Interaction of Phytoestrogens with Estrogen Receptors α and β (II)
We investigated the estrogenic activities of isoflavone derivatives in competition binding assays with human estrogen receptor (hER) α or hER β protein, and in a gene expression assay using a yeast system. Coumestrol binds as strongly as 17β-estradiol to both hERs. Biochanin A, 5-OMe-genistein, form...
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| Veröffentlicht in: | Biological & pharmaceutical bulletin 2002, Vol.25(1), pp.48-52 |
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| creator | Morito, Keiko Aomori, Tohru Hirose, Toshiharu Kinjo, Junei Hasegawa, Junichi Ogawa, Sumito Inoue, Satoshi Muramatsu, Masami Masamune, Yukito |
| description | We investigated the estrogenic activities of isoflavone derivatives in competition binding assays with human estrogen receptor (hER) α or hER β protein, and in a gene expression assay using a yeast system. Coumestrol binds as strongly as 17β-estradiol to both hERs. Biochanin A, 5-OMe-genistein, formononetin, and tectorigenin bind well to hER β, but significant binding to hER α is only observed with 5-OMe-genistein, formononetin and tectorigenin. The binding of 7-OMe-genistein and irisolidone is poor to both receptors. Among the glucosides, sissotorin binds both receptors and the binding is stronger than genistin. Coumestrol induces transcription as strongly as genistein. Tectorigenin also induces transcription with both hERs. Though biochanin A, 5-OMe-genistein, 7-OMe-genistein, irisolidone and formononetin slightly induce transcription with hER β, they act as antagonists in the induction of transcription by 17β-estradiol. The results show that methylation or glucosidation of isoflavones generally inhibits their phytoestrogenic activities. |
| doi_str_mv | 10.1248/bpb.25.48 |
| format | Article |
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Coumestrol binds as strongly as 17β-estradiol to both hERs. Biochanin A, 5-OMe-genistein, formononetin, and tectorigenin bind well to hER β, but significant binding to hER α is only observed with 5-OMe-genistein, formononetin and tectorigenin. The binding of 7-OMe-genistein and irisolidone is poor to both receptors. Among the glucosides, sissotorin binds both receptors and the binding is stronger than genistin. Coumestrol induces transcription as strongly as genistein. Tectorigenin also induces transcription with both hERs. Though biochanin A, 5-OMe-genistein, 7-OMe-genistein, irisolidone and formononetin slightly induce transcription with hER β, they act as antagonists in the induction of transcription by 17β-estradiol. The results show that methylation or glucosidation of isoflavones generally inhibits their phytoestrogenic activities.</description><identifier>ISSN: 0918-6158</identifier><identifier>EISSN: 1347-5215</identifier><identifier>DOI: 10.1248/bpb.25.48</identifier><identifier>PMID: 11824555</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>beta-Galactosidase - biosynthesis ; Estrogen Antagonists - pharmacology ; Estrogen Receptor alpha ; Estrogen Receptor beta ; Estrogens, Non-Steroidal - pharmacology ; hER isoflavone binding ; hER-dependent gene expression ; human estrogen receptor (hER) α and β ; Humans ; isoflavone ; Isoflavones - pharmacology ; Phytoestrogens ; Plant Preparations ; Receptors, Estrogen - biosynthesis ; Receptors, Estrogen - drug effects ; Receptors, Estrogen - genetics ; Saccharomyces cerevisiae - genetics ; Transcription, Genetic - drug effects</subject><ispartof>Biological and Pharmaceutical Bulletin, 2002, Vol.25(1), pp.48-52</ispartof><rights>2002 The Pharmaceutical Society of