Cell Cycle Regulation and Antioxidant Activity of Psammaplin A, A Natural Phenolic Compound from Marine Sponge

  • Jiang, Ya-Hong (School of Pharmaceutical Engineering, Shenyang Pharmaceutical University) ;
  • Ryu, Seung-Hee (Department of Chemistry and Biohealth Products Research Center, Inje University) ;
  • Ahn, Eun-Young (Department of Chemistry and Biohealth Products Research Center, Inje University) ;
  • You, Song (School of Pharmaceutical Engineering, Shenyang Pharmaceutical University) ;
  • Lee, Burm-Jong (Department of Chemistry and Biohealth Products Research Center, Inje University) ;
  • Jung, Jee-H (College of Pharmacy, Pusan National University) ;
  • Kim, Dong-Kyoo (Department of Chemistry and Biohealth Products Research Center, Inje University)
  • Published : 2004.12.30

Abstract

Psammaplin A (PSA), a naturally occurring biophenolic compound has been demonstrated to deliver significant cytotoxicity to many cancer cell lines. In this article, we investigated the effect of PSA on cell cycle progression of lung cancer cells (A549). It was found that PSA could slightly perturb the cell cycle progression of A549 cells and lead to the cell cycle arrest at G2/M phase, indicating PSA might disturb the mitosis process of A549 cells. In addition, inspired by the two phenolic groups in the structure of PSA, the antioxidant activity of it has been evaluated. Although PSA was weak in scavenging the stable free radical 1,1-diphenyl-2-picrylhyrazyl (DPPH), it showed stronger ABTS radical scavenging activity than ascorbic acid in TEAC assay. Furthermore, it was found that PSA could effectively prevent DNA strand scission induced by oxidative stress. These results suggest that PSA have both cell cycle regulation and antioxidant activities. Herein, we suggest that PSA would be a very interesting and promising candidate to be developed as a multi-function drug.

