Effect of catechins and citrus flavonoids on invasionin vitro

Abstract

Catechins, a group of flavonoid molecules, inhibit invasion of mouse MO4 cells into embryonic chick heart fragmentsin vitro. The anti-invasive effects can be ranked as follows: (+)-catechin > (−)-epicatechin>3-O-methyl-(+)-catechin > 3-O-palmitoyl-(+)-catechin. Most of the catechins are unstable in cell culture media, and their spontaneous rearrangement products tend to bind to extracellular matrix (ECM). Due to these interactions proteases such as tissue-type plasminogen activator (t-PA) are linked to the ECM glycoprotein laminin. This leads to a partial inactivation of the enzyme. Within the group of catechins we found a positive correlation between anti-invasive activity and linking of t-PA to laminin. Citrus flavonoids are also anti-invasivein vitro (tangeretin > nobiletin > hesperidin = naringin). However, these stable molecules show poor affinity for ECM, and do not link enzymes to laminin. These data suggest that catechins and citrus flavonoids inhibit invasionin vitro by different mechanisms.

This is a preview of subscription content, log in to check access.

References

  1. [1]

    Akimoto, G. C., andSugimoto, I., 1983, Degradation of (+)-cyanidanol-3 by sodium sulfite in aqueous solution.Chemical Pharmaceutical Bulletin,31, 214–220.

    Google Scholar 

  2. [2]

    Attia, M. A., andWeiss, D. W., 1966, Immunology of spontaneous mammary carcinomas in mice. V. Acquired tumor resistance and enhancement in strain A mice infected with mammary tumor virus.Cancer Research,26, 1787–1800.

    PubMed  Google Scholar 

  3. [3]

    Aumailley, M., Nurcombe, V., Edgar, D., Paulsson, M., andTimpl, R., 1987, The cellular interactions of laminin fragments. Cell adhesion correlates with two fragment-specific high affinity binding sites.Journal of Biological Chemistry,262, 11532–11538.

    PubMed  Google Scholar 

  4. [4]

    Billiau, A., Sobis, H., Eyssen, H., andVan den Berghe, H., 1973, Non-infectious intracisternal A-type particles in a sarcoma-positive, leukemia-negative mouse cell line transformed by murine sarcoma virus (MSV).Archiv für Gesamte Virusforschung,43, 345–351.

    Google Scholar 

  5. [5]

    Bracke, M. E., Van Cauwenberge, R. M.-L., andMareel, M., 1984, (+)-Catechin inhibits the invasion of malignant fibrosarcoma cells into chick heartin vitro.Clinical and Experimental Metastasis,2, 161–170.

    PubMed  Google Scholar 

  6. [6]

    Bracke, M. E., Van Cauwenberge, R. M.-L., Mareel, M. M., Castronovo, V., andFoidart, J.-M., 1986, Flavonoids: tools for the study of tumor invasionin vitro.Plant Flavonoids in Biology and Medicine: Biochemical, Pharmacological and Structure-Activity Relationships, edited by V. Cody, E. Middleton, Jr and J. B. Harborne (New York: Alan R. Liss), pp. 441–444.

    Google Scholar 

  7. [7]

    Bracke, M. E., Castronovo, V., Van Cauwenberge, R. M.-L., Coopman, P., Vakaet, L. Jr, Strojny, P., Foidart, J.-M., andMareel, M. M., 1987, The anti-invasive flavonoid (+)-catechin binds to laminin and abrogates the effect of laminin on cell morphology and adhesion.Experimental Cell Research,173, 193–205.

    PubMed  Google Scholar 

  8. [8]

    Bracke, M. E., De Pestel, G., Castronovo, V., Vyncke, B., Foidart, J.-M., Vakaet, L. C. A., andMareel, M. M., 1988, Flavonoids inhibit malignant tumor invasionin vitro.Plant Flavonoids in Biology and Medicine II. Biochemical, Cellular and Medicinal Properties, edited by V. Cody, E. Middleton, Jr, J. B. Harborne and A. Beretz (New York: Alan R. Liss), pp. 219–233.

