Racemization of 6-methoxydihydrosanguinarine in methanol investigated by enantioselective dynamic HPLC

Journal of Pharmaceutical and Biomedical Analysis

Volumn 51, Issue 1, 2010, Pages 103-106

  Wu, Enqi ^a   Jung, Sang Hun ^a   Chen, Jianbo ^a   Kim, Young Ho ^a   Park, Kyung Lae ^a   Lee, Wonjae ^b   Kang, Jong Seong ^a  

^a Chungnam National University   (South Korea)

^b Chosun University   (South Korea)

Author keywords

6 Methoxydihydrosanguinarine; Chiral chromatography; Iminium ion intermediate; Interconversion; Racemization

Indexed keywords

6 METHOXYDIHYDROSANGUINARINE; ALKALOID DERIVATIVE; METHANOL; SANGUINARINE; UNCLASSIFIED DRUG;

ARTICLE; CHIRAL CHROMATOGRAPHY; CONTROLLED STUDY; DRUG SCREENING; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; RACEMIZATION;

BENZOPHENANTHRIDINES; CHEMISTRY, PHARMACEUTICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ISOQUINOLINES; METHANOL; PAPAVERACEAE; PLANT EXTRACTS; SOLVENTS; STEREOISOMERISM;

EID: 70349336672     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jpba.2009.08.014     Document Type: Article

References (32)

1. Chen J.J., Chang Y.L., Teng C.M., Lin W.Y., Chen Y.C., and Chen I.S. Planta Med. 67 (2001) 423-427
2. Zhang G.L., Ruecker G., Breitmaier E., and Mayer R. Phytochemistry 40 (1995) 1813-1816
3. Sener B., Gozler B., Minard R.D., and Shamma M. Phytochemistry 22 (1983) 2073-2075
4. Pandey V.B., Ray A.B., and Dasgupta B. Phytochemistry 18 (1979) 695-696
5. Kadan G., Gozler T., and Shamma M. J. Nat. Prod. 53 (1990) 531-532
6. Yin H.Q., Kim Y.H., Moon C.K., and Lee B.H. Biochem. Pharmacol. 70 (2005) 242-248
7. Lee Y.J., Yin H.Q., Kim Y.H., Li G.Y., and Lee B.H. Arch. Pharm. Res. 27 (2004) 1253-1257
8. Satou T., Akao N., Matsuhashi R., Koike K., Fujita K., and Nikaido T. Biol. Pharm. Bull. 25 (2002) 1651-1654
9. Matsuhashi R., Satou T., Koike K., Yokosuka A., Mimaki Y., Sashida Y., and Nikaido T. Planta Med. 68 (2002) 169-171
10. Y.S. Cho, Doctor's Thesis. Chungnam National University, 2001, p. 50.
11. Kang J.S., Long P.H., Lim H.M., Kim Y.H., and Gottfried B. Arch. Pharm. Res. 26 (2003) 114-119
12. Lee Y.N. Flora of Korea (1996), Kyohaksa, Seoul pp. 237-238
13. Trapp O., Trapp G., and Schurig V. J. Biochem. Biophys. Methods 54 (2002) 301-313
14. Trapp O., Caccamese S., Schmidt C., Bohmer V., and Schurig V. Tetrahedron Asymmetry 12 (2001) 1395-1398
15. Caccamese S., and Principato G. Tetrahedron Asymmetry 9 (1998) 2939-2945
16. Cabrera K., Jung M., Fluck M., and Schurig V. J. Chromatogr. A 731 (1996) 315-321
17. Trapp O., and Schurig V. Chirality 14 (2002) 465-470
18. Schurig V., Jung M., Schleimer M., and Klaerner F.G. Chem. Ber. 125 (1992) 1301-1303
19. Trapp O., Schoetz G., and Schurig V. J. Pharm. Biomed. Anal. 27 (2002) 497-505
20. Trapp O., and Schurig V. J. Am. Chem. Soc. 122 (2000) 1424-1430
21. Schoetz G., Trapp O., and Schurig V. Electrophoresis 22 (2001) 3185-3190
22. Schoetz G., Trapp O., and Schurig V. J. Capill. Electrophor. Microchip Technol. 6 (1999) 169-175
23. Gabriele S., Trapp O., and Schurig V. Enantiomer 5 (2000) 391-396
24. Trapp O., and Schurig V.J. J. Chromatogr. A 911 (2001) 167-175
25. Trapp O. Chirality 18 (2006) 489-497
26. Trapp O., and Schurig V. Comput. Chem. 25 (2001) 187-195
27. Trapp O. Anal. Chem. 78 (2006) 189-198
28. Trapp O., Schoetz G., and Schurig V. Chirality 13 (2001) 403-414
29. Fujii N., Momose Y., Ishii N., Takita M., Akaboshi M., and Kodama M. Mech. Age. Dev. 107 (1999) 347-358
30. In: Eliel E.L., Wilen S.H., and Mander L.N. (Eds). Stereochemistry of Organic Compounds (1994), John Wiley & Sons, New York 426
31. Chen J., Cantrell C.L., Shang H., and Rojas M.G. J. Agric. Food Chem. 57 (2009) 3128-3133
32. Schopf C., Koop H., Werner G., Braun F., and Franz. Chem. Ber. 93 (1960) 2457-2467