Butyrylcholinesterase Inhibitory Guaianolides from Amberboa ramosa

  • Khan Sher Bahadar (International Centre for Chemical Sciences, H.E.J. Research Institute of Chemistry, University of Karachi) ;
  • Haq Azhar-ul (International Centre for Chemical Sciences, H.E.J. Research Institute of Chemistry, University of Karachi) ;
  • Perveen Shagufta (International Centre for Chemical Sciences, H.E.J. Research Institute of Chemistry, University of Karachi) ;
  • Afza Nighat (Pharmaceutical Research Centre, PCSIR Labs Complex Karachi) ;
  • Malik Abdul (International Centre for Chemical Sciences, H.E.J. Research Institute of Chemistry, University of Karachi) ;
  • Nawaz Sarfraz Ahmad (International Centre for Chemical Sciences, H.E.J. Research Institute of Chemistry, University of Karachi) ;
  • Shah Muhammad Raza (International Centre for Chemical Sciences, H.E.J. Research Institute of Chemistry, University of Karachi) ;
  • Choudhary Muhammad lqbal (International Centre for Chemical Sciences, H.E.J. Research Institute of Chemistry, University of Karachi)
  • Published : 2005.02.01

Abstract

Phytochemical investigation of the whole plant of Amberboa ramosa led to the isolation of six sesquiterpene lactones which could be identified as $8{\alpha}$-hydroxy-$11{\beta}$-methyl-$1{\alpha}H,\;5{\alpha}H,\;6{\beta}H,\;7{\alpha}H,\;11{\alpha}H-guai-10(14)$, 4(15)-dien-6, 12-olide(2), $3{\beta},\;8{\alpha}-dihydroxy-11{\alpha}-methyl-1{\alpha}H,\;5{\alpha}H,\;6{\beta}H,\;7{\alpha}H,\;11{\beta}H-guai-10(14)$, 4(15)-dien-6, 12-olide (2), $3{\beta},\;4{\alpha},\;8{\alpha}-trihydroxy-4{\beta}(hydroxymethyl)-1{\alpha}H,\;5{\alpha}H,\;6{\beta}H,\;7{\alpha}H-guai-10(14)$, 11(13)-dien-6, 12-olide (3), $3{\beta},\;4{\alpha},\;8{\alpha}-trihydroxy-4{\beta}-(chloromethyl)-1{\alpha}H,\;5{\alpha}H,\;6{\beta}H,\;7{\alpha}H-guai-10(14)$, 11(13)-dien-6, 12-olide(4), $3{\beta},\;4{\alpha},\;dihydroxy-4{\beta}-(hydroxymethyl)-1{\alpha}H,\;5{\alpha}H,\;6{\beta}H,\;7{\alpha}H-guai-10(14)$, 11(13)-dien-6, 12-olide(5), $3{\beta},\;4{\alpha}-dihydroxy-4{\beta}-(chloromethyl)-8{\alpha}-(4-hydroxymethacrylate)-1{\alpha}H,\;5{\alpha}H,\;6{\beta}H,\;7{\alpha}H-guai-10(14)$, 11(13)-dien-6, 12-olide (6) by spectroscopic methods. All of them showed inhibitory potential against butyrylcholinesterase.

Keywords

References

  1. Akhtar, N., Malik, A., Afza, N., and Badar, Y., Cycloartane type triterpenes from Amberboa ramosa. J. Nat. Prod., 56, 295-299 (1993) https://doi.org/10.1021/np50092a019
  2. Ellman, G. L., Courtney K. D., Andres, V., and Featherstone, R. M., A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol., 7, 88-95 (1961) https://doi.org/10.1016/0006-2952(61)90145-9
  3. Fernandez, I., Garcia, B., Grancha, F. J., and Pedro, J. R., Sesquiterpenes lactones, flavonoids and coumarins from Centaurea collina. 28, 2405-2407 (1989) https://doi.org/10.1016/S0031-9422(00)97993-7
  4. Harrison, D. A. and Kulshrestha, D. K., Chemical constituents of Amberboa ramosa. Fitoterapia, LV, 189-192 (1984)
  5. Meyer, B. N., Ferrigni, N. R., Putnam, J. E., Jacobsen, L. B., Nichols, D. E., and McLaughlin, J. L., Brine shrimp: A convential general bioassay for active plant constituents. Planta Med., 45, 31-34 (1982) https://doi.org/10.1055/s-2007-971236
  6. Huikang, W., Zhangdia, l., Kan, H., and Shuwen, W., Studies on the chemical constituents of Saussurea involucrate. Yaoxue Xuebao, 21, 680-682 (1986)
  7. Oksuz, S., Serin, S., and Topcu, G., Sesquiterpene lactones from Centaurea hermanii. Phytochemistry, 35, 435-438 (1994) https://doi.org/10.1016/S0031-9422(00)94776-9
  8. Schwarz, M., Glick, D., Loewensten, Y., and Soreq, H., Engineering of human cholinesterases explains and predicts diverse consequences of administration of various drugs and poisons. Pharmacol. Ther., 67, 283-322 (1995) https://doi.org/10.1016/0163-7258(95)00019-D
  9. Silver A., The Biology of Cholinesterases. North Holland Publishing Comp., Amsterdam Elsevier (1974)
  10. Singh, P. and Bhala, M., Guaianolides from Saussurea candicans. Phytochemistry, 27, 1203-1205 (1988) https://doi.org/10.1016/0031-9422(88)80305-4
  11. Singhal, A. K., Chowdhury, P. K., Sharma, R. P., Baruah, J. N., and Herz, W., Guainolides from Tricholepis glaberrima. Phytochemistry, 21, 462-463 (1982) https://doi.org/10.1016/S0031-9422(00)95292-0
  12. Youssef, D. and Frahm, A. W., Constituents of the Egyptian Centaurea scoparia; chlorinated guainolides of the aerial part. Planta Med., 60, 267-270 (1994) https://doi.org/10.1055/s-2006-959473
  13. Yu, S. Q., Holloway, H. W., Utsuki, T., Brossi, A., and Greig, N. H., Synthesis of novel phenserinebasedselective inhibitors of butyrylcholinesterase for Alzheimers disease. J. Med. Chem., 42, 1855-1861 (1999) https://doi.org/10.1021/jm980459s