Four new bioactive lobane diterpenes of the soft coral Lobophytum pauciflorum from Mindoro, Philippines
The marine soft coral Lobophytum pauciflorum collected from Mindoro Island, Philippines, yielded four new lobane diterpene derivatives: the acetate congeners of epoxylobatrienol and lobatrienediol (2 and 7, respectively), a methoxyl congener of lobatetraene (10), and an oxepin congener of lobatriene...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 1998-03, Vol.61 (3), p.358-361 |
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| creator | Edrada, R.A Proksch, P Wray, V Witte, L Ofwegen, L. van |
| description | The marine soft coral Lobophytum pauciflorum collected from Mindoro Island, Philippines, yielded four new lobane diterpene derivatives: the acetate congeners of epoxylobatrienol and lobatrienediol (2 and 7, respectively), a methoxyl congener of lobatetraene (10), and an oxepin congener of lobatrienetriol (11), and six known derivatives (1, 3-6, and 8). The structures of the new compounds were unambiguously established on the basis of NMR spectroscopic (1H, 13C, COSY, 1H-detected direct, and long-range 13C-1H correlations) and mass spectrometric (EIMS) data. All of the compounds were active against the phytopathogenic fungus Cladosporium cucumerinum. Compound 1 was found to be active against the Gram-positive bacteria Bacillus subtilis and the yeast Saccharomyces cerevisiae. The isolated lobane diterpenes were also active in the brine shrimp lethality test. In the latter bioassay, compounds 8 and 10 were the most active congeners with LC50's of 0.64 and 4.18 micrograms/mL, respectively. |
| doi_str_mv | 10.1021/np970276t |
| format | Article |
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The structures of the new compounds were unambiguously established on the basis of NMR spectroscopic (1H, 13C, COSY, 1H-detected direct, and long-range 13C-1H correlations) and mass spectrometric (EIMS) data. All of the compounds were active against the phytopathogenic fungus Cladosporium cucumerinum. Compound 1 was found to be active against the Gram-positive bacteria Bacillus subtilis and the yeast Saccharomyces cerevisiae. The isolated lobane diterpenes were also active in the brine shrimp lethality test. In the latter bioassay, compounds 8 and 10 were the most active congeners with LC50's of 0.64 and 4.18 micrograms/mL, respectively.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np970276t</identifier><identifier>PMID: 9548875</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>AGENT PATHOGENE ; Animals ; Anti-Bacterial Agents ; Anti-Infective Agents - isolation & purification ; Anti-Infective Agents - pharmacology ; ANTIBACTERIAL PROPERTIES ; ANTIFUNGAL PROPERTIES ; ANTIMICROBIAL PROPERTIES ; Antineoplastic Agents - pharmacology ; Artemia ; BACILLUS SUBTILIS ; Bacteria - drug effects ; BIOASSAYS ; Biological and medical sciences ; CHEMICAL COMPOSITION ; CHEMICAL STRUCTURE ; CLADOSPORIUM CUCUMERINUM ; Cnidaria - chemistry ; COMPOSICION QUIMICA ; COMPOSITION CHIMIQUE ; CORAIL ; CORALES ; CORALS ; CREVETTE ; Diterpenes - isolation & purification ; Diterpenes - pharmacology ; DITERPENOIDE ; DITERPENOIDS ; DITERPENOS ; Drug Screening Assays, Antitumor ; ENSAYO BIOLOGICO ; ESPECTROMETRIA ; ESTRUCTURA QUIMICA ; FILIPINAS ; Fungi - drug effects ; GAMBAS Y CAMARONES ; General pharmacology ; Magnetic Resonance Spectroscopy ; Medical sciences ; MICOSIS ; Microbial Sensitivity Tests ; MYCOSE ; MYCOSES ; ORGANISMOS PATOGENOS ; PATHOGENS ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; PHILIPPINES ; PRAWNS AND SHRIMPS ; PROPIEDADES ANTIMICOSICAS ; PROPIEDADES ANTIMICROBIANAS ; PROPRIETE ANTIFONGIQUE ; PROPRIETE ANTIMICROBIENNE ; SACCHAROMYCES CEREVISIAE ; SPECTRAL ANALYSIS ; SPECTROMETRIE ; SPECTROMETRY ; STRUCTURE CHIMIQUE ; SUBSTANCE TOXIQUE ; SUSTANCIAS TOXICAS ; TEST BIOLOGIQUE ; TOXIC SUBSTANCES</subject><ispartof>Journal of natural products (Washington, D.C.), 1998-03, Vol.61 (3), p.358-361</ispartof><rights>1998 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2209519$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9548875$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Edrada, R.A</creatorcontrib><creatorcontrib>Proksch, P</creatorcontrib><creatorcontrib>Wray, V</creatorcontrib><creatorcontrib>Witte, L</creatorcontrib><creatorcontrib>Ofwegen, L. van</creatorcontrib><title>Four new bioactive lobane diterpenes of the soft coral Lobophytum pauciflorum from Mindoro, Philippines</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>The marine soft coral Lobophytum pauciflorum collected from Mindoro Island, Philippines, yielded four new lobane diterpene derivatives: the acetate congeners of epoxylobatrienol and lobatrienediol (2 and 7, respectively), a methoxyl congener of lobatetraene (10), and an oxepin congener of lobatrienetriol (11), and six known derivatives (1, 3-6, and 8). The structures of the new compounds were unambiguously established on the basis of NMR spectroscopic (1H, 13C, COSY, 1H-detected direct, and long-range 13C-1H correlations) and mass spectrometric (EIMS) data. All of the compounds were active against the phytopathogenic fungus Cladosporium cucumerinum. Compound 1 was found to be active against the Gram-positive bacteria Bacillus subtilis and the yeast Saccharomyces cerevisiae. The isolated lobane diterpenes were also active in the brine shrimp lethality test. In the latter bioassay, compounds 8 and 10 were the most active congeners with LC50's of 0.64 and 4.18 micrograms/mL, respectively.</description><subject>AGENT PATHOGENE</subject><subject>Animals</subject><subject>Anti-Bacterial Agents</subject><subject>Anti-Infective Agents - isolation & purification</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>ANTIBACTERIAL PROPERTIES</subject><subject>ANTIFUNGAL PROPERTIES</subject><subject>ANTIMICROBIAL PROPERTIES</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Artemia</subject><subject>BACILLUS SUBTILIS</subject><subject>Bacteria - drug effects</subject><subject>BIOASSAYS</subject><subject>Biological and medical sciences</subject><subject>CHEMICAL COMPOSITION</subject><subject>CHEMICAL STRUCTURE</subject><subject>CLADOSPORIUM CUCUMERINUM</subject><subject>Cnidaria - chemistry</subject><subject>COMPOSICION QUIMICA</subject><subject>COMPOSITION CHIMIQUE</subject><subject>CORAIL</subject><subject>CORALES</subject><subject>CORALS</subject><subject>CREVETTE</subject><subject>Diterpenes - isolation & purification</subject><subject>Diterpenes - pharmacology</subject><subject>DITERPENOIDE</subject><subject>DITERPENOIDS</subject><subject>DITERPENOS</subject><subject>Drug Screening Assays, Antitumor</subject><subject>ENSAYO BIOLOGICO</subject><subject>ESPECTROMETRIA</subject><subject>ESTRUCTURA QUIMICA</subject><subject>FILIPINAS</subject><subject>Fungi - drug effects</subject><subject>GAMBAS Y CAMARONES</subject><subject>General pharmacology</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>MICOSIS</subject><subject>Microbial Sensitivity Tests</subject><subject>MYCOSE</subject><subject>MYCOSES</subject><subject>ORGANISMOS PATOGENOS</subject><subject>PATHOGENS</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>PHILIPPINES</subject><subject>PRAWNS AND SHRIMPS</subject><subject>PROPIEDADES