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http://dx.doi.org/10.4062/biomolther.2012.100

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

Kim, Ji Ho (Daewoong Co., Ltd.)
Son, Yeon Kyung (Daewoong Co., Ltd.)
Kim, Gun Hee (Plant Resources Research Institute, Duksung Women's University)
Hwang, Keum Hee (Plant Resources Research Institute, Duksung Women's University)
Publication Information
Biomolecules & Therapeutics / v.21, no.3, 2013 , pp. 234-240 More about this Journal
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
Angelica keiskei Koidzumi; Monoamine oxidase inhibitor; Dopamine ${\beta}$-hydroxylase inhibitor; Xanthoangelol; 4-hydroxyderricin; Cynaroside;
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1 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.   DOI   ScienceOn
2 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.   DOI
3 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.   DOI   ScienceOn
4 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.   DOI   ScienceOn
5 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.   DOI   ScienceOn
6 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.
7 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.   과학기술학회마을
8 Quitkin, F., Rifkin, A. and Klein, D. F. (1979) Monoamine oxidase inhibitors: a review of antidepressant effectiveness. Arch. Gen. Psychiatry 36, 749-760.   DOI   ScienceOn
9 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.
10 Rigal, F. and Zarifi an, E. (1983) MAO inhibitors in psychiatric therapy: effects and side effects. Mod. Probl. Pharmacopsychiatry 19, 162-169.
11 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.   DOI
12 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.
13 Wimbiscus, M., Kostenko, O. and Malone, D. (2010) MAO inhibitors: Risks, benefi ts, and lore. Cleve. Clin. J. Med. 77, 859-882.   DOI   ScienceOn
14 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.   DOI   ScienceOn
15 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.   DOI   ScienceOn
16 Baba, K., Nakata, K., Taniguchi, M., Kido, T. and Kozawa, M. (1990) Chalcones from Angelica keiskei. Phytochemistry 29, 3907-3910.   DOI   ScienceOn
17 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.
18 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.
19 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.   과학기술학회마을
20 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.   DOI   ScienceOn
21 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.   DOI   ScienceOn
22 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.   DOI   ScienceOn
23 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.   DOI