Absolute configuration of podophyllotoxone and its inhibitory activity against human prostate cancer cells
Podophyllotoxone (1) was isolated from the roots of Dysosma versipellis. The structure was determined by spectroscopic analysis in combination with single-crystal X-ray analysis. The absolute configuration of compound 1 was assigned based on the Flack parameter. It showed significant inhibitory acti...
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| Veröffentlicht in: | Chinese journal of natural medicines 2015-01, Vol.13 (1), p.59-64 |
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| container_title | Chinese journal of natural medicines |
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| creator | LI, Juan FENG, Juan LUO, Cheng Herman, Ho-Yung Sung JIANG, Ren-Wang |
| description | Podophyllotoxone (1) was isolated from the roots of Dysosma versipellis. The structure was determined by spectroscopic analysis in combination with single-crystal X-ray analysis. The absolute configuration of compound 1 was assigned based on the Flack parameter. It showed significant inhibitory activities against human prostate cancer cells PC3 and DU145 with IC50 values being 14.7 and 20.6 μmol·L−1, respectively. It also arrested the cells at G2/M phase. Tubulin polymerization assay showed that it inhibited the tubulin polymerization in a dose-dependent manner, and molecular docking analysis revealed a different binding mode with tubulin as compared with those known tubulin inhibitors. |
| doi_str_mv | 10.1016/S1875-5364(15)60007-3 |
| format | Article |
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The structure was determined by spectroscopic analysis in combination with single-crystal X-ray analysis. The absolute configuration of compound 1 was assigned based on the Flack parameter. It showed significant inhibitory activities against human prostate cancer cells PC3 and DU145 with IC50 values being 14.7 and 20.6 μmol·L−1, respectively. It also arrested the cells at G2/M phase. Tubulin polymerization assay showed that it inhibited the tubulin polymerization in a dose-dependent manner, and molecular docking analysis revealed a different binding mode with tubulin as compared with those known tubulin inhibitors.</description><identifier>ISSN: 1875-5364</identifier><identifier>EISSN: 1875-5364</identifier><identifier>DOI: 10.1016/S1875-5364(15)60007-3</identifier><identifier>PMID: 25660289</identifier><language>eng</language><publisher>China: Elsevier B.V</publisher><subject>Absolute configuration ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Berberidaceae - chemistry ; Cell Line, Tumor ; Dose-Response Relationship, Drug ; G2 Phase - drug effects ; Humans ; Hydrogen Bonding - drug effects ; Male ; Molecular Conformation ; Molecular docking ; Molecular Docking Simulation ; Phytotherapy ; Plant Extracts - chemistry ; Plant Extracts - pharmacology ; Plant Roots - chemistry ; Podophyllotoxin - chemistry ; Podophyllotoxin - pharmacology ; Podophyllotoxone ; Polymerization ; Prostate cancer ; Prostatic Neoplasms - drug therapy ; Tubulin ; Tubulin - drug effects ; Tubulin Modulators - pharmacology</subject><ispartof>Chinese journal of natural medicines, 2015-01, Vol.13 (1), p.59-64</ispartof><rights>2015 China Pharmaceutical University</rights><rights>Copyright © 2015 China Pharmaceutical University. 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All rights reserved.</rights><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c365t-b3a4bf0bec70f84ce62778aae49496d1d762d50487a68ad84651e68586bdf8b83</citedby><cites>FETCH-LOGICAL-c365t-b3a4bf0bec70f84ce62778aae49496d1d762d50487a68ad84651e68586bdf8b83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S1875-5364(15)60007-3$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25660289$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>LI, Juan</creatorcontrib><creatorcontrib>FENG, Juan</creatorcontrib><creatorcontrib>LUO, Cheng</creatorcontrib><creatorcontrib>Herman, Ho-Yung Sung</creatorcontrib><creatorcontrib>JIANG, Ren-Wang</creatorcontrib><title>Absolute configuration of podophyllotoxone and its inhibitory activity against human prostate cancer cells</title><title>Chinese journal of natural medicines</title><addtitle>Chin J Nat Med</addtitle><description>Podophyllotoxone (1) was isolated from the roots of Dysosma versipellis. The structure was determined by spectroscopic analysis in combination with single-crystal X-ray analysis. The absolute configuration of compound 1 was assigned based on the Flack parameter. It showed significant inhibitory activities against human prostate cancer cells PC3 and DU145 with IC50 values being 14.7 and 20.6 μmol·L−1, respectively. It also arrested the cells at G2/M phase. Tubulin polymerization assay showed that it inhibited the tubulin polymerization in a dose-dependent manner, and molecular docking analysis revealed a different binding mode with tubulin as compared with those known tubulin inhibitors.