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 : 000099 ( Main/Exploration ); précédent : 000098; suivant : 000100Dereplication 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><idno type="wicri:Area/Ncbi/Merge">000F69</idno><idno type="wicri:Area/Ncbi/Curation">000F69</idno><idno type="wicri:Area/Ncbi/Checkpoint">000F69</idno><idno type="wicri:Area/Main/Merge">000099</idno><idno type="wicri:Area/Main/Curation">000099</idno><idno type="wicri:Area/Main/Exploration">000099</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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Lee</name></author><author><name sortKey="Kim, Y M" uniqKey="Kim Y">Y.M Kim</name></author></analytic></biblStruct></listBibl></div1></back></TEI><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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