Anti-hepatitis C Virus Natural Product from a Fungus, Penicillium herquei
New diazabicyclo[2.2.2]octane derivatives, peniciherquamides A–C (1–3), and a novel herqueinone derivative, neoherqueinone (5), were isolated from a fungal culture broth of Penicillium herquei. The structures of these novel compounds were determined by interpretation of spectroscopic data (1D/2D NM...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2016-02, Vol.79 (2), p.442-446 |
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| creator | Nishikori, Shu Takemoto, Kenji Kamisuki, Shinji Nakajima, Syo Kuramochi, Kouji Tsukuda, Senko Iwamoto, Masashi Katayama, Yuri Suzuki, Takahiro Kobayashi, Susumu Watashi, Koichi Sugawara, Fumio |
| description | New diazabicyclo[2.2.2]octane derivatives, peniciherquamides A–C (1–3), and a novel herqueinone derivative, neoherqueinone (5), were isolated from a fungal culture broth of Penicillium herquei. The structures of these novel compounds were determined by interpretation of spectroscopic data (1D/2D NMR, MS, and IR). Four known compounds, preparaherquamide (4), peniciherqueinone (6), and herqueinone/isoherqueinone (7/7a), were also obtained. The isolated compounds were tested for anti-hepatitis C virus (HCV) activity, and peniciherquamide C (3) was found to display an IC50 value of 5.1 μM. To our knowledge, this is the first report of a diazabicyclo[2.2.2]octane derivative with anti-HCV activity. |
| doi_str_mv | 10.1021/acs.jnatprod.5b00555 |
| format | Article |
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The structures of these novel compounds were determined by interpretation of spectroscopic data (1D/2D NMR, MS, and IR). Four known compounds, preparaherquamide (4), peniciherqueinone (6), and herqueinone/isoherqueinone (7/7a), were also obtained. The isolated compounds were tested for anti-hepatitis C virus (HCV) activity, and peniciherquamide C (3) was found to display an IC50 value of 5.1 μM. 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Nat. Prod</addtitle><description>New diazabicyclo[2.2.2]octane derivatives, peniciherquamides A–C (1–3), and a novel herqueinone derivative, neoherqueinone (5), were isolated from a fungal culture broth of Penicillium herquei. The structures of these novel compounds were determined by interpretation of spectroscopic data (1D/2D NMR, MS, and IR). Four known compounds, preparaherquamide (4), peniciherqueinone (6), and herqueinone/isoherqueinone (7/7a), were also obtained. The isolated compounds were tested for anti-hepatitis C virus (HCV) activity, and peniciherquamide C (3) was found to display an IC50 value of 5.1 μM. To our knowledge, this is the first report of a diazabicyclo[2.2.2]octane derivative with anti-HCV activity.</description><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - isolation & purification</subject><subject>Antiviral Agents - pharmacology</subject><subject>Aza Compounds - chemistry</subject><subject>Aza Compounds - isolation & purification</subject><subject>Aza Compounds - pharmacology</subject><subject>Biological Products - chemistry</subject><subject>Biological Products - isolation & purification</subject><subject>Biological Products - pharmacology</subject><subject>Cyclooctanes - chemistry</subject><subject>Cyclooctanes - isolation & purification</subject><subject>Cyclooctanes - pharmacology</subject><subject>Hepacivirus - drug effects</subject><subject>Molecular Structure</subject><subject>Penicillium - chemistry</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kDtPwzAUhS0EoqXwDxDyyEDKtWM7zlhVFCpV0AFYI8dxqKs8ih8D_55AW0amu3znHN0PoWsCUwKU3Cvtp9tOhZ3rqykvATjnJ2hMOIVEAOWnaAxEpEkqBRuhC--3AJBCzs_RiArJJAc2RstZF2yyMTsVbLAez_G7ddHjZxWiUw1eD-1RB1y7vsUKL2L3Ef0dXpvOats0NrZ4Y9xnNPYSndWq8ebqcCfobfHwOn9KVi-Py_lslShGWEhKWlekzEslMs1zpmrIAFhW01wKlUlFS8VlKlLQwE1upGY55VqTLGUyI2WVTtDtvnd4fNj1oWit16ZpVGf66AuSCckFo0QOKNuj2vXeO1MXO2db5b4KAsWPxGKQWBwlFgeJQ-zmsBDL1lR_oaO1AYA98Bvvo-uGh__v_AbMaICc</recordid><startdate>20160226</startdate><enddate>20160226</enddate><creator>Nishikori, Shu</creator><creator>Takemoto, Kenji</creator><creator>Kamisuki, Shinji</creator><creator>Nakajima, Syo</creator><creator>Kuramochi, Kouji</creator><creator>Tsukuda, Senko</creator><creator>Iwamoto, Masashi</creator><creator>Katayama, Yuri</creator><creator>Suzuki, Takahiro</creator><creator>Kobayashi, Susumu</creator><creator>Watashi, Koichi</creator><creator>Sugawara, Fumio</creator><general>American