Abstract
For the evaluation of the role of substituents ofar-turmerone for its anticancer activity, ar-turmerone (1a) and its analogs like 2-methyl-6-(4′-methyphenyl)-2-octen-4-one (1b), 2-methyl-6-phenyl-2-hepten-4-one (1c), 2-methyl-6-phenyl-2-octen-4-one, (1d), and 2-methyl-6-(trans-4′-methylcyclohexyl)-2-hepten-4-one (1e) were prepared and their cytotoxic activities against L1210 cell were determined. Omission of methyl group atpara-position dose not variate the cytotoxicity of ar-turmerone. Elongation of alkyl group at 6-position decreases ED50 value. Saturation of aromatic ring of ar-turmerone markedly decreases the cytotoxicity. Therefore the smaller size of alkyl group at 6-position and aromatic ring of ar-turmerone should be essential for exhibiting its anticancer activity.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature Cited
Matthes, H.W.D., Luu, B. and Ourisson, G.: Cytotoxic components ofZingiber zerumbet, Curcuma zedoaria, andCurcuma domestica, Phytochemistry,19, 2643 (1980).
Itokawa, H. Hirayamo, F., Funakoshi, K. and Takeya, K.: Studies on the antitumor bisabolane sesquiterpenoids isolated fromCurcuma xanthorriza.Chem. Pharm. Bull.,33, 3488 (1985).
Rupe, V. K. and Wiederkehr. F.: Zur kennites des ar-trumerone aus dem cucuma-ol,Helv. Chim. Acta,7, 654 (1924). (b) Honwad, V. K. and Rao, A. S.: Absolute configuration of ar-turmer-one,Tetrahedron,20 2921 (1964).
Lee, J. H., Kang, S. K. and Ahn, B. Z.: Antineoplastic natural productsl and the analogues (XI)-Cytotoxic activity against L1210 cell of some raw drugs from the oriental medicine and falk-lore,Korean J. Pharmacognosy,17, 286 (1986), (b) Ahn, B. Z. and Lee, J. H.: Cytotoxic and Cytotoxicity-potentiating effects of the curcuma root on L1210 cell,Korean J. Pharmacognosy,20, 223 (1989).
Perrin, D. D. and Armarego, W. L. F.:Purification of Laboratory Chemicals, 3rd Edition, Pergamon, Oxford, 1988.
Ghandi, R. D., Vig, O. P., Mukherhji, S. M.: A novel unambiguous synthesis of dl-ar-turmer-one.Tetrahedron,7, 236 (1959). (b) Heathcock, H. C.:The total synthesis of natural products vol. 2-the total synthesis of sesquiterpenes, ed. by A. P. ApSimon, John Wiley & Sons, New York, 247–251 (1973), references therein. (c) Meyers, A. I. and Smith, R. K.: A total synthesis of (+)-ar-turmerone,Tetrahedron Letters, 2749 (1979). (d) Sato, T., Kawara, T., Nishizawa, A., and Fujitawa, T.: A novel synthetic method for optically active terpenes by the ring-opening reaction of R-(+)-β-methyl-β-propiolactione,Tetrahedron Letters,21, 3377 (1980). (e) Rousseau, G. and Blanco, L.: Reaction of silylketene acetals with 3.3-dimethylacryloyl chloride,Tetrahedron Letters,26, 4195 (1985).
Eliel, E. L., Hutchins, R. O. and Knoeber, S. M.:Org. Synth. Coll., Vol. 6, 442 (1988).
Kpracho, A. P. Weimaster, J. F., Eldridge, J. M., Jahngen, E. G. M., Lovey, A. J. and Stephens, W. P.: Synthetic applications and mechanism studies on the decarboxylation of geminal diesters and related system effected in dimethysulfoxide by water and/or by water with added salts.J. Org. Chem.,43, 138 (1978).
Thayer, P. S., Himmerlfarb, P. and Watts, G. L.: Cytotoxicity assay with L1210 cellin vitro. Comparison with L1210 in vitro, and KB cellsin vitro.Cancer Chem. Rep.,2, 1 (1971).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Oh, WG., Baik, KU., Jung, SH. et al. The role of substituents ofar-turmerone for its anticancer activity. Arch. Pharm. Res. 15, 256–262 (1992). https://doi.org/10.1007/BF02974066
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02974066