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<document id="5D354AC87121C1C510FFD05A6A733086" ID-DOI="10.1016/j.phytochem.2018.07.014" ID-ISSN="1873-3700" ID-Zenodo-Dep="10484408" IM.bibliography_approvedBy="felipe" IM.illustrations_approvedBy="felipe" IM.materialsCitations_approvedBy="juliana" IM.metadata_approvedBy="juliana" IM.taxonomicNames_approvedBy="juliana" IM.treatments_approvedBy="juliana" checkinTime="1704940826861" checkinUser="felipe" docAuthor="Yoshikawa, Mayu, Luo, Weifeng, Tanaka, Genta, Konishi, Yuka, Matsuura, Hideyuki &amp; Takahashi, Kosaku" docDate="2018" docId="972487969347FF9AFFE3AC8AB0A7F8BB" docLanguage="en" docName="Phytochemistry.155.30-36.pdf" docOrigin="Phytochemistry 155" docSource="http://dx.doi.org/10.1016/j.phytochem.2018.07.014" docStyle="DocumentStyle:9E596C34F4E94307D29315B03ACE1007.6:Phytochemistry.2014-2019.journal_article" docStyleId="9E596C34F4E94307D29315B03ACE1007" docStyleName="Phytochemistry.2014-2019.journal_article" docStyleVersion="6" docTitle="Marchantia polymorpha L" docType="treatment" docVersion="4" lastPageNumber="32" masterDocId="6B1DFFEE9345FF98FF87A97CB343FFA5" masterDocTitle="Wounding stress induces phenylalanine ammonia lyases, leading to the accumulation of phenylpropanoids in the model liverwort Marchantia polymorpha" masterLastPageNumber="36" masterPageNumber="30" pageNumber="32" updateTime="1705336639647" updateUser="juliana">
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<mods:title id="D88B52F9B10CF8EC37A21E3BBC37E235">Wounding stress induces phenylalanine ammonia lyases, leading to the accumulation of phenylpropanoids in the model liverwort Marchantia polymorpha</mods:title>
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<mods:namePart id="57F618A4258F0A92817C40535363DE1F">Yoshikawa, Mayu</mods:namePart>
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<mods:namePart id="2246C2B167D854B3D7C840964D7A1405">Luo, Weifeng</mods:namePart>
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<mods:namePart id="BD134D45930DFF91971989091DB85CCF">Tanaka, Genta</mods:namePart>
<mods:affiliation id="878A0AF3F8FA138C57E50CC3F13CE862">Research Faculty of Agriculture, Hokkaido University, Sapporo, 060 - 8589, Japan</mods:affiliation>
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<mods:namePart id="366EC4FA5B72ACF1B67070D79E6FCEB6">Konishi, Yuka</mods:namePart>
<mods:affiliation id="2A9E31522D7F0D6C97EE96716315F270">Research Faculty of Agriculture, Hokkaido University, Sapporo, 060 - 8589, Japan</mods:affiliation>
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<mods:namePart id="61797177FF35CCC10CFEA73BE1245948">Takahashi, Kosaku</mods:namePart>
<mods:affiliation id="8E3A0020C1D98FA8FC063C990C852AA0">Research Faculty of Agriculture, Hokkaido University, Sapporo, 060 - 8589, Japan</mods:affiliation>
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2.3. Phenylalanine ammonia lyases in
<taxonomicName id="D88D4D039347FF9AFE43AC8AB10FF9AC" ID-CoL="3Y2XL" authority="L" authorityName="L" box="[452,588,1526,1545]" class="Marchantiopsida" family="Marchantiaceae" genus="Marchantia" kingdom="Plantae" order="Marchantiales" pageId="2" pageNumber="32" phylum="Marchantiophyta" rank="species" species="polymorpha">M. polymorpha</taxonomicName>
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Flavonoids and bisbibenzyls are categorized as phenylpropanoids, and the initial step in the biosynthesis of compounds
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is a PAL reaction, the non-oxidative deamination of phenylalanine to
<emphasis id="2DF9EA929347FF9AFD2CAF1AB194F9DC" bold="true" box="[683,727,1638,1657]" italics="true" pageId="2" pageNumber="32">trans</emphasis>
-cinnamic acid (
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). PALs have been extensively studied with respect to the production of natural products such as flavonoids, lignin, and a variety of other phenolic compounds in plants. However, no detailed studies of PAL activity in
<taxonomicName id="D88D4D039347FF9AFE20AFA9B16CF94D" box="[423,559,1749,1768]" class="Marchantiopsida" family="Marchantiaceae" genus="Marchantia" kingdom="Plantae" order="Marchantiales" pageId="2" pageNumber="32" phylum="Marchantiophyta" rank="species" species="polymorpha">
<emphasis id="2DF9EA929347FF9AFE20AFA9B16CF94D" bold="true" box="[423,559,1749,1768]" italics="true" pageId="2" pageNumber="32">M. polymorpha</emphasis>
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have been conducted.
