New spirocyclic sesquiterpenes from the marine sponge Geodia exigua

Tetrahedron

Volumn 59, Issue 6, 2003, Pages 731-736

  Uy, Mylene M ^a   Ohta, Shinji ^a   Yanai, Mihoko ^a   Ohta, Emi ^a   Hirata, Toshifumi ^a   Ikegami, Susumu ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

Biologically active compounds; Natural products; Spiro compounds; Sponges

Indexed keywords

AMINE; AXISONITRILE; EXICARBAMATE; EXIGUAMIDE; EXIGURIN; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CELL FATE; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); EMBRYO DEVELOPMENT; GEODIA EXIGUA; MARINE ENVIRONMENT; PRIORITY JOURNAL; SEA URCHIN; SPECTROSCOPY; SPONGE (PORIFERA); STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

ECHINOIDEA; GEODIA;

EID: 0037415521     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01619-8     Document Type: Article

References (38)

1. Angerer L.M., Angerer R.C. Develop. Biol. 213:2000;1-12.
2. Ohta S., Okada H., Kobayashi H., Oclarit J.M., Ikegami S. Tetrahedron Lett. 34:1993;5935-5938.
3. Ohta S., Kobayashi H., Ikegami S. Tetrahedron Lett. 35:1994;4579-4580.
4. Ohta S., Kobayashi H., Ikegami S. Biosci. Biotech. Biochem. 58:1994;1752-1753.
5. Ikegami S., Kobayashi H., Myotoishi Y., Ohta S., Kato K.H. J. Biol. Chem. 269:1994;23262-23267.
6. Ohta S., Uno M., Yoshimura M., Hiraga Y., Ikegami S. Tetrahedron Lett. 37:1996;2265-2266.
7. Uno M., Ohta S., Ohta E., Ikegami S. J. Nat. Prod. 59:1996;1146-1148.
8. Ohta S., Ohta E., Ikegami S. J. Org. Chem. 62:1997;6452-6453.
9. Yanai M., Ohta S., Ohta E., Ikegami S. Tetrahedron. 54:1998;15607-15612.
10. Ohta E., Ohta S., Ikegami S. Tetrahedron. 57:2001;4699-4703.
11. Uy M.M., Ohta S., Yanai M., Ohta E., Hirata T., Ikegami S. Bioorg. Med. Chem. Lett. 12:2002;3037-3039.
12. Okino T., Yoshimura E., Hirota H., Fusetani N. Tetrahedron. 52:1996;9447-9454.
13. Kusumi T., Fukushima T., Ohtani I., Kakisawa H. Tetrahedron Lett. 32:1991;2939-2942.
14. Kingston J.F., Benson E., Gregory B., Fallis A.G. J. Nat. Prod. 42:1979;528-531.
15. Pettit G.R., Rideout J.A., Hasler J.A. J. Nat. Prod. 44:1981;588-592.
16. Lidgren G., Bohlin L., Bergam J. Tetrahedron Lett. 27:1986;3283-3284.
17. Chan W.R., Tinto W.F., Manchand P.S., Todaro L.J. J. Org. Chem. 52:1987;3091-3093.
18. Tinto W.F., Lough A.J., Mclean S., Reynolds W., Yu M., Chan W.R. Tetrahedron. 54:1998;4451-4458.
19. Lindgren G., Bohlin L., Christophersen C. J. Nat. Prod. 51:1988;1277-1280.
20. Pettit G.R., Rideout J.A., Hasler J.A. Comp. Biochem. Physiol. C. 96:1990;305-306.
21. Wang G.Y.S., Crews P. Tetrahedron Lett. 37:1996;8145-8146.
22. Capon R.J., Skene C., Lacey E., Gill J.H., Wadsworth D., Friedel T. J. Nat. Prod. 62:1999;1256-1259.
23. Tabudrava J.N., Jaspas M. J. Nat. Prod. 64:2001;813-815.
24. Zhang W.H., Che C.T. J. Nat. Prod. 64:2001;1489-1492.
25. Di Blasio B., Fattorusso E., Magno S., Mayol L., Pedone C., Santacroce C., Sica D. Tetrahedron. 32:1976;473-478.
26. Angerhofer C.K., Pezzuto J.M., Konig G.M., Wright A.D., Sticher O. J. Nat. Prod. 55:1992;1787-1789.
27. Alvi K.A., Tenenbaum L., Crews P. J. Nat. Prod. 54:1991;71-78.
28. Minale L., Riccio R., Sodano G. Tetrahedron. 30:1974;1341-1343.
29. Burreson B.J., Christophersen C., Scheuer P.J. Tetrahedron. 31:1975;2015-2018.
30. Ciminiello E., Fattorusso E., Magno S., Mayol L. J. Org. Chem. 49:1984;3949-3951.
31. Ciminiello P., Fattorusso E., Magno S., Mayol L. Experientia. 42:1986;625-627.
32. Burgoyne D.L., Dumdei E.J., Andersen R.J. Tetrahedron. 49:1993;4503-4510.
33. Gulavita N.K., de Silva E.D., Hagadone M.R., Karuso P., Scheuer P.J. J. Org. Chem. 1986;5136-5139.
34. Tanaka Y. Develop. Growth Differ. 21:1979;331-342.
35. We investigated the effects of 1-4 on embryogenesis of the starfish, Asterina pectinifera, which belongs to the same phylum Echinodermata as H. pulcherrimus. In contrast to sea urchin embryos, no spicules form in starfish embryos. As expected, compounds 1-4 at 25 μM did not affect embryonic development up to the gastrula stage of this species.
36. Altomare A., Cascarano M., Giacovazzo C., Guagliardi A. J. Appl. Crystallogr. 26:1994;343.
37. Beurskens P.T., Admiraal G., Beurskens G., Bosman W.P., de Gelder R., Israel R., Smits J.M.M. The DIRDIF-94 Program System, Technical Report of the Crystallography Laboratory. 1994;University of Nijmegen, The Netherlands.
38. Shimomura M., Miyaoka H., Yamada Y. Tetrahedron Lett. 40:1999;8015-8017.