A new α-pyrone from Arthrinium pseudosinense culture medium and its estrogenic activity in MCF-7 cells
A new α -pyrone analog, arthrifuranone A ( 1 ) was isolated from an EtOAc-extract of Arthrinium pseudosinense culture medium. The isolation workflow was guided by a Molecular Networking-based dereplication strategy. The chemical structure of the new compound was elucidated using MS and NMR spectrosc...
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| Veröffentlicht in: | Journal of antibiotics 2021-12, Vol.74 (12), p.893-897 |
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| container_issue | 12 |
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| container_title | Journal of antibiotics |
| container_volume | 74 |
| creator | Kwon, Haeun Nguyen, Quynh Nhu Na, Myung Woo Kim, Ki Hyun Guo, Yuanqiang Yim, Joung Han Shim, Sang Hee Kim, Jae-Jin Kang, Ki Sung Lee, Dongho |
| description | A new
α
-pyrone analog, arthrifuranone A (
1
) was isolated from an EtOAc-extract of
Arthrinium pseudosinense
culture medium. The isolation workflow was guided by a Molecular Networking-based dereplication strategy. The chemical structure of the new compound was elucidated using MS and NMR spectroscopic techniques, and the absolute configuration was established by the Mosher’s method and gauge-including atomic orbital NMR chemical shift calculations, followed by DP4 + analysis. The isolated compound was evaluated for its estrogenic activity using the MCF-7 estrogen responsive human breast cancer cells. Compound
1
showed estrogenic activity by increasing the proliferation of MCF-7 cells at the concentration of 3.125 μM via phosphorylation of estrogen receptor-
α
. |
| doi_str_mv | 10.1038/s41429-021-00473-8 |
| format | Article |
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α
-pyrone analog, arthrifuranone A (
1
) was isolated from an EtOAc-extract of
Arthrinium pseudosinense
culture medium. The isolation workflow was guided by a Molecular Networking-based dereplication strategy. The chemical structure of the new compound was elucidated using MS and NMR spectroscopic techniques, and the absolute configuration was established by the Mosher’s method and gauge-including atomic orbital NMR chemical shift calculations, followed by DP4 + analysis. The isolated compound was evaluated for its estrogenic activity using the MCF-7 estrogen responsive human breast cancer cells. Compound
1
showed estrogenic activity by increasing the proliferation of MCF-7 cells at the concentration of 3.125 μM via phosphorylation of estrogen receptor-
α
.</description><identifier>ISSN: 0021-8820</identifier><identifier>EISSN: 1881-1469</identifier><identifier>DOI: 10.1038/s41429-021-00473-8</identifier><identifier>PMID: 34497375</identifier><language>eng</language><publisher>London: Nature Publishing Group UK</publisher><subject>101/58 ; 631/154/433 ; 631/92/349 ; 82/16 ; 82/58 ; Absolute configuration ; Arthrinium ; Ascomycota - metabolism ; Bacteriology ; Biomedical and Life Sciences ; Bioorganic Chemistry ; Breast cancer ; Breast Neoplasms - metabolism ; Brief Communication ; Cell culture ; Cell proliferation ; Cell Proliferation - drug effects ; Chemical equilibrium ; Culture ; Culture media ; Estrogen Receptor alpha - drug effects ; Estrogen Receptor alpha - metabolism ; Estrogen receptors ; Estrogenic activity ; Estrogens ; Estrogens - chemistry ; Estrogens - isolation & purification ; Estrogens - pharmacology ; Female ; Humans ; Life Sciences ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; MCF-7 Cells ; Medicinal Chemistry ; Microbiology ; Molecular structure ; NMR ; Nuclear magnetic resonance ; Organic Chemistry ; Phosphorylation ; Pyrones - chemistry ; Pyrones - isolation & purification ; Pyrones - pharmacology ; Workflow ; Xenoestrogens</subject><ispartof>Journal of antibiotics, 2021-12, Vol.74 (12), p.893-897</ispartof><rights>The Author(s), under exclusive licence to the Japan Antibiotics Research Association 2021</rights><rights>2021. The Author(s), under exclusive licence to the Japan Antibiotics Research Association.</rights><rights>The Author(s), under exclusive licence to the Japan Antibiotics Research Association 2021.