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      Isolation of linoleic acid as an estrogenic compound from the fruits of Vitex agnus-castus L. (chaste-berry).

      Phytomedicine
      Breast Neoplasms, drug therapy, pathology, Cell Line, Tumor, drug effects, DNA Primers, Endometrial Neoplasms, Estrogen Antagonists, administration & dosage, pharmacology, therapeutic use, Estrogen Receptor alpha, Estrogen Receptor beta, Female, Fruit, Gene Expression Regulation, Neoplastic, Humans, Linoleic Acid, Neoplasms, Hormone-Dependent, Phytotherapy, Plant Extracts, RNA, Messenger, Receptors, Estrogen, genetics, Receptors, Progesterone, Reverse Transcriptase Polymerase Chain Reaction, Vitex

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          Abstract

          A methanol extract of chaste-tree berry (Vitex agnus-castus L.) was tested for its ability to displace radiolabeled estradiol from the binding site of estrogen receptors alpha (ERalpha) and beta (ERbeta). The extract at 46 +/- 3 microg/ml displaced 50% of estradiol from ERalpha and 64 +/- 4 microg/ml from ERbeta. Treatment of the ER+ hormone-dependent T47D:A18 breast cancer cell line with the extract induced up-regulation of ERbeta mRNA. Progesterone receptor (PR) mRNA was upregulated in the Ishikawa endometrial cancer cell line. However, chaste-tree berry extract did not induce estrogen-dependent alkaline phosphatase (AP) activity in Ishikawa cells. Bioassay-guided isolation, utilizing ER binding as a monitor, resulted in the isolation of linoleic acid as one possible estrogenic component of the extract. The use of pulsed ultrafiltration liquid chromatography-mass spectrometry, which is an affinity-based screening technique, also identified linoleic acid as an ER ligand based on its selective affinity, molecular weight, and retention time. Linoleic acid also stimulated mRNA ERbeta expression in T47D:A18 cells, PR expression in Ishikawa cells, but not AP activity in Ishikawa cells. These data suggest that linoleic acid from the fruits of Vitex agnus-castus can bind to estrogen receptors and induce certain estrogen inducible genes.

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