Cholinesterase Inhibitory Activity of Two Farnesylacetone Derivatives from the Brown Alga Sargassum sagamianum

  • Ryu, Geon-Seek (Regional Research Center, Hanbat National University) ;
  • Park, Soo-Hee (Department of Chemical Technology, Hanbat National University) ;
  • Kim, Eun-Sook (Department of Chemical Technology, Hanbat National University) ;
  • Choi, Byoung-Wook (Department of Chemical Technology, Hanbat National University) ;
  • Ryu, Shi-Yong (Korea Research Institute of Chemical Technology) ;
  • Lee, Bong-Ho (Department of Chemical Technology, Hanbat National University)
  • Published : 2003.10.01

Abstract

Two known farnesylacetone derivatives (1 and 2) were isolated from the Korean brown alga Sargassum sagamianum off Jeju Island, Korea. Compounds 1 and 2 were identified as (5E,10Z)-6, 10, 14-trimethylpentadeca-5, 10-dien-2, 12-dione and (5E,9E,13E)-6, 10,4-trimethylpentadeca-5,9,13-trien-2,12-dione, respectively, by comparison with the literature data. Compounds 1 and 2 showed moderate acetylcholinesterase and butyrylcholinesterase inhibitory activities with $IC_{50}$ values of 65.0∼48.0 and 34.0∼23.0 $\muM$, respectively.

