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<article xmlns:xlink="http://www.w3.org/1999/xlink" xml:lang="en" article-type="review-article">
<front>
<journal-meta>
<journal-id journal-id-type="publisher-id">MD</journal-id>
<journal-title>Marine Drugs</journal-title>
<abbrev-journal-title>MD</abbrev-journal-title>
<issn pub-type="epub">1660-3397</issn>
<publisher>
<publisher-name>Molecular Diversity Preservation International</publisher-name></publisher></journal-meta>
<article-meta>
<article-id pub-id-type="doi">10.3390/md8102569</article-id>
<article-id pub-id-type="publisher-id">marinedrugs-08-02569</article-id>
<article-categories>
<subj-group>
<subject>Review</subject></subj-group></article-categories>
<title-group>
<article-title>Demospongic Acids Revisited</article-title></title-group>
<contrib-group>
<contrib contrib-type="author">
<name><surname>Kornprobst</surname><given-names>Jean-Michel</given-names></name><xref ref-type="corresp" rid="c1-marinedrugs-08-02569">*</xref></contrib>
<contrib contrib-type="author">
<name><surname>Barnathan</surname><given-names>Gilles</given-names></name></contrib>
<aff id="af1-marinedrugs-08-02569">Groupe Mer, Molécules, Santé MMS/EA 2160, Equipe 7: Lipides marins à activité biologique, Pôle Mer et Littoral, Faculté de Pharmacie, Université de Nantes, France; E-Mail: <email>gilles.barnathan@univ-nantes.fr</email></aff></contrib-group>
<author-notes>
<corresp id="c1-marinedrugs-08-02569">*Author to whom correspondence should be addressed; E-Mail: <email>jean-michel.kornprobst@univnantes.fr</email>; Tel.: +33 2 51 12 56 89; Fax: +33 2 51 12 56 79.</corresp></author-notes>
<pub-date pub-type="collection">
<year>2010</year></pub-date>
<pub-date pub-type="epub">
<day>8</day>
<month>10</month>
<year>2010</year></pub-date>
<volume>8</volume>
<issue>10</issue>
<fpage>2569</fpage>
<lpage>2577</lpage>
<history>
<date date-type="received">
<day>7</day>
<month>9</month>
<year>2010</year></date>
<date date-type="rev-recd">
<day>27</day>
<month>9</month>
<year>2010</year></date>
<date date-type="accepted">
<day>30</day>
<month>9</month>
<year>2010</year></date></history>
<permissions>
<copyright-statement>© 2010 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland</copyright-statement>
<copyright-year>2010</copyright-year>
<license license-type="open-access" xlink:href="http://creativecommons.org/licenses/by/3.0">
<p>This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).</p></license></permissions>
<abstract>
<p>The well-known fatty acids with a Δ5,9 unsaturation system were designated for a long period as demospongic acids, taking into account that they originally occurred in marine Demospongia sponges. However, such acids have also been observed in various marine sources with a large range of chain-lengths (C<sub>16</sub>–C<sub>32</sub>) and from some terrestrial plants with short acyl chains (C<sub>18</sub>–C<sub>19</sub>). Finally, the Δ5,9 fatty acids appear to be a particular type of non-methylene-interrupted fatty acids (NMA FAs). This article reviews the occurrence of these particular fatty acids in marine and terrestrial organisms and shows the biosynthetic connections between Δ5,9 fatty acids and other NMI FAs.</p></abstract>
<kwd-group>
<kwd>demospongic acids</kwd>
<kwd>marine lipids</kwd>
<kwd>sponges</kwd>
<kwd>marine invertebrates</kwd>
<kwd>non-methylene interrupted fatty acids</kwd></kwd-group></article-meta></front>
<body>
<sec sec-type="intro">
<title>1. Introduction</title>