</paragraph>
<paragraph id="1F3236809347FF9AFF02AF8DB603FAE1" blockId="2.[100,771,1582,1992]" lastBlockId="2.[818,1488,1106,1822]" pageId="2" pageNumber="32">
Genomic analysis predicted the presence of ten Mp
<emphasis id="2DF9EA929347FF9AFDEEAF8DB1CDF8A1" bold="true" box="[617,654,1777,1796]" italics="true" pageId="2" pageNumber="32">PAL</emphasis>
genes in
<taxonomicName id="D88D4D039347FF9AFD6EAF8DB2FBF885" authority="(Bowman et al., 2017)" baseAuthorityName="Bowman" baseAuthorityYear="2017" class="Marchantiopsida" family="Marchantiaceae" genus="Marchantia" kingdom="Plantae" order="Marchantiales" pageId="2" pageNumber="32" phylum="Marchantiophyta" rank="species" species="polymorpha">
<emphasis id="2DF9EA929347FF9AFD6EAF8DB38EF885" bold="true" italics="true" pageId="2" pageNumber="32">M. polymorpha</emphasis>
(
<bibRefCitation id="7B1C4B719347FF9AFF67AE71B2ECF885" author="Bowman, J. L. &amp; Kohchi, T. &amp; Yamato, K. T. &amp; Jenkins, J. &amp; Shu, S. &amp; Ishizaki, K. &amp; Yamaoka, S. &amp; Nishihama, R. &amp; Nakamura, Y. &amp; Berger, F. &amp; Adam, C. &amp; Aki, S. S. &amp; Araki, T. &amp; Arteaga-Vazquez, M. A. &amp; Balasubrmanian, S. &amp; Barry, K. &amp; Bauer, D. &amp; Boehm, C. R. &amp; Briginshaw, L. &amp; Caballero-Perez, J. &amp; Catarino, B. &amp; Chen, F. &amp; Chiyoda, S. &amp; Chovatia, M. &amp; Davies, K. M. &amp; Delmans, M. &amp; Demura, T. &amp; Dierschke, T. &amp; Dolan, L. &amp; Dorantes-Acosta, A. E. &amp; Eklund, D. M. &amp; Florent, S. N. &amp; Flores-Sandoval, E. &amp; Fujiyama, A. &amp; Fukuzawa, H. &amp; Galik, B. &amp; Grimanelli, D. &amp; Grimwood, J. &amp; Grossniklaus, U. &amp; Hamada, T. &amp; Haseloff, J. &amp; Hetherington, A. J. &amp; Higo, A. &amp; Hirakawa, Y. &amp; Hundley, H. N. &amp; Ikeda, Y. &amp; Inoue, K. &amp; Inoue, S. I. &amp; Ishida, S. &amp; Jia, Q. &amp; Kakita, M. &amp; Kanazawa, T. &amp; Kawai, Y. &amp; Kawashima, T. &amp; Kennedy, M. &amp; Kinose, K. &amp; Kinoshita, T. &amp; Kohara, Y. &amp; Koide, E. &amp; Komatsu, K. &amp; Kopischke, S. &amp; Kubo, M. &amp; Kyozuka, J. &amp; Lagercrantz, U. &amp; Lin, S. S. &amp; Lindquist, E. &amp; Lipzen, A. M. &amp; Lu, C. W. &amp; De Luna, E. &amp; Martienssen, R. A. &amp; Minamino, N. &amp; Mizutani, M. &amp; Mizutani, M. &amp; Mochizuki, N. &amp; Monte, I. &amp; Mosher, R. &amp; Nagasaki, H. &amp; Nakagami, H. &amp; Naramoto, S. &amp; Nishitani, K. &amp; Ohtani, M. &amp; Okamoto, T. &amp; Okumura, M. &amp; Phillips, J. &amp; Pollak, B. &amp; Reinders, A. &amp; Rovekamp, M. &amp; Sano, R. &amp; Sawa, S. &amp; Schmid, M. W. &amp; Shirakawa, M. &amp; Solano, R. &amp; Spunde, A. &amp; Suetsugu, N. &amp; Sugano, S. &amp; Sugiyama, A. &amp; Sun, R. &amp; Suzuki, Y. &amp; Takenaka, M. &amp; Takezawa, D. &amp; Tomogane, H. &amp; Tsuzuki, M. &amp; Ueda, T. &amp; Umeda, M. &amp; Ward, J. M. &amp; Watanabe, Y. &amp; Yazaki, K. &amp; Yokoyama, R. &amp; Yoshitake, Y. &amp; Yotsui, I. &amp; Zachgo, S. &amp; Schmutz, J." box="[224,431,1805,1824]" pageId="2" pageNumber="32" pagination="287 - 304" refId="ref6849" refString="Bowman, J. L., Kohchi, T., Yamato, K. T., Jenkins, J., Shu, S., Ishizaki, K., Yamaoka, S., Nishihama, R., Nakamura, Y., Berger, F., Adam, C., Aki, S. S., Althoff, Fl, Araki, T., Arteaga-Vazquez, M. A., Balasubrmanian, S., Barry, K., Bauer, D., Boehm, C. R., Briginshaw, L., Caballero-Perez, J., Catarino, B., Chen, F., Chiyoda, S., Chovatia, M., Davies, K. M., Delmans, M., Demura, T., Dierschke, T., Dolan, L., Dorantes-Acosta, A. E., Eklund, D. M., Florent, S. N., Flores-Sandoval, E., Fujiyama, A., Fukuzawa, H., Galik, B., Grimanelli, D., Grimwood, J., Grossniklaus, U., Hamada, T., Haseloff, J., Hetherington, A. J., Higo, A., Hirakawa, Y., Hundley, H. N., Ikeda, Y., Inoue, K., Inoue, S. I., Ishida, S., Jia, Q., Kakita, M., Kanazawa, T., Kawai, Y., Kawashima, T., Kennedy, M., Kinose, K., Kinoshita, T., Kohara, Y., Koide, E., Komatsu, K., Kopischke, S., Kubo, M., Kyozuka, J., Lagercrantz, U., Lin, S. S., Lindquist, E., Lipzen, A. M., Lu, C. W., De Luna, E., Martienssen, R. A., Minamino, N., Mizutani, M., Mizutani, M., Mochizuki, N., Monte, I., Mosher, R., Nagasaki, H., Nakagami, H., Naramoto, S., Nishitani, K., Ohtani, M., Okamoto, T., Okumura, M., Phillips, J., Pollak, B., Reinders, A., Rovekamp, M., Sano, R., Sawa, S., Schmid, M. W., Shirakawa, M., Solano, R., Spunde, A., Suetsugu, N., Sugano, S., Sugiyama, A., Sun, R., Suzuki, Y., Takenaka, M., Takezawa, D., Tomogane, H., Tsuzuki, M., Ueda, T., Umeda, M., Ward, J. M., Watanabe, Y., Yazaki, K., Yokoyama, R., Yoshitake, Y., Yotsui, I., Zachgo, S., Schmutz, J., 2017. Insights into land plant evolution garnered from the Marchantia polymorpha genome. Cell 171, 287 - 304." type="journal article" year="2017">Bowman et al., 2017</bibRefCitation>
)
</taxonomicName>
, which were designated Mp
<emphasis id="2DF9EA929347FF9AFD56AE71B041F885" bold="true" box="[721,770,1805,1824]" italics="true" pageId="2" pageNumber="32">PAL1</emphasis>
(Mapoly0014s0211.1), Mp
<emphasis id="2DF9EA929347FF9AFEE4AE55B2D7F899" bold="true" box="[355,404,1833,1852]" italics="true" pageId="2" pageNumber="32">PAL2</emphasis>
(Mapoly0044s0114.1), Mp
<emphasis id="2DF9EA929347FF9AFD1CAE55B18FF899" bold="true" box="[667,716,1833,1852]" italics="true" pageId="2" pageNumber="32">PAL3</emphasis>
(Mapoly0009s0173.1), Mp
<emphasis id="2DF9EA929347FF9AFEC1AE39B23BF8FD" bold="true" box="[326,376,1861,1880]" italics="true" pageId="2" pageNumber="32">PAL4</emphasis>
(Mapoly0070s0061.1), Mp
<emphasis id="2DF9EA929347FF9AFD15AE39B181F8FD" bold="true" box="[658,706,1861,1880]" italics="true" pageId="2" pageNumber="32">PAL5</emphasis>
(Mapoly0070s0065.1), Mp
<emphasis id="2DF9EA929347FF9AFEC1AE1DB23BF8D1" bold="true" box="[326,376,1889,1908]" italics="true" pageId="2" pageNumber="32">PAL6</emphasis>
(Mapoly0070s0068.1), Mp
