161 lines
17 KiB
XML
161 lines
17 KiB
XML
<document id="350C99BF0135DEAB93F9EF723864BE00" ID-DOI="10.1016/j.phytochem.2021.112851" ID-ISSN="1873-3700" ID-Zenodo-Dep="8273100" IM.bibliography_approvedBy="julia" IM.illustrations_approvedBy="julia" IM.materialsCitations_approvedBy="julia" IM.metadata_approvedBy="julia" IM.tables_approvedBy="julia" IM.taxonomicNames_approvedBy="julia" IM.treatments_approvedBy="julia" checkinTime="1692302852229" checkinUser="felipe" docAuthor="Berek-Nagy, Peter Janos, Gergo Toth, Szilvia Bosze, Lilla Borbala Horvath, Andras Darcsi, Sandor Csikos, Daniel G. Knapp, Gabor M. Kovacs & Imre Boldizsar" docDate="2021" docId="162A882E3D73FF97FFD2FAD2FA8AF9C8" docLanguage="en" docName="Phytochemistry.190.112851.pdf" docOrigin="Phytochemistry (112851) 190" docSource="http://dx.doi.org/10.1016/j.phytochem.2021.112851" docStyle="DocumentStyle:F36D69FC8B198FBE91029DF9C24697D3.5:Phytochemistry.2020-.journal_article" docStyleId="F36D69FC8B198FBE91029DF9C24697D3" docStyleName="Phytochemistry.2020-.journal_article" docStyleVersion="5" docTitle="Flavomyces fulophazii" docType="treatment" docVersion="1" lastPageNumber="7" masterDocId="EA13F0563D75FF91FFB6FFAFFF9FFFAD" masterDocTitle="The grass root endophytic fungus Flavomyces fulophazii: An abundant source of tetramic acid and chlorinated azaphilone derivatives" masterLastPageNumber="11" masterPageNumber="1" pageNumber="7" updateTime="1692732117389" updateUser="julia">
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<mods:title id="09BF1E5996AE76F3F77E332948B942E2">The grass root endophytic fungus Flavomyces fulophazii: An abundant source of tetramic acid and chlorinated azaphilone derivatives</mods:title>
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<mods:namePart id="D590890FC8736E14122B50BF8181F8D8">Berek-Nagy, Peter Janos</mods:namePart>
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<mods:affiliation id="8533F8B3627D5AA8717F6EE1613F9B8D">Department of Plant Anatomy, Institute of Biology, Eotvos Lorand´University, Pazmany Peter setany 1 / C, Budapest, 1117, Hungary; National Public Health Center, Albert Fl´ori´an út 2 - 6, Budapest, 1097, Hungary</mods:affiliation>
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<mods:namePart id="2115DBBFC33E25B66EFFC5767AE232C6">Gergo Toth</mods:namePart>
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<mods:affiliation id="D068C641181D9A27B3261D808D80A747">Department of Pharmaceutical Chemistry, Semmelweis University, H ˝ ogyes Endre u. 9, Budapest, 1092, Hungary</mods:affiliation>
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<mods:name id="7093381DE667073B904C08517B9033EE" type="personal">
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<mods:namePart id="972B073BB9C0DD55B8A95C12B5EA23F3">Szilvia Bosze</mods:namePart>
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<mods:affiliation id="2B1195B7B0FA2DB80AFB5997494EE48B">National Public Health Center, Albert Fl´ori´an út 2 - 6, Budapest, 1097, Hungary; Research Group of Peptide Chemistry, Eotos Lorand University, Eotvos Lorand Research Network (ELKH), Pazmany Peter setany 1 / A, Budapest, 1117, Hungary e National Institute of Pharmacy and Nutrition, Zrínyi u. 3, Budapest, 1051, Hungary</mods:affiliation>
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<mods:namePart id="BD2AA8E7FEDA9AC0142B23DDAFC0D74A">Lilla Borbala Horvath</mods:namePart>
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<mods:affiliation id="FA1859401BDD295D618038F1898D327B">National Public Health Center, Albert Florian út 2 - 6, Budapest, 1097, Hungary; Research Group of Peptide Chemistry, Eotos Lorand University, Eotvos Lorand Research Network (ELKH), Pazmany Peter setany 1 / A, Budapest, 1117, Hungary e National Institute of Pharmacy and Nutrition, Zrínyi u. 3, Budapest, 1051, Hungary</mods:affiliation>
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<mods:namePart id="3D8D67E2138697DBC55F57BF6A455D95">Andras Darcsi</mods:namePart>
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<mods:affiliation id="30FDD8B95B0FDEE591AF2006DCD10DA6">National Institute of Pharmacy and Nutrition, Zrínyi u. 3, Budapest, 1051, Hungary</mods:affiliation>
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<mods:namePart id="43C3E0B839D654ADF1152451EDE61204">Sandor Csikos</mods:namePart>
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<mods:affiliation id="01D6DDF59C537F285DA204324848CF81">Department of Plant Anatomy, Institute of Biology, Eotvos Lorand´University, Pazmany Peter setany 1 / C, Budapest, 1117, Hungary; National Public Health Center, Albert Florian út 2 - 6, Budapest, 1097, Hungary</mods:affiliation>