<p>The well-known notion of demospongic acid appeared for the first time in 1976 in a historical paper from Litchfield and Morales [<xref ref-type="bibr" rid="b1-marinedrugs-08-02569">1</xref>], but at that time only as «demospongiae fatty acids». In another paper published in 1980 [<xref ref-type="bibr" rid="b2-marinedrugs-08-02569">2</xref>], Litchfield <italic>et al.</italic> used the term «demospongic fatty acids» probably for the first time. Since then and up until now [<xref ref-type="bibr" rid="b3-marinedrugs-08-02569">3</xref>–<xref ref-type="bibr" rid="b5-marinedrugs-08-02569">5</xref>], this term has widely been used. However, about 35 years after Litchfield’s work on sponge lipids, the notion of demospongic acid seems to no longer have significance, mainly due to their controversial definition and to their wide distribution among marine invertebrates and some terrestrial plants. At the time, it seemed to be of interest to precisely identify the function of demospongic acids, in consideration of their biological activities as topoisomerase inhibitors or against cancer cells as recently reviewed [<xref ref-type="bibr" rid="b6-marinedrugs-08-02569">6</xref>], whereas the biological interests of terrestrial short-chain Δ5,9 fatty acids (FAs) had already been demonstrated [<xref ref-type="bibr" rid="b7-marinedrugs-08-02569">7</xref>,<xref ref-type="bibr" rid="b8-marinedrugs-08-02569">8</xref>].</p></sec>
<sec>
<title>2. What Exactly Is a Demospongic Acid?</title>
<p>The definition of a demospongic acid has never been very clear [<xref ref-type="bibr" rid="b1-marinedrugs-08-02569">1</xref>,<xref ref-type="bibr" rid="b2-marinedrugs-08-02569">2</xref>]. In their first papers, Litchfield <italic>et al</italic>. only mentioned very long-chain C<sub>24</sub>–C<sub>30</sub> or C<sub>24</sub>–C<sub>34</sub> acids with the unusual 5,9 unsaturation pattern, but at that time, only fatty acids with an even number of carbons had been found [<xref ref-type="bibr" rid="b1-marinedrugs-08-02569">1</xref>,<xref ref-type="bibr" rid="b9-marinedrugs-08-02569">9</xref>]. In the 1980s, a lot of work was published on sponge FAs, and it became apparent that “demospongic acids” also contained all odd FAs from C<sub>23</sub>–C<sub>31</sub> [<xref ref-type="bibr" rid="b10-marinedrugs-08-02569">10</xref>]. Within this field of research, a consensus was quickly established that agreed that demospongic acids were very long-chain fatty acids, mainly C<sub>24</sub>–C<sub>30</sub>, with the atypical 5,9-diunsaturation system, independent of the total number of double bonds. Some years later—and due to many papers being devoted to FAs from sponges—it appeared that:</p>
<list list-type="roman-lower">
<list-item>
<p>the distinction between long-chain fatty acids (LCFAs, C<sub>20</sub>–C<sub>22</sub> ?) and very long-chain FAs (VLCFAs, ≥C<sub>23</sub> ?) is not clear and often depends on the authors’ interpretation [<xref ref-type="bibr" rid="b10-marinedrugs-08-02569">10</xref>–<xref ref-type="bibr" rid="b17-marinedrugs-08-02569">17</xref>].</p></list-item>
<list-item>
<p>the presence of the ever-mentioned 5,9-diunsaturation pattern cannot be considered as characteristic of “demospongic acids” due to the elongation process during their biosynthetic pathways, and diunsaturations such as 5,9-, 7,11-, 9,13-, 11,15-, 17,21-, 19,23- 21,25- and 23,27- can be considered as being similar [<xref ref-type="bibr" rid="b18-marinedrugs-08-02569">18</xref>], but other dienoic patterns with short chains such as 6,11-18:2 and 6,11-20:2 have also been considered as “demospongic” acids [<xref ref-type="bibr" rid="b19-marinedrugs-08-02569">19</xref>]. Furthermore, several “demospongic acids” display <italic>E</italic> and <italic>Z</italic> configurations for Δ5 and Δ9 double bonds [<xref ref-type="bibr" rid="b20-marinedrugs-08-02569">20</xref>].</p></list-item></list>
<p>Currently, the best definition for a demospongic acid would be that of Christie [<xref ref-type="bibr" rid="b18-marinedrugs-08-02569">18</xref>], stating “<italic>bis</italic><italic>-methylene-interrupted cis-double bonds, ranging in chain-length from C</italic><italic><sub>16</sub></italic> <italic>to C</italic><italic><sub>34</sub></italic> <italic>with a</italic> <italic>cis, cis</italic><italic>-dienoic system, either with the double bonds in position 5 and 9, or derived from 5,9-16:2 by chain elongation</italic>”.</p>
