Lycopanerols I−L, Four New Tetraterpenoid Ethers from Botryococcus braunii
Four new tetraterpenoid ethers, lycopanerols I−L (5−8), were isolated from a culture of a strain of the green microalga Botryococcus braunii (L race). The structures were determined by means of spectral analyses and chemical degradation. The relative stereochemistry of these ethers was established b...
Gespeichert in:
| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2003-06, Vol.66 (6), p.772-778 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 778 |
|---|---|
| container_issue | 6 |
| container_start_page | 772 |
| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 66 |
| creator | Metzger, Pierre Rager, Marie-Noëlle Sellier, Nicole Largeau, Claude |
| description | Four new tetraterpenoid ethers, lycopanerols I−L (5−8), were isolated from a culture of a strain of the green microalga Botryococcus braunii (L race). The structures were determined by means of spectral analyses and chemical degradation. The relative stereochemistry of these ethers was established by ROESY NMR. A biogenetic relationship is proposed between lycopanerols and lycopadiene (1), the acyclic diunsaturated tetraterpene hydrocarbon synthesized by the alga. |
| doi_str_mv | 10.1021/np020604b |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_73431839</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>18871460</sourcerecordid><originalsourceid>FETCH-LOGICAL-a434t-496eaefc52a35a4042695c35aa03259f7e2081354322ed7c261e78d2537142fd3</originalsourceid><addsrcrecordid>eNqF0c1u1DAQB3CrArXbwqEvQHOhEhKB8fgjzhGqFqqm0KrbSy-W13FoSjYOdiLYN-DMI_IkGO1qe0HiZEv-zd-aGUIOKbyhgPRtPwCCBL7YITMqEHIJKJ6QGVDJcqYk3yP7MT4AAINS7JI9igoVlzAjVbWyfjC9C76L2fnvn7-q19mZn0L2yX3P5m4MZnRhcL1v6-x0vHchZk3wy-y9H8PKW2_tFLNFMFPfts_I08Z00T3fnAfk9ux0fvIxrz5_OD95V-WGMz7mvJTOuMYKNEwYDhxlKWy6GmAoyqZwCIoywRmiqwuLkrpC1ShYQTk2NTsgx-vcIfhvk4ujXrbRuq5Lffgp6oJxRhUr_wupUilSQoKv1tAGH2NwjR5CuzRhpSnovzPW2xkn-2ITOi2Wrn6Um6Em8HIDTLSma4LpbRsfHS-RK8Tk8rVr4-h-bN9N-KplwQqh51c3-uK6vLoT15daJn-09o3x2nwJKfP2BoEyoCBKkWq2Pxsb9UPaYp_W8I8W_gCJIqcF</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>18871460</pqid></control><display><type>article</type><title>Lycopanerols I−L, Four New Tetraterpenoid Ethers from Botryococcus braunii</title><source>ACS Publications</source><source>MEDLINE</source><creator>Metzger, Pierre ; Rager, Marie-Noëlle ; Sellier, Nicole ; Largeau, Claude</creator><creatorcontrib>Metzger, Pierre ; Rager, Marie-Noëlle ; Sellier, Nicole ; Largeau, Claude</creatorcontrib><description>Four new tetraterpenoid ethers, lycopanerols I−L (5−8), were isolated from a culture of a strain of the green microalga Botryococcus braunii (L race). The structures were determined by means of spectral analyses and chemical degradation. The relative stereochemistry of these ethers was established by ROESY NMR. A biogenetic relationship is proposed between lycopanerols and lycopadiene (1), the acyclic diunsaturated tetraterpene hydrocarbon synthesized by the alga.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np020604b</identifier><identifier>PMID: 12828460</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>acetic acids ; Analytical, structural and metabolic biochemistry ; benzene ; biochemical pathways ; Biological and medical sciences ; biosynthesis ; Botryococcus ; Botryococcus braunii ; carbon ; chemical structure ; Chlorophyta - chemistry ; Chlorophyta - metabolism ; Cote d'Ivoire ; epoxides ; ethers ; Ethers - chemistry ; Ethers - isolation & purification ; Fundamental and applied biological sciences. Psychology ; furans ; lycopadiene ; lycopane ; Lycopanerols ; methine ; microalgae ; Molecular Structure ; natural products ; Nuclear Magnetic Resonance, Biomolecular ; olefin ; Other biological molecules ; phytochemicals ; plant extracts ; protons ; spectral analysis ; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization ; stereochemistry ; Terpenes - chemistry ; Terpenes - isolation & purification ; Terpenes, steroids. Hormones ; terpenoids ; tetrahydrofuran ; tetratepenoid ethers ; Tetraterpenoid ethers</subject><ispartof>Journal of natural products (Washington, D.C.), 2003-06, Vol.66 (6), p.772-778</ispartof><rights>Copyright © 2003 American Chemical Society and American Society of