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 (compounds1,2, and3) were isolated from an ethyl acetate (EtOAc) soluble fraction of the product; they were identified as apigenin-7-O-β-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 SC50 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 μM and inhibited the production of interleukin 6 (IL-6), which is known as a cytokine that induces MMP-1 expression. From these results, compound3 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.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
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)
Blois, M. S., Antioxidant determinations, by the use of a stable free radical.Nature, 181, 1199–1200 (1958).
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 irradiationmediated 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).
Brieskom, V. C. H. and Riedel, W., Flavonoids fromcoleus amboinicus.Planta Medica, 31, 308–310 (1977).
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).
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).
Ersoz, T., Harput, U. S., Saracoglu, I., Calis, I., and Ogihara, Y., Phenolic compounds fromScutellaria pontica.Turk. J. Chem., 26, 581–588 (2002).
Fisher, G. J., Datta, S. C., Talwar, H. S., Wang, Z., Varanl, J., Kang, S. W., and Voorhees, J. J., Molecular basis of suninduced premature skin ageing and retinoid antagonism.Nature, 379, 335–339 (1996).
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).
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).
Furuno, K., Akasako, T., and Sugihara, N., The contribution of the pyrogallol moiety to the superoxide radical scavenging activity of flavonoids.Biol. Pharm. Bull., 25, 19–23 (2002).
Gilchrest, B. A., Garmyn, M., and Yaar, M., Aging and photoaging affect gene expression in cultured human keratinocytes.Arch. Dermatol., 130, 82–86 (1994).
Girotti, A. W., Lipid hydroperoxide generation, turnover, and effector action in biological systems.J. Lipid Res., 39, 1529–1542 (1998).
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).
Harborn, J. B. and Mabry, T. J., The flavonoids: advances in research. Chapman and Hall., pp. 19–40, (1982).
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).
Hoekstra, R., Eskens, F. A. L. M., and Verweij, J., Matrix metalloproteinase inhibitors: current developments and future perspectives.The Oncologist, 6, 415–427 (2001).
Jensen, P. R., Jenkins, K. M., Porter, D., and Fenical, W., Evidence that a new antibiotic flavone glycoside chemically defends the sea grassThalassia testudinum against zoosporic fungi.Appl. Envir. Microbiol., 64, 1490–1496 (1998).
Ji, L. L., Antioxidants and oxidative stress in exercies.Proc. Soc. Exp. Biol. Med., 222, 283–292 (1999).
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).
Leung, D., Abbenante, G., and Fairlie, D. P., Protease inhibitors: current status and future prospects.J. Med. Chem., 43, 305–341 (2000).
Mosmann, T., Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.J. Immunol. Methods 65, 55–63 (1983).
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).
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 camosic acid in UVA-irradiated human skin fibroblasts.Free Radic. Biol. Med. 32, 1293–1303 (2002).
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).
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).
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).
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).
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).
Wlaschek, M., Heinen, G., Poswig, A., Schwarz, A., Krieg, T., and Scharffetter-Kochanek, K., UVA-induced autocrine stimulation of fibroblast-derived collagenase/MMP-1 by interrelated loops of interleukin-1 and interleukin-6.Phytochem. Photobiol., 59, 550–556 (1994).
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).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kim, J.H., Cho, Y.H., Park, S.M. et al. Antioxidants and inhibitor of matrix metalloproteinase-1 expression from leaves ofzostera marina L.. Arch Pharm Res 27, 177–183 (2004). https://doi.org/10.1007/BF02980103
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02980103