Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

A New Sphingosine from a Marine Sponge Haliclona (Reniera) sp.

  • Published : 2007.09.30
Download PDF
⟨ Previous Next ⟩

Abstract

A new sphingosine (1) was isolated from the MeOH extract of a marine sponge Haliclona (Reniera) sp. by bioactivity-guided fractionation. The 1D and 2D NMR, and MS spectroscopic analyses were used to establish the planar structure of 1. The stereochemistry of the compound was defined on the basis of modified Mosher's method, comparison of optical rotation and NMR data with those of the reported. Compound 1 was mildly cytotoxic to a panel of five human solid tumor cell lines.

Keywords

References

  1. Devijver, C., Salmoun, M., Daloze, D., Braekman, J.C., Weerdt, W.H.D., Kluijver, M.J.D., and Gomez, R., (2R,3R,7Z)-20-Aminotetradec-7- ene-1,3-diol, a new amino alcohol from the Caribbean sponge Haliclona vansoesti. J. Nat. Prod. 63, 978-980 (1985) https://doi.org/10.1021/np000081c
  2. Elenkov, I., Popov, S., and Andreev, S., Sterols from two Black Sea sponges (Haliclona Sp.). Comp. Biochem. Phys. Part B: Biochem. Molec. Biology. 123, 357-360 (1999) https://doi.org/10.1016/S0305-0491(99)00079-6
  3. Enders, D. and Müller-Hüwen, A., Asymmetric synthesis of 2-amino-1,3- diols and D-erythro-sphinganine. Eur. J. Org. Chem. 2004, 1732-1739 (2004) https://doi.org/10.1002/ejoc.200300788
  4. Gulavita, N.K. and Scheuer, P.J., Two epimeric aliphatic amino alcohols from a sponge Xestospongia sp. J. Org. Chem. J. Org. Chem. 54, 366- 369 (1989) https://doi.org/10.1021/jo00263a019
  5. Mansoor, T.A., Bae, B.H., Hong, J., Lee C., Im, K.S., and Jung, J.H., New fatty acid derivatives from Homaxinella sp., a marine sponge. Lipids 40, 981-985 (2005) https://doi.org/10.1007/s11745-005-1459-0
  6. Mansoor, T.A., Hong, J., Lee, C., Sim, C.J., Son, B.W., and Jung, J.H., Renierasides, new cerebrosides from a marine sponge Haliclona (Reniera) sp. J. Nat. Prod. Submitted (2007)
  7. Li, S., Wilson, W.K., and Schroepfer, Jr. G.J., Chemical synthesis of Dribo- phytosphingosine-1-phosphate, a potential modulator of cellular processes. J. Lipid Res. 40, 117-125 (1999)
  8. Luo, X., Li, F., Shinde, P.B., Hong, J., Lee, C., Im, K.S., and Jung, J.H., 26,27-Cyclosterols and other polyoxygenated sterols from a marine sponge Topsentia sp. J. Nat. Prod. 69, 1760-1768 (2006) https://doi.org/10.1021/np0604026
  9. Santalova, E.A., Makrieva, T.N., Gorshkova, I.A., Dmitrenok, A.S., Krasokhin, V.B., and Stonik, V.A., Sterols from six marine sponges. Biochem. Biochem. Sys. Ecol. 32, 153-167 (2004) https://doi.org/10.1016/S0305-1978(03)00143-1
  10. Seldes, A.M., Rovirosa, J., San, M.A., and Gros, E.G., Sterols from the sponge Haliclona chilensis. Comp. Biochem. Phys. Part B: Biochem. Molec. Biology 81, 119-122 (1985) https://doi.org/10.1016/0305-0491(85)90171-3
  11. Sheikh, Y.M. and Djerassi, C., Steroids from sponges. Tetrahedron. 30, 4095-4103 (1974) https://doi.org/10.1016/S0040-4020(01)97391-0
  12. Rovirosa, J., Vasques, M.D.L.L., and San-Martin A., Chemotaxonomic considerations in relation to sponges of the genera Reniera and Haliclona. Biochem. Sys. Ecol. 18, 53-55 (1990) https://doi.org/10.1016/0305-1978(90)90034-D
  13. Zielinski, J., Milkova, T., Popov, S., Marekov, N., and Djerassi, C., Minor and trace sterols in marine invertebrates 34. Isolation and structure elucidation of 24-methyl-5$\alpha$-cholesta-7,9(11),24(28)-trien-3$\beta$-ol, the first naturally occurring ${\Delta}^{7,9(11)}$ unsaturated marine sterol. Steroids 39, 675-680 (1982) https://doi.org/10.1016/0039-128X(82)90138-6