem., 209, 175, 10.1007/3-540-48146-X_4 Asano, 2000, Tetrahedron, 11, 1645, 10.1016/S0957-4166(00)00113-0 Asano, 2001, Phytochemistry, 57, 721, 10.1016/S0031-9422(01)00131-5 Brachet, 1999, Analusis, 27, 772, 10.1051/analusis:1999143 Payne, 1987, Planta Med., 53, 474, 10.1055/s-2006-962776 Buech, 1994, Methods Find Exp. Clin. Pharmacol., 16, 361 Oertel, 1996, J. Chromatogr. B, 682, 259, 10.1016/0378-4347(96)00095-3 Auriola, 1991, J. Chromatogr., 562, 737, 10.1016/0378-4347(91)80622-J Ylinen, 1986, Planta Med., 52, 85, 10.1055/s-2007-969086 Plank, 1986, Z. Naturforsch. Series C, 41c, 391, 10.1515/znc-1986-0404 Papadoyannis, 1993, J. Liq. Chromatogr., 16, 975, 10.1080/10826079308019565 Hüller, 1993, Pharmazie, 48, 548 El-Shazly, 1997, Z. Naturforsch. C, J. Biosci., 52, 729, 10.1515/znc-1997-11-1203 Hartmann, 1986, Planta Med., 52, 390, 10.1055/s-2007-969194 Gontier, 1994, Plant Cell Reports, 13, 533, 10.1007/BF00232951 Moeller, 1998, J. Chromatogr. B, 713, 91, 10.1016/S0378-4347(97)00573-2 Logan, 1990, J. Anal. Toxicol., 14, 154, 10.1093/jat/14.3.154 Portsteffen, 1994, Phytochemistry, 37, 391, 10.1016/0031-9422(94)85066-6 Draeger, 1994, Phytochemistry, 35, 1441, 10.1016/S0031-9422(00)86871-5 Schneider, 1995, Phytochemistry, 39, 1387, 10.1016/0031-9422(95)00147-Y Keiner, 2000, Plant Sci., 150, 171, 10.1016/S0168-9452(99)00184-3 Draeger, 1995, Planta Med., 61, 577, 10.1055/s-2006-959381 Bumke, 1996, Phycologia, 35, 51, 10.2216/i0031-8884-35-6S-51.1 James, 1998, J. Chromatogr. A, 798, 147, 10.1016/S0021-9673(97)01207-7 Harada, 1993, Tetrahedron, 49, 9251, 10.1016/0040-4020(93)80011-H Lloyd, 1960, J. Am. Chem. Soc., 82, 3791, 10.1021/ja01499a084 Brochmann-Hanssen, 1962, J. Pharm. Sci., 51, 1095, 10.1002/jps.2600511119 Achari, 1971, Planta Med., 19, 241, 10.1055/s-0028-1099637 Solomon, 1969, J. Pharm. Sci., 58, 264, 10.1002/jps.2600580234 Liebisch, 1973, Z. Chem., 13, 169 Majlat, 1982, J. Chromatogr., 241, 399, 10.1016/S0021-9673(00)81766-5 Briggs, 1983, J. Chromatogr., 257, 132, 10.1016/S0021-9673(01)88163-2 Majlat, 1984, Pharmazie, 39, 325 Wilms, 1977, Planta Med., 31, 249, 10.1055/s-0028-1097523 Brachet, 1981, Physiol. Vég., 19, 77 Yamada, 1982, Plant Cell Reports, 1, 101, 10.1007/BF00272363 Hashimoto, 1983, Planta Med., 47, 195, 10.1055/s-2007-969984 Yamada, 1984, Plant Cell Reports, 3, 166, 10.1007/BF00270196 Blossey, 1964, Tetrahedron, 20, 585, 10.1016/S0040-4020(01)98621-1 Kan-Fan, 1973, Acta Chem. Scand., 27, 1039, 10.3891/acta.chem.scand.27-1039 Green, 1982, Proc. West. Pharmacol. Soc., 25, 15 Grob, 1995 