<emphasis id="2DF9EA929347FF9AFD15AE1DB180F8D1" bold="true" box="[658,707,1889,1908]" italics="true" pageId="2" pageNumber="32">PAL7</emphasis>
(Mapoly0070s0071.1), Mp
<emphasis id="2DF9EA929347FF9AFEDCAE01B2CFF835" bold="true" box="[347,396,1917,1936]" italics="true" pageId="2" pageNumber="32">PAL8</emphasis>
(Mapoly0132s0049.1), Mp
<emphasis id="2DF9EA929347FF9AFD56AE01B041F835" bold="true" box="[721,770,1917,1936]" italics="true" pageId="2" pageNumber="32">PAL9</emphasis>
(Mapoly0005s0086.1), and Mp
<emphasis id="2DF9EA929347FF9AFE00AEE5B287F809" bold="true" box="[391,452,1945,1964]" italics="true" pageId="2" pageNumber="32">PAL10</emphasis>
(Mapoly0005s0089.1). Similar to
<taxonomicName id="D88D4D039347FF9AFFE3AEC9B3B6F86D" box="[100,245,1973,1992]" class="Marchantiopsida" family="Marchantiaceae" genus="Marchantia" kingdom="Plantae" order="Marchantiales" pageId="2" pageNumber="32" phylum="Marchantiophyta" rank="species" species="polymorpha">
<emphasis id="2DF9EA929347FF9AFFE3AEC9B3B6F86D" bold="true" box="[100,245,1973,1992]" italics="true" pageId="2" pageNumber="32">M. polymorpha</emphasis>
</taxonomicName>
, other land plants also have multiple
<emphasis id="2DF9EA929347FF9AFD1EAEC9B1FDF86D" bold="true" box="[665,702,1973,1992]" italics="true" pageId="2" pageNumber="32">PAL</emphasis>
genes (
<bibRefCitation id="7B1C4B719347FF9AFCBDAD2EB747FBC0" author="Bowman, J. L. &amp; Kohchi, T. &amp; Yamato, K. T. &amp; Jenkins, J. &amp; Shu, S. &amp; Ishizaki, K. &amp; Yamaoka, S. &amp; Nishihama, R. &amp; Nakamura, Y. &amp; Berger, F. &amp; Adam, C. &amp; Aki, S. S. &amp; Araki, T. &amp; Arteaga-Vazquez, M. A. &amp; Balasubrmanian, S. &amp; Barry, K. &amp; Bauer, D. &amp; Boehm, C. R. &amp; Briginshaw, L. &amp; Caballero-Perez, J. &amp; Catarino, B. &amp; Chen, F. &amp; Chiyoda, S. &amp; Chovatia, M. &amp; Davies, K. M. &amp; Delmans, M. &amp; Demura, T. &amp; Dierschke, T. &amp; Dolan, L. &amp; Dorantes-Acosta, A. E. &amp; Eklund, D. M. &amp; Florent, S. N. &amp; Flores-Sandoval, E. &amp; Fujiyama, A. &amp; Fukuzawa, H. &amp; Galik, B. &amp; Grimanelli, D. &amp; Grimwood, J. &amp; Grossniklaus, U. &amp; Hamada, T. &amp; Haseloff, J. &amp; Hetherington, A. J. &amp; Higo, A. &amp; Hirakawa, Y. &amp; Hundley, H. N. &amp; Ikeda, Y. &amp; Inoue, K. &amp; Inoue, S. I. &amp; Ishida, S. &amp; Jia, Q. &amp; Kakita, M. &amp; Kanazawa, T. &amp; Kawai, Y. &amp; Kawashima, T. &amp; Kennedy, M. &amp; Kinose, K. &amp; Kinoshita, T. &amp; Kohara, Y. &amp; Koide, E. &amp; Komatsu, K. &amp; Kopischke, S. &amp; Kubo, M. &amp; Kyozuka, J. &amp; Lagercrantz, U. &amp; Lin, S. S. &amp; Lindquist, E. &amp; Lipzen, A. M. &amp; Lu, C. W. &amp; De