Keywords

References

  1. Adams, J.D. and Odunze, I.N., Oxygen free radicals and Parkinson disease. Free Radie. BioI. Med. 10,161-169 (1991) https://doi.org/10.1016/0891-5849(91)90009-R
  2. Arabshahi, L. and Schmitz, F.J., Brominated tyrosine metabolites from an unidentified sponge. J. Org. Chern. 52, 3584-3586 (1987) https://doi.org/10.1021/jo00392a016
  3. Block, K.I, Antioxidants and cancer therapy: Furthering the debate. Integr Cancer Ther. 3, 342-348 (2004) https://doi.org/10.1177/1534735404272152
  4. Blois, M.S., Antioxidant determinations by the use of a stable free radical. Nature 181, 1199-1200 (1958) https://doi.org/10.1038/1811199a0
  5. Borek, C., Dietary antioxidants and human cancer. Integr Cancer Ther. 3, 333-341 (2004) https://doi.org/10.1177/1534735404270578
  6. Briviba, K and Sies, H., Nonenzymatic antioxidant defense systems, in Frei, B. (eds.), Natural Antioxidants in Human Health and Disease, Academic Press, New York, 1994, pp. 107-128
  7. Cerutti, P, Oxy-radicals and cancer. Lancet. 344, 862-863 (1994) https://doi.org/10.1016/S0140-6736(94)92832-0
  8. Clement, M.V., Hirpara, J.L., Chawdhury, S.H., and Pervaiz, S., Chemopreventive agent resveratrol, a natural product derived from grapes, triggers CD95 signaling-dependent apoptosis in human tumor cells. Blood. 92, 996-1002 (1998)
  9. Cottelle, N., Bernier, J.L., Catteau, J.P., Pommery, P., Wallet, J.C., and Gadou, E.M., Antioxidant propelties of hydroxyl-flavones. Free Radic. BioI. Med. 20, 35-43 (1996) https://doi.org/10.1016/0891-5849(95)02014-4
  10. Decker, E.A, The role of phenolics, conjugated linoleic acid, carnosine and pyrroloquinoline quinone as nonessential dietary antioxidants. Nutr: Rev. 53, 49-58 (1995) https://doi.org/10.1111/j.1753-4887.1995.tb01502.x
  11. Hertog, M.G.L., Feskens, E.J.M., Hollman, P.C.H., Katan, M.B., and Kromhout, D., Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen elderly study. Lancet. 342, 1007-1011 (1993) https://doi.org/10.1016/0140-6736(93)92876-U
  12. Hideyuki, T., Munetaka, I., Fumio, O., Kazumi, S., Tomoyuki, H., Keiji, S., and Masami W., A water-soluble tetrazolium salt useful for colorimetric cell viability assay. Anal. Cornrnun. 36, 47-50 (1999) https://doi.org/10.1039/a809656b
  13. Jiang, Y.H., Ahn, E.Y, Ryu, S.H., Kim, D.K, Park, J.S., Yoon, H.J., You, S., Lee, B.J., Lee, D.S., and Jung, J.H., Cytotoxicity of psammaplin A from a two-sponge association may correlate with the inhibition of DNA replication. BMC Cancer 4, 70 (2004) https://doi.org/10.1186/1471-2407-4-70
  14. Ju, E.M., Lee, S.F., Hwang, H.J., and Kim, J.H., Antioxidant and anticancer activity of extract from Betula platyphylla var. japonica. Life Sci. 74, 1013-1026 (2004) https://doi.org/10.1016/j.lfs.2003.07.025
  15. Keum, Y.S., Park, K.K, Lee, lM., Chun, KS., Park, J.H., Lee, S.K, Kwon, H., and Surh, Y.J., Antioxidant and anti-tumor promoting activities of the methanol extract of heat-processed ginseng. Cancer Lett. 150, 41-48 (2000) https://doi.org/10.1016/S0304-3835(99)00369-9
  16. Kim, D., Lee, I.S., Jung, J.H., and Yang, S.H., Psammaplin A, a natural bromotyrosine derivative trom a sponge, possesses the antibacterial activity against Methicillin-resistant Staphyloco ccusa ureus and the DNA gyrase-inhibitory activity. Arch. Phann. Res. 22, 25-29 (1999) https://doi.org/10.1007/BF02976431
  17. Lien, E.J., Ren, S., Bui, H.H., and Wang, R., Quantitative structure-activity relationship analysis of phenolic antioxidants. Free Radic. BioI. Med. 26, 285-294 (1999) https://doi.org/10.1016/S0891-5849(98)00190-7
  18. Mitchell, J.H., Gardner, PT., McPhail, D.B., Morrice, PC., Collins, AR., and Duthie, G.G., Antioxidant efficacy of phytoestrogens in chemical and biological model system. Arch. Biochern. Biophys. 360,142-148 (1998) https://doi.org/10.1006/abbi.1998.0951
  19. Nicolaou, KC., Houghes, R., Pfefferkorn, J.A, and Barluenga, S., Optimization and mechanistic studies of psammaplin A type antibacterial agents active against methicillin-resistant Staphy lococcus aureus (MRSA). Chem. Eur. J. 7, 4296-4310 (2001a) https://doi.org/10.1002/1521-3765(20011001)7:19<4296::AID-CHEM4296>3.0.CO;2-2
  20. Nicolaou, K.C., Houghes, R., Pfefferkorn, J.A, Barluenga, S., and Roeker, A,J., Combinatorial synthesis through disulfide exchange: discovery of potent psanunaplin A type antibacterial agents active against Methicillin-Resistant Staphylococcus aureus (MRSA). Chem. Eur. J. 7,4280-4295 (2001b) https://doi.org/10.1002/1521-3765(20011001)7:19<4280::AID-CHEM4280>3.0.CO;2-3
  21. Pina, I.C., Gautschi J.T., Wang, G.Y.S., Sanders, M.L., Schmitz, FJ., France, D., Kennon, S.C., Sarnbucetti, L.C., Remiszewski, S.W., Perez, L.B., Bair, K.W., and Crews, P, Psammaplins from the sponge pseudocerutina purpurea: Inhibition of both histone deacetylase and DNA methyltransferase. J. Org. Chern. 68, 3866-3873 (2003) https://doi.org/10.1021/jo034248t
  22. Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., and Rice-Evans, C., Antioxidant activity applying an improved ABTS radical cation decolorized assay. Free Radic. Biol. Med. 26, 1231-1237 (1999) https://doi.org/10.1016/S0891-5849(98)00315-3
  23. Russo, A., Acquaviva, R., Campisi, A., Sorrenti, v., Di-Giacomo, C., Vtrgata, G., Barcellona, ML, and Vanella, A., Bioflavonoids as antiradicals, antioxidants and DNA cleavage protectors. Cell Biol. Toxicol. 16, 91-98 (2000) https://doi.org/10.1023/A:1007685909018
  24. Sanchez-Moreno, C., Larrauri, J.A., and Saura-Calixto, F, Free radical scavenging capacity and inhibition of lipid oxidation of wines, grape juices and related polyphenolic constituents. Food Res. Int. 32, 407-412 (1999) https://doi.org/10.1016/S0963-9969(99)00097-6
  25. Stoner, G.D. and Mukhtar, H., Polyphenols as cancer chemopre ventive agents. J Cell Biochem Suppl. 22, 169-80 (1995)