treatments-xml/data/03/F0/87/03F087B2FFA8FF80DE47FE1B65C146AE.xml

<document id="F9F719677FA4E7032023C8A7CC9370B5" ID-CLB-Dataset="55407" ID-DOI="10.1016/j.phytochem.2021.112724" ID-GBIF-Dataset="6ab5ae84-2f1d-48bd-9dc3-aa5e175d285d" ID-ISSN="1873-3700" ID-Zenodo-Dep="8276759" IM.bibliography_approvedBy="carolina" IM.illustrations_approvedBy="carolina" IM.materialsCitations_approvedBy="felipe" IM.metadata_approvedBy="felipe" IM.tables_approvedBy="carolina" IM.taxonomicNames_approvedBy="carolina" IM.treatments_approvedBy="carolina" checkinTime="1692306747529" checkinUser="felipe" docAuthor="Jin, Yu, Xu, Yingting, Huang, Zhengwan, Zhou, Zhongyu &amp; Wei, Xiaoyi" docDate="2021" docId="03F087B2FFA8FF80DE47FE1B65C146AE" docLanguage="en" docName="Phytochemistry.186.112724.pdf" docOrigin="Phytochemistry (112724) 186" docSource="http://dx.doi.org/10.1016/j.phytochem.2021.112724" docStyle="DocumentStyle:F36D69FC8B198FBE91029DF9C24697D3.5:Phytochemistry.2020-.journal_article" docStyleId="F36D69FC8B198FBE91029DF9C24697D3" docStyleName="Phytochemistry.2020-.journal_article" docStyleVersion="5" docTitle="Casuarina equisetifolia L." docType="treatment" docVersion="2" lastPageNumber="4" masterDocId="FFC9FFCAFFA9FF83DD75FFD3610E447B" masterDocTitle="Metabolite pattern in root nodules of the actinorhizal plant Casuarina equisetifolia" masterLastPageNumber="6" masterPageNumber="1" pageNumber="2" updateTime="1692798547633" updateUser="ExternalLinkService">
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<mods:title id="BB5C13024BAB9727FD477872E1AF1BEE">Metabolite pattern in root nodules of the actinorhizal plant Casuarina equisetifolia</mods:title>
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<mods:namePart id="74F6104C66C8B460D61D32B475832CA1">Jin, Yu</mods:namePart>
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<mods:namePart id="DB3388B16E45D43FB16C72119B6932A6">Xu, Yingting</mods:namePart>
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<mods:namePart id="07E452D69D15C9469C297DD8B8BC1422">Huang, Zhengwan</mods:namePart>
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<mods:namePart id="2D97D97E806841E104249D61A1353EEB">Zhou, Zhongyu</mods:namePart>
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<emphasis id="B92DEAB6FFA8FF82DE47FE1B65A745A0" bold="true" box="[818,1193,456,475]" italics="true" pageId="1" pageNumber="2">
2.2. Metabolite pattern in 
<taxonomicName id="4C594D27FFA8FF82D951FE1B65A745A0" ID-CoL="RQVW" ID-ENA="3523" authorityName="L." box="[1060,1193,456,475]" class="Magnoliopsida" family="Casuarinaceae" genus="Casuarina" kingdom="Plantae" order="Fagales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="equisetifolia">C. equisetifolia</taxonomicName>
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<paragraph id="8BE636A4FFA8FF82DE24FDD36567405E" blockId="1.[818,1488,512,1982]" pageId="1" pageNumber="2">
The undescribed compound 
<emphasis id="B92DEAB6FFA8FF82D907FDD365704668" bold="true" box="[1138,1150,512,531]" pageId="1" pageNumber="2">1</emphasis>
represents a taraxerane-type triterpene esterified with a phenylpropane dihydrocoumaroyl group. Esterification of triterpenoids generally occurs with phenylpropanoids such as cinnamoyl, coumaroyl, and caffeoyl, which are characterized by an unsaturation in their aliphatic chain (
<bibRefCitation id="EFC84B55FFA8FF82D9CFFDA364AF46F8" author="Connolly, J. D. &amp; Hill, R. A." box="[1210,1441,624,643]" pageId="1" pageNumber="2" pagination="79 - 132" refId="ref6359" refString="Connolly, J. D., Hill, R. A., 2010. Triterpenoids. Nat. Prod. Rep. 27, 79 - 132. https: // doi. org / 10.1039 / b 808530 g." type="journal article" year="2010">Connolly and Hill, 2010</bibRefCitation>
). To our knowledge, this dihydrocoumaroyl group without an unsaturation in its aliphatic chain is less common. Notably, the same dihydrocoumaroyl, but linked with another triterpene, 3- 
<emphasis id="B92DEAB6FFA8FF82D8FCFD10649646AD" bold="true" box="[1417,1432,707,726]" italics="true" pageId="1" pageNumber="2">O</emphasis>
-dihydrocoumaroyl 
<emphasis id="B92DEAB6FFA8FF82DECAFD3362C44688" bold="true" box="[959,970,736,755]" italics="true" pageId="1" pageNumber="2">β</emphasis>
-amyrin (compound S 
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<tableCitation id="C6DB031FFFA8FF82D9B8FD0C642F4689" box="[1229,1313,735,754]" captionStart="Table 1" captionStartId="1.[100,150,1283,1299]" captionTargetPageId="1" captionText="Table 1 1H (500 MHz) and 13C NMR (125 MHz) data of compound 1 in CDCl. 3" httpUri="http://table.plazi.org/id/DF26662CFFA8FF82DD11FAD063B84154" pageId="1" pageNumber="2" tableUuid="DF26662CFFA8FF82DD11FAD063B84154">Table S1</tableCitation>
and 
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) was isolated from the leaves of 
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<emphasis id="B92DEAB6FFA8FF82D947FD2865B84775" bold="true" box="[1074,1206,763,782]" italics="true" pageId="1" pageNumber="2">C. equisetifolia</emphasis>
(
<bibRefCitation id="EFC84B55FFA8FF82D9B0FD2864994775" author="Takahashi, H. &amp; Iuchi, M. &amp; Fujita, Y. &amp; Minami, H. &amp; Fukuyama, Y." box="[1221,1431,763,783]" pageId="1" pageNumber="2" pagination="543 - 550" refId="ref7995" refString="Takahashi, H., Iuchi, M., Fujita, Y., Minami, H., Fukuyama, Y., 1999. Coumaroyl triterpenes from Casuarina equisetifolia. Phytochemistry 51, 543 - 550. https: // doi. org / 10.1016 / s 0031 - 9422 (99) 00070 - 9." type="journal article" year="1999">Takahashi et al., 1999</bibRefCitation>
)
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. The structural difference between 
<emphasis id="B92DEAB6FFA8FF82D926FCCB65504750" bold="true" box="[1107,1118,792,811]" italics="true" pageId="1" pageNumber="2">β</emphasis>
-amyrin and taraxerol lies in the locations of methyl-27 and a double-bond. 
<emphasis id="B92DEAB6FFA8FF82D9EFFCE765AB473C" bold="true" box="[1178,1189,820,839]" italics="true" pageId="1" pageNumber="2">β</emphasis>
-amyrin has methyl-27 linked to C-14, and a double-bond at C-12, while taraxerol has methyl-27 linked to C-13 and a double-bond at C-14. In the HMBC spectrum of compound 
<emphasis id="B92DEAB6FFA8FF82DE47FC55623047E2" bold="true" box="[818,830,902,921]" pageId="1" pageNumber="2">1</emphasis>
, two methyl groups (C-26 and 27) displayed clear correlation peaks with olefinic carbon at 
<emphasis id="B92DEAB6FFA8FF82D979FC71651847CE" bold="true" box="[1036,1046,930,949]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
158.0 (Fig. S9), which supported the structure of taraxerol. Moreover, the double bond at C-14 and C- 
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taraxerol have chemical shifts at about 
<emphasis id="B92DEAB6FFA8FF82D930FC0965414796" bold="true" box="[1093,1103,986,1005]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
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158 (C-14) and 
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117 (C-15), while the double bond at C-12 and C- 
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<emphasis id="B92DEAB6FFA8FF82D913FC24657F4071" bold="true" box="[1126,1137,1015,1034]" italics="true" pageId="1" pageNumber="2">β</emphasis>
-amyrin have chemical shifts at about 
<emphasis id="B92DEAB6FFA8FF82DE47FBC16232405E" bold="true" box="[818,828,1042,1061]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
<subScript id="17DD34E1FFA8FF82DE4EFBCA624B405C" attach="left" box="[827,837,1049,1063]" fontSize="6" pageId="1" pageNumber="2">C</subScript>
145 (C-13) and 
<emphasis id="B92DEAB6FFA8FF82DE97FBC162E2405E" bold="true" box="[994,1004,1042,1061]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
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122 (C-12).
</paragraph>
<paragraph id="8BE636A4FFA8FF82DE24FBFD6569410F" blockId="1.[818,1488,512,1982]" pageId="1" pageNumber="2">
The triterpene biosynthetic pathway of taraxerol and 
<emphasis id="B92DEAB6FFA8FF82D825FBFC64554039" bold="true" box="[1360,1371,1071,1090]" italics="true" pageId="1" pageNumber="2">β</emphasis>
-amyrin was outlined in Fig. S13 (
<bibRefCitation id="EFC84B55FFA8FF82DE8BFB9965974026" author="Han, J. Y. &amp; Jo, H. J. &amp; Kwon, E. K. &amp; Choi, Y. E." box="[1022,1177,1098,1117]" pageId="1" pageNumber="2" pagination="1595 - 1603" refId="ref6812" refString="Han, J. Y., Jo, H. J., Kwon, E. K., Choi, Y. E., 2019. Cloning and characterization of oxidosqualene cyclases Involved in taraxasterol, taraxerol and bauerenol triterpene biosynthesis in Taraxacum coreanum. Plant Cell Physiol. 60, 1595 - 1603. https: // doi. org / 10.1093 / pcp / pcz 062." type="journal article" year="2019">Han et al., 2019</bibRefCitation>
). They are synthesized from the same original precursor, 2,3-oxidosqualene, through protonation, cyclization, and multiple rearrangements. Finally, 
<emphasis id="B92DEAB6FFA8FF82D86DFB51642D40EE" bold="true" box="[1304,1315,1154,1173]" italics="true" pageId="1" pageNumber="2">β</emphasis>
-amyrin is formed through deprotonation of the oleanyl cation, while taraxerol is produced through deprotonation of the taraxareyl cation. 
<emphasis id="B92DEAB6FFA8FF82D99BFB6965F640B6" bold="true" box="[1262,1272,1210,1229]" italics="true" pageId="1" pageNumber="2">p</emphasis>
-Dihydrocoumaric acid appears to be derived from 
<emphasis id="B92DEAB6FFA8FF82D94FFB05654A4092" bold="true" box="[1082,1092,1238,1257]" italics="true" pageId="1" pageNumber="2">p</emphasis>
-coumaric acid. For the transformation of 
<emphasis id="B92DEAB6FFA8FF82DE47FB226232417F" bold="true" box="[818,828,1265,1284]" italics="true" pageId="1" pageNumber="2">p</emphasis>
-coumaric acid to 
<emphasis id="B92DEAB6FFA8FF82D971FB226500417F" bold="true" box="[1028,1038,1265,1284]" italics="true" pageId="1" pageNumber="2">p</emphasis>
-dihydrocoumaric acid, a NADPH-dependent hydroxycinnamoyl-CoA double bond reductase (MdHCDBR) was recently identified and cloned from 
<taxonomicName id="4C594D27FFA8FF82D9F1FAFA64164147" box="[1156,1304,1321,1340]" class="Magnoliopsida" family="Rosaceae" genus="Malus" kingdom="Plantae" order="Rosales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="domestica">
<emphasis id="B92DEAB6FFA8FF82D9F1FAFA64164147" bold="true" box="[1156,1304,1321,1340]" italics="true" pageId="1" pageNumber="2">Malus domestica</emphasis>
</taxonomicName>
(apple tree) (
<bibRefCitation id="EFC84B55FFA8FF82D8ECFAFA62974123" author="Ibdah, M. &amp; Berim, A. &amp; Martens, S. &amp; Valderrama, A. L. H. &amp; Palmieri, L. &amp; Lewinsohn, E. &amp; Gang, D. R." pageId="1" pageNumber="2" pagination="24 - 31" refId="ref6981" refString="Ibdah, M., Berim, A., Martens, S., Valderrama, A. L. H., Palmieri, L., Lewinsohn, E., Gang, D. R., 2014. Identification and cloning of an NADPH-dependent hydroxycinnamoyl-CoA double bond reductase involved in dihydrochalcone formation in Malus x domestica Borkh. Phytochemistry 107, 24 - 31. https: // doi. org / 10.1016 / j. phytochem. 2014.07.027." type="journal article" year="2014">Ibdah et al., 2014</bibRefCitation>
). The results of our study suggest that 
<taxonomicName id="4C594D27FFA8FF82D98FFA9664724123" box="[1274,1404,1349,1368]" class="Magnoliopsida" family="Casuarinaceae" genus="Casuarina" kingdom="Plantae" order="Fagales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="equisetifolia">
<emphasis id="B92DEAB6FFA8FF82D98FFA9664724123" bold="true" box="[1274,1404,1349,1368]" italics="true" pageId="1" pageNumber="2">C. equisetifolia</emphasis>
</taxonomicName>
contains a similar double bond reductase.
