Estrogenic Activity of Furanocoumarins Isolated from Angelica dahurica

  • Piao, Xiang-Lan (School of Pharmaceutical Sciences, Peking University) ;
  • Yoo, Hye-Hyun (Bioanalysis and Biotransformation Research Center, Korea Institute of Science and Technology) ;
  • Kim, Hyun-Young (Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University) ;
  • Kang, Tak-Lim (College of Oriental Medincine, Taejon University) ;
  • Hwang, Gwi-Seo (College of Oriental Medicine, Kyungwon University) ;
  • Park, Jeong-Hill (Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University)
  • Published : 2006.09.01

Abstract

In our efforts to discover novel phytoestrogens to treat menopausal symptoms, eleven furanocoumarins were isolated from Angelica dahurica and tested for their estrogenic activity on the Ishikawa cell line. Among the compounds tested, 9-hydroxy-4-methoxypsoralen and alloisoimperatorin showed strong abilities to induce alkaline phosphatase (AP) with $EC_{50}$ values of 1.1 and $0.8\;{\mu}g/mL$, respectively, whereas the other nine furanocoumarins were weakly or only slightly active.

Keywords

References

  1. Bennett, E. L. and Bonner, J., Isolation of Plant Growth Inhibitors from Thamnosma Montana. Amer. J. Botany, 40, 29-33 (1953) https://doi.org/10.2307/2438489
  2. Bergendorff, O., Dekermendjian, K., Nielsen, M., Shan, R., Witt, R., Ai, J., and Sterner, O., Furanocoumarins with affinity to brain benzodiazepine receptors in vitro. Phytochemistry, 44, 1121-1124 (1997) https://doi.org/10.1016/S0031-9422(96)00703-0
  3. Bolton, J. L., Pisha, E., Zhang, F., and Qiu, S., Role of quinoids in estrogen carcinogenesis. Chem. Res. Toxicol., 11, 1113- 1127 (1998) https://doi.org/10.1021/tx9801007
  4. Brosage, P., Hormone therapy: The woman's decision. Contemp. Nurse Pract., 1 (S), 3 (1995)
  5. Colditz, G. A., Hankinson, S. E., Hunter, D. J., Willett, W. C., Manson, J. E., Stampfer, M. J., Hennekens, C., Rosner, B., and Speizer, F. E., The use of estrogens and progestins and the risk of breast cancer in postmenopausal women. New Engl. J. Med., 332, 1589-1593 (1995) https://doi.org/10.1056/NEJM199506153322401
  6. Dreyer, D. L. and Lee A., Constituents of Cneoridium dumosum (Nutt.) Hook. F. Phytochemistry, 8, 1499-1501 (1969) https://doi.org/10.1016/S0031-9422(00)85920-8
  7. Edenharder, R., Speth, C., Decker, M., Kolodziej, H., Kayser, O., and Platt, K. L., Inhibition of mutagenesis of 2-amino-3- methylimidazo[4,5-f]quinoline (IQ) by coumarins and furanocoumarins, chromanones and furanochromanones. Mutat. Res., 345, 57-71 (1995) https://doi.org/10.1016/0165-1218(95)90070-5
  8. Grodstein, F., Stamfer, M. J., Colditz, G. A., Willett, W. C., Manson, J. E., Joffe, M., Rosner, B., Fuchs, C., Hankinson, S. E., Hunter, D. J., Hennekens, C. H., and Speizer, F. E., Postmenopausal hormone therapy and mortality. New Engl. J. Med., 336, 1769-1775 (1997) https://doi.org/10.1056/NEJM199706193362501
  9. Harris, R. B., Laws, A., Reddy, F. M., King, A., and Haskell, W. L., Are women using postmenopausal estrogens? A community survey. Am. J. Public Health, 80, 1266-1268 (1990) https://doi.org/10.2105/AJPH.80.10.1266
  10. Henderson, B. E., Ross, R., and Bernstein, L., Estrogen as a cause of human cancer. The Richard and Hinda Rosenthal Foundation Award Lecture. Cancer Res., 48, 246-253 (1988)
  11. Holinka, C. F., Hata, H., Kuramoto, H., and Gurpide, E., Effects of steroid hormones and antisteroids on alkaline phosphatase activity in human endometrial cancer cells (Ishikawa). Cancer Res., 46, 2771-2774 (1986)
  12. Hsu, H. -Y., Chen, Y. -P., Shen, S. -J., Hsu, C. -C., and Chang, H. -C., Oriental Materia Medica: A Concise Guide. Oriental Healing Arts Institute, (1986)
