Influence of Anthocyanins, Derivative Pigments and Other Catechol and Pyrogallol-Type Phenolics on Breast Cancer Cell Proliferation
Anthocyanins (cyanidin-3-glucoside (Cy-3-gluc) and delphinidin-3-glucoside (Dp-3-gluc)) and their respective vinylpyranoanthocyanin-catechins (portisins) were studied in order to evaluate the cytotoxicity effect on the estrogen responsive human breast cancer cell line (ER+) MCF-7 and their effect on...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2010-03, Vol.58 (6), p.3785-3792 |
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| creator | Fernandes, Iva Faria, Ana Azevedo, Joana Soares, Susana Calhau, Conceição De Freitas, Victor Mateus, Nuno |
| description | Anthocyanins (cyanidin-3-glucoside (Cy-3-gluc) and delphinidin-3-glucoside (Dp-3-gluc)) and their respective vinylpyranoanthocyanin-catechins (portisins) were studied in order to evaluate the cytotoxicity effect on the estrogen responsive human breast cancer cell line (ER+) MCF-7 and their effect on estrogen receptor (ER-α and ER-β) expression. Other flavonoid classes and phenolic molecules were also tested, aiming to study possible structural features related with these effects. Also, the antiproliferative effect of Cy-3-gluc and Dp-3-gluc was studied by an immunofluorescence assay. Generally, all the anthocyanin pigments studied inhibited, in a dose-dependent manner, the growth of the (ER+) MCF-7. The cytotoxicity effect was higher when cells were treated with Dp-3-gluc and its respective portisin. Altogether, the results point to the ortho trihydroxylated moiety in the phenolic ring as an important structural feature for more potent cytotoxicity effect on MCF-7 cells comparatively to the effect observed with the similar dihydroxylated compounds. In order to elucidate the molecular mechanism involved, expression of estrogen receptor was assayed by RT-PCR and real time RT-PCR. The higher antiproliferative effect observed after cell treatment with Dp-3-gluc was not followed by modification on ER expression. However, the anthocyanin Cy-3-gluc was able to induce a downregulation of ER levels although with no significant effect on MCF-7 proliferation. |
| doi_str_mv | 10.1021/jf903714z |
| format | Article |
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Other flavonoid classes and phenolic molecules were also tested, aiming to study possible structural features related with these effects. Also, the antiproliferative effect of Cy-3-gluc and Dp-3-gluc was studied by an immunofluorescence assay. Generally, all the anthocyanin pigments studied inhibited, in a dose-dependent manner, the growth of the (ER+) MCF-7. The cytotoxicity effect was higher when cells were treated with Dp-3-gluc and its respective portisin. Altogether, the results point to the ortho trihydroxylated moiety in the phenolic ring as an important structural feature for more potent cytotoxicity effect on MCF-7 cells comparatively to the effect observed with the similar dihydroxylated compounds. In order to elucidate the molecular mechanism involved, expression of estrogen receptor was assayed by RT-PCR and real time RT-PCR. The higher antiproliferative effect observed after cell treatment with Dp-3-gluc was not followed by modification on ER expression. However, the anthocyanin Cy-3-gluc was able to induce a downregulation of ER levels although with no significant effect on MCF-7 proliferation.