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<mods:namePart id="44DCC7C0855559893E1A7BD3BBB338CF">Daniel G. Knapp</mods:namePart>
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<mods:affiliation id="4E685CDA4AB73AB5677F4BAA979672F2">Department of Plant Anatomy, Institute of Biology, Eotvos Lorand´University, Pazmany Peter setany 1 / C, Budapest, 1117, Hungary</mods:affiliation>
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</mods:name>
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<mods:name id="3BD1B98CA0E5A92FF3C1E8BC85FA9733" type="personal">
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<mods:namePart id="7494E50635BBF289D255980D8381535D">Gabor M. Kovacs</mods:namePart>
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<mods:affiliation id="CEFFE6A9BE8E517275061B917E918391">Department of Plant Anatomy, Institute of Biology, Eotvos Lorand´University, Pazmany Peter setany 1 / C, Budapest, 1117, Hungary</mods:affiliation>
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<mods:namePart id="C071B9FFED583CE827448B7439E5487A">Imre Boldizsar</mods:namePart>
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<mods:affiliation id="86204CCE3C1437EDCA568DB57C04C884">Department of Plant Anatomy, Institute of Biology, Eotvos Lorand´University, Pazmany Peter setany 1 / C, Budapest, 1117, Hungary</mods:affiliation>
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<mods:title id="ECF7D66980B335F4D77C8C255A450A9E">Phytochemistry</mods:title>
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<mods:date id="ED9B63FA311A3D16339775D533532E3D">2021</mods:date>
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<mods:title id="09800362085FFC5B1DFA7D78086AD2C7">112851</mods:title>
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<mods:number id="E09C053C21DF3CCE44EF2F3CDF87F464">2021-10-31</mods:number>
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<mods:number id="7C1F4BF9BC01EE6AC8762B4FF1E31493">190</mods:number>
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<mods:url id="8C959BA9054EB6F2F46FBD9E0A88872D">http://dx.doi.org/10.1016/j.phytochem.2021.112851</mods:url>
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<mods:identifier id="C79D45B1306D2BA328CFA016B5A007DD" type="DOI">10.1016/j.phytochem.2021.112851</mods:identifier>
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<mods:identifier id="12C90352B3F4AD95D055DCDE5F5EF305" type="ISSN">1873-3700</mods:identifier>
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<emphasis id="ACF7E52A3D73FF97FFD2FAD2FD5CFA22" bold="true" box="[100,707,1404,1424]" italics="true" pageId="6" pageNumber="7">
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2.2. Amounts of compounds in the in vitro cultures of
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<taxonomicName id="598342BB3D73FF97FDE5FAD2FD5CFA22" ID-CoL="6J9JM" authority="D.G.Knapp, Kovács, J.Z.Groenew. & Crous" box="[595,707,1404,1424]" class="Dothideomycetes" family="Lentitheciaceae" genus="Flavomyces" kingdom="Fungi" order="Pleosporales" pageId="6" pageNumber="7" phylum="Ascomycota" rank="species" species="fulophazii">F. fulophazii</taxonomicName>
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</emphasis>
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</paragraph>
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<subSubSection id="D6996AB33D73FF97FF32FA1AFA8AF9C8" pageId="6" pageNumber="7" type="description">
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<paragraph id="9E3C39383D73FF97FF32FA1AFEF9F90A" blockId="6.[100,770,1460,1982]" pageId="6" pageNumber="7">
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Amounts of all identified compounds were determined by HPLC-MS in the lyophilized cultures of ten Hungarian and seven Mongolian
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||
<taxonomicName id="598342BB3D73FF97FFD2FA42FF4DFA52" authority="D.G.Knapp, Kovács, J.Z.Groenew. & Crous" box="[100,210,1516,1536]" class="Dothideomycetes" family="Lentitheciaceae" genus="Flavomyces" kingdom="Fungi" order="Pleosporales" pageId="6" pageNumber="7" phylum="Ascomycota" rank="species" species="fulophazii">
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<emphasis id="ACF7E52A3D73FF97FFD2FA42FF4DFA52" bold="true" box="[100,210,1516,1536]" italics="true" pageId="6" pageNumber="7">F. fulophazii</emphasis>
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</taxonomicName>