</paragraph>
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<emphasis id="B92DEAB6FFA8FF82DD11FAD061A94168" bold="true" box="[100,167,1282,1299]" pageId="1" pageNumber="2">Table 1</emphasis>
</paragraph>
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H (500 MHz) and 
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C NMR (125 MHz) data of compound 
<emphasis id="B92DEAB6FFA8FF82DF29FACF63694156" bold="true" box="[604,615,1308,1325]" pageId="1" pageNumber="2">1</emphasis>
in CDCl.
</paragraph>
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<table id="F959C404FFA8007CDD01FA9263E943EC" box="[116,743,1345,1943]" gridcols="6" gridrows="26" pageId="1" pageNumber="2">
<tr id="356934E6FFA8007CDD01FA9263E94129" box="[116,743,1345,1362]" gridrow="0" pageId="1" pageNumber="2">
<th id="76B85D9AFFA8007CDD01FA92619E4129" box="[116,144,1345,1362]" gridcol="0" gridrow="0" pageId="1" pageNumber="2">No.</th>
<th id="76B85D9AFFA8007CDDD8FA9261E74129" box="[173,233,1345,1362]" gridcol="1" gridrow="0" pageId="1" pageNumber="2">
<emphasis id="B92DEAB6FFA8FF82DDD8FA9261BB4134" bold="true" box="[173,181,1345,1359]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
C
</th>
<th id="76B85D9AFFA8007CDC7DFA9260BA4129" box="[264,436,1345,1362]" gridcol="2" gridrow="0" pageId="1" pageNumber="2">
<emphasis id="B92DEAB6FFA8FF82DC7DFA92601E4134" bold="true" box="[264,272,1345,1359]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
H
</th>
<th id="76B85D9AFFA8007CDCA0FA9260FB4129" box="[469,501,1345,1362]" gridcol="3" gridrow="0" pageId="1" pageNumber="2">No.</th>
<th id="76B85D9AFFA8007CDF61FA92635E4129" box="[532,592,1345,1362]" gridcol="4" gridrow="0" pageId="1" pageNumber="2">
<emphasis id="B92DEAB6FFA8FF82DF61FA9263124134" bold="true" box="[532,540,1345,1359]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
C
</th>
<th id="76B85D9AFFA8007CDF1AFA9263E94129" box="[623,743,1345,1362]" gridcol="5" gridrow="0" pageId="1" pageNumber="2">
<emphasis id="B92DEAB6FFA8FF82DF1AFA9263794134" bold="true" box="[623,631,1345,1359]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
H
</th>
</tr>
<tr id="356934E6FFA8007CDD01FAB363E94109" box="[116,743,1376,1394]" gridrow="1" pageId="1" pageNumber="2" rowspan-5="1">
<th id="76B85D9AFFA8007CDD01FAB3619E4109" box="[116,144,1376,1394]" gridcol="0" gridrow="1" pageId="1" pageNumber="2">1</th>
<td id="76B85D9AFFA8007CDDD8FAB361E74109" box="[173,233,1376,1394]" gridcol="1" gridrow="1" pageId="1" pageNumber="2">37.3, t</td>
<td id="76B85D9AFFA8007CDC7DFAB360BA4109" box="[264,436,1376,1394]" gridcol="2" gridrow="1" pageId="1" pageNumber="2">0.97 a, 1.61 a</td>
<td id="76B85D9AFFA8007CDCA0FAB360FB4109" box="[469,501,1376,1394]" gridcol="3" gridrow="1" pageId="1" pageNumber="2">20</td>
<td id="76B85D9AFFA8007CDF61FAB3635E4109" box="[532,592,1376,1394]" gridcol="4" gridrow="1" pageId="1" pageNumber="2">28.8, s</td>
</tr>
<tr id="356934E6FFA8007CDD01FAA463E941F2" box="[116,743,1399,1417]" gridrow="2" pageId="1" pageNumber="2">
<th id="76B85D9AFFA8007CDD01FAA4619E41F2" box="[116,144,1399,1417]" gridcol="0" gridrow="2" pageId="1" pageNumber="2">2</th>
<td id="76B85D9AFFA8007CDDD8FAA461E741F2" box="[173,233,1399,1417]" gridcol="1" gridrow="2" pageId="1" pageNumber="2">23.4, t</td>
<td id="76B85D9AFFA8007CDC7DFAA460BA41F2" box="[264,436,1399,1417]" gridcol="2" gridrow="2" pageId="1" pageNumber="2">1.57 a</td>
<td id="76B85D9AFFA8007CDCA0FAA460FB41F2" box="[469,501,1399,1417]" gridcol="3" gridrow="2" pageId="1" pageNumber="2">21</td>
<td id="76B85D9AFFA8007CDF61FAA4635E41F2" box="[532,592,1399,1417]" gridcol="4" gridrow="2" pageId="1" pageNumber="2">33.1, t</td>
<td id="76B85D9AFFA8007CDF1AFAA463E941F2" box="[623,743,1399,1417]" gridcol="5" gridrow="2" pageId="1" pageNumber="2">1.25 a, 1.33 a</td>
</tr>
<tr id="356934E6FFA8007CDD01FA5D63E941DB" box="[116,743,1422,1440]" gridrow="3" pageId="1" pageNumber="2">
<th id="76B85D9AFFA8007CDD01FA5D619E41DB" box="[116,144,1422,1440]" gridcol="0" gridrow="3" pageId="1" pageNumber="2">3</th>
<td id="76B85D9AFFA8007CDDD8FA5D61E741DB" box="[173,233,1422,1440]" gridcol="1" gridrow="3" pageId="1" pageNumber="2">81.1, d</td>
<td id="76B85D9AFFA8007CDC7DFA5D60BA41DB" box="[264,436,1422,1440]" gridcol="2" gridrow="3" pageId="1" pageNumber="2">
4.46 (dd, 
<emphasis id="B92DEAB6FFA8FF82DC27FA41605441DB" bold="true" box="[338,346,1426,1440]" italics="true" pageId="1" pageNumber="2">J</emphasis>
= 10.7, 5.4
</td>
<td id="76B85D9AFFA8007CDCA0FA5D60FB41DB" box="[469,501,1422,1440]" gridcol="3" gridrow="3" pageId="1" pageNumber="2">22</td>
<td id="76B85D9AFFA8007CDF61FA5D635E41DB" box="[532,592,1422,1440]" gridcol="4" gridrow="3" pageId="1" pageNumber="2">35.1, t</td>
<td id="76B85D9AFFA8007CDF1AFA5D63E941DB" box="[623,743,1422,1440]" gridcol="5" gridrow="3" pageId="1" pageNumber="2">1.02 a, 1.38 a</td>
</tr>
<tr id="356934E6FFA8007CDD01FA7A63E941CC" box="[116,743,1449,1463]" gridrow="4" pageId="1" pageNumber="2" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-4="1" rowspan-5="1">
<td id="76B85D9AFFA8007CDC7DFA7A60BA41CC" box="[264,436,1449,1463]" gridcol="2" gridrow="4" pageId="1" pageNumber="2">Hz)</td>
</tr>
<tr id="356934E6FFA8007CDD01FA6F63E941B5" box="[116,743,1468,1486]" gridrow="5" pageId="1" pageNumber="2" rowspan-2="1">
<th id="76B85D9AFFA8007CDD01FA6F619E41B5" box="[116,144,1468,1486]" gridcol="0" gridrow="5" pageId="1" pageNumber="2">4</th>
<td id="76B85D9AFFA8007CDDD8FA6F61E741B5" box="[173,233,1468,1486]" gridcol="1" gridrow="5" pageId="1" pageNumber="2">37.9, s</td>
<td id="76B85D9AFFA8007CDCA0FA6F60FB41B5" box="[469,501,1468,1486]" gridcol="3" gridrow="5" pageId="1" pageNumber="2">23</td>
<td id="76B85D9AFFA8007CDF61FA6F635E41B5" box="[532,592,1468,1486]" gridcol="4" gridrow="5" pageId="1" pageNumber="2">27.9, q</td>
<td id="76B85D9AFFA8007CDF1AFA6F63E941B5" box="[623,743,1468,1486]" gridcol="5" gridrow="5" pageId="1" pageNumber="2">0.78 (s) a</td>
</tr>
<tr id="356934E6FFA8007CDD01FA0063E9419E" box="[116,743,1491,1509]" gridrow="6" pageId="1" pageNumber="2">
<th id="76B85D9AFFA8007CDD01FA00619E419E" box="[116,144,1491,1509]" gridcol="0" gridrow="6" pageId="1" pageNumber="2">5</th>
<td id="76B85D9AFFA8007CDDD8FA0061E7419E" box="[173,233,1491,1509]" gridcol="1" gridrow="6" pageId="1" pageNumber="2">55.6, d</td>
<td id="76B85D9AFFA8007CDC7DFA0060BA419E" box="[264,436,1491,1509]" gridcol="2" gridrow="6" pageId="1" pageNumber="2">0.86 a</td>
<td id="76B85D9AFFA8007CDCA0FA0060FB419E" box="[469,501,1491,1509]" gridcol="3" gridrow="6" pageId="1" pageNumber="2">24</td>
<td id="76B85D9AFFA8007CDF61FA00635E419E" box="[532,592,1491,1509]" gridcol="4" gridrow="6" pageId="1" pageNumber="2">16.6, q</td>
<td id="76B85D9AFFA8007CDF1AFA0063E9419E" box="[623,743,1491,1509]" gridcol="5" gridrow="6" pageId="1" pageNumber="2">0.84 (s) a</td>
</tr>
<tr id="356934E6FFA8007CDD01FA3963E94187" box="[116,743,1514,1532]" gridrow="7" pageId="1" pageNumber="2">
<th id="76B85D9AFFA8007CDD01FA39619E4187" box="[116,144,1514,1532]" gridcol="0" gridrow="7" pageId="1" pageNumber="2">6</th>
<td id="76B85D9AFFA8007CDDD8FA3961E74187" box="[173,233,1514,1532]" gridcol="1" gridrow="7" pageId="1" pageNumber="2">18.7, t</td>
<td id="76B85D9AFFA8007CDC7DFA3960BA4187" box="[264,436,1514,1532]" gridcol="2" gridrow="7" pageId="1" pageNumber="2">1.46 a, 1.57 a</td>
<td id="76B85D9AFFA8007CDCA0FA3960FB4187" box="[469,501,1514,1532]" gridcol="3" gridrow="7" pageId="1" pageNumber="2">25</td>
<td id="76B85D9AFFA8007CDF61FA39635E4187" box="[532,592,1514,1532]" gridcol="4" gridrow="7" pageId="1" pageNumber="2">15.5, q</td>
<td id="76B85D9AFFA8007CDF1AFA3963E94187" box="[623,743,1514,1532]" gridcol="5" gridrow="7" pageId="1" pageNumber="2">0.95 (s)</td>
</tr>
<tr id="356934E6FFA8007CDD01F9D363E94269" box="[116,743,1536,1554]" gridrow="8" pageId="1" pageNumber="2">
<th id="76B85D9AFFA8007CDD01F9D3619E4269" box="[116,144,1536,1554]" gridcol="0" gridrow="8" pageId="1" pageNumber="2">7</th>
<td id="76B85D9AFFA8007CDDD8F9D361E74269" box="[173,233,1536,1554]" gridcol="1" gridrow="8" pageId="1" pageNumber="2">41.2, t</td>
<td id="76B85D9AFFA8007CDC7DF9D360BA4269" box="[264,436,1536,1554]" gridcol="2" gridrow="8" pageId="1" pageNumber="2">1.35 a, 2.02 a</td>
<td id="76B85D9AFFA8007CDCA0F9D360FB4269" box="[469,501,1536,1554]" gridcol="3" gridrow="8" pageId="1" pageNumber="2">26</td>
<td id="76B85D9AFFA8007CDF61F9D3635E4269" box="[532,592,1536,1554]" gridcol="4" gridrow="8" pageId="1" pageNumber="2">25.9, q</td>
<td id="76B85D9AFFA8007CDF1AF9D363E94269" box="[623,743,1536,1554]" gridcol="5" gridrow="8" pageId="1" pageNumber="2">1.08 (s)</td>
</tr>
<tr id="356934E6FFA8007CDD01F9C863E94252" box="[116,743,1563,1577]" gridrow="9" pageId="1" pageNumber="2" rowspan-2="1">
<th id="76B85D9AFFA8007CDD01F9C8619E4252" box="[116,144,1563,1577]" gridcol="0" gridrow="9" pageId="1" pageNumber="2">8</th>
<td id="76B85D9AFFA8007CDDD8F9C861E74252" box="[173,233,1563,1577]" gridcol="1" gridrow="9" pageId="1" pageNumber="2">39.0, s</td>
