Dereplication by High-Performance Liquid Chromatography (HPLC) with Quadrupole-Time-of-Flight Mass Spectroscopy (qTOF-MS) and Antiviral Activities of Phlorotannins from Ecklonia cava
Identifieur interne : 000077 ( Pmc/Checkpoint ); précédent : 000076; suivant : 000078Dereplication by High-Performance Liquid Chromatography (HPLC) with Quadrupole-Time-of-Flight Mass Spectroscopy (qTOF-MS) and Antiviral Activities of Phlorotannins from Ecklonia cava
Auteurs : Hyo Moon Cho ; Thi Phuong Doan ; Thi Kim Quy Ha ; Hyun Woo Kim ; Ba Wool Lee ; Ha Thanh Tung Pham ; Tae Oh Cho ; Won Keun OhSource :
- Marine Drugs [ 1660-3397 ] ; 2019.
Abstract
Url:
DOI: 10.3390/md17030149
PubMed: 30836593
PubMed Central: 6471242
Affiliations:
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Dereplication by High-Performance Liquid Chromatography (HPLC) with Quadrupole-Time-of-Flight Mass Spectroscopy (qTOF-MS) and Antiviral Activities of Phlorotannins from <italic>Ecklonia cava</italic></title><author><name sortKey="Cho, Hyo Moon" sort="Cho, Hyo Moon" uniqKey="Cho H" first="Hyo Moon" last="Cho">Hyo Moon Cho</name><affiliation><nlm:aff id="af1-marinedrugs-17-00149">Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Korea;<email>chgyans@naver.com</email> (H.M.C.);<email>phuongdoan@snu.ac.kr</email> (T.P.D.);<email>htkquy@ctu.edu.vn</email> (T.K.Q.H.);<email>kimkami2@snu.ac.kr</email> (H.W.K.);<email>paul36@snu.ac.kr</email> (B.W.L.);<email>thtungdl@gmail.com</email> (H.T.T.P.)</nlm:aff></affiliation></author><author><name sortKey="Doan, Thi Phuong" sort="Doan, Thi Phuong" uniqKey="Doan T" first="Thi Phuong" last="Doan">Thi Phuong Doan</name><affiliation><nlm:aff id="af1-marinedrugs-17-00149">Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Korea;<email>chgyans@naver.com</email> (H.M.C.);<email>phuongdoan@snu.ac.kr</email> (T.P.D.);<email>htkquy@ctu.edu.vn</email> (T.K.Q.H.);<email>kimkami2@snu.ac.kr</email> (H.W.K.);<email>paul36@snu.ac.kr</email> (B.W.L.);<email>thtungdl@gmail.com</email> (H.T.T.P.)</nlm:aff></affiliation></author><author><name sortKey="Ha, Thi Kim Quy" sort="Ha, Thi Kim Quy" uniqKey="Ha T" first="Thi Kim Quy" last="Ha">Thi Kim Quy Ha</name><affiliation><nlm:aff id="af1-marinedrugs-17-00149">Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Korea;<email>chgyans@naver.com</email> (H.M.C.);<email>phuongdoan@snu.ac.kr</email> (T.P.D.);<email>htkquy@ctu.edu.vn</email> (T.K.Q.H.);<email>kimkami2@snu.ac.kr</email> (H.W.K.);<email>paul36@snu.ac.kr</email> (B.W.L.);<email>thtungdl@gmail.com</email> (H.T.T.P.)</nlm:aff></affiliation></author><author><name sortKey="Kim, Hyun Woo" sort="Kim, Hyun Woo" uniqKey="Kim H" first="Hyun Woo" last="Kim">Hyun Woo Kim</name><affiliation><nlm:aff id="af1-marinedrugs-17-00149">Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Korea;<email>chgyans@naver.com</email> (H.M.C.);<email>phuongdoan@snu.ac.kr</email> (T.P.D.);<email>htkquy@ctu.edu.vn</email> (T.K.Q.H.);<email>kimkami2@snu.ac.kr</email> (H.W.K.);<email>paul36@snu.ac.kr</email> (B.W.L.);<email>thtungdl@gmail.com</email> (H.T.T.P.)</nlm:aff></affiliation></author><author><name sortKey="Lee, Ba Wool" sort="Lee, Ba Wool" uniqKey="Lee B" first="Ba Wool" last="Lee">Ba Wool Lee</name><affiliation><nlm:aff id="af1-marinedrugs-17-00149">Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Korea;<email>chgyans@naver.com</email> (H.M.C.);<email>phuongdoan@snu.ac.kr</email> (T.P.D.);<email>htkquy@ctu.edu.vn</email> (T.K.Q.H.);<email>kimkami2@snu.ac.kr</email> (H.W.K.);<email>paul36@snu.ac.kr</email> (B.W.L.);<email>thtungdl@gmail.com</email> (H.T.T.P.)</nlm:aff></affiliation></author><author><name sortKey="Pham, Ha Thanh Tung" sort="Pham, Ha Thanh Tung" uniqKey="Pham H" first="Ha Thanh Tung" last="Pham">Ha Thanh Tung Pham</name><affiliation><nlm:aff id="af1-marinedrugs-17-00149">Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Korea;<email>chgyans@naver.com</email> (H.M.C.);<email>phuongdoan@snu.ac.kr</email> (T.P.D.);<email>htkquy@ctu.edu.vn</email> (T.K.Q.H.);<email>kimkami2@snu.ac.kr</email> (H.W.K.);<email>paul36@snu.ac.kr</email> (B.W.L.);<email>thtungdl@gmail.com</email> (H.T.T.P.)</nlm:aff></affiliation></author><author><name sortKey="Cho, Tae Oh" sort="Cho, Tae Oh" uniqKey="Cho T" first="Tae Oh" last="Cho">Tae Oh Cho</name><affiliation><nlm:aff id="af2-marinedrugs-17-00149">Marine Bio Research Center, Department of Life Science, Chosun University, Gwangju 501-759, Korea;<email>tocho@chosun.ac.kr</email></nlm:aff></affiliation></author><author><name sortKey="Oh, Won Keun" sort="Oh, Won Keun" uniqKey="Oh W" first="Won Keun" last="Oh">Won Keun Oh</name><affiliation><nlm:aff id="af1-marinedrugs-17-00149">Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Korea;<email>chgyans@naver.com</email> (H.M.C.);<email>phuongdoan@snu.ac.kr</email> (T.P.D.);<email>htkquy@ctu.edu.vn</email> (T.K.Q.H.);<email>kimkami2@snu.ac.kr</email> (H.W.K.);<email>paul36@snu.ac.kr</email> (B.W.L.);<email>thtungdl@gmail.com</email> (H.T.T.P.)</nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">30836593</idno><idno type="pmc">6471242</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6471242</idno><idno type="RBID">PMC:6471242</idno><idno type="doi">10.3390/md17030149</idno><date when="2019">2019</date><idno type="wicri:Area/Pmc/Corpus">000A24</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000A24</idno><idno type="wicri:Area/Pmc/Curation">000A24</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000A24</idno><idno type="wicri:Area/Pmc/Checkpoint">000077</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Checkpoint">000077</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Dereplication by High-Performance Liquid Chromatography (HPLC) with Quadrupole-Time-of-Flight Mass Spectroscopy (qTOF-MS) and Antiviral Activities of Phlorotannins from <italic>Ecklonia cava</italic></title><author><name sortKey="Cho, Hyo Moon" sort="Cho, Hyo Moon" uniqKey="Cho H" first="Hyo Moon" last="Cho">Hyo Moon Cho</name><affiliation><nlm:aff id="af1-marinedrugs-17-00149">Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Korea;<email>chgyans@naver.com</email> (H.M.C.);<email>phuongdoan@snu.ac.kr</email> (T.P.D.);<email>htkquy@ctu.edu.vn</email> (T.K.Q.H.);<email>kimkami2@snu.ac.kr</email> (H.W.K.);<email>paul36@snu.ac.kr</email> (B.W.L.);<email>thtungdl@gmail.com</email> (H.T.T.P.)