DOI QR코드

DOI QR Code

Xanthoangelol and 4-Hydroxyderricin Are the Major Active Principles of the Inhibitory Activities against Monoamine Oxidases on Angelica keiskei K

  • Received : 2012.12.20
  • Accepted : 2013.03.20
  • Published : 2013.05.31

Abstract

Monoamine oxidase inhibitors (MAOI) have been widely used as antidepressants. Recently, there has been renewed interest in MAO inhibitors. The activity-guided fractionation of extracts from Angelica keiskei Koidzumi (A. keiskei K.) led to the isolation of two prenylated chalcones, xanthoangelol and 4-hydroxyderricin and a flavonoid, cynaroside. These three isolated compounds are the major active ingredients of A. keiskei K. to inhibit the MAOs and DBH activities. Xanthoangelol is a nonselective MAO inhibitor, and a potent dopamine ${\beta}$-hydroxylase (DBH) inhibitor. $IC_{50}$ values of xanthoangelol to MAO-A and MAO-B were calculated to be 43.4 ${\mu}M$, and 43.9 ${\mu}M$. These values were very similar to iproniazid, which is a nonselective MAO inhibitor used as a drug against depression. The $IC_{50}$ values of iproniazid were 37 ${\mu}M$, and 42.5 ${\mu}M$ in our parallel examination. Moreover, $IC_{50}$ value of xanthoangelol to DBH was calculated 0.52 ${\mu}M$. 4-Hydroxyderricin is a potent selective MAO-B inhibitor and also mildly inhibits DBH activity. The $IC_{50}$ value of 4-hydroxyderricin to MAO-B was calculated to be 3.43 ${\mu}M$ and this value was higher than that of deprenyl (0.046 ${\mu}M$) used as a positive control for selective MAO-B inhibitor in our test. Cynaroside is a most potent DBH inhibitor. The $IC_{50}$ value of cynaroside to DBH was calculated at 0.0410 ${\mu}M$. Results of this study suggest that the two prenylated chalcones, xanthoangelol and 4-hydroxyderricin isolated from A. keiskei K., are expected for potent candidates for development of combined antidepressant drug. A. keiskei K. will be an excellent new bio-functional food material that has the combined antidepressant effect.