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c399t-cc7d902c4a2831de2550ae65f3b4d65012db4a2f0aafd1023ebc9b79b2580b1a3</citedby><cites>FETCH-LOGICAL-c399t-cc7d902c4a2831de2550ae65f3b4d65012db4a2f0aafd1023ebc9b79b2580b1a3</cites><orcidid>0000-0002-5285-9138 ; 0000-0003-2553-3690</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34497375$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kwon, Haeun</creatorcontrib><creatorcontrib>Nguyen, Quynh Nhu</creatorcontrib><creatorcontrib>Na, Myung Woo</creatorcontrib><creatorcontrib>Kim, Ki Hyun</creatorcontrib><creatorcontrib>Guo, Yuanqiang</creatorcontrib><creatorcontrib>Yim, Joung Han</creatorcontrib><creatorcontrib>Shim, Sang Hee</creatorcontrib><creatorcontrib>Kim, Jae-Jin</creatorcontrib><creatorcontrib>Kang, Ki Sung</creatorcontrib><creatorcontrib>Lee, Dongho</creatorcontrib><title>A new α-pyrone from Arthrinium pseudosinense culture medium and its estrogenic activity in MCF-7 cells</title><title>Journal of antibiotics</title><addtitle>J Antibiot</addtitle><addtitle>J Antibiot (Tokyo)</addtitle><description>A new
α
-pyrone analog, arthrifuranone A (
1
) was isolated from an EtOAc-extract of
Arthrinium pseudosinense
culture medium. The isolation workflow was guided by a Molecular Networking-based dereplication strategy. The chemical structure of the new compound was elucidated using MS and NMR spectroscopic techniques, and the absolute configuration was established by the Mosher’s method and gauge-including atomic orbital NMR chemical shift calculations, followed by DP4 + analysis. The isolated compound was evaluated for its estrogenic activity using the MCF-7 estrogen responsive human breast cancer cells. Compound
1
showed estrogenic activity by increasing the proliferation of MCF-7 cells at the concentration of 3.125 μM via phosphorylation of estrogen receptor-
α
.</description><subject>101/58</subject><subject>631/154/433</subject><subject>631/92/349</subject><subject>82/16</subject><subject>82/58</subject><subject>Absolute configuration</subject><subject>Arthrinium</subject><subject>Ascomycota - metabolism</subject><subject>Bacteriology</subject><subject>Biomedical and Life Sciences</subject><subject>Bioorganic Chemistry</subject><subject>Breast cancer</subject><subject>Breast Neoplasms - metabolism</subject><subject>Brief Communication</subject><subject>Cell culture</subject><subject>Cell proliferation</subject><subject>Cell Proliferation - drug effects</subject><subject>Chemical equilibrium</subject><subject>Culture</subject><subject>Culture media</subject><subject>Estrogen Receptor alpha - drug effects</subject><subject>Estrogen Receptor alpha - metabolism</subject><subject>Estrogen receptors</subject><subject>Estrogenic activity</subject><subject>Estrogens</subject><subject>Estrogens - chemistry</subject><subject>Estrogens - isolation & purification</subject><subject>Estrogens - pharmacology</subject><subject>Female</subject><subject>Humans</subject><subject>Life Sciences</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>MCF-7 Cells</subject><subject>Medicinal Chemistry</subject><subject>Microbiology</subject><subject>Molecular structure</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic Chemistry</subject><subject>Phosphorylation</subject><subject>Pyrones - chemistry</subject><subject>Pyrones - isolation & purification</subject><subject>Pyrones - pharmacology</subject><subject>Workflow</subject><subject>Xenoestrogens</subject><issn>0021-8820</issn><issn>1881-1469</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>BENPR</sourceid><recordid>eNp9kc1uEzEUhS0EomnhBVggS2zYuFz_TGwvo4i2SEVsYG15PHdSVxlPsGeK8li8CM-E07RF6oKVr3S-e3x0LiHvOJxzkOZTUVwJy0BwBqC0ZOYFWXBjOONqaV-SBRwkYwSckNNSbgGkltq8JidSKVvHZkE2K5rwF_3zm-32eUxI-zwOdJWnmxxTnAe6Kzh3Y4kJU0Ea5u00Z6QDdgfRp47GqVAsUx43mGKgPkzxLk57GhP9ur5gmgbcbssb8qr324JvH94z8uPi8_f1Fbv-dvllvbpmQVo7sRB0Z0EE5YWRvEPRNOBx2fSyVd2yAS66tmo9eN93HITENthW21Y0Blru5Rn5ePTd5fHnXHO5IZZDAp9wnIsTjebQCNCqoh-eobfjnFNN58SyVmUFcF0pcaRCHkvJ2LtdjoPPe8fBHc7gjmdwtWt3fwZn6tL7B-u5rVU9rTz2XgF5BEqV0gbzv7__Y_sXXliTgQ</recordid><startdate>20211201</startdate><enddate>20211201</enddate><creator>Kwon, Haeun</creator><creator>Nguyen, Quynh Nhu</creator><creator>Na, Myung Woo</creator><creator>Kim, Ki Hyun</creator><creator>Guo, Yuanqiang</creator><creator>Yim, Joung Han</creator><creator>Shim, Sang Hee</creator><creator>Kim, Jae-Jin</creator><creator>Kang, Ki Sung</creator><creator>Lee, Dongho</creator><general>Nature Publishing Group UK</general><general>Nature Publishing Group</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>3V.