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<document id="791AFA5B4B76303099A3516B2870DDD9" ID-DOI="10.1016/j.phytochem.2021.113051" ID-ISSN="1873-3700" ID-Zenodo-Dep="8235350" IM.bibliography_approvedBy="carolina" IM.illustrations_approvedBy="carolina" IM.materialsCitations_approvedBy="carolina" IM.metadata_approvedBy="felipe" IM.tables_approvedBy="carolina" IM.taxonomicNames_approvedBy="carolina" IM.treatments_approvedBy="carolina" checkinTime="1691690177219" checkinUser="felipe" docAuthor="Toporkova, Yana Y., Askarova, Elena K., Gorina, Svetlana S., Mukhtarova, Lucia S. &amp; Grechkin, Alexander N." docDate="2022" docId="702887CF7A49D252FFA633F25DABDAAD" docLanguage="en" docName="Phytochemistry.195.113051.pdf" docOrigin="Phytochemistry (113051) 195" docSource="http://dx.doi.org/10.1016/j.phytochem.2021.113051" docStyle="DocumentStyle:F36D69FC8B198FBE91029DF9C24697D3.5:Phytochemistry.2020-.journal_article" docStyleId="F36D69FC8B198FBE91029DF9C24697D3" docStyleName="Phytochemistry.2020-.journal_article" docStyleVersion="5" docTitle="Selaginella moellendorffii subsp. oxylipin Hieron. 1901" docType="treatment" docVersion="3" lastPageNumber="9" masterDocId="8C11FFB77A4CD25AFFC2323E5F3BDF4F" masterDocTitle="Oxylipin biosynthesis in spikemoss Selaginella moellendorffii: Identification of allene oxide synthase (CYP 74 L 2) and hydroperoxide lyase (CYP 74 L 1)" masterLastPageNumber="12" masterPageNumber="1" pageNumber="6" updateTime="1692110293491" updateUser="ExternalLinkService">
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<mods:title id="D4D6414ABEB47F49845881D3C2F1F871">Oxylipin biosynthesis in spikemoss Selaginella moellendorffii: Identification of allene oxide synthase (CYP 74 L 2) and hydroperoxide lyase (CYP 74 L 1)</mods:title>
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<mods:namePart id="648A9DD3593D0CC5564814C5D3EE71D3">Toporkova, Yana Y.</mods:namePart>
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<mods:namePart id="5B40BED3D3D2938F01AAB8B8F9587FFC">Askarova, Elena K.</mods:namePart>
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<mods:namePart id="5770DF21E467722413C23C79588D8358">Gorina, Svetlana S.</mods:namePart>
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<mods:namePart id="1D4E817DA8AD05B094E270247FD3CFA3">Mukhtarova, Lucia S.</mods:namePart>
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<mods:namePart id="D3669A1C853E6AFB349E15CCCE2B58EF">Grechkin, Alexander N.</mods:namePart>
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<subSubSection id="B09B65527A49D25FFFA633F25EF3DE90" box="[100,456,460,479]" pageId="5" pageNumber="6" type="nomenclature">
<paragraph id="F83E36D97A49D25FFFA633F25EF3DE90" blockId="5.[100,456,460,479]" box="[100,456,460,479]" pageId="5" pageNumber="6">
<heading id="A37681B57A49D25FFFA633F25EF3DE90" bold="true" box="[100,456,460,479]" fontSize="36" level="1" pageId="5" pageNumber="6" reason="1">
<emphasis id="CAF5EACB7A49D25FFFA633F25EF3DE90" bold="true" box="[100,456,460,479]" italics="true" pageId="5" pageNumber="6">
2.5.
<taxonomicName id="3F814D5A7A49D25FFF5733F25E13DE90" authority="Hieron., 1901" authorityName="Hieron." authorityYear="1901" box="[149,296,460,479]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="subSpecies" species="moellendorffii" subSpecies="oxylipin">S. moellendorffii</taxonomicName>
oxylipin profiling
</emphasis>
</heading>
</paragraph>
</subSubSection>
<subSubSection id="B09B65527A49D252FF46303A5DABDAAD" lastPageId="8" lastPageNumber="9" pageId="5" pageNumber="6" type="description">
<paragraph id="F83E36D97A49D25FFF46303A5DABDCF6" blockId="5.[100,770,515,954]" pageId="5" pageNumber="6">
The aerial parts of
<taxonomicName id="3F814D5A7A49D25FFE82303A5EEEDD59" box="[320,469,515,535]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="moellendorffii">
<emphasis id="CAF5EACB7A49D25FFE82303A5EEEDD59" bold="true" box="[320,469,515,535]" italics="true" pageId="5" pageNumber="6">S. moellendorffii</emphasis>
</taxonomicName>
plants possessed complex oxylipins patterns (
<figureCitation id="60BA2A5C7A49D25FFF3B301E5E14DD7C" box="[249,303,544,563]" captionStart="Fig" captionStartId="5.[100,130,1888,1905]" captionTargetBox="[208,1379,1560,1859]" captionTargetId="figure-973@5.[206,1381,1558,1861]" captionTargetPageId="5" captionText="Fig. 5. The TIC chromatogram of oxylipins (Me/TMS) from the aerial parts of S. moellendorffii plants. DE1, (ω5Z)-etheroleic acid; DE2, etheroleic acid; DE3, (11Z)- etheroleic acid; DE4, etherolenic acid; DE5, (ω5Z)-etherolenic acid; DE6, (11Z)-etherolenic acid; 5, 11-hydroxy-12,13-epoxy-9-octadecenoic acid; 5a, 11-hydroxy- 12,13-epoxy-9,15-octadecadienoic acid; 10, eicosanoic acid; 11, 13-ketooctadecadienoic acid; 12, epimeric 9-hydroxy-12,13-epoxy-10-octadecenoic acid; 12a, epimeric 9-hydroxy-12,13-epoxy-10,15-octadecadienoic acid. Additionally, 13-HOD, as well as cis and trans isomers of 12-OPDA were detected." figureDoi="http://doi.org/10.5281/zenodo.8235360" httpUri="https://zenodo.org/record/8235360/files/figure.png" pageId="5" pageNumber="6">Fig. 5</figureCitation>
) similar to those described before for
<taxonomicName id="3F814D5A7A49D25FFD5B301E5E4EDD00" authority="(Ogorodnikova et al., 2015)" baseAuthorityName="Ogorodnikova" baseAuthorityYear="2015" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="martensii">
<emphasis id="CAF5EACB7A49D25FFD5B301E5C39DD7C" bold="true" box="[665,770,544,563]" italics="true" pageId="5" pageNumber="6">S. martensii</emphasis>
(
<bibRefCitation id="9C104B287A49D25FFFAE30025E50DD01" author="Ogorodnikova, A. V. &amp; Mukhitova, F. K. &amp; Grechkin, A. N." box="[108,363,571,591]" pageId="5" pageNumber="6" pagination="42 - 50" refId="ref14742" refString="Ogorodnikova, A. V., Mukhitova, F. K., Grechkin, A. N., 2015. Oxylipins in the spikemoss Selaginella martensii: detection of divinyl ethers, 12 - oxophytodienoic acid and related cyclopentenones. Phytochemistry 118, 42 - 50. https: // doi. org / 10.1016 / j. phytochem. 2015.08.003." type="journal article" year="2015">Ogorodnikova et al., 2015</bibRefCitation>
)
</taxonomicName>
. The most prominent oxylipins were the products of DES and AOS activities. These were the divinyl ethers (
<emphasis id="CAF5EACB7A49D25FFD0830695FB6DDC9" bold="true" pageId="5" pageNumber="6">DE1 DE6</emphasis>
,
<figureCitation id="60BA2A5C7A49D25FFF5A304D5FF7DDC9" box="[152,204,627,646]" captionStart="Fig" captionStartId="5.[100,130,1888,1905]" captionTargetBox="[208,1379,1560,1859]" captionTargetId="figure-973@5.[206,1381,1558,1861]" captionTargetPageId="5" captionText="Fig. 5. The TIC chromatogram of oxylipins (Me/TMS) from the aerial parts of S. moellendorffii plants. DE1, (ω5Z)-etheroleic acid; DE2, etheroleic acid; DE3, (11Z)- etheroleic acid; DE4, etherolenic acid; DE5, (ω5Z)-etherolenic acid; DE6, (11Z)-etherolenic acid; 5, 11-hydroxy-12,13-epoxy-9-octadecenoic acid; 5a, 11-hydroxy- 12,13-epoxy-9,15-octadecadienoic acid; 10, eicosanoic acid; 11, 13-ketooctadecadienoic acid; 12, epimeric 9-hydroxy-12,13-epoxy-10-octadecenoic acid; 12a, epimeric 9-hydroxy-12,13-epoxy-10,15-octadecadienoic acid. Additionally, 13-HOD, as well as cis and trans isomers of 12-OPDA were detected." figureDoi="http://doi.org/10.5281/zenodo.8235360" httpUri="https://zenodo.org/record/8235360/files/figure.png" pageId="5" pageNumber="6">Fig. 5</figureCitation>
) and the cyclopentenones,
<emphasis id="CAF5EACB7A49D25FFE0B304D5EDBDDC9" bold="true" box="[457,480,627,646]" italics="true" pageId="5" pageNumber="6">cis</emphasis>
- and
<emphasis id="CAF5EACB7A49D25FFDD1304A5D7BDDC8" bold="true" box="[531,576,628,647]" italics="true" pageId="5" pageNumber="6">trans</emphasis>
-12-oxo-PDA, as well as the
<emphasis id="CAF5EACB7A49D25FFF6B30B15FFADDED" bold="true" box="[169,193,655,674]" italics="true" pageId="5" pageNumber="6">iso</emphasis>
-12-oxo-PDA, 15(
<emphasis id="CAF5EACB7A49D25FFEAA30AE5E4FDDEC" bold="true" box="[360,372,656,675]" italics="true" pageId="5" pageNumber="6">Z</emphasis>
)-12-oxo-9(13),15-phytodienoic acid. The spectra for the detected divinyl ethers and cyclopentenones corresponded to those described before (
<bibRefCitation id="9C104B287A49D25FFE0730F95DFCDD95" author="Ogorodnikova, A. V. &amp; Mukhitova, F. K. &amp; Grechkin, A. N." box="[453,711,711,731]" pageId="5" pageNumber="6" pagination="42 - 50" refId="ref14742" refString="Ogorodnikova, A. V., Mukhitova, F. K., Grechkin, A. N., 2015. Oxylipins in the spikemoss Selaginella martensii: detection of divinyl ethers, 12 - oxophytodienoic acid and related cyclopentenones. Phytochemistry 118, 42 - 50. https: // doi. org / 10.1016 / j. phytochem. 2015.08.003." type="journal article" year="2015">Ogorodnikova et al., 2015</bibRefCitation>
). The oxylipin profile of
<taxonomicName id="3F814D5A7A49D25FFEE230DD5E8DDDB9" box="[288,438,739,758]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="moellendorffii">
<emphasis id="CAF5EACB7A49D25FFEE230DD5E8DDDB9" bold="true" box="[288,438,739,758]" italics="true" pageId="5" pageNumber="6">S. moellendorffii</emphasis>
</taxonomicName>
, besides the mentioned products, contained several epoxyalcohols. These were 11-hydroxy-12,13-epoxy-9-octadecenoic (
<emphasis id="CAF5EACB7A49D25FFEDC31255E11DC61" bold="true" box="[286,298,795,814]" pageId="5" pageNumber="6">5</emphasis>
), 11-hydroxy-12,13-epoxy-9,15-octadecadienoic (
<emphasis id="CAF5EACB7A49D25FFFAE31095FBFDC05" bold="true" box="[108,132,823,842]" pageId="5" pageNumber="6">5a</emphasis>
), 9-hydroxy-12,13-epoxy-10-octadecenoic acid (
<emphasis id="CAF5EACB7A49D25FFDAF31095DBDDC05" bold="true" box="[621,646,823,842]" pageId="5" pageNumber="6">12</emphasis>
) and 9-hydroxy-12,13-epoxy-10,15-octadecadienoic acid (
<emphasis id="CAF5EACB7A49D25FFDED316C5D68DC2A" bold="true" box="[559,595,850,869]" pageId="5" pageNumber="6">12a</emphasis>
) acids (EAS products). The mass spectra of epoxyalcohols
<emphasis id="CAF5EACB7A49D25FFE3D31515D30DCCD" bold="true" box="[511,523,879,898]" pageId="5" pageNumber="6">5</emphasis>
and
<emphasis id="CAF5EACB7A49D25FFD8031515D61DCCD" bold="true" box="[578,602,879,898]" pageId="5" pageNumber="6">5a</emphasis>
are described in Supplementary Information. The mass spectra of epoxyalcohols
<emphasis id="CAF5EACB7A49D25FFD0231B45DE2DCD2" bold="true" box="[704,729,906,925]" pageId="5" pageNumber="6">12</emphasis>
and
<emphasis id="CAF5EACB7A49D25FFFA631985FB2DCF6" bold="true" box="[100,137,934,953]" pageId="5" pageNumber="6">12a</emphasis>
have been described earlier (
<bibRefCitation id="9C104B287A49D25FFE6331985DB9DCF6" author="Toporkova, Y. Y. &amp; Smirnova, E. O. &amp; Gorina, S. S. &amp; Mukhtarova, L. S. &amp; Grechkin, A. N." box="[417,642,934,954]" pageId="5" pageNumber="6" pagination="73 - 82" refId="ref16051" refString="Toporkova, Y. Y., Smirnova, E. O., Gorina, S. S., Mukhtarova, L. S., Grechkin, A. N., 2018 a. Detection of the first higher plant epoxyalcohol synthase: molecular cloning and characterisation of the CYP 74 M 2 enzyme of spikemoss Selaginella moellendorffii. Phytochemistry 156, 73 - 82. https: // doi. org / 10.1016 / j. phytochem. 2018.08.010." type="journal article" year="2018">Toporkova et al., 2018a</bibRefCitation>
).
</paragraph>
<paragraph id="F83E36D97A49D25FFFA631DD5DCBDCB9" blockId="5.[100,752,995,1015]" box="[100,752,995,1015]" pageId="5" pageNumber="6">
<heading id="A37681B57A49D25FFFA631DD5DCBDCB9" bold="true" box="[100,752,995,1015]" centered="true" fontSize="36" level="1" pageId="5" pageNumber="6" reason="1">
<emphasis id="CAF5EACB7A49D25FFFA631DD5DCBDCB9" bold="true" box="[100,752,995,1015]" italics="true" pageId="5" pageNumber="6">
2.6. Alignment of amino acid sequences of
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74Ls with other
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74s
</emphasis>
</heading>
</paragraph>
<paragraph id="F83E36D97A49D25FFF4636255B1DDFE8" blockId="5.[100,771,1051,1517]" lastBlockId="5.[818,1487,148,780]" pageId="5" pageNumber="6">
The genome of
<taxonomicName id="3F814D5A7A49D25FFEDD36255E8FDB61" box="[287,436,1051,1070]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="moellendorffii">
<emphasis id="CAF5EACB7A49D25FFEDD36255E8FDB61" bold="true" box="[287,436,1051,1070]" italics="true" pageId="5" pageNumber="6">S. moellendorffii</emphasis>
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contains at least 10
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74
<taxonomicName id="3F814D5A7A49D25FFD0F36225E1CDB05" authority="(Banks et al., 2011)" baseAuthorityName="Banks" baseAuthorityYear="2011" class="Alphaproteobacteria" family="Methylobacteriaceae" genus="Methylobacterium" kingdom="Bacteria" order="Rhizobiales" pageId="5" pageNumber="6" phylum="Proteobacteria" rank="species" species="genes">genes (Banks et al., 2011)</taxonomicName>
belonging to four subfamilies
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74J,
<collectionCode id="9E90AE1C7A49D25FFD6D36095DE2DB05" box="[687,729,1079,1098]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="5" pageNumber="6" type="Herbarium">CYP</collectionCode>
74K,
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74
<collectionCode id="9E90AE1C7A49D25FFF60366D5F94DB29" box="[162,175,1107,1126]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="5" pageNumber="6" type="Herbarium">L</collectionCode>
and
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<specimenCount id="EE87FD507A49D25FFEC8366D5E03DB29" box="[266,312,1107,1126]" pageId="5" pageNumber="6" type="generic">
74
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.
