Illudalane Sesquiterpenoids from the Soft Coral Alcyonium paessleri: The First Natural Nitrate Esters

Fifteen illudalane sesquiterpenoids, alcyopterosins A−O (1−15) have been isolated from the subAntarctic soft coral Alcyonium paessleri which was collected at a depth of 200 m near the South Georgia Islands, and their structures were elucidated by spectroscopic techniques. Eight of these compounds (2...

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Veröffentlicht in:	Journal of organic chemistry 2000-07, Vol.65 (15), p.4482-4486
Hauptverfasser:	Palermo, Jorge A, Rodríguez Brasco, Maria Florencia, Spagnuolo, Carla, Seldes, Alicia M
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Antarctic Regions Cell Line Cnidaria - chemistry Esters - chemistry Esters - isolation & purification Esters - toxicity Humans Magnetic Resonance Spectroscopy Molecular Structure Nitrates - chemistry Nitrates - isolation & purification Nitrates - toxicity Sesquiterpenes - chemistry Sesquiterpenes - isolation & purification Sesquiterpenes - toxicity Spectroscopy, Fourier Transform Infrared
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container_issue	15
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container_title	Journal of organic chemistry
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creator	Palermo, Jorge A Rodríguez Brasco, Maria Florencia Spagnuolo, Carla Seldes, Alicia M
description	Fifteen illudalane sesquiterpenoids, alcyopterosins A−O (1−15) have been isolated from the subAntarctic soft coral Alcyonium paessleri which was collected at a depth of 200 m near the South Georgia Islands, and their structures were elucidated by spectroscopic techniques. Eight of these compounds (2, 3, 5−8, 10, and 13) are the first natural nitrate esters, while the other four (1, 4, 11, and 12) are chlorinated. These compounds are as well the first illudalane sesquiterpenoids to be isolated from the marine environment. Compounds 1, 3, 5, and 8 showed mild cytotoxicity toward human tumor cell lines.
doi_str_mv	10.1021/jo991740x
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Eight of these compounds (2, 3, 5−8, 10, and 13) are the first natural nitrate esters, while the other four (1, 4, 11, and 12) are chlorinated. These compounds are as well the first illudalane sesquiterpenoids to be isolated from the marine environment. 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Compounds 1, 3, 5, and 8 showed mild cytotoxicity toward human tumor cell lines.</description><subject>Animals</subject><subject>Antarctic Regions</subject><subject>Cell Line</subject><subject>Cnidaria - chemistry</subject><subject>Esters - chemistry</subject><subject>Esters - isolation & purification</subject><subject>Esters - toxicity</subject><subject>Humans</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Structure</subject><subject>Nitrates - chemistry</subject><subject>Nitrates - isolation & purification</subject><subject>Nitrates - toxicity</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes - isolation & purification</subject><subject>Sesquiterpenes - toxicity</subject><subject>Spectroscopy, Fourier Transform Infrared</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0L1OwzAQB3ALgWgpDLwA8sLAEHD8kQ-2qrRQqRREIwaWyLEdNSVpgu1I7cbKa_IkuAqqGLjlhvvpTvcH4NxH1z7C_s2qjmM_pGhzAPo-w8gLYkQPQR8hjD2CA9IDJ8askCvG2DHo-ShmcUSjPlhOy7KVvORrBRfKfLSFVbpR67qQBua6rqBdukmdWziqNS_hsBTbel20FWy4MqZUurj9_vyCiWOTQhsL59y2OzkvrOZWwbFxK80pOMp5adTZbx-AZDJORg_e7Ol-OhrOPE4Zsp70JQ4CnssMYapkFCERZ1FMKI5CSgTJQoJRRkkQZjQUgQi4ECznOZIRoxiRAbjq1gpdG6NVnja6qLjepj5Kd2Gl-7Ccvehs02aVkn9kl44DXgcK98JmP-f6PQ1CErI0eV6kd3gSPcavL-mb85ed58K4O61eu0__OfwDR1CB_Q</recordid><startdate>20000728</startdate><enddate>20000728</enddate><creator>Palermo, Jorge A</creator><creator>Rodríguez Brasco, Maria Florencia</creator><creator>Spagnuolo, Carla</creator><creator>Seldes, Alicia M</creator><general>American Chemical Society</general><scope>BSCLL</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></search><sort><creationdate>20000728</creationdate><title>Illudalane Sesquiterpenoids from the Soft Coral Alcyonium paessleri: The First Natural Nitrate Esters</title><author>Palermo, Jorge A ; Rodríguez Brasco, Maria Florencia ; Spagnuolo, Carla ; Seldes, Alicia M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a450t-d1d266afdb024ed880c9b893428743c3b7320b4367b47c6c6acc5faf0d854203</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Animals</topic><topic>Antarctic Regions</topic><topic>Cell Line</topic><topic>Cnidaria - chemistry</topic><topic>Esters - chemistry</topic><topic>Esters - isolation & purification</topic><topic>Esters - toxicity</topic><topic>Humans</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Structure</topic><topic>Nitrates - chemistry</topic><topic>Nitrates - isolation & purification</topic><topic>Nitrates - toxicity</topic><topic>Sesquiterpenes - chemistry</topic><topic>Sesquiterpenes - isolation & purification</topic><topic>Sesquiterpenes - toxicity</topic><topic>Spectroscopy, Fourier Transform Infrared</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Palermo, Jorge A</creatorcontrib><creatorcontrib>Rodríguez Brasco, Maria Florencia</creatorcontrib><creatorcontrib>Spagnuolo, Carla</creatorcontrib><creatorcontrib>Seldes, Alicia M</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Palermo, Jorge A</au><au>Rodríguez Brasco, Maria Florencia</au><au>Spagnuolo, Carla</au><au>Seldes, Alicia M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Illudalane Sesquiterpenoids from the Soft Coral Alcyonium paessleri: The First Natural Nitrate Esters</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2000-07-28</date><risdate>2000</risdate><volume>65</volume><issue>15</issue><spage>4482</spage><epage>4486</epage><pages>4482-4486</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Fifteen illudalane sesquiterpenoids, alcyopterosins A−O (1−15) have been isolated from the subAntarctic soft coral Alcyonium paessleri which was collected at a depth of 200 m near the South Georgia Islands, and their structures were elucidated by spectroscopic techniques. Eight of these compounds (2, 3, 5−8, 10, and 13) are the first natural nitrate esters, while the other four (1, 4, 11, and 12) are chlorinated. These compounds are as well the first illudalane sesquiterpenoids to be isolated from the marine environment. Compounds 1, 3, 5, and 8 showed mild cytotoxicity toward human tumor cell lines.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>10959848</pmid><doi>10.1021/jo991740x</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record>
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subjects	Animals Antarctic Regions Cell Line Cnidaria - chemistry Esters - chemistry Esters - isolation & purification Esters - toxicity Humans Magnetic Resonance Spectroscopy Molecular Structure Nitrates - chemistry Nitrates - isolation & purification Nitrates - toxicity Sesquiterpenes - chemistry Sesquiterpenes - isolation & purification Sesquiterpenes - toxicity Spectroscopy, Fourier Transform Infrared
title	Illudalane Sesquiterpenoids from the Soft Coral Alcyonium paessleri: The First Natural Nitrate Esters
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