Pycnanthuquinone C, an Unusual 6,6,5-Tricyclic Geranyltoluquinone from the Western Australian Brown Alga Cystophora harveyi
Chemical investigation of the Western Australian marine brown alga Cystophora harveyi resulted in the isolation of the new linearly fused 6,6,5-tricyclic compound pycnanthuquinone C (1), in addition to four previously reported geranyltoluquinol derivatives. Structures were elucidated by interpretati...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2007-04, Vol.70 (4), p.671-674 |
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| creator | Laird, Damian W Poole, Rachael Wikström, Maria van Altena, Ian A |
| description | Chemical investigation of the Western Australian marine brown alga Cystophora harveyi resulted in the isolation of the new linearly fused 6,6,5-tricyclic compound pycnanthuquinone C (1), in addition to four previously reported geranyltoluquinol derivatives. Structures were elucidated by interpretation of spectrometric data. Compounds with the same cyclic skeleton as 1 have been reported to be useful drug leads for the treatment of type 2 diabetes, while compounds 4 and 7 are known constituents of Chinese medicinal herbs. A biosynthetic scheme encompassing all of the geranyltoluquinol derivatives isolated from C. harveyi is proposed. |
| doi_str_mv | 10.1021/np060566m |
| format | Article |
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Structures were elucidated by interpretation of spectrometric data. Compounds with the same cyclic skeleton as 1 have been reported to be useful drug leads for the treatment of type 2 diabetes, while compounds 4 and 7 are known constituents of Chinese medicinal herbs. A biosynthetic scheme encompassing all of the geranyltoluquinol derivatives isolated from C. harveyi is proposed.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np060566m</identifier><identifier>PMID: 17346075</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>1,4-Dimethoxy-(3',7'-dimethylocta-2',6'-dienyl)-6-methylbenzene ; 2-(3',7'-Dimethylocta-2',6'-dienyl)-4-hydroxy-1-methoxy-6-methylbenzene ; 2-(3',7'-Dimethylocta-2',6'-dienyl)-6-methyl-2,5-cyclohexadiene-1,4-dione ; algae and seaweeds ; atractylochromene ; Biological and medical sciences ; chemical structure ; Cystophora ; Cystophora harveyi ; Diabetes Mellitus, Type 2 - drug therapy ; Drugs, Chinese Herbal - chemistry ; Fatty Acids, Unsaturated - biosynthesis ; Fatty Acids, Unsaturated - chemistry ; Fatty Acids, Unsaturated - isolation & purification ; Fatty Acids, Unsaturated - pharmacology ; General pharmacology ; geranyltoluquinone ; Marine Biology ; Medical sciences ; Molecular Structure ; Naphthoquinones - chemistry ; Naphthoquinones - isolation & purification ; Naphthoquinones - pharmacology ; Phaeophyceae - chemistry ; Pharmacognosy. 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Drug treatments ; pycnanthuquinone ; quinones ; Sargassaceae ; spectral analysis ; Terpenes ; Western Australia</subject><ispartof>Journal of natural products (Washington, D.C.), 2007-04, Vol.70 (4), p.671-674</ispartof><rights>Copyright © 2007 American Chemical Society and American Society of Pharmacognosy</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a436t-978a37c70432ec3b4738d9f9a8ea7da970a17561eb3285eebe3fcf12f3b59b8f3</citedby><cites>FETCH-LOGICAL-a436t-978a37c70432ec3b4738d9f9a8ea7da970a17561eb3285eebe3fcf12f3b59b8f3</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/np060566m$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np060566m$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2756,27067,27915,27916,56729,56779</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18715219$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17346075$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Laird, Damian