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Achiral and chiral determination of benzophenanthridine alkaloids from methanol extracts ofhylomecon species by high performance liquid chromatography

Abstract

A high performance liquid chromatographic (HPLC) method was developed for the qualitative and quantitative determination of benzophenanthridine alkaloids from the methanol extracts ofHylomecon hylomeconoides andH. 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 of1, 2 and3 within 20 min on ODS column using acetonitrile-phosphate buffer (50 mM, pH 7.0) (50 : 50, v/v). The separation and determination of1 and2 enantiomers was available using chiral columns. The same amount of (+) and (-)-enantiomers of1 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 of1 and3 in compared withH. vernale, especially in root samples permitting the possibility of chemical discrimination between two species.

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References

  • Chaturvedi, M. M., Kumar, A., Damay, B. G., Chainy, G. B. N., Agarwal, S., and Aggarwal, B. B., Sanguinarine (pseudochelerythrine) is a potent inhibitor of NF-kB activation, lkBα phosphorylation, and degradation.J. Biol. Chem., 272(48), 30129–30134 (1997).

    PubMed  Article  CAS  Google Scholar 

  • Cho, Y. S., Phytochemical constituents ofHylomecon hylomeconoides and their activities on neurotransmitter-metabolizing enzymes. Thesis: Chungnam National University (2001).

  • 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).

    Article  CAS  Google Scholar 

  • Dostal, J., Marek, R., Slavik, J., Taborska, E., Potacek, M., and Sklenar, V., Sanguinarine pseudobase: re-examination of NMR assignments using gradient-enhanced spectroscopy.Mag. Res. Chem., 36(11), 869–872 (1998).

    Article  CAS  Google Scholar 

  • 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 ofEschscholtzia californica.J. Chromatogr. A., 904(1), 3546 (2000).

    Article  Google Scholar 

  • Fletcher, M. T., Takken, G., Blaney, B. J., and Alberts, V., Isoquinoline alkaloids and keto-fatty acids ofArgemone 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).

    Article  CAS  Google Scholar 

  • Hiller, K. O., Ghorbani, M., and Schilcher, H., Antispasmodic and relaxant activity of chelidonine, protopine, coptisine, andChelidonium majus extracts on isolated guinea-pig ileum.Planta Med., 64(8), 758–760 (1998).

    PubMed  Article  CAS  Google Scholar 

  • 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).

    PubMed  Article  CAS  Google Scholar 

  • Itokawa, H., Ikuta, A., Tsutsui, N., and Ishiguro, I., Alkaloids and a sterol fromChelidonium japonicum.Phytochem., 17(4), 839–840 (1978).

    Article  CAS  Google Scholar 

  • Konda, Y., Harigaya, Y., and Onda, M., Studies on the constituents ofBocconia cordata. III. Structure elucidation of bocconine by means of nuclear magnetic resonance spectroscopic studies.J. Heterocyclic Chem., 23(3), 877–879 (1986).

    CAS  Article  Google Scholar 

  • 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 ofPapaver somniferum.Phytochem. Anal., 4(3), 103–104 (1993).

    Article  CAS  Google Scholar 

  • Lee, Y. N.,Flora of Korea, Kyohaksa, Seoul, pp. 237–238 (1996).

    Google Scholar 

  • Lenfeld, J., Kroutil, M., Marsalek, E., Slavik, J., Preininger, V., and Simanek, V., Antiinflammatory activity of quaternary benzophenanthridine alkaloids fromChelidonium majus.Planta Med., 43(2), 161–165 (1981).

    Article  CAS  Google Scholar 

  • 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).

    Article  Google Scholar 

  • Mitscher, L. A., Park, Y. H., Clark, D., and Clark, G. W., Hammesfahr, P. D., Wu, W. N., Beal, J. L., Antimicrobial agents from higher plants. An investigation ofHunnemannia fumariaefolia pseudoalcoholates of sanguinarine and chelerythrine.Lloydia, 41(2), 145–150 (1978).

    PubMed  CAS  Google Scholar 

  • Mizuno, M., Kojima, H., Tanaka, T., Linuma, M., Zhi-Da, M., and Murata, H., Benzophenanthridine alkaloids from the seeds ofCoptisjaponica var. dissecta.J. Nat. Prod., 50(2), 326 (1987).

    Article  CAS  Google Scholar 

  • 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).

    PubMed  Article  CAS  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • Pothier, J., Galand, N., Tivollier, P., and Viel, C., Separation of quaternary alkaloids in plant extracts by overpressured layer chromatography.J. Planar Chromatogr., 6(3), 220–222 (1993).

    CAS  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • Schumacher, H. M. and Zenk, M. H., Partial purification and characterization of dihydrobenzophenanthridine oxidase fromEschscholzia californica cell suspension cultures.Plant Cell Reports, 7(1), 43–46 (1988).

    Article  CAS  Google Scholar 

  • 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).

    PubMed  Article  CAS  Google Scholar 

  • Suresh, K. G., Das, A., and Maiti, M., Photochemical conversion of sanguinarine to oxysanguinarine.J. Photochem. Photobiol. A, 111(1–3), 51–56 (1997).

    Article  Google Scholar 

  • Tome, F., Colombo, M. L., and Caldiroli, L., A comparative investigation on alkaloid composition in different populations ofEschscholtzia californica Cham.Phytochem. Anal., 10(5), 264–267 (1999).

    Article  CAS  Google Scholar 

  • Williams, R. D. and Ellis, B. E., Alkaloids fromAgrobacterium rhizogenes-transformed Papaver somniferum cultures.Phytochem., 40(1), 719–723 (1995).

    Google Scholar 

  • Zhang, G. L., Rucker, G., Breitmaier, E., Nieger, M., Mayer, R., and Steinbeck, C., Alkaloids fromDactylicapnos torulosa.Phytochem., 32(3), 299–305 (1993).

    Google Scholar 

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Correspondence to Kang Jong Seong.

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Jong Seong, K., Pham Hoai, L., Hwan Mi, L. et al. Achiral and chiral determination of benzophenanthridine alkaloids from methanol extracts ofhylomecon species by high performance liquid chromatography. Arch Pharm Res 26, 114 (2003). https://doi.org/10.1007/BF02976654

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  • DOI: https://doi.org/10.1007/BF02976654

Key words

  • Benzophenanthridine alkaloids
  • Hylomecon species
  • Enantiomers
  • Chiral separation
  • HPLC