Prenylcoumarin with Rev-export inhibitory activity from Cnidii Monnieris Fructus
Prenylcoumarin osthol (1) was disclosed as the new Rev-export inhibitor from Cnidii Monnieris Fructus. Both prenyl residue and carbonyl conjugated double bond were revealed to play an important role in the biological potency of 1. By use of the fission yeast expressing the model fusion protein compr...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2010-06, Vol.20 (12), p.3717-3720 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Tamura, Satoru Fujitani, Toshiaki Kaneko, Masafumi Murakami, Nobutoshi |
| description | Prenylcoumarin osthol (1) was disclosed as the new Rev-export inhibitor from Cnidii Monnieris Fructus. Both prenyl residue and carbonyl conjugated double bond were revealed to play an important role in the biological potency of 1.
By use of the fission yeast expressing the model fusion protein comprised of GST, SV40 T antigen NLS, GFP, and Rev-NES in the bioassay, the prenylcoumarin osthol (1) was disclosed as the new Rev-export inhibitor from the MeOH extract of Cnidii Monnieris Fructus. Furthermore, 1 was also found to inhibit export the genuine Rev in HeLa cells by indirect fluorescent antibody technique. By the competitive experiment using the biotinylated probe 3, osthol (1) was revealed to inhibit nuclear export of Rev through a NES non-antagonistic mode. Structure–activity relationship analysis of several analogs of 1 clarified that both prenyl side chain and double bond adjacent to the lactone carbonyl residue play an important role in the Rev-export inhibitory potency of 1. |
| doi_str_mv | 10.1016/j.bmcl.2010.04.081 |
| format | Article |
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By use of the fission yeast expressing the model fusion protein comprised of GST, SV40 T antigen NLS, GFP, and Rev-NES in the bioassay, the prenylcoumarin osthol (1) was disclosed as the new Rev-export inhibitor from the MeOH extract of Cnidii Monnieris Fructus. Furthermore, 1 was also found to inhibit export the genuine Rev in HeLa cells by indirect fluorescent antibody technique. By the competitive experiment using the biotinylated probe 3, osthol (1) was revealed to inhibit nuclear export of Rev through a NES non-antagonistic mode. Structure–activity relationship analysis of several analogs of 1 clarified that both prenyl side chain and double bond adjacent to the lactone carbonyl residue play an important role in the Rev-export inhibitory potency of 1.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2010.04.081</identifier><identifier>PMID: 20493693</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Active Transport, Cell Nucleus - drug effects ; Adjuvants, Immunologic ; Anti-HIV ; Anti-HIV Agents - chemistry ; Anti-HIV Agents - isolation & purification ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antiviral agents ; Biological and medical sciences ; Cnidium monnieri Cusson ; Coumarins - isolation & purification ; Coumarins - pharmacology ; General pharmacology ; HeLa Cells ; HIV-1 ; Humans ; Medical sciences ; Osthol ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Plant Extracts - chemistry ; Plant Extracts - therapeutic use ; Plants, Medicinal - chemistry ; Prenylcoumarin ; rev Gene Products, Human Immunodeficiency Virus - antagonists & inhibitors ; rev Gene Products, Human Immunodeficiency Virus - metabolism ; Rev-export inhibitor ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2010-06, Vol.20 (12), p.3717-3720</ispartof><rights>2010 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright 2010 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c385t-ec97f08725e01e1fc1b8f7032ccf4380286347e488d36f701de835df10819173</citedby><cites>FETCH-LOGICAL-c385t-ec97f08725e01e1fc1b8f7032ccf4380286347e488d36f701de835df10819173</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.2010.04.081$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22902466$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20493693$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tamura, Satoru</creatorcontrib><creatorcontrib>Fujitani, Toshiaki</creatorcontrib><creatorcontrib>Kaneko, Masafumi</creatorcontrib><creatorcontrib>Murakami, Nobutoshi</creatorcontrib><title>Prenylcoumarin with Rev-export inhibitory activity from Cnidii Monnieris Fructus</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Prenylcoumarin osthol (1) was disclosed as the new Rev-export inhibitor from Cnidii Monnieris Fructus. Both prenyl residue and carbonyl conjugated double bond were revealed to play an important role in the biological potency of 1.