Keywords

References

  1. Akihisa, T., Tokuda, H., Hasegawa, D., Ukiya, M., Kimura, Y., Enjo, F., Suzuki, T. and Nishino, H. (2003) Chalcones, coumarins, and fl avanones from the exudate of Angelica keiskei and their chemopreventive effects. Cancer Lett. 201, 133-137. https://doi.org/10.1016/S0304-3835(03)00466-X
  2. Baba, K., Nakata, K., Taniguchi, M., Kido, T. and Kozawa, M. (1990) Chalcones from Angelica keiskei. Phytochemistry 29, 3907-3910. https://doi.org/10.1016/0031-9422(90)85357-L
  3. Birkmayer, W., Knoll, J., Riederer, P. and Youdim, M. (1983) (-)-Deprenyl leads to prolongation of L-dopa effi cacy in Parkinson's disease. Mod. Probl. Pharmacopsychiatry 19, 170-176.
  4. Fujita, T., Sakuma, S., Sumiya, T., Nishida, H., Fujimoto, Y., Baba, K. and Kozawa, M. (1992) The effects of xanthoangelol E on arachidonic acid metabolism in the gastric antral mucosa and platelet of the rabbit. Res. Comun. Chem. Pathol. Pharmacol. 77, 227-240.
  5. Han, Y. N., Choo, Y. S., Lee, Y. C., Moon, Y. I., Kim, S. D. and Choi, J. W. (2001) Monoamine oxidase B inhibitors from the fruits of Opuntia fi cus-indica var. saboten. Arch. Pharm. Res. 24, 51-54. https://doi.org/10.1007/BF02976493
  6. Kim, O. K., Kung, S. S., Park, W. B., Lee, M. W. and Ham, S. S. (1992) The nutritional components of aerial whole plant and juice of Angelica keiskei. Korean J. Food Sci. Technol. 25, 592-596.
  7. Kim, J. H., Kim, G. H. and Hwang K. H. (2012) Monoamine oxadase and dopamine $\beta$-hydroxylase inhibitors from the fruits of gardenia jasminoides. Biomol. Ther. 20, 214-219. https://doi.org/10.4062/biomolther.2012.20.2.214
  8. Kitaichi, Y., Inoue, T., Nakagawa, S., Boku, S., Izumi, T. and Koyama, T. (2010) Combined treatment with MAO-A inhibitor increases extracellular noradrenaline levels more than MAO-A inhibitor alone through increases in $\beta$-phenylethylamine. Euro. J. Pharmacol. 637, 77-82. https://doi.org/10.1016/j.ejphar.2010.04.014
  9. Larsen, J. K., Gjerris, A. P., Anderson. J., Bille, A., Christensen, E. M., Hoyer, E., Hensen, H., Mejlhede, A., Langagergaard, A., Laursen, A. L., Nilkantan, B., Olafsson, K., Severin, B. and Rafaelsen, O. J. (1991) Moclobemide in depression: a randomized, multicentre trial against isocarboxazide and clomipramine emphasing atypical depression. Acta Psychiatr. Scand. 84, 564-570. https://doi.org/10.1111/j.1600-0447.1991.tb03196.x
  10. Lipper, S., Murphy, D. L., Slater, S. and Buchsbaum, M. S. (1979) Comparative behavioral effects of clorgyline and pargyline in man: a preliminart evaluation. Psychopharmacol. (Berl) 62, 123-128. https://doi.org/10.1007/BF00427124
  11. Lotufo-Neto, F., Trivedi, M. and Thase, M. E. (1999) Meta-analysis of the reversible inhibitors of monoamine oxidase type A moclobemide and brofarnmine for the treatment of depression. Neuropsychopharmacology 20, 226-247. https://doi.org/10.1016/S0893-133X(98)00075-X
  12. Mann, J. J., Aarons. S. F., Wilner, P. J., Keilp, J. G., Sweeney, J. A., Pearlstein, T., Frances, A. J., Kocsis, J. H. and Brown, R. P. (1989) A controlled study of the antidepressant effi cacy and side effects of (-) deprenyl. A selective monoamine oxidase inhibitor. Arch. Gen. Psychiatry 46, 45-50. https://doi.org/10.1001/archpsyc.1989.01810010047007
  13. Meyer, J. H., Wilson, A. A., Sagrati, S., Miler, L., Rusjan, P., Bloomfi eld, P. M., Clark, M., Sacher, J., Voineskos, A. N. and Houle, S. (2009) Brain monoamine oxidase a binding in major depressive disorder: relationship to selective serotonin reuptake inhibitor treatment, recovery, and recurrence. Arch. Gen. Psychiatry 66, 1304-1312. https://doi.org/10.1001/archgenpsychiatry.2009.156
  14. Ogawa, H., Ohno, M. and Baba, K. (2005) Hypotensive and lipidregulatory actions of 4-hydroxyderricin, a chalcone from Angelca keiskea, in stroke-prone spontaneously hypertensive rats. Clin. Exp. Pharmacol. Physiol. 32, 19-23. https://doi.org/10.1111/j.1440-1681.2005.04147.x
  15. Okuyama, T., Takata, M., Takayasu, J., Hasegawa, T., Tokuda, H., Nishino, A., Nishino, H. and Iwahima, A. (1991) Anti-tumor-promotion by principles obtained from Angelica keiskei. Planta Med. 57, 242-246. https://doi.org/10.1055/s-2006-960082
  16. Park, J. C., Cho, Y. S., Park, S. K., Park, J. R., Chun, S. S., Ok, K. D. and Choi, J. W. (1995) Isolation of fl avone-7-O-glycosides from the aerial parts of Anglica keiskei and anti-hyperlipidmic effect. Korean J. Pharmacogn. 26, 337-343.
  17. Park, J. R., Park, S. K., Cho, Y. S., Chun, S. S., Choi, S. H. and Park J. C. (1997) Effects of Angelica keiskei on lipid metabolism in rats. J. Korean Soc. Food Sci. Nutr. 26, 308-313.
  18. Quitkin, F., Rifkin, A. and Klein, D. F. (1979) Monoamine oxidase inhibitors: a review of antidepressant effectiveness. Arch. Gen. Psychiatry 36, 749-760. https://doi.org/10.1001/archpsyc.1979.01780070027003
  19. Riederer, P., Reynolds, G. P., Jellinger, K., Seemann, D. and Danielczyk, W. (1983). Tranylcypromine isomers in Parkinson's disease: effect of low doses on monoamine oxidase inhibition and blood pressure response. Mod. Probl. Pharmacopsychiatry 19, 154-161.
  20. Rigal, F. and Zarifi an, E. (1983) MAO inhibitors in psychiatric therapy: effects and side effects. Mod. Probl. Pharmacopsychiatry 19, 162-169.
  21. Shimizu, E., Hayashi, A., Takahashi, R., Aoyagi, Y., Murakami, T. and Kimoto, K. (1999) Effects of angiotensin I-converting enzyme inhibitor from Ashitaba (Angelica keiskei) on blood pressure of spontaneously hypertensive rats. J. Nutr. Sci. Vitaminol. 45, 375-383. https://doi.org/10.3177/jnsv.45.375
  22. Stern, G. M., Lees, A. J., Hardie, R. and Sandler, M. (1983) Clinical and pharmacological aspects of (-)-deprenyl treatment in Parkinson's disease. Acta Neurol. Scand. Suppl. 95, 113-116.
  23. Wimbiscus, M., Kostenko, O. and Malone, D. (2010) MAO inhibitors: Risks, benefi ts, and lore. Cleve. Clin. J. Med. 77, 859-882. https://doi.org/10.3949/ccjm.77a.09103

Cited by

  1. Angelica keiskei, an emerging medicinal herb with various bioactive constituents and biological activities vol.40, pp.6, 2017, https://doi.org/10.1007/s12272-017-0892-3
  2. Angelica keiskeiKoidzumi Extracts Improve Some Markers of Liver Function in Habitual Alcohol Drinkers: A Randomized Double-Blind Clinical Trial vol.18, pp.2, 2015, https://doi.org/10.1089/jmf.2014.3222
  3. Quercetin and Related Chromenone Derivatives as Monoamine Oxidase Inhibitors: Targeting Neurological and Mental Disorders vol.24, pp.3, 2019, https://doi.org/10.3390/molecules24030418
  4. Design, Synthesis and Docking Calculations of Prenylated Chalcones as Selective Monoamine Oxidase B Inhibitors with Antioxidant Activity vol.4, pp.26, 2019, https://doi.org/10.1002/slct.201901282
  5. 4-Hydroxyderricin Isolated from the Sap of Angelica keiskei Koidzumi: Evaluation of Its Inhibitory Activity towards Dipeptidyl Peptidase-IV vol.87, pp.4, 2013, https://doi.org/10.3390/scipharm87040030
  6. Monoamine Oxidase (MAO) as a Potential Target for Anticancer Drug Design and Development vol.26, pp.19, 2021, https://doi.org/10.3390/molecules26196019