<td id="76B85D9AFFA8007CDCA0F9C860FB4252" box="[469,501,1563,1577]" gridcol="3" gridrow="9" pageId="1" pageNumber="2">27</td>
<td id="76B85D9AFFA8007CDF61F9C8635E4252" box="[532,592,1563,1577]" gridcol="4" gridrow="9" pageId="1" pageNumber="2">21.3, q</td>
<td id="76B85D9AFFA8007CDF1AF9C863E94252" box="[623,743,1563,1577]" gridcol="5" gridrow="9" pageId="1" pageNumber="2">0.90 (s)</td>
</tr>
<tr id="356934E6FFA8007CDD01F9FD63E9423B" box="[116,743,1582,1600]" gridrow="10" pageId="1" pageNumber="2">
<th id="76B85D9AFFA8007CDD01F9FD619E423B" box="[116,144,1582,1600]" gridcol="0" gridrow="10" pageId="1" pageNumber="2">9</th>
<td id="76B85D9AFFA8007CDDD8F9FD61E7423B" box="[173,233,1582,1600]" gridcol="1" gridrow="10" pageId="1" pageNumber="2">49.2, d</td>
<td id="76B85D9AFFA8007CDC7DF9FD60BA423B" box="[264,436,1582,1600]" gridcol="2" gridrow="10" pageId="1" pageNumber="2">1.42 a</td>
<td id="76B85D9AFFA8007CDCA0F9FD60FB423B" box="[469,501,1582,1600]" gridcol="3" gridrow="10" pageId="1" pageNumber="2">28</td>
<td id="76B85D9AFFA8007CDF61F9FD635E423B" box="[532,592,1582,1600]" gridcol="4" gridrow="10" pageId="1" pageNumber="2">29.8, q</td>
<td id="76B85D9AFFA8007CDF1AF9FD63E9423B" box="[623,743,1582,1600]" gridcol="5" gridrow="10" pageId="1" pageNumber="2">0.82 (s)</td>
</tr>
<tr id="356934E6FFA8007CDD01F99A63E9422C" box="[116,743,1609,1623]" gridrow="11" pageId="1" pageNumber="2" rowspan-2="1">
<th id="76B85D9AFFA8007CDD01F99A619E422C" box="[116,144,1609,1623]" gridcol="0" gridrow="11" pageId="1" pageNumber="2">10</th>
<td id="76B85D9AFFA8007CDDD8F99A61E7422C" box="[173,233,1609,1623]" gridcol="1" gridrow="11" pageId="1" pageNumber="2">37.7, s</td>
<td id="76B85D9AFFA8007CDCA0F99A60FB422C" box="[469,501,1609,1623]" gridcol="3" gridrow="11" pageId="1" pageNumber="2">29</td>
<td id="76B85D9AFFA8007CDF61F99A635E422C" box="[532,592,1609,1623]" gridcol="4" gridrow="11" pageId="1" pageNumber="2">33.3, q</td>
<td id="76B85D9AFFA8007CDF1AF99A63E9422C" box="[623,743,1609,1623]" gridcol="5" gridrow="11" pageId="1" pageNumber="2">0.94 (s)</td>
</tr>
<tr id="356934E6FFA8007CDD01F98F63E94215" box="[116,743,1628,1646]" gridrow="12" pageId="1" pageNumber="2">
<th id="76B85D9AFFA8007CDD01F98F619E4215" box="[116,144,1628,1646]" gridcol="0" gridrow="12" pageId="1" pageNumber="2">11</th>
<td id="76B85D9AFFA8007CDDD8F98F61E74215" box="[173,233,1628,1646]" gridcol="1" gridrow="12" pageId="1" pageNumber="2">17.5, t</td>
<td id="76B85D9AFFA8007CDC7DF98F60BA4215" box="[264,436,1628,1646]" gridcol="2" gridrow="12" pageId="1" pageNumber="2">1.48 a, 1.63 a</td>
<td id="76B85D9AFFA8007CDCA0F98F60FB4215" box="[469,501,1628,1646]" gridcol="3" gridrow="12" pageId="1" pageNumber="2">30</td>
<td id="76B85D9AFFA8007CDF61F98F635E4215" box="[532,592,1628,1646]" gridcol="4" gridrow="12" pageId="1" pageNumber="2">29.9, q</td>
<td id="76B85D9AFFA8007CDF1AF98F63E94215" box="[623,743,1628,1646]" gridcol="5" gridrow="12" pageId="1" pageNumber="2">0.91 (s)</td>
</tr>
<tr id="356934E6FFA8007CDD01F9A063E942FE" box="[116,743,1651,1669]" gridrow="13" pageId="1" pageNumber="2" rowspan-5="1">
<th id="76B85D9AFFA8007CDD01F9A0619E42FE" box="[116,144,1651,1669]" gridcol="0" gridrow="13" pageId="1" pageNumber="2">12</th>
<td id="76B85D9AFFA8007CDDD8F9A061E742FE" box="[173,233,1651,1669]" gridcol="1" gridrow="13" pageId="1" pageNumber="2">33.7, t</td>
<td id="76B85D9AFFA8007CDC7DF9A060BA42FE" box="[264,436,1651,1669]" gridcol="2" gridrow="13" pageId="1" pageNumber="2">1.61 a</td>
<td id="76B85D9AFFA8007CDCA0F9A060FB42FE" box="[469,501,1651,1669]" gridcol="3" gridrow="13" pageId="1" pageNumber="2">1′</td>
<td id="76B85D9AFFA8007CDF61F9A0635E42FE" box="[532,592,1651,1669]" gridcol="4" gridrow="13" pageId="1" pageNumber="2">172.8, s</td>
</tr>
<tr id="356934E6FFA8007CDD01F95863E942E0" box="[116,743,1675,1691]" gridrow="14" pageId="1" pageNumber="2" rowspan-2="1">
<th id="76B85D9AFFA8007CDD01F958619E42E0" box="[116,144,1675,1691]" gridcol="0" gridrow="14" pageId="1" pageNumber="2">13</th>
<td id="76B85D9AFFA8007CDDD8F95861E742E0" box="[173,233,1675,1691]" gridcol="1" gridrow="14" pageId="1" pageNumber="2">37.5, s</td>
<td id="76B85D9AFFA8007CDCA0F95860FB42E0" box="[469,501,1675,1691]" gridcol="3" gridrow="14" pageId="1" pageNumber="2">2′</td>
<td id="76B85D9AFFA8007CDF61F958635E42E0" box="[532,592,1675,1691]" gridcol="4" gridrow="14" pageId="1" pageNumber="2">36.5, t</td>
<td id="76B85D9AFFA8007CDF1AF95863E942E0" box="[623,743,1675,1691]" gridcol="5" gridrow="14" pageId="1" pageNumber="2">
2.58 (t, 
<emphasis id="B92DEAB6FFA8FF82DFD9F95E63BA42E0" bold="true" box="[684,692,1677,1691]" italics="true" pageId="1" pageNumber="2">J</emphasis>
= 7.8
</td>
</tr>
<tr id="356934E6FFA8007CDD01F97763E942C9" box="[116,743,1700,1714]" gridrow="15" pageId="1" pageNumber="2" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-4="1">
<td id="76B85D9AFFA8007CDF1AF97763E942C9" box="[623,743,1700,1714]" gridcol="5" gridrow="15" pageId="1" pageNumber="2">Hz)</td>
</tr>
<tr id="356934E6FFA8007CDD01F96A63E942B2" box="[116,743,1721,1737]" gridrow="16" pageId="1" pageNumber="2" rowspan-2="1">
<th id="76B85D9AFFA8007CDD01F96A619E42B2" box="[116,144,1721,1737]" gridcol="0" gridrow="16" pageId="1" pageNumber="2">14</th>
<td id="76B85D9AFFA8007CDDD8F96A61E742B2" box="[173,233,1721,1737]" gridcol="1" gridrow="16" pageId="1" pageNumber="2">158.0, s</td>
<td id="76B85D9AFFA8007CDCA0F96A60FB42B2" box="[469,501,1721,1737]" gridcol="3" gridrow="16" pageId="1" pageNumber="2">3′</td>
<td id="76B85D9AFFA8007CDF61F96A635E42B2" box="[532,592,1721,1737]" gridcol="4" gridrow="16" pageId="1" pageNumber="2">30.2, t</td>
<td id="76B85D9AFFA8007CDF1AF96A63E942B2" box="[623,743,1721,1737]" gridcol="5" gridrow="16" pageId="1" pageNumber="2">
2.88 (t, 
<emphasis id="B92DEAB6FFA8FF82DFD9F96863BA42B2" bold="true" box="[684,692,1723,1737]" italics="true" pageId="1" pageNumber="2">J</emphasis>
= 7.8
</td>
</tr>
<tr id="356934E6FFA8007CDD01F90163E9429B" box="[116,743,1746,1760]" gridrow="17" pageId="1" pageNumber="2" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-4="1">
<td id="76B85D9AFFA8007CDF1AF90163E9429B" box="[623,743,1746,1760]" gridcol="5" gridrow="17" pageId="1" pageNumber="2">Hz)</td>
</tr>
<tr id="356934E6FFA8007CDD01F93463E9428C" box="[116,743,1767,1783]" gridrow="18" pageId="1" pageNumber="2" rowspan-5="1">
<th id="76B85D9AFFA8007CDD01F934619E428C" box="[116,144,1767,1783]" gridcol="0" gridrow="18" pageId="1" pageNumber="2">15</th>
<td id="76B85D9AFFA8007CDDD8F93461E7428C" box="[173,233,1767,1783]" gridcol="1" gridrow="18" pageId="1" pageNumber="2">116.9,</td>
<td id="76B85D9AFFA8007CDC7DF93460BA428C" box="[264,436,1767,1783]" gridcol="2" gridrow="18" pageId="1" pageNumber="2">
5.53 (dd, 
<emphasis id="B92DEAB6FFA8FF82DC27F93A6054428C" bold="true" box="[338,346,1769,1783]" italics="true" pageId="1" pageNumber="2">J</emphasis>
= 8.2, 3.2
</td>
<td id="76B85D9AFFA8007CDCA0F93460FB428C" box="[469,501,1767,1783]" gridcol="3" gridrow="18" pageId="1" pageNumber="2">4′</td>
<td id="76B85D9AFFA8007CDF61F934635E428C" box="[532,592,1767,1783]" gridcol="4" gridrow="18" pageId="1" pageNumber="2">132.8, s</td>
</tr>
<tr id="356934E6FFA8007CDD01F92C63E94376" box="[116,743,1791,1805]" gridrow="19" pageId="1" pageNumber="2" rowspan-0="1" rowspan-3="1" rowspan-4="1" rowspan-5="1">
<td id="76B85D9AFFA8007CDDD8F92C61E74376" box="[173,233,1791,1805]" gridcol="1" gridrow="19" pageId="1" pageNumber="2">d</td>
<td id="76B85D9AFFA8007CDC7DF92C60BA4376" box="[264,436,1791,1805]" gridcol="2" gridrow="19" pageId="1" pageNumber="2">Hz)</td>
</tr>
<tr id="356934E6FFA8007CDD01F8C163E9435F" box="[116,743,1810,1828]" gridrow="20" pageId="1" pageNumber="2">
<th id="76B85D9AFFA8007CDD01F8C1619E435F" box="[116,144,1810,1828]" gridcol="0" gridrow="20" pageId="1" pageNumber="2">16</th>
<td id="76B85D9AFFA8007CDDD8F8C161E7435F" box="[173,233,1810,1828]" gridcol="1" gridrow="20" pageId="1" pageNumber="2">37.7, t</td>
<td id="76B85D9AFFA8007CDC7DF8C160BA435F" box="[264,436,1810,1828]" gridcol="2" gridrow="20" pageId="1" pageNumber="2">1.61 a, 1.92 a</td>
<td id="76B85D9AFFA8007CDCA0F8C160FB435F" box="[469,501,1810,1828]" gridcol="3" gridrow="20" pageId="1" pageNumber="2">5′,9′</td>
<td id="76B85D9AFFA8007CDF61F8C1635E435F" box="[532,592,1810,1828]" gridcol="4" gridrow="20" pageId="1" pageNumber="2">129.4,</td>
<td id="76B85D9AFFA8007CDF1AF8C163E9435F" box="[623,743,1810,1828]" gridcol="5" gridrow="20" pageId="1" pageNumber="2">
7.07 (d, 
<emphasis id="B92DEAB6FFA8FF82DFDAF8C563B9435F" bold="true" box="[687,695,1814,1828]" italics="true" pageId="1" pageNumber="2">J</emphasis>
= 8.4
</td>
</tr>
<tr id="356934E6FFA8007CDD01F8FE63E94340" box="[116,743,1837,1851]" gridrow="21" pageId="1" pageNumber="2" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1">
<td id="76B85D9AFFA8007CDF61F8FE635E4340" box="[532,592,1837,1851]" gridcol="4" gridrow="21" pageId="1" pageNumber="2">d</td>
<td id="76B85D9AFFA8007CDF1AF8FE63E94340" box="[623,743,1837,1851]" gridcol="5" gridrow="21" pageId="1" pageNumber="2">Hz)</td>
</tr>
