Synthesis and evaluation of cytotoxic effects of hanultarin and its derivatives
One of the known cytotoxic lignans is (−)-1- O-feruloyl-secoisolariciresinol designated as hanultarin, which was isolated from the seeds of Trichosanthes kirilowii. In this Letter, we described the first synthesis of 1- O-feruloyl-secoisolariciresinol, 1,4- O-diferuloyl-secoisolariceresinol and thei...
Gespeichert in:
| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2011-11, Vol.21 (21), p.6245-6248 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 6248 |
|---|---|
| container_issue | 21 |
| container_start_page | 6245 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 21 |
| creator | Lee, Eunyoung Ahamed, V.S. Jamal Kumar, Mahto Sanjeev Rhee, Seog Woo Moon, Surk-Sik Hong, In Seok |
| description | One of the known cytotoxic lignans is (−)-1-
O-feruloyl-secoisolariciresinol designated as hanultarin, which was isolated from the seeds of
Trichosanthes kirilowii. In this Letter, we described the first synthesis of 1-
O-feruloyl-secoisolariciresinol, 1,4-
O-diferuloyl-secoisolariceresinol and their analogues. The cytotoxicities of these compounds were evaluated against several cancer cell lines. Interestingly, we found that the feruloyl diester derivative of secoisolariciresinol was the most active cytotoxic compound against all the cancer cells tested in this experiment. The IC
50 values of the1,4-
O-diferuloyl-secoisolariceresinol were in the range of 7.1–9.8
μM except one cell line. In considering that both ferulic acid and secoisolariciresinol are commonly found in many plants and have no cytotoxicity, this finding is remarkable in that simple covalent bonds between the ferulic acid and secoisolariciresinol cause a cytotoxic effect. |
| doi_str_mv | 10.1016/j.bmcl.2011.09.014 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_904498619</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0960894X11012492</els_id><sourcerecordid>904498619</sourcerecordid><originalsourceid>FETCH-LOGICAL-c507t-8fed6bd5a39595619ac82e4955aaaca1d0308926d21ac9a4a17ea97e8dd3b59d3</originalsourceid><addsrcrecordid>eNqNkU1r3DAQhkVJaTZp_0APrS8lJ7uSLHktyKWE5gMCOSSB3sSsNE60eK1Uspfuv89sdpPeSk-C4XlfSc8w9lnwSnDRfF9Wi5XrK8mFqLipuFDv2EyoRpW14vqAzbhpeNka9euQHeW85ERwpT6wQymMbrWSM3ZzuxnGR8whFzD4AtfQTzCGOBSxK9xmjGP8E1yBXYduzNvhIwxTP0IKw0si0NRjCmtKrTF_ZO876DN-2p_H7P78593ZZXl9c3F19uO6dJrPx7Lt0DcLr6E22uhGGHCtRGW0BgAHwvOat0Y2XgpwBhSIOYKZY-t9vdDG18fsZNf7lOLvCfNoVyE77HsYME7ZGvqoaan4f0gSKKQkUu5Il2LOCTv7lMIK0sYKbrfG7dJujdutccuNJZ8U-rKvnxYr9G-RV8UEfNsDkB30XYLBhfyXU41ppRDEfd1xHUQLD4mY-1u6SdPaaq2aORGnOwJJ7DpgstkFHBz6kGg71sfwr5c-A3mAqJg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>904011122</pqid></control><display><type>article</type><title>Synthesis and evaluation of cytotoxic effects of hanultarin and its derivatives</title><source>MEDLINE</source><source>Elsevier ScienceDirect Journals</source><creator>Lee, Eunyoung ; Ahamed, V.S. Jamal ; Kumar, Mahto Sanjeev ; Rhee, Seog Woo ; Moon, Surk-Sik ; Hong, In Seok</creator><creatorcontrib>Lee, Eunyoung ; Ahamed, V.S. Jamal ; Kumar, Mahto Sanjeev ; Rhee, Seog Woo ; Moon, Surk-Sik ; Hong, In Seok</creatorcontrib><description>One of the known cytotoxic lignans is (−)-1-
O-feruloyl-secoisolariciresinol designated as hanultarin, which was isolated from the seeds of
Trichosanthes kirilowii. In this Letter, we described the first synthesis of 1-
O-feruloyl-secoisolariciresinol, 1,4-
O-diferuloyl-secoisolariceresinol and their analogues. The cytotoxicities of these compounds were evaluated against several cancer cell lines. Interestingly, we found that the feruloyl diester derivative of secoisolariciresinol was the most active cytotoxic compound against all the cancer cells tested in this experiment. The IC
50 values of the1,4-
O-diferuloyl-secoisolariceresinol were in the range of 7.1–9.8
