Monoamine Oxidase Inhibitory Flavonoids from the Root Bark of Cudrania tricuspidata

  • Han, Xiang-Hua (College of Pharmacy, Chungbuk National University) ;
  • Hwang, Ji-Hye (College of Pharmacy, Chungbuk National University) ;
  • Hong, Seong-Su (College of Pharmacy, Chungbuk National University) ;
  • Choe, Sang-Gil (College of Pharmacy, Chungbuk National University) ;
  • Lee, Chul (College of Pharmacy, Chungbuk National University) ;
  • Lee, Moon-Soon (College of Agriculture, Life & Environmental Sciences, Chungbuk National University) ;
  • Lee, Dong-Ho (School of Life Sciences and Biotechnology, Korea University) ;
  • Lee, Myung-Koo (College of Pharmacy, Chungbuk National University) ;
  • Lee, Mi-Kyeong (College of Pharmacy, Chungbuk National University) ;
  • Hwang, Bang-Yeon (College of Pharmacy, Chungbuk National University)
  • 투고 : 2010.05.10
  • 심사 : 2010.06.16
  • 발행 : 2010.06.30

초록

Two new benzylated flavonoids, 5,7,4'-trihydroxy-6-p-hydroxybenzylflavanone (1) and 5,7,4'-trihydroxy-6,8-di-p-hydroxybenzylflavanone (2) together with six known flavonoids, kaempferol (3), artocarpesin (4), cycloartocarpesin (5), cudraflavone D (6), gericudranin E (7), and leachianone G (8) have been isolated from the root bark of Cudrania tricuspidata. The structures of 1 and 2 were characterized based on spectroscopic data including 1D- and 2D-NMR. All the isolates were evaluated for their inhibitory effects of monoamine oxidase (MAO). Among them, kaempferol (3), artocarpesin (4), and cudraflavone D (6) showed moderate inhibitory effects with $IC_{50}$ values of 82.3, 30.8, and $71.8\;{\mu}M$, respectively.

