New isomalabaricane triterpenes from the marine sponge Stelletta globostellata that induce morphological changes in rat fibroblasts

Journal of Natural Products

Volumn 63, Issue 2, 2000, Pages 205-209

  Naoya, Oku ^a   Matsunaga, Shigeki ^a   Wada, Shun Ichi ^a   Watabe, Shugo ^a   Fusetani, Nobuhiro ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

NATURAL PRODUCT; STELLIFERIN DERIVATIVE; TERPENOID; TRITERPENE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; FIBROBLAST CULTURE; MARINE ENVIRONMENT; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAT; SPONGE (PORIFERA); STEREOCHEMISTRY;

ACETYLATION; ANIMALS; ANTINEOPLASTIC AGENTS; CELL SURVIVAL; CELLS, CULTURED; COLORING AGENTS; FIBROBLASTS; PORIFERA; RATS; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; SPECTROPHOTOMETRY, ULTRAVIOLET; TETRAZOLIUM SALTS; THIAZOLES; TRITERPENES;

ANIMALIA; PORIFERA; STELLETTA;

EID: 0342614927     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np990333d     Document Type: Article

References (16)

1. Bioactive Marine Metabolités Series. 96. Part 95: Matsunaga, S.; Yamashita, T.; Tsukamoto, S.; Fusetani, N. J. Nat. Prod. 1999, 62, 1202-1204.
2. Although Stelletta globostellata (often called Rhabdastrella or Aurora globostellata) and Jaspis stellifera, both of which contain isomalabaricane triterpenes, are closely related, they are apparently different. It is most likely that the latter sponge does not belong to the genus Jaspis (van Soest, Rob W. M., personal communication).
3. Ryu, G.; Matsunaga, S.; Fusetani, N. J. Nat. Prod. 1996, 59, 512-514.
4. Rao, Z.; Deng, S.; Wu, H.; Jiang, S. J. Nat. Prod. 1997, 60, 1163-1164.
5. Tsuda, M.; Ishibashi, M.; Agemi, K.; Sasaki, T.; Kobayashi, J. Tetrahedron 1991, 47, 2181-2194.
6. McCabe, T.; Clardy, J.; Minale, L.; Pizza, C.; Zollo, F.; Riccio, R. Tetrahedron Lett. 1982, 23, 3307-3310.
7. We use the numbering system used for stelliferins to avoid confusion.
8. 3, the structures of globostellatic acids B-D were drawn with (13Z)-geometry. They have (13E)-geometry on the basis of the chemical shift values for H-15. We thank Professor M. Valeria D'Auria, University of Naples, for pointing out the misassignment.
9. Otani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
10. 1H NMR spectrum.
11. Kobayashi, J.; Yuasa, K.; Kobayashi, T.; Sasaki, T.; Tsuda, M. Tetrahedron 1996, 52, 5745-5750.
12. Only the 12α-alcohol was produced.
13. Sata, N. U.; Wada, S.; Matsunaga, S.; Watabe, S.; van Soest, R. W. M.; Fusetani, N. J. Org. Chem. 1999, 64, 2331-2339.
14. McKee, T. C.; Bokesch, H. R.; McCormick, J. L.; Rashid, M. A.; Spielvogel, D.; Gustafson, K. R.; Alavanja, M. M.; Cardellina, J. H., II; Boyd, M. R. J. Nat. Prod. 1997, 60, 431-438.
15. McCormick, J. L.; McKee, T. C.; Cardellina, J. H., II; Leid, M.; Boyd, M. R. J. Nat. Prod. 1996, 59, 1047-1050.
16. Fukuzawa, S.; Matsunaga, S.; Fusetani, N. J. Org. Chem. 1995, 60, 608-614.