Prenylation has a compound specific effect on the estrogenicity of naringenin and genistein

Research output: Contribution to journalResearch articleContributedpeer-review

Contributors

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.

Details

Original languageEnglish
Pages (from-to)1-6
Number of pages6
JournalThe Journal of Steroid Biochemistry and Molecular Biology
Volume118
Issue number1-2
Publication statusPublished - Jan 2010
Peer-reviewedYes

External IDs

Scopus 72449155036
ORCID /0000-0001-5397-7972/work/142245265

Keywords

Sustainable Development Goals

Keywords

  • Alkaline Phosphatase/metabolism, Animals, Cell Line, Tumor, Estradiol/pharmacology, Estrogen Receptor alpha/genetics, Estrogens/pharmacology, Flavanones/chemistry, Gene Expression/drug effects, Genes, Reporter/genetics, Genistein/analogs & derivatives, Humans, Luciferases/genetics, Phytoestrogens/pharmacology, Prenylation, Promoter Regions, Genetic/genetics, Response Elements/genetics, Saccharomyces cerevisiae/genetics, Transfection, Vitellogenins/genetics, Xenopus, beta-Galactosidase/genetics

Library keywords