Antioxidants and Inhibitor of Matrix Metalloproteinase-1 Expression from Leaves of Zostera marina L

  • Published : 2004.02.01

Abstract

In order to develop new anti-photoaging agents, we examined the antioxidative activity and the inhibition effect of matrix metalloproteinase-1 (MMP-1) on the extracts of a marine product, Zostera marina L., which is known for its potent activity. Three compounds (compounds 1, 2, and 3) were isolated from an ethyl acetate (EtOAc) soluble fraction of the product; they were identified as apigenin-7 -O-$\beta$-D-glucoside (1), chrysoeriol (2), and luteolin (3). These compounds were found to scavenge radicals and reactive oxygen species (ROS) and were measured to have $SC_{50}$/ values of 0.18 mM, 0.68 mM, and 0.01 mM against the 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical and 0.04 mM, 0.03 mM, and 0.01 mM against the superoxide radical in the xanthine/xanthine oxidase system, respectively. Compound 3 suppressed the expression of MMP-1 by up to 44% at 4.0 $\mu$M and inhibited the production of interleukin 6 (IL-6), which is known as a cytokine that induces MMP-1 expression. From these results, compound 3 and the other compounds were determined to have antioxidative activity and to inhibit MMP-1 expression. Thus, the three compounds are expected to be useful for preventing the photoaging of skin.