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf903714z</identifier><identifier>PMID: 20170107</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>adenocarcinoma ; anthocyanins ; Anthocyanins - adverse effects ; Anthocyanins - chemistry ; Anthocyanins - pharmacology ; Biological and medical sciences ; breast neoplasms ; Breast Neoplasms - drug therapy ; Breast Neoplasms - genetics ; Breast Neoplasms - metabolism ; Breast Neoplasms - physiopathology ; catechol ; Catechols - adverse effects ; Catechols - chemistry ; Catechols - pharmacology ; cell lines ; cell proliferation ; Cell Proliferation - drug effects ; chemical structure ; cytotoxicity ; dose response ; estrogens ; Female ; flavanols ; flavonoids ; Food Chemistry/Biochemistry ; Food industries ; Fundamental and applied biological sciences. Psychology ; gene expression ; gene expression regulation ; Gene Expression Regulation, Neoplastic - drug effects ; hormone receptors ; human diseases ; Humans ; phenolic compounds ; phytochemicals ; plant pigments ; pyrogallol ; Pyrogallol - adverse effects ; Pyrogallol - analogs & derivatives ; Pyrogallol - pharmacology ; Receptors, Estrogen - genetics ; Receptors, Estrogen - metabolism ; viability</subject><ispartof>Journal of agricultural and food chemistry, 2010-03, Vol.58 (6), p.3785-3792</ispartof><rights>Copyright © 2010 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a461t-1997dbc8901520531cb641e33fb7c4b74f38c8923d2afa193a682bff1b4d7b943</citedby><cites>FETCH-LOGICAL-a461t-1997dbc8901520531cb641e33fb7c4b74f38c8923d2afa193a682bff1b4d7b943</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf903714z$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf903714z$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22546321$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20170107$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fernandes, Iva</creatorcontrib><creatorcontrib>Faria, Ana</creatorcontrib><creatorcontrib>Azevedo, Joana</creatorcontrib><creatorcontrib>Soares, Susana</creatorcontrib><creatorcontrib>Calhau, Conceição</creatorcontrib><creatorcontrib>De Freitas, Victor</creatorcontrib><creatorcontrib>Mateus, Nuno</creatorcontrib><title>Influence of Anthocyanins, Derivative Pigments and Other Catechol and Pyrogallol-Type Phenolics on Breast Cancer Cell Proliferation</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Anthocyanins (cyanidin-3-glucoside (Cy-3-gluc) and delphinidin-3-glucoside (Dp-3-gluc)) and their respective vinylpyranoanthocyanin-catechins (portisins) were studied in order to evaluate the cytotoxicity effect on the estrogen responsive human breast cancer cell line (ER+) MCF-7 and their effect on estrogen receptor (ER-α and ER-β) expression. Other flavonoid classes and phenolic molecules were also tested, aiming to study possible structural features related with these effects. Also, the antiproliferative effect of Cy-3-gluc and Dp-3-gluc was studied by an immunofluorescence assay. Generally, all the anthocyanin pigments studied inhibited, in a dose-dependent manner, the growth of the (ER+) MCF-7. The cytotoxicity effect was higher when cells were treated with Dp-3-gluc and its respective portisin. Altogether, the results point to the ortho trihydroxylated moiety in the phenolic ring as an important structural feature for more potent cytotoxicity effect on MCF-7 cells comparatively to the effect observed with the similar dihydroxylated compounds. In order to elucidate the molecular mechanism involved, expression of estrogen receptor was assayed by RT-PCR and real time RT-PCR. The higher antiproliferative effect observed after cell treatment with Dp-3-gluc was not followed by modification on ER expression. However, the anthocyanin Cy-3-gluc was able to induce a downregulation of ER levels although with no significant effect on MCF-7 proliferation.</description><subject>adenocarcinoma</subject><subject>anthocyanins</subject><subject>Anthocyanins - adverse effects</subject><subject>Anthocyanins - chemistry</subject><subject>Anthocyanins - pharmacology</subject><subject>Biological and medical sciences</subject><subject>breast neoplasms</subject><subject>Breast Neoplasms - drug therapy</subject><subject>Breast Neoplasms - genetics</subject><subject>Breast Neoplasms - metabolism</subject><subject>Breast Neoplasms - physiopathology</subject><subject>catechol</subject><subject>Catechols - adverse effects</subject><subject>Catechols - chemistry</subject><subject>Catechols - pharmacology</subject><subject>cell