Advertisement

Experientia

, Volume 41, Issue 5, pp 690–691 | Cite as

A non-peroxide norsesterterpene from a marine spongeHyrtios erecta

  • P. Crews
  • P. Bescansa
  • G. J. Bakus
Short Communications Ethology, Ecology, Natural Product Chemistry

Summary

A new norsesterterpene, hyrtial4, and known sesterterpenes,1–3, have been isolated from an anti-inflammatory active crude extract of the spongeHyrtios erecta.

Key words

Sponge, marine Hyrtios erecta norsesterterpene sesterterpenes hyrtial 

Literatur

  1. 1 a).
    Myers, B.L., and Crews, P., J. org. Chem.48 (1983) 3583;CrossRefGoogle Scholar
  2. 1 b).
    Manes, L.V., and Crews, P., Tetrahedron Lett.25 (1984) 935.CrossRefGoogle Scholar
  3. 3a).
    Kazlauskas, R., Murphy, P.T., Quinn, R.J., and Wells, R.J., Tetrahedron Lett. (1976) 2631;Google Scholar
  4. 3b).
    Kashman, Y., Rudi, A., Tetrahedron33 (1977) 2997CrossRefGoogle Scholar
  5. 3c).
    Walker, R.P., Thompson, J.E., and Faulkner, D.J., J. org. Chem.45 (1980) 4976CrossRefGoogle Scholar
  6. 3d).
    Yasuda, F., and Tada, H., Experientia37 (1981) 110.CrossRefPubMedGoogle Scholar
  7. 4.
    4: mass spectrum: m/z=340(M+−HOAc), 325, 205, 191.13C-NMR (C6D6): 40.0(C-1); 18.9(C-2 or C-6); 42.5(C-3); 33.5(C-4); 56.5(C-5); 18.5(C-6) or C-2); 41.3(C-7); 37.1(C-8 or C-13); 58.2(C-9); 38,4(C-10); 23.9(C-11); 82.7(C-12); 37.7(C-13) or C-8); 52.1(C-14); 23.9(C-15); 148.6(C-16); 139.6(C-17); 30.2(C-18); 33.5(C-19); 20.1(C-20); 16.7(C-21); 16.9(C-22); 14.7(C-23); 192.8(C-4), 170.2, 21.6 (OAc). Proton NMR (C6D6, 360 MHz): 9.34 (s, H-24), 6.06 (m, w1/2=8 Hz, H-16), 4.70 (dd, J=11.1, 4.2, H-12), 2.68(d, J=17.4, H-18a); 1.90(d, J=17.4, H-18b, observed by difference decoupling); 1.68 (s, OAc), 0.87, 0.78, 0.76, 0.70, 0.67 (s,s,s,s,s, Me-19,20,21,22,23), 0.62 (dd, J=12.7, 3.4, H-5), 0.56 (dd J=11.9,3.4, H-9), 0.53 (dd, J=12.7, 4.7, H-14) but H-5,9,14 can be switched.Google Scholar
  8. 5.
    Cimino, G., De Stefano, S., and Di Luccia, A., Experientia35 (1979) 1277.CrossRefGoogle Scholar
  9. 6.
    Cimino, G., De Stefano, S., Minale, L., and Trivellone, E., J. chem. Soc. PerkinI (1977) 1587.CrossRefGoogle Scholar
  10. 7.
    Patt, S.L., and Shoolery, J.N., J. magn. Reson.46 (1982) 535.Google Scholar
  11. 8.
    Methyl stereochemistry in1–4 was established from C-13 NMR data. Podocarpanes and kauranes, in: Wehrli, F.W., and Nishida, T., Prog. Chem. org. nat. Prod.36 (1979) 2;provided base values to which were added substituent increments, in: Crews, P., and Kho-wiseman, E., Tetrahedron Lett. (1978) 2483. For example, in4 an ax Me-23 is clear by comparing experimental 14.7 to calculated values: Me(ax)=δ14, Me(q)=20. Also, in1a an equatorial C-18 substituent is clear by comparing experimental Me-29 (δ8.7) to calculated values where R-18 is ax (14), or eq (9).Google Scholar
  12. 10.
    Albericci, M., Braekman, J.C., Daloze, D., and Tursch, B., Tetrahedron38 (1982) 1881.CrossRefGoogle Scholar

Copyright information

© Birkhäuser Verlag 1985

Authors and Affiliations

  • P. Crews
    • 1
    • 2
  • P. Bescansa
    • 1
    • 2
  • G. J. Bakus
    • 1
    • 2
  1. 1.Thimann Laboratories and Center for Marine StudiesUniversity of CaliforniaSanta CruzUSA
  2. 2.Allan Hancock FoundationUniversity of Southern CaliforniaLos AngelesUSA

Personalised recommendations