<p>At present, the question is whether such acids are not at all specific to demosponges, but have been found in other groups of sponges, especially among hexactinellida, in different phyla of marine invertebrates and in several species of terrestrial plants, especially conifers, and in some species of Apocynaceae, Malvaceae, and Ranunculaceae.</p></sec>
<sec>
<title>3. Occurrence of “Demospongic” Acids among Other Organisms</title>
<p><xref ref-type="table" rid="t1-marinedrugs-08-02569">Table 1</xref> presents a non-exhaustive list of more than 40 FAs that correspond to Christie’s definition of demospongic acids found in microorganisms, marine invertebrates and terrestrial plants. A particularly interesting point is the presence of 6-Br-5,9-FAs that are very common in demosponges but quite rare in other organisms. To the best of our knowledge only some Cnidaria Hexacorallia were shown to contain these brominated FAs [<xref ref-type="bibr" rid="b21-marinedrugs-08-02569">21</xref>–<xref ref-type="bibr" rid="b23-marinedrugs-08-02569">23</xref>], which prove the existence of bromoperoxidases in this group of Cnidaria since it has been proved that these brominated demospongic acids are synthesized by the sponge itself in the final stage of biosynthesis [<xref ref-type="bibr" rid="b24-marinedrugs-08-02569">24</xref>].</p></sec>
<sec>
<title>4. Towards a Classification of Non-Methylene-Interrupted Fatty Acids?</title>
<p>Demospongic acids represent a particular type of non-methylene-interrupted FA and, according to Christie’s definition, it could be interesting to consider at least three classes of non-methylene-interrupted fatty acids (NMI FAs) depending on the number of methylene groups situated between the two first double bonds. Then, group 1 would contain all <italic>bis</italic>-methylene-interrupted <italic>cis-</italic>double bonds and would correspond to the series 5,9; 7,11; 9,13… dienoic or polyenoic acids (demospongic acids). Group 2 would be that of <italic>tetra</italic>-methylene-interrupted <italic>cis-</italic>double bonds and would contain the series 5,11; 7,13; 9,15… NMI FAs, such as the acids 7,13-20:2 found in the Brittle star (Echinoderm, Ophiuroidea) <italic>Ophiura sarsi</italic> [<xref ref-type="bibr" rid="b37-marinedrugs-08-02569">37</xref>] and in the maritime pine <italic>Pinus pisaster</italic> [<xref ref-type="bibr" rid="b29-marinedrugs-08-02569">29</xref>], or the acid 7,13-22:2 found in the sponge <italic>Petrosia ficiformis</italic> [<xref ref-type="bibr" rid="b38-marinedrugs-08-02569">38</xref>]. Finally, group 3 would contain <italic>hexa</italic>methylene-interrupted <italic>cis-</italic>double bonds corresponding to the series 5,13; 7,15; 9,17… NMI FAs, such as the acid 7,15-20:2 found in the sponge <italic>Dysidea fragilis</italic> [<xref ref-type="bibr" rid="b39-marinedrugs-08-02569">39</xref>]. Some other acids of these three groups have been identified in marine invertebrates, especially molluscs and arthropods, and in numerous terrestrial plants, especially gymnosperms, and all of them can be deduced from accepted biosynthetic pathways implying elongases and 5- and 9-desaturases. <xref ref-type="fig" rid="f1-marinedrugs-08-02569">Figures 1</xref> and <xref ref-type="fig" rid="f2-marinedrugs-08-02569">2</xref> give an overview of these putative biosyntheses from palmitic acid (16:0), palmitoleic acid (9-16:1) and linoleic acid (9,12-18:2). These schemes are currently used and have appeared recently in several publications, along with recent reviews on elongases and polyketide synthases [<xref ref-type="bibr" rid="b3-marinedrugs-08-02569">3</xref>,<xref ref-type="bibr" rid="b9-marinedrugs-08-02569">9</xref>,<xref ref-type="bibr" rid="b10-marinedrugs-08-02569">10</xref>,<xref ref-type="bibr" rid="b12-marinedrugs-08-02569">12</xref>,<xref ref-type="bibr" rid="b40-marinedrugs-08-02569">40</xref>–<xref ref-type="bibr" rid="b44-marinedrugs-08-02569">44</xref>].</p></sec>
<sec>
<title>5. Conclusion</title>
