Summary
The Ca2+-releasing action of several derivatives of eudistomin D isolated from a marine tunicate was compared with that of caffeine. It was found that 9-methyl-7-bromoeudistomin D was approximately 1000 times more potent than caffeine in causing Ca2+ release from the sarcoplasmic reticulum.
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Endo, M., Physiol. Rev.57 (1977) 71.
Martonosi, A. N., Physiol. Rev.64 (1984) 1240.
Scheider, M. F., A. Rev. Physiol.43 (1981) 507.
Rousseau, E., Ladine, J., Liu, Q.-Y., and Meissner, G., Archs Biochem. Biophys.267 (1988) 75.
This compound obtained the number one and the numerical order is identical with that in the table.
Kobayashi, J., Harbour, G. C., Gilmore, J., and Rinehart, K. L. Jr, J. Am. chem. Soc.106 (1984) 1526.
Rinehart, K. L. Jr, Kobayashi, J., Harbour, G. C., Gilmore, J., Mascal, M., Holt, T. G., Shield, L. S., and Lafargue, F., J. Am. chem. Soc.109 (1987) 3378.
Nakamura, Y., Kobayashi, J., Gilmore, J., Mascal, M., Rinehart, K. L. Jr, Nakamura, H., and Ohizumi, Y., J. biol. Chem.261 (1986) 4139.
Kobayashi, J., Taniguchi, M., Hino, T., and Ohizumi, Y., J. Pharm. Pharmac.40 (1988) 62.
Suzuki, H., Org. Syn.51 (1971) 94.
Compound2: mp.≈280°C (decomp.); EI mass m/z 354 (M+), 356 and 358; UV (MeOH) λmax 212 (ε 13000), 242 (15000), 254 (12000), 297 (7000), and 388 (3000) nm;1H NMR (DMSO-d6, 500 MHz) δ 4.25 (3H, s, N−CH3), 7.46 (1H, s, H-8), 8.40 (1H, d, J=3 Hz, H-4), 8.55 (1H, d, J=3 Hz, H-3), and 8.97 (1H, brs, H-1).
Compound6: mp. 145≈148°C; UV (MeOH) λmax 218 (ε 8600), 246 (9400), 267 (12000), 294 (5100), and 308 (3000) nm; EI mass m/z 266 (M+, 100), 267 (26), 268 (67), and 270 (12);1H NMR (DMSO-d6, 500 MHz) δ 4.25 (3H, s, N−CH3), 7.34 (1H, s, H-8), 8.38 (1H, d, J=5.5 Hz, H-4), 8.43 (1H, d, J=5.5 Hz, H-3), and 9.13 (1H, s, H-1).
Compound8: mp.≈200°C (decomp.); EI mass m/z 436 (M+); UV (MeOH) λmax 220 (ε 5100), 238 (30000), 290 (11000), 299 (15000), and 375 (5100) nm;1H NMR (DMSO-d6, 500 MHz) δ 5.78 (1H, s, H-8), 8.39 (1H, brs, H-4), 8.77 (1H, brs, H-3), 8.98 (1H, brs, H-1), 10.3 (1H, s, OH), and 11.55 (1H, brs, H-9).
Compound9: mp. 197≈199°C (decomp.); UV (MeOH) λmax 220 (10000), 242 (8100), 262 (6200), 300 (3700), and 384 (1800) nm; EI mass m/z 450 (M+);1H NMR (DMSO-d6, 500 MHz) δ 4.27 (3H, s, N−CH3), 7.71 (1H, s, H-8), 8.43 (1H, d, J=5.4 Hz, H-4), 8.88 (1H, d, J=5.4 Hz, H-3), and 9.08 (1H, s, H-1).
Kim, D. H., Ohnishi, S. T., and Ikemoto, N., J. biol. Chem.258 (1983) 9662.
Tsien, R. Y., and Rink, T. J., J. neurosci. Meth.4 (1981) 73.
The minimum effective concentration of compound1 in ethanol was 1.5 μM, which was relatively a lower concentration than that in dimethyl sulfoxide. Ethanol appears to elevate the Ca2+-releasing activity of any compound containing caffeine.
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The authors thank Ms A. Muroyama of this institute for her technical assistance and Prof. K. L. Rinehart of University of Illinois for his encouragement.
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Kobayashi, J., Ishibashi, M., Nagai, U. et al. 9-Methyl-7-bromoeudistomin D, a potent inducer of calcium release from sarcoplasmic reticulum of skeletal muscle. Experientia 45, 782–783 (1989). https://doi.org/10.1007/BF01974589
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DOI: https://doi.org/10.1007/BF01974589