Elisabatins A and B: New amphilectane-type diterpenes from the west Indian Sea whip Pseudopterogorgia elisabethae

Journal of Natural Products

Volumn 62, Issue 7, 1999, Pages 997-999

  Rodríguez, Abimael D ^a   Ramírez, Catherine ^a   Rodríguez, Ileana I ^a  

^a UNIVERSITY OF PUERTO RICO RIO PIEDRAS   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; ELISABATIN A; ELISABATIN B; HEXANE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; COLOMBIA; CONJUGATE; EXTRACTION; INVERTEBRATE; MARINE ENVIRONMENT; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ANALYSIS;

ANIMALS; CNIDARIA; DITERPENES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET; WEST INDIES;

GORGONACEA; GORGONIA; INVERTEBRATA; PSEUDOPTEROGORGIA ELISABETHAE;

EID: 0039473734     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np990090p     Document Type: Article

References (18)

1. Graduate student sponsored by the NSF-MRCE and NIH-MBRS Programs of the University of Puerto Rico.
2. Undergraduate student sponsored by the NIH-MBRS Program of the University of Puerto Rico.
3. (a) Fenical, W. J. Nat. Prod. 1987, 50, 1001-1008. (b) Rodríguez, A. D. Tetrahedron 1995, 51, 4571-4618.
4. (a) Fenical, W. J. Nat. Prod. 1987, 50, 1001-1008. (b) Rodríguez, A. D. Tetrahedron 1995, 51, 4571-4618.
5. Rodríguez, A. D.; González, E.; Huang, S. D. J. Org. Chem. 1998, 63, 7083-7091.
6. (a) Look, S. A.; Fenical, W.; Matsumoto, G. K.; Clardy, J. J. Org. Chem. 1986, 51, 5140-5145. (b) Roussis, V.; Wu, Z.; Fenical, W.; Strobel, S. A.; Van Duyne, G. D.; Clardy, J. J. Org. Chem. 1990, 55, 4916-4922. (c) Harvis, C. A.; Burch, M. T.; Fenical, W. Tetrahedron Lett. 1988, 29, 4361-4364.
7. (a) Look, S. A.; Fenical, W.; Matsumoto, G. K.; Clardy, J. J. Org. Chem. 1986, 51, 5140-5145. (b) Roussis, V.; Wu, Z.; Fenical, W.; Strobel, S. A.; Van Duyne, G. D.; Clardy, J. J. Org. Chem. 1990, 55, 4916-4922. (c) Harvis, C. A.; Burch, M. T.; Fenical, W. Tetrahedron Lett. 1988, 29, 4361-4364.
8. (a) Look, S. A.; Fenical, W.; Matsumoto, G. K.; Clardy, J. J. Org. Chem. 1986, 51, 5140-5145. (b) Roussis, V.; Wu, Z.; Fenical, W.; Strobel, S. A.; Van Duyne, G. D.; Clardy, J. J. Org. Chem. 1990, 55, 4916-4922. (c) Harvis, C. A.; Burch, M. T.; Fenical, W. Tetrahedron Lett. 1988, 29, 4361-4364.
9. (a) Wratten, S. J.; Faulkner, D. J.; Hirotsu, K.; Clardy, J. Tetrahedron Lett. 1978, 4345-4348. (b) Molinski, T. F.; Faulkner, D. J.; Van Duyne, G. D.; Clardy, J. J. Org. Chem. 1987, 52, 3334-3337. (c) König, G. M.; Wright, A. D.; Angerhofer, C. K. J. Org. Chem. 1996, 61, 3259-3267. (d) Tanaka, J.; Ogawa, N.; Liang, J.; Higa, T.; Gravalos, D. G. Tetrahedron 1993, 49, 811-822. (e) Yamada, K.; Ujiie, T.; Yoshida, K.; Miyamoto, T.; Higuchi, R. Tetrahedron 1997, 53, 4569-4578.
10. (a) Wratten, S. J.; Faulkner, D. J.; Hirotsu, K.; Clardy, J. Tetrahedron Lett. 1978, 4345-4348. (b) Molinski, T. F.; Faulkner, D. J.; Van Duyne, G. D.; Clardy, J. J. Org. Chem. 1987, 52, 3334-3337. (c) König, G. M.; Wright, A. D.; Angerhofer, C. K. J. Org. Chem. 1996, 61, 3259-3267. (d) Tanaka, J.; Ogawa, N.; Liang, J.; Higa, T.; Gravalos, D. G. Tetrahedron 1993, 49, 811-822. (e) Yamada, K.; Ujiie, T.; Yoshida, K.; Miyamoto, T.; Higuchi, R. Tetrahedron 1997, 53, 4569-4578.
11. (a) Wratten, S. J.; Faulkner, D. J.; Hirotsu, K.; Clardy, J. Tetrahedron Lett. 1978, 4345-4348. (b) Molinski, T. F.; Faulkner, D. J.; Van Duyne, G. D.; Clardy, J. J. Org. Chem. 1987, 52, 3334-3337. (c) König, G. M.; Wright, A. D.; Angerhofer, C. K. J. Org. Chem. 1996, 61, 3259-3267. (d) Tanaka, J.; Ogawa, N.; Liang, J.; Higa, T.; Gravalos, D. G. Tetrahedron 1993, 49, 811-822. (e) Yamada, K.; Ujiie, T.; Yoshida, K.; Miyamoto, T.; Higuchi, R. Tetrahedron 1997, 53, 4569-4578.
12. (a) Wratten, S. J.; Faulkner, D. J.; Hirotsu, K.; Clardy, J. Tetrahedron Lett. 1978, 4345-4348. (b) Molinski, T. F.; Faulkner, D. J.; Van Duyne, G. D.; Clardy, J. J. Org. Chem. 1987, 52, 3334-3337. (c) König, G. M.; Wright, A. D.; Angerhofer, C. K. J. Org. Chem. 1996, 61, 3259-3267. (d) Tanaka, J.; Ogawa, N.; Liang, J.; Higa, T.; Gravalos, D. G. Tetrahedron 1993, 49, 811-822. (e) Yamada, K.; Ujiie, T.; Yoshida, K.; Miyamoto, T.; Higuchi, R. Tetrahedron 1997, 53, 4569-4578.
13. (a) Wratten, S. J.; Faulkner, D. J.; Hirotsu, K.; Clardy, J. Tetrahedron Lett. 1978, 4345-4348. (b) Molinski, T. F.; Faulkner, D. J.; Van Duyne, G. D.; Clardy, J. J. Org. Chem. 1987, 52, 3334-3337. (c) König, G. M.; Wright, A. D.; Angerhofer, C. K. J. Org. Chem. 1996, 61, 3259-3267. (d) Tanaka, J.; Ogawa, N.; Liang, J.; Higa, T.; Gravalos, D. G. Tetrahedron 1993, 49, 811-822. (e) Yamada, K.; Ujiie, T.; Yoshida, K.; Miyamoto, T.; Higuchi, R. Tetrahedron 1997, 53, 4569-4578.
14. 1H COSY data fully agreed only with this isomer.
15. Selected NOEs for 1: H6/H19, H14/H16, H14/H18, H2β/H3, H1/H17, H1/H2β, H14/H20, H1/H20.
16. Selected NOEs for 2. H2/H18, H5/H6, H5/H18, H6/H19, H14/H16, H14/H20, H16/H17.
17. 1H COSY couplings in 2 were observed between H2/ H18, H6/H19, H14/H16, and H14/H17.
18. + ion. Whichever way, loss of a small fragment containing both oxygen atoms is likely to occur only in structure 2.