<p>To end this point of view, we think that the former notion of demospongic acid should no longer be used mainly because <italic>bis</italic>-methylene interrupted 5,9-diunsaturated FAs and related acids are distributed among several phyla of marine organisms and several classes of terrestrial plants. The former “demospongic acids” can be considered as a particular series of NMI FAs produced by different combinations of elongases and Δ5 and Δ9 desaturases on the most common FAs in nature such as palmitic and palmitoleic acids.</p></sec></body>
<back>
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<sec sec-type="display-objects">
<title>Figures and Table</title>
<fig id="f1-marinedrugs-08-02569" position="float">
<label>Figure 1</label>
<caption>
<p>Currently accepted pathways for the main long-chain NMI FAs (≤C<sub>24</sub>)</p>
<p>E: elongase; nDs: n-desaturase</p>
<p>All framed NMI FAs have been identified in several marine invertebrates and terrestrial plants.</p></caption><graphic xlink:href="marinedrugs-08-02569f1.gif"/></fig>
<fig id="f2-marinedrugs-08-02569" position="float">
<label>Figure 2</label>
<caption>
<p>Currently accepted pathways for the main very long-chain NMI FAs (&gt;C<sub>24</sub>)</p>
<p>E: elongase; nDs: n-desaturase</p>
<p>All framed NMI FAs have been identified in several marine invertebrates and terrestrial plants.</p>
<p>*Biosynthesis demonstrated in <italic>Microciona prolifera [</italic>3]</p>
<p>**Although they are very likely the acids 5,19-26:2, 5,21-28:2, 9,21-28:2 and 5,23-30:2 are still hypothetical.</p></caption><graphic xlink:href="marinedrugs-08-02569f2.gif"/></fig>
<table-wrap id="t1-marinedrugs-08-02569" position="float">
<label>Table 1</label>
<caption>
<p>Occurrence of “demospongic”<xref ref-type="table-fn" rid="tfn1-marinedrugs-08-02569">*</xref> acids in organisms that are not demosponges.</p></caption>
<table frame="hsides" rules="groups">
<thead>
<tr>
<th align="left" valign="bottom">Acids</th>
<th align="left" valign="bottom">Genera/species</th>
<th align="left" valign="bottom">Kind of organisms</th>
<th align="left" valign="bottom">Ref.</th></tr></thead>
<tbody>
<tr>
<td align="left" valign="top">5,9-16:2</td>
<td align="left" valign="top"><italic>Stoichactis helianthus</italic></td>
<td align="left" valign="top">Cnidaria (Hexacorallia)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b22-marinedrugs-08-02569">22</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9-17:2</td>
<td align="left" valign="top"><italic>Dictyostelium discoideum</italic></td>
<td align="left" valign="top">Microorganism, soil-living amoeba</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b25-marinedrugs-08-02569">25</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top" rowspan="4">5,9-18:2 taxoleic acd</td>
<td align="left" valign="top"><italic>Condylactis gigantea</italic>, <italic>Palythoa caribaeorum</italic>, <italic>Stoichactis helianthus</italic></td>
<td align="left" valign="top">Cnidaria (Hexacorallia)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b22-marinedrugs-08-02569">22</xref>,<xref ref-type="bibr" rid="b23-marinedrugs-08-02569">23</xref>]</td></tr>
<tr>
<td align="left" valign="top"><italic>Cellana grata</italic>, <italic>Collisella dorsuosa</italic></td>
<td align="left" valign="top">Marine molluscs</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b26-marinedrugs-08-02569">26</xref>,<xref ref-type="bibr" rid="b27-marinedrugs-08-02569">27</xref>]</td></tr>
<tr>
<td align="left" valign="top"><italic>Tripneustes esculentus</italic></td>
<td align="left" valign="top">Echinoderm</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b28-marinedrugs-08-02569">28</xref>]</td></tr>
<tr>
<td align="left" valign="top"><italic>Ginkgo biloba</italic></td>
<td align="left" valign="top">Terrestrial plant</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b7-marinedrugs-08-02569">7</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top" rowspan="2">5,9,12-18:3 pinolenic acid (<italic>Z</italic>,<italic>Z</italic>,<italic>Z</italic>) and/or columbinic acid(<italic>E</italic>,<italic>Z</italic>,<italic>Z</italic>)</td>