</specimenCount>
All these sequences possess significant peculiarities of catalytically essential domains, primarily the “
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/
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toggle” at the SRS-1 near the N-end and the I-helix groove domain (including two amino acids behind it). Normally in
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and
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sequences the “
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/
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toggle” contains phenylalanine, whereas in HPL and
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, it contains leucine. Phe/Leu substitution and vice versa regularly leads to alteration in the catalytic mechanism (
<bibRefCitation id="9C104B287A49D25FFEB636C55D32DA41" author="Lee, D. - S. &amp; Nioche, P. &amp; Hamberg, M. &amp; Raman, C. S." box="[372,521,1275,1294]" pageId="5" pageNumber="6" pagination="363 - 370" refId="ref14297" refString="Lee, D. - S., Nioche, P., Hamberg, M., Raman, C. S., 2008. Structural insights into the evolutionary paths of oxylipin biosynthesis enzymes. Nature 455, 363 - 370. https: // doi. org / 10.1038 / nature 07307." type="journal article" year="2008">Lee et al., 2008</bibRefCitation>
;
<bibRefCitation id="9C104B287A49D25FFDD436C55DC7DA41" author="Toporkova, Y. Y. &amp; Gorina, S. S. &amp; Bessolitsyna, E. K. &amp; Smirnova, E. O. &amp; Fatykhova, V. S. &amp; Bruhlmann, F. &amp; Ilyina, T. M. &amp; Mukhtarova, L. S. &amp; Grechkin, A. N." box="[534,764,1275,1294]" pageId="5" pageNumber="6" pagination="369 - 378" refId="ref16136" refString="Toporkova, Y. Y., Gorina, S. S., Bessolitsyna, E. K., Smirnova, E. O., Fatykhova, V. S., Bruhlmann, F., Ilyina, T. M., Mukhtarova, L. S., Grechkin, A. N., 2018 b. Double function hydroperoxide lyases / epoxyalcohol synthases (CYP 74 C) of higher plants: identification and conversion into allene oxide synthases by site-directed mutagenesis. Biochim. Biophys. Acta 1863, 369 - 378. https: // doi. org / 10.1016 / j. bbalip. 2018.01.002." type="journal article" year="2018">Toporkova et al., 2018b</bibRefCitation>
,
<bibRefCitation id="9C104B287A49D25FFFA637285FA4DA66" author="Toporkova, Y. Y. &amp; Askarova, E. K. &amp; Gorina, S. S. &amp; Ogorodnikova, A. V. &amp; Mukhtarova, L. S. &amp; Grechkin, A. N." box="[100,159,1302,1321]" pageId="5" pageNumber="6" pagination="158743" refId="ref16339" refString="Toporkova, Y. Y., Askarova, E. K., Gorina, S. S., Ogorodnikova, A. V., Mukhtarova, L. S., Grechkin, A. N., 2020 b. Epoxyalcohol synthase activity of the CYP 74 B enzymes of higher plants. Biochim. Biophys. Acta 1865, 158743. https: // doi. org / 10.1016 / j. bbalip. 2020.158743." type="journal article" year="2020">2020b</bibRefCitation>
). Among
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<emphasis id="CAF5EACB7A49D25FFEC837285E99DA66" bold="true" box="[266,418,1302,1321]" italics="true" pageId="5" pageNumber="6">S. moellendorffii</emphasis>
CYP
</taxonomicName>
74s the “
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/
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toggle” contains leucine only in two sequences,
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74
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1 and
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74
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3 (
<figureCitation id="60BA2A5C7A49D25FFD42370C5D8EDA0A" box="[640,693,1330,1349]" captionStart="Fig" captionStartId="6.[100,130,753,770]" captionTargetBox="[209,1377,152,722]" captionTargetId="figure-285@6.[206,1381,148,725]" captionTargetPageId="6" captionText="Fig. 6. The multiple alignment of the CYP74L1, CYP74L2, and CYP74L3 sequences of S. moellendorffii with other CYP74s described earlier. Conservative structures are marked as follows: the I-helix groove region (SRS-4) is numbered 16, two positions after the I-helix groove region are marked by ◆ symbol, the F/L toggle is marked by ▾ symbol." figureDoi="http://doi.org/10.5281/zenodo.8235362" httpUri="https://zenodo.org/record/8235362/files/figure.png" pageId="5" pageNumber="6">Fig. 6</figureCitation>
), which are DESs. The absence of other
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74s, except SmDES1 (
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74
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1) and SmDES3 (
<collectionCode id="9E90AE1C7A49D25FFF0237545FD5DA32" box="[192,238,1386,1405]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="5" pageNumber="6" type="Herbarium">CYP</collectionCode>
74
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3), having a Leu at this site suggested the absence of HPLs in
<taxonomicName id="3F814D5A7A49D25FFF7537B85E77DAD6" box="[183,332,1414,1433]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="moellendorffii">
<emphasis id="CAF5EACB7A49D25FFF7537B85E77DAD6" bold="true" box="[183,332,1414,1433]" italics="true" pageId="5" pageNumber="6">S. moellendorffii</emphasis>
</taxonomicName>
. However, SmHPL/
<collectionCode id="9E90AE1C7A49D25FFDC837B85D0EDAD6" box="[522,565,1414,1433]" pageId="5" pageNumber="6">AOS</collectionCode>
(
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74
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1) possesses significant HPL activity, especially towards 13-hydroperoxides of linoleic and α- linolenic acids. At the same time, its “
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/
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toggle” contains phenylalanine. To date, this is the only
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74 HPL containing phenylalanine at this site.
</paragraph>
<paragraph id="F83E36D97A49D25FFC93328E5AF6DD62" blockId="5.[818,1487,148,780]" pageId="5" pageNumber="6">
The I-helix groove domain and its environment in the
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74
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sequences also look unusual. Their alignment (
<figureCitation id="60BA2A5C7A49D25FFB1832F55A2BDF91" box="[1242,1296,203,222]" captionStart="Fig" captionStartId="6.[100,130,753,770]" captionTargetBox="[209,1377,152,722]" captionTargetId="figure-285@6.[206,1381,148,725]" captionTargetPageId="6" captionText="Fig. 6. The multiple alignment of the CYP74L1, CYP74L2, and CYP74L3 sequences of S. moellendorffii with other CYP74s described earlier. Conservative structures are marked as follows: the I-helix groove region (SRS-4) is numbered 16, two positions after the I-helix groove region are marked by ◆ symbol, the F/L toggle is marked by ▾ symbol." figureDoi="http://doi.org/10.5281/zenodo.8235362" httpUri="https://zenodo.org/record/8235362/files/figure.png" pageId="5" pageNumber="6">Fig. 6</figureCitation>
) with other
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74s shows that all three
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74Ls have a substitution of the glycine in the next position after the I-helix groove domain. AOSs and HPLs of flowering plants normally have a conserved Gly at this site. In DESs, Gly is substituted with another residue (
<figureCitation id="60BA2A5C7A49D25FFBAE33055B9ADE01" box="[1132,1185,315,334]" captionStart="Fig" captionStartId="6.[100,130,753,770]" captionTargetBox="[209,1377,152,722]" captionTargetId="figure-285@6.[206,1381,148,725]" captionTargetPageId="6" captionText="Fig. 6. The multiple alignment of the CYP74L1, CYP74L2, and CYP74L3 sequences of S. moellendorffii with other CYP74s described earlier. Conservative structures are marked as follows: the I-helix groove region (SRS-4) is numbered 16, two positions after the I-helix groove region are marked by ◆ symbol, the F/L toggle is marked by ▾ symbol." figureDoi="http://doi.org/10.5281/zenodo.8235362" httpUri="https://zenodo.org/record/8235362/files/figure.png" pageId="5" pageNumber="6">Fig. 6</figureCitation>
). DESs have either Ala (
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74D DESs) or bulkier residues like Glu (
<collectionCode id="9E90AE1C7A49D25FFB7633695BD9DE25" box="[1204,1250,343,362]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="5" pageNumber="6" type="Herbarium">CYP</collectionCode>
74
<collectionCode id="9E90AE1C7A49D25FFB3B33695A3CDE25" box="[1273,1287,343,362]" country="Germany" lsid="urn:lsid:biocol.org:col:15534" name="Botanischer Garten und Botanisches Museum Berlin-Dahlem, Zentraleinrichtung der Freien Universitaet" pageId="5" pageNumber="6" type="Herbarium">B</collectionCode>
16, LuDES), or Thr (
<collectionCode id="9E90AE1C7A49D25FFCFA334D5C5CDEC9" box="[824,871,371,390]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="5" pageNumber="6" type="Herbarium">CYP</collectionCode>
74
<collectionCode id="9E90AE1C7A49D25FFCBD334D5CABDEC9" box="[895,912,371,390]" country="Ecuador" lsid="urn:lsid:biocol.org:col:14273" name="Universidad Central" pageId="5" pageNumber="6" type="Herbarium">Q</collectionCode>
1, RaDES), or Leu (
<collectionCode id="9E90AE1C7A49D25FFBFC334D5B56DEC9" box="[1086,1133,371,390]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="5" pageNumber="6" type="Herbarium">CYP</collectionCode>
74H1, AsDES). The importance of this site for
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activity was confirmed by site-directed mutagenesis experiments; the E292G mutant form of LuDES (
<collectionCode id="9E90AE1C7A49D25FFB1A33955A3EDEF1" box="[1240,1285,427,446]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="5" pageNumber="6" type="Herbarium">CYP</collectionCode>
74
<collectionCode id="9E90AE1C7A49D25FFADF33955A10DEF1" box="[1309,1323,427,446]" country="Germany" lsid="urn:lsid:biocol.org:col:15534" name="Botanischer Garten und Botanisches Museum Berlin-Dahlem, Zentraleinrichtung der Freien Universitaet" pageId="5" pageNumber="6" type="Herbarium">B</collectionCode>
16) exhibited
<collectionCode id="9E90AE1C7A49D25FFA6433955AF4DEF1" box="[1446,1487,427,446]" pageId="5" pageNumber="6">AOS</collectionCode>
activity (
<bibRefCitation id="9C104B287A49D25FFC4A33F95B58DE95" author="Toporkova, Y. Y. &amp; Ermilova, V. S. &amp; Gorina, S. S. &amp; Mukhtarova, L. S. &amp; Osipova, E. V. &amp; Gogolev, Y. V. &amp; Grechkin, A. N." box="[904,1123,455,474]" pageId="5" pageNumber="6" pagination="2552 - 2558" refId="ref15762" refString="Toporkova, Y. Y., Ermilova, V. S., Gorina, S. S., Mukhtarova, L. S., Osipova, E. V., Gogolev, Y. V., Grechkin, A. N., 2013. Structure-function relationship in the CYP 74 family: conversion of divinyl ether synthases into allene oxide synthases by site-directed mutagenesis. FEBS Lett. 587, 2552 - 2558. https: // doi. org / 10.1016 / j. febslet. 2013.06.030." type="journal article" year="2013">Toporkova et al., 2013</bibRefCitation>
). In
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74
<collectionCode id="9E90AE1C7A49D25FFB1333F95BE5DE95" box="[1233,1246,455,474]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="5" pageNumber="6" type="Herbarium">L</collectionCode>
sequences this glycine is substituted with another amino acid leucine (
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74
<collectionCode id="9E90AE1C7A49D25FFAFB33DD5A7CDEB9" box="[1337,1351,483,502]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="5" pageNumber="6" type="Herbarium">L</collectionCode>
1) or phenylalanine (
<collectionCode id="9E90AE1C7A49D25FFCB933C05C9DDD5E" box="[891,934,510,529]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="5" pageNumber="6" type="Herbarium">CYP</collectionCode>
74
<collectionCode id="9E90AE1C7A49D25FFC7E33C05CF2DD5E" box="[956,969,510,529]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="5" pageNumber="6" type="Herbarium">L</collectionCode>
2 and
<collectionCode id="9E90AE1C7A49D25FFBD533C05B7FDD5E" box="[1047,1092,510,529]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="5" pageNumber="6" type="Herbarium">CYP</collectionCode>
74
<collectionCode id="9E90AE1C7A49D25FFB9933C05B52DD5E" box="[1115,1129,510,529]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="5" pageNumber="6" type="Herbarium">L</collectionCode>
3). However, the
<collectionCode id="9E90AE1C7A49D25FFAE633C05A76DD5E" box="[1316,1357,510,529]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="5" pageNumber="6" type="Herbarium">CYP</collectionCode>
74
<taxonomicName id="3F814D5A7A49D25FFAA033C05AF4DD5D" box="[1378,1487,510,530]" class="Alphaproteobacteria" family="Methylobacteriaceae" genus="Methylobacterium" kingdom="Bacteria" order="Rhizobiales" pageId="5" pageNumber="6" phylum="Proteobacteria" rank="species" species="enzymes">L enzymes</taxonomicName>
possessed mainly
<collectionCode id="9E90AE1C7A49D25FFC1B30245B39DD62" box="[985,1026,538,557]" pageId="5" pageNumber="6">AOS</collectionCode>
or HPL activities. No
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activity was detected.
</paragraph>
<paragraph id="F83E36D97A49D25FFC9330085CACDC43" blockId="5.[818,1487,148,780]" pageId="5" pageNumber="6">
Position #3 of HBD is occupied with a conserved Phe in AOSs and HPLs (
<figureCitation id="60BA2A5C7A49D25FFCB7306C5C94DD2A" box="[885,943,594,613]" captionStart="Fig" captionStartId="6.[100,130,753,770]" captionTargetBox="[209,1377,152,722]" captionTargetId="figure-285@6.[206,1381,148,725]" captionTargetPageId="6" captionText="Fig. 6. The multiple alignment of the CYP74L1, CYP74L2, and CYP74L3 sequences of S. moellendorffii with other CYP74s described earlier. Conservative structures are marked as follows: the I-helix groove region (SRS-4) is numbered 16, two positions after the I-helix groove region are marked by ◆ symbol, the F/L toggle is marked by ▾ symbol." figureDoi="http://doi.org/10.5281/zenodo.8235362" httpUri="https://zenodo.org/record/8235362/files/figure.png" pageId="5" pageNumber="6">Fig. 6</figureCitation>
). All known DESs except the RaDES (
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74
<collectionCode id="9E90AE1C7A49D25FFABB306C5AB1DD2A" box="[1401,1418,594,613]" country="Ecuador" lsid="urn:lsid:biocol.org:col:14273" name="Universidad Central" pageId="5" pageNumber="6" type="Herbarium">Q</collectionCode>
1) have another residue instead of Phe at this position (
<figureCitation id="60BA2A5C7A49D25FFB3230505A1EDDCE" box="[1264,1317,622,641]" captionStart="Fig" captionStartId="6.[100,130,753,770]" captionTargetBox="[209,1377,152,722]" captionTargetId="figure-285@6.[206,1381,148,725]" captionTargetPageId="6" captionText="Fig. 6. The multiple alignment of the CYP74L1, CYP74L2, and CYP74L3 sequences of S. moellendorffii with other CYP74s described earlier. Conservative structures are marked as follows: the I-helix groove region (SRS-4) is numbered 16, two positions after the I-helix groove region are marked by ◆ symbol, the F/L toggle is marked by ▾ symbol." figureDoi="http://doi.org/10.5281/zenodo.8235362" httpUri="https://zenodo.org/record/8235362/files/figure.png" pageId="5" pageNumber="6">Fig. 6</figureCitation>
). Mutation at this site may alter the
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<specimenCount id="EE87FD507A49D25FFBC130B45B7CDDD2" box="[1027,1095,650,669]" pageId="5" pageNumber="6" type="generic" typeStatus="type">74 type</specimenCount>
of catalysis. So, the
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295I mutant form of LeAOS3 (
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74
<collectionCode id="9E90AE1C7A49D25FFC0D30985CE5DDF6" box="[975,990,678,697]" country="Denmark" name="University of Copenhagen" pageId="5" pageNumber="6" type="Herbarium">C</collectionCode>
3) possessed HPL activity (
<bibRefCitation id="9C104B287A49D25FFB2030985AFADDF6" author="Toporkova, Y. Y. &amp; Gogolev, Y. V. &amp; Mukhtarova, L. S. &amp; Grechkin, A. N." box="[1250,1473,678,697]" pageId="5" pageNumber="6" pagination="3423 - 3428" refId="ref15689" refString="Toporkova, Y. Y., Gogolev, Y. V., Mukhtarova, L. S., Grechkin, A. N., 2008. Determinants governing the CYP 74 catalysis: conversion of allene oxide synthase into hydroperoxide lyase by site-directed mutagenesis. FEBS Lett. 582, 3423 - 3428. https: // doi. org / 10.1016 / j. febslet. 2008.09.005." type="journal article" year="2008">Toporkova et al., 2008</bibRefCitation>
).
<collectionCode id="9E90AE1C7A49D25FFCF030FC5C60DD9A" box="[818,859,706,725]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="5" pageNumber="6" type="Herbarium">CYP</collectionCode>
74
<taxonomicName id="3F814D5A7A49D25FFCAD30FC5CEADD9A" box="[879,977,706,725]" class="Alphaproteobacteria" family="Methylobacteriaceae" genus="Methylobacterium" kingdom="Bacteria" order="Rhizobiales" pageId="5" pageNumber="6" phylum="Proteobacteria" rank="species" species="enzymes">L enzymes</taxonomicName>
have a substitution of this conservative phenylalanine with other residue valine (
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74
<collectionCode id="9E90AE1C7A49D25FFB4D30E05BA6DDBE" box="[1167,1181,734,753]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="5" pageNumber="6" type="Herbarium">L</collectionCode>
1) or methionine (
<collectionCode id="9E90AE1C7A49D25FFA8930E05A4DDDBE" box="[1355,1398,734,753]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="5" pageNumber="6" type="Herbarium">CYP</collectionCode>
74
<collectionCode id="9E90AE1C7A49D25FFA4930E05AA3DDBE" box="[1419,1432,734,753]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="5" pageNumber="6" type="Herbarium">L</collectionCode>
2 and
<collectionCode id="9E90AE1C7A49D25FFCF030C75C64DC43" box="[818,863,761,780]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="5" pageNumber="6" type="Herbarium">CYP</collectionCode>
74
<collectionCode id="9E90AE1C7A49D25FFCB730C75CB8DC43" box="[885,899,761,780]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="5" pageNumber="6" type="Herbarium">L</collectionCode>
3).
