Summary
Luffariellolide (2) is a sesterterpene from the Palauan spongeLuffariella sp. that has useful anti-inflammatory properties. In contrast with the irreversible action of manoalide (1) on phospholipase A2, luffariellolide (2) is a slightly less potent but partially reversible PLA2 inhibitor.
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References
de Silva, E.D., and Scheuer, P.J., Tetrahedron Lett.21 (1980) 1611.
Jacobs, R.S., Culver, P., Langdon, R., O'Brien, T., and White, S., Tetrahedron41 (1985) 981.
Glaser, K.B., and Jacobs, R.S., Biochem. Pharm.35 (1986) 449.
Katsumura, S., Fujiwara, S., and Isoe, S., Tetrahedron Lett.26 (1985) 5827;
Garst, M.E., Tallman, E.A., Bonfiglio, J.N., Harcourt, D., Ljungwe, E.B., and Tran, A., Tetrahedron Lett.27 (1986) 4533.
Cimino, G., De Stefano, S., and Minale, L., Experientia30 (1974) 18; Sullivan, B., and Faulkner, D.J., Tetrahedron Lett.23 (1982) 907.
Luffariellolide (2): oil; UV (MeOH), 214 nm (∈ 10,000), (MeOH/OH−) 253 nm (∈ 4400); (IR (CHCl3) 3300 (br), 1760 (br) cm−1;1H NMR (CDCl3) δ0.99 (s, 6 H), 1.60 (br s, 3 H), 1.64 (br s, 6 H), 5.14 (br t, 2 H,J=7 Hz) 5.85 (br s, 1 H), 6.01 (s, 1 H);13C NMR (CDCl3) δ 171.9 (s), 169.9 (s), 136,9 (s), 136.8 (s), 136.0 (s), 126.6 (s), 123.1 (d), 121.9 (d), 119.0 (d), 117.0 (d), 99.5 (d), 40.1 (t), 39.7 (t), 39.5 (t), 34.8 (s), 32.6 (t), 28.5 (q), 27.8 (t), 27.7 (t), 26.4 (t), 24.9 (t), 19.7 (q), 19.4 (t), 16.0 (q), 15.9 (1); HRMS obsd.m/z 386.2821, C25H38O3 requires 386.281.
Yunker, M.B., and Scheuer, P.J., J. Am. chem. Soc.100 (1978) 307.
Roll, D.M., and Ireland, C.M., personal communication.
T/C-1 measures the increase in weight of treated ear tissue compared with the same area of control ear tissue.
p<0.05, Students t-test.
Glaser, K.B., and Jacobs, R.S., Fedn Proc.45 (1986) 580, and Biochem. Pharmac., in press.
Full details of the pharmacology of luffariellolide will be presented elsewhere (Glaser, K.B., Ph.D. Thesis, University of California, Santa Barbara).
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30 December 1986
Acknowledgment We thank Edward Luedtke, Elise Clason and Ellen Snideman for performing some of the assays reported above. The sponge was identified by Dr. Klaus Rützler, Smithsonian Institution, Washington, D.C. The research was supported by grants from Allergan Pharmaceuticals and the California Sea Grant College Program (Projects R/MP-30 and R/MP-31).
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Albizati, K.F., Holman, T., Faulkner, D.J. et al. Luffariellolide, an anti-inflammatory sesterterpene from the marine spongeLuffariella sp.. Experientia 43, 949–950 (1987). https://doi.org/10.1007/BF01951682
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DOI: https://doi.org/10.1007/BF01951682