A New Cyclitol Derivative from a Sponge Stelletta Species

  • Zhao, Qingchun (College of Pharmacy, Pusan National University, Shenyang Northern Hospital) ;
  • Liu, Yong-Hong (College of Pharmacy, Pusan National University) ;
  • Hong, Jong-Ki (Korea Basic Science Institute) ;
  • Lee, Chong-O. (Korea Research Institute of Chemical Technology) ;
  • Park, Jong-Hee (College of Pharmacy, Pusan National University) ;
  • Lee, Dong-Seok (Department of Biomedical Science and Engineering, Inje University) ;
  • Jung, Jee-H. (College of Pharmacy, Pusan National University)
  • Published : 2003.03.01

Abstract

Guided by the brine shrimp lethality assay, a new (4) and three known cyclitol derivatives (1-3) were isolated from the marine sponge Stelletta sp. Norsarcotride A (4) showed significant cytotoxicity against a small panel of five human tumor cell lines.

Keywords

References

  1. Bergquist, P., Lawson, M. P., Lavis, A., and Cambie, R. C., Fatty acid composition and the classification of the Porifera. Biochem. Syst. Ecol. 12, 63-84 (1984) https://doi.org/10.1016/0305-1978(84)90012-7
  2. Costantino, V., Fattorusso, E., Imperatore, C., and Mangoni, A., Glycolipids from sponges. 11. Isocrasserides, novel glycolipids with five-membered cyclitol widely distributed in marine sponges. J. Nat. Prod. 65, 883-886 (2002) https://doi.org/10.1021/np010498y
  3. Costantino, V., Fattorusso, E., and Mangoni, A., The stereochemistry of crasserides. J. Nat. Prod. 57, 1726-1730 (1994) https://doi.org/10.1021/np50114a018
  4. Costantino, V., Fattorusso, E., and Mangoni, A., Isolation of five membered cyclitol glycolipids, crasserides: unique glycerides from the sponge Pseudoceratina crassa. J. Org. Chem. 58, 186-191(1993) https://doi.org/10.1021/jo00053a034
  5. Fusetani, N., Asai, N., Matsunaga, S., Honda, K., and Yasumuro, K., Bioactive marine metabolites. 59. Cyclostellettamines A-F, pyridine alkaloids which inhibit binding of methylquinuclidinyl benzilate (QNB) to muscarinic acetylcholine receptors, from the marine sponge, Stelletta maxima. Tetrahedron Lett. 35, 3967-3970 (1994) https://doi.org/10.1016/S0040-4039(00)76715-3
  6. Guerriero, A., Debitus, C., and Pietra, F., On the first marine stigmastane sterols and sterones having a 24,25-double bond. Isolation from the sponge Stelletta sp. of deep coral sea. Helv. Chim. Acta 74, 487-494 (1991)
  7. Hirota, H., Matsunaga, S., and Fusetani N., Bioactive marine metabolites. 32. Stellettamide A, an antifungal alkaloid from a marine sponge of the genus Stelletta. Tetrahedron Lett. 31, 4163-4164 (1990) https://doi.org/10.1016/S0040-4039(00)97570-1
  8. Ishibashi, M., Zeng, C. M., and Kobayashi, J., Keruffaride: structure revision and isolation from plural genera of Okinawan marine sponges. J. Nat. Prod. 56, 1856-1860 (1993) https://doi.org/10.1021/np50100a033
  9. Kobayashi, J., Zeng, C. M., and Ishibashi, M., Keruffaride, a new all-cis cyclopentanepentol-containing metabolite from the Okinawan marine sponge Luffariella sp. J. Chem. Soc., Chem. Commun. 79-81 (1993)
  10. Kim, D-K., Lim, Y. J, Kim, J. S., Park, J. H., Kim, N. D., Im, K. S., Hong, J., and Jung, J. H., A cyclitol derivative as a replication inhibitor from the marine sponge Petrosia sp. J. Nat. Prod. 62, 773-776 (1999) https://doi.org/10.1021/np9804785
  11. Li, H., Matsunaga, S., and Fusetani, N., Bioactive marine metabolites. 62. A new 9,11-secosterol, stellettasterol from a marine sponge Stelletta sp. Experientia 50, 771-773 (1994) https://doi.org/10.1007/BF01919380