Luna, E. &amp; Martienssen, R. A. &amp; Minamino, N. &amp; Mizutani, M. &amp; Mizutani, M. &amp; Mochizuki, N. &amp; Monte, I. &amp; Mosher, R. &amp; Nagasaki, H. &amp; Nakagami, H. &amp; Naramoto, S. &amp; Nishitani, K. &amp; Ohtani, M. &amp; Okamoto, T. &amp; Okumura, M. &amp; Phillips, J. &amp; Pollak, B. &amp; Reinders, A. &amp; Rovekamp, M. &amp; Sano, R. &amp; Sawa, S. &amp; Schmid, M. W. &amp; Shirakawa, M. &amp; Solano, R. &amp; Spunde, A. &amp; Suetsugu, N. &amp; Sugano, S. &amp; Sugiyama, A. &amp; Sun, R. &amp; Suzuki, Y. &amp; Takenaka, M. &amp; Takezawa, D. &amp; Tomogane, H. &amp; Tsuzuki, M. &amp; Ueda, T. &amp; Umeda, M. &amp; Ward, J. M. &amp; Watanabe, Y. &amp; Yazaki, K. &amp; Yokoyama, R. &amp; Yoshitake, Y. &amp; Yotsui, I. &amp; Zachgo, S. &amp; Schmutz, J." box="[826,1028,1106,1125]" pageId="2" pageNumber="32" pagination="287 - 304" refId="ref6849" refString="Bowman, J. L., Kohchi, T., Yamato, K. T., Jenkins, J., Shu, S., Ishizaki, K., Yamaoka, S., Nishihama, R., Nakamura, Y., Berger, F., Adam, C., Aki, S. S., Althoff, Fl, Araki, T., Arteaga-Vazquez, M. A., Balasubrmanian, S., Barry, K., Bauer, D., Boehm, C. R., Briginshaw, L., Caballero-Perez, J., Catarino, B., Chen, F., Chiyoda, S., Chovatia, M., Davies, K. M., Delmans, M., Demura, T., Dierschke, T., Dolan, L., Dorantes-Acosta, A. E., Eklund, D. M., Florent, S. N., Flores-Sandoval, E., Fujiyama, A., Fukuzawa, H., Galik, B., Grimanelli, D., Grimwood, J., Grossniklaus, U., Hamada, T., Haseloff, J., Hetherington, A. J., Higo, A., Hirakawa, Y., Hundley, H. N., Ikeda, Y., Inoue, K., Inoue, S. I., Ishida, S., Jia, Q., Kakita, M., Kanazawa, T., Kawai, Y., Kawashima, T., Kennedy, M., Kinose, K., Kinoshita, T., Kohara, Y., Koide, E., Komatsu, K., Kopischke, S., Kubo, M., Kyozuka, J., Lagercrantz, U., Lin, S. S., Lindquist, E., Lipzen, A. M., Lu, C. W., De Luna, E., Martienssen, R. A., Minamino, N., Mizutani, M., Mizutani, M., Mochizuki, N., Monte, I., Mosher, R., Nagasaki, H., Nakagami, H., Naramoto, S., Nishitani, K., Ohtani, M., Okamoto, T., Okumura, M., Phillips, J., Pollak, B., Reinders, A., Rovekamp, M., Sano, R., Sawa, S., Schmid, M. W., Shirakawa, M., Solano, R., Spunde, A., Suetsugu, N., Sugano, S., Sugiyama, A., Sun, R., Suzuki, Y., Takenaka, M., Takezawa, D., Tomogane, H., Tsuzuki, M., Ueda, T., Umeda, M., Ward, J. M., Watanabe, Y., Yazaki, K., Yokoyama, R., Yoshitake, Y., Yotsui, I., Zachgo, S., Schmutz, J., 2017. Insights into land plant evolution garnered from the Marchantia polymorpha genome. Cell 171, 287 - 304." type="journal article" year="2017">Bowman et al., 2017</bibRefCitation>
). The genes encoding cinnamate 4-hydroxylase (C4H) and 4-coumaroyl CoA ligase (4CL), which participate in phenylpropanoid biosynthesis, are also present in the genome of
<emphasis id="2DF9EA929347FF9AFA04ADF6B03FFB1C" bold="true" italics="true" pageId="2" pageNumber="32">
<taxonomicName id="D88D4D039347FF9AFA04ADF6B03BFB1C" class="Marchantiopsida" family="Marchantiaceae" genus="Marchantia" kingdom="Plantae" order="Marchantiales" pageId="2" pageNumber="32" phylum="Marchantiophyta" rank="species" species="polymorpha">M. polymorpha</taxonomicName>
.
