Isolation of linoleic acid as an estrogenic compound from the fruits of Vitex agnus-castus L. (chaste-berry)
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 (ERα) and beta (ERβ). The extract at 46 ± 3 μg/ml displaced 50% of estradiol from ERα and 64 ± 4 μg/ml from ERβ. Treatment...
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| Veröffentlicht in: | Phytomedicine (Stuttgart) 2004, Vol.11 (1), p.18-23 |
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| creator | Liu, J. Burdette, J.E. Sun, Y. Deng, S. Schlecht, S.M. Zheng, W. Nikolic, D. Mahady, G. van Breemen, R.B. Fong, H.H.S. Pezzuto, J.M. Bolton, J.L. Farnsworth, N.R. |
| description | 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 (ERα) and beta (ERβ). The extract at 46 ± 3 μg/ml displaced 50% of estradiol from ERα and 64 ± 4 μg/ml from ERβ. Treatment of the ER+ hormone-dependent T47D:A18 breast cancer cell line with the extract induced up-regulation of ERβ 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 ERβ 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. |
| doi_str_mv | 10.1078/0944-7113-00331 |
| format | Article |
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Vitex agnus-castus L.) was tested for its ability to displace radiolabeled estradiol from the binding site of estrogen receptors alpha (ERα) and beta (ERβ). The extract at 46 ± 3 μg/ml displaced 50% of estradiol from ERα and 64 ± 4 μg/ml from ERβ. Treatment of the ER+ hormone-dependent T47D:A18 breast cancer cell line with the extract induced up-regulation of ERβ 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 ERβ 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.</description><identifier>ISSN: 0944-7113</identifier><identifier>EISSN: 1618-095X</identifier><identifier>DOI: 10.1078/0944-7113-00331</identifier><identifier>PMID: 14974442</identifier><language>eng</language><publisher>Germany: Elsevier GmbH</publisher><subject>Breast Neoplasms - drug therapy ; Breast Neoplasms - pathology ; Case studies ; Cell Line, Tumor - drug effects ; chaste-berry ( Vitex agnus-castus) ; DNA Primers ; Endometrial Neoplasms - drug therapy ; Endometrial Neoplasms - pathology ; Estrogen ; Estrogen Antagonists - administration & dosage ; Estrogen Antagonists - pharmacology ; Estrogen Antagonists - therapeutic use ; Estrogen Receptor alpha ; estrogen receptor alpha (ERα) and beta (ERβ) ; Estrogen Receptor beta ; Female ; Fruit ; Gene Expression Regulation, Neoplastic ; Health aspects ; Humans ; linoleic acid ; Linoleic Acid - administration & dosage ; Linoleic Acid - pharmacology ; Linoleic Acid - therapeutic use ; Linoleic acids ; Neoplasms, Hormone-Dependent - drug therapy ; Neoplasms, Hormone-Dependent - pathology ; Phytotherapy ; Plant Extracts - administration & dosage ; Plant Extracts - pharmacology ; Plant Extracts - therapeutic use ; progesterone receptor ; Receptors ; Receptors, Estrogen - drug effects ; Receptors, Estrogen - genetics ; Receptors, Progesterone - drug effects ; Receptors, Progesterone - genetics ; Reverse Transcriptase Polymerase Chain Reaction ; RNA, Messenger - drug effects ; Vitex</subject><ispartof>Phytomedicine (Stuttgart), 2004, Vol.11 (1), p.18-23</ispartof><rights>2004 Urban & Fischer Verlag</rights><rights>COPYRIGHT 2004 Urban & Fischer Verlag</rights><rights>Copyright Urban & Fischer Verlag Jan 2004</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c567t-ba5c08437ef9d677a4ab3cc12e4412a3a6d95f7e1374335476775646766bb3b13</citedby><cites>FETCH-LOGICAL-c567t-ba5c08437ef9d677a4ab3cc12e4412a3a6d95f7e1374335476775646766bb3b13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0944711304702901$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,4010,27900,27901,27902,65534</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14974442$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, J.