Grob, 1993 Grob, 1991 Witte, 1987, Planta Med., 53, 192, 10.1055/s-2006-962670 Kovats, 1958, Helv. Chim. Acta, 41, 1915, 10.1002/hlca.19580410703 R. Zarate, B. Hermosin, M. Cantos, A. Troncoso, J. Chem. Ecol., (1997) 2059. Rocha, 2002, Plant Sci., 162, 905, 10.1016/S0168-9452(02)00033-X Stevens, 1993, Plant System. Evol., 185, 207, 10.1007/BF00937658 Stevens, 1992, Phytochemistry, 31, 3917, 10.1016/S0031-9422(00)97554-X Kim, 1996, Phytochemistry, 41, 1319, 10.1016/0031-9422(95)00562-5 Lora-Tamayo, 1986, J. Chromatogr., 374, 73, 10.1016/S0378-4347(00)83254-5 Vitale, 1995, J. Ethnopharm., 49, 81, 10.1016/0378-8741(95)90035-7 Christen, 1989, Plant Cell Reports, 8, 75, 10.1007/BF00716842 Christen, 1990, Plant Cell Reports, 9, 101, 10.1007/BF00231559 Dupraz, 1993, Planta Med., 60, 158, 10.1055/s-2006-959441 Herouart, 1987, Planta Med., 53, 14 Doerk, 1991, Z. Naturforsch. C, 46, 519, 10.1515/znc-1991-7-803 Doerk, 1994, Phytochemistry, 35, 107, 10.1016/S0031-9422(00)90517-X Robins, 1990, Planta, 181, 414, 10.1007/BF00195896 Parr, 1990, Phytochemistry, 29, 2545, 10.1016/0031-9422(90)85185-I Hashimoto, 1985, J. Plant Physiol., 124, 61, 10.1016/S0176-1617(86)80178-X Robins, 1991, Planta, 183, 185, 10.1007/BF00197787 Robins, 1991, Planta, 183, 196, 10.1007/BF00197788 Robins, 1991, Planta, 185, 385, 10.1007/BF00201061 Zabetakis, 1999, Phytochemistry, 50, 53, 10.1016/S0031-9422(98)00490-7 Sharp, 1990, J. Biotechnol., 16, 171, 10.1016/0168-1656(90)90034-9 Aoki, 1997, Plant Cell Reports, 16, 282 Nakanishi, 1998, Plant Cell Reports, 18, 249, 10.1007/s002990050565 Nakanishi, 2000, Plant Cell Reports, 19, 1021, 10.1007/s002990000231 Hashimoto, 1993, Phytochemistry, 32, 713, 10.1016/S0031-9422(00)95159-8 Zarate, 1999, Plant Cell Reports, 18, 418, 10.1007/s002990050596 Yukimune, 1994, Biosci. Biotechnol. Biochem., 58, 1447, 10.1271/bbb.58.1447 Yukimune, 1994, Biosci. Biotechnol. Biochem., 58, 1820, 10.1271/bbb.58.1820 Yukimune, 1994, Biosci. Biotechnol. Biochem., 58, 1824, 10.1271/bbb.58.1824 Draeger, 1992, Planta, 188, 581 Portsteffen, 1992, Phytochemistry, 31, 1135, 10.1016/0031-9422(92)80247-C Martinsen, 1992, Phytochem. Anal., 3, 69, 10.1002/pca.2800030206 Neuhöfer, 1993, Pharmazie, 48, 389 Christen, 1993, Phytochemistry, 34, 1147, 10.1016/S0031-9422(00)90733-7 Christen, 1995, Phytochemistry, 38, 1053, 10.1016/0031-9422(94)00777-Q Brachet, 1997, Phytochemistry, 46, 1439, 10.1016/S0031-9422(97)00506-2 Moore, 1994, J. Chromatogr. A, 659, 163, 10.1016/0021-9673(94)85018-6 Moore, 1994, J. Chromatogr. A, 674, 165, 