</paragraph>
<paragraph id="F83E36D97A49D25FFCF0310F5C86DC0B" blockId="5.[818,957,817,836]" box="[818,957,817,836]" pageId="5" pageNumber="6">
<heading id="A37681B57A49D25FFCF0310F5C86DC0B" bold="true" box="[818,957,817,836]" fontSize="36" level="1" pageId="5" pageNumber="6" reason="1">
<emphasis id="CAF5EACB7A49D25FFCF0310F5C86DC0B" bold="true" box="[818,957,817,836]" pageId="5" pageNumber="6">3. Discussion</emphasis>
</heading>
</paragraph>
<paragraph id="F83E36D97A49D25FFC9331575B66DA51" blockId="5.[818,1488,873,1506]" pageId="5" pageNumber="6">
Data obtained indicated that the recombinant
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74
<collectionCode id="9E90AE1C7A49D25FFA9A31575A5DDC33" box="[1368,1382,873,892]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="5" pageNumber="6" type="Herbarium">L</collectionCode>
1,
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74
<collectionCode id="9E90AE1C7A49D25FFA7A31575AFEDC33" box="[1464,1477,873,892]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="5" pageNumber="6" type="Herbarium">L</collectionCode>
2 and
<collectionCode id="9E90AE1C7A49D25FFC9B31BB5CBEDCD7" box="[857,901,901,920]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="5" pageNumber="6" type="Herbarium">CYP</collectionCode>
74
<collectionCode id="9E90AE1C7A49D25FFC5931BB5C92DCD7" box="[923,937,901,920]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="5" pageNumber="6" type="Herbarium">L</collectionCode>
3, despite belonging to the same subfamily and sharing high homology, possess different catalytic activities. The
<collectionCode id="9E90AE1C7A49D25FFAF0319F5A67DCFB" box="[1330,1372,929,948]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="5" pageNumber="6" type="Herbarium">CYP</collectionCode>
74
<collectionCode id="9E90AE1C7A49D25FFAB0319F5A44DCFB" box="[1394,1407,929,948]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="5" pageNumber="6" type="Herbarium">L</collectionCode>
2 specifically exhibited
<collectionCode id="9E90AE1C7A49D25FFC0C31835CCCDC9F" box="[974,1015,957,976]" pageId="5" pageNumber="6">AOS</collectionCode>
activity. In contrast,
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74
<collectionCode id="9E90AE1C7A49D25FFACC31835A27DC9F" box="[1294,1308,957,976]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="5" pageNumber="6" type="Herbarium">L</collectionCode>
1 possessed mainly HPL activity towards its preferred substrates, 13-hydroperoxides. Conversely, the 9-
<collectionCode id="9E90AE1C7A49D25FFC2031CB5B1BDB47" box="[994,1056,1013,1032]" pageId="5" pageNumber="6">HPOD</collectionCode>
and 9-
<collectionCode id="9E90AE1C7A49D25FFBA531CB5B9EDB47" box="[1127,1189,1013,1032]" pageId="5" pageNumber="6">HPOT</collectionCode>
, relatively poor substrates for
<collectionCode id="9E90AE1C7A49D25FFCF0362F5C64DB6B" box="[818,863,1041,1060]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="5" pageNumber="6" type="Herbarium">CYP</collectionCode>
74
<collectionCode id="9E90AE1C7A49D25FFCB7362F5CB8DB6B" box="[885,899,1041,1060]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="5" pageNumber="6" type="Herbarium">L</collectionCode>
1, were converted largely to
<collectionCode id="9E90AE1C7A49D25FFB47362F5B95DB6B" box="[1157,1198,1041,1060]" pageId="5" pageNumber="6">AOS</collectionCode>
products. The
<collectionCode id="9E90AE1C7A49D25FFAFA362F5A5ADB6B" box="[1336,1377,1041,1060]" pageId="5" pageNumber="6">AOS</collectionCode>
products of both
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74
<collectionCode id="9E90AE1C7A49D25FFC6836125C83DB70" box="[938,952,1068,1087]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="5" pageNumber="6" type="Herbarium">L</collectionCode>
1 and
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74
<collectionCode id="9E90AE1C7A49D25FFBF536125B7FDB70" box="[1079,1092,1068,1087]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="5" pageNumber="6" type="Herbarium">L</collectionCode>
2 were represented mainly by α ketols which are products of spontaneous hydrolysis of corresponding allene oxides, short-living primary
<collectionCode id="9E90AE1C7A49D25FFB86365A5B56DB38" box="[1092,1133,1124,1143]" pageId="5" pageNumber="6">AOS</collectionCode>
products. Besides, the conversion of 13-
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led to a substantial yield of the cyclopentenone
<emphasis id="CAF5EACB7A49D25FFA9636BE5A50DBDC" bold="true" box="[1364,1387,1152,1171]" italics="true" pageId="5" pageNumber="6">cis</emphasis>
-12-OPDA. Unlike
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74
<collectionCode id="9E90AE1C7A49D25FFC7A36A25CFDDBE0" box="[952,966,1180,1199]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="5" pageNumber="6" type="Herbarium">L</collectionCode>
1 and
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74
<collectionCode id="9E90AE1C7A49D25FFBFF36A25B71DBE0" box="[1085,1098,1180,1199]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="5" pageNumber="6" type="Herbarium">L</collectionCode>
2,
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74
<collectionCode id="9E90AE1C7A49D25FFB5C36A25B90DBE0" box="[1182,1195,1180,1199]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="5" pageNumber="6" type="Herbarium">L</collectionCode>
3 exhibited quite low HPL/
<collectionCode id="9E90AE1C7A49D25FFA6536A25AF4DBE0" box="[1447,1487,1180,1199]" pageId="5" pageNumber="6">EAS</collectionCode>
activity towards 13-
<collectionCode id="9E90AE1C7A49D25FFC3836865B07DB84" box="[1018,1084,1208,1227]" pageId="5" pageNumber="6">HPOD</collectionCode>
, 9-
<collectionCode id="9E90AE1C7A49D25FFB9F36865BA0DB84" box="[1117,1179,1208,1227]" pageId="5" pageNumber="6">HPOT</collectionCode>
, and 9-
<collectionCode id="9E90AE1C7A49D25FFB2F36865A10DB84" box="[1261,1323,1208,1227]" pageId="5" pageNumber="6">HPOD</collectionCode>
(Supplementary
<figureCitation id="60BA2A5C7A49D25FFCF036EA5C43DBA8" box="[818,888,1236,1255]" captionStart="Fig" captionStartId="1.[100,130,1913,1930]" captionTargetBox="[209,1379,557,1882]" captionTargetId="figure-277@1.[207,1381,554,1885]" captionTargetPageId="1" captionText="Fig. 1. The multiple alignment of the CYP74L1, CYP74L2, and CYP74L3 sequences of S. moellendorffii. Conservative structures are marked as follows: the I-helix groove region (SRS-4) is numbered 16, two positions after the I-helix groove region are marked by ▾ symbol, the F/L toggle, the ERR-triad, the PPV domain, and the cysteinyl ligand are marked by ◆, ●, □, and ◊ symbols, respectively." figureDoi="http://doi.org/10.5281/zenodo.8235352" httpUri="https://zenodo.org/record/8235352/files/figure.png" pageId="5" pageNumber="6">Fig. S1</figureCitation>
) and was fully inactive towards 13-
<collectionCode id="9E90AE1C7A49D25FFB2A36EA5A13DBA8" box="[1256,1320,1236,1255]" pageId="5" pageNumber="6">HPOT</collectionCode>
. Low activity of
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74
<collectionCode id="9E90AE1C7A49D25FFCB036CE5C44DA4C" box="[882,895,1264,1283]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="5" pageNumber="6" type="Herbarium">L</collectionCode>
3 may be caused by the deletion of sixteen amino acids in the middle of the sequence (
<figureCitation id="60BA2A5C7A49D25FFBD837355B6BDA51" box="[1050,1104,1291,1310]" captionStart="Fig" captionStartId="1.[100,130,1913,1930]" captionTargetBox="[209,1379,557,1882]" captionTargetId="figure-277@1.[207,1381,554,1885]" captionTargetPageId="1" captionText="Fig. 1. The multiple alignment of the CYP74L1, CYP74L2, and CYP74L3 sequences of S. moellendorffii. Conservative structures are marked as follows: the I-helix groove region (SRS-4) is numbered 16, two positions after the I-helix groove region are marked by ▾ symbol, the F/L toggle, the ERR-triad, the PPV domain, and the cysteinyl ligand are marked by ◆, ●, □, and ◊ symbols, respectively." figureDoi="http://doi.org/10.5281/zenodo.8235352" httpUri="https://zenodo.org/record/8235352/files/figure.png" pageId="5" pageNumber="6">Fig. 1</figureCitation>
).
</paragraph>
<paragraph id="F83E36D97A49D25DFC9337195D57DFE8" blockId="5.[818,1488,873,1506]" lastBlockId="7.[100,770,148,502]" lastPageId="7" lastPageNumber="8" pageId="5" pageNumber="6">
The
<collectionCode id="9E90AE1C7A49D25FFCBF37195C9DDA75" box="[893,934,1319,1338]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="5" pageNumber="6" type="Herbarium">CYP</collectionCode>
74Ls expand the list of characterized enzymes of oxylipin biosynthesis in spikemoss. The
<taxonomicName id="3F814D5A7A49D25FFB90377D5BD8DA19" box="[1106,1251,1347,1366]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="moellendorffii">
<emphasis id="CAF5EACB7A49D25FFB90377D5BD8DA19" bold="true" box="[1106,1251,1347,1366]" italics="true" pageId="5" pageNumber="6">S. moellendorffii</emphasis>
</taxonomicName>
CYPome includes at least two DESs, i.e. SmDES1 (
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74
<collectionCode id="9E90AE1C7A49D25FFBA137615B43DA3D" box="[1123,1144,1375,1394]" country="Germany" lsid="urn:lsid:biocol.org:col:15637" name="Botanische Staatssammlung München" pageId="5" pageNumber="6" type="Herbarium">M</collectionCode>
1) and SmDES2 (
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74
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3) (
<bibRefCitation id="9C104B287A49D25FFA4D37615CA1DAC1" author="Gorina, S. S. &amp; Toporkova, Y. Y. &amp; Mukhtarova, L. S. &amp; Smirnova, E. O. &amp; Chechetkin, I. R. &amp; Khairutdinov, B. I. &amp; Gogolev, Y. V. &amp; Grechkin, A. N." pageId="5" pageNumber="6" pagination="301 - 309" refId="ref13051" refString="Gorina, S. S., Toporkova, Y. Y., Mukhtarova, L. S., Smirnova, E. O., Chechetkin, I. R., Khairutdinov, B. I., Gogolev, Y. V., Grechkin, A. N., 2016. Oxylipin biosynthesis in spikemoss Selaginella moellendorffii: molecular cloning and identification of divinyl ether synthases CYP 74 M 1 and CYP 74 M 3. Biochim. Biophys. Acta 1861, 301 - 309. https: // doi. org / 10.1016 / j. bbalip. 2016.01.001." type="journal article" year="2016">Gorina et al., 2016</bibRefCitation>
), producing divinyl ethers
<emphasis id="CAF5EACB7A49D25FFB5737455BC1DAC1" bold="true" box="[1173,1274,1403,1422]" pageId="5" pageNumber="6">
<collectionCode id="9E90AE1C7A49D25FFB5737455B8EDAC1" box="[1173,1205,1403,1422]" country="Hungary" lsid="urn:lsid:biocol.org:col:15158" name="Debrecen University" pageId="5" pageNumber="6" type="Herbarium">DE</collectionCode>
1
<collectionCode id="9E90AE1C7A49D25FFB1337455BCBDAC1" box="[1233,1264,1403,1422]" country="Hungary" lsid="urn:lsid:biocol.org:col:15158" name="Debrecen University" pageId="5" pageNumber="6" type="Herbarium">DE</collectionCode>
6
</emphasis>
(
<figureCitation id="60BA2A5C7A49D25FFAC437455A01DAC1" box="[1286,1338,1403,1422]" captionStart="Fig" captionStartId="5.[100,130,1888,1905]" captionTargetBox="[208,1379,1560,1859]" captionTargetId="figure-973@5.[206,1381,1558,1861]" captionTargetPageId="5" captionText="Fig. 5. The TIC chromatogram of oxylipins (Me/TMS) from the aerial parts of S. moellendorffii plants. DE1, (ω5Z)-etheroleic acid; DE2, etheroleic acid; DE3, (11Z)- etheroleic acid; DE4, etherolenic acid; DE5, (ω5Z)-etherolenic acid; DE6, (11Z)-etherolenic acid; 5, 11-hydroxy-12,13-epoxy-9-octadecenoic acid; 5a, 11-hydroxy- 12,13-epoxy-9,15-octadecadienoic acid; 10, eicosanoic acid; 11, 13-ketooctadecadienoic acid; 12, epimeric 9-hydroxy-12,13-epoxy-10-octadecenoic acid; 12a, epimeric 9-hydroxy-12,13-epoxy-10,15-octadecadienoic acid. Additionally, 13-HOD, as well as cis and trans isomers of 12-OPDA were detected." figureDoi="http://doi.org/10.5281/zenodo.8235360" httpUri="https://zenodo.org/record/8235360/files/figure.png" pageId="5" pageNumber="6">Fig. 5</figureCitation>
). Divinyl ethers oxylipins play self-defensive and antipathogenic roles in plants (
<bibRefCitation id="9C104B287A49D25FFA5037A95CA5DA89" author="Weber, H. &amp; Chetelat, A. &amp; Caldelari, D. &amp; Farmer, E. E." pageId="5" pageNumber="6" pagination="485 - 493" refId="ref16584" refString="Weber, H., Chetelat, A., Caldelari, D., Farmer, E. E., 1999. Divinyl ether fatty acid synthesis in late blight-diseased potato leaves. Plant Cell 11, 485 - 493. https: // doi. org / 10.1105 / tpc. 11.3.485." type="journal article" year="1999">Weber et al., 1999</bibRefCitation>
;
<bibRefCitation id="9C104B287A49D25FFC69378D5B05DA89" author="Grechkin, A. N." box="[939,1086,1459,1478]" pageId="5" pageNumber="6" pagination="457 - 470" refId="ref13350" refString="Grechkin, A. N., 2002. Hydroperoxide lyase and divinyl ether synthase. Prostag. Other Lipid Mediat. 68 - 69, 457 - 470. https: // doi. org / 10.1016 / s 0090 - 6980 (02) 00048 - 5." type="journal article" year="2002">Grechkin, 2002</bibRefCitation>
; Gran´er et al., 2003;
<bibRefCitation id="9C104B287A49D25FFAC9378D5C59DAAD" author="Cowley, T. &amp; Walters, D." pageId="5" pageNumber="6" pagination="572 - 576" refId="ref12547" refString="Cowley, T., Walters, D., 2005. Local and systemic effects of oxylipins on powdery mildew infection in barley. Pest Manag. Sci. 61, 572 - 576. https: // doi. org / 10.1002 / ps. 1026." type="journal article" year="2005">Cowley and Walters, 2005</bibRefCitation>
;
<bibRefCitation id="9C104B287A49D25FFCAE37F15B32DAAD" author="Prost, I. &amp; Dhondt, S. &amp; Rothe, G. &amp; Vicente, J. &amp; Rodriguez, M. J. &amp; Kift, N. &amp; Carbonne, F. &amp; Griffiths, G. &amp; Esquerre-Tugaye, M. - T. &amp; Rosahl, S. &amp; Castresana, C. &amp; Hamberg, M. &amp; Fournier, J." box="[876,1033,1487,1506]" pageId="5" pageNumber="6" pagination="1902 - 1913" refId="ref14995" refString="Prost, I., Dhondt, S., Rothe, G., Vicente, J., Rodriguez, M. J., Kift, N., Carbonne, F., Griffiths, G., Esquerre-Tugaye, M. - T., Rosahl, S., Castresana, C., Hamberg, M., Fournier, J., 2005. Evaluation of the antimicrobial activities of plant oxylipins supports their involvement in defense against pathogens. Plant Physiol. 139, 1902 - 1913. https: // doi. org / 10.1104 / pp. 105.066274." type="journal article" year="2005">Prost et al., 2005</bibRefCitation>
;
<bibRefCitation id="9C104B287A49D25FFBD637F15BCBDAAD" author="Toporkova, Y. Y. &amp; Smirnova, E. O. &amp; Gorina, S. S. &amp; Mukhtarova, L. S. &amp; Grechkin, A. N." box="[1044,1264,1487,1506]" pageId="5" pageNumber="6" pagination="73 - 82" refId="ref16051" refString="Toporkova, Y. Y., Smirnova, E. O., Gorina, S. S., Mukhtarova, L. S., Grechkin, A. N., 2018 a. Detection of the first higher plant epoxyalcohol synthase: molecular cloning and characterisation of the CYP 74 M 2 enzyme of spikemoss Selaginella moellendorffii. Phytochemistry 156, 73 - 82. https: // doi. org / 10.1016 / j. phytochem. 2018.08.010." type="journal article" year="2018">Toporkova et al., 2018a</bibRefCitation>
;
<bibRefCitation id="9C104B287A49D25FFB3937F15AFADAAD" author="Deboever, E. &amp; Deleu, M. &amp; Mongrand, S. &amp; Lins, L. &amp; Fauconnier, M. L." box="[1275,1473,1487,1506]" pageId="5" pageNumber="6" pagination="22 - 34" refId="ref12596" refString="Deboever, E., Deleu, M., Mongrand, S., Lins, L., Fauconnier, M. L., 2020. Plant-pathogen interactions: underestimated roles of phyto-oxylipins. Trends Plant Sci. 25, 22 - 34. https: // doi. org / 10.1016 / j. tplants. 2019.09.009." type="journal article" year="2020">Deboever et al., 2020</bibRefCitation>
). Moreover, expression of
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genes is increased in response to pathogenic microorganisms (
<bibRefCitation id="9C104B287A4AD25CFE8631475EC3DCC2" author="Weber, H. &amp; Chetelat, A. &amp; Caldelari, D. &amp; Farmer, E. E." box="[324,504,889,909]" pageId="6" pageNumber="7" pagination="485 - 493" refId="ref16584" refString="Weber, H., Chetelat, A., Caldelari, D., Farmer, E. E., 1999. Divinyl ether fatty acid synthesis in late blight-diseased potato leaves. Plant Cell 11, 485 - 493. https: // doi. org / 10.1105 / tpc. 11.3.485." type="journal article" year="1999">Weber et al., 1999</bibRefCitation>
;
<bibRefCitation id="9C104B287A4AD25CFDC431445DFEDCC2" author="Stumpe, M. &amp; Kandzia, R. &amp; Rosahl, S. &amp; Feussner, I." box="[518,709,889,909]" pageId="6" pageNumber="7" pagination="371 - 376" refId="ref15469" refString="Stumpe, M., Kandzia, R., G ¨ obel, C., Rosahl, S., Feussner, I., 2001. A pathogen-inducible divinyl ether synthase (CYP 74 D) from elicitor-treated potato suspension cells. FEBS Lett. 507, 371 - 376. https: // doi. org / 10.1016 / s 0014 - 5793 (01) 03019 - 8." type="journal article" year="2001">Stumpe et al., 2001</bibRefCitation>
;
<bibRefCitation id="9C104B287A4AD25CFD1131445E1FDCE6" author="Fammartino, A. &amp; Cardinale, F. &amp; Mene-Saffrane, L. &amp; Fournier, J. &amp; Feussner, I. &amp; Esquerre-Tugaye, M. T." pageId="6" pageNumber="7" pagination="378 - 388" refId="ref12658" refString="Fammartino, A., Cardinale, F., G ¨ obel, C., Mene-Saffrane, L., Fournier, J., Feussner, I., Esquerre-Tugaye, M. T., 2007. Characterization of a divinyl ether biosynthetic pathway specifically associated with pathogenesis in tobacco. Plant Physiol. 143, 378 - 388. https: // doi. org / 10.1104 / pp. 106.087304." type="journal article" year="2007">Fammartino et al., 2007</bibRefCitation>
), viral attack (
<bibRefCitation id="9C104B287A4AD25CFE7631AB5D09DCE6" author="Nelson, D. R." box="[436,562,917,937]" pageId="6" pageNumber="7" pagination="14 - 18" refId="ref14623" refString="Nelson, D. R., 2011. Progress in tracing the evolutionary paths of cytochrome P 450. Biochim. Biophys. Acta 1814, 14 - 18. https: // doi. org / 10.1016 / j. bbapap. 2010.08.008." type="journal article" year="2011">Nelson, 2011</bibRefCitation>
) or elicitor treatment (Gobel ¨et al., 2001). The epoxyalcohols
<emphasis id="CAF5EACB7A4AD25CFE1D318F5ED0DC8B" bold="true" box="[479,491,945,964]" pageId="6" pageNumber="7">5</emphasis>
,
<emphasis id="CAF5EACB7A4AD25CFE3A318F5D2BDC8B" bold="true" box="[504,528,945,964]" pageId="6" pageNumber="7">5a</emphasis>
,
<emphasis id="CAF5EACB7A4AD25CFDDF318F5D0DDC8B" bold="true" box="[541,566,945,964]" pageId="6" pageNumber="7">12</emphasis>
, and
<emphasis id="CAF5EACB7A4AD25CFDAE318F5DABDC8B" bold="true" box="[620,656,945,964]" pageId="6" pageNumber="7">12a</emphasis>
can be synthesized by SmEAS (
<collectionCode id="9E90AE1C7A4AD25CFEE231F35E76DCAF" box="[288,333,973,992]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="6" pageNumber="7" type="Herbarium">CYP</collectionCode>
74
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2,
<bibRefCitation id="9C104B287A4AD25CFE4931F35D53DCAF" author="Toporkova, Y. Y. &amp; Smirnova, E. O. &amp; Gorina, S. S. &amp; Mukhtarova, L. S. &amp; Grechkin, A. N." box="[395,616,973,993]" pageId="6" pageNumber="7" pagination="73 - 82" refId="ref16051" refString="Toporkova, Y. Y., Smirnova, E. O., Gorina, S. S., Mukhtarova, L. S., Grechkin, A. N., 2018 a. Detection of the first higher plant epoxyalcohol synthase: molecular cloning and characterisation of the CYP 74 M 2 enzyme of spikemoss Selaginella moellendorffii. Phytochemistry 156, 73 - 82. https: // doi. org / 10.1016 / j. phytochem. 2018.08.010." type="journal article" year="2018">Toporkova et al., 2018a</bibRefCitation>
). Epoxyalcohols and products of their hydrolysis, trihydroxy acids, were shown to participate in the defence responses against phytopathogens (
<bibRefCitation id="9C104B287A4AD25CFD5C363B5FAFDB7B" author="Kato, T. &amp; Yamaguchi, Y. &amp; Abe, N." pageId="6" pageNumber="7" pagination="2357 - 2360" refId="ref14076" refString="Kato, T., Yamaguchi, Y., Abe, N., et al., 1985. Structure and synthesis of unsaturated trihydroxy C 18 fatty: acids in rice plants suffering from rice blast disease. Tetrahedron Lett. 26, 2357 - 2360. https: // doi. org / 10.1021 / acs. jafc. 8 b 05857." type="journal article" year="1985">Kato et al., 1985</bibRefCitation>
;
<bibRefCitation id="9C104B287A4AD25CFF5C361F5E01DB7B" author="Prost, I. &amp; Dhondt, S. &amp; Rothe, G. &amp; Vicente, J. &amp; Rodriguez, M. J. &amp; Kift, N. &amp; Carbonne, F. &amp; Griffiths, G. &amp; Esquerre-Tugaye, M. - T. &amp; Rosahl, S. &amp; Castresana, C. &amp; Hamberg, M. &amp; Fournier, J." box="[158,314,1057,1076]" pageId="6" pageNumber="7" pagination="1902 - 1913" refId="ref14995" refString="Prost, I., Dhondt, S., Rothe, G., Vicente, J., Rodriguez, M. J., Kift, N., Carbonne, F., Griffiths, G., Esquerre-Tugaye, M. - T., Rosahl, S., Castresana, C., Hamberg, M., Fournier, J., 2005. Evaluation of the antimicrobial activities of plant oxylipins supports their involvement in defense against pathogens. Plant Physiol. 139, 1902 - 1913. https: // doi. org / 10.1104 / pp. 105.066274." type="journal article" year="2005">Prost et al., 2005</bibRefCitation>
).