W</creatorcontrib><creatorcontrib>Poole, Rachael</creatorcontrib><creatorcontrib>Wikström, Maria</creatorcontrib><creatorcontrib>van Altena, Ian A</creatorcontrib><title>Pycnanthuquinone C, an Unusual 6,6,5-Tricyclic Geranyltoluquinone from the Western Australian Brown Alga Cystophora harveyi</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Chemical investigation of the Western Australian marine brown alga Cystophora harveyi resulted in the isolation of the new linearly fused 6,6,5-tricyclic compound pycnanthuquinone C (1), in addition to four previously reported geranyltoluquinol derivatives. Structures were elucidated by interpretation of spectrometric data. Compounds with the same cyclic skeleton as 1 have been reported to be useful drug leads for the treatment of type 2 diabetes, while compounds 4 and 7 are known constituents of Chinese medicinal herbs. A biosynthetic scheme encompassing all of the geranyltoluquinol derivatives isolated from C. harveyi is proposed.</description><subject>1,4-Dimethoxy-(3',7'-dimethylocta-2',6'-dienyl)-6-methylbenzene</subject><subject>2-(3',7'-Dimethylocta-2',6'-dienyl)-4-hydroxy-1-methoxy-6-methylbenzene</subject><subject>2-(3',7'-Dimethylocta-2',6'-dienyl)-6-methyl-2,5-cyclohexadiene-1,4-dione</subject><subject>algae and seaweeds</subject><subject>atractylochromene</subject><subject>Biological and medical sciences</subject><subject>chemical structure</subject><subject>Cystophora</subject><subject>Cystophora harveyi</subject><subject>Diabetes Mellitus, Type 2 - drug therapy</subject><subject>Drugs, Chinese Herbal - chemistry</subject><subject>Fatty Acids, Unsaturated - biosynthesis</subject><subject>Fatty Acids, Unsaturated - chemistry</subject><subject>Fatty Acids, Unsaturated - isolation & purification</subject><subject>Fatty Acids, Unsaturated - pharmacology</subject><subject>General pharmacology</subject><subject>geranyltoluquinone</subject><subject>Marine Biology</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Naphthoquinones - chemistry</subject><subject>Naphthoquinones - isolation & purification</subject><subject>Naphthoquinones - pharmacology</subject><subject>Phaeophyceae - chemistry</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>pycnanthuquinone</subject><subject>quinones</subject><subject>Sargassaceae</subject><subject>spectral analysis</subject><subject>Terpenes</subject><subject>Western Australia</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkUGLEzEUx4Mobl09-AU0FwWho8lkkswc1-KuQsGFbSnsJbxJk-2sadJNZtTBL2-WlvYieEkg75df8t4fodeUfKSkpJ_8jgjChdg-QRPKS1IIUvKnaEKoYAWrRXWGXqR0TwhhpOHP0RmVrBJE8gn6cz1qD77fDA9D54M3eDbF4PHSD2kAh8VUTHmxiJ0etes0vjIR_Oj64I4XbAxb3G8MXpnUm-jxxZD6CK7Lms8x_MoH7g7wbEx92G1CBLyB-NOM3Uv0zIJL5tVhP0fLyy-L2ddi_v3q2-xiXkDFRF80sgYmtSQVK41mbSVZvW5sA7UBuYZGEqCSC2paVtbcmNYwqy0tLWt509aWnaP3e-8uhochf1Jtu6SNc-BNGJJ6NGe3-C9YkrKRlPIMftiDOoaUorFqF7stxFFRoh4jUcdIMvvmIB3arVmfyEMGGXh3ACBpcDYPWHfpxNUyZ0qbzBV7rstj_n2sQ_yhhGSSq8X1jbq95IzOV7dqlfm3e95CUHAXs3N5UxLKCJE1y-vpZdBJ3Ych-hzDP1r4C5txuP4</recordid><startdate>20070401</startdate><enddate>20070401</enddate><creator>Laird, Damian W</creator><creator>Poole, Rachael</creator><creator>Wikström, Maria</creator><creator>van Altena, Ian A</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><scope>FBQ</scope><scope>BSCLL</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>8FD</scope><scope>F1W</scope><scope>FR3</scope><scope>H99</scope><scope>L.F</scope><scope>L.G</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20070401</creationdate><title>Pycnanthuquinone C, an Unusual 6,6,5-Tricyclic Geranyltoluquinone from the Western Australian Brown Alga Cystophora harveyi</title><author>Laird, Damian W ; Poole, Rachael ; Wikström, Maria ; van Altena, Ian A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a436t-978a37c70432ec3b4738d9f9a8ea7da970a17561eb3285eebe3fcf12f3b59b8f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>1,4-Dimethoxy-(3',7'-dimethylocta-2',6'-dienyl)-6-methylbenzene</topic><topic>2-(3',7'-Dimethylocta-2',6'-dienyl)-4-hydroxy-1-methoxy-6-methylbenzene</topic><topic>2-(3',7'-Dimethylocta-2',6'-dienyl)-6-methyl-2,5-cyclohexadiene-1,4-dione</topic><topic>algae and seaweeds</topic><topic>atractylochromene</topic><topic>Biological and medical sciences</topic><topic>chemical structure</topic><topic>Cystophora</topic><topic>Cystophora harveyi</topic><topic>Diabetes Mellitus, Type 2 - drug therapy</topic><topic>Drugs, Chinese Herbal - chemistry</topic><topic>Fatty Acids, Unsaturated - biosynthesis</topic><topic>Fatty Acids, Unsaturated - chemistry</topic><topic>Fatty Acids, Unsaturated - isolation & purification</topic><topic>Fatty Acids, Unsaturated - pharmacology</topic><topic>General pharmacology</topic><topic>geranyltoluquinone</topic><topic>Marine Biology</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Naphthoquinones - chemistry</topic><topic>Naphthoquinones - isolation & purification</topic><topic>Naphthoquinones - pharmacology</topic><topic>Phaeophyceae - chemistry</topic><topic>Pharmacognosy. 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Nat. Prod</addtitle><date>2007-04-01</date><risdate>2007</risdate><volume>70</volume><issue>4</issue><spage>671</spage><epage>674</epage><pages>671-674</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Chemical investigation of the Western Australian marine brown alga Cystophora harveyi resulted in the isolation of the new linearly fused 6,6,5-tricyclic compound pycnanthuquinone C (1), in addition to four previously reported geranyltoluquinol derivatives. Structures were elucidated by interpretation of spectrometric data. Compounds with the same cyclic skeleton as 1 have been reported to be useful drug leads for the treatment of type 2 diabetes, while compounds 4 and 7 are known constituents of Chinese medicinal herbs. A biosynthetic scheme encompassing all of the geranyltoluquinol derivatives isolated from C. harveyi is proposed.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>17346075</pmid><doi>10.1021/np060566m</doi><tpages>4</tpages></addata></record> |
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| ispartof | Journal of natural products (Washington, D.C.), 2007-04, Vol.70 (4), p.671-674 |
| issn | 0163-3864 1520-6025 |
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| source | MEDLINE; ACS Publications |
| subjects | 1,4-Dimethoxy-(3',7'-dimethylocta-2',6'-dienyl)-6-methylbenzene 2-(3',7'-Dimethylocta-2',6'-dienyl)-4-hydroxy-1-methoxy-6-methylbenzene 2-(3',7'-Dimethylocta-2',6'-dienyl)-6-methyl-2,5-cyclohexadiene-1,4-dione algae and seaweeds atractylochromene Biological and medical sciences chemical structure Cystophora Cystophora harveyi Diabetes Mellitus, Type 2 - drug therapy Drugs, Chinese Herbal - chemistry Fatty Acids, Unsaturated - biosynthesis Fatty Acids, Unsaturated - chemistry Fatty Acids, Unsaturated - isolation & purification Fatty Acids, Unsaturated - pharmacology General pharmacology geranyltoluquinone Marine Biology Medical sciences Molecular Structure Naphthoquinones - chemistry Naphthoquinones - isolation & purification Naphthoquinones - pharmacology Phaeophyceae - chemistry Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments pycnanthuquinone quinones Sargassaceae spectral analysis Terpenes Western Australia |
| title | Pycnanthuquinone C, an Unusual 6,6,5-Tricyclic Geranyltoluquinone from the Western Australian Brown Alga Cystophora harveyi |
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