Abstract
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.
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Anlezark, G., Horton, R. W., Meldrum, B. S. and Sawaya, M. C. B., Anticonvulsant action of ethanolamine-O-sulphate and dipropylacetate and metabolism of GABA in mice with audiogenic seizures.Biochem. Pharmacol., 25, 413–417 (1976).
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).
Bradford, M., A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding.Anal. Biochem., 72, 248–254 (1976).
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).
Cho, S.-W., Song, M. S., Kim, G. Y., Choi, E. Y., Kang, W. D. and Choi, S. Y., Purification, kinetics, and mechanism of an NADPH-dependent succinic semialdehyde reduct-ase from bovine brain.Eur. J. Biochem., 211, 757–762 (1993).
De Biase, D., Barra, D., Bossa, F., Pucci, P. and John, R. H., Chemistry of the inactivation of 4-aminobutyrate aminotransferase by the antiepileptic drug vigabatrin.J. Biol. Chem., 266, 20056–20061 (1991).
Fletcher, A. and Fowler, L. J., 4-aminobutyric acid metabolism in rat brain following chronic oral administration of ethanolamine-O-sulfate.Biochem. Pharmacol., 29, 1451–1454 (1980).
Gordin, Y., Heinler, H. L., Mark, J. and Madel, P., Effect of dipropylacetate on the degradative enzymes of the GABA shunt.FEBS Lett., 52, 251–254 (1975).
Kim, D.-S., Baek, N.-I., Oh, S. R., Jung, K. Y., Lee, I. S. and Lee, H.-K., NMR assignment of brazilein.Phytochemistry, 46, 177–178 (1997).
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).
Lippert, B., Metcalf, B. Y., Jung, M. J. and Casara, P., 4-aminohex-5-enoic acid; a selective catalytic inhibitor of 4-aminobutyrate aminotransferase in mammalian brain.Eur. J. Biochem., 74, 441–445, (1977).
Lloyd, K. G., Sherman, L. and Hornykiewicz, O., Distribution of high affinity sodium independent [3H]-v-aminobutyrate binding in the human brain. Alteration in Parkinson’s disease.Brain. Res., 127, 269–275 (1977).
Nagai, M., Nagumo, S., Eguchi, I., Lee, S.-M. and Suzuki, T., Sappanchalcone fromCaesalpinia sappan L., the proposed biosynthetic precursor of brazilin.Yakugaku Zasshi, 104, 935–938 (1984).
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).
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).
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).
Perry, T. L., Hansen, S. and Kloster, M., Hungtinton’s chorea: Deficiency of 4-aminobutyric acid in the brain.New. Engl. J. Med., 288, 337–342 (1973).
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).
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).
Simon, D. and Penry, J. K., Sodium dipropylacetate in the treatment of epilepsy.Epilepsia, 16, 549–573 (1975).
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).
Soka, T., Dictionary of Chinese Drugs, Shanghai Science Technology Shogaukan (Eds.), Shogakukan Press Tokyo, pp. 1627–1628, (1985).
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Baek, NI., Jeon, S.G., Ahn, EM. et al. Anticonvulsant compounds from the wood ofCaesalpinia sappan L.. Arch Pharm Res 23, 344–348 (2000). https://doi.org/10.1007/BF02975445
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DOI: https://doi.org/10.1007/BF02975445