By use of the fission yeast expressing the model fusion protein comprised of GST, SV40 T antigen NLS, GFP, and Rev-NES in the bioassay, the prenylcoumarin osthol (1) was disclosed as the new Rev-export inhibitor from the MeOH extract of Cnidii Monnieris Fructus. Furthermore, 1 was also found to inhibit export the genuine Rev in HeLa cells by indirect fluorescent antibody technique. By the competitive experiment using the biotinylated probe 3, osthol (1) was revealed to inhibit nuclear export of Rev through a NES non-antagonistic mode. Structure–activity relationship analysis of several analogs of 1 clarified that both prenyl side chain and double bond adjacent to the lactone carbonyl residue play an important role in the Rev-export inhibitory potency of 1.</description><subject>Active Transport, Cell Nucleus - drug effects</subject><subject>Adjuvants, Immunologic</subject><subject>Anti-HIV</subject><subject>Anti-HIV Agents - chemistry</subject><subject>Anti-HIV Agents - isolation & purification</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antiviral agents</subject><subject>Biological and medical sciences</subject><subject>Cnidium monnieri Cusson</subject><subject>Coumarins - isolation & purification</subject><subject>Coumarins - pharmacology</subject><subject>General pharmacology</subject><subject>HeLa Cells</subject><subject>HIV-1</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Osthol</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Plant Extracts - chemistry</subject><subject>Plant Extracts - therapeutic use</subject><subject>Plants, Medicinal - chemistry</subject><subject>Prenylcoumarin</subject><subject>rev Gene Products, Human Immunodeficiency Virus - antagonists & inhibitors</subject><subject>rev Gene Products, Human Immunodeficiency Virus - metabolism</subject><subject>Rev-export inhibitor</subject><subject>Structure-Activity Relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kEtvEzEQgC1ERUPhD3BAe0GcNh0_4vVKXFBEAamICvXAzdp4x-pEu-tge1Py73GUUG6cRpr55vUx9obDkgPX19vlZnTDUkBJgFqC4c_Ygiutaqlg9ZwtoNVQm1b9vGQvU9oCcAVKvWCXAlQrdSsX7O4u4nQYXJjHLtJUPVJ-qH7gvsbfuxBzRdMDbSiHeKg6l2lP-VD5GMZqPVFPVH0L00QYKVU3cXZ5Tq_Yhe-GhK_P8Yrd33y6X3-pb79__rr-eFs7aVa5Rtc2HkwjVggcuXd8Y3wDUjjnlTQgjJaqQWVML3Up8B6NXPWely9b3sgr9v40dhfDrxlTtiMlh8PQTRjmZBspudFCQCHFiXQxpBTR212k8uzBcrBHj3Zrjx7t0aMFZcuG0vT2PH7ejNg_tfwVV4B3Z6BLrht87CZH6R8nWhBK68J9OHFYXOyLKZsc4eSwp4gu2z7Q_-74A9-nkPY</recordid><startdate>20100615</startdate><enddate>20100615</enddate><creator>Tamura, Satoru</creator><creator>Fujitani, Toshiaki</creator><creator>Kaneko, Masafumi</creator><creator>Murakami, Nobutoshi</creator><general>Elsevier Ltd</general><general>Elsevier</general><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>20100615</creationdate><title>Prenylcoumarin with Rev-export inhibitory activity from Cnidii Monnieris Fructus</title><author>Tamura, Satoru ; Fujitani, Toshiaki ; Kaneko, Masafumi ; Murakami, Nobutoshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c385t-ec97f08725e01e1fc1b8f7032ccf4380286347e488d36f701de835df10819173</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Active Transport, Cell Nucleus - drug effects</topic><topic>Adjuvants, Immunologic</topic><topic>Anti-HIV</topic><topic>Anti-HIV Agents - chemistry</topic><topic>Anti-HIV Agents - isolation & purification</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antiviral agents</topic><topic>Biological and medical sciences</topic><topic>Cnidium monnieri Cusson</topic><topic>Coumarins - isolation & purification</topic><topic>Coumarins - pharmacology</topic><topic>General pharmacology</topic><topic>HeLa Cells</topic><topic>HIV-1</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Osthol</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Plant Extracts - chemistry</topic><topic>Plant Extracts - therapeutic use</topic><topic>Plants, Medicinal - chemistry</topic><topic>Prenylcoumarin</topic><topic>rev Gene Products, Human Immunodeficiency Virus - antagonists & inhibitors</topic><topic>rev Gene Products, Human Immunodeficiency Virus - metabolism</topic><topic>Rev-export inhibitor</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tamura, Satoru</creatorcontrib><creatorcontrib>Fujitani, Toshiaki</creatorcontrib><creatorcontrib>Kaneko, Masafumi</creatorcontrib><creatorcontrib>Murakami, Nobutoshi</creatorcontrib><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>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tamura, Satoru</au><au>Fujitani, Toshiaki</au><au>Kaneko, Masafumi</au><au>Murakami, Nobutoshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Prenylcoumarin with Rev-export inhibitory activity from Cnidii Monnieris Fructus</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2010-06-15</date><risdate>2010</risdate><volume>20</volume><issue>12</issue><spage>3717</spage><epage>3720</epage><pages>3717-3720</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Prenylcoumarin osthol (1) was disclosed as the new Rev-export inhibitor from Cnidii Monnieris Fructus. Both prenyl residue and carbonyl conjugated double bond were revealed to play an important role in the biological potency of 1.
By use of the fission yeast expressing the model fusion protein comprised of GST, SV40 T antigen NLS, GFP, and Rev-NES in the bioassay, the prenylcoumarin osthol (1) was disclosed as the new Rev-export inhibitor from the MeOH extract of Cnidii Monnieris Fructus. Furthermore, 1 was also found to inhibit export the genuine Rev in HeLa cells by indirect fluorescent antibody technique. By the competitive experiment using the biotinylated probe 3, osthol (1) was revealed to inhibit nuclear export of Rev through a NES non-antagonistic mode. Structure–activity relationship analysis of several analogs of 1 clarified that both prenyl side chain and double bond adjacent to the lactone carbonyl residue play an important role in the Rev-export inhibitory potency of 1.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>20493693</pmid><doi>10.1016/j.bmcl.2010.04.081</doi><tpages>4</tpages></addata></record> |
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| subjects | Active Transport, Cell Nucleus - drug effects Adjuvants, Immunologic Anti-HIV Anti-HIV Agents - chemistry Anti-HIV Agents - isolation & purification Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral agents Biological and medical sciences Cnidium monnieri Cusson Coumarins - isolation & purification Coumarins - pharmacology General pharmacology HeLa Cells HIV-1 Humans Medical sciences Osthol Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plant Extracts - chemistry Plant Extracts - therapeutic use Plants, Medicinal - chemistry Prenylcoumarin rev Gene Products, Human Immunodeficiency Virus - antagonists & inhibitors rev Gene Products, Human Immunodeficiency Virus - metabolism Rev-export inhibitor Structure-Activity Relationship |
| title | Prenylcoumarin with Rev-export inhibitory activity from Cnidii Monnieris Fructus |
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