Keywords

References

  1. Bates R. B., Gale D. M., and Gruner B. J., The stereoisomeric farnesol. J. Org. Chem., 28, 1086-1089 (1963) https://doi.org/10.1021/jo01039a054
  2. Bazelyansky M., Robey E., and Kirsch J. F., Fraction diffusion limited component of reactions catalyzed by acetylcholinesterase. Biochem., 25, 125-130 (1986) https://doi.org/10.1021/bi00349a019
  3. Berkman C. E., Quinn D. A., and Thompson C.M., International of acetylcholinesterase with the enantiomers of malaoxon and isomalathion. Chem. Res. Toxicol., 6, 724-730 (1993) https://doi.org/10.1021/tx00035a019
  4. Brzostowska M., He X., Greig N. H., Rapoport S. I., and Brossi A., Phenylcarbamates of (-)-eseroline, (-)-N1-noreseroline and (-)-physovenol: selective inhibitors of acetyl and, or butyrylcholinesterase. Med. Chem. Res., 2(4), 238-246 (1992)
  5. Ellman G. L., Courtney D. K., Andres, V., and Featherstone R. M., A new and rapid colotimetric determination of acetylcholinesterase activity. Biochem. Pharmacol., 7, 88-95 (1961) https://doi.org/10.1016/0006-2952(61)90145-9
  6. Gregson R. P., Kazlauskas R., Murphy P. T., and Wells R. J., New metabolites from the brown alga Cystophora torulosa. Aust. J. Chem., 30, 2527-2532 (1977) https://doi.org/10.1071/CH9772527
  7. Greig N. H., Utsuki T., Yu Q., Zhu X., Holloway H.W., Perry T., Lee B., Ingram D. K., and Lahiri D. K., Butyrylcholinesterase: a new therapeutic target in AD treatment? Alzheimer Insights, 7(2), 1-6 (2001a)
  8. Greig N. H., Utsuki T., Yu Q., Zhu X., Holloway H.W., Perry T., Lee B., Ingram D. K., and Lahiri D. K., A new therapeutic target in Alzheimers disease treatment: attention to butyroylcholinesterase. Curr. Med. Res. Opinion, 17(2), 1-6 (2001b) https://doi.org/10.1185/03007990152005397
  9. Greig N. H., Pei X. F., Soncrant T. T., Ingram D. K., and Brossi A., Phenserine and ring C hetero-analogs: Drug candidates for the treatment of Alzheimer's disease. Med. Res. Reviews, 15(1), 3-31 (1995c) https://doi.org/10.1002/med.2610150103
  10. Huegin, W., Potentiating action of tacrine on the effects of succinylcholine. Anaesthesist, 11, 338-340 (1962)
  11. Ibata, K., Mizuno, M., Takigawa, T., and Tanaka, Y., Long-chain betula prenol-type polyprenol from the Ginkgo biloba. Biochem. J., 213, 305-311 (1983) https://doi.org/10.1042/bj2130305
  12. Ishitsuka, M., Kusumi, T., Nomura, Y., Konno, T., and Kakisawa, H., New geranylgeranylbenzoquinone derivatives from Sargassum tortile. Chem. Lett., 1269-1272 (1979)
  13. Kazlauskas, R., King, L., Murphy, P. T., Warren, R. G., and Wells, R. J., New metabolites from the brown algal genus Cystophora. Aust . J. Chem., 34, 439-447 (1981) https://doi.org/10.1071/CH9810439
  14. Kikuchi, T., Yokoi, T., Nakazawa, S., Kuroda, H., Masada, Y., Kitamura, K., and Kuriyama, K., Structure and absolute configuration of sargatriol, a new isopreoid chromenol from a brown alga Sargassum tortile C. Agardh. Chem. Pharm. Bull., 31(1), 106-113 (1983) https://doi.org/10.1248/cpb.31.106
  15. Kusumi T., Ishitsuka M., Nomura Y., Konno T., and Kakisawa H., New farnesylacetone derivatives from Sargassum micracanthum. Chem. Lett., 1181-1184 (1979a)
  16. Kusumi, T., Shibata, Y., Ishitsuka, M., and Kinoshita, T., Structure of new plastoquinones from the brown alga Sargassum serratifolium. Chem. Lett., 277-278 (1979b)
  17. Kusumi, T., Ishitsuka, M., Nomura, Y., Konno, T., and Kakisawa, H., New farnesylacetone derivatives from Sargassum microcanthum. Chem. Lett., 1181-1184 (1979c)
  18. Liu, J. S., Zhu, Y. L., Yu, C. M., Zhou, Y. Z., Han, Y. Y., Wu, F. W., and Qi, B. F., The structures of huperzine A and B, two new alkaloids exhibiting marked anticholinesterase activity. Can. J. Chem., 64(4), 837-839 (1986) https://doi.org/10.1139/v86-137
  19. Lowry, O. H., Rosebrough, N. J., Farr, A. L., and Randall, R. J, Protein measurement wih the Folin phenol Reagent. J. Biol. Chem., 193, 265-275 (1951)
  20. Romani, R., Antognelli, C., Baldracchini, F., Santis, A. D, Isani, G., Giovannini E., and Rosi G., Increased acetylcholinesterase activities in specimens of Sparus auratus exposed to sublethal Copper concentrations. Chemico-Biological Interactions, 145(3), 321-329 (2003) https://doi.org/10.1016/S0009-2797(03)00058-9
  21. Ryu, G., Park, S. H., Kim, E. S., Choi, B. W., and Lee, B. H., Potent Butyrylcholinesterase (BuChE) Inhibitory Activity of Two Plastoquinone Derivatives from the Brown Alga Sargassum sagamianum (in preparation)
  22. Segawa, M. and Shirahama, H., New plastoquinones from the brown alga Sargassum sagamianum var. Yezoense. Chem. Lett., 1365-1366 (1987)
  23. Shizuri, Y., Matsukawa, S., Ojika, M., and Yamada, K., Two new farnesylacetone derivatives from the brown alga Sargassum micracathum. Phytochem., 21(7), 1808-1809 (1982) https://doi.org/10.1016/S0031-9422(82)85074-7
  24. Tanaka, Y., Sato, H., and Kageyu, A., Carbon-13 NMR analysis of polystyrene by means of model compounds. Polymer, 23, 1087-1090 (1982) https://doi.org/10.1016/0032-3861(82)90412-8
  25. Yu, Q. S., Holloway, H. W., Utsuki , T., Brossi, A., and Greig, N. H., Synthesis of Novel Phenserine-Based-Selective Inhibitors of Butyrylcholinesterase for Alzheimer's Disease. J. Med. Chem., 42(10), 1855-1861 (1999) https://doi.org/10.1021/jm980459s