Summary
A novel bromine-containing pyrrole compound, hymenidin, has been isolated from the Okinawan marine spongeHymeniacidon sp. as a potent antagonist of serotonergic receptors and its structure elucidated using spectral data.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
The authors thank Dr. T. Hoshino (Mukaishima Marine Biological Station, Hiroshima University) for his kind identification of the marine sponge, Prof. T. Miyazawa, Mr K. Wakamatsu and Dr T. Higashijima for the NMR measurement, Mr Z. Nagahama for his assistance in collecting the marine sponge, and Miss M. Hamashima of this institute for her technical assistance.
Kobayashi, J., Ohizumi, Y., Nakamura, H., Yamakado, T., Matsuzaki, T., and Hirata, Y., Experientia39 (1983) 67.
Kobayashi, J., Nakamura, H., Ohizumi, Y., and Hirata, Y., Tetrahedron lett.27 (1986) 1191.
Ohizumi, Y., Nakamura, H., and Kobayashi, J., Eur. J. Pharmac.120 (1986) 245.
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., Ohizumi, Y., Nakamura, H., Hirata, Y., Wakamatsu, K., and Miyazawa, T., Experientia42 (1986) 1064.
Kobayashi, J., Nakamura, H., Ohizumi, Y., and Hirata, Y. Toxicon19 (1981) 757.
Cimino, G., De Stefano, S., Minale, L., and Sadano, G., Comp. Biochem. Physiol.50B (1975) 279.
Scott, A.I. (Ed.), in: Interpretation of the Ultraviolet Spectra of Natural Products, p. 167. Pergamon Press, New York 1964.
Nakamura, H., Ohizumi, Y., Kobayashi, J., and Hirata, Y., Tetrahedron Lett.25 (1984) 2475. The spongeAgelas sp. used was later identified asAgelas nemoechinata.
1:13C NMR (DMSO-d6; ° in ppm); 160.2 (s, C-6) 147.8 (s, C-13), 127.9 (s, C-5), 126.7 (d, C-10), 125.2 (s, C-11), 121.0 (d, C-2), 113.5 (d, C-9), 112. 1 (d, C-4), 111.2 (d, C-15), 95.4 (s, C-3) and 39.3 (t, C-8).
Albizati, K.F., and Faulkner, D.J., J. org. Chem.50 (1985) 4163.
Garcia, E.E., Benjamin, L.E., and Fryer, R.I., Chem. Commun.1973, 78.
Walker, R.P., Faulkner, D.J., Engen, D.V., and Clardy, J., J. Am. chem. Soc.103 (1981) 6772.
Sharma, G., and Magdoff-Fairchild, B., J. org. Chem.42 (1977) 4118.
De Nanteuil, G., Ahond, A., Guilhem, J., Poupat, C., Dau, E.T.H., Potier, P., Pusset, M., Pusset, J., and Laboute, P., Tetrahedron41 (1985) 6019.
Kitagawa, I., Kobayashi, M., Kitanaka, K., Kido, M., and Kyogoku, Y., Chem. pharm. Bull.31 (1983) 2321.
Cimino, G., De Rosa, S., De Stefano, S., Mazzarella, L., Puliti, R., and Sodano, G., Tetrahedron Lett.23 (1982) 767.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kobayashi, J., Ohizumi, Y., Nakamura, H. et al. A novel antagonist of serotonergic receptors, hymenidin, isolated from the Okinawan marine spongeHymeniacidon sp.. Experientia 42, 1176–1177 (1986). https://doi.org/10.1007/BF01941300
Issue Date:
DOI: https://doi.org/10.1007/BF01941300