ANTIMICOSICAS</subject><subject>PROPIEDADES ANTIMICROBIANAS</subject><subject>PROPRIETE ANTIFONGIQUE</subject><subject>PROPRIETE ANTIMICROBIENNE</subject><subject>SACCHAROMYCES CEREVISIAE</subject><subject>SPECTRAL ANALYSIS</subject><subject>SPECTROMETRIE</subject><subject>SPECTROMETRY</subject><subject>STRUCTURE CHIMIQUE</subject><subject>SUBSTANCE TOXIQUE</subject><subject>SUSTANCIAS TOXICAS</subject><subject>TEST BIOLOGIQUE</subject><subject>TOXIC SUBSTANCES</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1998</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkUFr3DAQhUVpSTdpD_kBAR1KTnE7kizJOpYlaRK2dCHbSy9CtqWsWttyJLlt_n0EWZLTDLyPN7w3CJ0S-EyAki_TrCRQKfIbtCKcQiWA8rdoBUSwijWifo-OU_oNAAwUP0JHitdNI_kK3V-FJeLJ_sOtD6bL_q_FQ2jNZHHvs42znWzCweG8tzgFl3EXohnwJrRh3j_mZcSzWTrvhhDL7mIY8Xc_9SGGC7zd-8HPsy8WH9A7Z4ZkPx7mCdpdXe7W19Xmx7eb9ddN5ZgguaIMCFhjaScMl4YS1bJa1M7WjBLGKKfGyB6sUI20nBEuGDAFpGQR0NfsBJ0_284xPCw2ZT361NlhKIHCkrRUDRONaAp4dgCXdrS9nqMfTXzUh2KK_umgm9SZwUUzdT69YJSWHokqWPWM-ZTt_xfZxD9aSCa53m3vtNrC9fq2Bv3r9awzQZv7WCx_3hFVvicplYQ9AUdWiFk</recordid><startdate>19980301</startdate><enddate>19980301</enddate><creator>Edrada, R.A</creator><creator>Proksch, P</creator><creator>Wray, V</creator><creator>Witte, L</creator><creator>Ofwegen, L. van</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>7X8</scope></search><sort><creationdate>19980301</creationdate><title>Four new bioactive lobane diterpenes of the soft coral Lobophytum pauciflorum from Mindoro, Philippines</title><author>Edrada, R.A ; Proksch, P ; Wray, V ; Witte, L ; Ofwegen, L. van</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-f361t-23010eae2c6a57a219b3464fe432133252aa7d0e6987e5315630390187560d43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1998</creationdate><topic>AGENT PATHOGENE</topic><topic>Animals</topic><topic>Anti-Bacterial Agents</topic><topic>Anti-Infective Agents - isolation & purification</topic><topic>Anti-Infective Agents - pharmacology</topic><topic>ANTIBACTERIAL PROPERTIES</topic><topic>ANTIFUNGAL PROPERTIES</topic><topic>ANTIMICROBIAL PROPERTIES</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Artemia</topic><topic>BACILLUS SUBTILIS</topic><topic>Bacteria - drug effects</topic><topic>BIOASSAYS</topic><topic>Biological and medical sciences</topic><topic>CHEMICAL COMPOSITION</topic><topic>CHEMICAL STRUCTURE</topic><topic>CLADOSPORIUM CUCUMERINUM</topic><topic>Cnidaria - chemistry</topic><topic>COMPOSICION QUIMICA</topic><topic>COMPOSITION CHIMIQUE</topic><topic>CORAIL</topic><topic>CORALES</topic><topic>CORALS</topic><topic>CREVETTE</topic><topic>Diterpenes - isolation & purification</topic><topic>Diterpenes - pharmacology</topic><topic>DITERPENOIDE</topic><topic>DITERPENOIDS</topic><topic>DITERPENOS</topic><topic>Drug Screening Assays, Antitumor</topic><topic>ENSAYO BIOLOGICO</topic><topic>ESPECTROMETRIA</topic><topic>ESTRUCTURA QUIMICA</topic><topic>FILIPINAS</topic><topic>Fungi - drug effects</topic><topic>GAMBAS Y CAMARONES</topic><topic>General pharmacology</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>MICOSIS</topic><topic>Microbial Sensitivity Tests</topic><topic>MYCOSE</topic><topic>MYCOSES</topic><topic>ORGANISMOS PATOGENOS</topic><topic>PATHOGENS</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>PHILIPPINES</topic><topic>PRAWNS AND SHRIMPS</topic><topic>PROPIEDADES ANTIMICOSICAS</topic><topic>PROPIEDADES ANTIMICROBIANAS</topic><topic>PROPRIETE ANTIFONGIQUE</topic><topic>PROPRIETE ANTIMICROBIENNE</topic><topic>SACCHAROMYCES CEREVISIAE</topic><topic>SPECTRAL ANALYSIS</topic><topic>SPECTROMETRIE</topic><topic>SPECTROMETRY</topic><topic>STRUCTURE CHIMIQUE</topic><topic>SUBSTANCE