Negombins A-I, new chlorinated polyfunctional diterpenoids from the marine sponge negombata species

Organic Letters

Volumn 9, Issue 12, 2007, Pages 2337-2340

  Rudi, Amira ^a   Benayahu, Yehuda ^a   Kashman, Yoel ^a  

^a TEL AVIV UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; NEGOMBIN A; NEGOMBIN B; NEGOMBIN C; NEGOMBIN D; UNCLASSIFIED DRUG;

ANIMAL; ARTICLE; CHEMISTRY; CLASSIFICATION; CONFORMATION; ISOLATION AND PURIFICATION; SPECIES DIFFERENCE; SPONGE (PORIFERA); STEREOISOMERISM;

ANIMALS; DITERPENES; MOLECULAR CONFORMATION; PORIFERA; SPECIES SPECIFICITY; STEREOISOMERISM;

EID: 34250837435     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070633j     Document Type: Article

References (21)

1. Chill, L.; Rudi, A.; Benayahu, Y.; Schleyer, M.; Kashman, Y. Org. Lett. 2004, 6, 755-758.
2. Sorek, H.; Rudi, A.; Gueta, S.; Reyes, F.; Martin, J. M.; Aknin, M.; Gaydou, E.; Vacelet, J.; Kashman, Y. Tetrahedron 2006, 62, 8838-8843.
3. Spector, I.; Shochet, N.; Kashman, Y.; Groweiss, A. Science 1983, 219 (4584) 493-495.
4. Kelly-Borges, M.; Vacelet, J. Memoris Queensland Museum 1995, 38, 477-503.
5. The red orange sponge is growing on steep reef walls exposed to strong water currents and was collected at a depth of 22-25 m. Voucher specimens (ZMTAU PO 25464-25466) are deposited at the Zoological Museum, Tel Aviv University, Israel. A new collection and comprehensive work is required for identification of the sponge which is close to Sigmosceptrella another genus, besides the Negombata, of the Podospongiidae family.
6. 2Cl, 334.1693).
7. 4Cl, 383.1981).
8. 2Cl, 353.2239).
9. 2Cl, 336.1853).
10. H 2.04, 2.16, 3H each 6.05d (H-11), 4.90bs (H-9)].
11. 3Cl, 365.1876).
12. H 3.40s (H-1) and 4.33bs (H-9).
13. 4Cl, 380.1747).
14. 4Cl, 380.1747).
15. 3Cl, 352.6771).
16. Stratmann, K.; Moore, R. E.; Bonjouklian, R.; Deeter, J. B.; Patterson, G. M. L.; Shaffer, S.; Smith, C. D.; Smitka, T. A. J. Am Chem. Soc. 1994, 116, 9935-9942.
17. Radical chlorination, on the other hand, is well known, for example, hydrogen substitution of methyl protons to produce mono-, di- and trichloromethyl groups.
18. Dozens of studied Red Sea Negombata sp. were never found to contain negombins.
19. Paul, V. J.; Seo, Y.; Cho, K. W.; Rho, J.-R.; Shin, T.; Bergquist, P. R. J. Nat Prod. 1997, 60, 1115-1120 and references therein.
20. Feld, H.; Hertewich, U. M.; Zapp, J.; Becker, H. Phytochemistry 2005, 66, 1094-1099.
21. Meyer, N. B.; Ferringini, N. R.; Putnam, J. E.; Nichols, D. E.; McLaughlin, J. L. Med. Plant Res. 1982, 45, 31-34.