</emphasis>
In contrast, no
<emphasis id="2DF9EA929347FF9AFB9CADDAB73DFB1C" bold="true" box="[1051,1150,1190,1209]" italics="true" pageId="2" pageNumber="32">PAL, C4H,</emphasis>
or 4CL genes are present in algae such as
<emphasis id="2DF9EA929347FF9AFC05ADBDB758FB71" bold="true" box="[898,1051,1217,1236]" italics="true" pageId="2" pageNumber="32">
<taxonomicName id="D88D4D039347FF9AFC05ADBDB754FB71" authorityName="Ehrenberg" authorityYear="1833" box="[898,1047,1217,1236]" class="Chlorophyceae" family="Chlamydomonadaceae" genus="Chlamydomonas" kingdom="Plantae" order="Chlamydomonadales" pageId="2" pageNumber="32" phylum="Chlorophyta" rank="genus">Chlamydomonas</taxonomicName>
,
</emphasis>
though they do have genes that encode enzymes in the shikimate pathway, which provides aromatic amino acids such as phenylalanine and tyrosine (
<bibRefCitation id="7B1C4B719347FF9AFB10AD85B621FAA9" author="Bowman, J. L. &amp; Kohchi, T. &amp; Yamato, K. T. &amp; Jenkins, J. &amp; Shu, S. &amp; Ishizaki, K. &amp; Yamaoka, S. &amp; Nishihama, R. &amp; Nakamura, Y. &amp; Berger, F. &amp; Adam, C. &amp; Aki, S. S. &amp; Araki, T. &amp; Arteaga-Vazquez, M. A. &amp; Balasubrmanian, S. &amp; Barry, K. &amp; Bauer, D. &amp; Boehm, C. R. &amp; Briginshaw, L. &amp; Caballero-Perez, J. &amp; Catarino, B. &amp; Chen, F. &amp; Chiyoda, S. &amp; Chovatia, M. &amp; Davies, K. M. &amp; Delmans, M. &amp; Demura, T. &amp; Dierschke, T. &amp; Dolan, L. &amp; Dorantes-Acosta, A. E. &amp; Eklund, D. M. &amp; Florent, S. N. &amp; Flores-Sandoval, E. &amp; Fujiyama, A. &amp; Fukuzawa, H. &amp; Galik, B. &amp; Grimanelli, D. &amp; Grimwood, J. &amp; Grossniklaus, U. &amp; Hamada, T. &amp; Haseloff, J. &amp; Hetherington, A. J. &amp; Higo, A. &amp; Hirakawa, Y. &amp; Hundley, H. N. &amp; Ikeda, Y. &amp; Inoue, K. &amp; Inoue, S. I. &amp; Ishida, S. &amp; Jia, Q. &amp; Kakita, M. &amp; Kanazawa, T. &amp; Kawai, Y. &amp; Kawashima, T. &amp; Kennedy, M. &amp; Kinose, K. &amp; Kinoshita, T. &amp; Kohara, Y. &amp; Koide, E. &amp; Komatsu, K. &amp; Kopischke, S. &amp; Kubo, M. &amp; Kyozuka, J. &amp; Lagercrantz, U. &amp; Lin, S. S. &amp; Lindquist, E. &amp; Lipzen, A. M. &amp; Lu, C. W. &amp; De Luna, E. &amp; Martienssen, R. A. &amp; Minamino, N. &amp; Mizutani, M. &amp; Mizutani, M. &amp; Mochizuki, N. &amp; Monte, I. &amp; Mosher, R. &amp; Nagasaki, H. &amp; Nakagami, H. &amp; Naramoto, S. &amp; Nishitani, K. &amp; Ohtani, M. &amp; Okamoto, T. &amp; Okumura, M. &amp; Phillips, J. &amp; Pollak, B. &amp; Reinders, A. &amp; Rovekamp, M. &amp; Sano, R. &amp; Sawa, S. &amp; Schmid, M. W. &amp; Shirakawa, M. &amp; Solano, R. &amp; Spunde, A. &amp; Suetsugu, N. &amp; Sugano, S. &amp; Sugiyama, A. &amp; Sun, R. &amp; Suzuki, Y. &amp; Takenaka, M. &amp; Takezawa, D. &amp; Tomogane, H. &amp; Tsuzuki, M. &amp; Ueda, T. &amp; Umeda, M. &amp; Ward, J. M. &amp; Watanabe, Y. &amp; Yazaki, K. &amp; Yokoyama, R. &amp; Yoshitake, Y. &amp; Yotsui, I. &amp; Zachgo, S. &amp; Schmutz, J." box="[1175,1378,1273,1292]" pageId="2" pageNumber="32" pagination="287 - 