Abstract
Bioassay-guided fractionation of a CH2Cl2-soluble fraction of the stems of Catalpa ovata led to isolation of a new naphthoquinone, 4-hydroxy-2-(2-methoxy-3-hydroxy-3-methyl-but-1-enyl)-4-hydro-1H-naphthalen-1-one (10), together with nine known compounds, catalponol (1), catalponone (2), catalpalactone (3), α-lapachone (4), 9-hydroxy-α-lapachone (5), 4,9-dihydroxy-α-lapachone (6), 9-methoxy-α-lapachone (7), 4-oxo-α-lapachone (8), and 9-methoxy-4-oxo-α-lapachone (9). The structures were elucidated on the basis of spectroscopic analyses. The inhibitory effects of these isolates on lipopolysaccharide-induced NO synthesis in RAW 264.7 cells were evaluated. Among them, catapalactone (3), 9-hydroxy-α-lapachone (5) and 4,9-dihydroxy-α-lapachone (6) exhibited potent inhibitory effects, with IC50 values of 9.80, 4.64 and 2.73 μM, respectively.
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Alderton, W. K., Cooper, C. E., and Knowles, R. G., Nitric oxide synthases: structure, function and inhibition. Biochem. J., 357, 593–615 (2001).
An, S. J., Pae, H. O., Oh, G. S., Choi, B. M., Jeong, S., Jang, S. I., Oh, H., Kwon, T. O., Song, C. E., and Chung, H. T., Inhibition of TNF-α, IL-1β, and IL-6 productions and NF-κB activation in lipopolysaccharide-activated RAW 264.7 macrophages by catalposide, an iridoid glycoside isolated from Catalpa ovata G. Don (Bignoniaceae). Int. Immunopharmacol., 2, 1173–1181 (2002).
Bae, K. H., Medicinal Plants of Korea. Kyo-Hak Publishing Co., Ltd., Seoul, pp. 466, (2000).
Cheng, Y. W., Chang, C. Y., Lin, K. L., Hu, C. M., Lin, C. H., and Kang, J. J., Shikonin derivatives inhibited LPS-induced NOS in RAW 264.7 cells via downregulation of MAPK/NF-κB signaling. J. Ethnopharmacol., 120, 264–271 (2008).
Fujiwara, A., Mori, T., Iida, A., Ueda, S., Hano, Y., Nomura, T., Tokuda, H., and Nishino, H., Antitumor-promoting naphthoquinones from Catalpa ovata. J. Nat. Prod., 61, 629–632 (1998).
Han, A. R., Min, H. Y., Nam, J. W., Lee, N. Y., Wiryawan, A., Suprapto, W., Lee, S. K., Lee, K. R., and Seo, E. K., Identification of a new naphthalene and its derivatives from the bulb of Eleutherine americana with inhibitory activity on lipopolysaccharide-induced nitric oxide production. Chem. Pharm. Bull., 56, 1314–1316 (2008).
Hong, S. S., Lee, S. A., Han, X. H., Hwang, J. S., Lee, C., Lee, D., Hong, J. T., Kim, Y., Lee, H., and Hwang, B. Y., ent-Kaurane diterpenoids from Isodon japonicus. J. Nat. Prod., 71, 1055–1058 (2008).
Inoue, H., Okuda, T., Hirata, Y., Nagakura, N., and Yoshizaki, M., Structure of catalpalactone, a new phthalide from Catalpa wood. Chem. Pharm. Bull., 15, 786–792 (1967).
Inoue, K., Inouye, H., Taga, T., Fujita, R., Osaki, K., and Kuriyama, K., Quinones and related compounds in higher plants. IX. Absolute structures of catalponol and its congeners. Chem. Pharm. Bull., 28, 1224–1229 (1980).
Inouye, H., Okuda, T., and Hayashi, T., Quinones and related compounds in higher plants. II. On the naphthoquinones and related compounds from Catalpa wood. Chem. Pharm. Bull., 23, 384–391 (1975).