<emphasis id="CAF5EACB7A4AD25CFE8E361F5E5CDB7B" bold="true" box="[332,359,1057,1076]" italics="true" pageId="6" pageNumber="7">Cis</emphasis>
- and
<emphasis id="CAF5EACB7A4AD25CFE5B361F5EFDDB7B" bold="true" box="[409,454,1057,1076]" italics="true" pageId="6" pageNumber="7">trans</emphasis>
-isomers of 12-oxo-PDA, as well as
<emphasis id="CAF5EACB7A4AD25CFFA636035F47DB1F" bold="true" box="[100,124,1085,1104]" italics="true" pageId="6" pageNumber="7">iso</emphasis>
-12-oxo-PDA, can be synthesized by SmAOS1 (
<collectionCode id="9E90AE1C7A4AD25CFDE936035D6CDB1F" box="[555,599,1085,1104]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="6" pageNumber="7" type="Herbarium">CYP</collectionCode>
74
<collectionCode id="9E90AE1C7A4AD25CFDAF36035D40DB1F" box="[621,635,1085,1104]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="6" pageNumber="7" type="Herbarium">L</collectionCode>
2) described in the present report or other putative AOSs, i.e.
<collectionCode id="9E90AE1C7A4AD25CFDFC36675D56DB23" box="[574,621,1113,1132]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="6" pageNumber="7" type="Herbarium">CYP</collectionCode>
74J1,
<collectionCode id="9E90AE1C7A4AD25CFD6136675DEBDB23" box="[675,720,1113,1132]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="6" pageNumber="7" type="Herbarium">CYP</collectionCode>
74K1,
<collectionCode id="9E90AE1C7A4AD25CFFA6364B5FB4DBC7" box="[100,143,1141,1160]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="6" pageNumber="7" type="Herbarium">CYP</collectionCode>
74K2, or the before characterized SmAOS2 (
<collectionCode id="9E90AE1C7A4AD25CFD8A364B5D4FDBC7" box="[584,628,1141,1160]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="6" pageNumber="7" type="Herbarium">CYP</collectionCode>
74K3) (Pratiwi et al., 2017). 12-oxo-PDA appears to play a significant role in mediating resistance to pathogens and pests such as
<taxonomicName id="3F814D5A7A4AD25CFB7631475C51DCE6" authority="(Scalschi et al., 2015)" baseAuthorityName="Scalschi" baseAuthorityYear="2015" class="Sordariomycetes" family="Clavicipitaceae" genus="Botrytis" kingdom="Fungi" order="Hypocreales" pageId="6" pageNumber="7" phylum="Ascomycota" rank="species" species="cinerea">
<emphasis id="CAF5EACB7A4AD25CFB7631475A05DCC3" bold="true" box="[1204,1342,889,908]" italics="true" pageId="6" pageNumber="7">Botrytis cinerea</emphasis>
(
<bibRefCitation id="9C104B287A4AD25CFA8931475C59DCE7" author="Scalschi, L. &amp; Sanmartin, M. &amp; Troncho, P. &amp; Agustin, P. &amp; Vicedo, B." pageId="6" pageNumber="7" pagination="304 - 315" refId="ref15208" refString="Scalschi, L., Sanmartin, M., Camanes t, G., Troncho, P., Sanchez-Serrano´, J. J., Garcia- Agustin, P., Vicedo, B., 2015. Silencing of OPR 3 in tomato reveals the role of OPDA in callose deposition during the activation of defense responses against Botrytis cinerea. Plant J. 81, 304 - 315. https: // doi. org / 10.1111 / tpj. 12728." type="journal article" year="2015">Scalschi et al., 2015</bibRefCitation>
)
</taxonomicName>
, beet armyworm (
<taxonomicName id="3F814D5A7A4AD25CFBD831AB5B85DCE7" baseAuthorityName="Hubner" baseAuthorityYear="1808" box="[1050,1214,917,936]" class="Insecta" family="Noctuidae" genus="Spodoptera" kingdom="Animalia" order="Lepidoptera" pageId="6" pageNumber="7" phylum="Arthropoda" rank="species" species="exigua">
<emphasis id="CAF5EACB7A4AD25CFBD831AB5B85DCE7" bold="true" box="[1050,1214,917,936]" italics="true" pageId="6" pageNumber="7">Spodoptera exigua</emphasis>
</taxonomicName>
larvae) (
<bibRefCitation id="9C104B287A4AD25CFAD731AB5AF2DCE6" author="Bosch, M. &amp; Berger, S. &amp; Schaller, A. &amp; Stintzi, A." box="[1301,1481,917,937]" pageId="6" pageNumber="7" pagination="257" refId="ref11487" refString="Bosch, M., Berger, S., Schaller, A., Stintzi, A., 2014 a. Jasmonate-dependent induction of polyphenol oxidase activity in tomato foliage is important for defense against Spodoptera exigua but not against Manduca sexta. BMC Plant Biol. 14, 257. https: // doi. org / 10.1186 / s 12870 - 014 - 0257 - 8." type="journal article" year="2014">
Bosch et al., 2014
<bibRefCitation id="9C104B287A4AD25CFA7D31A85AF2DCE6" author="Stintzi, A." box="[1471,1481,918,937]" pageId="6" pageNumber="7" pagination="396 - 410" refId="ref11590" refString="Stintzi, A., 2014 b. Jasmonic acid and its precursor 12 - oxophytodienoic acid control different aspects of constitutive and induced herbivore defenses in tomato. Plant Physiol. 166, 396 - 410. https: // doi. org / 10.1104 / pp. 114.237388." type="journal article" year="2014">a</bibRefCitation>
</bibRefCitation>
, 2014b), brown planthopper (
<taxonomicName id="3F814D5A7A4AD25CFB87318F5BD0DC8B" baseAuthorityName="Stal" baseAuthorityYear="1854" box="[1093,1259,945,964]" class="Insecta" family="Delphacidae" genus="Nilaparvata" kingdom="Animalia" order="Hemiptera" pageId="6" pageNumber="7" phylum="Arthropoda" rank="species" species="lugens">
<emphasis id="CAF5EACB7A4AD25CFB87318F5BD0DC8B" bold="true" box="[1093,1259,945,964]" italics="true" pageId="6" pageNumber="7">Nilaparvata lugens</emphasis>
</taxonomicName>
) (
<bibRefCitation id="9C104B287A4AD25CFAC3318F5AA3DC8B" author="Guo, H. M. &amp; Li, H. C. &amp; Zhou, S. R. &amp; Xue, H. W. &amp; Miao, X. X." box="[1281,1432,945,965]" pageId="6" pageNumber="7" pagination="1683 - 1692" refId="ref13841" refString="Guo, H. M., Li, H. C., Zhou, S. R., Xue, H. W., Miao, X. X., 2014. Cis - 12 - oxo-phytodienoic acid stimulates rice defense response to a piercing-sucking insect. Mol. Plant 7, 1683 - 1692. https: // doi. org / 10.1093 / mp / ssu 098." type="journal article" year="2014">Guo et al., 2014</bibRefCitation>
), and corn leaf aphid (
<taxonomicName id="3F814D5A7A4AD25CFC1A31F35B9FDCAF" baseAuthorityName="Fitch" baseAuthorityYear="1856" box="[984,1188,973,992]" class="Insecta" family="Aphididae" genus="Rhopalosiphum" kingdom="Animalia" order="Hemiptera" pageId="6" pageNumber="7" phylum="Arthropoda" rank="species" species="maidis">
<emphasis id="CAF5EACB7A4AD25CFC1A31F35B9FDCAF" bold="true" box="[984,1188,973,992]" italics="true" pageId="6" pageNumber="7">Rhopalosiphum maidis</emphasis>
</taxonomicName>
) (
<bibRefCitation id="9C104B287A4AD25CFB7F31F35A44DCAF" author="Varsani, S. &amp; Grover, S. &amp; Zhou, S. &amp; Koch, K. G. &amp; Huang, P. C. &amp; Kolomiets, M. V. &amp; Williams, W. P. &amp; Heng-Moss, T. &amp; Sarath, G. &amp; Luthe, D. S. &amp; Jander, G. &amp; Louis, J." box="[1213,1407,973,993]" pageId="6" pageNumber="7" pagination="1402 - 1415" refId="ref16421" refString="Varsani, S., Grover, S., Zhou, S., Koch, K. G., Huang, P. C., Kolomiets, M. V., Williams, W. P., Heng-Moss, T., Sarath, G., Luthe, D. S., Jander, G., Louis, J., 2019. 12 - Oxophytodienoic acid acts as a regulator of maize defense against corn leaf aphid. Plant Physiol. 179, 1402 - 1415. https: // doi. org / 10.1104 / pp. 18.01472." type="journal article" year="2019">Varsani et al., 2019</bibRefCitation>
;
<bibRefCitation id="9C104B287A4AD25CFA4C31F35CA5DCB3" author="Grover, S. &amp; Versani, S. &amp; Kolomietx, M. V. &amp; Louis, J." pageId="6" pageNumber="7" pagination="63 - 66" refId="ref13781" refString="Grover, S., Versani, S., Kolomietx, M. V., Louis, J., 2020. Maize defense elicitor, 12 - oxophytodienoic acid, prolongs aphid salivation. Commun. Integr. Biol. 13, 63 - 66. https: // doi. org / 10.1080 / 19420889.2020.1763562." type="journal article" year="2020">Grover et al., 2020</bibRefCitation>
). The absence of HPL products in the
<taxonomicName id="3F814D5A7A4AD25CFACF31D75C66DB57" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="6" pageNumber="6" phylum="Tracheophyta" rank="subSpecies" species="moellendorffii" subSpecies="oxylipin">
<emphasis id="CAF5EACB7A4AD25CFACF31D75A9BDCB3" bold="true" box="[1293,1440,1001,1020]" italics="true" pageId="6" pageNumber="7">S. moellendorffii</emphasis>
oxylipin
</taxonomicName>
profile (
<figureCitation id="60BA2A5C7A4AD25CFC73363B5CD3DB57" box="[945,1000,1029,1048]" captionStart="Fig" captionStartId="5.[100,130,1888,1905]" captionTargetBox="[208,1379,1560,1859]" captionTargetId="figure-973@5.[206,1381,1558,1861]" captionTargetPageId="5" captionText="Fig. 5. The TIC chromatogram of oxylipins (Me/TMS) from the aerial parts of S. moellendorffii plants. DE1, (ω5Z)-etheroleic acid; DE2, etheroleic acid; DE3, (11Z)- etheroleic acid; DE4, etherolenic acid; DE5, (ω5Z)-etherolenic acid; DE6, (11Z)-etherolenic acid; 5, 11-hydroxy-12,13-epoxy-9-octadecenoic acid; 5a, 11-hydroxy- 12,13-epoxy-9,15-octadecadienoic acid; 10, eicosanoic acid; 11, 13-ketooctadecadienoic acid; 12, epimeric 9-hydroxy-12,13-epoxy-10-octadecenoic acid; 12a, epimeric 9-hydroxy-12,13-epoxy-10,15-octadecadienoic acid. Additionally, 13-HOD, as well as cis and trans isomers of 12-OPDA were detected." figureDoi="http://doi.org/10.5281/zenodo.8235360" httpUri="https://zenodo.org/record/8235360/files/figure.png" pageId="6" pageNumber="7">Fig. 5</figureCitation>
) suggests the absence of constitutive expression of
<emphasis id="CAF5EACB7A4AD25CFCF0361F5CBBDB7B" bold="true" box="[818,896,1057,1076]" italics="true" pageId="6" pageNumber="7">SmHPL1</emphasis>
(
<emphasis id="CAF5EACB7A4AD25CFC50361F5CD3DB7B" bold="true" box="[914,1000,1057,1076]" italics="true" pageId="6" pageNumber="7">
<collectionCode id="9E90AE1C7A4AD25CFC50361F5C80DB7B" box="[914,955,1057,1076]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="6" pageNumber="7" type="Herbarium">CYP</collectionCode>
74
<collectionCode id="9E90AE1C7A4AD25CFC13361F5CE4DB7B" box="[977,991,1057,1076]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="6" pageNumber="7" type="Herbarium">L</collectionCode>
1
</emphasis>
) gene. Presumably, it might be expressed under stress conditions. HPL-synthesized hexenals are also involved in herbivore resistance. In addition, the HPL branch yields the wound phytohormone traumatin and compounds with bactericidal, fungicidal or antioxidant properties (
<bibRefCitation id="9C104B287A4BD25DFE8132AA5D65DFE8" author="Pietryczuk, A. &amp; Czerpak, R." box="[323,606,148,167]" pageId="7" pageNumber="8" pagination="279 - 286" refId="ref14941" refString="Pietryczuk, A., Czerpak, R., 2011. Effect of traumatic acid on antioxidant activity in Chlorella vulgaris (Chlorophyceae). Plant Growth Regul. 65, 279 - 286. https: // doi. org / 10.1007 / s 10725 - 011 - 9599 - 5." type="journal article" year="2011">Pietryczuk and Czerpak, 2011</bibRefCitation>
).