Keywords

References

  1. Bauer, E. A., Seltzer, J. L., and Eisen, A. Z., Retinoic acid inhibition of collagenase and gelatinase expression in human skin fibroblast cultures. Evidence for a dual mechanism. J. Invest. Dermatol., 81, 162-169 (1983) https://doi.org/10.1111/1523-1747.ep12543590
  2. Blois, M. S., Antioxidant determinations. by the use of a stable free radical. Nature, 181, 1199-1200 (1958) https://doi.org/10.1038/1811199a0
  3. Brenneisen, P., Wenk, T., Klotz, L. O., Wlaschek, M., Brivida, K., Krieg, T., Sies, H., and Scharffetter-Kochanek, K., Central role of ferrous/ferric iron in the ultraviolet B irradiation-mediated signaling pathway leading to increased interstitial collagenase (matrix-degrading metalloprotease (MMP)-1) and stromelysin-1 (MMP-3) mRNA levels in cultured human dermal fibroblasts. J. Biol. Chem., 273, 5279-5287 (1998) https://doi.org/10.1074/jbc.273.9.5279
  4. Brieskorn, V. C. H. and Riedel, W., Flavonoids from coleus amboinicus. Planta Medica, 31,308-310 (1977). https://doi.org/10.1055/s-0028-1097537
  5. Chi, Y. S., Heo, M. Y, Chung, J. H., Jo, B. K., and Kim, H. P., Effects of the chestnut inner shell extract on the expression of adhesion molecules, fibronectin and vitronectin, of skin fibroblasts in culture. Arch. Pharm. Res., 25, 469-474 (2002) https://doi.org/10.1007/BF02976604
  6. Dunsmore, S. E., Rubin, J. S., Kovacs, S. O., Chedid, M., Parks, W. C., and Welgus, H. G., Mechanisms of hepatocyte growth factor stimulation of keratinocyte metalloproteinase production. J. Biol. Chem., 271, 24576-24582 (1996) https://doi.org/10.1074/jbc.271.40.24576
  7. Ersoz, T., Harput, U. S., Saracoglu, I., CaliS, I., and Ogihara, Y., Phenolic compounds from Scutellaria pontica. Turk. J. Chem., 26, 581-588 (2002)
  8. Fisher, G. J., Datta, S. C., Talwar, H. S., Wang, Z., Varanl, J., Kang, S. W., and Voorhees, J. J., Molecular basis of sun-induced premature skin ageing and retinoid antagonism. Nature, 379, 335-339 (1996) https://doi.org/10.1038/379335a0
  9. Fisher, G. J., Wang, Z., Datta, S. C., Varani, J., Kang, S. w., and Voorhees, J. J., Pathophysiology of premature skin aging induced by ultraviolet light. N. Engl. J. Med., 337,1419-1428 (1997) https://doi.org/10.1056/NEJM199711133372003
  10. Fisher, G. J., Datta, S. C., Wang, Z., Li, X., Quan, T., Chunh, J. H., Kang, S. W., and Voorhees, J. J., c-Jundependent inhibition of cutaneous procollagen transcription following ultraviolet irradiation is reversed by all-trans retinoic acid. J. Clin. Invest., 106, 663-670 (2000) https://doi.org/10.1172/JCI9362
  11. Furuno, K., Akasako, T., and Sugihara, N., The contribution of the pyrogallol moiety to the superoxide radical scaveng-ing activity of flavonoids. Biol. Pharm. Bull., 25, 19-23 (2002) https://doi.org/10.1248/bpb.25.19
  12. Gilchrest, B. A., Garmyn, M., and Yaar, M., Aging and photoaging affect gene expression in cultured human keratinocytes. Arch. Dermatol., 130,82-86 (1994) https://doi.org/10.1001/archderm.130.1.82
  13. Girotti, A. W., Lipid hydroperoxide generation, turnover, and effector action in biological systems. J. Lipid Res., 39, 1529-1542 (1998)
  14. Greul, A. K., Grundmann, J. U., Heinrich, F., Pfitzner, I., Bernhardt, J., Ambach, A., Biesalski, H. K., and Gollnick, H., Photoprotection of UV-irradiation human skin: an antioxidative combination of vitamins E and C, carotenoids, selenium and proanthocyanidins. Skin Pharmmacol. Appl. Skin Physiol., 15, 307-315 (2002) https://doi.org/10.1159/000064534
  15. Harborn, J. B. and Mabry, T. J., The flavonoids : advances in research. Chapman and Hall., pp. 19-40, (1982)
  16. Hatano, T., Kagawa, H., Yasuhara, T., and Okuda, T, Two new flavonoids and other constituents in licorice root: their relative astringency and radical scavenging effects. Chem. Pharm. Bull., 36, 2090-2097 (1988) https://doi.org/10.1248/cpb.36.2090
  17. Hoekstra, R., Eskens, F. A. L. M., and Verweij, J., Matrix metalloproteinase inhibitors: current developments and future perspectives. The Oncologist, 6, 415-427 (2001) https://doi.org/10.1634/theoncologist.6-5-415
  18. Jensen, P. R., Jenkins, K. M., Porter, D., and Fenical, W., Evidence that a new antibiotic flavone glycoside chemically defends the sea grass Thalassia testudinum against zoosporic fungi. Appl. Envir. Microbiol., 64, 1490-1496 (1998)
  19. Ji, L. L., Antioxidants and oxidative stress in exercies. Proc. Soc. Exp. Biol. Med., 222, 283-292 (1999) https://doi.org/10.1046/j.1525-1373.1999.d01-145.x
  20. Lee, S. Y, Kwon, C. J., Heo, S., and Chi, C. I., Seagrass (Zostera marina L., Zosteraceae) bed in the brackish like Hwajinpo, Korea. Korean J. Limnol., 33, 336-341 (2000)
  21. Leung, D., Abbenante, G., and Fairlie, D. P., Protease inhibitors: current status and future prospects. J. Med. Chem., 43, 305-341 (2000) https://doi.org/10.1021/jm990412m
  22. Mosmann, T., Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods, 65, 55-63 (1983) https://doi.org/10.1016/0022-1759(83)90303-4
  23. Netzel-Arnett, S., Mitola, D. J., Yamada, S. S., Chrysovergis, K., Holmbeck, K., Birkedal-Hansen, H., and Bugge, T. H., Collagen dissolution by keratinocytes requires cell surface plasminogen activation and matrix metalloproteinase activity. J. Biol. Chem., 277, 45154-45161 (2002) https://doi.org/10.1074/jbc.M206354200
  24. Offord, E. A., Gautier, J. C., Avanti, O., Scaletta, C., Runge, F., Kramer, K., and Applegate, L. A., Photoprotective potential of lycopene, beta-carotene, vitamin E, vitamin C and carnosic acid in UVA-irradiated human skin fibroblasts. Free Radic. Biol. Med., 32, 1293-1303 (2002) https://doi.org/10.1016/S0891-5849(02)00831-6
  25. Petersen, M. J., Hansen, C., and Craig, S., Ultraviolet A irradiation stimulates collagenase production in cultured human fibroblasts. J. Invest. Dermatol., 99, 440-444 (1992) https://doi.org/10.1111/1523-1747.ep12616142
  26. Ramos-e-Silva, M., Hexsel, D. M., Rutowitsch, M. S., and Zechmeister, M., Hydroxy acids and retinoids in cosmetics. Clin. Dermatol., 19, 460-466 (2001) https://doi.org/10.1016/S0738-081X(01)00189-4
  27. Scharffetter-Kochanek, K., Wlaschek, M., Briviba, K., and Seis, H., Singlet oxygen induces collagenase expression in human skin fibroblasts. FEBS Lett., 331, 304-306 (1993) https://doi.org/10.1016/0014-5793(93)80357-Z
  28. Scharffetter-Kochanek, K., Brenneisen, P., Wenk, J., Herrmann, G., Ma, W., Kuhr, L., Meewes, C., and Wlaschek, M., Photoaging of the skin from phenotype to mechanisms. Exp. Gerontol., 35, 307-316 (2000) https://doi.org/10.1016/S0531-5565(00)00098-X
  29. Song, L., Xu, M., Lopes-Virella, M. F., and Huang, Y, Quercetin inhibits matrix metalloproteinase-1 expression in human vascular endothelial cells through extracellular signal-regulated kinase. Arch. Biochem. Biophys., 391, 72-78 (2001) https://doi.org/10.1006/abbi.2001.2402
  30. Wlaschek, M., Heinen, G., Poswig, A., Schwarz, A., Krieg, T., and Scharffetter-Kochanek, K., UVA-induced autocrine stimu-lation of fibroblast-derived coliagenase/MMP-1 by interrelated loops of interleukin-1 and interleukin-6. Phytochem. Photobiol., 59, 550-556 (1994) https://doi.org/10.1111/j.1751-1097.1994.tb02982.x
  31. Zhu, Y., Liu, X., Ertl, R. F., Kohyama, T., Wen, F., Wang, H., Spurzem, J. R., Romberger, D. J., and Rennard, S. I., Retinoic acid attenuates cytokine-driven fibroblast degradation of extracellular matrix in three-dimensional culture. Am. J. Respir. Cell Mol. Biol., 25, 620-627 (2001) https://doi.org/10.1165/ajrcmb.25.5.4495