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isolates grown in three replicates (Supplementary
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||
<tableCitation id="D3010C833D73FF97FD1DFA43FD61FA52" box="[683,766,1516,1535]" captionStart="Table 4" captionStartId="4.[100,150,788,804]" captionTargetPageId="4" captionText="Table 4 NMR spectroscopic data of E and Z diastereoisomers of 11-hydroxyvermelhotin (compound 2) in DMSO d6 and methanol-d4." httpUri="http://table.plazi.org/id/CAFC69B03D71FF95FFD2FCBBFB16FC93" pageId="6" pageNumber="7" tableUuid="CAFC69B03D71FF95FFD2FCBBFB16FC93">Table S4</tableCitation>
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||
, Fig. S8). Among tetramic acids and azaphilones, vermelhotin and flavochlorine A were found to be the main compounds, respectively, in all samples. The highest amounts of vermelhotin were determined in cultures of the Hungarian and Mongolian isolates HF-3 (
|
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<quantity id="597B94DD3D73FF97FDFBF9F3FD09F9C2" box="[589,662,1628,1647]" metricMagnitude="-6" metricUnit="kg" metricValue="5.3" pageId="6" pageNumber="7" unit="mg" value="5.3">5.3 mg</quantity>
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/g) and MF-7 (
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<quantity id="597B94DD3D73FF97FFCBF9D7FF55F926" box="[125,202,1656,1675]" metricMagnitude="-6" metricUnit="kg" metricValue="5.5" pageId="6" pageNumber="7" unit="mg" value="5.5">5.5 mg</quantity>
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/g), respectively (data are averages, calculated from contents of three replicate cultures).
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</paragraph>
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<paragraph id="9E3C39383D73FF97FF32F91FFC62FB57" blockId="6.[100,770,1460,1982]" lastBlockId="6.[818,1488,1004,1637]" pageId="6" pageNumber="7">
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||
In order to isolate vermelhotin by preparative HPLC, three-three lyophilized cultures of the isolate HF-3 and those of MF-7 were pooled and extracted (six cultures, in total). Since the total weight of these pooled cultures was
|
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<quantity id="597B94DD3D73FF97FE96F8ACFEFDF8BA" box="[288,354,1795,1815]" metricMagnitude="-3" metricUnit="kg" metricValue="1.09" pageId="6" pageNumber="7" unit="g" value="1.09">1.09 g</quantity>
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,
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<quantity id="597B94DD3D73FF97FEDCF8ACFE2FF8BA" box="[362,432,1795,1815]" metricMagnitude="-6" metricUnit="kg" metricValue="5.9" pageId="6" pageNumber="7" unit="mg" value="5.9">5.9 mg</quantity>
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vermelhotin could be isolated as the calculated maximum yield (CMY). The preparative HPLC isolation could be regarded to be effective, according to a comparison of the CMY of vermelhotin (
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<quantity id="597B94DD3D73FF97FF54F8F8FEB4F8C7" box="[226,299,1879,1898]" metricMagnitude="-6" metricUnit="kg" metricValue="5.9" pageId="6" pageNumber="7" unit="mg" value="5.9">5.9 mg</quantity>
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) with the amount of vermelhotin isolated from the lyophilized cultures (
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<quantity id="597B94DD3D73FF97FE86F8DCFEE0F82B" box="[304,383,1907,1926]" metricMagnitude="-6" metricUnit="kg" metricValue="4.8" pageId="6" pageNumber="7" unit="mg" value="4.8">4.8 mg</quantity>
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), thus suggesting the practical utility of
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<taxonomicName id="598342BB3D73FF97FFD2F820FF4CF80C" authority="D.G.Knapp, Kovács, J.Z.Groenew. & Crous" box="[100,211,1934,1954]" class="Dothideomycetes" family="Lentitheciaceae" genus="Flavomyces" kingdom="Fungi" order="Pleosporales" pageId="6" pageNumber="7" phylum="Ascomycota" rank="species" species="fulophazii">
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<emphasis id="ACF7E52A3D73FF97FFD2F820FF4CF80C" bold="true" box="[100,211,1934,1954]" italics="true" pageId="6" pageNumber="7">F. fulophazii</emphasis>
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</taxonomicName>
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||
