Asmarines A-F, novel cytotoxic compounds from the marine sponge Raspailia species

Journal of Natural Products

Volumn 63, Issue 3, 2000, Pages 299-304

  Yosief, Tesfamariam ^a   Rudi, Amira ^a   Kashman, Yoel ^a  

^a TEL AVIV UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ASMARINE A; ASMARINE B; ASMARINE C; ASMARINE D; ASMARINE E; ASMARINE F; CYTOTOXIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; CATALYSIS; CYTOTOXICITY; DRUG ISOLATION; EXTRACTION; METHYLATION; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SPECIES DIFFERENCE; SPECTROSCOPY; SPONGE (PORIFERA); STRUCTURE ANALYSIS; X RAY DIFFRACTION;

ANIMALS; ANTINEOPLASTIC AGENTS; HETEROCYCLIC COMPOUNDS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; PORIFERA;

GOSSYPIUM HIRSUTUM; PORIFERA; PUFFINUS AURICULARIS; RASPAILIA;

EID: 0034062561     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np9902690     Document Type: Article

References (17)

1. Goldshlager-Koren, G.; Aknin, M; Gaydou, E. M.; Kashman, Y. J. Org. Chem. 1998, 63, 4601 4603.
2. Kelman, D.; Kushmaro, A.; Loya, Y.; Kashman, Y.; Benayahu, Y. Mar. Ecol. Prog. Ser. 1998, 169, 87-95.
3. Yosief, T.; Rudi, A.; Wolde-ab, Y.; Kashman, Y. J. Nat. Prod. 1998, 61, 491 493.
4. Yosief, T.; Rudi, A.; Stein, Z.; Goldberg, I.; Gravalos, G. M. D.; Schleyer, M; Kashman, Y. Tetrahedron Lett. 1998, 39, 1445-1448.
5. Rudi, A.; Kashman, Y. J. Nat. Prod. 1992, 55, 1408-1414.
6. Ishada, K.; Ishbashi, M.; Shigemori, H.; Sasaki, T.; Kobayashi, J. Chem. Pharm. Bull. 1992, 40, 766 769.
7. Fukuzawa, S.; Matsunaga, S.; Fusetani, N. Tetrahedron Lett. 1996, 37, 1447 1448.
8. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley-Interscience: New York, 1994; p 991.
9. 4 there was a mistake in the stereochemistry of C-5 and C-10. The discussion, however, was correct.
10. Carney, J. R.; Scheuer, P. J. Tetrahedron Lett. 1993, 34, 3727-3730.
11. Schmitz, F. J.; Lakshmi, V.; Powell, D. R.; van der Helm, D. J. Org. Chem. 1984, 49, 241-244.
12. Byoungko, M.; Baker, B. J.; McClintock, J. B. J. Nat. Prod. 1998, 61, 116-118.
13. Kang, H. J.; Fenical, W. Tetrahedron Lett. 1997, 38, 941-944.
14. Originally, a different substitution pattern was suggested for 3 due to incorrect interpretation of its NMR data. After changing the ratio between 3 and 4, the individual correlation became clear, and the structure is here corrected.
15. Cherkiz, S.; Kashman, Y. Synthesis 1974, 885-887.
16. 2O-MeOH conditions did not give a compound similar to 9.
17. Yenuka, Y.; Halperin, G. J. Org. Chem. 1974, 39, 3047-3048.