Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

A New Furofuran Lignan from Geranium thunbergii Sieb. et Zuccc.

  • Published : 2006.12.31
Download PDF
⟨ Previous Next ⟩

Abstract

A new furofuran lignan, 4-hydroxykobusin (3), together with known lignans, kobusin (1), and 7,7'-dihydroxybursherenin (2), were isolated from the whole plant of Geranium thunbergii Sieb. et Zucc (Geraniaceae). The structures were determined based on the spectral data and a comparison with the published data. This is the first report of the presence of furofuran lignan in Geranium species.

Keywords

References

  1. Abe, F. and Yamauchi, T., 9${\alpha}$-hydroxypinoresinol, 9${\alpha}$-hydroxymedioresinol and related lignans from Allamanda neriifolia. Phytochemistry, 27, 575-577 (1988) https://doi.org/10.1016/0031-9422(88)83144-3
  2. Ahmed, A. A., Mahmoud, A. A., Ali, E. T., Tzakou, O., Couladis, M., Mabry, T. J., Gáti, T., and Tóth, G., Two highly oxygenated eudesmanes and 10 lignans from Achillea holostericea. Phytochemistry, 59, 851-856 (2002) https://doi.org/10.1016/S0031-9422(01)00442-3
  3. Bae, K. W., The medicinal plants of Korea. Kyo-Hak Publishing Co., Seoul, pp (2000)
  4. Enders, D., Lausberg, V., Signore, G. D., and Berner, O. M., A general approach to the asymmetric synthesis of lignans: (-)- methyl piperitol, (-)-sesamin, (-)-aschantin, (+)-yatein, (+)- dihydroclusin, (+)-bursheran, and (-)-isostegane. Synthesis, 4, 515-522 (2002)
  5. 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
  6. 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
  7. Hou, C.-C., Lin, S.-J., Cheng, J.-T., and Hsu, F.-L., Antidiabetic dimeric guianolides and a lignan glycosides from Lactuca indica. J. Nat. Prod., 66, 625-629 (2003) https://doi.org/10.1021/np0205349
  8. Hua, X. G., Kim, J. A., Park, S. H., Son, A. R., Chang, T. S., Chang, H. W., Chung, S. R., and Lee, S. H., Isolation of melanin biosynthetic inhibitory compounds from the flowers of Magnolia denudata. Kor. J. Pharmacogn., 35, 152-156 (2004)
  9. 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
  10. Iida, T., Nakano, M., and Ito, K., Hydroperoxysesquiterpene and lignan constituents of Magnolia kobus. Phytochemistry, 21, 673-675 (1982) https://doi.org/10.1016/0031-9422(82)83163-4
  11. 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
  12. Kim, M.-R., Moon, H.-I., Chung, J. H., Moon, Y. H., Hahm, K.-S., and Woo, E.-R., Matrix matalloproteinase-1 inhibitor from the stem bark of Styrax japonica. Chem. Pharm. Bull., 52, 1466- 1469 (2004) https://doi.org/10.1248/cpb.52.1466
  13. Kwon, H. C., Choi, S. U., Lee, J. O., Bae, K. H., Zee, O. P., and Lee, K. R., Two new lignans from Lindera obtusiloba Blume. Arch. Pharm., Res., 22, 417-422 (1999) https://doi.org/10.1007/BF02979069
  14. Latip, J., Hartley, T. G., and Waterman, P. G., Lignans and coumarins metabolites from Melicope hayesii. Phytochemistry, 51, 107-110 (1999) https://doi.org/10.1016/S0031-9422(98)00720-1
  15. Lim, Y.-H., Leem, M.-J., Shin, D.-H., Chang, H.-B., Hong, S.-W., Moon, E-Y., Lee, D.-K., Yoon, S.-J., and Woo, W.-S., Cytotoxic constituents from the roots of Anthriscus sylvestris. Arch. Pharm. Res., 22, 208-212 (1999) https://doi.org/10.1007/BF02976548
  16. Malarz, J., Stojakowska, A., Szneler, E., and Kisiel, W., Furofuran lignans from a callus culture of Cichorium intybus. Plant Cell. Rep., 24, 246-249 (2005) https://doi.org/10.1007/s00299-005-0953-9
  17. Matsushita, H., Miyase, T., and Ueno, A., Lignan and terpene glycosides from Epimedium sagittarium. Phytochemistry, 30, 2025-2027 (1991) https://doi.org/10.1016/0031-9422(91)85061-4
  18. Min, B.-S., Cui, H. S., Lee, H.-K., Sok, D.-E., and Kim, M. R., A new furofuran lignan with antioxidant and antiseizure activities from the leaves of Petasites japonica. Arch. Pharm. Res., 28, 1023-1026 (2005) https://doi.org/10.1007/BF02977395
  19. Ogiku, T., Yoshida, S., Ohimizu, H., and Iwasaki, T., Stereocontrolled synthesis of diequatorial and axial-equatorial furofuran lignans. J. Org. Chem., 60, 1148-1153 (1995) https://doi.org/10.1021/jo00110a016
  20. 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
  21. Tanoguchi, M., Hosono, E., Kitaoka, M., Arimoto, M., and Yamaguchi, H., Studies on the constituents of the seeds of Hernandia ovigera L. IX. Identification of two dibenzylbutyrolactone- type lignans and an attempt of conversion into phenyltetralin-type lignan. Chem. Pharm. Bull., 39, 1873- 1876 (1991) https://doi.org/10.1248/cpb.39.1873
  22. Tene, M., Tane, P., Sondengam, B. L., and Connolly, J. D., Lignans from the roots of Echinops giganteus. Phytochemistry, 65, 2101-2105 (2004) https://doi.org/10.1016/j.phytochem.2004.05.014
  23. 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