</nlm:aff></affiliation></author><author><name sortKey="Doan, Thi Phuong" sort="Doan, Thi Phuong" uniqKey="Doan T" first="Thi Phuong" last="Doan">Thi Phuong Doan</name><affiliation><nlm:aff id="af1-marinedrugs-17-00149">Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Korea;<email>chgyans@naver.com</email> (H.M.C.);<email>phuongdoan@snu.ac.kr</email> (T.P.D.);<email>htkquy@ctu.edu.vn</email> (T.K.Q.H.);<email>kimkami2@snu.ac.kr</email> (H.W.K.);<email>paul36@snu.ac.kr</email> (B.W.L.);<email>thtungdl@gmail.com</email> (H.T.T.P.)</nlm:aff></affiliation></author><author><name sortKey="Ha, Thi Kim Quy" sort="Ha, Thi Kim Quy" uniqKey="Ha T" first="Thi Kim Quy" last="Ha">Thi Kim Quy Ha</name><affiliation><nlm:aff id="af1-marinedrugs-17-00149">Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Korea;<email>chgyans@naver.com</email> (H.M.C.);<email>phuongdoan@snu.ac.kr</email> (T.P.D.);<email>htkquy@ctu.edu.vn</email> (T.K.Q.H.);<email>kimkami2@snu.ac.kr</email> (H.W.K.);<email>paul36@snu.ac.kr</email> (B.W.L.);<email>thtungdl@gmail.com</email> (H.T.T.P.)</nlm:aff></affiliation></author><author><name sortKey="Kim, Hyun Woo" sort="Kim, Hyun Woo" uniqKey="Kim H" first="Hyun Woo" last="Kim">Hyun Woo Kim</name><affiliation><nlm:aff id="af1-marinedrugs-17-00149">Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Korea;<email>chgyans@naver.com</email> (H.M.C.);<email>phuongdoan@snu.ac.kr</email> (T.P.D.);<email>htkquy@ctu.edu.vn</email> (T.K.Q.H.);<email>kimkami2@snu.ac.kr</email> (H.W.K.);<email>paul36@snu.ac.kr</email> (B.W.L.);<email>thtungdl@gmail.com</email> (H.T.T.P.)</nlm:aff></affiliation></author><author><name sortKey="Lee, Ba Wool" sort="Lee, Ba Wool" uniqKey="Lee B" first="Ba Wool" last="Lee">Ba Wool Lee</name><affiliation><nlm:aff id="af1-marinedrugs-17-00149">Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Korea;<email>chgyans@naver.com</email> (H.M.C.);<email>phuongdoan@snu.ac.kr</email> (T.P.D.);<email>htkquy@ctu.edu.vn</email> (T.K.Q.H.);<email>kimkami2@snu.ac.kr</email> (H.W.K.);<email>paul36@snu.ac.kr</email> (B.W.L.);<email>thtungdl@gmail.com</email> (H.T.T.P.)</nlm:aff></affiliation></author><author><name sortKey="Pham, Ha Thanh Tung" sort="Pham, Ha Thanh Tung" uniqKey="Pham H" first="Ha Thanh Tung" last="Pham">Ha Thanh Tung Pham</name><affiliation><nlm:aff id="af1-marinedrugs-17-00149">Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Korea;<email>chgyans@naver.com</email> (H.M.C.);<email>phuongdoan@snu.ac.kr</email> (T.P.D.);<email>htkquy@ctu.edu.vn</email> (T.K.Q.H.);<email>kimkami2@snu.ac.kr</email> (H.W.K.);<email>paul36@snu.ac.kr</email> (B.W.L.);<email>thtungdl@gmail.com</email> (H.T.T.P.)</nlm:aff></affiliation></author><author><name sortKey="Cho, Tae Oh" sort="Cho, Tae Oh" uniqKey="Cho T" first="Tae Oh" last="Cho">Tae Oh Cho</name><affiliation><nlm:aff id="af2-marinedrugs-17-00149">Marine Bio Research Center, Department of Life Science, Chosun University, Gwangju 501-759, Korea;<email>tocho@chosun.ac.kr</email></nlm:aff></affiliation></author><author><name sortKey="Oh, Won Keun" sort="Oh, Won Keun" uniqKey="Oh W" first="Won Keun" last="Oh">Won Keun Oh</name><affiliation><nlm:aff id="af1-marinedrugs-17-00149">Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Korea;<email>chgyans@naver.com</email> (H.M.C.);<email>phuongdoan@snu.ac.kr</email> (T.P.D.);<email>htkquy@ctu.edu.vn</email> (T.K.Q.H.);<email>kimkami2@snu.ac.kr</email> (H.W.K.);<email>paul36@snu.ac.kr</email> (B.W.L.);<email>thtungdl@gmail.com</email> (H.T.T.P.)</nlm:aff></affiliation></author></analytic><series><title level="j">Marine Drugs</title><idno type="eISSN">1660-3397</idno><imprint><date when="2019">2019</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p><italic>Ecklonia cava</italic> is edible seaweed that is found in Asian countries, such as Japan and Korea; and, its major components include fucoidan and phlorotannins. Phlorotannins that are isolated from <italic>E. cava</italic> are well-known to have an antioxidant effect and strong antiviral activity against porcine epidemic diarrhea virus (PEDV), which has a high mortality rate in piglets. In this study, the bioactive components were determined based on two different approaches: (i) bio-guided isolation using the antiviral activity against the H1N1 viral strain, which is a representative influenza virus that originates from swine and (ii) high-resolution mass spectrometry-based dereplication, including relative mass defects (RMDs) and HPLC-qTOFMS fragmentation analysis. The EC70 fraction showed the strongest antiviral activity and contained thirteen phlorotannins, which were predicted by dereplication. Ten compounds were directly isolated from <italic>E. cava</italic> extract and then identified. Moreover, the dereplication method allowed for the discovery of two new phlorotannins. The structures of these two isolated compounds were elucidated using NMR techniques and HPLC-qTOFMS fragmentation analysis. In addition, molecular modelling was applied to determine the absolute configurations of the two new compounds. The antiviral activities of seven major phlorotannins in active fraction were evaluated against two influenza A viral strains (H1N1 and H9N2). Six of the compounds showed moderate to strong effects on both of the viruses and phlorofucofuroeckol A (<bold>12</bold>), which showed an EC<sub>50</sub> value of 13.48 ± 1.93 μM, is a potential active antiviral component of <italic>E. cava</italic>.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Park, J Y" uniqKey="Park J">J.Y. Park</name></author><author><name sortKey="Kim, J H" uniqKey="Kim J">J.H. Kim</name></author><author><name sortKey="Kwon, J M" uniqKey="Kwon J">J.M. Kwon</name></author><author><name sortKey="Kwon, H J" uniqKey="Kwon H">H.J. 