TOXIQUE</topic><topic>SUSTANCIAS TOXICAS</topic><topic>TEST BIOLOGIQUE</topic><topic>TOXIC SUBSTANCES</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Edrada, R.A</creatorcontrib><creatorcontrib>Proksch, P</creatorcontrib><creatorcontrib>Wray, V</creatorcontrib><creatorcontrib>Witte, L</creatorcontrib><creatorcontrib>Ofwegen, L. van</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>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>Edrada, R.A</au><au>Proksch, P</au><au>Wray, V</au><au>Witte, L</au><au>Ofwegen, L. van</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Four new bioactive lobane diterpenes of the soft coral Lobophytum pauciflorum from Mindoro, Philippines</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>1998-03-01</date><risdate>1998</risdate><volume>61</volume><issue>3</issue><spage>358</spage><epage>361</epage><pages>358-361</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>The marine soft coral Lobophytum pauciflorum collected from Mindoro Island, Philippines, yielded four new lobane diterpene derivatives: the acetate congeners of epoxylobatrienol and lobatrienediol (2 and 7, respectively), a methoxyl congener of lobatetraene (10), and an oxepin congener of lobatrienetriol (11), and six known derivatives (1, 3-6, and 8). The structures of the new compounds were unambiguously established on the basis of NMR spectroscopic (1H, 13C, COSY, 1H-detected direct, and long-range 13C-1H correlations) and mass spectrometric (EIMS) data. All of the compounds were active against the phytopathogenic fungus Cladosporium cucumerinum. Compound 1 was found to be active against the Gram-positive bacteria Bacillus subtilis and the yeast Saccharomyces cerevisiae. The isolated lobane diterpenes were also active in the brine shrimp lethality test. In the latter bioassay, compounds 8 and 10 were the most active congeners with LC50's of 0.64 and 4.18 micrograms/mL, respectively.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>9548875</pmid><doi>10.1021/np970276t</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 1998-03, Vol.61 (3), p.358-361 |
| issn | 0163-3864 1520-6025 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_79836868 |
| source | MEDLINE; ACS Publications |
| subjects | AGENT PATHOGENE Animals Anti-Bacterial Agents Anti-Infective Agents - isolation & purification Anti-Infective Agents - pharmacology ANTIBACTERIAL PROPERTIES ANTIFUNGAL PROPERTIES ANTIMICROBIAL PROPERTIES Antineoplastic Agents - pharmacology Artemia BACILLUS SUBTILIS Bacteria - drug effects BIOASSAYS Biological and medical sciences CHEMICAL COMPOSITION CHEMICAL STRUCTURE CLADOSPORIUM CUCUMERINUM Cnidaria - chemistry COMPOSICION QUIMICA COMPOSITION CHIMIQUE CORAIL CORALES CORALS CREVETTE Diterpenes - isolation & purification Diterpenes - pharmacology DITERPENOIDE DITERPENOIDS DITERPENOS Drug Screening Assays, Antitumor ENSAYO BIOLOGICO ESPECTROMETRIA ESTRUCTURA QUIMICA FILIPINAS Fungi - drug effects GAMBAS Y CAMARONES General pharmacology Magnetic Resonance Spectroscopy Medical sciences MICOSIS Microbial Sensitivity Tests MYCOSE MYCOSES ORGANISMOS PATOGENOS PATHOGENS Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments PHILIPPINES PRAWNS AND SHRIMPS PROPIEDADES ANTIMICOSICAS PROPIEDADES ANTIMICROBIANAS PROPRIETE ANTIFONGIQUE PROPRIETE ANTIMICROBIENNE SACCHAROMYCES CEREVISIAE SPECTRAL ANALYSIS SPECTROMETRIE SPECTROMETRY STRUCTURE CHIMIQUE SUBSTANCE TOXIQUE SUSTANCIAS TOXICAS TEST BIOLOGIQUE TOXIC SUBSTANCES |
| title | Four new bioactive lobane diterpenes of the soft coral Lobophytum pauciflorum from Mindoro, Philippines |
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