</creatorcontrib><creatorcontrib>Burdette, J.E.</creatorcontrib><creatorcontrib>Sun, Y.</creatorcontrib><creatorcontrib>Deng, S.</creatorcontrib><creatorcontrib>Schlecht, S.M.</creatorcontrib><creatorcontrib>Zheng, W.</creatorcontrib><creatorcontrib>Nikolic, D.</creatorcontrib><creatorcontrib>Mahady, G.</creatorcontrib><creatorcontrib>van Breemen, R.B.</creatorcontrib><creatorcontrib>Fong, H.H.S.</creatorcontrib><creatorcontrib>Pezzuto, J.M.</creatorcontrib><creatorcontrib>Bolton, J.L.</creatorcontrib><creatorcontrib>Farnsworth, N.R.</creatorcontrib><title>Isolation of linoleic acid as an estrogenic compound from the fruits of Vitex agnus-castus L. (chaste-berry)</title><title>Phytomedicine (Stuttgart)</title><addtitle>Phytomedicine</addtitle><description>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 (ERα) and beta (ERβ). The extract at 46 ± 3 μg/ml displaced 50% of estradiol from ERα and 64 ± 4 μg/ml from ERβ. Treatment of the ER+ hormone-dependent T47D:A18 breast cancer cell line with the extract induced up-regulation of ERβ 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 ERβ 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.</description><subject>Breast Neoplasms - drug therapy</subject><subject>Breast Neoplasms - pathology</subject><subject>Case studies</subject><subject>Cell Line, Tumor - drug effects</subject><subject>chaste-berry ( Vitex agnus-castus)</subject><subject>DNA Primers</subject><subject>Endometrial Neoplasms - drug therapy</subject><subject>Endometrial Neoplasms - pathology</subject><subject>Estrogen</subject><subject>Estrogen Antagonists - administration & dosage</subject><subject>Estrogen Antagonists - pharmacology</subject><subject>Estrogen Antagonists - therapeutic use</subject><subject>Estrogen Receptor alpha</subject><subject>estrogen receptor alpha (ERα) and beta (ERβ)</subject><subject>Estrogen Receptor beta</subject><subject>Female</subject><subject>Fruit</subject><subject>Gene Expression Regulation, Neoplastic</subject><subject>Health aspects</subject><subject>Humans</subject><subject>linoleic acid</subject><subject>Linoleic Acid - administration & dosage</subject><subject>Linoleic Acid - pharmacology</subject><subject>Linoleic Acid - therapeutic use</subject><subject>Linoleic acids</subject><subject>Neoplasms, Hormone-Dependent - drug therapy</subject><subject>Neoplasms, Hormone-Dependent - pathology</subject><subject>Phytotherapy</subject><subject>Plant Extracts - administration & dosage</subject><subject>Plant Extracts - pharmacology</subject><subject>Plant Extracts - therapeutic use</subject><subject>progesterone receptor</subject><subject>Receptors</subject><subject>Receptors, Estrogen - drug effects</subject><subject>Receptors, Estrogen - genetics</subject><subject>Receptors, Progesterone - drug effects</subject><subject>Receptors, Progesterone - genetics</subject><subject>Reverse Transcriptase Polymerase Chain Reaction</subject><subject>RNA, Messenger - drug effects</subject><subject>Vitex</subject><issn>0944-7113</issn><issn>1618-095X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>BENPR</sourceid><recordid>eNp1kt-L1DAQx4Mo3rr67JsGBdGH7iVNmrSPx-GPgwUf9MS3ME2neznaZE1a8f57U3dRlJVAZph8vjOZTAh5ytmGM12fs0bKQnMuCsaE4PfIiiteF6ypvt4nq9-nZ-RRSreMcdlo9pCcLVZKWa7IcJXCAJMLnoaeDs6HAZ2lYF1HIVHwFNMUww59jtow7sPsO9rHMNLpBrMzuykt0i9uwh8Udn5OhYU0zYluN_S1vck-Fi3GePfmMXnQw5DwydGuyfW7t58vPxTbj--vLi-2ha2UnooWKstqKTT2Tae0BgmtsJaXKCUvQYDqmqrXyIWWQlRSZ6ZSUmml2la0XKzJq0PefQzf5tyAGV2yOAzgMczJ1IyrRtZ1Bl_8A96GOfp8N1OyqhKqzNuavDxAOxjQON-HKYJdMpoLzquyrEWzUMUJKr8bRhiCx97l8F_85gSfV4ejsycF5weBjSGliL3ZRzdCvDOcmeUzmGXcZhm3-fUZsuLZsbu5HbH7wx-nn4HnB6CHYGAXXTLXn0rGBeOMac2Xos2BwDyu7w6jSdaht9i5iHYyXXD_Lf8Tf8rG6Q</recordid><startdate>2004</startdate><enddate>2004</enddate><creator>Liu, J.</creator><creator>Burdette, J.E.