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Structure-activity relationship of triterpenoids isolated fromMitragyna stipulosa on cytotoxicity

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Abstract

Chromatographic separation of the stem bark extract ofMitragyna stipulosa afforded triterpene derivatives ursolic acid (1), quinovic acid (2), quinivic acid 3-0-β-D-glucopyranoside (3, quinovin glycoside C), quinovic acid 3-0-[(2-0-sulfo)-β-D-quinovopyranoside] (4, zygophyloside D) and quinovic acid 3-0-β-D-quinovopyranosyl-27-0-β-D-glucopyranosyl ester (5, zygophyloside B). These five compounds were subjected to the cytotoxicity on MTT assay system. Compound1 among tested showed the most potent cytotoxicity. Quinovic acid showed less potent cytotoxicity than ursolic acid and sugar linkages to2 decreased the cytotoxicity. Compound4 more potent than3 with indicate that the sulfonyl group significantly enhances the activity. This indicates that the glycosidic linkage in ursane-type triterpenoids has mainly negative effect on cytotoxicity unlike in oleanane-type glycosides.

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References

  1. Ahmad, V. U. and Rahman, A. U., Handbook of Natural Products Data, Vol II, pp. 835–836, Elsevier Science, Amsterdam (1994).

  2. Ahmad, V. U. and Basha, A., Spectroscopic data of saponins- The triterpenoid glycosides Vol. Ill, pp. 2839–2839, CRC press, New York (2000).

  3. Aquino, Q., Simone, F. D., Pizza, C., Cerri, R. and de Mello, J. F., Plant metabolites. Structure and in vitro antiviral activity of quinovic acid glycosides fromUncaria tomentosa andGuettarda platypoda. Journal of Natural Products 52, 679–685 (1989).

  4. Denizot, F and Lang, R. J., Rapid colorimetric assay for cell growth and survival: modification to the tetrazolium dye procedure giving improved sensitivity and reliability.Journal of Immunological Methods, 89, 271–277 (1996).

  5. Kim, Y. K., Yoon, S. K., Ryu, S., Cytotoxic triterpenes from stem bark ofPhysocarpus intermedius. Planta Medica, 66, 485–486 (2000).

  6. Lee, K. T., Sohn I. C., Park, H. J., Kim, D.W., Jung, G. O. and Park. K. Y., Essential moiety for antimutagenic and cytotoxic activity of hederagenin monodesmosides Isolated from the stem bark ofKalopanax pictus. Planta Medica, 66, 329–332 (2000).

  7. Park, H. J., Lee, M. S., Young, H. S., Choi, J. S., and Jung, W. T., Phytochemical study for botanical utilization of the fruits of Malus baccata.Korean Journal of Pharmacognosy, 24, 282–288 (1993).

  8. Park, H. J., Kwon, S. H., Lee, J. H., Lee, K. H., Miyamoto, K., and Lee, K. T., Kalopanaxsaponin A is a basic saponin structure for the anti-tumor activity of hederagenin monodesmosides.Planta Medica, 67, 118–121 (2001).

  9. Safir, O., Fkih-Tetounai, S., De Tommasi, N., and Aquino, R. Saponins fromZygophylum gaetulum. Journal of Natual Products. 61, 130–4 (1998).

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Author information

Correspondence to Leon Azefack Tapondjou or David Lontsi or Beiham Luc Sondengam or Muhammad Iqbal Choudhary or Hee-Juhn Park or Jongwon Choi or Kyung-Tae Lee.

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Tapondjou, L.A., Lontsi, D., Sondengam, B.L. et al. Structure-activity relationship of triterpenoids isolated fromMitragyna stipulosa on cytotoxicity. Arch Pharm Res 25, 270–274 (2002). https://doi.org/10.1007/BF02976624

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Key words

  • Mitragyna stipulosa
  • Triterpenoid
  • Ursane-type
  • Cytotoxicity
  • Structure-activity relationship