<tr id="356934E6FFA8007CDD01F89163E94329" box="[116,743,1858,1874]" gridrow="22" pageId="1" pageNumber="2" rowspan-2="1">
<th id="76B85D9AFFA8007CDD01F891619E4329" box="[116,144,1858,1874]" gridcol="0" gridrow="22" pageId="1" pageNumber="2">17</th>
<td id="76B85D9AFFA8007CDDD8F89161E74329" box="[173,233,1858,1874]" gridcol="1" gridrow="22" pageId="1" pageNumber="2">35.8, s</td>
<td id="76B85D9AFFA8007CDCA0F89160FB4329" box="[469,501,1858,1874]" gridcol="3" gridrow="22" pageId="1" pageNumber="2">6′,8′</td>
<td id="76B85D9AFFA8007CDF61F891635E4329" box="[532,592,1858,1874]" gridcol="4" gridrow="22" pageId="1" pageNumber="2">115.3,</td>
<td id="76B85D9AFFA8007CDF1AF89163E94329" box="[623,743,1858,1874]" gridcol="5" gridrow="22" pageId="1" pageNumber="2">
6.74 (d, 
<emphasis id="B92DEAB6FFA8FF82DFDAF89763B94329" bold="true" box="[687,695,1860,1874]" italics="true" pageId="1" pageNumber="2">J</emphasis>
= 8.4
</td>
</tr>
<tr id="356934E6FFA8007CDD01F88863E94312" box="[116,743,1883,1897]" gridrow="23" pageId="1" pageNumber="2" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1">
<td id="76B85D9AFFA8007CDF61F888635E4312" box="[532,592,1883,1897]" gridcol="4" gridrow="23" pageId="1" pageNumber="2">d</td>
<td id="76B85D9AFFA8007CDF1AF88863E94312" box="[623,743,1883,1897]" gridcol="5" gridrow="23" pageId="1" pageNumber="2">Hz)</td>
</tr>
<tr id="356934E6FFA8007CDD01F8BD63E943FB" box="[116,743,1902,1920]" gridrow="24" pageId="1" pageNumber="2" rowspan-5="1">
<th id="76B85D9AFFA8007CDD01F8BD619E43FB" box="[116,144,1902,1920]" gridcol="0" gridrow="24" pageId="1" pageNumber="2">18</th>
<td id="76B85D9AFFA8007CDDD8F8BD61E743FB" box="[173,233,1902,1920]" gridcol="1" gridrow="24" pageId="1" pageNumber="2">48.7, d</td>
<td id="76B85D9AFFA8007CDC7DF8BD60BA43FB" box="[264,436,1902,1920]" gridcol="2" gridrow="24" pageId="1" pageNumber="2">0.95 a</td>
<td id="76B85D9AFFA8007CDCA0F8BD60FB43FB" box="[469,501,1902,1920]" gridcol="3" gridrow="24" pageId="1" pageNumber="2">7′</td>
<td id="76B85D9AFFA8007CDF61F8BD635E43FB" box="[532,592,1902,1920]" gridcol="4" gridrow="24" pageId="1" pageNumber="2">153.9, s</td>
</tr>
<tr id="356934E6FFA8007CDD01F85663E943EC" box="[116,743,1925,1943]" gridrow="25" pageId="1" pageNumber="2" rowspan-3="1" rowspan-4="1" rowspan-5="1">
<th id="76B85D9AFFA8007CDD01F856619E43EC" box="[116,144,1925,1943]" gridcol="0" gridrow="25" pageId="1" pageNumber="2">19</th>
<td id="76B85D9AFFA8007CDDD8F85661E743EC" box="[173,233,1925,1943]" gridcol="1" gridrow="25" pageId="1" pageNumber="2">36.6, t</td>
<td id="76B85D9AFFA8007CDC7DF85660BA43EC" box="[264,436,1925,1943]" gridcol="2" gridrow="25" pageId="1" pageNumber="2">0.96 a, 1.31 a</td>
</tr>
</table>
</paragraph>
<paragraph id="8BE636A4FFA8FF82DE24FAAE64DE42F0" blockId="1.[818,1488,512,1982]" pageId="1" pageNumber="2">
We compared metabolites reported from various organs of 
<taxonomicName id="4C594D27FFA8FF82DE47FA4B62B641D0" box="[818,952,1432,1451]" class="Magnoliopsida" family="Casuarinaceae" genus="Casuarina" kingdom="Plantae" order="Fagales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="equisetifolia">
<emphasis id="B92DEAB6FFA8FF82DE47FA4B62B641D0" bold="true" box="[818,952,1432,1451]" italics="true" pageId="1" pageNumber="2">C. equisetifolia</emphasis>
</taxonomicName>
(
<tableCitation id="C6DB031FFFA8FF82DEBFFA4A651041D7" box="[970,1054,1433,1452]" captionStart="Table 1" captionStartId="1.[100,150,1283,1299]" captionTargetPageId="1" captionText="Table 1 1H (500 MHz) and 13C NMR (125 MHz) data of compound 1 in CDCl. 3" httpUri="http://table.plazi.org/id/DF26662CFFA8FF82DD11FAD063B84154" pageId="1" pageNumber="2" tableUuid="DF26662CFFA8FF82DD11FAD063B84154">Table S1</tableCitation>
and 
<figureCitation id="13622A21FFA8FF82D921FA4A659941D7" box="[1108,1175,1433,1452]" captionStart="Fig" captionStartId="2.[100,130,1913,1930]" captionTargetBox="[302,1271,604,1885]" captionTargetId="figure-273@2.[305,1286,1040,1509]" captionTargetPageId="2" captionText="Fig. 2. 1H-NMR spectra of root nodule extracts of C. equisetifolia. (A) A 1H-NMR spectrum of extracts of hydrophobic compounds. (B) A 1H-NMR spectrum of extracts of hydrophilic compounds. (C) Magnified part of the 1H-NMR spectrum shown in (B). Peaks 1–6 were ascribed to tyramine, tyrosine, malate, citrate, succinate and β-glucose, respectively." figureDoi="http://doi.org/10.5281/zenodo.8276765" httpUri="https://zenodo.org/record/8276765/files/figure.png" pageId="1" pageNumber="2">Fig. S2</figureCitation>
). The results showed that compounds 
<emphasis id="B92DEAB6FFA8FF82DEF5FA6762AD41BC" bold="true" box="[896,931,1460,1480]" pageId="1" pageNumber="2">1–8</emphasis>
and 
<emphasis id="B92DEAB6FFA8FF82DEAFFA67651941BC" bold="true" box="[986,1047,1460,1480]" pageId="1" pageNumber="2">10–13</emphasis>
appeared specifically in the root nodules of 
<taxonomicName id="4C594D27FFA8FF82DE47FA0362B84198" box="[818,950,1488,1507]" class="Magnoliopsida" family="Casuarinaceae" genus="Casuarina" kingdom="Plantae" order="Fagales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="equisetifolia">
<emphasis id="B92DEAB6FFA8FF82DE47FA0362B84198" bold="true" box="[818,950,1488,1507]" italics="true" pageId="1" pageNumber="2">C. equisetifolia</emphasis>
</taxonomicName>
. With regard to the 
<typeStatus id="54E28806FFA8FF82D90BFA0265A9419F" box="[1150,1191,1489,1508]" pageId="1" pageNumber="2">type</typeStatus>
of triterpenoids, the oleanane-type was found in leaves and litter (
<bibRefCitation id="EFC84B55FFA8FF82D9DDFA3F64864184" author="Takahashi, H. &amp; Iuchi, M. &amp; Fujita, Y. &amp; Minami, H. &amp; Fukuyama, Y." box="[1192,1416,1516,1536]" pageId="1" pageNumber="2" pagination="543 - 550" refId="ref7995" refString="Takahashi, H., Iuchi, M., Fujita, Y., Minami, H., Fukuyama, Y., 1999. Coumaroyl triterpenes from Casuarina equisetifolia. Phytochemistry 51, 543 - 550. https: // doi. org / 10.1016 / s 0031 - 9422 (99) 00070 - 9." type="journal article" year="1999">Takahashi et al., 1999</bibRefCitation>
; 
<bibRefCitation id="EFC84B55FFA8FF82D8ECFA3E62AE4260" author="Wang, H. - S. &amp; Dai, H. - F. &amp; Wang, P. &amp; Cai, C. - H. &amp; Zhou, L. - M. &amp; Li, L. &amp; Mei, W. - L." pageId="1" pageNumber="2" pagination="390 - 395" refId="ref8202" refString="Wang, H. - S., Dai, H. - F., Wang, P., Cai, C. - H., Zhou, L. - M., Li, L., Mei, W. - L., 2018. Chemical constituents from litters of Casuarina equisetifolia and their biological activity. Natural Product Research and Development 30, 390 - 395. https: // doi. org / 10.16333 / j. 1001 - 6880.2018.3.008." type="journal article" year="2018">Wang et al., 2018</bibRefCitation>
), whereas lupane, hopane, taraxerane, and euphane-types were found in root nodules in this study. It seems that the carbon skeletons of triterpenoids found in root nodules are more diverse than those in other organs (
<tableCitation id="C6DB031FFFA8FF82DEA6F98F65284214" box="[979,1062,1628,1647]" captionStart="Table 1" captionStartId="1.[100,150,1283,1299]" captionTargetPageId="1" captionText="Table 1 1H (500 MHz) and 13C NMR (125 MHz) data of compound 1 in CDCl. 3" httpUri="http://table.plazi.org/id/DF26662CFFA8FF82DD11FAD063B84154" pageId="1" pageNumber="2" tableUuid="DF26662CFFA8FF82DD11FAD063B84154">Table S1</tableCitation>
and 
<figureCitation id="13622A21FFA8FF82D92DF98F65974214" box="[1112,1177,1628,1647]" captionStart="Fig" captionStartId="2.[100,130,1913,1930]" captionTargetBox="[302,1271,604,1885]" captionTargetId="figure-273@2.[305,1286,1040,1509]" captionTargetPageId="2" captionText="Fig. 2. 1H-NMR spectra of root nodule extracts of C. equisetifolia. (A) A 1H-NMR spectrum of extracts of hydrophobic compounds. (B) A 1H-NMR spectrum of extracts of hydrophilic compounds. (C) Magnified part of the 1H-NMR spectrum shown in (B). Peaks 1–6 were ascribed to tyramine, tyrosine, malate, citrate, succinate and β-glucose, respectively." figureDoi="http://doi.org/10.5281/zenodo.8276765" httpUri="https://zenodo.org/record/8276765/files/figure.png" pageId="1" pageNumber="2">Fig. S2</figureCitation>
), which is probably a symbiotic result between 
<taxonomicName id="4C594D27FFA8FF82DEB7F9A4650942F1" authorityName="Brunchorst" authorityYear="1886" box="[962,1031,1655,1674]" class="Magnoliopsida" family="Asteraceae" genus="Frankia" kingdom="Plantae" order="Asterales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="genus">
<emphasis id="B92DEAB6FFA8FF82DEB7F9A4650942F1" bold="true" box="[962,1031,1655,1674]" italics="true" pageId="1" pageNumber="2">Frankia</emphasis>
</taxonomicName>
and 
<taxonomicName id="4C594D27FFA8FF82D940F9AB65B742F1" box="[1077,1209,1655,1675]" class="Magnoliopsida" family="Casuarinaceae" genus="Casuarina" kingdom="Plantae" order="Fagales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="equisetifolia">
<emphasis id="B92DEAB6FFA8FF82D940F9AB65B742F1" bold="true" box="[1077,1209,1655,1675]" italics="true" pageId="1" pageNumber="2">C. equisetifolia</emphasis>
</taxonomicName>
reflecting in phytochemistry.
