Anticonvulsant compounds from the wood ofCaesalpinia sappan L.
- 267 Downloads
80% Aqueous MeOH extracts from the wood ofCaesalpinia sappan, which showed remarkable anticonvulsant activity, were fractionated using EtOAc,n-BuOH, and H2O. Among them, the EtOAc fraction significantly inhibited the activities of two GABA degradative enzymes, succinic semialdehyde dehydrogenase (SSADH) and succinic semialdehyde reductase (SSAR). Repeated column chromatographies for the fraction guided by activity test led to the isolation of the two active principal components. Their chemical structures were determined to be sappanchalcone and brazilin based on spectral data. The pure compounds, sappanchalcone (1) and brazilin (2), inactivated the SSAR activities in a dose dependent manner, whereas SSADH was inhibited partially by sappanchalcone and not by brazilin.
Key wordsCaesalpinia sappan Anticonvulsant Brazilin Sappanchalcone Succinic semialdehyde reductase Succinic semialdehyde dehydrogenase
- Baek, N.-I., Choi, S. Y., Park, J. K., Cho, S.-W., Ahn, E.-M., Jeon, S. G., Lee, B. R., Bahn, J. H., Kim, Y. K. and Shon, I. H., Isolation and identification of succinic semialdehyde dehydrogenase inhibitory compound from the rhizome ofGastrodia elata B.Arch. Pharm. Res., 22, 219–224 (1999).PubMedCrossRefGoogle Scholar
- Choi, S. Y., Cho, S.-W. and Choi, E. W., Effect of anticonvulsant drugs on succinic semialdehyde reductase from bovine brain.J. Applied. Pharmacol., 1, 93–97 (1993).Google Scholar
- Lee, B. R., Hong, J. W., Yoo, B. K., Lee, S. J., Cho, S.-W. and Choi, S. Y., Bovine brain succinic semialdehyde dehydrogenase; Purfication, kinetics and reactivity of lysyl residues connected with catalytic activity.Mol. Cells., 5, 611–617 (1995).Google Scholar
- Nagai, M., Nagumo, S., Lee, S.-M., Eguchi, I. and Kawai, K.-I., Protosappanin A, a novel biphenyl compound from Sappan lignum.Chem. Pharm. Bull., 34, 1–6 (1986).Google Scholar
- Namikoshi, M., Nakata, H., Yamada, H., Nagai, M. and Saitoh, T., Homoisoflavonoids and related compounds. II. Isolation and absolute configuration of 3,4-dihydroxylated homoisoflavans and brazilins fromCaesalpinia sappan L.,Chem. Pharm. Bull.,35, 2761–2773 (1987a).Google Scholar
- Namikoshi, M., Nakata, H., Nuno, M., Ozawa, T. and Saitoh, T., Homoisoflavonoids and related compounds. III. Phenolic constituents ofCaesalpinia japonica Sieb.et Zucc.,Chem. Pharm. Bull., 35, 3568–3575 (1987b).Google Scholar
- Saitoh, T., Sskashita, S., Nakata, H., Shimokawa, T., Kinjo, J.-E., Yamahara, J., Yamasaki, M. and Nohara, T., 3-Benzylchroman derivatives related to brazilin from Sappan lignum.Chem. Pharm. Bull., 34 2506–2511 (1986).Google Scholar
- Shimokawa, T., Kinjo, J.-E., Yamahara, J., Yamasaki, M. and Nohara, T., Two novel compounds fromCaesalpinia sappan L.Chem. Pharm. Bull., 33, 3545–3547 (1985).Google Scholar
- Simler, S., Ciesielaki, L., Maitre, M., Randrianarioa, H. and Mandel, P., Effect of dipropylacetate on audiogenic seizures and brain GABA levels.Biochem. Pharmacol., 25, 413–417 (1973).Google Scholar
- Soka, T., Dictionary of Chinese Drugs, Shanghai Science Technology Shogaukan (Eds.), Shogakukan Press Tokyo, pp. 1627–1628, (1985).Google Scholar