Prenylation has a compound specific effect on the estrogenicity of naringenin and genistein |
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| Authors: | Georg Kretzschmar Oliver Zierau Jannette Wober Sandra Tischer Peter Metz Günter Vollmer |
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| Institution: | 1. Institute of Zoology, Technische Universität Dresden, Zellescher Weg 20b, 01062 Dresden, Germany;2. Institute of Organic Chemistry, Technische Universität Dresden, 01062 Dresden, Germany;1. Oil and POPs Research Group, Korea Institute of Ocean Science & Technology, Geoje 656-834, Republic of Korea;2. Department of Marine Environmental Engineering, Institute of Marine Industry, Gyeongsang National University, Tongyeng 650-160, Republic of Korea;3. Library of Marine Samples, Korea Institute of Ocean Science & Technology, Geoje 656-834, Republic of Korea;4. South Sea Environment Research Department, Korea Institute of Ocean Science & Technology, Geoje 656-834, Republic of Korea;1. Department of Internal Medicine I, Medical University Hospital, Tuebingen, Germany;2. Division of Dermatologic Oncology, Department of Dermatology and Allergology, University of Tuebingen, Tuebingen, Germany;3. HHV Hallertauer Hopfenveredelungsgesellschaft m.b.H., Mainburg, Germany;4. Institute of Biological Chemistry and Nutrition, University of Hohenheim, Stuttgart, Germany;5. Pallas Clinic, Winterthur, Switzerland;1. Department of Trauma and Reconstructive Surgery, University Hospital “Carl Gustav Carus”, Technische Universität Dresden, Fetscherstrasse 74, Dresden 01307, Germany;2. Institute of Immunology, Medical Faculty “Carl Gustav Carus”, Technische Universität Dresden, Fetscherstrasse 74, Dresden 01307, Germany;3. Max Bergmann Center of Biomaterials, Technische Universität Dresden, Budapester Str. 27, Dresden 01069, Germany;4. Institute for Zoology, Chair for Molecular Cell Physiology and Endocrinology, Technische Universität Dresden, Zellescher Weg 2b, Dresden 01062, Germany;5. Biomedical Engineering Division, School of Bio-Sciences and Technology, VIT University, Vellore, Tamilnadu 623014, India;6. BAM Federal Institute for Materials Research and Testing, Unter den Eichen 87, Berlin 12205, Germany;7. Max Planck Institute of Colloids and Interfaces, Department of Biomaterials, Potsdam-Golm Science Park, Am Mühlenberg 1, Potsdam 14476, Germany;8. Center for Regenerative Therapies Dresden (CRTD), Tatzberg 47, Dresden 01307, Germany;1. Institute of Zoology, Molecular Cell Physiology and Endocrinology, Technische Universität Dresden, 01062 Dresden, Germany;2. Cancer Research Center, Department of Biomedical Sciences, School of Public Health, University at Albany, Rensselear, NY, USA;3. Institute of Doping Analysis and Sports Biochemistry (IDAS), Kreischa, Dresden, Germany;1. Department of Earth and Environmental Sciences, University of Waterloo, 200 University Avenue West, Waterloo, Ontario N2L 3G1, Canada;2. Aquanty, Inc, 564 Weber Street North, Unit 12, Waterloo, Ontario N2L 5C6, Canada |
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| Abstract: | A variety of plant derived substances, so-called phytoestrogens (PEs), although structurally not related to steroids, produce effects similar to the mammalian estradiol. However, little is known so far about the structural requirements which determine PE activities. Taking into consideration that prenylation reactions are relatively common in plant secondary metabolism, the activity of a set of three PE derivatives of genistein and naringenin, namely genistein, 8-prenylgenistein (8PG), 6-(1,1-dimethylallyl)genistein (6DMAG), naringenin, 8-prenylnaringenin (8PN) and 6-(1,1-dimethylallyl)naringenin (6DMAN) was compared regarding structure–estrogenicity relationships in three functionally different estrogen receptor assays.Strong estrogenic activities were recorded for 6DMAN and 8PN in all assays used, while the parent compound naringenin showed only very weak estrogenicity.In contrast, in the case of genistein derivatives, only genistein itself exhibited estrogenic activity in a yeast based assay. In MVLN breast cancer cells, a bioluminescent MCF-7-derived cell line, the estrogenic activity of all three genistein derivatives was similar. Studying alkaline phosphatase activity in Ishikawa endometrial cancer cells as an estrogenic response marker revealed a similar pattern of estrogenicity of the genistein derivatives compared to the yeast based assay although a slight estrogenic effect of 6DMAG and 8PG was apparent.In summary, this study demonstrates that prenylation often found in plant secondary metabolism differentially modifies estrogenic properties of PEs depending on the basic structure of the respective PE. |
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