</paragraph>
<paragraph id="8BE636A4FFA8FF80DE24F947619B44A5" blockId="1.[818,1488,512,1982]" lastBlockId="3.[100,770,148,418]" lastPageId="3" lastPageNumber="4" pageId="1" pageNumber="2">
22-Hydroxyhopane (
<emphasis id="B92DEAB6FFA8FF82D962F947652D42DC" bold="true" box="[1047,1059,1684,1703]" pageId="1" pageNumber="2">5</emphasis>
) is a hopanoid, member of a class of membrane lipids. The role of hopanoids in facilitating beneficial plant–bacteria interactions, has recently been reviewed (
<bibRefCitation id="EFC84B55FFA8FF82D986F918649942A4" author="Belin, B. J. &amp; Busset, N. &amp; Giraud, E. &amp; Molinaro, A. &amp; Silipo, A. &amp; Newman, D. K." box="[1267,1431,1739,1759]" pageId="1" pageNumber="2" pagination="304 - 315" refId="ref5938" refString="Belin, B. J., Busset, N., Giraud, E., Molinaro, A., Silipo, A., Newman, D. K., 2018. Hopanoid lipids: from membranes to plant-bacteria interactions. Nat. Rev. Microbiol. 16, 304 - 315. https: // doi. org / 10.1038 / nrmicro. 2017.173." type="journal article" year="2018">Belin et al., 2018</bibRefCitation>
). The most common hopanoids formed by 
<taxonomicName id="4C594D27FFA8FF82D9D2F93465E24281" authorityName="Brunchorst" authorityYear="1886" box="[1191,1260,1767,1786]" class="Magnoliopsida" family="Asteraceae" genus="Frankia" kingdom="Plantae" order="Asterales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="genus">
<emphasis id="B92DEAB6FFA8FF82D9D2F93465E24281" bold="true" box="[1191,1260,1767,1786]" italics="true" pageId="1" pageNumber="2">Frankia</emphasis>
</taxonomicName>
strains in actinorhizal nodules are bacteriohopanetetrol (BHT) and phenylacetyl monoester of BHT (phenylacetic acid (PAA)-BHT). Abundant BHT and PAA-BHT in the 
<taxonomicName id="4C594D27FFA8FF82DE23F8E862954335" authorityName="Brunchorst" authorityYear="1886" box="[854,923,1851,1870]" class="Magnoliopsida" family="Asteraceae" genus="Frankia" kingdom="Plantae" order="Asterales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="genus">
<emphasis id="B92DEAB6FFA8FF82DE23F8E862954335" bold="true" box="[854,923,1851,1870]" italics="true" pageId="1" pageNumber="2">Frankia</emphasis>
</taxonomicName>
vesicle envelopes in 
<taxonomicName id="4C594D27FFA8FF82D917F8E8659A4335" box="[1122,1172,1851,1870]" class="Magnoliopsida" family="Betulaceae" genus="Alnus" kingdom="Plantae" order="Fagales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="genus">
<emphasis id="B92DEAB6FFA8FF82D917F8E8659A4335" bold="true" box="[1122,1172,1851,1870]" italics="true" pageId="1" pageNumber="2">Alnus</emphasis>
</taxonomicName>
nodules, are presumptive barrier of oxygen diffusion to nitrogenase (
<bibRefCitation id="EFC84B55FFA8FF82D9F2F88464214311" author="Berry, A. M. &amp; Harriott, O. T. &amp; Moreau, R. A. &amp; Osman, S. F. &amp; Benson, D. R. &amp; Jones, A. D." box="[1159,1327,1879,1898]" pageId="1" pageNumber="2" pagination="6091 - 6094" refId="ref6074" refString="Berry, A. M., Harriott, O. T., Moreau, R. A., Osman, S. F., Benson, D. R., Jones, A. D., 1993. Hopanoid lipids compose the Frankia vesicle envelope, presumptive barrier of oxygen diffusion to nitrogenase. Proc. Natl. Acad. Sci. U. S. A. 90, 6091 - 6094. https: // doi. org / 10.1073 / pnas. 90.13.6091." type="journal article" year="1993">Berry et al., 1993</bibRefCitation>
). However, BHT and PAA-BHT were not isolated from 
<taxonomicName id="4C594D27FFA8FF82D9E7F8A0641A43FE" box="[1170,1300,1906,1926]" class="Magnoliopsida" family="Casuarinaceae" genus="Casuarina" kingdom="Plantae" order="Fagales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="equisetifolia">
<emphasis id="B92DEAB6FFA8FF82D9E7F8A0641A43FE" bold="true" box="[1170,1300,1906,1926]" italics="true" pageId="1" pageNumber="2">C. equisetifolia</emphasis>
</taxonomicName>
root nodules in this study, which is consistent with the fact. In 
<taxonomicName id="4C594D27FFA8FF82D9A7F85C642343D9" box="[1234,1325,1935,1954]" class="Magnoliopsida" family="Casuarinaceae" genus="Casuarina" kingdom="Plantae" order="Fagales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="genus">
<emphasis id="B92DEAB6FFA8FF82D9A7F85C642343D9" bold="true" box="[1234,1325,1935,1954]" italics="true" pageId="1" pageNumber="2">Casuarina</emphasis>
</taxonomicName>
nodules, 
<taxonomicName id="4C594D27FFA8FF82D8FFF85D64C143DA" authorityName="Brunchorst" authorityYear="1886" box="[1418,1487,1934,1953]" class="Magnoliopsida" family="Asteraceae" genus="Frankia" kingdom="Plantae" order="Asterales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="genus">
<emphasis id="B92DEAB6FFA8FF82D8FFF85D64C143DA" bold="true" box="[1418,1487,1934,1953]" italics="true" pageId="1" pageNumber="2">Frankia</emphasis>
</taxonomicName>
does not 
<taxonomicName id="4C594D27FFA8FF82DEB0F878655143C5" box="[965,1119,1963,1982]" form="vesicles" pageId="1" pageNumber="2" rank="form">form vesicles</taxonomicName>
surrounded by multi-layered hopanoid-containing envelopes to provide oxygen protection for nitrogenase; instead, the plant provides microaerobic conditions in infected cells.
</paragraph>
<paragraph id="8BE636A4FFA8FF82DD06F87B631F43C6" blockId="1.[115,529,1960,1981]" box="[115,529,1960,1981]" pageId="1" pageNumber="2">
<tableNote id="76BF372AFFA8FF82DD06F87B631F43C6" box="[115,529,1960,1981]" pageId="1" pageNumber="2" targetBox="[116,743,1345,1943]" targetPageId="1">
<superScript id="7C2C9BECFFA8FF82DD06F87B617443CF" attach="left" box="[115,122,1960,1972]" fontSize="5" pageId="1" pageNumber="2">a</superScript>
Assignments were based on HSQC experiment.
</tableNote>
</paragraph>
<caption id="DF26662CFFABFF81DC12FE3F65C24586" ID-DOI="http://doi.org/10.5281/zenodo.8276763" ID-Zenodo-Dep="8276763" box="[359,1228,492,510]" httpUri="https://zenodo.org/record/8276763/files/figure.png" pageId="2" pageNumber="3" startId="2.[359,389,492,509]" targetBox="[189,1395,148,464]" targetPageId="2" targetType="figure">
<paragraph id="8BE636A4FFABFF81DC12FE3F65C24586" blockId="2.[359,1228,492,510]" box="[359,1228,492,510]" pageId="2" pageNumber="3">
<emphasis id="B92DEAB6FFABFF81DC12FE3F60AE4585" bold="true" box="[359,416,492,510]" pageId="2" pageNumber="3">Fig. 1.</emphasis>
The chemical structure (left) and key HMBC correlations (from H to C, right) of compound 
<emphasis id="B92DEAB6FFABFF81D9C9FE3E65C94585" bold="true" box="[1212,1223,493,510]" pageId="2" pageNumber="3">1</emphasis>
.
</paragraph>
</caption>
<caption id="DF26662CFFABFF81DD11F8AA602543C6" ID-DOI="http://doi.org/10.5281/zenodo.8276765" ID-Zenodo-Dep="8276765" httpUri="https://zenodo.org/record/8276765/files/figure.png" pageId="2" pageNumber="3" startId="2.[100,130,1913,1930]" targetBox="[302,1271,604,1885]" targetPageId="2" targetType="figure">
<paragraph id="8BE636A4FFABFF81DD11F8AA602543C6" blockId="2.[100,1487,1909,1981]" pageId="2" pageNumber="3">
<emphasis id="B92DEAB6FFABFF81DD11F8AA619343F1" bold="true" box="[100,157,1913,1930]" pageId="2" pageNumber="3">Fig. 2.</emphasis>
<superScript id="7C2C9BECFFABFF81DDD3F8A661A043FA" attach="right" box="[166,174,1909,1921]" fontSize="5" pageId="2" pageNumber="3">1</superScript>
H-NMR spectra of root nodule extracts of 
<taxonomicName id="4C594D27FFABFF81DF7EF8AA638F43F1" box="[523,641,1913,1930]" class="Magnoliopsida" family="Casuarinaceae" genus="Casuarina" kingdom="Plantae" order="Fagales" pageId="2" pageNumber="3" phylum="Tracheophyta" rank="species" species="equisetifolia">
<emphasis id="B92DEAB6FFABFF81DF7EF8AA638F43F1" bold="true" box="[523,641,1913,1930]" italics="true" pageId="2" pageNumber="3">C. equisetifolia</emphasis>
</taxonomicName>
. (A) A 
<superScript id="7C2C9BECFFABFF81DFC8F8A663CB43FA" attach="right" box="[701,709,1909,1921]" fontSize="5" pageId="2" pageNumber="3">1</superScript>
H-NMR spectrum of extracts of hydrophobic compounds. (B) A 
<superScript id="7C2C9BECFFABFF81D9ACF8A665EF43FA" attach="right" box="[1241,1249,1909,1921]" fontSize="5" pageId="2" pageNumber="3">1</superScript>
H-NMR spectrum of extracts of hydrophilic compounds. (C) Magnified part of the 
<superScript id="7C2C9BECFFABFF81DF5CF85D633F43E1" attach="right" box="[553,561,1934,1946]" fontSize="5" pageId="2" pageNumber="3">1</superScript>
H-NMR spectrum shown in (B). Peaks 1–6 were ascribed to tyramine, tyrosine, malate, citrate, succinate and 
<emphasis id="B92DEAB6FFABFF81DD11F87F616043C6" bold="true" box="[100,110,1964,1981]" italics="true" pageId="2" pageNumber="3">β</emphasis>
-glucose, respectively.
</paragraph>
</caption>
<paragraph id="8BE636A4FFAAFF80DDF1FF3B633245D9" blockId="3.[100,770,148,418]" pageId="3" pageNumber="4">
Two flavonoids, (+)-Catechin (
<emphasis id="B92DEAB6FFAAFF80DCC4FF3460C44481" bold="true" box="[433,458,231,250]" pageId="3" pageNumber="4">12</emphasis>
) and ()-epicatechin (
<emphasis id="B92DEAB6FFAAFF80DFDFFF3463CD4481" bold="true" box="[682,707,231,250]" pageId="3" pageNumber="4">13</emphasis>
) were isolated from 
<taxonomicName id="4C594D27FFAAFF80DD92FED06064456D" box="[231,362,259,278]" class="Magnoliopsida" family="Casuarinaceae" genus="Casuarina" kingdom="Plantae" order="Fagales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="equisetifolia">
<emphasis id="B92DEAB6FFAAFF80DD92FED06064456D" bold="true" box="[231,362,259,278]" italics="true" pageId="3" pageNumber="4">C. equisetifolia</emphasis>
</taxonomicName>
nodules. Flavonoids are another important class of specialized metabolites both in actinorhizal plants and legumes (
<bibRefCitation id="EFC84B55FFAAFF80DD19FEE860274535" author="Gifford, I. &amp; Battenberg, K. &amp; Vaniya, A. &amp; Wilson, A. &amp; Tian, L. &amp; Fiehn, O. &amp; Berry, A. M." box="[108,297,315,334]" pageId="3" pageNumber="4" refId="ref6728" refString="Gifford, I., Battenberg, K., Vaniya, A., Wilson, A., Tian, L., Fiehn, O., Berry, A. M., 2018. Distinctive patterns of flavonoid biosynthesis in roots and nodules of Datisca glomerata and Medicago spp. revealed by metabolomic and gene expression profiles. Front. Plant Sci. 9 https: // doi. org / 10.3389 / fpls. 2018.01463 article 1463." type="book" year="2018">Gifford et al., 2018</bibRefCitation>
). 