lines</subject><subject>cell proliferation</subject><subject>Cell Proliferation - drug effects</subject><subject>chemical structure</subject><subject>cytotoxicity</subject><subject>dose response</subject><subject>estrogens</subject><subject>Female</subject><subject>flavanols</subject><subject>flavonoids</subject><subject>Food Chemistry/Biochemistry</subject><subject>Food industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>gene expression</subject><subject>gene expression regulation</subject><subject>Gene Expression Regulation, Neoplastic - drug effects</subject><subject>hormone receptors</subject><subject>human diseases</subject><subject>Humans</subject><subject>phenolic compounds</subject><subject>phytochemicals</subject><subject>plant pigments</subject><subject>pyrogallol</subject><subject>Pyrogallol - adverse effects</subject><subject>Pyrogallol - analogs & derivatives</subject><subject>Pyrogallol - pharmacology</subject><subject>Receptors, Estrogen - genetics</subject><subject>Receptors, Estrogen - metabolism</subject><subject>viability</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkEFv0zAYhi0EYt3gwB8AX9A0iYA_24mT4yiMTZq0Smzn6Itjt6lcu9jJpHLlj-OtZbtwsuT3-V5_fgh5B-wzMA5f1rZhQoH8_YLMoOSsKAHql2TGcljUZQVH5DilNWOsLhV7TY44A8WAqRn5c-Wtm4zXhgZLz_24CnqHfvDpE_1m4nCP43Bv6GJYbowfE0Xf05txZSKd42j0KrjHq8UuhiU6F1xxu9tmfmV8cINONHj6NRpMYx7Ir-Q54xxdxJxaE3N78G_IK4sumbeH84TcXXy_nV8W1zc_rubn1wXKCsYCmkb1na4b9vDHUoDuKglGCNspLTslrahzykXP0SI0Aquad9ZCJ3vVNVKckNN97zaGX5NJY7sZks7roDdhSq0SWWKlOM_k2Z7UMaQUjW23cdhg3LXA2gfl7ZPyzL4_tE7dxvRP5D_HGfh4ADBpdDZmD0N65ngpK8Ehcx_2nMXQ4jJm5u5nbhEMai6hap6bUKd2Habos67_rPQXV-Seyw</recordid><startdate>20100324</startdate><enddate>20100324</enddate><creator>Fernandes, Iva</creator><creator>Faria, Ana</creator><creator>Azevedo, Joana</creator><creator>Soares, Susana</creator><creator>Calhau, Conceição</creator><creator>De Freitas, Victor</creator><creator>Mateus, Nuno</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>IQODW</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>7X8</scope></search><sort><creationdate>20100324</creationdate><title>Influence of Anthocyanins, Derivative Pigments and Other Catechol and Pyrogallol-Type Phenolics on Breast Cancer Cell Proliferation</title><author>Fernandes, Iva ; Faria, Ana ; Azevedo, Joana ; Soares, Susana ; Calhau, Conceição ; De Freitas, Victor ; Mateus, Nuno</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a461t-1997dbc8901520531cb641e33fb7c4b74f38c8923d2afa193a682bff1b4d7b943</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>adenocarcinoma</topic><topic>anthocyanins</topic><topic>Anthocyanins - adverse effects</topic><topic>Anthocyanins - chemistry</topic><topic>Anthocyanins - pharmacology</topic><topic>Biological and medical sciences</topic><topic>breast neoplasms</topic><topic>Breast Neoplasms - drug therapy</topic><topic>Breast Neoplasms - genetics</topic><topic>Breast Neoplasms - metabolism</topic><topic>Breast Neoplasms - physiopathology</topic><topic>catechol</topic><topic>Catechols - adverse effects</topic><topic>Catechols - chemistry</topic><topic>Catechols - pharmacology</topic><topic>cell lines</topic><topic>cell proliferation</topic><topic>Cell Proliferation - drug effects</topic><topic>chemical structure</topic><topic>cytotoxicity</topic><topic>dose response</topic><topic>estrogens</topic><topic>Female</topic><topic>flavanols</topic><topic>flavonoids</topic><topic>Food Chemistry/Biochemistry</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>gene expression</topic><topic>gene expression regulation</topic><topic>Gene Expression Regulation, Neoplastic - drug effects</topic><topic>hormone receptors</topic><topic>human diseases</topic><topic>Humans</topic><topic>phenolic compounds</topic><topic>phytochemicals</topic><topic>plant pigments</topic><topic>pyrogallol</topic><topic>Pyrogallol - adverse effects</topic><topic>Pyrogallol - analogs & derivatives</topic><topic>Pyrogallol - pharmacology</topic><topic>Receptors, Estrogen - genetics</topic><topic>Receptors, Estrogen - metabolism</topic><topic>viability</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fernandes, Iva</creatorcontrib><creatorcontrib>Faria, Ana</creatorcontrib><creatorcontrib>Azevedo, Joana</creatorcontrib><creatorcontrib>Soares, Susana</creatorcontrib><creatorcontrib>Calhau, Conceição</creatorcontrib><creatorcontrib>De Freitas, Victor</creatorcontrib><creatorcontrib>Mateus, Nuno</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><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>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fernandes, Iva</au><au>Faria, Ana</au><au>Azevedo, Joana</au><au>Soares, Susana</au><au>Calhau, Conceição</au><au>De Freitas, Victor</au><au>Mateus, Nuno</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Influence of Anthocyanins, Derivative Pigments and Other Catechol and Pyrogallol-Type Phenolics on Breast Cancer Cell Proliferation</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2010-03-24</date><risdate>2010</risdate><volume>58</volume><issue>6</issue><spage>3785</spage><epage>3792</epage><pages>3785-3792</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>Anthocyanins (cyanidin-3-glucoside (Cy-3-gluc) and delphinidin-3-glucoside (Dp-3-gluc)) and their respective vinylpyranoanthocyanin-catechins (portisins) were studied in order to evaluate the cytotoxicity effect on the estrogen responsive human breast cancer cell line (ER+) MCF-7 and their effect on estrogen receptor (ER-α and ER-β) expression. Other flavonoid classes and phenolic molecules were also tested, aiming to study possible structural features related with these effects. Also, the antiproliferative effect of Cy-3-gluc and Dp-3-gluc was studied by an immunofluorescence assay. Generally, all the anthocyanin pigments studied inhibited, in a dose-dependent manner, the growth of the (ER+) MCF-7. The cytotoxicity effect was higher when cells were treated with Dp-3-gluc and its respective portisin. Altogether, the results point to the ortho trihydroxylated moiety in the phenolic ring as an important structural feature for more potent cytotoxicity effect on MCF-7 cells comparatively to the effect observed with the similar dihydroxylated compounds. In order to elucidate the molecular mechanism involved, expression of estrogen receptor was assayed by RT-PCR and real time RT-PCR. The higher antiproliferative effect observed after cell treatment with Dp-3-gluc was not followed by modification on ER expression. However, the anthocyanin Cy-3-gluc was able to induce a downregulation of ER levels although with no significant effect on MCF-7 proliferation.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>20170107</pmid><doi>10.1021/jf903714z</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | adenocarcinoma anthocyanins Anthocyanins - adverse effects Anthocyanins - chemistry Anthocyanins - pharmacology Biological and medical sciences breast neoplasms Breast Neoplasms - drug therapy Breast Neoplasms - genetics Breast Neoplasms - metabolism Breast Neoplasms - physiopathology catechol Catechols - adverse effects Catechols - chemistry Catechols - pharmacology cell lines cell proliferation Cell Proliferation - drug effects chemical structure cytotoxicity dose response estrogens Female flavanols flavonoids Food Chemistry/Biochemistry Food industries Fundamental and applied biological sciences. Psychology gene expression gene expression regulation Gene Expression Regulation, Neoplastic - drug effects hormone receptors human diseases Humans phenolic compounds phytochemicals plant pigments pyrogallol Pyrogallol - adverse effects Pyrogallol - analogs & derivatives Pyrogallol - pharmacology Receptors, Estrogen - genetics Receptors, Estrogen - metabolism viability |
| title | Influence of Anthocyanins, Derivative Pigments and Other Catechol and Pyrogallol-Type Phenolics on Breast Cancer Cell Proliferation |
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