Inouye, H., Ueda, S., Inoue, K., and Shiobara, Y., (2R)-catalponone, A biosynthetic intermediate for prenylnaphthoquinone congeners of the wood of Catalpa ovata. Phytochemistry, 20, 1707–1710 (1981).
Jung, B. S. and Shin, M. K., Encyclopedia of Illustrated Korean Natural Drugs. Young Lim Sa, Seoul, pp. 871–872, (1990).
Kanai, E., Machida, K., and Kikuchi, M., Studies on the constituents of Catalpa species. I Iridoids from Catalpae Fructus. Chem. Pharm. Bull., 44, 1607–1609 (1996).
Liu, S. H., Tzeng, H. P., Kuo, M. L., and Lin-Shiau, S. Y., Inhibition of inducible nitric oxide synthase by β-lapachone in rat alveolar macrophages and aorta. Br. J. Pharmacol., 126, 746–750 (1999).
Machida, K., Ando, M., Yaoita, Y., Kakuda, R., and Kikuchi, M., Studies on the constituents of Catalpa species. VI. Monoterpene glycosides from the fallen leaves of Catalpa ovata G. Don. Chem. Pharm. Bull., 49, 732–736 (2001).
Machida, K., Ogawa, M., and Kikuchi, M., Studies on the constituents of Catalpa species. II Iridoids from Catalpae Fructus. Chem. Pharm. Bull., 46, 1056–1057 (1998).
MacMicking, J., Xie, Q. W., and Nathan, C., Nitric oxide and macrophage function. Annu. Rev. Immunol., 15, 323–350 (1997).
Moon, D. O., Choi, Y. H., Kim, N. D., Park, Y. M., and Kim, G. Y., Anti-inflammatory effects of β-lapachone in lipopolysaccharide-stimulated BV2 microglia. Int. Immunopharmacol., 7, 506–514 (2007).
Nozaka, T., Watanabe, F., Ishino, M., Morimoto, I., Kondoh, H., Koyama, K., and Natori, S., A mutagenic new iridoid in the water extract of Catalpae Fructus. Chem. Pharm. Bull., 37, 2838–2840 (1989).
Oh, H., Pae, H. O., Oh, G. S., Lee, S. Y., Chai, K. Y., Song, C. E., Kwon, T. O., Chung, H. T., and Lee, H. S., Inhibition of inducible nitric oxide synthesis by catalposide from Catalpa ovata. Planta Med., 68, 685–689 (2002).
Pae, H. O., Oh, G. S., Choi, B. M., Shin, S., Chai, K. Y., Oh, H., Kim, J. M., Kim, H. J., Jang, S. I., and Chung, H. T., Inhibitory effects of the stem bark of Catalpa ovata G. Don. (Bignoniaceae) on the productions of tumor necrosis factor-α and nitric oxide by the lipopolisaccharide-stimulated RAW 264.7 macrophages. J. Ethnopharmacol., 88, 287–291 (2003).
Peraza-Sanchez, S. R., Chavez, D., Chai, H. B., Shin, Y. G., Garcia, R., Mejia, M., Fairchild, C. R., Lane, K. E., Menendez, A. T., Farnsworth, N. R., Cordell, G. A., Pezzuto, J. M., and Kinghorn, A. D., Cytotoxic constituents of the roots of Ekmanianthe longiflora. J. Nat. Prod., 63, 492–495 (2000).
Young, H. S., Kim, M. S., Park, H. J., Chung, H. Y., and Choi, J. S., Phytochemical study on Catalpa ovata. Arch. Pharm. Res., 15, 322–327 (1992).
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Park, B.M., Hong, S.S., Lee, C. et al. Naphthoquinones from Catalpa ovata and their inhibitory effects on the production of nitric oxide. Arch. Pharm. Res. 33, 381–385 (2010). https://doi.org/10.1007/s12272-010-0306-2
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DOI: https://doi.org/10.1007/s12272-010-0306-2