</scope><scope>7QL</scope><scope>7T5</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>88I</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>H94</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>M7P</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-5285-9138</orcidid><orcidid>https://orcid.org/0000-0003-2553-3690</orcidid></search><sort><creationdate>20211201</creationdate><title>A new α-pyrone from Arthrinium pseudosinense culture medium and its estrogenic activity in MCF-7 cells</title><author>Kwon, Haeun ; Nguyen, Quynh Nhu ; Na, Myung Woo ; Kim, Ki Hyun ; Guo, Yuanqiang ; Yim, Joung Han ; Shim, Sang Hee ; Kim, Jae-Jin ; Kang, Ki Sung ; Lee, Dongho</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c399t-cc7d902c4a2831de2550ae65f3b4d65012db4a2f0aafd1023ebc9b79b2580b1a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>101/58</topic><topic>631/154/433</topic><topic>631/92/349</topic><topic>82/16</topic><topic>82/58</topic><topic>Absolute configuration</topic><topic>Arthrinium</topic><topic>Ascomycota - 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Academic</collection><jtitle>Journal of antibiotics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kwon, Haeun</au><au>Nguyen, Quynh Nhu</au><au>Na, Myung Woo</au><au>Kim, Ki Hyun</au><au>Guo, Yuanqiang</au><au>Yim, Joung Han</au><au>Shim, Sang Hee</au><au>Kim, Jae-Jin</au><au>Kang, Ki Sung</au><au>Lee, Dongho</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A new α-pyrone from Arthrinium pseudosinense culture medium and its estrogenic activity in MCF-7 cells</atitle><jtitle>Journal of antibiotics</jtitle><stitle>J Antibiot</stitle><addtitle>J Antibiot (Tokyo)</addtitle><date>2021-12-01</date><risdate>2021</risdate><volume>74</volume><issue>12</issue><spage>893</spage><epage>897</epage><pages>893-897</pages><issn>0021-8820</issn><eissn>1881-1469</eissn><abstract>A new
α
-pyrone analog, arthrifuranone A (
1
) was isolated from an EtOAc-extract of
Arthrinium pseudosinense
culture medium. The isolation workflow was guided by a Molecular Networking-based dereplication strategy. The chemical structure of the new compound was elucidated using MS and NMR spectroscopic techniques, and the absolute configuration was established by the Mosher’s method and gauge-including atomic orbital NMR chemical shift calculations, followed by DP4 + analysis. The isolated compound was evaluated for its estrogenic activity using the MCF-7 estrogen responsive human breast cancer cells. Compound
1
showed estrogenic activity by increasing the proliferation of MCF-7 cells at the concentration of 3.125 μM via phosphorylation of estrogen receptor-
α
.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><pmid>34497375</pmid><doi>10.1038/s41429-021-00473-8</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-5285-9138</orcidid><orcidid>https://orcid.org/0000-0003-2553-3690</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0021-8820 |
| ispartof | Journal of antibiotics, 2021-12, Vol.74 (12), p.893-897 |
| issn | 0021-8820 1881-1469 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2571052074 |
| source | MEDLINE; Alma/SFX Local Collection |
| subjects | 101/58 631/154/433 631/92/349 82/16 82/58 Absolute configuration Arthrinium Ascomycota - metabolism Bacteriology Biomedical and Life Sciences Bioorganic Chemistry Breast cancer Breast Neoplasms - metabolism Brief Communication Cell culture Cell proliferation Cell Proliferation - drug effects Chemical equilibrium Culture Culture media Estrogen Receptor alpha - drug effects Estrogen Receptor alpha - metabolism Estrogen receptors Estrogenic activity Estrogens Estrogens - chemistry Estrogens - isolation & purification Estrogens - pharmacology Female Humans Life Sciences Magnetic Resonance Spectroscopy Mass Spectrometry MCF-7 Cells Medicinal Chemistry Microbiology Molecular structure NMR Nuclear magnetic resonance Organic Chemistry Phosphorylation Pyrones - chemistry Pyrones - isolation & purification Pyrones - pharmacology Workflow Xenoestrogens |
| title | A new α-pyrone from Arthrinium pseudosinense culture medium and its estrogenic activity in MCF-7 cells |
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