<td align="left" valign="top"><italic>Abies</italic> sp., <italic>Cedrus</italic> sp., <italic>Cupressus</italic> sp., <italic>Juniperus</italic> sp., <italic>Laryx</italic> sp., <italic>Picea</italic> sp., <italic>Pinus</italic> sp., <italic>Sequoia</italic> sp., <italic>Thuya</italic> sp.</td>
<td align="left" valign="top">Terrestrial plants (conifers, gymnosperms)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b8-marinedrugs-08-02569">8</xref>,<xref ref-type="bibr" rid="b29-marinedrugs-08-02569">29</xref>]</td></tr>
<tr>
<td align="left" valign="top"><italic>Anemone leveillei</italic> (Ranunculaceae)</td><td align="left" valign="top"/>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b30-marinedrugs-08-02569">30</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top" rowspan="2">5,9,12,15-18:4</td>
<td align="left" valign="top"><italic>Perna canaliculus</italic></td>
<td align="left" valign="top">Marine mollusc (Lamellibranchiata)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b31-marinedrugs-08-02569">31</xref>]</td></tr>
<tr>
<td align="left" valign="top"><italic>Abies</italic> sp., <italic>Cedrus</italic> sp., <italic>Cupressus</italic> sp., <italic>Juniperus</italic> sp., <italic>Laryx</italic> sp., <italic>Picea</italic> sp., <italic>Sequoia</italic> sp., <italic>Thuya</italic> sp.</td>
<td align="left" valign="top">Terrestrial plants (conifers)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b8-marinedrugs-08-02569">8</xref>,<xref ref-type="bibr" rid="b29-marinedrugs-08-02569">29</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9-19:2</td>
<td align="left" valign="top"><italic>Allamanda cathartica</italic> (Apocynaceae)<break/><italic>Malvaviscus arboreus</italic> (Malvaceae)</td>
<td align="left" valign="top">Terrestrial plants (angiosperms)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b32-marinedrugs-08-02569">32</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top"><italic>i</italic>-5,9-19:2</td>
<td align="left" valign="top"><italic>Allamanda cathartica</italic> (Apocynaceae)<break/><italic>Malvaviscus arboreus</italic> (Malvaceae)</td>
<td align="left" valign="top">Terrestrial plants (angiosperms)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b32-marinedrugs-08-02569">32</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top"><italic>ai</italic>-5,9-19:2</td>
<td align="left" valign="top"><italic>Allamanda cathartica</italic> (Apocynaceae)<break/><italic>Malvaviscus arboreus</italic> (Malvaceae)</td>
<td align="left" valign="top">Terrestrial plants (angiosperms)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b32-marinedrugs-08-02569">32</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9,12,16-19:4</td>
<td align="left" valign="top"><italic>Perna canaliculus</italic></td>
<td align="left" valign="top">Marine mollusc (Lamellibranchiata)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b31-marinedrugs-08-02569">31</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9-20:2</td>
<td align="left" valign="top"><italic>Condylactis gigantea</italic>, <italic>Palythoa caribaeorum</italic>, <italic>Stoichactis helianthus</italic></td>
<td align="left" valign="top">Cnidaria (Hexacorallia)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b22-marinedrugs-08-02569">22</xref>,<xref ref-type="bibr" rid="b23-marinedrugs-08-02569">23</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">6-Br,5,9-20:2</td>
<td align="left" valign="top"><italic>Condylactis gigantea</italic>, <italic>Palythoa caribaeorum</italic></td>
<td align="left" valign="top">Cnidaria (Hexacorallia)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b22-marinedrugs-08-02569">22</xref>,<xref ref-type="bibr" rid="b23-marinedrugs-08-02569">23</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">7,11-20:2</td>
<td align="left" valign="top"><italic>Penaeus setiferus</italic></td>
<td align="left" valign="top">Arthropod (shrimp)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b33-marinedrugs-08-02569">33</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9-21:2</td>