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<front><journal-meta><journal-id journal-id-type="nlm-ta">Mar Drugs</journal-id><journal-id journal-id-type="iso-abbrev">Mar Drugs</journal-id><journal-id journal-id-type="publisher-id">marinedrugs</journal-id><journal-title-group><journal-title>Marine Drugs</journal-title></journal-title-group><issn pub-type="epub">1660-3397</issn><publisher><publisher-name>MDPI</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">30836593</article-id><article-id pub-id-type="pmc">6471242</article-id><article-id pub-id-type="doi">10.3390/md17030149</article-id><article-id pub-id-type="publisher-id">marinedrugs-17-00149</article-id><article-categories><subj-group subj-group-type="heading"><subject>Article</subject></subj-group></article-categories><title-group><article-title>Dereplication by High-Performance Liquid Chromatography (HPLC) with Quadrupole-Time-of-Flight Mass Spectroscopy (qTOF-MS) and Antiviral Activities of Phlorotannins from <italic>Ecklonia cava</italic></article-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Cho</surname><given-names>Hyo Moon</given-names></name><xref ref-type="aff" rid="af1-marinedrugs-17-00149">1</xref><xref ref-type="author-notes" rid="fn1-marinedrugs-17-00149">†</xref></contrib><contrib contrib-type="author"><name><surname>Doan</surname><given-names>Thi Phuong</given-names></name><xref ref-type="aff" rid="af1-marinedrugs-17-00149">1</xref><xref ref-type="author-notes" rid="fn1-marinedrugs-17-00149">†</xref></contrib><contrib contrib-type="author"><name><surname>Ha</surname><given-names>Thi Kim Quy</given-names></name><xref ref-type="aff" rid="af1-marinedrugs-17-00149">1</xref></contrib><contrib contrib-type="author"><name><surname>Kim</surname><given-names>Hyun Woo</given-names></name><xref ref-type="aff" rid="af1-marinedrugs-17-00149">1</xref></contrib><contrib contrib-type="author"><name><surname>Lee</surname><given-names>Ba Wool</given-names></name><xref ref-type="aff" rid="af1-marinedrugs-17-00149">1</xref></contrib><contrib contrib-type="author"><name><surname>Pham</surname><given-names>Ha Thanh Tung</given-names></name><xref ref-type="aff" rid="af1-marinedrugs-17-00149">1</xref></contrib><contrib contrib-type="author"><name><surname>Cho</surname><given-names>Tae Oh</given-names></name><xref ref-type="aff" rid="af2-marinedrugs-17-00149">2</xref></contrib><contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0003-0761-3064</contrib-id><name><surname>Oh</surname><given-names>Won Keun</given-names></name><xref ref-type="aff" rid="af1-marinedrugs-17-00149">1</xref><xref rid="c1-marinedrugs-17-00149" ref-type="corresp">*</xref></contrib></contrib-group><aff id="af1-marinedrugs-17-00149"><label>1</label>Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Korea;<email>chgyans@naver.com</email> (H.M.C.);<email>phuongdoan@snu.ac.kr</email> (T.P.D.);<email>htkquy@ctu.edu.vn</email> (T.K.Q.H.);<email>kimkami2@snu.ac.kr</email> (H.W.K.);<email>paul36@snu.ac.kr</email> (B.W.L.);<email>thtungdl@gmail.com</email> (H.T.T.P.)</aff><aff id="af2-marinedrugs-17-00149"><label>2</label>Marine Bio Research Center, Department of Life Science, Chosun University, Gwangju 501-759, Korea;<email>tocho@chosun.ac.kr</email></aff><author-notes><corresp id="c1-marinedrugs-17-00149"><label>*</label>Correspondence: <email>wkoh1@snu.ac.kr</email>; Tel.: +82-02-880-7872</corresp><fn id="fn1-marinedrugs-17-00149"><label>†</label><p>These authors contributed equally.</p></fn></author-notes><pub-date pub-type="epub"><day>04</day><month>3</month><year>2019</year></pub-date><pub-date pub-type="collection"><month>3</month><year>2019</year></pub-date><volume>17</volume><issue>3</issue><elocation-id>149</elocation-id><history><date date-type="received"><day>31</day><month>1</month><year>2019</year></date><date date-type="accepted"><day>26</day><month>2</month><year>2019</year></date></history><permissions><copyright-statement>© 2019 by the authors.</copyright-statement><copyright-year>2019</copyright-year><license license-type="open-access"><license-p>Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (<ext-link ext-link-type="uri" xlink:href="http://creativecommons.org/licenses/by/4.0/">http://creativecommons.org/licenses/by/4.0/</ext-link>).</license-p></license></permissions><abstract><p><italic>Ecklonia cava</italic> is edible seaweed that is found in Asian countries, such as Japan and Korea; and, its major components include fucoidan and phlorotannins. Phlorotannins that are isolated from <italic>E. cava</italic> are well-known to have an antioxidant effect and strong antiviral activity against porcine epidemic diarrhea virus (PEDV), which has a high mortality rate in piglets. In this study, the bioactive components were determined based on two different approaches: (i) bio-guided isolation using the antiviral activity against the H1N1 viral strain, which is a representative influenza virus that originates from swine and (ii) high-resolution mass spectrometry-based dereplication, including relative mass defects (RMDs) and HPLC-qTOFMS fragmentation analysis. The EC70 fraction showed the strongest antiviral activity and contained thirteen phlorotannins, which were predicted by dereplication. Ten compounds were directly isolated from <italic>E. cava</italic> extract and then identified. Moreover, the dereplication method allowed for the discovery of two new phlorotannins. The structures of these two isolated compounds were elucidated using NMR techniques and HPLC-qTOFMS fragmentation analysis. In addition, molecular modelling was applied to determine the absolute configurations of the two new compounds. The antiviral activities of seven major phlorotannins in active fraction were evaluated against two influenza A viral strains (H1N1 and H9N2). Six of the compounds showed moderate to strong effects on both of the viruses and phlorofucofuroeckol A (<bold>12</bold>), which showed an EC<sub>50</sub> value of 13.48 ± 1.93 μM, is a potential active antiviral component of <italic>E. cava</italic>.</p></abstract><kwd-group><kwd><italic>Ecklonia cava</italic></kwd><kwd>bioactivity-guided isolation</kwd><kwd>dereplication</kwd><kwd>relative mass defect</kwd><kwd>HPLC-qTOFMS</kwd><kwd>antiviral</kwd><kwd>phlorotannins</kwd></kwd-group></article-meta></front><floats-group><fig id="marinedrugs-17-00149-f001" orientation="portrait" position="float"><label>Figure 1</label><caption><p>Cytopathic effect (CPE) inhibition assay to determine the antiviral activities of the 80% methanol extract of <italic>E. cava</italic> at 10 µg/mL (<bold>A</bold>) and five fractions (separated from the total extract with an open HP-20 column) (<bold>B</bold>) against the H1N1 A/PR/8/34 virus. In addition, the antiviral effects of compounds <bold>6</bold>, <bold>10</bold>, <bold>11</bold>, <bold>12</bold>, <bold>13</bold>, <bold>14</bold>, and <bold>16</bold> against H1N1 A/PR/8/34 virus (<bold>C</bold>) and H9N2 A/chicken/Korea/01210/2001 virus (<bold>D</bold>). Madin–Darby canine kidney (MDCK) cells were infected with the influenza viruses for 2 h and then treated with the test compounds or ribavirin (10 µM) as a positive control. The percentage of cell survival was evaluated after three days of incubation using a CPE inhibition assay. Data are expressed as the mean ± SD (<italic>n</italic> = 3), * <italic>p</italic> < 0.05, ** <italic>p</italic> < 0.01, and *** <italic>p</italic> < 0.001 as compared to the virus control group.