10.1016/0021-9673(94)85224-3 Casale, 1994, J. Forensic. Sci., 39, 1537 Casale, 1996, J. Chromatogr. A, 749, 173, 10.1016/0021-9673(96)00466-9 Casale, 1996, J. Chromatogr. A, 756, 185, 10.1016/S0021-9673(96)00672-3 Goenechea, 1986, Fresenius Z. Anal. Chem, 323, 326, 10.1007/BF00474594 Moore, 1996, J. Chromatogr. A, 756, 193, 10.1016/S0021-9673(96)00651-6 Lurie, 1990, J. Chromatogr., 504, 391, 10.1016/S0021-9673(01)89542-X Moore, 1997, J. Forensic Sci., 42, 246 Robins, 1993, Vol. 44, 115 Hashimoto, 1994, Ann. Rev. Plant Physiol. Plant Mol. Biol., 45, 257, 10.1146/annurev.pp.45.060194.001353 Hashimoto, 1993, Vol. 9, 369 Robins, 1991, FEBS Lett., 292, 293, 10.1016/0014-5793(91)80887-9 Robins, 1994, Plant Cell Tiss. Organ Cult., 38, 241, 10.1007/BF00033883 Rabot, 1995, Phytochemistry, 39, 315, 10.1016/0031-9422(94)00907-B Zabetakis, 1998, Plant Cell Reports, 18, 53, 10.1007/s002990050583 Robins, 1994, Planta, 194, 86, 10.1007/BF00201038 Chesters, 1994, J. Chem. Soc. Perkin Trans., 1, 1159, 10.1039/p19940001159 Robins, 1994, J. Chem. Soc. Perkin Trans., 1, 615, 10.1039/p19940000615 Robins, 1995, J. Chem. Soc. Perkin Trans., 1, 481, 10.1039/p19950000481 Chesters, 1995, J. Chem. Soc., 2, 127 O’Hagen, 1998, Chem. Soc. Rev., 27, 207, 10.1039/a827207z C.W. Wong, J.T.G. Hamilton, D. O’Hagen, R.J. Robins, Chem. Commun., (1998) 1045. O’Hagen, 1999, J. Chem. Soc., 1, 2117 Robins, 1997, J. Am. Chem. Soc., 119, 10929, 10.1021/ja964461p Boswell, 1999, Phytochemistry, 52, 855, 10.1016/S0031-9422(99)00292-7 Boswell, 1999, Phytochemistry, 52, 871, 10.1016/S0031-9422(99)00293-9 Ferreira-Jorge, 1998, Int. J. Plant Sci., 159, 492, 10.1086/297566 Glass, 1997, J. Agric. Food Chem., 45, 3114, 10.1021/jf960967f R. Oertel, K. Richter, U. Ebert, W. Kirch, Personal communication, 1999. Puchta, 1996, J. Pharm. Sci., 85, 899, 10.1021/js950327b Kaila, 1999, Acta Ophtal. Scand., 77, 193, 10.1034/j.1600-0420.1999.770215.x Kuhlmann, 1999, Toxicol. Sci., 48, 107, 10.1093/toxsci/48.1.107 Kung, 1999, J. Nucl. Med., 40, 660 Verebey, 1989, J. Forensic Sci., 34, 46, 10.1520/JFS12609J Little, 1995, Am. J. Obstet. Gynecol., 172, 1441, 10.1016/0002-9378(95)90475-1 Harkey, 1993, Forensic Sci. Int., 63, 9, 10.1016/0379-0738(93)90255-9 Harkey, 1991, J. Anal. Toxicol., 15, 260, 10.1093/jat/15.5.260 Henderson, 1992, J. Anal. Toxicol., 16, 199, 10.1093/jat/16.3.199 Henderson, 1998, J. Anal. Toxicol., 22, 156, 10.1093/jat/22.2.156 Kintz, 1995, J. Forensic Sci., 73, 93, 10.1016/0379-0738(95)01725-X Segura, 1999, J. Chromatogr. B, 724, 9, 10.1016/S0378-4347(98)00531-3 