</description><subject>Absolute configuration</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Berberidaceae - chemistry</subject><subject>Cell Line, Tumor</subject><subject>Dose-Response Relationship, Drug</subject><subject>G2 Phase - drug effects</subject><subject>Humans</subject><subject>Hydrogen Bonding - drug effects</subject><subject>Male</subject><subject>Molecular Conformation</subject><subject>Molecular docking</subject><subject>Molecular Docking Simulation</subject><subject>Phytotherapy</subject><subject>Plant Extracts - chemistry</subject><subject>Plant Extracts - pharmacology</subject><subject>Plant Roots - chemistry</subject><subject>Podophyllotoxin - chemistry</subject><subject>Podophyllotoxin - pharmacology</subject><subject>Podophyllotoxone</subject><subject>Polymerization</subject><subject>Prostate cancer</subject><subject>Prostatic Neoplasms - drug therapy</subject><subject>Tubulin</subject><subject>Tubulin - drug effects</subject><subject>Tubulin Modulators - pharmacology</subject><issn>1875-5364</issn><issn>1875-5364</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE9PAyEQxYnRqKl-BA1HPaxCWVh6Mo3xX9LEg3omLMxazBYqsMZ-e2mrxpunmUzevHnzQ-iEkgtKqLh8orLhFWeiPqP8XBBCmortoMPf8e6f_gAdp_RWNERwyqjYRwdjLgQZy8khepu2KfRDBmyC79zrEHV2wePQ4WWwYTlf9X3I4TN4wNpb7HLCzs9d63KIK6xNdh8ul-ZVO58yng8L7fEyhpT12lR7AxEb6Pt0hPY63Sc4_q4j9HJ783x9X80e7x6up7PKMMFz1TJdtx1pwTSkk7UBMW4aqTXUk3oiLLWNGFtOatloIbWVdfkKhORStLaTrWQjdLb1LSneB0hZLVxaJ9AewpAUFZxRVgwmRcq3UlMCpwidWka30HGlKFFr0mpDWq0xKsrVhrRiZe_0-8TQLsD-bv1wLYKrrQDKox8OokrGQWFhXQSTlQ3unxNfkFOP1g</recordid><startdate>201501</startdate><enddate>201501</enddate><creator>LI, Juan</creator><creator>FENG, Juan</creator><creator>LUO, Cheng</creator><creator>Herman, Ho-Yung Sung</creator><creator>JIANG, Ren-Wang</creator><general>Elsevier B.V</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>201501</creationdate><title>Absolute configuration of podophyllotoxone and its inhibitory activity against human prostate cancer cells</title><author>LI, Juan ; FENG, Juan ; LUO, Cheng ; Herman, Ho-Yung Sung ; JIANG, Ren-Wang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c365t-b3a4bf0bec70f84ce62778aae49496d1d762d50487a68ad84651e68586bdf8b83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Absolute configuration</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Berberidaceae - chemistry</topic><topic>Cell Line, Tumor</topic><topic>Dose-Response Relationship, Drug</topic><topic>G2 Phase - drug effects</topic><topic>Humans</topic><topic>Hydrogen Bonding - drug effects</topic><topic>Male</topic><topic>Molecular Conformation</topic><topic>Molecular docking</topic><topic>Molecular Docking Simulation</topic><topic>Phytotherapy</topic><topic>Plant Extracts - chemistry</topic><topic>Plant Extracts - pharmacology</topic><topic>Plant Roots - chemistry</topic><topic>Podophyllotoxin - chemistry</topic><topic>Podophyllotoxin - pharmacology</topic><topic>Podophyllotoxone</topic><topic>Polymerization</topic><topic>Prostate cancer</topic><topic>Prostatic Neoplasms - drug therapy</topic><topic>Tubulin</topic><topic>Tubulin - drug effects</topic><topic>Tubulin Modulators - pharmacology</topic><toplevel>online_resources</toplevel><creatorcontrib>LI, Juan</creatorcontrib><creatorcontrib>FENG, Juan</creatorcontrib><creatorcontrib>LUO, Cheng</creatorcontrib><creatorcontrib>Herman, Ho-Yung Sung</creatorcontrib><creatorcontrib>JIANG, Ren-Wang</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>Chinese journal of natural medicines</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>LI, Juan</au><au>FENG, Juan</au><au>LUO, Cheng</au><au>Herman, Ho-Yung Sung</au><au>JIANG, Ren-Wang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Absolute configuration of podophyllotoxone and its inhibitory activity against human prostate cancer cells</atitle><jtitle>Chinese journal of natural medicines</jtitle><addtitle>Chin J Nat Med</addtitle><date>2015-01</date><risdate>2015</risdate><volume>13</volume><issue>1</issue><spage>59</spage><epage>64</epage><pages>59-64</pages><issn>1875-5364</issn><eissn>1875-5364</eissn><abstract>Podophyllotoxone (1) was isolated from the roots of Dysosma versipellis. The structure was determined by spectroscopic analysis in combination with single-crystal X-ray analysis. The absolute configuration of compound 1 was assigned based on the Flack parameter. It showed significant inhibitory activities against human prostate cancer cells PC3 and DU145 with IC50 values being 14.7 and 20.6 μmol·L−1, respectively. It also arrested the cells at G2/M phase. Tubulin polymerization assay showed that it inhibited the tubulin polymerization in a dose-dependent manner, and molecular docking analysis revealed a different binding mode with tubulin as compared with those known tubulin inhibitors.</abstract><cop>China</cop><pub>Elsevier B.V</pub><pmid>25660289</pmid><doi>10.1016/S1875-5364(15)60007-3</doi><tpages>6</tpages></addata></record> |
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| subjects | Absolute configuration Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Berberidaceae - chemistry Cell Line, Tumor Dose-Response Relationship, Drug G2 Phase - drug effects Humans Hydrogen Bonding - drug effects Male Molecular Conformation Molecular docking Molecular Docking Simulation Phytotherapy Plant Extracts - chemistry Plant Extracts - pharmacology Plant Roots - chemistry Podophyllotoxin - chemistry Podophyllotoxin - pharmacology Podophyllotoxone Polymerization Prostate cancer Prostatic Neoplasms - drug therapy Tubulin Tubulin - drug effects Tubulin Modulators - pharmacology |
| title | Absolute configuration of podophyllotoxone and its inhibitory activity against human prostate cancer cells |
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