</p></caption><graphic xlink:href="marinedrugs-17-00149-g001"></graphic></fig><fig id="marinedrugs-17-00149-f002" orientation="portrait" position="float"><label>Figure 2</label><caption><p>Identified phlorotannins and other compounds predicted by dereplication with high-resolution mass spectrometry and relative mass defect (RMD) values based on in-house and online databases. MassHunter software was used in this prediction.</p></caption><graphic xlink:href="marinedrugs-17-00149-g002"></graphic></fig><fig id="marinedrugs-17-00149-f003" orientation="portrait" position="float"><label>Figure 3</label><caption><p>(<bold>A</bold>) The inhibitory effects of compounds <bold>11</bold>, <bold>12</bold>, <bold>13,</bold> and <bold>14</bold> on viral protein synthesis. (<bold>B</bold>) The concentration-dependent inhibitory effect of compound <bold>1</bold><bold>2</bold> on viral protein synthesis. MDCK cells were infected with influenza H1N1 virus for 2 h and then treated with the test compounds or ribavirin (20 µM) as a positive control for 24 h. Western blotting was performed with β-actin as an internal control and specific antibodies (neuraminidase and hemagglutinin). The data are presented as the mean ± SD (<italic>n</italic> = 2–3), * <italic>p</italic> < 0.05, ** <italic>p</italic> < 0.01, *** <italic>p</italic> < 0.001 and <sup>#</sup><italic>p</italic> < 0.05, <sup>##</sup><italic>p</italic> < 0.01, <sup>###</sup><italic>p</italic> < 0.001 when compared to the neuraminidase and hemagglutinin virus control groups, respectively. (<bold>C</bold>) Compound <bold>1</bold><bold>2</bold> decreased neuraminidase protein expression in viral-infected cell cytoplasm at various concentrations (10, 20, and 40 µM). The fluorescence images were determined by immunocytochemistry using a fluorescence microscope.</p></caption><graphic xlink:href="marinedrugs-17-00149-g003"></graphic></fig><fig id="marinedrugs-17-00149-f004" orientation="portrait" position="float"><label>Figure 4</label><caption><p>Base peak chromatograms of the high-performance liquid chromatography—quadrupole time-of-flight mass (HPLC-qTOFMS) spectra of the EC30 (<bold>A</bold>) and EC70 (<bold>B</bold>–<bold>E</bold>) fractions of <italic>E. cava</italic> in negative ionization mode at a collision energy of 50 eV. The chromatograms were generated using MassHunter software. Full scan, high-resolution mass spectrometry screening (<bold>C</bold>,<bold>E</bold>); MS/MS identification using an in-house library of the <italic>Ecklonia</italic> genus with different collision energies from 20 to 80 eV (<bold>B</bold>,<bold>D</bold>).</p></caption><graphic xlink:href="marinedrugs-17-00149-g004"></graphic></fig><table-wrap id="marinedrugs-17-00149-t001" orientation="portrait" position="float"><object-id pub-id-type="pii">marinedrugs-17-00149-t001_Table 1</object-id><label>Table 1</label><caption><p>MS/MS fragmentation of the peaks detected in the total ion chromatograms of the EC30 and EC70 fractions of <italic>E. cava</italic> in negative ionization mode.</p></caption><table frame="hsides" rules="groups"><thead><tr><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">No</th><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">Compound Name</th><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">RT (min)</th><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">MS <sup>1</sup></th><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">MS <sup>2</sup></th><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">[M − H]<sup>−</sup></th><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">Chemical Formula</th><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">Calcd. Mass</th><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">Dif.</th><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">RMD</th></tr></thead><tbody><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>1</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Compound <bold>1</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">21.793</td><td align="center" valign="middle" rowspan="1" colspan="1">195, 247, 389, 479, 583, 743</td><td align="center" valign="middle" rowspan="1" colspan="1">139, 231, 285, 353, 447, 493, 643, 743</td><td align="center" valign="middle" rowspan="1" colspan="1">743.0881</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>36</sub>H<sub>23</sub>O<sub>18</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">743.0884</td><td align="center" valign="middle" rowspan="1" colspan="1">−1.73</td><td align="center" valign="middle" rowspan="1" colspan="1">119</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>2</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Compound <bold>2</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">25.279</td><td align="center" valign="middle" rowspan="1" colspan="1">195, 359, 479, 556, 663, 982, 1113</td><td align="center" valign="middle" rowspan="1" colspan="1">231, 353, 461, 705, 925, 1104, 1113</td><td align="center" valign="middle" rowspan="1" colspan="1">1113.1146</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>54</sub>H<sub>33</sub>O<sub>27</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">1113.1209</td><td align="center" valign="middle" rowspan="1" colspan="1">−7.94</td><td align="center" valign="middle" rowspan="1" colspan="1">103</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>3</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Benzo[1,2-b:3,4-b′]bis[1,4] benzodioxin-1,3,6,9,11-pentol</td><td align="center" valign="middle" rowspan="1" colspan="1">24.015</td><td align="center" valign="middle" rowspan="1" colspan="1">195, 211, 246, 292, 369</td><td align="center" valign="middle" rowspan="1" colspan="1">193, 230, 267, 285, 310, 369</td><td align="center" valign="middle" rowspan="1" colspan="1">369.0224</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>18</sub>H<sub>9</sub>O<sub>9</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">369.0247</td><td align="center" valign="middle" rowspan="1" colspan="1">−4.80</td><td align="center" valign="middle" rowspan="1" colspan="1">61</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>4</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Unknown</td><td align="center" valign="middle" rowspan="1" colspan="1">2.268</td><td align="center" valign="middle" rowspan="1" colspan="1">162, 197</td><td