Inhibitory Activity of IL-6 Production by Flavonoids and Phenolic Compounds from Geranium thunbergii

  • Published : 2008.03.31

Abstract

Three flavonoids (1 - 3) and three phenolic compounds (4 - 6) were isolated from the whole plant of Geranium thunbergii Sieb. et Zucc (Geraniaceae). Their structures were determined by chemical and spectral analysis. These compounds were examined for the inhibitory activity of IL-6 production in $TNF-{\alpha}$ stimulated MG-63 cell. Among the isolated compounds, gallic acid (4) and gallic acid methyl ester (6) showed potent inhibitory activity.

Keywords

References

  1. Agrawal, P.K., NMR spectroscopy in the structural elucidation of oligosaccharides and glycosides. Phytochemistry 31, 3307-3330 (1992) https://doi.org/10.1016/0031-9422(92)83678-R
  2. Bae, K.W., The medicinal plants of Korea. Kyo-Hak Publishing Co., Seoul, pp (2000)
  3. Cai, X.F., Shen, G., Dat, N.T., Kang, O.H., Kim, J.A., Lee, Y.M., Lee, K.J., and Kim, Y.H. Inhibitory effect of TNF-$\alpha$ and IL-8 secretion by pimarane-type diterpenoids from Acanthopanax koreanum. Chem. Pharm. Bull. 51, 605-607 (2003) https://doi.org/10.1248/cpb.51.605
  4. Chung, S.-K., Kim, Y.-C., Takaya, Y., Terashima, K., and Niwa, M., Novel flavonol glycoside, 7-O-methyl mearnsitrin, from Sageretia theezans and its antioxidant effect. J. Agric. Food. Chem. 52, 4664- 4668 (2004) https://doi.org/10.1021/jf049526j
  5. Farkas, L., Vermes, B., Nogradi, M., and Kalman, A., The final structure of robinin and biorobin and their total synthesis. Phytochemistry 15, 215-218 (1976) https://doi.org/10.1016/S0031-9422(00)89088-3
  6. Fossen, T., Larsen, A., Kiremire, B.T., and Andersen, M., Flavonoids from blue flowers of Nymphaea caerulea. Phytochemistry 51, 1133- 1137 (1999) https://doi.org/10.1016/S0031-9422(99)00049-7
  7. Hirano, T., Yasukawa, K., Harada, H., Taga, T., Watanabe, Y., Matsuda, T., Kashiwamura, S., Nakajima, K., Koyama, K., Iwamatsu, A., Tsunsawa, S., Sakiyama, F., Matsui, H., Takahara, Y., Taniguchi, T., and Kishimoto, T., Complementary DNA for a novel human interleukin (BSF-2) that induced lymphocytes to produce immunoglobulin. Nature 324, 73-76 (1986) https://doi.org/10.1038/324073a0
  8. Hirano, T., Akira, S., Taga, T., and Kishimoto, T., Biological and clinical aspects of interleukin 6. Immunol. Today 11, 443-449 (1990) https://doi.org/10.1016/0167-5699(90)90173-7
  9. Harbone, J.B., The flavonoids: advances in research since 1986. Champman & Hall, London, pp. 442-473 (1994)
  10. Ito, H., Hatano, T., Namba, O., Shirono, T., Okuda, T., and Yoshida, T., Constituents of Geranium thunbergii Sieb. Et Zucc. XV. Modified dehydroellagitannins, geraniinic acids B and C, and phyllanthusiin F. Chem. Pharm. Bull. 47, 1148-1151 (1999) https://doi.org/10.1248/cpb.47.1148
  11. Jung, H.A., Kim, J.E., Chung, H.Y., and Choi, J.S., Antioxidant principles of Nelumbo nucifera stamens. Arch. Pharm. Res. 26, 279-285 (2003) https://doi.org/10.1007/BF02976956
  12. Kang, S.S., Kim, J.S., Choi, S.Y., and Han, B.H., Phytochemical studies on Peoniae Radix. Kor. J. Pharmacogn. 24, 247-250 (1993)
  13. Kang, S.J., Hong, S.S., Hwang, B.Y., Ro, J.S., Lee, K.S., and Towers, G.H.N., Phenolic compounds from the stems of Sapium japonicum. Kor. J. Pharmacogn. 12, 125-128 (2006)
  14. Kim, B.H., Chung, E.Y., Ryu, J.-C., Jung, S.-H., Min, K.R., and Kim, Y., Anti-inflammatory mode of isoflavone glycosides sophoricoside by inhibition of interleukin-6 and cyclooxygenase-2 in inflammatory response. Arch. Pharm. Res. 26, 306-311 (2003) https://doi.org/10.1007/BF02976960