    Google Scholar 

  9. [9]

    Bracke, M. E., Vyncke, B. M., Van Larebeke, N. A., Bruyneel, E. A., De Bruyne, G. K., De Pestel, G. H., De Coster, W. J., Espeel, M. F., andMareel, M. M., 1989, The flavonoid tangeretin inhibits invasion of MO4 mouse cells into embryonic chick heartin vitro.Clinical and Experimental Metastasis,7, 283–300.

    PubMed  Google Scholar 

  10. [10]

    Danø, K., Andreasen, P. A., Grondahl-Hansen, J., Kristensen, P., Nielsen, L. S., andSkriver, L., 1985, Plasminogen activators, tissue degradation, and cancer.Advances in Cancer Research,44, 139–266.

    PubMed  Google Scholar 

  11. [11]

    Distelmans, W., Van Ginckel, R., Vanherck, W., andDe Brabander, M., 1985, The kidney invasion test: an assay allowing macroscopic quantification of malignant invasionin vivo.Invasion and Metastasis,5, 170–184.

    Google Scholar 

  12. [12]

    Kiatgrajai, P., Wellons, J. D., Gollab, L., andWhite, J. D., 1982, Kinetics of epimerization of (+)-catechin and its rearrangement to catechinic acid.Journal of Organic Chemistry,47, 2910–2912.

    Google Scholar 

  13. [13]

    Leivo, I., andEngvall, E., 1986, C3d fragment of complement interacts with laminin and binds to basement membranes of glomerulus and trophoblast.Journal of Cell Biology,103, 1091–1100.

    PubMed  Google Scholar 

  14. [14]

    Liotta, L. A., Wewer, U., Rao, N. C., Schiffmann, E., Stracke, M., Guirguis, R., Thorgeirsson, U., Muschel, R., andSobel, M., 1988, Biochemical mechanisms of tumor invasion and metastases.Cancer Metastasis, Biological and Biochemical Mechanisms and Clinical Aspects, edited by G. Prodi, L. A. Liotta, P.-L. Lollini, S. Garbisa, S. Gorini and K. Hellmann (New York, London: Plenum Press), pp. 161–169.

    Google Scholar 

  15. [15]

    Mareel, M., Kint, J., andMeyvisch, C., 1979, Methods of study of the invasion of malignant C3H mouse fibroblasts into embryonic chick heartin vitro.Virchows Archiv B Cell Pathology,30, 95–111.

    Google Scholar 

  16. [16]

    Mareel, M., De Bruyne, G., Vandesande, F., andDragonetti, C., 1981, Immunohistochemical study of embryonic chick heart invaded by malignant cells in three-dimensional culture.Invasion and Metastasis,1, 195–204.

    Google Scholar 

  17. [17]

    Mareel, M., Bruyneel, E., Dragonetti, C., andVan Cauwenberge, R., 1982, Growth and invasion: separate activities of malignant MO4 cell populationsin vitro.Membranes in Tumour Growth, edited by T. Galeotti, A. Cittadini, G. Neri and S. Papa (Amsterdam: Elsevier), pp. 223–232.

    Google Scholar 

  18. [18]

    Mareel, M., 1983, Invasionin vitro: methods of analysis.Cancer Metastasis Reviews,2, 201–218.

    PubMed  Google Scholar 

  19. [19]

    Mareel, M., Dragonetti, C., Hooghe, R., Bruyneel, E., Bracke, M., Van Roy, F., Gao, J., De Bruyne, G., andFiers, W., 1985, Expression of cell surface glycoproteins in tumor invasionin vitro.Cell Membranes and Cancer, edited by T. Galeotti, A. Cittadini, G. Neri, S. Papa and L. A. Smets (Amsterdam: Elsevier), pp. 43–49.

    Google Scholar 

  20. [20]

    Mareel, M. M., Van Roy, F. M., Messiaen, L. M., Boghaert, E. R., andBruyneel, E. A., 1987, Qualitative and quantitative analysis of tumour invasionin vivo andin vitro, Journal of Cell Science, (Suppl.),8, 141–163.