μM except one cell line. In considering that both ferulic acid and secoisolariciresinol are commonly found in many plants and have no cytotoxicity, this finding is remarkable in that simple covalent bonds between the ferulic acid and secoisolariciresinol cause a cytotoxic effect.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2011.09.014</identifier><identifier>PMID: 21958542</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>1,4- O-Diferuloylsecoisolariciresinol ; Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - pharmacology ; Biological and medical sciences ; Cell Line, Tumor ; chemistry ; Cytotoxic lignans ; Cytotoxicity ; Drug Screening Assays, Antitumor ; ferulic acid ; General aspects ; Hanultarin ; Humans ; Immunocytochemical analysis ; Inhibitory Concentration 50 ; lignans ; Lignans - chemical synthesis ; Lignans - pharmacology ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Medical sciences ; Pharmacology. Drug treatments ; seeds ; Spectroscopy, Fourier Transform Infrared ; Trichosanthes kirilowii</subject><ispartof>Bioorganic & medicinal chemistry letters, 2011-11, Vol.21 (21), p.6245-6248</ispartof><rights>2011 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c507t-8fed6bd5a39595619ac82e4955aaaca1d0308926d21ac9a4a17ea97e8dd3b59d3</citedby><cites>FETCH-LOGICAL-c507t-8fed6bd5a39595619ac82e4955aaaca1d0308926d21ac9a4a17ea97e8dd3b59d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2011.09.014$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,45974</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24698211$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21958542$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lee, Eunyoung</creatorcontrib><creatorcontrib>Ahamed, V.S. Jamal</creatorcontrib><creatorcontrib>Kumar, Mahto Sanjeev</creatorcontrib><creatorcontrib>Rhee, Seog Woo</creatorcontrib><creatorcontrib>Moon, Surk-Sik</creatorcontrib><creatorcontrib>Hong, In Seok</creatorcontrib><title>Synthesis and evaluation of cytotoxic effects of hanultarin and its derivatives</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>One of the known cytotoxic lignans is (−)-1-
O-feruloyl-secoisolariciresinol designated as hanultarin, which was isolated from the seeds of
Trichosanthes kirilowii. In this Letter, we described the first synthesis of 1-
O-feruloyl-secoisolariciresinol, 1,4-
O-diferuloyl-secoisolariceresinol and their analogues. The cytotoxicities of these compounds were evaluated against several cancer cell lines. Interestingly, we found that the feruloyl diester derivative of secoisolariciresinol was the most active cytotoxic compound against all the cancer cells tested in this experiment. The IC
50 values of the1,4-
O-diferuloyl-secoisolariceresinol were in the range of 7.1–9.8
μM except one cell line. In considering that both ferulic acid and secoisolariciresinol are commonly found in many plants and have no cytotoxicity, this finding is remarkable in that simple covalent bonds between the ferulic acid and secoisolariciresinol cause a cytotoxic effect.</description><subject>1,4- O-Diferuloylsecoisolariciresinol</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor</subject><subject>chemistry</subject><subject>Cytotoxic lignans</subject><subject>Cytotoxicity</subject><subject>Drug Screening Assays, Antitumor</subject><subject>ferulic acid</subject><subject>General aspects</subject><subject>Hanultarin</subject><subject>Humans</subject><subject>Immunocytochemical analysis</subject><subject>Inhibitory Concentration 50</subject><subject>lignans</subject><subject>Lignans - chemical synthesis</subject><subject>Lignans - pharmacology</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Medical sciences</subject><subject>Pharmacology. Drug treatments</subject><subject>seeds</subject><subject>Spectroscopy, Fourier Transform Infrared</subject><subject>Trichosanthes kirilowii</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkU1r3DAQhkVJaTZp_0APrS8lJ7uSLHktyKWE5gMCOSSB3sSsNE60eK1Uspfuv89sdpPeSk-C4XlfSc8w9lnwSnDRfF9Wi5XrK8mFqLipuFDv2EyoRpW14vqAzbhpeNka9euQHeW85ERwpT6wQymMbrWSM3ZzuxnGR8whFzD4AtfQTzCGOBSxK9xmjGP8E1yBXYduzNvhIwxTP0IKw0si0NRjCmtKrTF_ZO876DN-2p_H7P78593ZZXl9c3F19uO6dJrPx7Lt0DcLr6E22uhGGHCtRGW0BgAHwvOat0Y2XgpwBhSIOYKZY-t9vdDG18fsZNf7lOLvCfNoVyE77HsYME7ZGvqoaan4f0gSKKQkUu5Il2LOCTv7lMIK0sYKbrfG7dJujdutccuNJZ8U-rKvnxYr9G-RV8UEfNsDkB30XYLBhfyXU41ppRDEfd1xHUQLD4mY-1u6SdPaaq2aORGnOwJJ7DpgstkFHBz6kGg71sfwr5c-A3mAqJg</recordid><startdate>20111101</startdate><enddate>20111101</enddate><creator>Lee, Eunyoung</creator><creator>Ahamed, V.S. Jamal</creator><creator>Kumar, Mahto Sanjeev</creator><creator>Rhee, Seog Woo</creator><creator>Moon, Surk-Sik</creator><creator>Hong, In Seok</creator><general>Elsevier Ltd</general><general>Elsevier</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><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20111101</creationdate><title>Synthesis and evaluation of cytotoxic effects of hanultarin and its derivatives</title><author>Lee, Eunyoung ; Ahamed, V.S. Jamal ; Kumar, Mahto