키워드

참고문헌

  1. Edmondson, D.E., Binda, C., Wang, J., Upadhyay, A.K., and Mattevi, A., Molecular and mechanistic properties of the membrane-bound mitochondrial monoamine oxidases. Biochemistry, 26, 4220-4230 (2009).
  2. Fujimoto, T. and Nomura, T., Components of root bark of Cudrania tricuspidata 3. Isolation and structures studies on the flavonoids. Planta Med., 51, 190-193 (1985). https://doi.org/10.1055/s-2007-969453
  3. Fujimoto, T., Hano, Y., and Nomura, T., Components of root bark of Cudrania tricuspidata 1. Structures of four new isoprenylated xanthones, Cudraxanthones A, B, C and D. Planta Med., 50, 218-221 (1984a). https://doi.org/10.1055/s-2007-969682
  4. Fujimoto, T., Hano, Y., Nomura, T., and Uzawa., Components of root bark of Cudrania tricuspidata 2. Structures of two new isoprenylated flavones, Cudraflavones A and B. Planta Med., 50, 161-163 (1984b). https://doi.org/10.1055/s-2007-969660
  5. Han, X.H., Hong, S.S., Hwang, J.S., Jeong, S.H., Hwang, J.H., Lee, M.H., Lee, M.K., Lee, D., Ro, J.S., and Hwang, B.Y., Monoamine oxidase inhibitory constituents from the fruits of Cudrania tricuspidata. Arch. Pharm. Res., 28, 1324-1327 (2005). https://doi.org/10.1007/BF02977895
  6. Hano, Y., Matsumoto, Y., Shinohara, K., Sun, J.Y., and Nomura, T., Structures of four new isoprenylated xanthones, Cudraxanthones L, M, N, and O from Cudrania tricuspidata. Planta Med., 57, 172-175 (1991). https://doi.org/10.1055/s-2006-960059
  7. Hano, Y., Matsumoto, Y., Shinohara, K., Sun, J.Y., and Nomura, T., Cudraflavones C and D, Two new prenylflavones from the root bark of Cudrania tricuspidata. Heterocycles, 31, 1339-1344 (1990). https://doi.org/10.3987/COM-90-5416
  8. Hwang, J.H., Hong, S.S., Han, X.H., Hwang, J.S., Lee, D., Lee, H., Yun, Y.P., Kim, Y., Ro, J.S., and Hwang, B.Y., Prenylated xanthones from the root bark of Cudrania tricuspidata. J. Nat. Prod., 70, 1207-1209 (2007). https://doi.org/10.1021/np070059k
  9. Iinuma, M., Ohyama, M., Tanaka, T., and Lang, F.A., Three new phenolic compounds from the roots of Sophora leachiana. J. Nat. Prod., 56, 2212-2215 (1993). https://doi.org/10.1021/np50102a033
  10. Jung, B.S. and Shin, M.K., Encyclopedia of illustrated Korean natural drugs. Young Lim Sa, Seoul, pp. 544-545 (1990).
  11. Kim, J.E., Jung, M.J., Jung, H.A., Woo, J.J., Cheigh, H.S., Chung, H.Y., and Choi, J.S. A new kaempferol 7-O-triglucoside from the leaves of Brassica juncea L. Arch. Pharm. Res., 25, 621-624 (2002). https://doi.org/10.1007/BF02976932
  12. Kraml, M., A rapid microfluorimetric determination of monoamine oxidase. Biochem. Pharmacol., 14, 1684-1686 (1965). https://doi.org/10.1016/0006-2952(65)90025-0
  13. Lee, B.W., Gal, S.W., Park, K.M., and Park, K.H., Cytotoxic xanthones from Cudrania tricuspidata. J. Nat. Prod., 68, 456-458 (2005). https://doi.org/10.1021/np030481a
  14. Lee, I.K., Kim, C.J., Song, K.S., Kim, H.M., Koshino, H., Uramoto, M., and Yoo, I.D., Cytotoxic benzyl dihydroflavonols from Cudrania tricuspidata. Phytochemistry, 41, 213-216 (1996). https://doi.org/10.1016/0031-9422(95)00609-5
  15. Lee, I.K., Kim, C.J., Song, K.S., Kim, H.M., Yoo, I.D., Koshino, H., Esumi, Y., and Uramoto, M. Two benzylated dihydroflavonols from Cudrania tricuspidata. J. Nat. Prod., 58, 1614-1617 (1995). https://doi.org/10.1021/np50124a024
  16. Lee, Y.J., Kim, S., Lee, S.J., Ham, I., and Whang, W.K., Antioxidant activities of new flavonoids from Cudrania tricuspidata root bark. Arch. Pharm. Res., 32, 195-200 (2009). https://doi.org/10.1007/s12272-009-1135-z
  17. Naoi, M., and Nagatsu, T., Quinoline and quininaldines as naturally occurring inhibitors specific for type A monoamine oxidase. Life Sci., 40, 1075-1082 (1987). https://doi.org/10.1016/0024-3205(87)90570-4
  18. Park, K.H., Park, Y.D., Han, J.M., Im, K.R., Lee, B.W., Jeong, I.Y., Jeong, T.S., and Lee, W.S., Anti-atherosclerotic and anti-inflammatory activities of catecholic xanthones and flavonoids isolated from Cudrania tricuspidata. Bioorg. Med. Chem. Lett., 16, 5580-5583(2006). https://doi.org/10.1016/j.bmcl.2006.08.032
  19. Ro, J.S., Lee, S.S., Lee, K.S., and Lee, M.K., Inhibition of type A monoamine oxidase by coptisine in mouse brain. Life Sci., 70, 639- 645 (2001). https://doi.org/10.1016/S0024-3205(01)01437-0
  20. Seo, E.J., Curtis-Long, M.J., Lee, B.W., Kim, H.Y., Ryu, Y.B., Jeong, T.S., Lee, W.S., and Park, K.H., Xanthones from Cudrania tricuspidata displaying potent a-glucosidase inhibition. Bioorg. Med. Chem. Lett., 17, 6421-6424 (2007). https://doi.org/10.1016/j.bmcl.2007.10.007
  21. Shih, J.C., Chen, K., and Ridd, M.J., Monoamine oxidase: from genes to behaviour. Annu. Rev. Neurosci., 22, 197-217 (1999). https://doi.org/10.1146/annurev.neuro.22.1.197
  22. Takashima, J., and Ohsaki, A. Brosimacutins A-I, nine new flavonoids from Brosimum acutifolium. J. Nat. Prod., 65, 1843-1847 (2002). https://doi.org/10.1021/np020241f
  23. Tian, Y.H., Kim, H.C., Cui, J.M., and Kim, Y.C., Hepatoprotective constituents of Cudrania tricuspidata. Arch. Pharm. Res., 28, 44-48 (2005). https://doi.org/10.1007/BF02975134
  24. Yamada, M. and Yasuhara, H., Clinical pharmacology of MAO inhibitors: Safety and future. Nerurotoxicology, 25, 215-221 (2004). https://doi.org/10.1016/S0161-813X(03)00097-4
  25. Youdim, M.B., Edmondson, D.E., and Tipton, K.F., The therapeutic potential of monoamine oxidase inhibitors. Nat. Rev. Neurosci., 7, 295-309 (2006). https://doi.org/10.1038/nrn1883
  26. Young, H.S., Park, J.H., Park, H.J., and Choi, J.S., Chemical study of the stem of Cudrania tricuspidata. Arch. Pharm. Res., 12, 39-41 (1989). https://doi.org/10.1007/BF02855744
  27. Zou, Y.S., Hou, A.J., and Zhu, G.F., Isoprenylated xanthones and flavonoids from Cudrania tricuspidata. Chem. Biodivers., 2, 131-138 (2005). https://doi.org/10.1002/cbdv.200490164
  28. Zou, Y.S., Hou, A.J., Zhu, G.F., Chen, Y.F., Sun, H.D., and Zhao, Q.S., Cytotoxic isoprenylated xanthones from Cudrania tricuspidata. Bioorg. Med. Chem., 12, 1947-1953 (2004). https://doi.org/10.1016/j.bmc.2004.01.030