    Google Scholar 

  21. [21]

    Mareel, M. M., Van Roy, F. M., andDe Baetselier, P., 1990, The invasive phenotypes.Cancer Metastasis Reviews,9, 45–62.

    PubMed  Google Scholar 

  22. [22]

    McCarthy, J. B., Basara, M. L., Palm, S. L., Sas, D. F., andFurcht, L. T., 1985, The role of cell adhesion proteins-laminin and fibronectin in the movement of malignant and metastatic cells.Cancer Metastasis Reviews,4, 125–152.

    PubMed  Google Scholar 

  23. [23]

    Opdenakker, G., Bosman, F., Decock, B., Cabeza-Arvelaiz, Y., Van Damme, J., andBilliau, A., 1988, Heterogeneity of human tissue-type plasminogen activator.FEBS Letters,238, 129–134.

    PubMed  Google Scholar 

  24. [24]

    Pöllänen, J., Stephens, R., Salonen, E.-M., andVaheri, A., 1988, Proteolytic mechanisms operating at the surface of invasive cells.Cancer Metastasis, Biological and Biochemical Mechanisms and Clinical Aspects, edited by G. Prodi, L. A. Liotta, P.-L. Lollini, S. Garbisa, S. Gorini and K. Hellmann (New York, London: Plenum Press), pp. 187–199.

    Google Scholar 

  25. [25]

    Romeis, B., 1968,Mikroskopische Technik (Munich, Vienna: R. Oldenbourgh Verlag), pp. 703–704.

    Google Scholar 

  26. [26]

    Salonen, E. M., Zitting, A., andVaheri, A., 1984, Laminin interacts with plasminogen and its tissue-type activator.FEBS Letters,172, 29–32.

    PubMed  Google Scholar 

  27. [27]

    Sears, K. D., Casebier, R. L., Hergert, H. L., Stout, G. H., andMcCandlish, L. E., 1974, The structure of catechinic acid. A base rearrangement product of catechin.Journal of Organic Chemistry,39, 3244–3247.

    Google Scholar 

  28. [28]

    Skubitz, A. P. N., Charonis, A. S., Tsilibary, E. C., andFurcht, L. T., 1987, Localization of a tumor cell adhesion domain of laminin by a monoclonal antibody.Experimental Cell Research,173, 349–369.

    PubMed  Google Scholar 

  29. [29]

    Thorgeirsson, U. P., Liotta, L. A., Kalebic, T., Margulies, I. M., Thomas, K., Rias-Candelore, M., andRusso, R. G., 1982, Effect of natural protease inhibitors and a chemo-attractant on tumor cell invasionin vitro.Journal of the National Cancer Institute,69, 1049–1054.

    Google Scholar 

  30. [30]

    Tilstra, L. F., Maeda, H., andMattice, W. L., 1988, Interaction of (+)-catechin with the edge of theβ-sheet formed by poly-(S-carboxymethyl-l-cysteine).Journal of the Chemical Society Perkin Transactions,II, 1613–1616.

    Google Scholar 

  31. [31]

    Timpl, R., Rohde, H., Gehron-Robey, P., Rennard, S. I., Foidart, J.-M., andMartin, G. R., 1979, Laminin—A glycoprotein from basement membranes.Journal of Biological Chemistry,254, 9933–9937.

    PubMed  Google Scholar 

  32. [32]

    Wauters, P., Eeckhout, Y., andVaes, G., 1986, Oxidation products are responsible for the resistance to the action of collagenase conferred on collagen by (+)-catechin.Biochemical Pharmacology,35, 2971–2973.

    PubMed  Google Scholar 

Download references

Author information

Affiliations

Authors

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Bracke, M., Vyncke, B., Opdenakker, G. et al. Effect of catechins and citrus flavonoids on invasionin vitro . Clin Exp Metast 9, 13–25 (1991). https://doi.org/10.1007/BF01831706

Download citation

Keywords

  • Laminin
  • Catechin
  • Epicatechin
  • Naringin
  • Hesperidin