Achiral and Chiral Determination of Benzophenanthridine Alkaloids from Methanol Extracts of Hylomecon Species by High Performance Liquid Chromatography

  • Published : 2003.02.01

Abstract

A high performance liquid chromatographic (HPLC) method was developed for the qualitative and quantitative determination of benzophenanthridine alkaloids from the methanol extracts of Hylomecon hylomeconoides and H. vernale (Papaveraceae). Achiral and chiral methods were adapted for the separation of 6-methoxydihydrosanguinarine (1), 6-acetonyldihydrosanguinarine (2) and dihydrosanguinarine (3). The achiral reversed phase HPLC method made it possible the simultaneous separation and determination of 1, 2 and 3 within 20 min on ODS column using acetonitrile-phosphate buffer (50 mM, pH 7.0) (50 : 50, v/v). The separation and determination of 1 and 2 enantiomers was available using chiral columns. The same amount of (+) and (-)-enantiomers of 1 was found from the methanol extract of specimen, indicated that 1 could be the artifact produced by the reaction of sanguinarine with methanol. H. hylomeconoides showed higher level of 1 and 3 in compared with H. vernale, especially in root samples permitting the possibility of chemical discrimination between two species.

Keywords

References

  1. Chaturvedi, M. M., Kumar, A., Darnay, B. G., Chainy, G. B. N., Agarwal, S., and Aggarwal, B. B., Sanguinarine (pseudochelerythrine) is a potent inhibitor of NF-$\kappa$B activation, I$\kappa$B$\alpha$ phosphorylation, and degradation. J. Biol. Chem., 272(48), 30129-30134 (1997) https://doi.org/10.1074/jbc.272.48.30129
  2. Cho, Y. S., Phytochemical constituents of Hylomecon hylomeconoides and their activities on neurotransmitter-metabolizing enzymes. Thesis: Chungnam National University (2001)
  3. Dostal, J., Bochorakova, H., Taborska, E., Slavik, J., Potacek, M., Budesinsky, M., and de Hoffmann, E., Structure of sanguinarine base. J. Nat. Prod., 59(6), 599-602 (1996) https://doi.org/10.1021/np960356h
  4. Dostal, J., Marek, R., Slavik, J., Taborska, E., Potacek, M., and M., Sklenar, V., Sanguinarine pseudobase: re-examination of NMR assignments using gradient-enhanced spectroscopy. Mag. Res. Chem., 36(11), 869-872 (1998) https://doi.org/10.1002/(SICI)1097-458X(1998110)36:11<869::AID-OMR380>3.0.CO;2-8
  5. Fabre, N., Claparols, C., Richelme, S., Angelin, M. L., Fouraste, I., and Moulis, C., Direct characterization of isoquinoline alkaloids in a crude plant extract by ion-pair liquid chromatography-electrospray ionization tandem mass spectrometry: example of Eschscholtzia californica. J. Chromatogr. A, 904(1), 35-46 (2000) https://doi.org/10.1016/S0021-9673(00)00919-5
  6. Fletcher, M. T., Takken, G., Blaney, B. J., and Alberts, V., Isoquinoline alkaloids and keto-fatty acids of Argemone ochroleuca and A. mexicana (Mexican poppy) seed. I. An assay method and factors affecting their concentration. Aust. J. Agric. Res., 44(2), 265-275 (1993) https://doi.org/10.1071/AR9930265
  7. Hiller, K. O., Ghorbani, M., and Schilcher, H., Antispasmodic and relaxant activity of chelidonine, protopine, coptisine, and Chelidonium majus extracts on isolated guinea-pig ileum. Planta Med., 64(8), 758-760 (1998) https://doi.org/10.1055/s-2006-957576
  8. Husain, S., Narsimha, R., and Rao, R. N., Separation, identification and determination of sanguinarine in argemone and other adulterated edible oils by reversed-phase high-performance liquid chromatography. J. Chromatogr. A, 863(1), 123-126 (1999) https://doi.org/10.1016/S0021-9673(99)00964-4
  9. Itokawa, H., Ikuta, A., Tsutsui, N., and Ishiguro, I., Alkaloids and a sterol from Chelidonium japonicum. Phytochem., 17(4), 839-840 (1978) https://doi.org/10.1016/S0031-9422(00)94262-6