304" refId="ref6849" refString="Bowman, J. L., Kohchi, T., Yamato, K. T., Jenkins, J., Shu, S., Ishizaki, K., Yamaoka, S., Nishihama, R., Nakamura, Y., Berger, F., Adam, C., Aki, S. S., Althoff, Fl, Araki, T., Arteaga-Vazquez, M. A., Balasubrmanian, S., Barry, K., Bauer, D., Boehm, C. R., Briginshaw, L., Caballero-Perez, J., Catarino, B., Chen, F., Chiyoda, S., Chovatia, M., Davies, K. M., Delmans, M., Demura, T., Dierschke, T., Dolan, L., Dorantes-Acosta, A. E., Eklund, D. M., Florent, S. N., Flores-Sandoval, E., Fujiyama, A., Fukuzawa, H., Galik, B., Grimanelli, D., Grimwood, J., Grossniklaus, U., Hamada, T., Haseloff, J., Hetherington, A. J., Higo, A., Hirakawa, Y., Hundley, H. N., Ikeda, Y., Inoue, K., Inoue, S. I., Ishida, S., Jia, Q., Kakita, M., Kanazawa, T., Kawai, Y., Kawashima, T., Kennedy, M., Kinose, K., Kinoshita, T., Kohara, Y., Koide, E., Komatsu, K., Kopischke, S., Kubo, M., Kyozuka, J., Lagercrantz, U., Lin, S. S., Lindquist, E., Lipzen, A. M., Lu, C. W., De Luna, E., Martienssen, R. A., Minamino, N., Mizutani, M., Mizutani, M., Mochizuki, N., Monte, I., Mosher, R., Nagasaki, H., Nakagami, H., Naramoto, S., Nishitani, K., Ohtani, M., Okamoto, T., Okumura, M., Phillips, J., Pollak, B., Reinders, A., Rovekamp, M., Sano, R., Sawa, S., Schmid, M. W., Shirakawa, M., Solano, R., Spunde, A., Suetsugu, N., Sugano, S., Sugiyama, A., Sun, R., Suzuki, Y., Takenaka, M., Takezawa, D., Tomogane, H., Tsuzuki, M., Ueda, T., Umeda, M., Ward, J. M., Watanabe, Y., Yazaki, K., Yokoyama, R., Yoshitake, Y., Yotsui, I., Zachgo, S., Schmutz, J., 2017. Insights into land plant evolution garnered from the Marchantia polymorpha genome. Cell 171, 287 - 304." type="journal article" year="2017">Bowman et al., 2017</bibRefCitation>
). Based on genomic data from several plants, phenylpropanoids are considered to be characteristic specialized metabolites in land plants.
</paragraph>
<paragraph id="1F3236809347FF9AFCD4AC31B0A7F8BB" blockId="2.[818,1488,1106,1822]" pageId="2" pageNumber="32">
Phylogenetic analysis revealed that MpPAL2-10 formed a cluster that was separate from that of MpPAL1 and the other PALs of the model moss
<taxonomicName id="D88D4D039347FF9AFCE0ACF9B764FA3D" box="[871,1063,1413,1432]" class="Bryopsida" family="Funariaceae" genus="Physcomitrella" kingdom="Plantae" order="Funariales" pageId="2" pageNumber="32" phylum="Bryophyta" rank="species" species="patens">
<emphasis id="2DF9EA929347FF9AFCE0ACF9B764FA3D" bold="true" box="[871,1063,1413,1432]" italics="true" pageId="2" pageNumber="32">Physcomitrella patens</emphasis>
</taxonomicName>
and flowering plants (
<figureCitation id="87B62A059347FF9AFA87ACF9B603FA3D" box="[1280,1344,1413,1432]" captionStart="Fig" captionStartId="2.[477,507,684,701]" captionTargetBox="[340,1246,154,659]" captionTargetId="figure-633@2.[339,1249,152,661]" captionTargetPageId="2" captionText="Fig. 2. The structures of luteolin (1), apigenin (2), and isoriccardin C (3)." figureDoi="http://doi.org/10.5281/zenodo.10484412" httpUri="https://zenodo.org/record/10484412/files/figure.png" pageId="2" pageNumber="32">Fig. S2</figureCitation>
). These results suggested that MpPAL1 is an ancestral land plant PAL. Amino acid sequence alignment analysis of the MpPALs revealed that eight of them have the conserved active site amino acid sequence Ala-Ser-Gly (
<figureCitation id="87B62A059347FF9AFA2BACA5B00AF9A2" captionStart="Fig" captionStartId="2.[1034,1064,742,759]" captionTargetBox="[102,1002,743,1045]" captionTargetId="figure-654@2.[100,1004,741,1046]" captionTargetPageId="2" captionText="Fig. 3. Accumulation of luteolin (1), apigenin (2), and isoriccardin C (3) induced by wounding in M. polymorpha. M. polymorpha plants were grown on 1/2 Gamborg's B5 medium containing 1.4% agar for 30 days and then subjected to wounding treatment. Plants were harvested at the indicated time. Data represent means ± S.D. of three separate experiments. The asterisks represent significant differences between wounded and control plants (Student's t-test, *p &lt;0.05, **p &lt;0.01)." figureDoi="http://doi.org/10.5281/zenodo.10484414" httpUri="https://zenodo.org/record/10484414/files/figure.png" pageId="2" pageNumber="32">Fig. S3</figureCitation>