align="center" valign="middle" rowspan="1" colspan="1">163, 821</td><td align="center" valign="middle" rowspan="1" colspan="1">162.8392</td><td align="center" valign="middle" rowspan="1" colspan="1">-</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1">5154</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>5</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Unknown</td><td align="center" valign="middle" rowspan="1" colspan="1">2.631</td><td align="center" valign="middle" rowspan="1" colspan="1">122, 139, 168, 195</td><td align="center" valign="middle" rowspan="1" colspan="1">111, 139, 171 </td><td align="center" valign="middle" rowspan="1" colspan="1">195.9504</td><td align="center" valign="middle" rowspan="1" colspan="1">-</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1">4850</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>6</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Eckol</td><td align="center" valign="middle" rowspan="1" colspan="1">15.543</td><td align="center" valign="middle" rowspan="1" colspan="1">154, 371</td><td align="center" valign="middle" rowspan="1" colspan="1">217, 246, 282, 371</td><td align="center" valign="middle" rowspan="1" colspan="1">371.0446</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>18</sub>H<sub>11</sub>O<sub>9</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">371.0403</td><td align="center" valign="middle" rowspan="1" colspan="1">6.56</td><td align="center" valign="middle" rowspan="1" colspan="1">120</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>7</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">7-Phloroeckol</td><td align="center" valign="middle" rowspan="1" colspan="1">15.845</td><td align="center" valign="middle" rowspan="1" colspan="1">154, 495</td><td align="center" valign="middle" rowspan="1" colspan="1">263, 297, 387, 488, 495, 616</td><td align="center" valign="middle" rowspan="1" colspan="1">495.0511</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>24</sub>H<sub>15</sub>O<sub>12</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">495.0564</td><td align="center" valign="middle" rowspan="1" colspan="1">−7.28</td><td align="center" valign="middle" rowspan="1" colspan="1">103</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>8</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">2-Phloroeckol</td><td align="center" valign="middle" rowspan="1" colspan="1">16.003</td><td align="center" valign="middle" rowspan="1" colspan="1">154, 263, 495</td><td align="center" valign="middle" rowspan="1" colspan="1">201, 229, 283, 346, 495</td><td align="center" valign="middle" rowspan="1" colspan="1">495.0528</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>24</sub>H<sub>15</sub>O<sub>12</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">495.0564</td><td align="center" valign="middle" rowspan="1" colspan="1">−6.00</td><td align="center" valign="middle" rowspan="1" colspan="1">107</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>9</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Dibenzo[b,e][1,4]dioxin-1,2,4,7,9-pentol</td><td align="center" valign="middle" rowspan="1" colspan="1">16.209</td><td align="center" valign="middle" rowspan="1" colspan="1">137, 155, 263</td><td align="center" valign="middle" rowspan="1" colspan="1">207, 218, 263</td><td align="center" valign="middle" rowspan="1" colspan="1">263.0157</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>12</sub>H<sub>7</sub>O<sub>7</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">263.0192</td><td align="center" valign="middle" rowspan="1" colspan="1">−5.92</td><td align="center" valign="middle" rowspan="1" colspan="1">60</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>10</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">6,6′-Bieckol</td><td align="center" valign="middle" rowspan="1" colspan="1">18.854</td><td align="center" valign="middle" rowspan="1" colspan="1">154, 741</td><td align="center" valign="middle" rowspan="1" colspan="1">229, 261, 371, 479, 585, 666, 741</td><td align="center" valign="middle" rowspan="1" colspan="1">741.0647</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>36</sub>H<sub>21</sub>O<sub>18</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">741.0728</td><td align="center" valign="middle" rowspan="1" colspan="1">−9.00</td><td align="center" valign="middle" rowspan="1" colspan="1">87</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>13</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Dibenzo[1,4]dioxine-2,4,7,9-tetraol</td><td align="center" valign="middle" rowspan="1" colspan="1">19.274</td><td align="center" valign="middle" rowspan="1" colspan="1">123, 155, 247</td><td align="center" valign="middle" rowspan="1" colspan="1">141, 195, 247, 385, 479</td><td align="center" valign="middle" rowspan="1" colspan="1">247.0243</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>12</sub>H<sub>7</sub>O<sub>6</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">247.0243</td><td align="center" valign="middle" rowspan="1" colspan="1">0.00</td><td align="center" valign="middle" rowspan="1" colspan="1">98</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>15</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">6,8′-Bieckol</td><td align="center" valign="middle" rowspan="1" colspan="1">19.569</td><td align="center" valign="middle" rowspan="1" colspan="1">741</td><td align="center" valign="middle" rowspan="1" colspan="1">260, 371, 479, 615, 741</td><td align="center" valign="middle" rowspan="1" colspan="1">741.0737</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>36</sub>H<sub>21</sub>O<sub>18</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">741.0728</td><td align="center" valign="middle" rowspan="1" colspan="1">3.00</td><td align="center" valign="middle" rowspan="1" colspan="1">99</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>11</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Dieckol</td><td align="center" valign="middle" rowspan="1" colspan="1">19.917</td><td align="center" valign="middle" rowspan="1" colspan="1">321, 741</td><td align="center" valign="middle" rowspan="1" colspan="1">229, 261, 371, 430, 545, 714, 741</td><td align="center" valign="middle" rowspan="1" colspan="1">741.0723</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>36</sub>H<sub>21</sub>O<sub>18</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">741.0728</td><td align="center" valign="middle" rowspan="1" colspan="1">−2.24</td><td