Summary
A new norsesterterpene, hyrtial4, and known sesterterpenes,1–3, have been isolated from an anti-inflammatory active crude extract of the spongeHyrtios erecta.
This is a preview of subscription content, log in via an institution to check access.
Literatur
Myers, B.L., and Crews, P., J. org. Chem.48 (1983) 3583;
Manes, L.V., and Crews, P., Tetrahedron Lett.25 (1984) 935.
Kazlauskas, R., Murphy, P.T., Quinn, R.J., and Wells, R.J., Tetrahedron Lett. (1976) 2631;
Kashman, Y., Rudi, A., Tetrahedron33 (1977) 2997
Walker, R.P., Thompson, J.E., and Faulkner, D.J., J. org. Chem.45 (1980) 4976
Yasuda, F., and Tada, H., Experientia37 (1981) 110.
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.
Cimino, G., De Stefano, S., and Di Luccia, A., Experientia35 (1979) 1277.
Cimino, G., De Stefano, S., Minale, L., and Trivellone, E., J. chem. Soc. PerkinI (1977) 1587.
Patt, S.L., and Shoolery, J.N., J. magn. Reson.46 (1982) 535.
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).
Albericci, M., Braekman, J.C., Daloze, D., and Tursch, B., Tetrahedron38 (1982) 1881.
Author information
Authors and Affiliations
Additional information
This sponge,Hyrtios (Heteronema) erecta Keller 1889, collected in 1980/81, from Tonga was extremely abundant in the Vava'u Is. Group.
We thank Prof. R. Jacobs and his research group at UCSB for this data.
Rights and permissions
About this article
Cite this article
Crews, P., Bescansa, P. & Bakus, G.J. A non-peroxide norsesterterpene from a marine sponge Hyrtios erecta. Experientia 41, 690–691 (1985). https://doi.org/10.1007/BF02007724
Published:
Issue Date:
DOI: https://doi.org/10.1007/BF02007724