Sanjeev ; Rhee, Seog Woo ; Moon, Surk-Sik ; Hong, In Seok</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c507t-8fed6bd5a39595619ac82e4955aaaca1d0308926d21ac9a4a17ea97e8dd3b59d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>1,4- O-Diferuloylsecoisolariciresinol</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor</topic><topic>chemistry</topic><topic>Cytotoxic lignans</topic><topic>Cytotoxicity</topic><topic>Drug Screening Assays, Antitumor</topic><topic>ferulic acid</topic><topic>General aspects</topic><topic>Hanultarin</topic><topic>Humans</topic><topic>Immunocytochemical analysis</topic><topic>Inhibitory Concentration 50</topic><topic>lignans</topic><topic>Lignans - chemical synthesis</topic><topic>Lignans - pharmacology</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Medical sciences</topic><topic>Pharmacology. Drug treatments</topic><topic>seeds</topic><topic>Spectroscopy, Fourier Transform Infrared</topic><topic>Trichosanthes kirilowii</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lee, Eunyoung</creatorcontrib><creatorcontrib>Ahamed, V.S. Jamal</creatorcontrib><creatorcontrib>Kumar, Mahto Sanjeev</creatorcontrib><creatorcontrib>Rhee, Seog Woo</creatorcontrib><creatorcontrib>Moon, Surk-Sik</creatorcontrib><creatorcontrib>Hong, In Seok</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><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lee, Eunyoung</au><au>Ahamed, V.S. Jamal</au><au>Kumar, Mahto Sanjeev</au><au>Rhee, Seog Woo</au><au>Moon, Surk-Sik</au><au>Hong, In Seok</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and evaluation of cytotoxic effects of hanultarin and its derivatives</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2011-11-01</date><risdate>2011</risdate><volume>21</volume><issue>21</issue><spage>6245</spage><epage>6248</epage><pages>6245-6248</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>One of the known cytotoxic lignans is (−)-1-
O-feruloyl-secoisolariciresinol designated as hanultarin, which was isolated from the seeds of
Trichosanthes kirilowii. In this Letter, we described the first synthesis of 1-
O-feruloyl-secoisolariciresinol, 1,4-
O-diferuloyl-secoisolariceresinol and their analogues. The cytotoxicities of these compounds were evaluated against several cancer cell lines. Interestingly, we found that the feruloyl diester derivative of secoisolariciresinol was the most active cytotoxic compound against all the cancer cells tested in this experiment. The IC
50 values of the1,4-
O-diferuloyl-secoisolariceresinol were in the range of 7.1–9.8
μM except one cell line. In considering that both ferulic acid and secoisolariciresinol are commonly found in many plants and have no cytotoxicity, this finding is remarkable in that simple covalent bonds between the ferulic acid and secoisolariciresinol cause a cytotoxic effect.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>21958542</pmid><doi>10.1016/j.bmcl.2011.09.014</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2011-11, Vol.21 (21), p.6245-6248 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_904498619 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | 1,4- O-Diferuloylsecoisolariciresinol Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology Biological and medical sciences Cell Line, Tumor chemistry Cytotoxic lignans Cytotoxicity Drug Screening Assays, Antitumor ferulic acid General aspects Hanultarin Humans Immunocytochemical analysis Inhibitory Concentration 50 lignans Lignans - chemical synthesis Lignans - pharmacology Magnetic Resonance Spectroscopy Mass Spectrometry Medical sciences Pharmacology. Drug treatments seeds Spectroscopy, Fourier Transform Infrared Trichosanthes kirilowii |
| title | Synthesis and evaluation of cytotoxic effects of hanultarin and its derivatives |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-22T07%3A50%3A47IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20and%20evaluation%20of%20cytotoxic%20effects%20of%20hanultarin%20and%20its%20derivatives&rft.jtitle=Bioorganic%20&%20medicinal%20chemistry%20letters&rft.au=Lee,%20Eunyoung&rft.date=2011-11-01&rft.volume=21&rft.issue=21&rft.spage=6245&rft.epage=6248&rft.pages=6245-6248&rft.issn=0960-894X&rft.eissn=1464-3405&rft_id=info:doi/10.1016/j.bmcl.2011.09.014&rft_dat=%3Cproquest_cross%3E904498619%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=904011122&rft_id=info:pmid/21958542&rft_els_id=S0960894X11012492&rfr_iscdi=true |