<td align="left" valign="top"><italic>Condylactis gigantea</italic>, <italic>Stoichactis helianthus</italic></td>
<td align="left" valign="top">Cnidaria (Hexacorallia)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b22-marinedrugs-08-02569">22</xref>,<xref ref-type="bibr" rid="b23-marinedrugs-08-02569">23</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">6-Br,5,9-21:2</td>
<td align="left" valign="top"><italic>Stoichactis helianthus</italic></td>
<td align="left" valign="top">Cnidaria (Hexacorallia)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b22-marinedrugs-08-02569">22</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9,12,15,18-21:5</td>
<td align="left" valign="top"><italic>Perna canaliculus</italic></td>
<td align="left" valign="top">Marine mollusc</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b23-marinedrugs-08-02569">23</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top" rowspan="2">5,9-22:2</td>
<td align="left" valign="top"><italic>Condylactis gigantea</italic>, <italic>Palythoa caribaeorum</italic>, <italic>Stoichactis helianthus</italic></td>
<td align="left" valign="top">Cnidaria (Hexacorallia)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b22-marinedrugs-08-02569">22</xref>,<xref ref-type="bibr" rid="b23-marinedrugs-08-02569">23</xref>]</td></tr>
<tr>
<td align="left" valign="top"><italic>Cellana grata</italic>, <italic>Collisella dorsuosa</italic></td>
<td align="left" valign="top">Marine molluscs</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b26-marinedrugs-08-02569">26</xref>–<xref ref-type="bibr" rid="b27-marinedrugs-08-02569">27</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">6-Br,5,9-22:2</td>
<td align="left" valign="top"><italic>Stoichactis helianthus</italic></td>
<td align="left" valign="top">Cnidaria (Hexacorallia)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b22-marinedrugs-08-02569">22</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">9,13-22:2</td>
<td align="left" valign="top"><italic>Penaeus setiferus</italic></td>
<td align="left" valign="top">Arthropod (shrimp)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b33-marinedrugs-08-02569">33</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9,15-22:3</td>
<td align="left" valign="top"><italic>Collisella dorsuosa</italic></td>
<td align="left" valign="top">Marine molluscs</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b27-marinedrugs-08-02569">27</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9,19-22:3</td>
<td align="left" valign="top"><italic>Stoichactis helianthus</italic></td>
<td align="left" valign="top">Cnidaria (Hexacorallia)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b22-marinedrugs-08-02569">22</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9-23:2</td>
<td align="left" valign="top"><italic>Stoichactis helianthus</italic></td>
<td align="left" valign="top">Cnidaria (Hexacorallia)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b22-marinedrugs-08-02569">22</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top" rowspan="2">5,9-24:2</td>
<td align="left" valign="top"><italic>Condylactis gigantea</italic>, <italic>Palythoa caribaeorum</italic></td>
<td align="left" valign="top">Cnidaria (Hexacorallia)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b23-marinedrugs-08-02569">23</xref>]</td></tr>
<tr>
<td align="left" valign="top"><italic>Cellana grata</italic>, <italic>Chromodoris</italic> sp., <italic>Collisella dorsuosa</italic>, <italic>Phyllidia coelesti</italic></td>
<td align="left" valign="top">Marine molluscs</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b26-marinedrugs-08-02569">26</xref>,<xref ref-type="bibr" rid="b27-marinedrugs-08-02569">27</xref>,<xref ref-type="bibr" rid="b34-marinedrugs-08-02569">34</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9,15-24:3</td>
<td align="left" valign="top"><italic>Cellana grata</italic>, <italic>Collisella dorsuosa</italic></td>