Henderson, 1996, J. Anal. Toxicol., 20, 1, 10.1093/jat/20.1.1 Gaillard, 1999, J. Chromatogr. B, 733, 231, 10.1016/S0378-4347(99)00263-7 Moore, 1995, J. Chromatogr. A, 704, 483, 10.1016/0021-9673(95)00219-D Casale, 1994, J. Forensic Sci., 39, 462 Casale, 1998, J. Forensic Sci., 43, 125, 10.1520/JFS16099J Casale, 1995, J. Forensic Sci., 40, 816 Goldmann, 1990, Phytochemistry, 29, 2125, 10.1016/0031-9422(90)83019-W Molyneux, 1993, Arch. Biochem. Biophys., 304, 81, 10.1006/abbi.1993.1324 Asano, 1995, Eur. J. Biochem., 229, 369, 10.1111/j.1432-1033.1995.0369k.x Asano, 1997, Glycobiology, 7, 1085, 10.1093/glycob/7.8.1085 Molyneux, 1996, Vol. 11, 303 Draeger, 1995, Phytochem. Anal., 6, 31, 10.1002/pca.2800060105 Sevon, 1997, Plant Cell Reports, 16, 605, 10.1007/BF01275500 Bekkouche, 2001, Phytochemistry, 58, 455, 10.1016/S0031-9422(01)00283-7 Rothe, 2001, Plant Sci., 160, 1043, 10.1016/S0168-9452(01)00355-7 Schimming, 1998, Phytochemistry, 49, 1989, 10.1016/S0031-9422(98)00430-0 Keiner, 2000, J. Appl. Bot., 74, 122 Keiner, 2002, Plant Mol. Biol., 48, 299, 10.1023/A:1013315110746 Scholl, 2001, Phytochemistry, 58, 883, 10.1016/S0031-9422(01)00362-4 W.W. Carmichael, Sci. Am. (1994) 64. Zotou, 1993, Analyst, 118, 753, 10.1039/AN9931800753 Stutz, 1973, Anal. Chem., 45, 2134, 10.1021/ac60334a036 Verpoorte, 1976, J. Chromatogr., 120, 203, 10.1016/S0021-9673(01)99014-4 Jatlow, 1978, J. Chromatogr., 152, 115, 10.1016/S0021-9673(00)85340-6 Baerheim Svendsen, 1984, 249 Pekic, 1985, Pharmazie, 40, 422 Mano, 1986, Agric. Biol. Chem., 50, 2715, 10.1271/bbb1961.50.2715 Pitta, 2000, Enzyme Micr. Technol., 26, 252, 10.1016/S0141-0229(99)00137-4 Fliniaux, 1993, J. Chromatogr., 644, 193, 10.1016/0021-9673(93)80130-Z Gontier, 1993, Planta Med., 59, 432, 10.1055/s-2006-959726 He, 1989, J. Chromatogr., 481, 428, 10.1016/S0021-9673(01)96791-3 Mano, 1989, Plant Sci., 59, 191, 10.1016/0168-9452(89)90137-4 Oshima, 1989, Chem. Pharm. Bull., 37, 2456, 10.1248/cpb.37.2456 Sauerwein, 1992, J. Plant Physiol., 140, 147, 10.1016/S0176-1617(11)80925-9 Oshima, 1991, J. Chromatogr., 547, 175, 10.1016/S0021-9673(01)88641-6 Mandal, 1991, J. Chromatogr., 547, 468, 10.1016/S0021-9673(01)88674-X Hibi, 1992, Plant Physiol., 100, 826, 10.1104/pp.100.2.826 Bogusz, 1994, J. Chromatogr. A, 674, 97, 10.1016/0021-9673(94)85220-0 Leroy, 1987, J. Pharm. Biomed. Anal., 5, 477, 10.1016/0731-7085(87)80056-0 Lin, 1993, J. Chromatogr., 632, 69, 10.1016/0021-9673(93)80027-6 Lau, 1996, J. Chromatogr. A, 766, 270, 10.1016/S0021-9673(96)01019-9 Takahashi, 1997, J. Chromatogr. A, 