</paragraph>
<caption id="ACFE66517A49D25FFFA6355E5A0FD8F2" ID-DOI="http://doi.org/10.5281/zenodo.8235360" ID-Zenodo-Dep="8235360" httpUri="https://zenodo.org/record/8235360/files/figure.png" pageId="5" pageNumber="6" startId="5.[100,130,1888,1905]" targetBox="[208,1379,1560,1859]" targetPageId="5" targetType="figure">
<paragraph id="F83E36D97A49D25FFFA6355E5A0FD8F2" blockId="5.[100,1487,1887,1981]" pageId="5" pageNumber="6">
<emphasis id="CAF5EACB7A49D25FFFA6355E5FA6D83F" bold="true" box="[100,157,1888,1905]" pageId="5" pageNumber="6">Fig. 5.</emphasis>
The TIC chromatogram of oxylipins (Me/TMS) from the aerial parts of
<taxonomicName id="3F814D5A7A49D25FFCC2355E5CBFD83F" box="[768,900,1887,1905]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="moellendorffii">
<emphasis id="CAF5EACB7A49D25FFCC2355E5CBFD83F" bold="true" box="[768,900,1887,1905]" italics="true" pageId="5" pageNumber="6">S. moellendorffii</emphasis>
</taxonomicName>
plants.
<emphasis id="CAF5EACB7A49D25FFC05355E5CD7D83E" bold="true" box="[967,1004,1888,1905]" pageId="5" pageNumber="6">DE1</emphasis>
, (ω5
<emphasis id="CAF5EACB7A49D25FFBD6355E5B24D83F" bold="true" box="[1044,1055,1888,1904]" italics="true" pageId="5" pageNumber="6">Z</emphasis>
)-etheroleic acid;
<emphasis id="CAF5EACB7A49D25FFB76355E5BE3D83E" bold="true" box="[1204,1240,1888,1905]" pageId="5" pageNumber="6">DE2</emphasis>
, etheroleic acid;
<emphasis id="CAF5EACB7A49D25FFAA9355E5AB4D83E" bold="true" box="[1387,1423,1888,1905]" pageId="5" pageNumber="6">DE3</emphasis>
, (11
<emphasis id="CAF5EACB7A49D25FFA75355E5AF9D83F" bold="true" box="[1463,1474,1888,1904]" italics="true" pageId="5" pageNumber="6">Z</emphasis>
)- etheroleic acid;
<emphasis id="CAF5EACB7A49D25FFF2F35475E29D8C5" bold="true" box="[237,274,1913,1930]" pageId="5" pageNumber="6">DE4</emphasis>
, etherolenic acid;
<emphasis id="CAF5EACB7A49D25FFE7035475EEDD8C6" bold="true" box="[434,470,1913,1929]" pageId="5" pageNumber="6">DE5</emphasis>
, (ω5
<emphasis id="CAF5EACB7A49D25FFDC235445D30D8C5" bold="true" box="[512,523,1914,1930]" italics="true" pageId="5" pageNumber="6">Z</emphasis>
)-etherolenic acid;
<emphasis id="CAF5EACB7A49D25FFD6E35475DEBD8C5" bold="true" box="[684,720,1913,1930]" pageId="5" pageNumber="6">DE6</emphasis>
, (11
<emphasis id="CAF5EACB7A49D25FFD3B35445C3FD8C5" bold="true" box="[761,772,1914,1930]" italics="true" pageId="5" pageNumber="6">Z</emphasis>
)-etherolenic acid;
<emphasis id="CAF5EACB7A49D25FFC6735475C8BD8C6" bold="true" box="[933,944,1913,1929]" pageId="5" pageNumber="6">5</emphasis>
, 11-hydroxy-12,13-epoxy-9-octadecenoic acid;
<emphasis id="CAF5EACB7A49D25FFA8435475A67D8C6" bold="true" box="[1350,1372,1913,1929]" pageId="5" pageNumber="6">5a</emphasis>
, 11-hydroxy- 12,13-epoxy-9,15-octadecadienoic acid;
<emphasis id="CAF5EACB7A49D25FFE0035AD5EE3D8EB" bold="true" box="[450,472,1939,1956]" pageId="5" pageNumber="6">10</emphasis>
, eicosanoic acid;
<emphasis id="CAF5EACB7A49D25FFDBB35AD5DB4D8EB" bold="true" box="[633,655,1939,1956]" pageId="5" pageNumber="6">11</emphasis>
, 13-ketooctadecadienoic acid;
<emphasis id="CAF5EACB7A49D25FFC6335AD5C8CD8EB" bold="true" box="[929,951,1939,1956]" pageId="5" pageNumber="6">12</emphasis>
, epimeric 9-hydroxy-12,13-epoxy-10-octadecenoic acid;
<emphasis id="CAF5EACB7A49D25FFA6B35AD5AF1D8EB" bold="true" box="[1449,1482,1939,1956]" pageId="5" pageNumber="6">12a</emphasis>
, epimeric 9-hydroxy-12,13-epoxy-10,15-octadecadienoic acid. Additionally, 13-HOD, as well as
<emphasis id="CAF5EACB7A49D25FFC5135925C9CD8F2" bold="true" box="[915,935,1964,1981]" italics="true" pageId="5" pageNumber="6">cis</emphasis>
and
<emphasis id="CAF5EACB7A49D25FFC1635925CC7D8F3" bold="true" box="[980,1020,1964,1980]" italics="true" pageId="5" pageNumber="6">trans</emphasis>
isomers of 12-OPDA were detected.
</paragraph>
</caption>
<caption id="ACFE66517A4AD25CFFA630CF5E27DC7A" ID-DOI="http://doi.org/10.5281/zenodo.8235362" ID-Zenodo-Dep="8235362" httpUri="https://zenodo.org/record/8235362/files/figure.png" pageId="6" pageNumber="7" startId="6.[100,130,753,770]" targetBox="[209,1377,152,722]" targetPageId="6" targetType="figure">
<paragraph id="F83E36D97A4AD25CFFA630CF5E27DC7A" blockId="6.[100,1487,752,821]" pageId="6" pageNumber="7">
<emphasis id="CAF5EACB7A4AD25CFFA630CF5FA6DC4D" bold="true" box="[100,157,753,770]" pageId="6" pageNumber="7">Fig. 6.</emphasis>
The multiple alignment of the CYP74L1, CYP74L2, and CYP74L3 sequences of
<taxonomicName id="3F814D5A7A4AD25CFC8130CF5CFCDC4E" box="[835,967,752,770]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="6" pageNumber="7" phylum="Tracheophyta" rank="species" species="moellendorffii">
<emphasis id="CAF5EACB7A4AD25CFC8130CF5CFCDC4E" bold="true" box="[835,967,752,770]" italics="true" pageId="6" pageNumber="7">S. moellendorffii</emphasis>
</taxonomicName>
with other CYP74s described earlier. Conservative structures are marked as follows: the I-helix groove region (SRS-4) is numbered 16, two positions after the I-helix groove region are marked by ◆ symbol, the F/L toggle is marked by ▾ symbol.
</paragraph>
</caption>
<caption id="ACFE66517A4AD25CFE3035925B78D8F2" ID-DOI="http://doi.org/10.5281/zenodo.8235364" ID-Zenodo-Dep="8235364" box="[498,1091,1964,1981]" httpUri="https://zenodo.org/record/8235364/files/figure.png" pageId="6" pageNumber="7" startId="6.[498,528,1964,1981]" targetBox="[209,1379,1217,1935]" targetPageId="6" targetType="figure">
<paragraph id="F83E36D97A4AD25CFE3035925B78D8F2" blockId="6.[498,1091,1964,1981]" box="[498,1091,1964,1981]" pageId="6" pageNumber="7">
<emphasis id="CAF5EACB7A4AD25CFE3035925D10D8F3" bold="true" box="[498,555,1964,1981]" pageId="6" pageNumber="7">Fig. 7.</emphasis>
The scheme of catalytic mechanisms of the CYP74
<taxonomicName id="3F814D5A7A4AD25CFC2035925B04D8F2" box="[994,1087,1964,1981]" class="Alphaproteobacteria" family="Methylobacteriaceae" genus="Methylobacterium" kingdom="Bacteria" order="Rhizobiales" pageId="6" pageNumber="7" phylum="Proteobacteria" rank="species" species="enzymes">L enzymes</taxonomicName>
.
</paragraph>
</caption>
<paragraph id="F83E36D97A4BD25DFF46328E5A55DE25" blockId="7.[100,770,148,502]" lastBlockId="7.[818,1488,148,502]" pageId="7" pageNumber="8">
The SmHPL1 (
<collectionCode id="9E90AE1C7A4BD25DFECD328E5E06DF8C" box="[271,317,176,195]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="7" pageNumber="8" type="Herbarium">CYP</collectionCode>
74
<collectionCode id="9E90AE1C7A4BD25DFE96328E5E59DF8C" box="[340,354,176,195]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="7" pageNumber="8" type="Herbarium">L</collectionCode>
1) is the first
<collectionCode id="9E90AE1C7A4BD25DFE21328E5D36DF8C" box="[483,525,176,195]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="7" pageNumber="8" type="Herbarium">CYP</collectionCode>
74 enzyme of
<taxonomicName id="3F814D5A7A4BD25DFD54328E5FA4DF91" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="moellendorffii">S. moellendorffii</taxonomicName>
possessing hydroperoxide lyase activity. Earlier it was suggested that CYPome of
<taxonomicName id="3F814D5A7A4BD25DFECA32D95EA5DFB5" box="[264,414,231,250]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="moellendorffii">
<emphasis id="CAF5EACB7A4BD25DFECA32D95EA5DFB5" bold="true" box="[264,414,231,250]" italics="true" pageId="7" pageNumber="8">S. moellendorffii</emphasis>
</taxonomicName>
does not contain any HPLs (
<bibRefCitation id="9C104B287A4BD25DFD0032D95FEFDE59" author="Gorina, S. S. &amp; Toporkova, Y. Y. &amp; Mukhtarova, L. S. &amp; Smirnova, E. O. &amp; Chechetkin, I. R. &amp; Khairutdinov, B. I. &amp; Gogolev, Y. V. &amp; Grechkin, A. N." pageId="7" pageNumber="8" pagination="301 - 309" refId="ref13051" refString="Gorina, S. S., Toporkova, Y. Y., Mukhtarova, L. S., Smirnova, E. O., Chechetkin, I. R., Khairutdinov, B. I., Gogolev, Y. V., Grechkin, A. N., 2016. Oxylipin biosynthesis in spikemoss Selaginella moellendorffii: molecular cloning and identification of divinyl ether synthases CYP 74 M 1 and CYP 74 M 3. Biochim. Biophys. Acta 1861, 301 - 309. https: // doi. org / 10.1016 / j. bbalip. 2016.01.001." type="journal article" year="2016">Gorina et al., 2016</bibRefCitation>
). This assumption was based on the peculiarities of catalytically essential domains of
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74s. Moreover, SmHPL1 (
<collectionCode id="9E90AE1C7A4BD25DFD6033215DEBDE7D" box="[674,720,287,306]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="7" pageNumber="8" type="Herbarium">CYP</collectionCode>
74
<collectionCode id="9E90AE1C7A4BD25DFD2433215DCFDE7D" box="[742,756,287,306]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="7" pageNumber="8" type="Herbarium">L</collectionCode>
1) presents one more example of a
<collectionCode id="9E90AE1C7A4BD25DFE6233055EF1DE01" box="[416,458,315,334]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="7" pageNumber="8" type="Herbarium">CYP</collectionCode>
74 enzyme exhibiting a different catalytic behaviour depending on substrate. Recently the dual function
<collectionCode id="9E90AE1C7A4BD25DFFA6334D5FB5DEC9" box="[100,142,371,390]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="7" pageNumber="8" type="Herbarium">CYP</collectionCode>
74
<collectionCode id="9E90AE1C7A4BD25DFF61334D5F8BDEC9" box="[163,176,371,390]" country="Denmark" name="University of Copenhagen" pageId="7" pageNumber="8" type="Herbarium">C</collectionCode>
HPL/EASs have been described (
<bibRefCitation id="9C104B287A4BD25DFDC1334D5DCFDEC9" author="Toporkova, Y. Y. &amp; Gorina, S. S. &amp; Bessolitsyna, E. K. &amp; Smirnova, E. O. &amp; Fatykhova, V. S. &amp; Bruhlmann, F. &amp; Ilyina, T. M. &amp; Mukhtarova, L. S. &amp; Grechkin, A. N." box="[515,756,371,390]" pageId="7" pageNumber="8" pagination="369 - 378" refId="ref16136" refString="Toporkova, Y. Y., Gorina, S. S., Bessolitsyna, E. K., Smirnova, E. O., Fatykhova, V. S., Bruhlmann, F., Ilyina, T. M., Mukhtarova, L. S., Grechkin, A. N., 2018 b. Double function hydroperoxide lyases / epoxyalcohol synthases (CYP 74 C) of higher plants: identification and conversion into allene oxide synthases by site-directed mutagenesis. Biochim. Biophys. Acta 1863, 369 - 378. https: // doi. org / 10.1016 / j. bbalip. 2018.01.002." type="journal article" year="2018">Toporkova et al., 2018b</bibRefCitation>
). LuDES (
<collectionCode id="9E90AE1C7A4BD25DFF7133B15FDBDEED" box="[179,224,399,418]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="7" pageNumber="8" type="Herbarium">CYP</collectionCode>
74
<collectionCode id="9E90AE1C7A4BD25DFF3A33B15E3DDEED" box="[248,262,399,418]" country="Germany" lsid="urn:lsid:biocol.org:col:15534" name="Botanischer Garten und Botanisches Museum Berlin-Dahlem, Zentraleinrichtung der Freien Universitaet" pageId="7" pageNumber="8" type="Herbarium">B</collectionCode>
16) was identified as dual function
<collectionCode id="9E90AE1C7A4BD25DFDAE33B15DAFDEED" box="[620,660,399,418]" country="USA" httpUri="http://biocol.org/urn:lsid:biocol.org:col:15533" lsid="urn:lsid:biocol.org:col:15533" name="Desert Botanical Garden" pageId="7" pageNumber="8" type="Herbarium">DES</collectionCode>
/HPL (with minor
<collectionCode id="9E90AE1C7A4BD25DFF6633955FF1DEF1" box="[164,202,427,446]" pageId="7" pageNumber="8">EAS</collectionCode>
activity) depending on substrate (
<bibRefCitation id="9C104B287A4BD25DFDD333955DCFDEF1" author="Toporkova, Y. Y. &amp; Smirnova, E. O. &amp; Mukhtarova, L. S. &amp; Gorina, S. S. &amp; Grechkin, A. N." box="[529,756,427,446]" pageId="7" pageNumber="8" pagination="112152" refId="ref16253" refString="Toporkova, Y. Y., Smirnova, E. O., Mukhtarova, L. S., Gorina, S. S., Grechkin, A. N., 2020 a. Catalysis by allene oxide synthases (CYP 74 A and CYP 74 C): alterations by the Phe / Leu mutation at the SRS- 1 region. Phytochemistry 169, 112152. https: // doi. org / 10.1016 / j. phytochem. 2019.112152." type="journal article" year="2020">Toporkova et al., 2020a</bibRefCitation>
). Additional
<collectionCode id="9E90AE1C7A4BD25DFF1033F95FC3DE95" box="[210,248,455,474]" pageId="7" pageNumber="8">EAS</collectionCode>
activity was exhibited by
<collectionCode id="9E90AE1C7A4BD25DFDC733F95D14DE95" box="[517,559,455,474]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="7" pageNumber="8" type="Herbarium">CYP</collectionCode>
74
<collectionCode id="9E90AE1C7A4BD25DFD8133F95D6BDE95" box="[579,592,455,474]" country="Germany" lsid="urn:lsid:biocol.org:col:15534" name="Botanischer Garten und Botanisches Museum Berlin-Dahlem, Zentraleinrichtung der Freien Universitaet" pageId="7" pageNumber="8" type="Herbarium">B</collectionCode>
HPLs (
<bibRefCitation id="9C104B287A4BD25DFD5F33F95FDCDEBA" author="Toporkova, Y. Y. &amp; Askarova, E. K. &amp; Gorina, S. S. &amp; Ogorodnikova, A. V. &amp; Mukhtarova, L. S. &amp; Grechkin, A. N." pageId="7" pageNumber="8" pagination="158743" refId="ref16339" refString="Toporkova, Y. Y., Askarova, E. K., Gorina, S. S., Ogorodnikova, A. V., Mukhtarova, L. S., Grechkin, A. N., 2020 b. Epoxyalcohol synthase activity of the CYP 74 B enzymes of higher plants. Biochim. Biophys. Acta 1865, 158743. https: // doi. org / 10.1016 / j. bbalip. 2020.158743." type="journal article" year="2020">Toporkova et al., 2020b</bibRefCitation>
), as well as by carrot allene oxide synthase DcAOS (
<collectionCode id="9E90AE1C7A4BD25DFCFA32AA5C5EDFE8" box="[824,869,148,167]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="7" pageNumber="8" type="Herbarium">CYP</collectionCode>
74
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33) (
<bibRefCitation id="9C104B287A4BD25DFC7732AA5B4CDFE8" author="Gorina, S. S. &amp; Mukhitova, F. K. &amp; Ilyina, T. M. &amp; Toporkova, Y. Y. &amp; Grechkin, A. N." box="[949,1143,148,167]" pageId="7" pageNumber="8" pagination="1580 - 1590" refId="ref12963" refString="Gorina, S. S., Mukhitova, F. K., Ilyina, T. M., Toporkova, Y. Y., Grechkin, A. N., 2019 b. Detection of unprecedented allene oxide synthase member of CYP 74 B subfamily: CYP 74 B 33 of carrot (Daucus carota). Biochim. Biophys. Acta 1864, 1580 - 1590. https: // doi. org / 10.1016 / j. bbalip. 2019.07.004." type="journal article" year="2019">Gorina et al., 2019b</bibRefCitation>
). A common intermediate of all reactions controlled by
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74s is the epoxyallylic radical (
<figureCitation id="60BA2A5C7A4BD25DFA47328E5AFADF8C" box="[1413,1473,176,195]" captionStart="Fig" captionStartId="6.[498,528,1964,1981]" captionTargetBox="[209,1379,1217,1935]" captionTargetId="figure-345@6.[207,1381,1215,1937]" captionTargetPageId="6" captionText="Fig. 7. The scheme of catalytic mechanisms of the CYP74L enzymes." figureDoi="http://doi.org/10.5281/zenodo.8235364" httpUri="https://zenodo.org/record/8235364/files/figure.png" pageId="7" pageNumber="8">Fig. 7</figureCitation>
). Depending on the substrate of the SmHPL1, the epoxyallylic radical undergoes either (i) a single electron oxidation followed by proton loss to
<taxonomicName id="3F814D5A7A4BD25DFC8E333D5CA4DE59" box="[844,927,259,278]" form="the" pageId="7" pageNumber="8" rank="form">form the</taxonomicName>
allene oxide (
<collectionCode id="9E90AE1C7A4BD25DFBEA333D5B68DE59" box="[1064,1107,259,278]" pageId="7" pageNumber="8">AOS</collectionCode>
pathway), or (ii) recombination with a hydroxyl radical to the epoxyalcohol (
<collectionCode id="9E90AE1C7A4BD25DFB6133215BF0DE7D" box="[1187,1227,287,306]" pageId="7" pageNumber="8">EAS</collectionCode>
pathway), or (iii) isomerization to the vinyloxycarbinyl radical which recombines with a hydroxyl radical, leading to the hemiacetal (HPL pathway), see
<figureCitation id="60BA2A5C7A4BD25DFAF133695A53DE25" box="[1331,1384,343,362]" captionStart="Fig" captionStartId="6.[498,528,1964,1981]" captionTargetBox="[209,1379,1217,1935]" captionTargetId="figure-345@6.[207,1381,1215,1937]" captionTargetPageId="6" captionText="Fig. 7. The scheme of catalytic mechanisms of the CYP74L enzymes." figureDoi="http://doi.org/10.5281/zenodo.8235364" httpUri="https://zenodo.org/record/8235364/files/figure.png" pageId="7" pageNumber="8">Fig. 7</figureCitation>
.