align="center" valign="middle" rowspan="1" colspan="1">98</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>14</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Dioxinodehydroeckol</td><td align="center" valign="middle" rowspan="1" colspan="1">20.370</td><td align="center" valign="middle" rowspan="1" colspan="1">123, 196, 325, 369</td><td align="center" valign="middle" rowspan="1" colspan="1">123, 161, 173, 199, 261, 369</td><td align="center" valign="middle" rowspan="1" colspan="1">369.0269</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>18</sub>H<sub>9</sub>O<sub>9</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">369.0247</td><td align="center" valign="middle" rowspan="1" colspan="1">4.69</td><td align="center" valign="middle" rowspan="1" colspan="1">73</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>12</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Phlorofucofuroeckol A</td><td align="center" valign="middle" rowspan="1" colspan="1">21.796</td><td align="center" valign="middle" rowspan="1" colspan="1">155, 601</td><td align="center" valign="middle" rowspan="1" colspan="1">245, 385, 447, 493, 601</td><td align="center" valign="middle" rowspan="1" colspan="1">601.0640</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>30</sub>H<sub>17</sub>O<sub>14</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">601.0618</td><td align="center" valign="middle" rowspan="1" colspan="1">4.69</td><td align="center" valign="middle" rowspan="1" colspan="1">106</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>17</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">2,7″-phloroglucinol 6,6′-bieckol (PHB)</td><td align="center" valign="middle" rowspan="1" colspan="1">22.018</td><td align="center" valign="middle" rowspan="1" colspan="1">155, 973</td><td align="center" valign="middle" rowspan="1" colspan="1">229, 353, 427, 493, 707, 806, 973</td><td align="center" valign="middle" rowspan="1" colspan="1">973.1153</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>48</sub>H<sub>29</sub>O<sub>23</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">973.1100</td><td align="center" valign="middle" rowspan="1" colspan="1">7.28</td><td align="center" valign="middle" rowspan="1" colspan="1">118</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>18</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">974-A</td><td align="center" valign="middle" rowspan="1" colspan="1">22.050</td><td align="center" valign="middle" rowspan="1" colspan="1">113, 601, 973</td><td align="center" valign="middle" rowspan="1" colspan="1">229, 353, 393, 605, 707, 805, 941</td><td align="center" valign="middle" rowspan="1" colspan="1">973.1038</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>48</sub>H<sub>29</sub>O<sub>23</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">973.1100</td><td align="center" valign="middle" rowspan="1" colspan="1">−7.87</td><td align="center" valign="middle" rowspan="1" colspan="1">107</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>19</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Unknown</td><td align="center" valign="middle" rowspan="1" colspan="1">22.44</td><td align="center" valign="middle" rowspan="1" colspan="1">155, 369, 551</td><td align="center" valign="middle" rowspan="1" colspan="1">223, 304, 551, 583, 710</td><td align="center" valign="middle" rowspan="1" colspan="1">551.1816</td><td align="center" valign="middle" rowspan="1" colspan="1">-</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1">329</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>16</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Fucofuroeckol A</td><td align="center" valign="middle" rowspan="1" colspan="1">22.897</td><td align="center" valign="middle" rowspan="1" colspan="1">155, 477,</td><td align="center" valign="middle" rowspan="1" colspan="1">2551, 352, 477, 545</td><td align="center" valign="middle" rowspan="1" colspan="1">477.0425</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>24</sub>H<sub>13</sub>O<sub>11</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">477.0457</td><td align="center" valign="middle" rowspan="1" colspan="1">−5.66</td><td align="center" valign="middle" rowspan="1" colspan="1">89</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>20</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Unknown</td><td align="center" valign="middle" rowspan="1" colspan="1">23.799</td><td align="center" valign="middle" rowspan="1" colspan="1">242, 310</td><td align="center" valign="middle" rowspan="1" colspan="1">201, 271, 348</td><td align="center" valign="middle" rowspan="1" colspan="1">242.1758</td><td align="center" valign="middle" rowspan="1" colspan="1">-</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1">726</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>21</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">6,9,12-Octadecatrienoic acid, (6Z,9Z,12Z)</td><td align="center" valign="middle" rowspan="1" colspan="1">29.966</td><td align="center" valign="middle" rowspan="1" colspan="1">277, 527</td><td align="center" valign="middle" rowspan="1" colspan="1">264, 353, 481, </td><td align="center" valign="middle" rowspan="1" colspan="1">277.2125</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>18</sub>H<sub>29</sub>O<sub>2</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">277.2168</td><td align="center" valign="middle" rowspan="1" colspan="1">−6.56</td><td align="center" valign="middle" rowspan="1" colspan="1">767</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>22</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">9,12-Octadecadienoic acid (9Z,12Z)</td><td align="center" valign="middle" rowspan="1" colspan="1">30.496</td><td align="center" valign="middle" rowspan="1" colspan="1">279</td><td align="center" valign="middle" rowspan="1" colspan="1">218, 248, 279, 346, 380</td><td align="center" valign="middle" rowspan="1" colspan="1">279.2168</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>18</sub>H<sub>31</sub>O<sub>2</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">279.2324</td><td align="center" valign="middle" rowspan="1" colspan="1">−12.49</td><td align="center" valign="middle" rowspan="1" colspan="1">776</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>23</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Ecklonialactone B (R/S)</td><td align="center" valign="middle" rowspan="1" colspan="1">32.281</td><td align="center" valign="middle" rowspan="1" colspan="1">265, 