775, 137, 10.1016/S0021-9673(97)00305-1 Holeman, 1995, J. Chromatogr. Sci., 33, 297, 10.1093/chromsci/33.6.297 Dost, 2000, J. Biochem. Biophys. Methods, 43, 125, 10.1016/S0165-022X(00)00055-5 Ceyhan, 2001, J. Pharm. Biomed. Anal., 25, 399, 10.1016/S0731-7085(00)00514-8 Szasz, 1999, J. Liq. Chromatogr. Rel. Technol., 22, 747, 10.1081/JLC-100101696 Pohjola, 1994, J. Chromatogr. A, 686, 350, 10.1016/0021-9673(94)00780-2 Okuda, 1991, J. Chromatogr., 567, 141, 10.1016/0378-4347(91)80318-7 Larsen, 1992, J. Forensic Sci., 37, 636, 10.1520/JFS13272J Sachs, 1998, J. Chromatogr. B, 713, 147, 10.1016/S0378-4347(98)00168-6 Heldin, 1992, J. Chromatogr., 592, 339, 10.1016/0021-9673(92)85105-3 Arvidsson, 1990, J. Chromatogr., 506, 579, 10.1016/S0021-9673(01)91606-1 Hampe, 1993, J. Chromatogr., 634, 205, 10.1016/0021-9673(93)83006-E Blaschke, 1993, Chirality, 5, 78, 10.1002/chir.530050207 Stalcup, 1991, Biomed. Chromatogr., 5, 3, 10.1002/bmc.1130050103 Tang, 1996, Chriality, 8, 136, 10.1002/(SICI)1520-636X(1996)8:1<136::AID-CHIR20>3.0.CO;2-N Tachibana, 2001, J. Chromatogr. A, 906, 127, 10.1016/S0021-9673(00)00955-9 Donaldson, 1990, Phytochem. Anal., 1, 18, 10.1002/pca.2800010103 B. Draeger, unpublished results, 2002. Powell, 1997, Chromatographia, 45, 25, 10.1007/BF02505532 James, 1996, Biomed. Chromatogr., 10, 46, 10.1002/(SICI)1099-0801(199601)10:1<46::AID-BMC551>3.0.CO;2-7 Meyer, 1999 Altria, 1998, 853 Wang, 1998, 791 Snopek, 1990, Electrophoresis, 11, 757, 10.1002/elps.1150110913 Fanali, 1990, Electrophoresis, 11, 757, 10.1002/elps.1150110913 Terabe, 1992, J. Pharm. Biomed. Anal., 10, 705, 10.1016/0731-7085(91)80069-L Guttmann, 1988, J. Chromatogr., 448, 41, 10.1016/S0021-9673(01)84564-7 Cruzado, 1992, J. Chromatogr., 608, 421, 10.1016/0021-9673(92)87150-7 Rawjee, 1994, J. Chromatogr. A, 688, 273, 10.1016/0021-9673(94)00888-4 Rawjee, 1994, J. Chromatogr. A, 680, 599, 10.1016/0021-9673(94)85160-3 Nassar, 1998, J. Chromatogr. Sci., 36, 19, 10.1093/chromsci/36.1.19 Wedig, 1999, Electrophoresis, 20, 1555, 10.1002/(SICI)1522-2683(19990601)20:7<1555::AID-ELPS1555>3.0.CO;2-F Mateus, 2000, J. Chromatogr. A, 868, 285, 10.1016/S0021-9673(99)01230-3 Jin, 1999, Electrophoresis, 20, 198, 10.1002/(SICI)1522-2683(19990101)20:1<198::AID-ELPS198>3.0.CO;2-7 Tahara, 1999, J. Chromatogr. A, 848, 465, 10.1016/S0021-9673(99)00447-1 Lurie, 1998, Electrophoresis, 19, 51, 10.1002/elps.1150190110 Mateus, 1999, Electrophoresis, 20, 3402, 10.1002/(SICI)1522-2683(19991101)20:17<3402::AID-ELPS3402>3.0.CO;2-E Cherkaoui, 2001, Electrophoresis, 22, 