</paragraph>
<paragraph id="F83E36D97A4BD252FC93334D5E4BDF8C" blockId="7.[818,1488,148,502]" lastBlockId="8.[100,771,148,1506]" lastPageId="8" lastPageNumber="9" pageId="7" pageNumber="8">
Like other
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74 subfamilies, the
<collectionCode id="9E90AE1C7A4BD25DFB6F334D5BEDDEC9" box="[1197,1238,371,390]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="7" pageNumber="8" type="Herbarium">CYP</collectionCode>
74
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subfamily consists of different enzymes, namely AOSs and HPLs. The
<collectionCode id="9E90AE1C7A4BD25DFB3C33B15A1CDEED" box="[1278,1319,399,418]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="7" pageNumber="8" type="Herbarium">CYP</collectionCode>
74A subfamily includes 13-specific AOSs and 9/13-specific EASs. The
<collectionCode id="9E90AE1C7A4BD25DFAE333955A70DEF1" box="[1313,1355,427,446]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="7" pageNumber="8" type="Herbarium">CYP</collectionCode>
74
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subfamily comprises 13-specific HPLs and DESs, as well as at least one 9-specific
<collectionCode id="9E90AE1C7A4BD25DFCF033DD5C65DEB9" box="[818,862,483,502]" pageId="7" pageNumber="8">AOS</collectionCode>
. The
<collectionCode id="9E90AE1C7A4BD25DFC5733DD5C84DEB9" box="[917,959,483,502]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="7" pageNumber="8" type="Herbarium">CYP</collectionCode>
74
<collectionCode id="9E90AE1C7A4BD25DFC1633DD5CDADEB9" box="[980,993,483,502]" country="Denmark" name="University of Copenhagen" pageId="7" pageNumber="8" type="Herbarium">C</collectionCode>
subfamily includes 9/13-specific AOSs and double function HPL/EASs, and the
<collectionCode id="9E90AE1C7A44D252FEB032AA5EA7DFE8" box="[370,412,148,167]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="8" pageNumber="9" type="Herbarium">CYP</collectionCode>
74
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subfamily is composed of 13-specific DESs and EASs (
<figureCitation id="60BA2A5C7A44D252FEEF328E5E58DF8C" box="[301,355,176,195]" captionStart="Fig" captionStartId="7.[100,130,1531,1548]" captionTargetBox="[209,1379,544,1500]" captionTargetId="figure-286@7.[206,1381,542,1503]" captionTargetPageId="7" captionText="Fig. 8. The unrooted phylogenetic tree of the CYP74 clan. Classified CYP74 subfamilies are marked with their letter designation (A, B, C etc.). Subfamilies consisting of more than one member are outlined with unclosed curves (semi-ellipses). Plant CYP74s: As, Allium sativum; AsDES, CYP74H1, GI:83414021; At, Arabidopsis thaliana; AtAOS, CYP74A1, GI:15239032; AtHPL, CYP74B2, GI:3822403; Ca, Capsicum annuum; CaHPL, CYP74B1, GI:1272340; Cm, Cucumis melo; CmHPL/EAS, CYP74C2, GI:14134199; Cs, C. sativus; CsHPL/EAS, CYP74C1, GI:101211324; CsHPL/EAS/AOS, CYP74C31 GI:101211574; Dc, Daucus carota; DcAOS, CYP74B33, GI:10821971; Gm, Glycine max; GmHPL/EAS (CYP74C13_Gm), KRH29541.1; Hv, Hordeum vulgare; HvAOS2, CYP74A3, GI:7452981; HvHPL, CYP74F3, GI: 22265998; Kf, K. flaccidum (green alga); KfAOS, SI:LC032459; Le, Solanum lycopersicum; LeAOS1, CYP74A1, GI:7581989; LeAOS2, CYP74A2, GI:7677376; LeAOS3, CYP74C3, GI:25991603; LeHPL, CYP74B3, GI:7677378; LeDES (CYP74D1), NP001234527.1; Lu, Linum usitatissimum; LuAOS, CYP74A1, GI:1352186; LuDES, CYP74B16, GI:379048766; Mp, M. polymorpha; MpAOS1, SI:LC032457.1, MpAOS2, SI:LC032458.1; Mt, Medicago truncatula; MtHPL3, CYP74B5, GI:63081244; MtHPL1/EAS, CYP74C13, GI:33504430; Nt, Nicotiana tabacum; NtDES, CYP74D3; GI: 107799697; Os, Oryza sativa; OsAOS, CYP74A4, GI:115455571; OsHPL1, CYP74E2, GI:115445057; OsHPL2, CYP74E1, GI:125538638; Pa, Parthenium argentatum; PaAOS, CYP74A1, GI:218511958; Pd, Prunus dulcis; PdHPL, CYP74C5, GI:33300600; Pg, Psidium guajava; PgHPL, CYP74B5, GI:13183137; Pi, Petunia inflata; PiCYP74C9, GI:85720841; Pp, P. patens; PpAOS1, CYP74A1, GI:22217985; PpAOS2, CYP74A8, GI:168014176; PpHPL, CYP74G1, GI:76057841; Ra, Ranunculus acris; RaDES, CYP74Q1, GI:768564485; Rj, Ranunculus japonicus; RjEAS, CYP74A88, SI:MK061531; Sm, S. moellendorffii; SmDES1, CYP74M1, GI:9660714; SmEAS, CYP74M2, GI:9637471 SmDES2, CYP74M3, GI:9654395; SmAOS2, CYP74K3, EFJ20163.1; CYP74L1, XP002969700.1; CYP74L2, XP002972651.1; CYP74L3, EFJ25870.1; St, Solanum tuberosum; StAOS2, CYP74A6, GI:86769479; StAOS3, CYP74C10, GI:56605358; StHPL/EAS, CYP74C4, GI:102588560; StDES, CYP74D2, GI:12667099; Zm, Zea mays; ZmAOS, CYP74A19, GI:223947589; ZmHPL, CYP74F2, GI:162462890. CYP74 clan members: Es, E. siliculosus (brown alga); EsEAS, CYP5164B1, GI:1109557544; Mn, M. nodulans (proteobacteria); MnHPL, SI:WP_015932840.1; Msp, Methylobacterium sp. 446; MspCYP74, SI:WP_012335549.1. Ap, A. palmata (Metazoa); ApAOS, GI:187948710; Bf, B. floridae (Metazoa); BfEAS, CYP440A1, GI:189312561; Nv, N. vectensis (Metazoa); NvEAS, CYP443D1, GI:5516222; NvHPL/EAS CYP443C1 (GenBank QJI54761.1)." figureDoi="http://doi.org/10.5281/zenodo.8235366" httpUri="https://zenodo.org/record/8235366/files/figure.png" pageId="8" pageNumber="9">Fig. 8</figureCitation>
).
</paragraph>
<caption id="ACFE66517A4BD25DFFA637C55AAAD8F2" ID-DOI="http://doi.org/10.5281/zenodo.8235366" ID-Zenodo-Dep="8235366" httpUri="https://zenodo.org/record/8235366/files/figure.png" pageId="7" pageNumber="8" startId="7.[100,130,1531,1548]" targetBox="[209,1379,544,1500]" targetPageId="7" targetType="figure">
<paragraph id="F83E36D97A4BD25DFFA637C55AAAD8F2" blockId="7.[100,1489,1531,1981]" pageId="7" pageNumber="8">
<emphasis id="CAF5EACB7A4BD25DFFA637C55FA7D943" bold="true" box="[100,156,1531,1548]" pageId="7" pageNumber="8">Fig. 8.</emphasis>
The unrooted phylogenetic tree of the CYP74 clan. Classified CYP74 subfamilies are marked with their letter designation (A, B, C etc.). Subfamilies consisting of more than one member are outlined with unclosed curves (semi-ellipses). Plant CYP74s: As,
<taxonomicName id="3F814D5A7A4BD25DFC69342A5B1ED96A" box="[939,1061,1556,1573]" class="Liliopsida" family="Amaryllidaceae" genus="Allium" kingdom="Plantae" order="Asparagales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="sativum">
<emphasis id="CAF5EACB7A4BD25DFC69342A5B1ED96A" bold="true" box="[939,1061,1556,1573]" italics="true" pageId="7" pageNumber="8">Allium sativum</emphasis>
</taxonomicName>
; AsDES, CYP74H1, GI:83414021; At,
<taxonomicName id="3F814D5A7A4BD25DFAB0342A5F9DD971" class="Magnoliopsida" family="Brassicaceae" genus="Arabidopsis" kingdom="Plantae" order="Brassicales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="thaliana">
<emphasis id="CAF5EACB7A4BD25DFAB0342A5F9DD971" bold="true" italics="true" pageId="7" pageNumber="8">Arabidopsis thaliana</emphasis>
</taxonomicName>
; AtAOS, CYP74A1, GI:15239032; AtHPL, CYP74B2, GI:3822403; Ca,
<taxonomicName id="3F814D5A7A4BD25DFCC134105CA2D971" box="[771,921,1582,1599]" class="Magnoliopsida" family="Solanaceae" genus="Capsicum" kingdom="Plantae" order="Solanales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="annuum">
<emphasis id="CAF5EACB7A4BD25DFCC134105CA2D971" bold="true" box="[771,921,1582,1599]" italics="true" pageId="7" pageNumber="8">Capsicum annuum</emphasis>
</taxonomicName>
; CaHPL, CYP74B1, GI:1272340; Cm,
<taxonomicName id="3F814D5A7A4BD25DFB2334105A69D971" box="[1249,1362,1581,1599]" class="Magnoliopsida" family="Cucurbitaceae" genus="Cucumis" kingdom="Plantae" order="Cucurbitales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="melo">
<emphasis id="CAF5EACB7A4BD25DFB2334105A69D971" bold="true" box="[1249,1362,1581,1599]" italics="true" pageId="7" pageNumber="8">Cucumis melo</emphasis>
</taxonomicName>
; CmHPL/EAS, CYP74C2, GI:14134199; Cs,
<taxonomicName id="3F814D5A7A4BD25DFE9B34795E96D917" box="[345,429,1607,1624]" class="Magnoliopsida" family="Cucurbitaceae" genus="Cucumis" kingdom="Plantae" order="Cucurbitales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="sativus">C. sativus</taxonomicName>
; CsHPL/EAS, CYP74C1, GI:101211324; CsHPL/EAS/AOS, CYP74C31 GI:101211574; Dc,
<taxonomicName id="3F814D5A7A4BD25DFB6834765A25D917" box="[1194,1310,1608,1624]" class="Magnoliopsida" family="Apiaceae" genus="Daucus" kingdom="Plantae" order="Apiales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="carota">
<emphasis id="CAF5EACB7A4BD25DFB6834765A25D917" bold="true" box="[1194,1310,1608,1624]" italics="true" pageId="7" pageNumber="8">Daucus carota</emphasis>
</taxonomicName>
; DcAOS, CYP74B33, GI:10821971; Gm,
<emphasis id="CAF5EACB7A4BD25DFED3345E5E41D93E" bold="true" box="[273,378,1632,1649]" italics="true" pageId="7" pageNumber="8">Glycine max</emphasis>
; GmHPL/EAS (CYP74C13_Gm), KRH29541.1; Hv,
<taxonomicName id="3F814D5A7A4BD25DFC80345E5CEAD93E" box="[834,977,1632,1649]" class="Liliopsida" family="Poaceae" genus="Hordeum" kingdom="Plantae" order="Poales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="vulgare">
<emphasis id="CAF5EACB7A4BD25DFC80345E5CEAD93E" bold="true" box="[834,977,1632,1649]" italics="true" pageId="7" pageNumber="8">Hordeum vulgare</emphasis>
</taxonomicName>
; HvAOS2, CYP74A3, GI:7452981; HvHPL, CYP74F3, GI: 22265998; Kf,
<taxonomicName id="3F814D5A7A4BD25DFF2134455E72D9C4" box="[227,329,1658,1675]" class="Klebsormidiophyceae" family="Klebsormidiaceae" genus="Klebsormidium" kingdom="Plantae" order="Klebsormidiales" pageId="7" pageNumber="8" phylum="Charophyta" rank="species" species="flaccidum">
<emphasis id="CAF5EACB7A4BD25DFF2134455E72D9C4" bold="true" box="[227,329,1658,1675]" italics="true" pageId="7" pageNumber="8">K. flaccidum</emphasis>
</taxonomicName>
(green alga); KfAOS, SI:LC032459; Le,
<taxonomicName id="3F814D5A7A4BD25DFD5A34445C71D9C4" box="[664,842,1658,1675]" class="Magnoliopsida" family="Solanaceae" genus="Solanum" kingdom="Plantae" order="Solanales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="lycopersicum">
<emphasis id="CAF5EACB7A4BD25DFD5A34445C71D9C4" bold="true" box="[664,842,1658,1675]" italics="true" pageId="7" pageNumber="8">Solanum lycopersicum</emphasis>
</taxonomicName>
; LeAOS1, CYP74A1, GI:7581989; LeAOS2, CYP74A2, GI:7677376; LeAOS3, CYP74C3, GI:25991603; LeHPL, CYP74B3, GI:7677378; LeDES (CYP74D1), NP001234527.1; Lu,
<taxonomicName id="3F814D5A7A4BD25DFC0334AA5B52D9EA" box="[961,1129,1684,1701]" class="Magnoliopsida" family="Linaceae" genus="Linum" kingdom="Plantae" order="Malpighiales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="usitatissimum">
<emphasis id="CAF5EACB7A4BD25DFC0334AA5B52D9EA" bold="true" box="[961,1129,1684,1701]" italics="true" pageId="7" pageNumber="8">Linum usitatissimum</emphasis>
</taxonomicName>
; LuAOS, CYP74A1, GI:1352186; LuDES, CYP74B16, GI:379048766; Mp,
<taxonomicName id="3F814D5A7A4BD25DFEBF34935EC0D9F1" box="[381,507,1709,1726]" class="Marchantiopsida" family="Marchantiaceae" genus="Marchantia" kingdom="Plantae" order="Marchantiales" pageId="7" pageNumber="8" phylum="Marchantiophyta" rank="species" species="polymorpha">
<emphasis id="CAF5EACB7A4BD25DFEBF34935EC0D9F1" bold="true" box="[381,507,1709,1726]" italics="true" pageId="7" pageNumber="8">M. polymorpha</emphasis>
</taxonomicName>
; MpAOS1, SI:LC032457.1, MpAOS2, SI:LC032458.1; Mt,
<taxonomicName id="3F814D5A7A4BD25DFC3734935BA7D9F1" box="[1013,1180,1709,1726]" class="Magnoliopsida" family="Fabaceae" genus="Medicago" kingdom="Plantae" order="Fabales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="truncatula">
<emphasis id="CAF5EACB7A4BD25DFC3734935BA7D9F1" bold="true" box="[1013,1180,1709,1726]" italics="true" pageId="7" pageNumber="8">Medicago truncatula</emphasis>
</taxonomicName>
; MtHPL3, CYP74B5, GI:63081244; MtHPL1/EAS, CYP74C13, GI:33504430; Nt,
<taxonomicName id="3F814D5A7A4BD25DFE2A34F95DB9D998" box="[488,642,1734,1752]" class="Magnoliopsida" family="Solanaceae" genus="Nicotiana" kingdom="Plantae" order="Solanales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="tabacum">
<emphasis id="CAF5EACB7A4BD25DFE2A34F95DB9D998" bold="true" box="[488,642,1734,1752]" italics="true" pageId="7" pageNumber="8">Nicotiana tabacum</emphasis>
</taxonomicName>
; NtDES, CYP74D3; GI: 107799697; Os,
<taxonomicName id="3F814D5A7A4BD25DFC2634F95B77D997" box="[996,1100,1735,1752]" class="Liliopsida" family="Poaceae" genus="Oryza" kingdom="Plantae" order="Poales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="sativa">
<emphasis id="CAF5EACB7A4BD25DFC2634F95B77D997" bold="true" box="[996,1100,1735,1752]" italics="true" pageId="7" pageNumber="8">Oryza sativa</emphasis>
</taxonomicName>
; OsAOS, CYP74A4, GI:115455571; OsHPL1, CYP74E2, GI:115445057; OsHPL2, CYP74E1, GI:125538638; Pa,
<taxonomicName id="3F814D5A7A4BD25DFD5C34DE5C67D9BE" box="[670,860,1760,1777]" class="Magnoliopsida" family="Asteraceae" genus="Parthenium" kingdom="Plantae" order="Asterales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="argentatum">
<emphasis id="CAF5EACB7A4BD25DFD5C34DE5C67D9BE" bold="true" box="[670,860,1760,1777]" italics="true" pageId="7" pageNumber="8">Parthenium argentatum</emphasis>
</taxonomicName>
; PaAOS, CYP74A1, GI:218511958; Pd,
<taxonomicName id="3F814D5A7A4BD25DFB7B34DF5A1CD9BE" box="[1209,1319,1760,1777]" class="Magnoliopsida" family="Rosaceae" genus="Prunus" kingdom="Plantae" order="Rosales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="dulcis">
<emphasis id="CAF5EACB7A4BD25DFB7B34DF5A1CD9BE" bold="true" box="[1209,1319,1760,1777]" italics="true" pageId="7" pageNumber="8">Prunus dulcis</emphasis>
</taxonomicName>
; PdHPL, CYP74C5, GI:33300600; Pg,
<taxonomicName id="3F814D5A7A4BD25DFEC334C45EBED844" box="[257,389,1786,1803]" class="Magnoliopsida" family="Myrtaceae" genus="Psidium" kingdom="Plantae" order="Myrtales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="guajava">
<emphasis id="CAF5EACB7A4BD25DFEC334C45EBED844" bold="true" box="[257,389,1786,1803]" italics="true" pageId="7" pageNumber="8">Psidium guajava</emphasis>
</taxonomicName>
; PgHPL, CYP74B5, GI:13183137; Pi,
<taxonomicName id="3F814D5A7A4BD25DFD0834C45C7AD844" box="[714,833,1786,1803]" class="Magnoliopsida" family="Solanaceae" genus="Petunia" kingdom="Plantae" order="Solanales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="inflata">
<emphasis id="CAF5EACB7A4BD25DFD0834C45C7AD844" bold="true" box="[714,833,1786,1803]" italics="true" pageId="7" pageNumber="8">Petunia inflata</emphasis>
</taxonomicName>
; PiCYP74C9, GI:85720841; Pp,
<taxonomicName id="3F814D5A7A4BD25DFB9534C45B9AD845" box="[1111,1185,1786,1802]" class="Bryopsida" family="Funariaceae" genus="Physcomitrella" kingdom="Plantae" order="Funariales" pageId="7" pageNumber="8" phylum="Bryophyta" rank="species" species="patens">