291</td><td align="center" valign="middle" rowspan="1" colspan="1">201, 291</td><td align="center" valign="middle" rowspan="1" colspan="1">291.2020</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>18</sub>H<sub>27</sub>O<sub>3</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">291.1960</td><td align="center" valign="middle" rowspan="1" colspan="1">7.75</td><td align="center" valign="middle" rowspan="1" colspan="1">694</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>24</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Eicosanoic acid</td><td align="center" valign="middle" rowspan="1" colspan="1">34.206</td><td align="center" valign="middle" rowspan="1" colspan="1">311</td><td align="center" valign="middle" rowspan="1" colspan="1">225, 311, 349</td><td align="center" valign="middle" rowspan="1" colspan="1">311.2848</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>20</sub>H<sub>39</sub>O<sub>2</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">311.2950</td><td align="center" valign="middle" rowspan="1" colspan="1">−10.10</td><td align="center" valign="middle" rowspan="1" colspan="1">915</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>25</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Ecklonialactone B (S/R)</td><td align="center" valign="middle" rowspan="1" colspan="1">34.499</td><td align="center" valign="middle" rowspan="1" colspan="1">291, 555, 623</td><td align="center" valign="middle" rowspan="1" colspan="1">251, 291, 411,651</td><td align="center" valign="middle" rowspan="1" colspan="1">291.1938</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>18</sub>H<sub>27</sub>O<sub>3</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">291.1960</td><td align="center" valign="middle" rowspan="1" colspan="1">−4.96</td><td align="center" valign="middle" rowspan="1" colspan="1">666</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>26</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">11,14,17-Eicosatrienoic acid, (11Z,14Z,17Z)-</td><td align="center" valign="middle" rowspan="1" colspan="1">34.771</td><td align="center" valign="middle" rowspan="1" colspan="1">305</td><td align="center" valign="middle" rowspan="1" colspan="1">211, 284, 305, 248, 583, 804</td><td align="center" valign="middle" rowspan="1" colspan="1">305.2410</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>20</sub>H<sub>33</sub>O<sub>2</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">305.2481</td><td align="center" valign="middle" rowspan="1" colspan="1">−8.43</td><td align="center" valign="middle" rowspan="1" colspan="1">790</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>27</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Tricosanoic acid</td><td align="center" valign="middle" rowspan="1" colspan="1">36.294</td><td align="center" valign="middle" rowspan="1" colspan="1">353</td><td align="center" valign="middle" rowspan="1" colspan="1">257, 333, 353, 529</td><td align="center" valign="middle" rowspan="1" colspan="1">353.3407</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>23</sub>H<sub>45</sub>O<sub>2</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">353.3420</td><td align="center" valign="middle" rowspan="1" colspan="1">−3.61</td><td align="center" valign="middle" rowspan="1" colspan="1">964</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>28</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Heneicosanoic acid</td><td align="center" valign="middle" rowspan="1" colspan="1">36.667</td><td align="center" valign="middle" rowspan="1" colspan="1">325</td><td align="center" valign="middle" rowspan="1" colspan="1">225, 239, 248, 267, 282, 325</td><td align="center" valign="middle" rowspan="1" colspan="1">325.3131</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>21</sub>H<sub>41</sub>O<sub>2</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">325.3107</td><td align="center" valign="middle" rowspan="1" colspan="1">4.90</td><td align="center" valign="middle" rowspan="1" colspan="1">962</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>29</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Unknown</td><td align="center" valign="middle" rowspan="1" colspan="1">37.806</td><td align="center" valign="middle" rowspan="1" colspan="1">293, 325</td><td align="center" valign="middle" rowspan="1" colspan="1">281, 325, 386, 449, 674</td><td align="center" valign="middle" rowspan="1" colspan="1">325.1812</td><td align="center" valign="middle" rowspan="1" colspan="1">-</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1">557</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>30</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Unknown</td><td align="center" valign="middle" rowspan="1" colspan="1">37.869</td><td align="center" valign="middle" rowspan="1" colspan="1">239, 293</td><td align="center" valign="middle" rowspan="1" colspan="1">207, 239, 243, 383</td><td align="center" valign="middle" rowspan="1" colspan="1">239.0709</td><td align="center" valign="middle" rowspan="1" colspan="1">-</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1">297</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>31</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Unknown</td><td align="center" valign="middle" rowspan="1" colspan="1">38.947</td><td align="center" valign="middle" rowspan="1" colspan="1">321</td><td align="center" valign="middle" rowspan="1" colspan="1">248, 321, 399, 572, 815</td><td align="center" valign="middle" rowspan="1" colspan="1">321.2178</td><td align="center" valign="middle" rowspan="1" colspan="1">-</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1">678</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>32</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Docosanoic acid</td><td align="center" valign="middle" rowspan="1" colspan="1">39.599</td><td align="center" valign="middle" rowspan="1" colspan="1">339</td><td align="center" valign="middle" rowspan="1" colspan="1">226, 339, 433, 660, 809</td><td align="center" valign="middle" rowspan="1" colspan="1">339.3292</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>22</sub>H<sub>43</sub>O<sub>2</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">339.3263</td><td align="center" valign="middle" rowspan="1" colspan="1">5.39</td><td align="center" valign="middle" rowspan="1" colspan="1">970</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>33</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Unknown</td><td