<td align="left" valign="top">Marine molluscs</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b26-marinedrugs-08-02569">26</xref>,<xref ref-type="bibr" rid="b27-marinedrugs-08-02569">27</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9,17-24:3</td>
<td align="left" valign="top"><italic>Cellana grata</italic>, <italic>Collisella dorsuosa</italic></td>
<td align="left" valign="top">Marine molluscs</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b26-marinedrugs-08-02569">26</xref>,<xref ref-type="bibr" rid="b27-marinedrugs-08-02569">27</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9,15,18-24:4</td>
<td align="left" valign="top"><italic>Cellana grata</italic></td>
<td align="left" valign="top">Marine mollusc</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b26-marinedrugs-08-02569">26</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9,15,18,21-24:5</td>
<td align="left" valign="top"><italic>Cellana grata</italic></td>
<td align="left" valign="top">Marine mollusc</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b26-marinedrugs-08-02569">26</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top" rowspan="2">5,9-25:2</td>
<td align="left" valign="top"><italic>Chromodoris</italic> sp., <italic>Phyllidia coelesti</italic></td>
<td align="left" valign="top">Marine molluscs</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b34-marinedrugs-08-02569">34</xref>]</td></tr>
<tr>
<td align="left" valign="top"><italic>Bebryce studeri</italic></td>
<td align="left" valign="top">Cnidaria (Octocorallia)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b35-marinedrugs-08-02569">35</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top"><italic>i</italic>-5,9-25:2</td>
<td align="left" valign="top"><italic>Phyllidia coelesti</italic></td>
<td align="left" valign="top">Marine molluscs</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b33-marinedrugs-08-02569">33</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top" rowspan="3">5,9-26:2</td>
<td align="left" valign="top"><italic>Heterochone</italic> sp.</td>
<td align="left" valign="top">Marine sponge, Hexactinellida Marine molluscs</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b36-marinedrugs-08-02569">36</xref>]</td></tr>
<tr>
<td align="left" valign="top"><italic>Chromodoris</italic> sp., <italic>Phyllidia coelesti</italic></td>
<td align="left" valign="top">Cnidaria (Octocorallia)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b34-marinedrugs-08-02569">34</xref>]</td></tr>
<tr>
<td align="left" valign="top"><italic>Bebryce studeri</italic></td><td align="left" valign="top"/>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b35-marinedrugs-08-02569">35</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top"><italic>i</italic>-5,9-26:2</td>
<td align="left" valign="top"><italic>Chromodoris</italic> sp., <italic>Phyllidia coelesti</italic></td>
<td align="left" valign="top">Marine molluscs</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b34-marinedrugs-08-02569">34</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9,19-26:3</td>
<td align="left" valign="top"><italic>Bebryce studeri</italic></td>
<td align="left" valign="top">Cnidaria (Octocorallia)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b35-marinedrugs-08-02569">35</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top" rowspan="2">5,9-28:2</td>
<td align="left" valign="top"><italic>Aulosaccus</italic> cf. <italic>mitsukuri</italic>, <italic>Heterochone</italic> sp., <italic>Rosella</italic> sp., <italic>Sympagella nux</italic></td>
<td align="left" valign="top">Marine sponges, Hexactinellida Cnidaria (Octocorallia)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b36-marinedrugs-08-02569">36</xref>]</td></tr>
<tr>
<td align="left" valign="top"><italic>Bebryce studeri</italic></td><td align="left" valign="top"/>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b35-marinedrugs-08-02569">35</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9,19-28:3</td>
<td align="left" valign="top"><italic>Bebryce studeri</italic></td>