<taxonomicName id="4C594D27FFAAFF80DC35FEE860C84535" box="[320,454,315,334]" class="Magnoliopsida" family="Casuarinaceae" genus="Casuarina" kingdom="Plantae" order="Fagales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="equisetifolia">
<emphasis id="B92DEAB6FFAAFF80DC35FEE860C84535" bold="true" box="[320,454,315,334]" italics="true" pageId="3" pageNumber="4">C. equisetifolia</emphasis>
</taxonomicName>
is rich in flavonoids (
<bibRefCitation id="EFC84B55FFAAFF80DFD6FEE861F24511" author="Saleh, N. A. M. &amp; El-Lakany, M. H." pageId="3" pageNumber="4" pagination="13 - 15" refId="ref7812" refString="Saleh, N. A. M., El-Lakany, M. H., 1979. A quantitative variation in the flavonoids and phenolics of some Casuarina species. Biochem. Systemat. Ecol. 7, 13 - 15. https: // doi. org / 10.1016 / 0305 - 1978 (79) 90034 - 6." type="journal article" year="1979">Saleh and El-Lakany, 1979</bibRefCitation>
) (
<tableCitation id="C6DB031FFFAAFF80DC65FE84606E4511" box="[272,352,343,362]" captionStart="Table 1" captionStartId="1.[100,150,1283,1299]" captionTargetPageId="1" captionText="Table 1 1H (500 MHz) and 13C NMR (125 MHz) data of compound 1 in CDCl. 3" httpUri="http://table.plazi.org/id/DF26662CFFA8FF82DD11FAD063B84154" pageId="3" pageNumber="4" tableUuid="DF26662CFFA8FF82DD11FAD063B84154">Table S1</tableCitation>
and 
<figureCitation id="13622A21FFAAFF80DCFEFE8460C74511" box="[395,457,343,362]" captionStart="Fig" captionStartId="2.[100,130,1913,1930]" captionTargetBox="[302,1271,604,1885]" captionTargetId="figure-273@2.[305,1286,1040,1509]" captionTargetPageId="2" captionText="Fig. 2. 1H-NMR spectra of root nodule extracts of C. equisetifolia. (A) A 1H-NMR spectrum of extracts of hydrophobic compounds. (B) A 1H-NMR spectrum of extracts of hydrophilic compounds. (C) Magnified part of the 1H-NMR spectrum shown in (B). Peaks 1–6 were ascribed to tyramine, tyrosine, malate, citrate, succinate and β-glucose, respectively." figureDoi="http://doi.org/10.5281/zenodo.8276765" httpUri="https://zenodo.org/record/8276765/files/figure.png" pageId="3" pageNumber="4">Fig. S2</figureCitation>
), and flavonoids have been found to play an important role in the early stages of actinorhizal nodulation of 
<taxonomicName id="4C594D27FFAAFF80DD11FE5C61F145DA" box="[100,255,398,418]" class="Magnoliopsida" family="Casuarinaceae" genus="Casuarina" kingdom="Plantae" order="Fagales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="glauca">
<emphasis id="B92DEAB6FFAAFF80DD11FE5C61F145DA" bold="true" box="[100,255,398,418]" italics="true" pageId="3" pageNumber="4">Casuarina glauca</emphasis>
</taxonomicName>
(
<bibRefCitation id="EFC84B55FFAAFF80DC78FE5C60FC45D9" author="Abdel-Lateif, K. &amp; Bogusz, D. &amp; Hocher, V." box="[269,498,399,418]" pageId="3" pageNumber="4" pagination="636 - 641" refId="ref5575" refString="Abdel-Lateif, K., Bogusz, D., Hocher, V., 2012. The role of flavonoids in the establishment of plant roots endosymbioses with arbuscular mycorrhiza fungi, rhizobia and Frankia bacteria. Plant Signal. Behav. 7, 636 - 641. https: // doi. org / 10.4161 / psb. 20039." type="journal article" year="2012">Abdel-Lateif et al., 2012</bibRefCitation>
, 
<bibRefCitation id="EFC84B55FFAAFF80DC8BFE5C632045D9" author="Abdel-Lateif, K. &amp; Vaissayre, V. &amp; Gherbi, H. &amp; Verries, C. &amp; Meudec, E. &amp; Perrine-Walker, F. &amp; Cheynier, V. &amp; Svistoonoff, S. &amp; Franche, C. &amp; Bogusz, D. &amp; Hocher, V." box="[510,558,399,418]" pageId="3" pageNumber="4" pagination="1012 - 1021" refId="ref5637" refString="Abdel-Lateif, K., Vaissayre, V., Gherbi, H., Verries, C., Meudec, E., Perrine-Walker, F., Cheynier, V., Svistoonoff, S., Franche, C., Bogusz, D., Hocher, V., 2013. Silencing of the chalcone synthase gene in Casuarina glauca highlights the important role of flavonoids during nodulation. New Phytol. 199, 1012 - 1021. https: // doi. org / 10.1111 / nph. 12326." type="journal article" year="2013">2013</bibRefCitation>
).
</paragraph>
<paragraph id="8BE636A4FFAAFF80DD11FE1F63DA45A4" blockId="3.[100,724,460,479]" box="[100,724,460,479]" pageId="3" pageNumber="4">
<heading id="D0AE81C8FFAAFF80DD11FE1F63DA45A4" bold="true" box="[100,724,460,479]" fontSize="36" level="1" pageId="3" pageNumber="4" reason="1">
<emphasis id="B92DEAB6FFAAFF80DD11FE1F63DA45A4" bold="true" box="[100,724,460,479]" italics="true" pageId="3" pageNumber="4">
2.3. Contents and physiological effects of tyramine in 
<taxonomicName id="4C594D27FFAAFF80DF3AFE1F63DA45A4" ID-CoL="RQVW" ID-ENA="3523" box="[591,724,460,479]" class="Magnoliopsida" family="Casuarinaceae" genus="Casuarina" kingdom="Plantae" order="Fagales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="equisetifolia">C. equisetifolia</taxonomicName>
</emphasis>
</heading>
</paragraph>
<paragraph id="8BE636A4FFAAFF80DDF1FDD7620C47AE" blockId="3.[100,771,515,1484]" pageId="3" pageNumber="4">
To observe the full chemical profile of 
<taxonomicName id="4C594D27FFAAFF80DC8CFDD76370466D" box="[505,638,515,535]" class="Magnoliopsida" family="Casuarinaceae" genus="Casuarina" kingdom="Plantae" order="Fagales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="equisetifolia">
<emphasis id="B92DEAB6FFAAFF80DC8CFDD76370466D" bold="true" box="[505,638,515,535]" italics="true" pageId="3" pageNumber="4">C. equisetifolia</emphasis>
</taxonomicName>
root nodules, NMR analysis of nodule extracts was conducted. CD 
<subScript id="17DD34E1FFAAFF80DF36FDF46342464E" attach="both" box="[579,588,551,565]" fontSize="6" pageId="3" pageNumber="4">3</subScript>
OD and CDCl 
<subScript id="17DD34E1FFAAFF80DFB3FDF463C1464E" attach="left" box="[710,719,551,565]" fontSize="6" pageId="3" pageNumber="4">3</subScript>
were used in a ratio of 1:1 to extract hydrophobic compounds, while CD 
<subScript id="17DD34E1FFAAFF80DFAEFD9063EA462A" attach="right" box="[731,740,579,593]" fontSize="6" pageId="3" pageNumber="4">3</subScript>
OD and D 
<subScript id="17DD34E1FFAAFF80DDE9FD8C61AB4616" attach="both" box="[156,165,607,621]" fontSize="6" pageId="3" pageNumber="4">2</subScript>
O in ratio an of 1:1 were used to extract hydrophilic compounds. 
<superScript id="7C2C9BECFFAAFF80DD11FDBD61634607" attach="right" box="[100,109,622,636]" fontSize="6" pageId="3" pageNumber="4">1</superScript>
H-NMR spectra of root nodule extracts of 
<taxonomicName id="4C594D27FFAAFF80DC89FDA0638E46FD" box="[508,640,627,646]" class="Magnoliopsida" family="Casuarinaceae" genus="Casuarina" kingdom="Plantae" order="Fagales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="equisetifolia">
<emphasis id="B92DEAB6FFAAFF80DC89FDA0638E46FD" bold="true" box="[508,640,627,646]" italics="true" pageId="3" pageNumber="4">C. equisetifolia</emphasis>
</taxonomicName>
are shown in 
<figureCitation id="13622A21FFAAFF80DD11FD5C619746D9" box="[100,153,655,674]" captionStart="Fig" captionStartId="2.[100,130,1913,1930]" captionTargetBox="[302,1271,604,1885]" captionTargetId="figure-273@2.[305,1286,1040,1509]" captionTargetPageId="2" captionText="Fig. 2. 1H-NMR spectra of root nodule extracts of C. equisetifolia. (A) A 1H-NMR spectrum of extracts of hydrophobic compounds. (B) A 1H-NMR spectrum of extracts of hydrophilic compounds. (C) Magnified part of the 1H-NMR spectrum shown in (B). Peaks 1–6 were ascribed to tyramine, tyrosine, malate, citrate, succinate and β-glucose, respectively." figureDoi="http://doi.org/10.5281/zenodo.8276765" httpUri="https://zenodo.org/record/8276765/files/figure.png" pageId="3" pageNumber="4">Fig. 2</figureCitation>
. Comparing spectroscopic data with those of tyramine isolated in this study, signals in 
<figureCitation id="13622A21FFAAFF80DC59FD78607E46C5" box="[300,368,683,702]" captionStart="Fig" captionStartId="2.[100,130,1913,1930]" captionTargetBox="[302,1271,604,1885]" captionTargetId="figure-273@2.[305,1286,1040,1509]" captionTargetPageId="2" captionText="Fig. 2. 1H-NMR spectra of root nodule extracts of C. equisetifolia. (A) A 1H-NMR spectrum of extracts of hydrophobic compounds. (B) A 1H-NMR spectrum of extracts of hydrophilic compounds. (C) Magnified part of the 1H-NMR spectrum shown in (B). Peaks 1–6 were ascribed to tyramine, tyrosine, malate, citrate, succinate and β-glucose, respectively." figureDoi="http://doi.org/10.5281/zenodo.8276765" httpUri="https://zenodo.org/record/8276765/files/figure.png" pageId="3" pageNumber="4">Fig. 2A</figureCitation>
at 
<emphasis id="B92DEAB6FFAAFF80DCE5FD78609446C5" bold="true" box="[400,410,683,702]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
7.19 (d, 
<emphasis id="B92DEAB6FFAAFF80DC84FD7860F546C5" bold="true" box="[497,507,683,702]" italics="true" pageId="3" pageNumber="4">J</emphasis>
= 8.5 Hz), 6.92 (d, 
<emphasis id="B92DEAB6FFAAFF80DFC9FD7863C846C5" bold="true" box="[700,710,683,702]" italics="true" pageId="3" pageNumber="4">J</emphasis>
= 8.5 Hz), 3.21 (t, 
<emphasis id="B92DEAB6FFAAFF80DD90FD1461E146A1" bold="true" box="[229,239,711,730]" italics="true" pageId="3" pageNumber="4">J</emphasis>
= 7.7 Hz), and 2.98 (t, 
<emphasis id="B92DEAB6FFAAFF80DC90FD1460E146A1" bold="true" box="[485,495,711,730]" italics="true" pageId="3" pageNumber="4">J</emphasis>
= 7.7 Hz) were ascribed to tyramine. Signals at 
<emphasis id="B92DEAB6FFAAFF80DC56FD306023468D" bold="true" box="[291,301,739,758]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
7.17 (d, 
<emphasis id="B92DEAB6FFAAFF80DCF5FD306084468D" bold="true" box="[384,394,739,758]" italics="true" pageId="3" pageNumber="4">J</emphasis>
=7.9 Hz) and 6.84 (d, 
<emphasis id="B92DEAB6FFAAFF80DF10FD306361468D" bold="true" box="[613,623,739,758]" italics="true" pageId="3" pageNumber="4">J</emphasis>
=7.9 Hz) were ascribed to tyrosine (
<figureCitation id="13622A21FFAAFF80DC52FD2C60644769" box="[295,362,767,786]" captionStart="Fig" captionStartId="2.[100,130,1913,1930]" captionTargetBox="[302,1271,604,1885]" captionTargetId="figure-273@2.[305,1286,1040,1509]" captionTargetPageId="2" captionText="Fig. 2. 1H-NMR spectra of root nodule extracts of C. equisetifolia. (A) A 1H-NMR spectrum of extracts of hydrophobic compounds. (B) A 1H-NMR spectrum of extracts of hydrophilic compounds. (C) Magnified part of the 1H-NMR spectrum shown in (B). Peaks 1–6 were ascribed to tyramine, tyrosine, malate, citrate, succinate and β-glucose, respectively." figureDoi="http://doi.org/10.5281/zenodo.8276765" httpUri="https://zenodo.org/record/8276765/files/figure.png" pageId="3" pageNumber="4">Fig. 2B</figureCitation>
). Signals at 
<emphasis id="B92DEAB6FFAAFF80DCA2FD2C60EF4769" bold="true" box="[471,481,767,786]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
4.28 (dd, 
<emphasis id="B92DEAB6FFAAFF80DF4BFD2C63464769" bold="true" box="[574,584,767,786]" italics="true" pageId="3" pageNumber="4">J</emphasis>
=10.2 and 3.0 Hz), 2.67 (dd, 
<emphasis id="B92DEAB6FFAAFF80DDC8FCC861C94755" bold="true" box="[189,199,795,814]" italics="true" pageId="3" pageNumber="4">J</emphasis>
=15.3 and 3.0 Hz), and 2.36 (dd, 
<emphasis id="B92DEAB6FFAAFF80DF73FCC8631E4755" bold="true" box="[518,528,795,814]" italics="true" pageId="3" pageNumber="4">J</emphasis>
=15.3 and 10.1 Hz) were contributed to malate (