</creator><creator>Sun, Y.</creator><creator>Deng, S.</creator><creator>Schlecht, S.M.</creator><creator>Zheng, W.</creator><creator>Nikolic, D.</creator><creator>Mahady, G.</creator><creator>van Breemen, R.B.</creator><creator>Fong, H.H.S.</creator><creator>Pezzuto, J.M.</creator><creator>Bolton, J.L.</creator><creator>Farnsworth, N.R.</creator><general>Elsevier GmbH</general><general>Urban & Fischer Verlag</general><general>Elsevier Science Ltd</general><scope>FBQ</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7RV</scope><scope>7X2</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>88I</scope><scope>8AF</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>ATCPS</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB0</scope><scope>M0K</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>NAPCQ</scope><scope>PHGZM</scope><scope>PHGZT</scope><scope>PJZUB</scope><scope>PKEHL</scope><scope>PPXIY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>Q9U</scope><scope>S0X</scope><scope>7X8</scope></search><sort><creationdate>2004</creationdate><title>Isolation of linoleic acid as an estrogenic compound from the fruits of Vitex agnus-castus L. (chaste-berry)</title><author>Liu, J. ; Burdette, J.E. ; Sun, Y. ; Deng, S. ; Schlecht, S.M. ; Zheng, W. ; Nikolic, D. ; Mahady, G. ; van Breemen, R.B. ; Fong, H.H.S. ; Pezzuto, J.M. ; Bolton, J.L. ; Farnsworth, N.R.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c567t-ba5c08437ef9d677a4ab3cc12e4412a3a6d95f7e1374335476775646766bb3b13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Breast Neoplasms - drug therapy</topic><topic>Breast Neoplasms - pathology</topic><topic>Case studies</topic><topic>Cell Line, Tumor - drug effects</topic><topic>chaste-berry ( Vitex agnus-castus)</topic><topic>DNA Primers</topic><topic>Endometrial Neoplasms - drug therapy</topic><topic>Endometrial Neoplasms - pathology</topic><topic>Estrogen</topic><topic>Estrogen Antagonists - administration & dosage</topic><topic>Estrogen Antagonists - pharmacology</topic><topic>Estrogen Antagonists - therapeutic use</topic><topic>Estrogen Receptor alpha</topic><topic>estrogen receptor alpha (ERα) and beta (ERβ)</topic><topic>Estrogen Receptor beta</topic><topic>Female</topic><topic>Fruit</topic><topic>Gene Expression Regulation, Neoplastic</topic><topic>Health aspects</topic><topic>Humans</topic><topic>linoleic acid</topic><topic>Linoleic Acid - administration & dosage</topic><topic>Linoleic Acid - pharmacology</topic><topic>Linoleic Acid - therapeutic use</topic><topic>Linoleic acids</topic><topic>Neoplasms, Hormone-Dependent - drug therapy</topic><topic>Neoplasms, Hormone-Dependent - pathology</topic><topic>Phytotherapy</topic><topic>Plant Extracts - administration & dosage</topic><topic>Plant Extracts - pharmacology</topic><topic>Plant Extracts - therapeutic use</topic><topic>progesterone receptor</topic><topic>Receptors</topic><topic>Receptors, Estrogen - drug effects</topic><topic>Receptors, Estrogen - genetics</topic><topic>Receptors, Progesterone - drug effects</topic><topic>Receptors, Progesterone - genetics</topic><topic>Reverse Transcriptase Polymerase Chain Reaction</topic><topic>RNA, Messenger - drug effects</topic><topic>Vitex</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, J.</creatorcontrib><creatorcontrib>Burdette, J.E.</creatorcontrib><creatorcontrib>Sun, Y.</creatorcontrib><creatorcontrib>Deng, S.</creatorcontrib><creatorcontrib>Schlecht, S.M.</creatorcontrib><creatorcontrib>Zheng, W.</creatorcontrib><creatorcontrib>Nikolic, D.</creatorcontrib><creatorcontrib>Mahady, G.</creatorcontrib><creatorcontrib>van Breemen, R.B.</creatorcontrib><creatorcontrib>Fong, H.H.S.</creatorcontrib><creatorcontrib>Pezzuto, J.M.</creatorcontrib><creatorcontrib>Bolton, J.L.</creatorcontrib><creatorcontrib>Farnsworth, N.R.