  10. Konda, Y., Harigaya, Y., and Onda, M., Studies on the constituents of Bocconia cordata. III. Structure elucidation of bocconine by means of nuclear magnetic resonance spectro-scopic studies. J. Heterocyclic Chem., 23(3), 877-879 (1986) https://doi.org/10.1002/jhet.5570230342
  11. Kraml, M. M. and DiCosmo, F., A rapid high-performance liquid chromatographic method for the separation of the alkaloid precursor L-tyrosine and six tetrahydroisoquinoline alkaloids of Papaver somniferum. Phytochem. Anal., 4(3), 103-104 (1993) https://doi.org/10.1002/pca.2800040304
  12. Lee, Y. N., Flora of Korea, Kyohaksa, Seoul, pp. 237-238 (1996)
  13. Lenfeld, J., Kroutil, M., Marsalek, E., Slavik, J., Preininger, V., and Simanek, V., Antiinflammatory activity of quaternary benzophenanthridine alkaloids from Chelidonium majus. Planta Med., 43(2), 161-165 (1981) https://doi.org/10.1055/s-2007-971493
  14. Marek, R., Tousek, J., Kralik, L., Dostal, J., and Sklenar, V., Conformational study of C2 symmetrical benzo[c]phenanthridine alkaloid derivatives. Chem. Lett., 4, 369-370 (1997)
  15. Mitscher, L. A., Park, Y H., Clark, D., and Clark, G. W. 3rd, Hammesfahr, P. D., Wu, W. N., Beal, J. L., Antimicrobial agents from higher plants. An investigation of Hunnemannia fumariaefolia pseudoalcoholates of sanguinarine and chelerythrine. Lloydia, 41(2), 145-150 (1978)
  16. Mizuno, M., Kojima, H., Tanaka, T., linuma, M., Zhi-Da, M., and Murata, H., Benzophenanthridine alkaloids from the seeds of Coptis japonica var. dissecta. J. Nat. Prod., 50(2), 326 (1987) https://doi.org/10.1021/np50050a055
  17. Nakanishi, T., Suzuki, M., Saimoto, A., and Kabasawa, T., Structural considerations of NK109, an antitumor benzo[c] phenanthridine alkaloid. J. Nat. Prod., 62(6), 864-867 (1999) https://doi.org/10.1021/np990005d
  18. Oechslin, S. M., Konig, G. M., Oechslin-Merkel, K., Wright, A. D., Kinghorn, A. D., Sticher, O., and Miyagawa, M., An NMR study of four benzophenanthridine alkaloids. J. Nat. Prod., 54(2), 519-524 (1991) https://doi.org/10.1021/np50074a026
  19. Pothier, J., Galand, N., Tivollier, P., and Viel, C., Separation of quaternary alkaloids in plant extracts by overpressured layer chromatoqraphy. J. Planar Chromatogr., 6(3), 220-222 (1993)
  20. Schmeller, T., Latz-Bruning, B., and Wink, M., Biochemical activities of berberine, palmatine and sanguinarine mediating chemical defence against microorganisms and herbivores. Phytochem., 44(2), 257-266 (1997) https://doi.org/10.1016/S0031-9422(96)00545-6
  21. Schumacher, H. M. and Zenk, M. H., Partial purification and characterization of dihydrobenzophenanthridine oxidase from Eschscholzia californica cell suspension cultures. Plant Cell Reports, 7(1), 43-46 (1988) https://doi.org/10.1007/BF00272975
  22. Sevcik, J., Vicar, J., Ulrichova, J., Valka, I., Lemr, K., and Simanek, V., Capillary electrophoretic determination of sanguinarine and chelerythrine in plant extracts and pharmaceutical preparations. J. Chromatogr. A, 866(2), 293-298 (2000) https://doi.org/10.1016/S0021-9673(99)01126-7
  23. Suresh, K. G., Das, A., and Maiti, M., Photochemical conversion of sanguinarine to oxysanguinarine. J. Photochem. Photobiol. A, 111(1-3), 51-56 (1997) https://doi.org/10.1016/S1010-6030(97)00246-3
  24. Tome, F., Colombo, M. L., and Caldiroli, L., A comparative investigation on alkaloid composition in different populations of Eschscholtzia californica Cham. Phytochem. Anal., 10(5), 264-267 (1999) https://doi.org/10.1002/(SICI)1099-1565(199909/10)10:5<264::AID-PCA469>3.0.CO;2-4
  25. Williams, R. D. and Ellis, B. E., Alkaloids from Agrobacterium rhizogenes-transformed Papaver somniferum cultures. Phytochem., 40(1), 719-723 (1995)
  26. Zhang, G. L., Rucker, G., Breitmaier, E., Nieger, M., Mayer, R., and Steinbeck, C., Alkaloids from Dactylicapnos torulosa. Phyfochem., 32(3), 299-305 (1993)