Peniciketals A–C, New Spiroketals from Saline Soil Derived Penicillium raistrichii
Peniciketals A–C (1–3), three new spiroketals with a benzo-fused 2,8-dioxabicyclo[3.3.1]nonane moiety, were isolated from the saline soil derived fungus Penicillium raistrichii. Their structures including absolute configurations were established by NMR, X-ray diffraction, and ECD calculations. Thei...
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| Veröffentlicht in: | Organic letters 2014-01, Vol.16 (1), p.90-93 |
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| container_title | Organic letters |
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| creator | Liu, Wei-Zhong Ma, Li-Ying Liu, De-Sheng Huang, Yu-Ling Wang, Chun-Hua Shi, Shou-Sen Pan, Xiao-Hong Song, Xiao-Dong Zhu, Rong-Xiu |
| description | Peniciketals A–C (1–3), three new spiroketals with a benzo-fused 2,8-dioxabicyclo[3.3.1]nonane moiety, were isolated from the saline soil derived fungus Penicillium raistrichii. Their structures including absolute configurations were established by NMR, X-ray diffraction, and ECD calculations. Their cytotoxicities were tested against A549, HL-60, and K562 cell lines, and 1–3 showed the selective effects on HL-60 cells with IC50 values of 3.2, 6.7, and 4.5 μM, respectively. |
| doi_str_mv | 10.1021/ol403076s |
| format | Article |
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Their structures including absolute configurations were established by NMR, X-ray diffraction, and ECD calculations. Their cytotoxicities were tested against A549, HL-60, and K562 cell lines, and 1–3 showed the selective effects on HL-60 cells with IC50 values of 3.2, 6.7, and 4.5 μM, respectively.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol403076s</identifier><identifier>PMID: 24283621</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Antineoplastic Agents - chemistry ; Antineoplastic Agents - isolation & purification ; Antineoplastic Agents - pharmacology ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor ; HL-60 Cells ; Humans ; K562 Cells ; Models, Molecular ; Molecular Conformation ; Penicillium - chemistry ; Pyrans - chemistry ; Pyrans - isolation & purification ; Pyrans - pharmacology ; Quantum Theory ; Salinity ; Soil - chemistry ; Spiro Compounds - chemistry ; Spiro Compounds - isolation & purification ; Spiro Compounds - pharmacology ; Stereoisomerism ; Structure-Activity Relationship</subject><ispartof>Organic letters, 2014-01, Vol.16 (1), p.90-93</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a315t-211b24fd4d44f6dc0d89cf8b4c37aee91dd51f5b0753ea000cea8469eed55e393</citedby><cites>FETCH-LOGICAL-a315t-211b24fd4d44f6dc0d89cf8b4c37aee91dd51f5b0753ea000cea8469eed55e393</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol403076s$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol403076s$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24283621$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Wei-Zhong</creatorcontrib><creatorcontrib>Ma, Li-Ying</creatorcontrib><creatorcontrib>Liu, De-Sheng</creatorcontrib><creatorcontrib>Huang, Yu-Ling</creatorcontrib><creatorcontrib>Wang, Chun-Hua</creatorcontrib><creatorcontrib>Shi, Shou-Sen</creatorcontrib><creatorcontrib>Pan, Xiao-Hong</creatorcontrib><creatorcontrib>Song, Xiao-Dong</creatorcontrib><creatorcontrib>Zhu, Rong-Xiu</creatorcontrib><title>Peniciketals A–C, New Spiroketals from Saline Soil Derived Penicillium raistrichii</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Peniciketals A–C (1–3), three new spiroketals with a benzo-fused 2,8-dioxabicyclo[3.3.1]nonane moiety, were isolated from the saline soil derived fungus Penicillium raistrichii. Their structures including absolute configurations were established by NMR, X-ray diffraction, and ECD calculations. Their cytotoxicities were tested against A549, HL-60, and K562 cell lines, and 1–3 showed the selective effects on HL-60 cells with IC50 values of 3.2, 6.7, and 4.5 μM, respectively.