  13. Ishihara, K., Fukutake, M., Asano, T., Mizuhara, Y., Wakui, Y., Yanagisawa, T., Kamei, H., Ohmori, S., and Kitada, M., Simultaneous determination of byak-angelicin and oxypeucedanin hydrate in rat plasma by column-switching highperformance liquid chromatography with ultraviolet detection. J. of Chromatogra.B., 753, 309-314 (2001) https://doi.org/10.1016/S0378-4347(00)00569-7
  14. Kurzer, M. S. and Xu, X., Dietary phytoestrogens. Annu. Rev. Nutr., 17, 353-381 (1997) https://doi.org/10.1146/annurev.nutr.17.1.353
  15. Lee, S., Yoo, H. H., Piao, X. L., Kim, J. S., Kang, S. S., and Shin, K. H., Anti-estrogenic activity of lignans from Acanthopanax chiisanensis root. Arch. Pharm. Res., 28, 186-189 (2005) https://doi.org/10.1007/BF02977713
  16. Liehr, J. G., Genotoxic effects of estrogens. Mutat. Res., 238, 269-276 (1990) https://doi.org/10.1016/0165-1110(90)90018-7
  17. Murkies, A. L., Wilcox, G., and Davis, S. R., Clinical review 92: Phytoestrogens. J. Clin. Endocrinol. Metab., 83, 297-303 (1998) https://doi.org/10.1210/jc.83.2.297
  18. Nishida M., Kasahara K., Kaneko M., Iwasaki H., and Hayashi K., Establishment of a new human endometrial adenocarcinoma cell line, Ishikawa cells, containing estrogen and progesterone receptors. Nippon Sanka Fujinka Gakkai Zasshi, 37, 1103-1111 (1985)
  19. Perry, L. M., Medicinal Plants of East and Southeast Asia: Attributed Properties and Uses. The MIT Press, Cambridge, (1980)
  20. Piao, X. L., Baek, S. H., Park, M. K., and Park, J. H., Tyrosinaseinhibitory furanocoumarin from Angelica dahurica. Biol. Pharm. Bull., 27, 1144-1146 (2004) https://doi.org/10.1248/bpb.27.1144
  21. Pisha, E. and Pezzuto, J. M., Cell-based assay for the determination of estrogenic and anti-estrogenic activities. Methods Cell Sci., 19, 37-43 (1997) https://doi.org/10.1023/A:1009746605060
  22. Saiki, Y., Morinaga, K., Okegawa, O., Sakai, S., Amaya, Y., Ueno, A., and Fukushima, S., On the Coumarins of the Root Agelica dahurica Benth. et Hook. Yakugaku Zasshi, 53, 1313-1317 (1971)
  23. Setchell, K. D. R., Phytoestrogens: The biochemistry, physiology, and implications for human health of soy isoflavones. Am. J. Clin. Nutr., 68, 1333S-1346S (1998) https://doi.org/10.1093/ajcn/68.6.1333S
  24. Setchell, K. D. R. and Cassidy, A., Dietary isoflavones: Biological effects and relevance to human health. J. Nutr., 129, 758S-767S (1999) https://doi.org/10.1093/jn/129.3.758S
  25. Stampfer, M. J., Willett, W. C., Hunter, D. J., and Manson, J. E., Type of postmenopausal hormone use and risk of breast cancer: 12-year follow-up from the Nurses' Health Study. Cancer Causes Control, 3, 433-439 (1992) https://doi.org/10.1007/BF00051356
  26. Stanley, W. L. and Vannier, S. H., Psoralens and substituted coumarins from expressed oil of lime. Phytochemistry, 6, 585-596 (1967) https://doi.org/10.1016/S0031-9422(00)82921-0
  27. Tang, W. and Eisenbrand, G., Chinese Drugs of Plant Origin, Chemistry, Pharmacology, and Use in Traditional and Modern Medicine. Springer, Berlin, (1992)
  28. Wang, C. -C., Lai, J. -E., Chen, L. -G., Yen, K. -Y. and Yang, L. - L., Inducible nitric oxide synthase inhibitors of Chinese herbs. Part 2: Naturally occurring furanocoumarins. Bioorg. Med. Chem., 8, 2701-2707 (2000) https://doi.org/10.1016/S0968-0896(00)00200-5
  29. Wickelgren, I., Estrogen: A new weapon against Alzheimer's. Science, 276, 676-677 (1997) https://doi.org/10.1126/science.276.5313.676
  30. Yoo, H. H., Kim, T., Ahn, S., Kim, Y. J., Kim, H. Y., Piao, X. L., and Park, J. H., Evaluation of the estrogenic activity of leguminosae plants. Biol. Pharm. Bull., 28, 538-540 (2005) https://doi.org/10.1248/bpb.28.538