). Cyclization of Ala-Ser-Gly produces the cofactor of the PAL reaction, 3,5-dihydro-5-methylidene-4
<emphasis id="2DF9EA929347FF9AFBFFAF6CB7C4F986" bold="true" box="[1144,1159,1552,1571]" italics="true" pageId="2" pageNumber="32">H</emphasis>
-imidazole-4-one (MIO) (
<bibRefCitation id="7B1C4B719347FF9AFAF8AF6CB0A1F99A" author="Schuster, B. &amp; Retey, J." pageId="2" pageNumber="32" pagination="8433 - 8437" refId="ref8792" refString="Schuster, B., Retey, J., 1995. The mechanism of action of phenylalanine ammonia-lyase: the role of prosthetic dehydroalanine. Proc. Natl. Acad. Sci. U. S. A 92, 8433 - 8437." type="journal article" year="1995">Schuster and J Rétey, 1995</bibRefCitation>
;
<bibRefCitation id="7B1C4B719347FF9AFC77AF50B7E4F99A" author="Alunni, S. &amp; Cipiciani, A. &amp; Fioroni, G. &amp; Ottavi, L." box="[1008,1191,1580,1599]" pageId="2" pageNumber="32" pagination="170 - 175" refId="ref6495" refString="Alunni, S., Cipiciani, A., Fioroni, G., Ottavi, L., 2003. Mechanisms of inhibition of phenylalanine ammonia-lyase by phenol inhibitors and phenol / glycine synergistic inhibitors. Arch. Biochem. Biophys. 412, 170 - 175." type="journal article" year="2003">Alunni et al., 2003</bibRefCitation>
;
<bibRefCitation id="7B1C4B719347FF9AFB32AF50B6C5F99A" author="Calabrese, J. C. &amp; Jordan, D. B. &amp; Boodhoo, A. &amp; Sariaslani, S. &amp; Vannelli, T." box="[1205,1414,1580,1599]" pageId="2" pageNumber="32" pagination="11403 - 11416" refId="ref7471" refString="Calabrese, J. C., Jordan, D. B., Boodhoo, A., Sariaslani, S., Vannelli, T., 2004. Crystal structure of phenylalanine ammonia lyase: multiple helix dipoles implicated in catalysis. Biochemistry 43, 11403 - 11416." type="journal article" year="2004">Calabrese et al., 2004</bibRefCitation>
). However, the predicted amino acid sequence of MpPAL10 is much shorter than that of the other predicted MpPALs and does not contain the conserved active site amino acid sequence Ala-Ser-Gly. Consequently, MpPAL10 likely does not have PAL activity. In the conserved amino acid sequence that forms MIO in MpPAL2, the Ser residue is substituted by Ala, a change that significantly reduced PAL activity in
<taxonomicName id="D88D4D039347FF9AFADAAFAFB034F8A7" class="Magnoliopsida" family="Apiaceae" genus="Petroselinum" kingdom="Plantae" order="Apiales" pageId="2" pageNumber="32" phylum="Tracheophyta" rank="species" species="crispum">
<emphasis id="2DF9EA929347FF9AFADAAFAFB034F8A7" bold="true" italics="true" pageId="2" pageNumber="32">Petroselinum crispum</emphasis>
</taxonomicName>
L. (
<bibRefCitation id="7B1C4B719347FF9AFC24AF93B7DFF8A7" author="Schuster, B. &amp; Retey, J." box="[931,1180,1775,1794]" pageId="2" pageNumber="32" pagination="8433 - 8437" refId="ref8792" refString="Schuster, B., Retey, J., 1995. The mechanism of action of phenylalanine ammonia-lyase: the role of prosthetic dehydroalanine. Proc. Natl. Acad. Sci. U. S. A 92, 8433 - 8437." type="journal article" year="1995">Schuster and Rétey, 1995</bibRefCitation>
); therefore, MpPAL2 likely has weak PAL activity.
</paragraph>
</subSubSection>
</treatment>
</document>