<figureCitation id="13622A21FFAAFF80DC4AFCE460884731" box="[319,390,823,842]" captionStart="Fig" captionStartId="2.[100,130,1913,1930]" captionTargetBox="[302,1271,604,1885]" captionTargetId="figure-273@2.[305,1286,1040,1509]" captionTargetPageId="2" captionText="Fig. 2. 1H-NMR spectra of root nodule extracts of C. equisetifolia. (A) A 1H-NMR spectrum of extracts of hydrophobic compounds. (B) A 1H-NMR spectrum of extracts of hydrophilic compounds. (C) Magnified part of the 1H-NMR spectrum shown in (B). Peaks 1–6 were ascribed to tyramine, tyrosine, malate, citrate, succinate and β-glucose, respectively." figureDoi="http://doi.org/10.5281/zenodo.8276765" httpUri="https://zenodo.org/record/8276765/files/figure.png" pageId="3" pageNumber="4">Fig. 2C</figureCitation>
). Signals at 
<emphasis id="B92DEAB6FFAAFF80DC8DFCE4630C4731" bold="true" box="[504,514,823,842]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
2.51 (d, 
<emphasis id="B92DEAB6FFAAFF80DF2CFCE4636D4731" bold="true" box="[601,611,823,842]" italics="true" pageId="3" pageNumber="4">J</emphasis>
= 15.5 Hz), and 2.69 (d, 
<emphasis id="B92DEAB6FFAAFF80DDC6FC8061B3471D" bold="true" box="[179,189,851,870]" italics="true" pageId="3" pageNumber="4">J</emphasis>
=15.7 Hz) were ascribed to citrate (
<figureCitation id="13622A21FFAAFF80DF60FC816355471D" box="[533,603,850,870]" captionStart="Fig" captionStartId="2.[100,130,1913,1930]" captionTargetBox="[302,1271,604,1885]" captionTargetId="figure-273@2.[305,1286,1040,1509]" captionTargetPageId="2" captionText="Fig. 2. 1H-NMR spectra of root nodule extracts of C. equisetifolia. (A) A 1H-NMR spectrum of extracts of hydrophobic compounds. (B) A 1H-NMR spectrum of extracts of hydrophilic compounds. (C) Magnified part of the 1H-NMR spectrum shown in (B). Peaks 1–6 were ascribed to tyramine, tyrosine, malate, citrate, succinate and β-glucose, respectively." figureDoi="http://doi.org/10.5281/zenodo.8276765" httpUri="https://zenodo.org/record/8276765/files/figure.png" pageId="3" pageNumber="4">Fig. 2C</figureCitation>
). Signals at 
<emphasis id="B92DEAB6FFAAFF80DFBCFC8163DD471E" bold="true" box="[713,723,850,869]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
2.41 (s), and 4.60 (d, 
<emphasis id="B92DEAB6FFAAFF80DC73FCBC601E47F9" bold="true" box="[262,272,879,898]" italics="true" pageId="3" pageNumber="4">J</emphasis>
= 7.8 Hz) were ascribed to succinate and 
<emphasis id="B92DEAB6FFAAFF80DFDFFCBC63BB47F9" bold="true" box="[682,693,879,898]" italics="true" pageId="3" pageNumber="4">β</emphasis>
-glucose (
<figureCitation id="13622A21FFAAFF80DD19FC5961BB47E6" box="[108,181,906,925]" captionStart="Fig" captionStartId="2.[100,130,1913,1930]" captionTargetBox="[302,1271,604,1885]" captionTargetId="figure-273@2.[305,1286,1040,1509]" captionTargetPageId="2" captionText="Fig. 2. 1H-NMR spectra of root nodule extracts of C. equisetifolia. (A) A 1H-NMR spectrum of extracts of hydrophobic compounds. (B) A 1H-NMR spectrum of extracts of hydrophilic compounds. (C) Magnified part of the 1H-NMR spectrum shown in (B). Peaks 1–6 were ascribed to tyramine, tyrosine, malate, citrate, succinate and β-glucose, respectively." figureDoi="http://doi.org/10.5281/zenodo.8276765" httpUri="https://zenodo.org/record/8276765/files/figure.png" pageId="3" pageNumber="4">Fig. 2C</figureCitation>
), respectively. The identification of tyrosine, malate, citrate, succinate and 
<emphasis id="B92DEAB6FFAAFF80DD9BFC7461F747C1" bold="true" box="[238,249,935,954]" italics="true" pageId="3" pageNumber="4">β</emphasis>
-glucose was developed through comparing their spectroscopic data with literature values (
<bibRefCitation id="EFC84B55FFAAFF80DCB3FC11635047AE" author="Kim, H. K. &amp; Choi, Y. H. &amp; Verpoorte, R." box="[454,606,962,981]" pageId="3" pageNumber="4" pagination="536 - 549" refId="ref7158" refString="Kim, H. K., Choi, Y. H., Verpoorte, R., 2010. NMR-based metabolomic analysis of plants. Nat. Protoc. 5, 536 - 549. https: // doi. org / 10.1038 / nprot. 2009.237." type="journal article" year="2010">Kim et al., 2010</bibRefCitation>
; 
<bibRefCitation id="EFC84B55FFAAFF80DF1CFC1163FA47AE" author="Xu, Y. &amp; Tao, Z. &amp; Jin, Y. &amp; Chen, S. &amp; Zhou, Z. - Y. &amp; Gong, A. G. &amp; Yuan, Y. &amp; Dong, T. T. &amp; Tsim, K. W." box="[617,756,962,981]" pageId="3" pageNumber="4" pagination="188" refId="ref8368" refString="Xu, Y., Tao, Z., Jin, Y., Chen, S., Zhou, Z. - Y., Gong, A. G., Yuan, Y., Dong, T. T., Tsim, K. W., 2018. Jasmonate-elicited stress induces metabolic change in the leaves of Leucaena leucocephala. Molecules 23, 188." type="journal article" year="2018">Xu et al., 2018</bibRefCitation>
).
</paragraph>
<paragraph id="8BE636A4FFAAFF80DDF1FC0D60B841E8" blockId="3.[100,771,515,1484]" pageId="3" pageNumber="4">
The same amount root nodule powder was used for the extraction of hydrophobic compounds (see 
<figureCitation id="13622A21FFAAFF80DC09FC2960CC4076" box="[380,450,1018,1037]" captionStart="Fig" captionStartId="2.[100,130,1913,1930]" captionTargetBox="[302,1271,604,1885]" captionTargetId="figure-273@2.[305,1286,1040,1509]" captionTargetPageId="2" captionText="Fig. 2. 1H-NMR spectra of root nodule extracts of C. equisetifolia. (A) A 1H-NMR spectrum of extracts of hydrophobic compounds. (B) A 1H-NMR spectrum of extracts of hydrophilic compounds. (C) Magnified part of the 1H-NMR spectrum shown in (B). Peaks 1–6 were ascribed to tyramine, tyrosine, malate, citrate, succinate and β-glucose, respectively." figureDoi="http://doi.org/10.5281/zenodo.8276765" httpUri="https://zenodo.org/record/8276765/files/figure.png" pageId="3" pageNumber="4">Fig. 2A</figureCitation>
), and hydrophilic compounds (see 
<figureCitation id="13622A21FFAAFF80DD11FBC561A04052" box="[100,174,1046,1065]" captionStart="Fig" captionStartId="2.[100,130,1913,1930]" captionTargetBox="[302,1271,604,1885]" captionTargetId="figure-273@2.[305,1286,1040,1509]" captionTargetPageId="2" captionText="Fig. 2. 1H-NMR spectra of root nodule extracts of C. equisetifolia. (A) A 1H-NMR spectrum of extracts of hydrophobic compounds. (B) A 1H-NMR spectrum of extracts of hydrophilic compounds. (C) Magnified part of the 1H-NMR spectrum shown in (B). Peaks 1–6 were ascribed to tyramine, tyrosine, malate, citrate, succinate and β-glucose, respectively." figureDoi="http://doi.org/10.5281/zenodo.8276765" httpUri="https://zenodo.org/record/8276765/files/figure.png" pageId="3" pageNumber="4">Fig. 2B</figureCitation>
). Tyramine was the most abundant component observed in 
<figureCitation id="13622A21FFAAFF80DD11FBE161A2403E" box="[100,172,1074,1093]" captionStart="Fig" captionStartId="2.[100,130,1913,1930]" captionTargetBox="[302,1271,604,1885]" captionTargetId="figure-273@2.[305,1286,1040,1509]" captionTargetPageId="2" captionText="Fig. 2. 1H-NMR spectra of root nodule extracts of C. equisetifolia. (A) A 1H-NMR spectrum of extracts of hydrophobic compounds. (B) A 1H-NMR spectrum of extracts of hydrophilic compounds. (C) Magnified part of the 1H-NMR spectrum shown in (B). Peaks 1–6 were ascribed to tyramine, tyrosine, malate, citrate, succinate and β-glucose, respectively." figureDoi="http://doi.org/10.5281/zenodo.8276765" httpUri="https://zenodo.org/record/8276765/files/figure.png" pageId="3" pageNumber="4">Fig. 2A</figureCitation>
. Tyrosine was the next most abundant component observed in 
<figureCitation id="13622A21FFAAFF80DD11FB9D61A7401A" box="[100,169,1102,1121]" captionStart="Fig" captionStartId="2.[100,130,1913,1930]" captionTargetBox="[302,1271,604,1885]" captionTargetId="figure-273@2.[305,1286,1040,1509]" captionTargetPageId="2" captionText="Fig. 2. 1H-NMR spectra of root nodule extracts of C. equisetifolia. (A) A 1H-NMR spectrum of extracts of hydrophobic compounds. (B) A 1H-NMR spectrum of extracts of hydrophilic compounds. (C) Magnified part of the 1H-NMR spectrum shown in (B). Peaks 1–6 were ascribed to tyramine, tyrosine, malate, citrate, succinate and β-glucose, respectively." figureDoi="http://doi.org/10.5281/zenodo.8276765" httpUri="https://zenodo.org/record/8276765/files/figure.png" pageId="3" pageNumber="4">Fig. 2B</figureCitation>
, while malate, citrate, succinate and 
<emphasis id="B92DEAB6FFAAFF80DF7DFB9D631D401A" bold="true" box="[520,531,1102,1121]" italics="true" pageId="3" pageNumber="4">β</emphasis>
-glucose were detected at low levels in 
<figureCitation id="13622A21FFAAFF80DD97FBBA60264006" box="[226,296,1129,1149]" captionStart="Fig" captionStartId="2.[100,130,1913,1930]" captionTargetBox="[302,1271,604,1885]" captionTargetId="figure-273@2.[305,1286,1040,1509]" captionTargetPageId="2" captionText="Fig. 2. 1H-NMR spectra of root nodule extracts of C. equisetifolia. (A) A 1H-NMR spectrum of extracts of hydrophobic compounds. (B) A 1H-NMR spectrum of extracts of hydrophilic compounds. (C) Magnified part of the 1H-NMR spectrum shown in (B). Peaks 1–6 were ascribed to tyramine, tyrosine, malate, citrate, succinate and β-glucose, respectively." figureDoi="http://doi.org/10.5281/zenodo.8276765" httpUri="https://zenodo.org/record/8276765/files/figure.png" pageId="3" pageNumber="4">Fig. 2C</figureCitation>
. The tyramine contents in different 
<taxonomicName id="4C594D27FFAAFF80DF0BFBBA61AB40E2" class="Magnoliopsida" family="Casuarinaceae" genus="Casuarina" kingdom="Plantae" order="Fagales" pageId="3" pageNumber="5" phylum="Tracheophyta" rank="subSpecies" species="equisetifolia" subSpecies="organs">
<emphasis id="B92DEAB6FFAAFF80DF0BFBBA620C4007" bold="true" box="[638,770,1129,1148]" italics="true" pageId="3" pageNumber="4">C. equisetifolia</emphasis>
organs
</taxonomicName>
, including roots, stems, leaves, seeds, and mature as well as senescent root nodules, were evaluated by high-performance liquid chromatography (HPLC). The results are shown in 
<figureCitation id="13622A21FFAAFF80DF2AFB6E639640AB" box="[607,664,1213,1232]" captionStart="Fig" captionStartId="3.[100,130,1939,1956]" captionTargetBox="[118,753,1524,1911]" captionTargetId="graphics-1016@3.[118,753,1524,1911]" captionTargetPageId="3" captionText="Fig. 3. The contents of tyramine in various organs of C. equisetifolia. Values are in mean ± SD, where n = 3." figureDoi="http://doi.org/10.5281/zenodo.8276769" httpUri="https://zenodo.org/record/8276769/files/figure.png" pageId="3" pageNumber="4">Fig. 3</figureCitation>
. Tyramine levels varied greatly among the different organs. Notably, tyramine was specifically enriched in roots and root nodules, especially in mature nodules (2.760 ± 
<quantity id="4CA19B41FFAAFF80DC69FAC26073415F" box="[284,381,1297,1316]" metricMagnitude="-7" metricUnit="kg" metricValue="3.15" pageId="3" pageNumber="4" unit="mg" value="0.315">0.315 mg</quantity>
/g fresh weight (FW)). The contents of tyramine in roots and senescent nodules were 0.837 ± 
<quantity id="4CA19B41FFAAFF80DF18FAFE63C7413B" box="[621,713,1325,1344]" metricMagnitude="-8" metricUnit="kg" metricValue="9.8" pageId="3" pageNumber="4" unit="mg" value="0.098">0.098 mg</quantity>
/g FW and 0.070 ± 
<quantity id="4CA19B41FFAAFF80DDA9FA9A60384127" box="[220,310,1353,1372]" metricMagnitude="-9" metricUnit="kg" metricValue="8.0" pageId="3" pageNumber="4" unit="mg" value="0.008">0.008 mg</quantity>
/g FW, respectively. In contrast, tyramine was not detected in stems, leaves, and seeds. Therefore, tyramine was an abundant component in mature nodules.
