Isolation and synthesis of the first natural 6-hydroximino 4-en-3-one-steroids from the sponge Cinachyrella spp.

Tetrahedron Letters

Volumn 38, Issue 10, 1997, Pages 1833-1836

  Rodríguez, Jaime ^a   Nuñez, Lucia ^a   Peixinho, Solange ^b   Jiménez, Carlos ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

^b FEDERAL UNIVERSITY OF BAHIA   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

STEROID;

ARTICLE; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPONGE; STEREOISOMERISM;

EID: 0031562390     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00163-9     Document Type: Article

References (11)

1. 1. Faulkner, D. J. Nat. Prod. Rep., 1996, 13, 75-125 and references therein.
2. 2. Barnathan, G.; Miralles, J.; Njinkou, J. M.; Mangoni, A.; Fattonisso, F.; Debitus; C. Boury-Esnault, N.; Kornprobost, J. M. Comp. Biochem. Physiol. 1992, 103B, 1043-1047.
3. 3. Two morphospecies from Pituba Beach (Salvador) presented the same variation of external morphology and only few differences in spicular characters were found. C. alloclada have one size class of tetractines whereas C. apion have two raphids as microscleres.
4. 4. In a second study we also detected the presence of these three compounds on individual specimens of Cinachyrella alloclada and C. apion collected at the same place.
5. 1H NMR Spectra Ed. I. Spectrum 3, 578B, 1993. This compound was first encountered in the sponge Stelleta clarella: Sheikh, Y. M.; Djerassi, C. Tetrahedron, 1974, 30 , 4095-4103.
6. 1H NMR Spectra Ed. I. Spectrum 3, 578B, 1993. This compound was first encountered in the sponge Stelleta clarella: Sheikh, Y. M.; Djerassi, C. Tetrahedron, 1974, 30 , 4095-4103.
7. +, 100).
8. 7. This was deduced by the appearance of the signals at δ 6.13 ppm (s) and 2.55 (m) assignable to H-4 and H-7β of the Z isomer. The conversion of (E)-cholest-4-en-6-hydroximino to its Z isomer in MeOH under irradiation is known: Suginome, H.; Ohshima, K.; Ohue, Y.; Onki, T.; Senboku, H. J. Chem. Soc. Perton Trans. 1, 1994, 3239-3249.
9. 8. Holland, H. L.; Kumaresan, S.; Tan, L.; Njar, V. C. O. J. Chem. Soc. Perkin Trans. 1, 1992, 585-587.
10. 13C-NMR see Table 1. EIMS m/z (%): 413 (14), 396 (30), 370 (80), 174 (45), 125 (70), 55 (100).
11. 10. Aiello, A.; Fattonisso, E.; Magno, S.; Menna, M.; Pansini, M. J. Nat. Prod., 1993, 54, 281-285.