</creatorcontrib><collection>AGRIS</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Nursing & Allied Health Database</collection><collection>Agricultural Science Collection</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Science Database (Alumni Edition)</collection><collection>STEM Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>Agricultural & Environmental Science Collection</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Natural Science Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Nursing & Allied Health Database (Alumni Edition)</collection><collection>Agricultural Science Database</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Science Database</collection><collection>Nursing & Allied Health Premium</collection><collection>ProQuest Central (New)</collection><collection>ProQuest One Academic (New)</collection><collection>ProQuest Health & Medical Research Collection</collection><collection>ProQuest One Academic Middle East (New)</collection><collection>ProQuest One Health & Nursing</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>ProQuest Central Basic</collection><collection>SIRS Editorial</collection><collection>MEDLINE - Academic</collection><jtitle>Phytomedicine (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, J.</au><au>Burdette, J.E.</au><au>Sun, Y.</au><au>Deng, S.</au><au>Schlecht, S.M.</au><au>Zheng, W.</au><au>Nikolic, D.</au><au>Mahady, G.</au><au>van Breemen, R.B.</au><au>Fong, H.H.S.</au><au>Pezzuto, J.M.</au><au>Bolton, J.L.</au><au>Farnsworth, N.R.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Isolation of linoleic acid as an estrogenic compound from the fruits of Vitex agnus-castus L. (chaste-berry)</atitle><jtitle>Phytomedicine (Stuttgart)</jtitle><addtitle>Phytomedicine</addtitle><date>2004</date><risdate>2004</risdate><volume>11</volume><issue>1</issue><spage>18</spage><epage>23</epage><pages>18-23</pages><issn>0944-7113</issn><eissn>1618-095X</eissn><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 (ERα) and beta (ERβ). The extract at 46 ± 3 μg/ml displaced 50% of estradiol from ERα and 64 ± 4 μg/ml from ERβ. Treatment of the ER+ hormone-dependent T47D:A18 breast cancer cell line with the extract induced up-regulation of ERβ 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 ERβ 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.</abstract><cop>Germany</cop><pub>Elsevier GmbH</pub><pmid>14974442</pmid><doi>10.1078/0944-7113-00331</doi><tpages>6</tpages></addata></record> |
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| subjects | Breast Neoplasms - drug therapy Breast Neoplasms - pathology Case studies Cell Line, Tumor - drug effects chaste-berry ( Vitex agnus-castus) DNA Primers Endometrial Neoplasms - drug therapy Endometrial Neoplasms - pathology Estrogen Estrogen Antagonists - administration & dosage Estrogen Antagonists - pharmacology Estrogen Antagonists - therapeutic use Estrogen Receptor alpha estrogen receptor alpha (ERα) and beta (ERβ) Estrogen Receptor beta Female Fruit Gene Expression Regulation, Neoplastic Health aspects Humans linoleic acid Linoleic Acid - administration & dosage Linoleic Acid - pharmacology Linoleic Acid - therapeutic use Linoleic acids Neoplasms, Hormone-Dependent - drug therapy Neoplasms, Hormone-Dependent - pathology Phytotherapy Plant Extracts - administration & dosage Plant Extracts - pharmacology Plant Extracts - therapeutic use progesterone receptor Receptors Receptors, Estrogen - drug effects Receptors, Estrogen - genetics Receptors, Progesterone - drug effects Receptors, Progesterone - genetics Reverse Transcriptase Polymerase Chain Reaction RNA, Messenger - drug effects Vitex |
| title | Isolation of linoleic acid as an estrogenic compound from the fruits of Vitex agnus-castus L. (chaste-berry) |
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