DOI: 10.1039/A604271F
(Paper)
Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 959-962
Juncins G and H: new briarane diterpenoids of the Indian Ocean gorgonian Junceella juncea Pallas
(Note: The full text of this document is currently only available in the PDF Version )
Ammanamanchi S. R. Anjaneyulu and Nidasanametla S. Kameswara Rao
Abstract
Chemical examination of the Indian Ocean gorgonian, Junceella juncea furnishes two new diterpenoids of the briarane skeleton, juncin G, 1 and juncin H, 3 along with the antipodal derivatives of known gemmacolides A, 4 and B, 2. The structures of juncin H and G are shown to be (1S,2S,6S,8R,9S,10S ,11R,12R,14R,17R)-6-chloro-11, 20-epoxy-14-(3-methylbutanoyl)-2,9,12-triacetoxy-8-hydroxybriar-5(16)-e n-18,7-olide and (1S,2S,6S,9S,10S,12R ,13R,14R)-6-chloro-13-(3-methylbutanoyl)-2,9,12, 14-tetraacetoxybriaran-4,8(17)-dien-18,7-olide, respectively, by a comparative study of their spectral data. For the first time, three polyhydroxy sterols 6–8 are also isolated from this species.
References
- D. J. Faulkner, Nat. Prod. Rep., 1995, 12, 223 RSC and earlier reviews in this series and references cited therein.
- I. Wahlberg and A.-M. Eklund, Fortschr. Chem. Org. Naturst., 1992, 60, 1 Search PubMed.
- S. Issacs, S. Carmely and Y. Kashman, J. Nat. Prod., 1990, 53, 596.
- A. D. Rodriguez, C. Ramirez and O. M. Cobar, J. Nat. Prod., 1996, 50, 15 CrossRef CAS.
- A. S. R. Anjaneyulu, G. Venkateswara Rao and C. V. S. Prakash, Indian J. Chem., Sect. B, 1994, 33, 1165; A. S. R. Anjaneyulu, K. V. S. Raju and G. Venkateswara Rao, Indian J. Chem., Sect. B, 1995, 34, 666; A. S. R. Anjaneyulu, G. Venkateswara Rao and N. S. Kameswara Rao, Indian J. Chem., Sect. B, 1996, 35, 815; A. S. R. Anjaneyulu, K. V. S. Raju and C. V. S. Prakash, Nat. Prod. Lett., 1993, 3, 149 Search PubMed; A. S. R. Anjaneyulu and K. S. Sagar, J. Chem. Res., 1995, (S), 142 Search PubMed; A. S. R. Anjaneyulu, K. S. Sagar and M. J. R. V. Venugopal, Tetrahedron, 1995, 51, 10 997 CrossRef CAS; A. S. R. Anjaneyulu, M. J. R. V. Venugopal and N. S. Kameswara Rao, J. Chem. Res., 1996, (S) Search PubMed.
- Hai-Yin He and D. J. Faulkner, Tetrahedron, 1991, 47, 3271 CrossRef CAS.
- R. W. Dunlop and R. J. Wells, Aust. J. Chem., 1979, 32, 1345 CAS.
- (a) M. Kobayashi, T. Hayashi, F. Nakajima and H. Mitsuhashi, Steroids, 1979, 34, 285 CrossRef CAS; (b) M. Kobayashi, T. Hayashi, K. Hayashi, M. Tanabe, T. Nakagawa and H. Mitsuhashi, Chem. Pharm. Bull., 1983, 31, 1848 CAS; (c) M. Kobayashi and H. Mitsuhashi, Chem. Pharm. Bull, 1983, 31, 4127 CAS.
- V. Picciali and D. Sica, J. Nat. Prod., 1987, 50, 915.
- C. B. S. Rao, K. V. Ramana and D. Venkata Rao, J. Nat. Prod., 1988, 51, 954 CrossRef CAS.