  15. Kim, Y.-K., Kim, Y.S., Choi, S.U., and Ryu, S.Y., Isolation of flavonol rhamnosides from Loranthus tanakae and cytotoxic effect of them on human tumor cell lines. Arch. Pharm. Res. 27, 44-47 (2004) https://doi.org/10.1007/BF02980044
  16. Lee, S.H., Kim, B.K., Cho, S.H., and Shin, K.H., Phytochemical constituents from the fruits of Acanthopanax sessiliflorus. Arch. Pharm. Res. 25, 280-284 (2002) https://doi.org/10.1007/BF02976626
  17. Liu, Q.H., Jeong, J.-E., Choi, E.J., Moon, Y.H., and Woo, E.-R. A new furofuran lignan from Geranium thunbergii. Arch. Pharm. Res. 29, 1109-1113 (2006) https://doi.org/10.1007/BF02969300
  18. Ly, T.N., Shimoyamada, M., and Yamauchi, R., Isolation and characterization of rosmarinic acid oligomers in Celastrus hindsii Benth leaves and their antioxidative activity. J. Agric. Food. Chem. 54, 3786-3793 (2006) https://doi.org/10.1021/jf052743f
  19. Markham, K.R., Techniques of flavonoid identification, Academic Press, London, New York, pp. 75-78 (1994)
  20. Nawar, M.A., Buddrus, J., and Bauer, H., Dimeric phenolic constituents from the roots of Tamarix nilotica. Phytochemistry 21, 1755-1758 (1982) https://doi.org/10.1016/S0031-9422(82)85054-1
  21. Okuda, T., Yoshida, T., Hatano, T., Ikeda, Y., Shingu, T., and Inoue, T., Constituents of Geranium thunbergii Sieb. Et Zucc. XIII. Isolation of water-soluble tannins by centrifugal partition chromatography, a biomimetic synthesis of elaeocarpusin. Chem. Pharm. Bull. 34, 4075- 4082 (1986) https://doi.org/10.1248/cpb.34.4075
  22. Park, W.Y., Lee, S.C., Ahn, B.T., and Lee, S.H., Phenolic compounds from Acalypha australis L. Kor. J. Pharmacogn. 24, 20-25 (1993)
  23. Pauli, G.F., Higher order and substituent chemical shift effects in the NMR glycosides. J. Nat. Prod. 63, 834-838 (2000) https://doi.org/10.1021/np990527t
  24. Peng, Z.F., Strack, D., Baumert, A., Subramaniam, R., Goh, N.K., Chia, T.F., Tan, S.N., and Chia, L.S., Antioxidant flavonoids from leaves of Polygonum hydropiper L. Phytochemistry 62, 219-228 (2003) https://doi.org/10.1016/S0031-9422(02)00504-6
  25. Rao, L.M., Yada, H., Ono, H., and Yoshida, M., Acylated and nonacylated flavonol monoglycosides from the indian minor spice Nagkesar (Mammea Iongifolia). J. Agric. Food. Chem. 50, 3143-3146 (2002) https://doi.org/10.1021/jf011461m
  26. Sawada, H., Miyakoshi M., Isoda, S., Ida, Y., and Shoh, J., Saponins from leaves of Acanthopanax sieboldianus. Phytochemistry 34, 1117-1121 (1993) https://doi.org/10.1016/S0031-9422(00)90727-1
  27. Van Damme, J., Opdenakker, G., Simpson, R. J., Rubira, M. R., Cayphas, S., Vink, A., Billiau, A., and Van Snick, J., Identification of the human 26-kD protein, interferon beta 2 (IFN-beta 2), as a B cell hybridoma/ plasmacytoma growth factor induced in interleukin 1 and tumor necrosis factor. J. Exp. Med. 165, 914-919 (1987) https://doi.org/10.1084/jem.165.3.914
  28. Vermes, B., Farkas, L., Nógrádi, M., Wagner, H., and Dirscherl, R., The synthesis of afzelin, paeonoside and kaempferol 3-O-$\beta$-rutinoside. Phytochemistry 15, 1320-1321 (1976) https://doi.org/10.1016/0031-9422(76)85106-0
  29. Yuba, P., Liu, Q.H., Oh, J.W., Woo, E.-R., Kang, K.W. 4-Hydroxykobusin inhibits the induction of nitric oxide synthase by inhibiting NF-k B and AP-1 activation. Biol. Pharm. Bull. 30, 1097-1101 (2007) https://doi.org/10.1248/bpb.30.1097
  30. Zhong, X.N., Otsuka, H., Ide, T., Hirata, E., Takushi, A., and Takeda, Y., Three flavonol glycosides from leaves of Myrsine Seguinii. Phytochemistry 46, 943-946 (1997) https://doi.org/10.1016/S0031-9422(97)00366-X