</description><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - isolation & purification</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Screening Assays, Antitumor</subject><subject>HL-60 Cells</subject><subject>Humans</subject><subject>K562 Cells</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>Penicillium - chemistry</subject><subject>Pyrans - chemistry</subject><subject>Pyrans - isolation & purification</subject><subject>Pyrans - pharmacology</subject><subject>Quantum Theory</subject><subject>Salinity</subject><subject>Soil - chemistry</subject><subject>Spiro Compounds - chemistry</subject><subject>Spiro Compounds - isolation & purification</subject><subject>Spiro Compounds - pharmacology</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkN9KwzAUh4Mobk4vfAHJjaBgNWmSdr0c8y8MFTavS5qcYmbazKRVvPMdfEOfxErnrrw6h8P3-8H5EDqk5JySmF44ywkjaRK20JCKmEUpEfH2Zk_IAO2FsCSEdpdsFw1iHo9ZEtMhWjxCbZR5gUbagCffn1_TM3wP73i-Mt6tz6V3FZ5La2rAc2csvgRv3kDjPmytaSvspQmNN-rZmH20U3Y5OFjPEXq6vlpMb6PZw83ddDKLJKOiiWJKi5iXmmvOy0QroseZKscFVyyVABnVWtBSFCQVDCQhRIEc8yQD0EIAy9gInfS9K-9eWwhNXpmgwFpZg2tDTnnWWWGcpB162qPKuxA8lPnKm0r6j5yS_FdivpHYsUfr2raoQG_IP2sdcNwDUoV86Vpfd1_-U_QDAG55og</recordid><startdate>20140103</startdate><enddate>20140103</enddate><creator>Liu, Wei-Zhong</creator><creator>Ma, Li-Ying</creator><creator>Liu, De-Sheng</creator><creator>Huang, Yu-Ling</creator><creator>Wang, Chun-Hua</creator><creator>Shi, Shou-Sen</creator><creator>Pan, Xiao-Hong</creator><creator>Song, Xiao-Dong</creator><creator>Zhu, Rong-Xiu</creator><general>American Chemical Society</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>20140103</creationdate><title>Peniciketals A–C, New Spiroketals from Saline Soil Derived Penicillium raistrichii</title><author>Liu, Wei-Zhong ; Ma, Li-Ying ; Liu, De-Sheng ; Huang, Yu-Ling ; Wang, Chun-Hua ; Shi, Shou-Sen ; Pan, Xiao-Hong ; Song, Xiao-Dong ; Zhu, Rong-Xiu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a315t-211b24fd4d44f6dc0d89cf8b4c37aee91dd51f5b0753ea000cea8469eed55e393</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - isolation & purification</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug Screening Assays, Antitumor</topic><topic>HL-60 Cells</topic><topic>Humans</topic><topic>K562 Cells</topic><topic>Models, Molecular</topic><topic>Molecular Conformation</topic><topic>Penicillium - chemistry</topic><topic>Pyrans - chemistry</topic><topic>Pyrans - isolation & purification</topic><topic>Pyrans - pharmacology</topic><topic>Quantum Theory</topic><topic>Salinity</topic><topic>Soil - chemistry</topic><topic>Spiro Compounds - chemistry</topic><topic>Spiro Compounds - isolation & purification</topic><topic>Spiro Compounds - pharmacology</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Wei-Zhong</creatorcontrib><creatorcontrib>Ma, Li-Ying</creatorcontrib><creatorcontrib>Liu, De-Sheng</creatorcontrib><creatorcontrib>Huang, Yu-Ling</creatorcontrib><creatorcontrib>Wang, Chun-Hua</creatorcontrib><creatorcontrib>Shi, Shou-Sen</creatorcontrib><creatorcontrib>Pan, Xiao-Hong</creatorcontrib><creatorcontrib>Song, Xiao-Dong</creatorcontrib><creatorcontrib>Zhu, Rong-Xiu</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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Wei-Zhong</au><au>Ma, Li-Ying</au><au>Liu, De-Sheng</au><au>Huang, Yu-Ling</au><au>Wang, Chun-Hua</au><au>Shi, Shou-Sen</au><au>Pan, Xiao-Hong</au><au>Song, Xiao-Dong</au><au>Zhu, Rong-Xiu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Peniciketals A–C, New Spiroketals from Saline Soil Derived Penicillium raistrichii</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2014-01-03</date><risdate>2014</risdate><volume>16</volume><issue>1</issue><spage>90</spage><epage>93</epage><pages>90-93</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Peniciketals A–C (1–3), three new spiroketals with a benzo-fused 2,8-dioxabicyclo[3.3.1]nonane moiety, were isolated from the saline soil derived fungus Penicillium raistrichii. Their structures including absolute configurations were established by NMR, X-ray diffraction, and ECD calculations. Their cytotoxicities were tested against A549, HL-60, and K562 cell lines, and 1–3 showed the selective effects on HL-60 cells with IC50 values of 3.2, 6.7, and 4.5 μM, respectively.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>24283621</pmid><doi>10.1021/ol403076s</doi><tpages>4</tpages></addata></record> |
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| ispartof | Organic letters, 2014-01, Vol.16 (1), p.90-93 |
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| subjects | Antineoplastic Agents - chemistry Antineoplastic Agents - isolation & purification Antineoplastic Agents - pharmacology Cell Line, Tumor Cell Proliferation - drug effects Dose-Response Relationship, Drug Drug Screening Assays, Antitumor HL-60 Cells Humans K562 Cells Models, Molecular Molecular Conformation Penicillium - chemistry Pyrans - chemistry Pyrans - isolation & purification Pyrans - pharmacology Quantum Theory Salinity Soil - chemistry Spiro Compounds - chemistry Spiro Compounds - isolation & purification Spiro Compounds - pharmacology Stereoisomerism Structure-Activity Relationship |
| title | Peniciketals A–C, New Spiroketals from Saline Soil Derived Penicillium raistrichii |
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