align="center" valign="middle" rowspan="1" colspan="1">41.028</td><td align="center" valign="middle" rowspan="1" colspan="1">346</td><td align="center" valign="middle" rowspan="1" colspan="1">206, 254, 330, 346, 642</td><td align="center" valign="middle" rowspan="1" colspan="1">346.1092</td><td align="center" valign="middle" rowspan="1" colspan="1">-</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1">316</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>34</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Unknown</td><td align="center" valign="middle" rowspan="1" colspan="1">41.59</td><td align="center" valign="middle" rowspan="1" colspan="1">346, 485</td><td align="center" valign="middle" rowspan="1" colspan="1">280, 421, 485</td><td align="center" valign="middle" rowspan="1" colspan="1">485.2671</td><td align="center" valign="middle" rowspan="1" colspan="1">-</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1">550</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>35</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">5,8,11,14,17-Eicosapentaenoic acid, (5Z,8Z,11Z,14Z,17Z)</td><td align="center" valign="middle" rowspan="1" colspan="1">43.93</td><td align="center" valign="middle" rowspan="1" colspan="1">301, 369</td><td align="center" valign="middle" rowspan="1" colspan="1">205, 269, 301, 440</td><td align="center" valign="middle" rowspan="1" colspan="1">301.2099</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>20</sub>H<sub>29</sub>O<sub>2</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">301.2168</td><td align="center" valign="middle" rowspan="1" colspan="1">−8.31</td><td align="center" valign="middle" rowspan="1" colspan="1">697</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>36</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Triacontanoic acid</td><td align="center" valign="middle" rowspan="1" colspan="1">47.116</td><td align="center" valign="middle" rowspan="1" colspan="1">346, 451, 535, 691, 775</td><td align="center" valign="middle" rowspan="1" colspan="1">295, 387, 451, 456</td><td align="center" valign="middle" rowspan="1" colspan="1">451.4499</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>30</sub>H<sub>59</sub>O<sub>2</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">451.4515</td><td align="center" valign="middle" rowspan="1" colspan="1">−4.00</td><td align="center" valign="middle" rowspan="1" colspan="1">997</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>37</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Dotricontanoic acid</td><td align="center" valign="middle" rowspan="1" colspan="1">47.575</td><td align="center" valign="middle" rowspan="1" colspan="1">346, 479, 609, 691, 775</td><td align="center" valign="middle" rowspan="1" colspan="1">461, 479, 648, 866</td><td align="center" valign="middle" rowspan="1" colspan="1">479.2903</td><td align="center" valign="middle" rowspan="1" colspan="1">C<sub>32</sub>H<sub>63</sub>O<sub>2</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">479.4828</td><td align="center" valign="middle" rowspan="1" colspan="1">−5.00</td><td align="center" valign="middle" rowspan="1" colspan="1">606</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>38</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Unknown</td><td align="center" valign="middle" rowspan="1" colspan="1">49.963</td><td align="center" valign="middle" rowspan="1" colspan="1">223, 297, 441, 535, 701, 849</td><td align="center" valign="middle" rowspan="1" colspan="1">254, 333, 441, 673</td><td align="center" valign="middle" rowspan="1" colspan="1">441.2074</td><td align="center" valign="middle" rowspan="1" colspan="1">-</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1">470</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>39</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Unknown</td><td align="center" valign="middle" rowspan="1" colspan="1">51.118</td><td align="center" valign="middle" rowspan="1" colspan="1">149, 223</td><td align="center" valign="middle" rowspan="1" colspan="1">149, 448</td><td align="center" valign="middle" rowspan="1" colspan="1">149.0021</td><td align="center" valign="middle" rowspan="1" colspan="1">-</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1">14</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>40</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">Unknown</td><td align="center" valign="middle" rowspan="1" colspan="1">53.856</td><td align="center" valign="middle" rowspan="1" colspan="1">149, 223, 297</td><td align="center" valign="middle" rowspan="1" colspan="1">149, 221, 350, 630.7708</td><td align="center" valign="middle" rowspan="1" colspan="1">149.0086</td><td align="center" valign="middle" rowspan="1" colspan="1">-</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1">58</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>41</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Unknown</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">58.796</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">135</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">135.9698, 287.5036</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">135.9751</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">-</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">7171</td></tr></tbody></table></table-wrap></floats-group></pmc><affiliations><list></list><tree><noCountry><name sortKey="Cho, Hyo Moon" sort="Cho, Hyo Moon" uniqKey="Cho H" first="Hyo Moon" last="Cho">Hyo Moon Cho</name><name sortKey="Cho, Tae Oh" sort="Cho, Tae Oh" uniqKey="Cho T" first="Tae Oh" last="Cho">Tae Oh Cho</name><name sortKey="Doan, Thi Phuong" sort="Doan, Thi Phuong" uniqKey="Doan T" first="Thi Phuong" last="Doan">Thi Phuong Doan</name><name sortKey="Ha, Thi Kim Quy" sort="Ha, Thi Kim Quy" uniqKey="Ha T" first="Thi Kim Quy" last="Ha">Thi Kim Quy Ha</name><name sortKey="Kim, Hyun Woo" sort="Kim, Hyun Woo" uniqKey="Kim H" first="Hyun Woo" last="Kim">Hyun Woo Kim</name><name sortKey="Lee, Ba Wool" sort="Lee, Ba Wool" uniqKey="Lee B" first="Ba Wool" last="Lee">Ba Wool Lee</name><name sortKey="Oh, Won Keun" sort="Oh, Won Keun" uniqKey="Oh W" first="Won Keun" last="Oh">Won Keun Oh</name><name sortKey="Pham, Ha Thanh Tung" sort="Pham, Ha Thanh Tung" uniqKey="Pham H" first="Ha Thanh Tung" last="Pham">Ha Thanh Tung Pham</name></noCountry></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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