Japan</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c461t-ffd6e732bbcfa33a877bca51c03c302c00250e4cedf2226722f8366e5b2580b83</citedby><cites>FETCH-LOGICAL-c461t-ffd6e732bbcfa33a877bca51c03c302c00250e4cedf2226722f8366e5b2580b83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,4010,27900,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11824555$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Morito, Keiko</creatorcontrib><creatorcontrib>Aomori, Tohru</creatorcontrib><creatorcontrib>Hirose, Toshiharu</creatorcontrib><creatorcontrib>Kinjo, Junei</creatorcontrib><creatorcontrib>Hasegawa, Junichi</creatorcontrib><creatorcontrib>Ogawa, Sumito</creatorcontrib><creatorcontrib>Inoue, Satoshi</creatorcontrib><creatorcontrib>Muramatsu, Masami</creatorcontrib><creatorcontrib>Masamune, Yukito</creatorcontrib><title>Interaction of Phytoestrogens with Estrogen Receptors α and β (II)</title><title>Biological & pharmaceutical bulletin</title><addtitle>Biol Pharm Bull</addtitle><description>We investigated the estrogenic activities of isoflavone derivatives in competition binding assays with human estrogen receptor (hER) α or hER β protein, and in a gene expression assay using a yeast system. Coumestrol binds as strongly as 17β-estradiol to both hERs. Biochanin A, 5-OMe-genistein, formononetin, and tectorigenin bind well to hER β, but significant binding to hER α is only observed with 5-OMe-genistein, formononetin and tectorigenin. The binding of 7-OMe-genistein and irisolidone is poor to both receptors. Among the glucosides, sissotorin binds both receptors and the binding is stronger than genistin. Coumestrol induces transcription as strongly as genistein. Tectorigenin also induces transcription with both hERs. Though biochanin A, 5-OMe-genistein, 7-OMe-genistein, irisolidone and formononetin slightly induce transcription with hER β, they act as antagonists in the induction of transcription by 17β-estradiol. The results show that methylation or glucosidation of isoflavones generally inhibits their phytoestrogenic activities.</description><subject>beta-Galactosidase - biosynthesis</subject><subject>Estrogen Antagonists - pharmacology</subject><subject>Estrogen Receptor alpha</subject><subject>Estrogen Receptor beta</subject><subject>Estrogens, Non-Steroidal - pharmacology</subject><subject>hER isoflavone binding</subject><subject>hER-dependent gene expression</subject><subject>human estrogen receptor (hER) α and β</subject><subject>Humans</subject><subject>isoflavone</subject><subject>Isoflavones - pharmacology</subject><subject>Phytoestrogens</subject><subject>Plant Preparations</subject><subject>Receptors, Estrogen - biosynthesis</subject><subject>Receptors, Estrogen - drug effects</subject><subject>Receptors, Estrogen - genetics</subject><subject>Saccharomyces cerevisiae - genetics</subject><subject>Transcription, Genetic - drug effects</subject><issn>0918-6158</issn><issn>1347-5215</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkM1Kw0AURgdRbK0ufAGZldhF6vxkkulGkFq1UFBE18NkctOmpEmcmSJ9LH2QPpMpSXVzL5fvcLh8CF1SMqIslLdJnYyYGIXyCPUpD-NAMCqOUZ-MqQwiKmQPnTm3IoTEhPFT1KNUslAI0UcPs9KD1cbnVYmrDL8ut74C5221gNLhr9wv8bQ78RsYqH1lHd59Y12mePeDb2az4Tk6yXTh4KLbA_TxOH2fPAfzl6fZ5H4emDCiPsiyNIKYsyQxmeZcyzhOjBbUEG44YYYQJgiEBtKMMRbFjGWSRxGIhAlJEskH6Lr11rb63DRfqnXuDBSFLqHaOBXTkPGxIA04bEFjK-csZKq2-VrbraJE7StTTWWKCRXupVeddJOsIf0nu44a4K4FVs7rBfwB2vrcFHBQ0XY07kNgltoqKPkvcq5-Eg</recordid><startdate>2002</startdate><enddate>2002</enddate><creator>Morito, Keiko</creator><creator>Aomori, Tohru</creator><creator>Hirose, Toshiharu</creator><creator>Kinjo, Junei</creator><creator>Hasegawa, Junichi</creator><creator>Ogawa, Sumito</creator><creator>Inoue, Satoshi</creator><creator>Muramatsu, Masami</creator><creator>Masamune, Yukito</creator><general>The Pharmaceutical Society of Japan</general><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>7X8</scope></search><sort><creationdate>2002</creationdate><title>Interaction of Phytoestrogens with Estrogen Receptors α and β (II)</title><author>Morito, Keiko ; Aomori, Tohru ; Hirose, Toshiharu ; Kinjo, Junei ; Hasegawa, Junichi ; Ogawa, Sumito ; Inoue, Satoshi ; Muramatsu, Masami ; Masamune, Yukito</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c461t-ffd6e732bbcfa33a877bca51c03c302c00250e4cedf2226722f8366e5b2580b83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>beta-Galactosidase - biosynthesis</topic><topic>Estrogen Antagonists - pharmacology</topic><topic>Estrogen Receptor alpha</topic><topic>Estrogen Receptor beta</topic><topic>Estrogens, Non-Steroidal - pharmacology</topic><topic>hER isoflavone binding</topic><topic>hER-dependent gene expression</topic><topic>human estrogen receptor (hER) α and β</topic><topic>Humans</topic><topic>isoflavone</topic><topic>Isoflavones - pharmacology</topic><topic>Phytoestrogens</topic><topic>Plant Preparations</topic><topic>Receptors, Estrogen - biosynthesis</topic><topic>Receptors, Estrogen - drug effects</topic><topic>Receptors, Estrogen - genetics</topic><topic>Saccharomyces cerevisiae - genetics</topic><topic>Transcription, Genetic - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Morito, Keiko</creatorcontrib><creatorcontrib>Aomori, Tohru</creatorcontrib><creatorcontrib>Hirose, Toshiharu</creatorcontrib><creatorcontrib>Kinjo, Junei</creatorcontrib><creatorcontrib>Hasegawa, Junichi</creatorcontrib><creatorcontrib>Ogawa, Sumito</creatorcontrib><creatorcontrib>Inoue, Satoshi</creatorcontrib><creatorcontrib>Muramatsu, Masami</creatorcontrib><creatorcontrib>Masamune, Yukito</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Biological & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Morito, Keiko</au><au>Aomori, Tohru</au><au>Hirose, Toshiharu</au><au>Kinjo, Junei</au><au>Hasegawa, Junichi</au><au>Ogawa, Sumito</au><au>Inoue, Satoshi</au><au>Muramatsu, Masami</au><au>Masamune, Yukito</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Interaction of Phytoestrogens with Estrogen Receptors α and β (II)</atitle><jtitle>Biological & pharmaceutical bulletin</jtitle><addtitle>Biol Pharm Bull</addtitle><date>2002</date><risdate>2002</risdate><volume>25</volume><issue>1</issue><spage>48</spage><epage>52</epage><pages>48-52</pages><issn>0918-6158</issn><eissn>1347-5215</eissn><abstract>We investigated the estrogenic activities of isoflavone derivatives in competition binding assays with human estrogen receptor (hER) α or hER β protein, and in a gene expression assay using a yeast system. Coumestrol binds as strongly as 17β-estradiol to both hERs. Biochanin A, 5-OMe-genistein, formononetin, and tectorigenin bind well to hER β, but significant binding to hER α is only observed with 5-OMe-genistein, formononetin and tectorigenin. The binding of 7-OMe-genistein and irisolidone is poor to both receptors. Among the glucosides, sissotorin binds both receptors and the binding is stronger than genistin. Coumestrol induces transcription as strongly as genistein. Tectorigenin also induces transcription with both hERs. Though biochanin A, 5-OMe-genistein, 7-OMe-genistein, irisolidone and formononetin slightly induce transcription with hER β, they act as antagonists in the induction of transcription by 17β-estradiol. The results show that methylation or glucosidation of isoflavones generally inhibits their phytoestrogenic activities.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>11824555</pmid><doi>10.1248/bpb.25.48</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| source | J-STAGE Free; MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| subjects | beta-Galactosidase - biosynthesis Estrogen Antagonists - pharmacology Estrogen Receptor alpha Estrogen Receptor beta Estrogens, Non-Steroidal - pharmacology hER isoflavone binding hER-dependent gene expression human estrogen receptor (hER) α and β Humans isoflavone Isoflavones - pharmacology Phytoestrogens Plant Preparations Receptors, Estrogen - biosynthesis Receptors, Estrogen - drug effects Receptors, Estrogen - genetics Saccharomyces cerevisiae - genetics Transcription, Genetic - drug effects |
| title | Interaction of Phytoestrogens with Estrogen Receptors α and β (II) |
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