<emphasis id="CAF5EACB7A4BD25DFB9534C45B9AD845" bold="true" box="[1111,1185,1786,1802]" italics="true" pageId="7" pageNumber="8">P. patens</emphasis>
</taxonomicName>
; PpAOS1, CYP74A1, GI:22217985; PpAOS2, CYP74A8, GI:168014176; PpHPL, CYP74G1, GI:76057841; Ra,
<taxonomicName id="3F814D5A7A4BD25DFD28352D5C4DD86B" box="[746,886,1811,1828]" class="Magnoliopsida" family="Ranunculaceae" genus="Ranunculus" kingdom="Plantae" order="Ranunculales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="acris">
<emphasis id="CAF5EACB7A4BD25DFD28352D5C4DD86B" bold="true" box="[746,886,1811,1828]" italics="true" pageId="7" pageNumber="8">Ranunculus acris</emphasis>
</taxonomicName>
; RaDES, CYP74Q1, GI:768564485; Rj,
<taxonomicName id="3F814D5A7A4BD25DFB17352D5ABCD86B" box="[1237,1415,1811,1828]" class="Magnoliopsida" family="Ranunculaceae" genus="Ranunculus" kingdom="Plantae" order="Ranunculales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="japonicus">
<emphasis id="CAF5EACB7A4BD25DFB17352D5ABCD86B" bold="true" box="[1237,1415,1811,1828]" italics="true" pageId="7" pageNumber="8">Ranunculus japonicus</emphasis>
</taxonomicName>
; RjEAS, CYP74A88, SI:MK061531; Sm,
<taxonomicName id="3F814D5A7A4BD25DFEBA35135D3BD871" box="[376,512,1837,1854]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="moellendorffii">
<emphasis id="CAF5EACB7A4BD25DFEBA35135D3BD871" bold="true" box="[376,512,1837,1854]" italics="true" pageId="7" pageNumber="8">S. moellendorffii</emphasis>
</taxonomicName>
; SmDES1, CYP74M1, GI:9660714; SmEAS, CYP74M2, GI:9637471 SmDES2, CYP74M3, GI:9654395; SmAOS2, CYP74K3, EFJ20163.1; CYP74L1, XP002969700.1; CYP74L2, XP002972651.1; CYP74L3, EFJ25870.1; St,
<taxonomicName id="3F814D5A7A4BD25DFBC335785B9AD818" box="[1025,1185,1862,1879]" class="Magnoliopsida" family="Solanaceae" genus="Solanum" kingdom="Plantae" order="Solanales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="tuberosum">
<emphasis id="CAF5EACB7A4BD25DFBC335785B9AD818" bold="true" box="[1025,1185,1862,1879]" italics="true" pageId="7" pageNumber="8">Solanum tuberosum</emphasis>
</taxonomicName>
; StAOS2, CYP74A6, GI:86769479; StAOS3, CYP74C10, GI:56605358; StHPL/EAS, CYP74C4, GI:102588560; StDES, CYP74D2, GI:12667099; Zm,
<taxonomicName id="3F814D5A7A4BD25DFBFA355E5BB3D83F" box="[1080,1160,1888,1904]" class="Liliopsida" family="Poaceae" genus="Zea" kingdom="Plantae" order="Poales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="mays">
<emphasis id="CAF5EACB7A4BD25DFBFA355E5BB3D83F" bold="true" box="[1080,1160,1888,1904]" italics="true" pageId="7" pageNumber="8">Zea mays</emphasis>
</taxonomicName>
; ZmAOS, CYP74A19, GI:223947589; ZmHPL, CYP74F2, GI:162462890. CYP74 clan members: Es,
<taxonomicName id="3F814D5A7A4BD25DFDBA35445DDBD8C5" box="[632,736,1913,1930]" class="Phaeophyceae" family="Ectocarpaceae" genus="Ectocarpus" kingdom="Chromista" order="Ectocarpales" pageId="7" pageNumber="8" phylum="Ochrophyta" rank="species" species="siliculosus">
<emphasis id="CAF5EACB7A4BD25DFDBA35445DDBD8C5" bold="true" box="[632,736,1913,1930]" italics="true" pageId="7" pageNumber="8">E. siliculosus</emphasis>
</taxonomicName>
(brown alga); EsEAS, CYP5164B1, GI:1109557544; Mn,
<taxonomicName id="3F814D5A7A4BD25DFB1135445A03D8C5" box="[1235,1336,1913,1930]" class="Alphaproteobacteria" family="Methylobacteriaceae" genus="Methylobacterium" kingdom="Bacteria" order="Rhizobiales" pageId="7" pageNumber="8" phylum="Proteobacteria" rank="species" species="nodulans">
<emphasis id="CAF5EACB7A4BD25DFB1135445A03D8C5" bold="true" box="[1235,1336,1913,1930]" italics="true" pageId="7" pageNumber="8">M. nodulans</emphasis>
</taxonomicName>
(proteobacteria); MnHPL, SI:WP_015932840.1; Msp,
<taxonomicName id="3F814D5A7A4BD25DFE5635AD5D5BD8EB" box="[404,608,1939,1956]" class="Alphaproteobacteria" family="Methylobacteriaceae" genus="Methylobacterium" kingdom="Bacteria" order="Rhizobiales" pageId="7" pageNumber="8" phylum="Proteobacteria" rank="species" species="undefined-4">Methylobacterium sp. 4</taxonomicName>
46; MspCYP74, SI:WP_012335549.1. Ap,
<taxonomicName id="3F814D5A7A4BD25DFC0E35AD5BBFD8EB" authority="(Metazoa)" baseAuthorityName="Metazoa" box="[972,1156,1939,1956]" class="Anthozoa" family="Acroporidae" genus="Acropora" kingdom="Animalia" order="Scleractinia" pageId="7" pageNumber="8" phylum="Cnidaria" rank="species" species="palmata">
<emphasis id="CAF5EACB7A4BD25DFC0E35AD5B1DD8EB" bold="true" box="[972,1062,1939,1956]" italics="true" pageId="7" pageNumber="8">A. palmata</emphasis>
(Metazoa)
</taxonomicName>
; ApAOS, GI:187948710; Bf,
<taxonomicName id="3F814D5A7A4BD25DFAB835AD5F87D8F2" authority="(Metazoa)" baseAuthorityName="Metazoa" class="Chilopoda" family="Scolopendridae" genus="Branchiostoma" kingdom="Animalia" order="Scolopendromorpha" pageId="7" pageNumber="8" phylum="Arthropoda" rank="species" species="floridae">
<emphasis id="CAF5EACB7A4BD25DFAB835AD5AF4D8EB" bold="true" box="[1402,1487,1939,1956]" italics="true" pageId="7" pageNumber="8">B. floridae</emphasis>
(Metazoa)
</taxonomicName>
; BfEAS, CYP440A1, GI:189312561; Nv,
<taxonomicName id="3F814D5A7A4BD25DFDD735925DE9D8F2" authority="(Metazoa)" baseAuthorityName="Metazoa" box="[533,722,1964,1981]" class="Anthozoa" family="Edwardsiidae" genus="Nematostella" kingdom="Animalia" order="Actiniaria" pageId="7" pageNumber="8" phylum="Cnidaria" rank="species" species="vectensis">
<emphasis id="CAF5EACB7A4BD25DFDD735925D4FD8F2" bold="true" box="[533,628,1964,1981]" italics="true" pageId="7" pageNumber="8">N. vectensis</emphasis>
(Metazoa)
</taxonomicName>
; NvEAS, CYP443D1, GI:5516222; NvHPL/EAS CYP443C1 (GenBank QJI54761.1).
</paragraph>
</caption>
<paragraph id="F83E36D97A44D252FF4632F55D84DCA3" blockId="8.[100,771,148,1506]" pageId="8" pageNumber="9">
Expanding knowledge on proteins (including P450s) in
<taxonomicName id="3F814D5A7A44D252FFA632D95FC2DFB5" box="[100,249,231,250]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="8" pageNumber="9" phylum="Tracheophyta" rank="species" species="moellendorffii">
<emphasis id="CAF5EACB7A44D252FFA632D95FC2DFB5" bold="true" box="[100,249,231,250]" italics="true" pageId="8" pageNumber="9">S. moellendorffii</emphasis>
</taxonomicName>
, one of the oldest vascular plants, is essential for understanding molecular evolution (
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,b, 2011;
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;
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;
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;
<bibRefCitation id="9C104B287A44D252FD4033215FAFDE01" author="Yokota, T. &amp; Ohnishi, T. &amp; Shibata, K. &amp; Asahina, M. &amp; Nomura, T. &amp; Fujita, T. &amp; Ishizaki, K. &amp; Kohchi, T." pageId="8" pageNumber="9" pagination="46 - 55" refId="ref16891" refString="Yokota, T., Ohnishi, T., Shibata, K., Asahina, M., Nomura, T., Fujita, T., Ishizaki, K., Kohchi, T., 2017. Occurrence of brassinosteroids in non-flowering land plants, liverwort, moss, lycophyte and fern. Phytochemistry 136, 46 - 55. https: // doi. org / 10.1016 / j. phytochem. 2016.12.020." type="journal article" year="2017">Yokota et al., 2017</bibRefCitation>
;
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;
<bibRefCitation id="9C104B287A44D252FE9B33055D35DE01" author="Ferrari, C. &amp; Shivhare, D. &amp; Hansen, B. O. &amp; Pasha, A. &amp; Esteban, E. &amp; Provart, N. J. &amp; Kragler, F. &amp; Fernie, A. &amp; Tohge, T. &amp; Mutwil, M." box="[345,526,315,334]" pageId="8" pageNumber="9" pagination="853 - 870" refId="ref12780" refString="Ferrari, C., Shivhare, D., Hansen, B. O., Pasha, A., Esteban, E., Provart, N. J., Kragler, F., Fernie, A., Tohge, T., Mutwil, M., 2020. Expression atlas of Selaginella moellendorffii provides insights into the evolution of vasculature, secondary metabolism, and roots. Plant Cell 32 (4), 853 - 870. https: // doi. org / 10.1105 / tpc. 19.00780." type="journal article" year="2020">Ferrari et al., 2020</bibRefCitation>
). Spikemosses are phylogenetically situated between bryophytes (mosses, liverworts, and hornworts) and euphyllophytes, which include flowering plants. The lipoxygenase pathway of
<taxonomicName id="3F814D5A7A44D252FE9E33B15ECADEEE" box="[348,497,398,418]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="8" pageNumber="9" phylum="Tracheophyta" rank="species" species="moellendorffii">
<emphasis id="CAF5EACB7A44D252FE9E33B15ECADEEE" bold="true" box="[348,497,398,418]" italics="true" pageId="8" pageNumber="9">S. moellendorffii</emphasis>
</taxonomicName>
,
<taxonomicName id="3F814D5A7A44D252FDC233B15FE6DEF1" authority="(Ogorodnikova et al., 2015)" baseAuthorityName="Ogorodnikova" baseAuthorityYear="2015" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="8" pageNumber="9" phylum="Tracheophyta" rank="species" species="martensii">
<emphasis id="CAF5EACB7A44D252FDC233B15D57DEED" bold="true" box="[512,620,399,418]" italics="true" pageId="8" pageNumber="9">S. martensii</emphasis>
(
<bibRefCitation id="9C104B287A44D252FDBE33B15FEEDEF2" author="Ogorodnikova, A. V. &amp; Mukhitova, F. K. &amp; Grechkin, A. N." pageId="8" pageNumber="9" pagination="42 - 50" refId="ref14742" refString="Ogorodnikova, A. V., Mukhitova, F. K., Grechkin, A. N., 2015. Oxylipins in the spikemoss Selaginella martensii: detection of divinyl ethers, 12 - oxophytodienoic acid and related cyclopentenones. Phytochemistry 118, 42 - 50. https: // doi. org / 10.1016 / j. phytochem. 2015.08.003." type="journal article" year="2015">Ogorodnikova et al., 2015</bibRefCitation>
)
</taxonomicName>
,
<taxonomicName id="3F814D5A7A44D252FF2933955E05DEF1" box="[235,318,427,446]" class="Bryopsida" family="Funariaceae" genus="Physcomitrella" kingdom="Plantae" order="Funariales" pageId="8" pageNumber="9" phylum="Bryophyta" rank="species" species="patens">
<emphasis id="CAF5EACB7A44D252FF2933955E05DEF1" bold="true" box="[235,318,427,446]" italics="true" pageId="8" pageNumber="9">P. patens</emphasis>
</taxonomicName>
and
<taxonomicName id="3F814D5A7A44D252FEB133955C39DEF1" authority="(Mukhtarova et al., 2020)" baseAuthorityName="Mukhtarova" baseAuthorityYear="2020" box="[371,770,426,446]" class="Marchantiopsida" family="Marchantiaceae" genus="Marchantia" kingdom="Plantae" order="Marchantiales" pageId="8" pageNumber="9" phylum="Marchantiophyta" rank="species" species="polymorpha">
<emphasis id="CAF5EACB7A44D252FEB133955EC6DEF2" bold="true" box="[371,509,426,446]" italics="true" pageId="8" pageNumber="9">M. polymorpha</emphasis>
(
<bibRefCitation id="9C104B287A44D252FDCC33955DC1DEF1" author="Mukhtarova, L. S. &amp; Lantsova, N. V. &amp; Khairutdinov, B. I. &amp; Grechkin, A. N." box="[526,762,427,446]" pageId="8" pageNumber="9" pagination="13" refId="ref14434" refString="Mukhtarova, L. S., Lantsova, N. V., Khairutdinov, B. I., Grechkin, A. N., 2020. Lipoxygenase pathway in model bryophytes: 12 - oxo- 9 (13), 15 - phytodienoic acid is a predominant oxylipin in Physcomitrella patens. Phytochemistry 180. https: // doi. org / 10.1016 / j. phytochem. 2020.112533, 112533." type="journal article" year="2020">Mukhtarova et al., 2020</bibRefCitation>
)
</taxonomicName>
possess some peculiarities compared to flowering plants. For instance,
<taxonomicName id="3F814D5A7A44D252FFA633DC5FCEDEBA" box="[100,245,482,501]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="8" pageNumber="9" phylum="Tracheophyta" rank="species" species="moellendorffii">
<emphasis id="CAF5EACB7A44D252FFA633DC5FCEDEBA" bold="true" box="[100,245,482,501]" italics="true" pageId="8" pageNumber="9">S. moellendorffii</emphasis>
</taxonomicName>
(present work),
<taxonomicName id="3F814D5A7A44D252FE4C33DC5DC6DEB9" authority="(Ogorodnikova et al., 2015)" baseAuthorityName="Ogorodnikova" baseAuthorityYear="2015" box="[398,765,482,502]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="8" pageNumber="9" phylum="Tracheophyta" rank="species" species="martensii">
<emphasis id="CAF5EACB7A44D252FE4C33DC5ECEDEBA" bold="true" box="[398,501,482,501]" italics="true" pageId="8" pageNumber="9">S. martensii</emphasis>
(
<bibRefCitation id="9C104B287A44D252FDC033DC5DCFDEBA" author="Ogorodnikova, A. V. &amp; Mukhitova, F. K. &amp; Grechkin, A. N." box="[514,756,482,502]" pageId="8" pageNumber="9" pagination="42 - 50" refId="ref14742" refString="Ogorodnikova, A. V., Mukhitova, F. K., Grechkin, A. N., 2015. Oxylipins in the spikemoss Selaginella martensii: detection of divinyl ethers, 12 - oxophytodienoic acid and related cyclopentenones. Phytochemistry 118, 42 - 50. https: // doi. org / 10.1016 / j. phytochem. 2015.08.003." type="journal article" year="2015">Ogorodnikova et al., 2015</bibRefCitation>
)
</taxonomicName>
,
<taxonomicName id="3F814D5A7A44D252FFA633C15F8EDD5D" box="[100,181,511,530]" class="Bryopsida" family="Funariaceae" genus="Physcomitrella" kingdom="Plantae" order="Funariales" pageId="8" pageNumber="9" phylum="Bryophyta" rank="species" species="patens">
<emphasis id="CAF5EACB7A44D252FFA633C15F8EDD5D" bold="true" box="[100,181,511,530]" italics="true" pageId="8" pageNumber="9">P. patens</emphasis>
</taxonomicName>
and
<taxonomicName id="3F814D5A7A44D252FF2733C15D5CDD5E" authority="(Mukhtarova et al., 2020)" baseAuthorityName="Mukhtarova" baseAuthorityYear="2020" box="[229,615,510,530]" class="Marchantiopsida" family="Marchantiaceae" genus="Marchantia" kingdom="Plantae" order="Marchantiales" pageId="8" pageNumber="9" phylum="Marchantiophyta" rank="species" species="polymorpha">
<emphasis id="CAF5EACB7A44D252FF2733C15E57DD5E" bold="true" box="[229,364,510,530]" italics="true" pageId="8" pageNumber="9">M. polymorpha</emphasis>
(
<bibRefCitation id="9C104B287A44D252FEB933C05D5BDD5E" author="Mukhtarova, L. S. &amp; Lantsova, N. V. &amp; Khairutdinov, B. I. &amp; Grechkin, A. N." box="[379,608,510,530]" pageId="8" pageNumber="9" pagination="13" refId="ref14434" refString="Mukhtarova, L. S., Lantsova, N. V., Khairutdinov, B. I., Grechkin, A. N., 2020. Lipoxygenase pathway in model bryophytes: 12 - oxo- 9 (13), 15 - phytodienoic acid is a predominant oxylipin in Physcomitrella patens. Phytochemistry 180. https: // doi. org / 10.1016 / j. phytochem. 2020.112533, 112533." type="journal article" year="2020">Mukhtarova et al., 2020</bibRefCitation>
)
</taxonomicName>
possess a prominent
<emphasis id="CAF5EACB7A44D252FF5E30245F8FDD62" bold="true" box="[156,180,538,557]" italics="true" pageId="8" pageNumber="9">iso</emphasis>
-12-OPDA, which is relatively uncommon in flowering plants. On the other hand, jasmonates, widespread in flowering plants, have been detected neither in