in high-yield vermelhotin production. Accumulation of the vermelhotin derivatives (dihydroxyvermelhotin, hydroxyvermelhotin, methoxyvermelhotin and oxovermelhotin) showed a close correlation with that of vermelhotin, resulting in their highest amounts also in the cultures of isolates HF-3 and MF-7 (Supplementary
|
||
<tableCitation id="D3010C833D73FF97FA95FB8BFAE8FB9A" box="[1315,1399,1060,1079]" captionStart="Table 4" captionStartId="4.[100,150,788,804]" captionTargetPageId="4" captionText="Table 4 NMR spectroscopic data of E and Z diastereoisomers of 11-hydroxyvermelhotin (compound 2) in DMSO d6 and methanol-d4." httpUri="http://table.plazi.org/id/CAFC69B03D71FF95FFD2FCBBFB16FC93" pageId="6" pageNumber="7" tableUuid="CAFC69B03D71FF95FFD2FCBBFB16FC93">Table S4</tableCitation>
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||
). Among these vermelhotin derivatives, hydroxyvermelhotin was determined to be the most abundant compound, reaching its maximum levels of
|
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<quantity id="597B94DD3D73FF97FC84FBD7FCE0FB26" box="[818,895,1144,1163]" metricMagnitude="-6" metricUnit="kg" metricValue="1.1" pageId="6" pageNumber="7" unit="mg" value="1.1">1.1 mg</quantity>
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/g and 1.0 mg/g in the cultures of isolates HF-3 and MF-7, respectively (average values, calculated from contents of three parallel cultures). Accordingly, in addition to vermelhotin, hydroxyvermelhotin could also be isolated from the pooled cultures of isolates HF-3 and MF-7 by preparative HPLC.
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||
</paragraph>
|
||
<paragraph id="9E3C39383D73FF97FCE7FAACFC55F9BC" blockId="6.[818,1488,1004,1637]" pageId="6" pageNumber="7">
|
||
A relative high-level accumulation of the azaphilone flavochlorine A was detected in cultures of isolates MF-3 (MF-3B,
|
||
<quantity id="597B94DD3D73FF97FAB4FAB0FAD2FA9F" box="[1282,1357,1311,1330]" metricMagnitude="-6" metricUnit="kg" metricValue="4.2" pageId="6" pageNumber="7" unit="mg" value="4.2">4.2 mg</quantity>
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||
/g), HF-1 (HF-1A,
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||
<quantity id="597B94DD3D73FF97FCE1FA94FC3EFAE3" box="[855,929,1339,1358]" metricMagnitude="-6" metricUnit="kg" metricValue="3.1" pageId="6" pageNumber="7" unit="mg" value="3.1">3.1 mg</quantity>
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||
/g) and HF-9 (HF–9B,
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<quantity id="597B94DD3D73FF97FBC6FA94FB24FAE3" box="[1136,1211,1339,1358]" metricMagnitude="-6" metricUnit="kg" metricValue="2.2" pageId="6" pageNumber="7" unit="mg" value="2.2">2.2 mg</quantity>
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||
/g). However, flavochlorine A levels were at least one order of magnitude smaller in the corresponding parallel cultures of these isolates. Consequently, in order to isolate flavochlorine A, cultures of different isolates (detailed above), containing the highest levels of this compound, were pooled and extracted. Accumulation of azaphilones B–G, occurring as minor compounds relative to flavochlorine A, showed a close correlation with the accumulation of flavochlorine A.
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||
</paragraph>
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||
<paragraph id="9E3C39383D73FF97FCE7F9B5FA8AF9C8" blockId="6.[818,1488,1004,1637]" pageId="6" pageNumber="7">
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||
We found the metabolite production of
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||
<taxonomicName id="598342BB3D73FF97FB70F9B5FAAAF980" authority="D.G.Knapp, Kovács, J.Z.Groenew. & Crous" box="[1222,1333,1562,1581]" class="Dothideomycetes" family="Lentitheciaceae" genus="Flavomyces" kingdom="Fungi" order="Pleosporales" pageId="6" pageNumber="7" phylum="Ascomycota" rank="species" species="fulophazii">
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<emphasis id="ACF7E52A3D73FF97FB70F9B5FAAAF980" bold="true" box="[1222,1333,1562,1581]" italics="true" pageId="6" pageNumber="7">F. fulophazii</emphasis>
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</taxonomicName>
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highly variable, resulting in differences in the amounts of compounds among the isolates and also among the parallel cultures of one isolate.
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||
</paragraph>
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||
</subSubSection>
|
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</treatment>
|
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