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Cytotoxic Effects of Furanosesterterpenes, Cyclitol Derivatives, and Bromotyrosine Derivative Isolated from Marine Sponges

  • 발행 : 2005.09.01

초록

Marine sponges are known to produce a number of cytotoxic secondary metabolites. In the course of searching for cytotoxic metabolites from marine organisms, we have evaluated cytotoxic activities of six marine secondary metabolites isolated from various sponges. The cytotoxic compounds 1-6 were isolated by the application of various chromatographic methods, including column chromatography and HPLC. The molecular structures were mostly determined using mass spectrometry (MS) and Nuclear Magnetic Resonance (NMR) Spectroscopy. Furanosestererpenes (compounds 1-3) from Psammocinia sp., cyclitol derivatives (compounds 4 and 5) from Sarcotragus sp., and bromotyrosine-type compound (6) from an association of two sponges Jaspis wondoensis and Poecillastra wondoensis were evaluated for their cytotoxic activity against three cancer cell lines; Hep G2, HeLa, and MCF-7. All tested compounds exhibited cyctoxicity at concentrations ranging from $5\;\mug/mL\;to\;25\;\mug/mL.$ Particularly, among the tested compounds, compound 6 showed the highest potency displaying at least $80\%$ of cytotoxicity at $5\;\mug/mL$ level against all three cancer cell lines.

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참고문헌

  1. Ajith TA, Janardhanan KK. 2003. Cytotoxic and antitumor activities of a polypore macrofungus, Phellinus rimosus (Berk) Pilat. J Ethnopharmacol 84: 157-162 https://doi.org/10.1016/S0378-8741(02)00292-1
  2. Haefner B. 2003. Drugs from the deep: marine natural products as drug candidates. Drug Discov Today 8: 536-544 https://doi.org/10.1016/S1359-6446(03)02713-2
  3. Newman DJ, Gordon MC. 2004. Marine natural products and related compounds in clinical and advanced preclinical trials. J Nat Prod 67: 1216-1238 https://doi.org/10.1021/np040031y
  4. Proksch P. 1994. Defensive roles for secondary metabolites from marine sponges and sponge-feeding nudibranchs. Toxicon 32: 639-655 https://doi.org/10.1016/0041-0101(94)90334-4
  5. Faulkner DJ. 1998. Marine natural products. Nat Prod Rep 15: 113-158 https://doi.org/10.1039/a815113y
  6. Proksch P, Edrada RA, Ebel R. 2002. Drugs from the seas-current status and microbiological implications. Appl Microbiol Biotechnol 59: 125-134 https://doi.org/10.1007/s00253-002-1006-8
  7. Belarbi EH, Gomez AC, Chisti Y, Camacho FG, Grima EM. 2003. Producing drugs from marine sponges. Biotechnol Adv 21: 585-598 https://doi.org/10.1016/S0734-9750(03)00100-9
  8. Choi K, Hong J, Lee CO, Kim DK, Sim CJ, Im KS, Jung JH. 2004. Cytotoxic furanosesterterpenes from a marine sponge Psammocinia sp. J Nat Prod 67: 1186-1189 https://doi.org/10.1021/np049922w
  9. Liu Y, Lee CO, Hong J, Jung JH. 2002. Cyclitol derivatives from the sponge Sarcotragus species. Bull Korean Chem Soc 23: 1467-1469 https://doi.org/10.5012/bkcs.2002.23.10.1467
  10. Park Y, Liu Y, Hong J, Lee CO, Cho H, Kim DK, Im KS, Jung JH. 2003. New bromotyrosine derivatives from an association of two sponges, Jaspis wondoensis and Poecillastra wondoensis. J Nat Prod 66: 1495-1498 https://doi.org/10.1021/np030162j
  11. Liu Y, Bae BH, Alam N, Hong J, Sim CJ, Lee CO, Im KS, Jung JH. 2001. New cytotoxic sesterterpenes from the sponge Sarcotragus species. J Nat Prod 64: 1301-1304 https://doi.org/10.1021/np0101494
  12. Carmichael J, DeGraff WG, Gazdar AF, Minna JD, Mitchell JB. 1987. Evaluation of a tetrazolium-based semiautomated colorimetric assay: assessment of chemosensitivity testing. Cancer Res 47: 936-942
  13. Liu Y, Hong J, Lee CO, Im KS, Kim ND, Choi JS, Jung JH. 2002. Cytotoxic pyrrolo and furanoterpenoids from the sponge Sarcotragus species. J Nat Prod 65: 1307-1314 https://doi.org/10.1021/np020145e
  14. Liu Y, Mansoor TA, Hong J, Lee CO, Sim CJ, Im KS, Kim ND, Jung JH. 2003. New cytotoxic sesterterpenoids and norsesterterpenoids from two sponges of the genus Sarcotragus. J Nat Prod 66: 1451-1456 https://doi.org/10.1021/np030268e
  15. Costantino V, Fattorusso E, Mangoni A. 1993. Isolation of five-membered cyclitol glycolipids, crasserides: unique glycerides from the sponge Pseudoceratina crassa. J Org Chem 58: 186-191 https://doi.org/10.1021/jo00053a034
  16. Costantino V, Fattorusso E, Mangoni A. 1994. The stereochemistry of crasserides. J Nat Prod 57: 1726-1730 https://doi.org/10.1021/np50114a018
  17. Ishibashi M, Zeng CM, Kobayashi J. 1993. Keruffaride: structure revision and isolation from plural genera of Okinawan marine sponges. J Nat Prod 56: 1856-1860 https://doi.org/10.1021/np50100a033
  18. Kim D-K, Lim YJ, Kim JS, Park .JH, Kim ND, Im KS, Hong J, Jung JH. 1999. A cyclitol derivative as a replication inhibitor from the marine sponge Petrosia sp. J Nat Prod 62: 773-776 https://doi.org/10.1021/np9804785
  19. Rodriguez AD, Akee RK, Scheuer PJ. 1987. Two bromotyrosine-cysteine derived metabolites from a sponge. Tetrahedron Lett 28: 4989-4992 https://doi.org/10.1016/S0040-4039(00)96677-2
  20. Quinoa E, Crews P. 1987. Phenolic constituents of Psammaplysilla. Tetrahedron Lett 28: 3229-3232 https://doi.org/10.1016/S0040-4039(00)95478-9
  21. Kim D, Lee IS, Jung JH, Lee CO, Choi SU. 1999. Psammaplin A, a natural phenolic compound, has inhibitory effect on human topoisomerase II and is cytotoxic to cancer cells. Anticancer Res 19 (5B): 4085-4090
  22. Jiang Y, Ahn EY, Ryu SH, Kim DK, Park JS, Yoon HJ, You S, Lee BJ, Lee DS, Jung JH. 2004. Cytotoxicity of psammaplin A from a two-sponge association may correlate with the inhibition of DNA replication. BMC Cancer 30: 70