Chemical Society and American Society of Pharmacognosy</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>20160226</creationdate><title>Anti-hepatitis C Virus Natural Product from a Fungus, Penicillium herquei</title><author>Nishikori, Shu ; Takemoto, Kenji ; Kamisuki, Shinji ; Nakajima, Syo ; Kuramochi, Kouji ; Tsukuda, Senko ; Iwamoto, Masashi ; Katayama, Yuri ; Suzuki, Takahiro ; Kobayashi, Susumu ; Watashi, Koichi ; Sugawara, Fumio</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a414t-b2fd1b9ba67c594af070047f2986a78a2ba583630c05e9e8c4925cc1734871bd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Antiviral Agents - chemistry</topic><topic>Antiviral Agents - isolation & purification</topic><topic>Antiviral Agents - pharmacology</topic><topic>Aza Compounds - chemistry</topic><topic>Aza Compounds - isolation & purification</topic><topic>Aza Compounds - pharmacology</topic><topic>Biological Products - chemistry</topic><topic>Biological Products - isolation & purification</topic><topic>Biological Products - pharmacology</topic><topic>Cyclooctanes - chemistry</topic><topic>Cyclooctanes - isolation & purification</topic><topic>Cyclooctanes - pharmacology</topic><topic>Hepacivirus - drug effects</topic><topic>Molecular Structure</topic><topic>Penicillium - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nishikori, Shu</creatorcontrib><creatorcontrib>Takemoto, Kenji</creatorcontrib><creatorcontrib>Kamisuki, Shinji</creatorcontrib><creatorcontrib>Nakajima, Syo</creatorcontrib><creatorcontrib>Kuramochi, Kouji</creatorcontrib><creatorcontrib>Tsukuda, Senko</creatorcontrib><creatorcontrib>Iwamoto, Masashi</creatorcontrib><creatorcontrib>Katayama, Yuri</creatorcontrib><creatorcontrib>Suzuki, Takahiro</creatorcontrib><creatorcontrib>Kobayashi, Susumu</creatorcontrib><creatorcontrib>Watashi, Koichi</creatorcontrib><creatorcontrib>Sugawara, Fumio</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>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nishikori, Shu</au><au>Takemoto, Kenji</au><au>Kamisuki, Shinji</au><au>Nakajima, Syo</au><au>Kuramochi, Kouji</au><au>Tsukuda, Senko</au><au>Iwamoto, Masashi</au><au>Katayama, Yuri</au><au>Suzuki, Takahiro</au><au>Kobayashi, Susumu</au><au>Watashi, Koichi</au><au>Sugawara, Fumio</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Anti-hepatitis C Virus Natural Product from a Fungus, Penicillium herquei</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2016-02-26</date><risdate>2016</risdate><volume>79</volume><issue>2</issue><spage>442</spage><epage>446</epage><pages>442-446</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>New diazabicyclo[2.2.2]octane derivatives, peniciherquamides A–C (1–3), and a novel herqueinone derivative, neoherqueinone (5), were isolated from a fungal culture broth of Penicillium herquei. The structures of these novel compounds were determined by interpretation of spectroscopic data (1D/2D NMR, MS, and IR). Four known compounds, preparaherquamide (4), peniciherqueinone (6), and herqueinone/isoherqueinone (7/7a), were also obtained. The isolated compounds were tested for anti-hepatitis C virus (HCV) activity, and peniciherquamide C (3) was found to display an IC50 value of 5.1 μM. 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| subjects | Antiviral Agents - chemistry Antiviral Agents - isolation & purification Antiviral Agents - pharmacology Aza Compounds - chemistry Aza Compounds - isolation & purification Aza Compounds - pharmacology Biological Products - chemistry Biological Products - isolation & purification Biological Products - pharmacology Cyclooctanes - chemistry Cyclooctanes - isolation & purification Cyclooctanes - pharmacology Hepacivirus - drug effects Molecular Structure Penicillium - chemistry |
| title | Anti-hepatitis C Virus Natural Product from a Fungus, Penicillium herquei |
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