<td align="left" valign="top">Cnidaria (Octocorallia)</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b35-marinedrugs-08-02569">35</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9,23-28:3</td>
<td align="left" valign="top"><italic>Hyalonema</italic> sp.</td>
<td align="left" valign="top">Marine sponge, Hexactinellida</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b36-marinedrugs-08-02569">36</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9-29:2</td>
<td align="left" valign="top"><italic>Hyalonema</italic> sp.</td>
<td align="left" valign="top">Marine sponge, Hexactinellida</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b36-marinedrugs-08-02569">36</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9,22-29:3</td>
<td align="left" valign="top"><italic>Acanthascus</italic> sp., <italic>Aulosaccus</italic> cf. <italic>mitsukuri</italic>, <italic>Euplectella</italic> sp., <italic>Heterochone</italic> sp., <italic>Hyalonema</italic> sp.</td>
<td align="left" valign="top">Marine sponges, Hexactinellida</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b36-marinedrugs-08-02569">36</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9,21-30:3</td>
<td align="left" valign="top"><italic>Acanthascus</italic> sp., <italic>Aulosaccus</italic> cf. <italic>mitsukuri</italic>, <italic>Euplectella</italic> sp., <italic>Hyalonema</italic> sp., <italic>Heterochone</italic> sp., <italic>Staurocalyptus</italic> sp., <italic>Sympagella nux</italic></td>
<td align="left" valign="top">Marine sponges, Hexactinellida</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b36-marinedrugs-08-02569">36</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9,23-30:3</td>
<td align="left" valign="top"><italic>Acanthascus</italic> sp., <italic>Aulosaccus</italic> cf. <italic>mitsukuri</italic>, <italic>Euplectella</italic> sp., <italic>Farrea</italic> sp., <italic>Heterochone</italic> sp., <italic>Hyalonema</italic> sp., <italic>Ipheteon panicea</italic>, <italic>Staurocalyptus</italic> sp., <italic>Sympagella nux</italic></td>
<td align="left" valign="top">Marine sponges, Hexactinellida</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b36-marinedrugs-08-02569">36</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9,25-30:3</td>
<td align="left" valign="top"><italic>Hyalonema</italic> sp.</td>
<td align="left" valign="top">Marine sponges, Hexactinellida</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b36-marinedrugs-08-02569">36</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9-31:2</td>
<td align="left" valign="top"><italic>Hyalonema</italic> sp.</td>
<td align="left" valign="top">Marine sponge, Hexactinellida</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b36-marinedrugs-08-02569">36</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9,21-31:3</td>
<td align="left" valign="top"><italic>Staurocalyptus</italic> sp.</td>
<td align="left" valign="top">Marine sponge, Hexactinellida</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b36-marinedrugs-08-02569">36</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9,22-31:3</td>
<td align="left" valign="top"><italic>Acanthascus</italic> sp., <italic>Aulosaccus</italic> cf. <italic>mitsukuri</italic>,</td>
<td align="left" valign="top">Marine sponges, Hexactinellida</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b36-marinedrugs-08-02569">36</xref>]</td></tr>
<tr>
<td colspan="4" align="left" valign="top"><hr/></td></tr>
<tr>
<td align="left" valign="top">5,9,23-32:3</td>
<td align="left" valign="top"><italic>Ipheteon panicea</italic>, <italic>Staurocalyptus</italic> sp.</td>
<td align="left" valign="top">Marine sponges, Hexactinellida</td>
<td align="left" valign="top">[<xref ref-type="bibr" rid="b36-marinedrugs-08-02569">36</xref>]</td></tr></tbody></table>
<table-wrap-foot><fn id="tfn1-marinedrugs-08-02569">
<label>*</label>
<p> According to Christie’s definition.</p></fn></table-wrap-foot></table-wrap></sec></back></article>