3308, 10.1002/1522-2683(200109)22:15<3308::AID-ELPS3308>3.0.CO;2-H Tomas-Barberan, 1995, Phytochem. Anal., 6, 177, 10.1002/pca.2800060402 Cherkaoui, 1997, J. Chromatogr. B, 696, 283, 10.1016/S0378-4347(97)00255-7 Cherkaoui, 1998, J. Pharm. Biomed. Anal., 17, 1167, 10.1016/S0731-7085(98)00083-1 Eeva, 1998, J. Pharm. Biomed. Anal., 16, 717, 10.1016/S0731-7085(97)00121-0 Baricevic, 1999, Environm. Exp. Botany, 42, 17, 10.1016/S0098-8472(99)00014-3 Daali, 2000, J. Chromatogr. A, 903, 237, 10.1016/S0021-9673(00)00902-X Ruttinger, 2001, J. Chromatogr. A, 925, 291, 10.1016/S0021-9673(01)01023-8 Vindervogel, 1992 Cherkaoui, 1997, Chromatographia, 46, 351, 10.1007/BF02490872 Mateus, 1998, J. Pharm. Biomed. Anal., 18, 815, 10.1016/S0731-7085(98)00223-4 Wu, 1998, J. Chromatogr. A, 802, 107, 10.1016/S0021-9673(97)01141-2 Mateus, 1998, J. Chromatogr. A, 829, 317, 10.1016/S0021-9673(98)00741-9 Plaut, 1998, Electrophoresis, 19, 3003, 10.1002/elps.1150191634 Mateus, 2000, Phytochemistry, 54, 517, 10.1016/S0031-9422(00)00134-5 Cherkaoui, 1998, Electrophoresis, 19, 2900, 10.1002/elps.1150191617 Cherkaoui, 1999, Chromatographia, 49, 54, 10.1007/BF02467187 Geiss, 1987 Nyiredy, 1988, J. Planar Chromatogr. Modern TLC, 1, 336 Botz, 1988, J. Planar Chromatogr. Modern TLC, 1, 85 Stevens, 1995, Biochem. System. Ecol., 23, 157, 10.1016/0305-1978(95)00082-6 Draeger, 1988, Agric. Biol. Chem., 52, 2663, 10.1271/bbb1961.52.2663 Tepfer, 1988, J. Bacteriol., 170, 1153, 10.1128/jb.170.3.1153-1161.1988 Polesuk, 1971, J. Chromatogr., 57, 315, 10.1016/0021-9673(71)80047-X Asano, 2001, J. Agric. Food Chem., 49, 4208, 10.1021/jf010567e Scholl, 2001, J. Chromatogr. A, 928, 217, 10.1016/S0021-9673(01)01128-1 Pothier, 1991, J. Planar Chromatogr. Modern TLC, 4, 392 Pothier, 1993, J. Planar Chromatogr. Modern TLC, 6, 220 Monforte, 1992, Phytochem. Anal., 3, 117, 10.1002/pca.2800030305 Funk, 1991, J. Planar Chromatogr. Modern TLC, 4, 123 Scholl, 2001, Planar Chromatogr., 87, 10 Farwell, 1981, J. Chromatogr. Sci., 19, 358, 10.1093/chromsci/19.7.358 Landrock, 1995, Fresenius J. Anal. Chem, 351, 536, 10.1007/BF00322729 Paul, 1995, Z. Naturforsch. C, 8, 446 Nishi, 1990, J. Chromatogr., 515, 233, 10.1016/S0021-9673(01)89318-3 Kelly, 1998, 277 O’Neil, 2001 Beilstein Institut zur Förderung der Chemischen Wissenschaften, Beilstein CrossFire, Beilstein Chemie Daten und Software and MDL Information Systems, 2002. 1993 Reynolds, 1989 Muhtadi, 1986, Vol. 15, 153 Muhtadi, 1990, Vol. 19, 478 Miyazaki, 1993, Yakugaku Zasshi, 113, 376, 10.1248/yakushi1947.113.5_376