  12. Liu, Y., Lee, C.-O., Hong, J., and Jung, J. H., Cyclitol derivatives from the sponge Sarcotragus species. Bull. Korean Chem. Soc. 23, 1467-1469 (2002) https://doi.org/10.5012/bkcs.2002.23.10.1467
  13. Matsunaga, S., Yamashita, T., Tsukamoto, S., and Fusetani, N., Three new antibacterial alkaloids from a marine sponge Stelletta species. J. Nat. Prod. 62, 1202-1204 (1999) https://doi.org/10.1021/np990161k
  14. McCabe, T., Clardy, J., Minale, L., Pizza, C., Zollo, F., and Riccio, R., A triterpenoid pigment with the isomalabricane skeleton from the marine sponge Stelletta sp. Tetrahedron Lett. 23, 3307-3310 (1982) https://doi.org/10.1016/S0040-4039(00)87601-7
  15. McCormick. J. L.. McKee. T. C., Cardellina. J. H., Leid. M., and Boyd, M. R., Cytotoxic triterpenes from a marine sponge, Stelleta sp. J. Nat. Prod. 59, 1047-1050 (1996) https://doi.org/10.1021/np960541v
  16. Miyamoto, T., Kodama, K., Aramaki, Y., Higuchi, R., and Van Soest, R, W, M., Orostanal, a novel abeo-sterol inducing apoptosis in leukemia cell from a marine sponge, Stelletta hiwasaensis. Tetrahedron Lett. 42, 6349-6351 (2002) https://doi.org/10.1016/S0040-4039(01)01278-3
  17. Nozawa, D., Takikawa, H., and Mori, K., Synthesis and absolute configuration of stellettadine A: a marine alkaloid that induces larval metamorphosis in ascidians. Bioorg. Med. Chem. Lett. 11, 1481-1483 (2001) https://doi.org/10.1016/S0960-894X(01)00015-4
  18. Oku, N., Matsunaga, S., Wada, S. I., Watabe, S., and Fusetani, N., New isomalabricane triterpenes from the marine sponge Stelletta globostellata that induce morphological changes in rat fibroblasts. J. Nat. Prod. 63, 205-209 (2000) https://doi.org/10.1021/np990333d
  19. Ryu, G., Matsunaga, S., and Fusetani, N., Globostellatic acids A-D, new cytotoxic isomalabricane triterpenes from the marine sponge Stelletta globostellata. J. Nat. Prod. 59, 512-514 (1996) https://doi.org/10.1021/np9601317
  20. Shin, J., Seo, Y., Cho, K. W., Rho, J.-R., and Sim, C. J., Stellettamide B, a new indolizidine alkaloid from a sponge of the genus Stelleta. J. Nat. Prod. 60, 611-613 (1997) https://doi.org/10.1021/np970041h
  21. Su, J. Y., Meng, Y. H., Zeng, L. M., Fu, X., and Schmitz, F. J., Stellettin A, a new triterpenoid pigment from the marine sponge Stelletta tenuis. J. Nat. Prod. 57, 1450-1451 (1994) https://doi.org/10.1021/np50112a017
  22. Tsukamoto, S., Yamashita, T., Matsunaga, S., and Fusetani, N., Bistellettadines A and B: two bioactive dimeric stellettadines from a marine sponge Stelletta sp. J. Org. Chem. 64, 3794-3795 (1999a) https://doi.org/10.1021/jo9903252
  23. Tsukamoto, S., Yamashita, T., Matsunage, S., and Fusetani, N., Bioactive marine metabolites. 89. Stellettazole A: an antibacterial guanidinoimidazole alkaloid from a marine sponge Stelletta sp. Tetrahedron Lett. 40, 737-738 (1999b) https://doi.org/10.1016/S0040-4039(98)02443-5
  24. Tsukamoto, S., Kato, H., Hirota, H., and Fusetaui, N., Stellettadine A: a new acylated bisguanidium alkaloid which induces larval metamorphosis in ascidians from a marine sponge Stelletta sp. Tetrahedron Lett. 37, 5555-5556 (1996) https://doi.org/10.1016/0040-4039(96)01154-9
  25. Yan, S. J., Su, J. Y., Zhang, G. W., Wang, Y. H., and Li, H., Ketosterols from Stelletta tenuis. Zhongshan Daxue Xuebao 40, 54-57 (2001)
  26. Zhao, Q., Lee, S.-Y., Hong, J., Lee, C.-O., Im, K. S., Sim, C. J., Lee, D. S., and Jung, J. H., New acetylenic acids from the marine sponge Stelletta species. J. Nat. Prod. (2003a), in press