</paragraph>
<paragraph id="8BE636A4FFAAFF80DDF1FA4E65C146AE" blockId="3.[100,771,515,1484]" lastBlockId="3.[818,1491,147,725]" pageId="3" pageNumber="4">
It has been reported that tyramine can function as carbon and nitrogen sources in bacteria, such as 
<taxonomicName id="4C594D27FFAAFF80DCD3FA6B63D441B0" authority="(Diaz et al., 2001)" baseAuthorityName="Diaz" baseAuthorityYear="2001" box="[422,730,1464,1484]" class="Gammaproteobacteria" family="Enterobacteriaceae" genus="Escherichia" kingdom="Bacteria" order="Enterobacteriales" pageId="3" pageNumber="4" phylum="Proteobacteria" rank="species" species="coli">
<emphasis id="B92DEAB6FFAAFF80DCD3FA6B632041B0" bold="true" box="[422,558,1464,1483]" italics="true" pageId="3" pageNumber="4">Escherichia coli</emphasis>
(
<bibRefCitation id="EFC84B55FFAAFF80DF4EFA6B63DC41B0" author="Diaz, E. &amp; Ferrandez, A. &amp; Prieto, M. A. &amp; Garcia, J. L." box="[571,722,1464,1484]" pageId="3" pageNumber="4" pagination="523 - 569" refId="ref6540" refString="Diaz, E., Ferrandez, A., Prieto, M. A., Garcia, J. L., 2001. Biodegradation of aromatic compounds by Escherichia coli. Microbiol. Mol. Biol. Rev. 65, 523 - 569. https: // doi. org / 10.1128 / MMBR. 65.4.523 - 569.2001." type="journal article" year="2001">Diaz et al., 2001</bibRefCitation>
)
</taxonomicName>
and 
<taxonomicName id="4C594D27FFAAFF80DE47FF4065BE44DC" authority="(Chistoserdov, 2001)" baseAuthorityName="Chistoserdov" baseAuthorityYear="2001" box="[818,1200,147,167]" class="Gammaproteobacteria" family="Halomonadaceae" genus="Alcaligenes" kingdom="Bacteria" order="Oceanospirillales" pageId="3" pageNumber="4" phylum="Proteobacteria" rank="species" species="faecalis">
<emphasis id="B92DEAB6FFAAFF80DE47FF4062D144DD" bold="true" box="[818,991,147,166]" italics="true" pageId="3" pageNumber="4">Alcaligenes faecalis</emphasis>
(
<bibRefCitation id="EFC84B55FFAAFF80DE9AFF4765A844DC" author="Chistoserdov, A. Y." box="[1007,1190,148,167]" pageId="3" pageNumber="4" pagination="2195 - 2202" refId="ref6304" refString="Chistoserdov, A. Y., 2001. Cloning, sequencing and mutagenesis of the genes for aromatic amine dehydrogenase from Alcaligenes faecalis and evolution of amine dehydrogenases. Microbiol-sgm. 147, 2195 - 2202. https: // doi. org / 10.1099 / 00221287 - 147 - 8 - 2195." type="journal article" year="2001">Chistoserdov, 2001</bibRefCitation>
)
</taxonomicName>
. Thus, tyramine might play a role as carbon and nitrogen source in 
<taxonomicName id="4C594D27FFAAFF80D9E6FF7C65D644B9" authorityName="Brunchorst" authorityYear="1886" box="[1171,1240,175,194]" class="Magnoliopsida" family="Asteraceae" genus="Frankia" kingdom="Plantae" order="Asterales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="genus">
<emphasis id="B92DEAB6FFAAFF80D9E6FF7C65D644B9" bold="true" box="[1171,1240,175,194]" italics="true" pageId="3" pageNumber="4">Frankia</emphasis>
</taxonomicName>
. Growth curves of 
<taxonomicName id="4C594D27FFAAFF80D8FFFF7C629C44A5" class="Magnoliopsida" family="Asteraceae" genus="Frankia" kingdom="Plantae" order="Asterales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="casuarinae">
<emphasis id="B92DEAB6FFAAFF80D8FFFF7C629C44A5" bold="true" italics="true" pageId="3" pageNumber="4">Frankia casuarinae</emphasis>
</taxonomicName>
strain CcI 
<quantity id="4CA19B41FFAAFF80DE82FF1F651744A5" box="[1015,1049,203,223]" metricMagnitude="-2" metricUnit="m" metricValue="7.62" pageId="3" pageNumber="4" unit="in" value="3.0">3 in</quantity>
BAP medium, BAP medium without nitrogen source (BAP N–), BAP medium without neither carbon nor nitrogen source (BAP C– N–) but containing 1.875 mM tyramine (BAP C– N– + tyramine), BAP C– N– medium containing 3.75 mM malate (BAP C– N– +malate), and BAP N– medium containing 5 mM tyramine (BAP N– + tyramine) are shown in 
<figureCitation id="13622A21FFAAFF80D97AFE84654D4511" box="[1039,1091,343,362]" captionStart="Fig" captionStartId="3.[818,848,1760,1777]" captionTargetBox="[838,1415,1412,1729]" captionTargetId="graphics-1232@3.[904,1206,1419,1688]" captionTargetPageId="3" captionText="Fig. 4. Growth of Frankia casuarinae strain CcI3 in BAP media with various carbon and nitrogen sources. BAP, containing 5 mM Na propionate (15 mM carbon units) as carbon source and 5 mM ammonium chloride (5 mM nitrogen units) as nitrogen source; BAP N–, BAP medium without nitrogen source; BAP C– N–, BAP medium without neither carbon nor nitrogen source; BAP C– N– + tyramine, BAP C– N– medium containing 1.875 mM tyramine (15 mM carbon units); BAP C– N– + malate, BAP C– N– medium containing 3.75 mM malate (15 mM carbon units); BAP N– + tyramine, BAP N– medium containing 5 mM tyramine (5 mM nitrogen units)." figureDoi="http://doi.org/10.5281/zenodo.8276767" httpUri="https://zenodo.org/record/8276767/files/figure.png" pageId="3" pageNumber="4">Fig. 4</figureCitation>
. 
<taxonomicName id="4C594D27FFAAFF80D938FE84659C4511" authorityName="Brunchorst" authorityYear="1886" box="[1101,1170,343,362]" class="Magnoliopsida" family="Asteraceae" genus="Frankia" kingdom="Plantae" order="Asterales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="genus">
<emphasis id="B92DEAB6FFAAFF80D938FE84659C4511" bold="true" box="[1101,1170,343,362]" italics="true" pageId="3" pageNumber="4">Frankia</emphasis>
</taxonomicName>
strain CcI3 grew well in both BAP and BAP N– media, while it could not grow on tyramine as sole carbon and nitrogen source. Therefore, tyramine cannot function as sole carbon and nitrogen source in 
<taxonomicName id="4C594D27FFAAFF80D962FE79655245C6" authorityName="Brunchorst" authorityYear="1886" box="[1047,1116,426,445]" class="Magnoliopsida" family="Asteraceae" genus="Frankia" kingdom="Plantae" order="Asterales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="genus">
<emphasis id="B92DEAB6FFAAFF80D962FE79655245C6" bold="true" box="[1047,1116,426,445]" italics="true" pageId="3" pageNumber="4">Frankia</emphasis>
</taxonomicName>
strain CcI3. For comparison, a tricarboxylic acid cycle intermediate, malate was also examined. 
<taxonomicName id="4C594D27FFAAFF80D82FFE1464C145A2" box="[1370,1487,454,474]" class="Magnoliopsida" family="Asteraceae" genus="Frankia" kingdom="Plantae" order="Asterales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="casuarinae">
<emphasis id="B92DEAB6FFAAFF80D82FFE1464C145A2" bold="true" box="[1370,1487,454,474]" italics="true" pageId="3" pageNumber="4">F. casuarinae</emphasis>
</taxonomicName>
strain CcI3 could grow on propionate, but not on malate as sole carbon source under nitrogen-fixing conditions. Notably, the 
<taxonomicName id="4C594D27FFAAFF80D857FE2D6469466A" authorityName="Brunchorst" authorityYear="1886" box="[1314,1383,510,529]" class="Magnoliopsida" family="Asteraceae" genus="Frankia" kingdom="Plantae" order="Asterales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="genus">
<emphasis id="B92DEAB6FFAAFF80D857FE2D6469466A" bold="true" box="[1314,1383,510,529]" italics="true" pageId="3" pageNumber="4">Frankia</emphasis>
</taxonomicName>
strain CcI3 grew well in BAP N– medium. However, it could not grow in BAP N– + tyramine. Tyramine seemed to be a growth inhibitor in free-living 
<taxonomicName id="4C594D27FFAAFF80DE47FD816279461E" authorityName="Brunchorst" authorityYear="1886" box="[818,887,594,613]" class="Magnoliopsida" family="Asteraceae" genus="Frankia" kingdom="Plantae" order="Asterales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="genus">
<emphasis id="B92DEAB6FFAAFF80DE47FD816279461E" bold="true" box="[818,887,594,613]" italics="true" pageId="3" pageNumber="4">Frankia</emphasis>
</taxonomicName>
strain CcI3. Whether tyramine is also toxic to the growth of 
<taxonomicName id="4C594D27FFAAFF80DE47FDBD627946FA" authorityName="Brunchorst" authorityYear="1886" box="[818,887,622,641]" class="Magnoliopsida" family="Asteraceae" genus="Frankia" kingdom="Plantae" order="Asterales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="genus">
<emphasis id="B92DEAB6FFAAFF80DE47FDBD627946FA" bold="true" box="[818,887,622,641]" italics="true" pageId="3" pageNumber="4">Frankia</emphasis>
</taxonomicName>
strain in actinorhizal nodules, it remains unknown. It has been reported that tyramine is toxic to tobacco (
<taxonomicName id="4C594D27FFAAFF80D9BFFD59647D46E7" box="[1226,1395,649,669]" class="Magnoliopsida" family="Solanaceae" genus="Nicotiana" kingdom="Plantae" order="Solanales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="tabacum">
<emphasis id="B92DEAB6FFAAFF80D9BFFD59647D46E7" bold="true" box="[1226,1395,649,669]" italics="true" pageId="3" pageNumber="4">Nicotiana tabacum</emphasis>
</taxonomicName>
L.) callus cultures grown in the presence of auxins, whereas it is not toxic in the presence of cytokinins (
<bibRefCitation id="EFC84B55FFAAFF80D967FD1265CC46AE" author="Negrel, J. &amp; Javelle, F. &amp; Paynot, M." box="[1042,1218,705,725]" pageId="3" pageNumber="4" pagination="329 - 334" refId="ref7614" refString="Negrel, J., Javelle, F., Paynot, M., 1993. Biochemical basis of resistance of tobacco callustissue cultures to hydroxyphenylethylamines. Plant Physiol. 103, 329 - 334. https: // doi. org / 10.1104 / pp. 103.2.329." type="journal article" year="1993">Negrel et al., 1993</bibRefCitation>
).
</paragraph>
</subSubSection>
</treatment>
</document>