<taxonomicName id="3F814D5A7A44D252FE92306C5ED8DD2A" box="[336,483,594,613]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="8" pageNumber="9" phylum="Tracheophyta" rank="species" species="moellendorffii">
<emphasis id="CAF5EACB7A44D252FE92306C5ED8DD2A" bold="true" box="[336,483,594,613]" italics="true" pageId="8" pageNumber="9">S. moellendorffii</emphasis>
</taxonomicName>
(present work) nor in mosses, including
<taxonomicName id="3F814D5A7A44D252FF0130505E2FDDCE" box="[195,276,622,641]" class="Bryopsida" family="Funariaceae" genus="Physcomitrella" kingdom="Plantae" order="Funariales" pageId="8" pageNumber="9" phylum="Bryophyta" rank="species" species="patens">
<emphasis id="CAF5EACB7A44D252FF0130505E2FDDCE" bold="true" box="[195,276,622,641]" italics="true" pageId="8" pageNumber="9">P. patens</emphasis>
</taxonomicName>
and
<taxonomicName id="3F814D5A7A44D252FE8630505EF7DDCE" box="[324,460,622,641]" class="Marchantiopsida" family="Marchantiaceae" genus="Marchantia" kingdom="Plantae" order="Marchantiales" pageId="8" pageNumber="9" phylum="Marchantiophyta" rank="species" species="polymorpha">
<emphasis id="CAF5EACB7A44D252FE8630505EF7DDCE" bold="true" box="[324,460,622,641]" italics="true" pageId="8" pageNumber="9">M. polymorpha</emphasis>
</taxonomicName>
(
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; Ponce de Leon et al., 2015;
<bibRefCitation id="9C104B287A44D252FEDA30B45D38DDD2" author="Mukhtarova, L. S. &amp; Lantsova, N. V. &amp; Khairutdinov, B. I. &amp; Grechkin, A. N." box="[280,515,650,669]" pageId="8" pageNumber="9" pagination="13" refId="ref14434" refString="Mukhtarova, L. S., Lantsova, N. V., Khairutdinov, B. I., Grechkin, A. N., 2020. Lipoxygenase pathway in model bryophytes: 12 - oxo- 9 (13), 15 - phytodienoic acid is a predominant oxylipin in Physcomitrella patens. Phytochemistry 180. https: // doi. org / 10.1016 / j. phytochem. 2020.112533, 112533." type="journal article" year="2020">Mukhtarova et al., 2020</bibRefCitation>
). Pratiwi et al. (2017) reported the detection of jasmonate in
<taxonomicName id="3F814D5A7A44D252FE7830985D70DDF7" box="[442,587,677,697]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="8" pageNumber="9" phylum="Tracheophyta" rank="species" species="moellendorffii">
<emphasis id="CAF5EACB7A44D252FE7830985D70DDF7" bold="true" box="[442,587,677,697]" italics="true" pageId="8" pageNumber="9">S. moellendorffii</emphasis>
</taxonomicName>
. However, the only evidence presented was the SIM LC-MS analysis, while no spectrometry data was provided. We observed no signs of jasmonate presence in
<taxonomicName id="3F814D5A7A44D252FFA630C75FCDDC43" box="[100,246,761,780]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="8" pageNumber="9" phylum="Tracheophyta" rank="species" species="moellendorffii">
<emphasis id="CAF5EACB7A44D252FFA630C75FCDDC43" bold="true" box="[100,246,761,780]" italics="true" pageId="8" pageNumber="9">S. moellendorffii</emphasis>
</taxonomicName>
(present work), nor in
<taxonomicName id="3F814D5A7A44D252FE0C30C75FA5DC67" authority="(Ogorodnikova et al., 2015)" baseAuthorityName="Ogorodnikova" baseAuthorityYear="2015" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="8" pageNumber="9" phylum="Tracheophyta" rank="species" species="martensii">
<emphasis id="CAF5EACB7A44D252FE0C30C75D0DDC43" bold="true" box="[462,566,761,780]" italics="true" pageId="8" pageNumber="9">S. martensii</emphasis>
(
<bibRefCitation id="9C104B287A44D252FD8130C75FAFDC67" author="Ogorodnikova, A. V. &amp; Mukhitova, F. K. &amp; Grechkin, A. N." pageId="8" pageNumber="9" pagination="42 - 50" refId="ref14742" refString="Ogorodnikova, A. V., Mukhitova, F. K., Grechkin, A. N., 2015. Oxylipins in the spikemoss Selaginella martensii: detection of divinyl ethers, 12 - oxophytodienoic acid and related cyclopentenones. Phytochemistry 118, 42 - 50. https: // doi. org / 10.1016 / j. phytochem. 2015.08.003." type="journal article" year="2015">Ogorodnikova et al., 2015</bibRefCitation>
)
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. The lack of jasmonates was attributed before to the absence of 12-oxo-PDA reductase OPR
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non-flowering plants (
<bibRefCitation id="9C104B287A44D252FDB2310C5FAFDC2F" 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; Althoff, F. &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; 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; Schmut, J." pageId="8" pageNumber="9" pagination="287 - 304" refId="ref11641" 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, F., 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., R ¨ ovekamp, 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., Schmut, J., 2017. Insights into land plant evolution garnered from the Marchantia polymorpha genome. Cell 171, 287 - 304. https: // doi. org / 10.1016 / j. cell. 2017.09.030." type="journal article" year="2017">Bowman et al., 2017</bibRefCitation>
; Ponce de Leon et al., 2015). The OPDA system is more ancient a stress signalling pathway than the jasmonate one. However, the OPDA system already includes almost all the components of the jasmonate system (
<bibRefCitation id="9C104B287A44D252FF77319F5E45DCFB" author="Schluttenhofer, C." box="[181,382,929,948]" pageId="8" pageNumber="9" refId="ref15347" refString="Schluttenhofer, C., 2020. Origin and evolution of jasmonate signaling. Plant Sci. 298 https: // doi. org / 10.1016 / j. plantsci. 2020.110542, 110542." type="journal volume" year="2020">Schluttenhofer, 2020</bibRefCitation>
). In flowering plants, the emergence of jasmonates as more specific ligands than OPDA for signal receptors improved the efficiency of functioning of this signalling system.
</paragraph>
<paragraph id="F83E36D97A44D252FF4631CA5EFADBDC" blockId="8.[100,771,148,1506]" pageId="8" pageNumber="9">
The OPDA system is an older a stress signalling pathway than the jasmonate system. However, the OPDA system included almost all components of the jasmonate system (
<bibRefCitation id="9C104B287A44D252FE1A36125D9BDB70" author="Schluttenhofer, C." box="[472,672,1068,1087]" pageId="8" pageNumber="9" refId="ref15347" refString="Schluttenhofer, C., 2020. Origin and evolution of jasmonate signaling. Plant Sci. 298 https: // doi. org / 10.1016 / j. plantsci. 2020.110542, 110542." type="journal volume" year="2020">Schluttenhofer, 2020</bibRefCitation>
). In flowering plants, the emergence of jasmonates as more specific ligands for signaling receptors than OPDA seems to have increased the efficiency of functioning of this signalling system.
</paragraph>
<paragraph id="F83E36D97A44D252FF4636A25DABDAAD" blockId="8.[100,771,148,1506]" pageId="8" pageNumber="9">
Diversity of
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74 genes in
<taxonomicName id="3F814D5A7A44D252FE7E36A25D6CDBE1" box="[444,599,1179,1199]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="8" pageNumber="9" phylum="Tracheophyta" rank="species" species="moellendorffii">
<emphasis id="CAF5EACB7A44D252FE7E36A25D6CDBE1" bold="true" box="[444,599,1179,1199]" italics="true" pageId="8" pageNumber="9">S. moellendorffii</emphasis>
</taxonomicName>
, including DESs (
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74
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1 and
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74
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3),
<collectionCode id="9E90AE1C7A44D252FEBA36865EA5DB84" box="[376,414,1208,1227]" pageId="8" pageNumber="9">EAS</collectionCode>
(
<collectionCode id="9E90AE1C7A44D252FE6D36865EE7DB84" box="[431,476,1208,1227]" country="Cyprus" httpUri="http://biocol.org/urn:lsid:biocol.org:col:13586" lsid="urn:lsid:biocol.org:col:13586" name="Ministry of Agriculture, Natural Resources and Environment" pageId="8" pageNumber="9" type="Herbarium">CYP</collectionCode>
74
<collectionCode id="9E90AE1C7A44D252FE3636865D32DB84" box="[500,521,1208,1227]" country="Germany" lsid="urn:lsid:biocol.org:col:15637" name="Botanische Staatssammlung München" pageId="8" pageNumber="9" type="Herbarium">M</collectionCode>
2), HPL (
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74
<collectionCode id="9E90AE1C7A44D252FD6436865D8EDB84" box="[678,693,1208,1227]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="8" pageNumber="9" type="Herbarium">L</collectionCode>
1), AOSs (including the characterized AOSs
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74K3 and
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74
<collectionCode id="9E90AE1C7A44D252FDAB36EA5D4DDBA8" box="[617,630,1236,1255]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="8" pageNumber="9" type="Herbarium">L</collectionCode>
2, as well as the putative AOSs
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74J1,
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74K1, and
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74K2), establishes the complexity of the oxylipin profile in spikemoss tissues. Recent findings on the enzymes of lipoxygenase pathway in the green alga
<taxonomicName id="3F814D5A7A44D252FD4E37165DC7DA75" box="[652,764,1319,1339]" class="Klebsormidiophyceae" family="Klebsormidiaceae" genus="Klebsormidium" kingdom="Plantae" order="Klebsormidiales" pageId="8" pageNumber="9" phylum="Charophyta" rank="species" species="flaccidum">
<emphasis id="CAF5EACB7A44D252FD4E37165DC7DA75" bold="true" box="[652,764,1319,1339]" italics="true" pageId="8" pageNumber="9">K. flaccidum</emphasis>
</taxonomicName>
, the liverwort
<taxonomicName id="3F814D5A7A44D252FF24377D5D70DA19" authority="(Koeduka et al., 2015)" baseAuthorityName="Koeduka" baseAuthorityYear="2015" box="[230,587,1347,1367]" class="Marchantiopsida" family="Marchantiaceae" genus="Marchantia" kingdom="Plantae" order="Marchantiales" pageId="8" pageNumber="9" phylum="Marchantiophyta" rank="species" species="polymorpha">
<emphasis id="CAF5EACB7A44D252FF24377D5E55DA19" bold="true" box="[230,366,1347,1366]" italics="true" pageId="8" pageNumber="9">M. polymorpha</emphasis>
(
<bibRefCitation id="9C104B287A44D252FEBF377D5D79DA19" author="Koeduka, T. &amp; Ishizaki, K. &amp; Mwenda, C. M. &amp; Hori, K. &amp; Sasaki-Sekimoto, Y. &amp; Ohta, H. &amp; Kohchi, T. &amp; Matsui, K." box="[381,578,1347,1367]" pageId="8" pageNumber="9" pagination="1175 - 1186" refId="ref14143" refString="Koeduka, T., Ishizaki, K., Mwenda, C. M., Hori, K., Sasaki-Sekimoto, Y., Ohta, H., Kohchi, T., Matsui, K., 2015. Biochemical characterization of allene oxide synthases from the liverwort Marchantia polymorpha and green microalgae Klebsormidium flaccidum provides insight into the evolutionary divergence of the plant CYP 74 family. Planta 242, 1175 - 1186. https: // doi. org / 10.1007 / s 00425 - 015 - 2355 - 8." type="journal article" year="2015">Koeduka et al., 2015</bibRefCitation>
)
</taxonomicName>
, the moss
<taxonomicName id="3F814D5A7A44D252FD73377D5E5CDA3D" authority="(Mukhtarova et al., 2020)" baseAuthorityName="Mukhtarova" baseAuthorityYear="2020" class="Bryopsida" family="Funariaceae" genus="Physcomitrella" kingdom="Plantae" order="Funariales" pageId="8" pageNumber="9" phylum="Bryophyta" rank="species" species="patens">
<emphasis id="CAF5EACB7A44D252FD73377D5C3ADA19" bold="true" box="[689,769,1347,1366]" italics="true" pageId="8" pageNumber="9">P. patens</emphasis>
(
<bibRefCitation id="9C104B287A44D252FFAE37615E65DA3D" author="Mukhtarova, L. S. &amp; Lantsova, N. V. &amp; Khairutdinov, B. I. &amp; Grechkin, A. N." box="[108,350,1375,1395]" pageId="8" pageNumber="9" pagination="13" refId="ref14434" refString="Mukhtarova, L. S., Lantsova, N. V., Khairutdinov, B. I., Grechkin, A. N., 2020. Lipoxygenase pathway in model bryophytes: 12 - oxo- 9 (13), 15 - phytodienoic acid is a predominant oxylipin in Physcomitrella patens. Phytochemistry 180. https: // doi. org / 10.1016 / j. phytochem. 2020.112533, 112533." type="journal article" year="2020">Mukhtarova et al., 2020</bibRefCitation>
)
</taxonomicName>
, the spikemoss
<taxonomicName id="3F814D5A7A44D252FDC837615D52DA3D" box="[522,617,1375,1394]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="8" pageNumber="9" phylum="Tracheophyta" rank="genus">
<emphasis id="CAF5EACB7A44D252FDC837615D52DA3D" bold="true" box="[522,617,1375,1394]" italics="true" pageId="8" pageNumber="9">Selaginella</emphasis>
</taxonomicName>
(
<bibRefCitation id="9C104B287A44D252FDBE37615FEADAC1" author="Ogorodnikova, A. V. &amp; Mukhitova, F. K. &amp; Grechkin, A. N." pageId="8" pageNumber="9" pagination="42 - 50" refId="ref14742" refString="Ogorodnikova, A. V., Mukhitova, F. K., Grechkin, A. N., 2015. Oxylipins in the spikemoss Selaginella martensii: detection of divinyl ethers, 12 - oxophytodienoic acid and related cyclopentenones. Phytochemistry 118, 42 - 50. https: // doi. org / 10.1016 / j. phytochem. 2015.08.003." type="journal article" year="2015">Ogorodnikova et al., 2015</bibRefCitation>
;
<bibRefCitation id="9C104B287A44D252FF1F37455EABDAC1" author="Gorina, S. S. &amp; Toporkova, Y. Y. &amp; Mukhtarova, L. S. &amp; Smirnova, E. O. &amp; Chechetkin, I. R. &amp; Khairutdinov, B. I. &amp; Gogolev, Y. V. &amp; Grechkin, A. N." box="[221,400,1403,1422]" pageId="8" pageNumber="9" pagination="301 - 309" refId="ref13051" refString="Gorina, S. S., Toporkova, Y. Y., Mukhtarova, L. S., Smirnova, E. O., Chechetkin, I. R., Khairutdinov, B. I., Gogolev, Y. V., Grechkin, A. N., 2016. Oxylipin biosynthesis in spikemoss Selaginella moellendorffii: molecular cloning and identification of divinyl ether synthases CYP 74 M 1 and CYP 74 M 3. Biochim. Biophys. Acta 1861, 301 - 309. https: // doi. org / 10.1016 / j. bbalip. 2016.01.001." type="journal article" year="2016">Gorina et al., 2016</bibRefCitation>
; Pratiwi et al., 2017;
<bibRefCitation id="9C104B287A44D252FDA237455FA4DAE5" author="Toporkova, Y. Y. &amp; Smirnova, E. O. &amp; Gorina, S. S. &amp; Mukhtarova, L. S. &amp; Grechkin, A. N." pageId="8" pageNumber="9" pagination="73 - 82" refId="ref16051" refString="Toporkova, Y. Y., Smirnova, E. O., Gorina, S. S., Mukhtarova, L. S., Grechkin, A. N., 2018 a. Detection of the first higher plant epoxyalcohol synthase: molecular cloning and characterisation of the CYP 74 M 2 enzyme of spikemoss Selaginella moellendorffii. Phytochemistry 156, 73 - 82. https: // doi. org / 10.1016 / j. phytochem. 2018.08.010." type="journal article" year="2018">Toporkova et al., 2018a</bibRefCitation>
), as well as the results of present work, shed light onto the enzymatic apparatus of oxylipin biosynthesis of non-flowering plants and its changes in the course of early land plant evolution.
</paragraph>
</subSubSection>
</treatment>
</document>