Pharmacognosy</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a434t-496eaefc52a35a4042695c35aa03259f7e2081354322ed7c261e78d2537142fd3</citedby><cites>FETCH-LOGICAL-a434t-496eaefc52a35a4042695c35aa03259f7e2081354322ed7c261e78d2537142fd3</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/np020604b$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np020604b$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27055,27903,27904,56715,56765</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14924822$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12828460$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Metzger, Pierre</creatorcontrib><creatorcontrib>Rager, Marie-Noëlle</creatorcontrib><creatorcontrib>Sellier, Nicole</creatorcontrib><creatorcontrib>Largeau, Claude</creatorcontrib><title>Lycopanerols I−L, Four New Tetraterpenoid Ethers from Botryococcus braunii</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Four new tetraterpenoid ethers, lycopanerols I−L (5−8), were isolated from a culture of a strain of the green microalga Botryococcus braunii (L race). The structures were determined by means of spectral analyses and chemical degradation. The relative stereochemistry of these ethers was established by ROESY NMR. A biogenetic relationship is proposed between lycopanerols and lycopadiene (1), the acyclic diunsaturated tetraterpene hydrocarbon synthesized by the alga.</description><subject>acetic acids</subject><subject>Analytical, structural and metabolic biochemistry</subject><subject>benzene</subject><subject>biochemical pathways</subject><subject>Biological and medical sciences</subject><subject>biosynthesis</subject><subject>Botryococcus</subject><subject>Botryococcus braunii</subject><subject>carbon</subject><subject>chemical structure</subject><subject>Chlorophyta - chemistry</subject><subject>Chlorophyta - metabolism</subject><subject>Cote d'Ivoire</subject><subject>epoxides</subject><subject>ethers</subject><subject>Ethers - chemistry</subject><subject>Ethers - isolation & purification</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>furans</subject><subject>lycopadiene</subject><subject>lycopane</subject><subject>Lycopanerols</subject><subject>methine</subject><subject>microalgae</subject><subject>Molecular Structure</subject><subject>natural products</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>olefin</subject><subject>Other biological molecules</subject><subject>phytochemicals</subject><subject>plant extracts</subject><subject>protons</subject><subject>spectral analysis</subject><subject>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</subject><subject>stereochemistry</subject><subject>Terpenes - chemistry</subject><subject>Terpenes - isolation & purification</subject><subject>Terpenes, steroids. Hormones</subject><subject>terpenoids</subject><subject>tetrahydrofuran</subject><subject>tetratepenoid ethers</subject><subject>Tetraterpenoid ethers</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0c1u1DAQB3CrArXbwqEvQHOhEhKB8fgjzhGqFqqm0KrbSy-W13FoSjYOdiLYN-DMI_IkGO1qe0HiZEv-zd-aGUIOKbyhgPRtPwCCBL7YITMqEHIJKJ6QGVDJcqYk3yP7MT4AAINS7JI9igoVlzAjVbWyfjC9C76L2fnvn7-q19mZn0L2yX3P5m4MZnRhcL1v6-x0vHchZk3wy-y9H8PKW2_tFLNFMFPfts_I08Z00T3fnAfk9ux0fvIxrz5_OD95V-WGMz7mvJTOuMYKNEwYDhxlKWy6GmAoyqZwCIoywRmiqwuLkrpC1ShYQTk2NTsgx-vcIfhvk4ujXrbRuq5Lffgp6oJxRhUr_wupUilSQoKv1tAGH2NwjR5CuzRhpSnovzPW2xkn-2ITOi2Wrn6Um6Em8HIDTLSma4LpbRsfHS-RK8Tk8rVr4-h-bN9N-KplwQqh51c3-uK6vLoT15daJn-09o3x2nwJKfP2BoEyoCBKkWq2Pxsb9UPaYp_W8I8W_gCJIqcF</recordid><startdate>20030601</startdate><enddate>20030601</enddate><creator>Metzger, Pierre</creator><creator>Rager, Marie-Noëlle</creator><creator>Sellier, Nicole</creator><creator>Largeau, Claude</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>H95</scope><scope>H99</scope><scope>L.F</scope><scope>L.G</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20030601</creationdate><title>Lycopanerols I−L, Four New Tetraterpenoid Ethers from Botryococcus braunii</title><author>Metzger, Pierre ; Rager, Marie-Noëlle ; Sellier, Nicole ; Largeau, Claude</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a434t-496eaefc52a35a4042695c35aa03259f7e2081354322ed7c261e78d2537142fd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>acetic acids</topic><topic>Analytical, structural and metabolic biochemistry</topic><topic>benzene</topic><topic>biochemical pathways</topic><topic>Biological and medical sciences</topic><topic>biosynthesis</topic><topic>Botryococcus</topic><topic>Botryococcus braunii</topic><topic>carbon</topic><topic>chemical structure</topic><topic>Chlorophyta - chemistry</topic><topic>Chlorophyta - metabolism</topic><topic>Cote d'Ivoire</topic><topic>epoxides</topic><topic>ethers</topic><topic>Ethers - chemistry</topic><topic>Ethers - isolation & purification</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>furans</topic><topic>lycopadiene</topic><topic>lycopane</topic><topic>Lycopanerols</topic><topic>methine</topic><topic>microalgae</topic><topic>Molecular Structure</topic><topic>natural products</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>olefin</topic><topic>Other biological molecules</topic><topic>phytochemicals</topic><topic>plant extracts</topic><topic>protons</topic><topic>spectral analysis</topic><topic>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</topic><topic>stereochemistry</topic><topic>Terpenes - chemistry</topic><topic>Terpenes - isolation & purification</topic><topic>Terpenes, steroids. Hormones</topic><topic>terpenoids</topic><topic>tetrahydrofuran</topic><topic>tetratepenoid ethers</topic><topic>Tetraterpenoid ethers</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Metzger, Pierre</creatorcontrib><creatorcontrib>Rager, Marie-Noëlle</creatorcontrib><creatorcontrib>Sellier, Nicole</creatorcontrib><creatorcontrib>Largeau, Claude</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><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>Technology Research Database</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Engineering Research Database</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 1: Biological Sciences & Living Resources</collection><collection>ASFA: Marine Biotechnology Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Marine Biotechnology Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</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>Metzger, Pierre</au><au>Rager, Marie-Noëlle</au><au>Sellier, Nicole</au><au>Largeau, Claude</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Lycopanerols I−L, Four New Tetraterpenoid Ethers from Botryococcus braunii</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2003-06-01</date><risdate>2003</risdate><volume>66</volume><issue>6</issue><spage>772</spage><epage>778</epage><pages>772-778</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Four new tetraterpenoid ethers, lycopanerols I−L (5−8), were isolated from a culture of a strain of the green microalga Botryococcus braunii (L race). The structures were determined by means of spectral analyses and chemical degradation. The relative stereochemistry of these ethers was established by ROESY NMR. A biogenetic relationship is proposed between lycopanerols and lycopadiene (1), the acyclic diunsaturated tetraterpene hydrocarbon synthesized by the alga.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>12828460</pmid><doi>10.1021/np020604b</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2003-06, Vol.66 (6), p.772-778 |
| issn | 0163-3864 1520-6025 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_73431839 |
| source | ACS Publications; MEDLINE |
| subjects | acetic acids Analytical, structural and metabolic biochemistry benzene biochemical pathways Biological and medical sciences biosynthesis Botryococcus Botryococcus braunii carbon chemical structure Chlorophyta - chemistry Chlorophyta - metabolism Cote d'Ivoire epoxides ethers Ethers - chemistry Ethers - isolation & purification Fundamental and applied biological sciences. Psychology furans lycopadiene lycopane Lycopanerols methine microalgae Molecular Structure natural products Nuclear Magnetic Resonance, Biomolecular olefin Other biological molecules phytochemicals plant extracts protons spectral analysis Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization stereochemistry Terpenes - chemistry Terpenes - isolation & purification Terpenes, steroids. Hormones terpenoids tetrahydrofuran tetratepenoid ethers Tetraterpenoid ethers |
| title | Lycopanerols I−L, Four New Tetraterpenoid Ethers from Botryococcus braunii |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-28T08%3A26%3A31IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Lycopanerols%20I%E2%88%92L,%20Four%20New%20Tetraterpenoid%20Ethers%20from%20Botryococcus%20braunii&rft.jtitle=Journal%20of%20natural%20products%20(Washington,%20D.C.)&rft.au=Metzger,%20Pierre&rft.date=2003-06-01&rft.volume=66&rft.issue=6&rft.spage=772&rft.epage=778&rft.pages=772-778&rft.issn=0163-3864&rft.eissn=1520-6025&rft.coden=JNPRDF&rft_id=info:doi/10.1021/np020604b&rft_dat=%3Cproquest_cross%3E18871460%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=18871460&rft_id=info:pmid/12828460&rfr_iscdi=true |