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 ofGeranium thunbergii Sieb. et Zucc (Geraniacaceae). 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 inGeranium species.
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Abe, F. and Yamauchi, T. 9α-hydroxypinoresinol, 9α-hydroxymedioresinol and related lignans fromAllamanda neriifolia.Phytochemistry, 27, 575–577 (1988).
Ahmed, A. A., Mahmoud, A. A., Ali, E. T., Tzakou, O., Couladis, M., Mabry, T. J., Gati, T., and Toth, G., Two highly oxygenated eudesmanes and 10 lignans fromAchillea holostericea.Phytochemistry, 59, 851–856 (2002).
Bae, K. W., The medicinal plants of Korea. Kyo-Hak Publishing Co., Seoul, pp (2000).
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).
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).
Hirano, T., Akira, S., Taga, T., and Kishimoto, T., Biological and clinical aspects of interleukin 6.Immunol. Today, 11, 443–449 (1990).
Hou, C.-C., Lin, S.-J., Cheng, J.-T., and Hsu, F.-L., Antidiabetic dimeric guianolides and a lignan glycosides fromLactuca indica.J. Nat. Prod., 66, 625–629 (2003).
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 ofMagnolia denudata.Kor. J. Pharmacogn., 35, 152–156 (2004).
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).
Iida, T., Nakano, M., and Ito, K., Hydroperoxysesquiterpene and lignan constituents ofMagnolia kobus, Phytochemistry, 21 673–675 (1982).
Ito, H., Hatano, T., Namba, O., Shirono, T., Okuda, T., and Yoshida, T., Constituents ofGeranium thunbergii Sieb. Et Zucc. XV. Modified dehydroellagitannins, geraniinic acids B and C, and phyllanthusiin F..Chem. Pharm. Bull, 47, 1148–1151 (1999).
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 ofStyrax japonica.Chem. Pharm. Bull., 52, 1466–1469 (2004).
Kwon, H. C., Choi, S. U., Lee, J. O., Bae, K. H., Zee, O. P., and Lee, K. R., Two new lignans fromLindera obtusiloba Blume.Arch. Pharm.,Res, 22, 417–422 (1999).
Latip, J., Hartley, T. G., and Waterman, P. G., Lignans and coumarins metabolites fromMelicope hayesii.Phytochemistry, 51, 107–110 (1999).
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 ofAnthriscus sylvestris.Arch. Pharm. Res., 22, 208–212 (1999).
Malarz, J., Stojakowska, A., Szneler, E., and Kisiel, W., Furofuran lignans from a callus culture ofCichorium intybus.Plant Cell. Rep., 24, 246–249 (2005).
Matsushita, H., Miyase, T., and Ueno, A., Lignan and terpene glycosides fromEpimedium sagittarium.Phytochemistry, 30, 2025–2027 (1991).
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 ofPetasites japonica.Arch. Pharm. Res., 28, 1023–1026 (2005).
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).
Okuda, T., Yoshida, T., Hatano, T., Ikeda, Y., Shingu, T., and Inoue, T., Constituents ofGeranium 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).
Tanoguchi, M., Hosono, E., Kitaoka, M., Arimoto, M., and Yamaguchi, H., Studies on the constituents of the seeds ofHemandia ovigera L. IX. Identification of two dibenzylbutyrolactone-type lignans and an attempts of conversion into phenyltetralin-type lignan.Chem. Pharm. Bull., 39, 1873–1876 (1991).
Tene, M., Tane, P., Sondengam, B. L., and Connolly, J. D., Lignans from the roots ofEchinops giganteus.Phytochemistry, 65, 2101–2105 (2004).
Van Damme, J., Opdenakker, G., Simpson, R. J., Rubira, M. R., Cayphas, S., Vink, A., Billiau, A., andVan 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).
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Liu, QH., Jeong, JE., Choi, E.J. et al. A new furofuran lignan fromGeranium thunbergii Sieb. et Zucc. Arch Pharm Res 29, 1109–1113 (2006). https://doi.org/10.1007/BF02969300
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DOI: https://doi.org/10.1007/BF02969300