Summary
A new norsesterterpene, hyrtial4, and known sesterterpenes,1–3, have been isolated from an anti-inflammatory active crude extract of the spongeHyrtios erecta.
Literatur
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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.
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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.
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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.
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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
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DOI: https://doi.org/10.1007/BF02007724