191 lines
27 KiB
XML
191 lines
27 KiB
XML
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<mods:title id="6990C748106E690FD48D5A231E170B1E">Biosynthesis of cannflavins A and B from Cannabis sativa L</mods:title>
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<mods:namePart id="102A6BAE98BA2C5C8B92A4E809CB41FA">Rea, Kevin A</mods:namePart>
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<mods:affiliation id="0F3BD8B9550480DC6684B8462FD940C7">∗ & Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario, N 1 G 2 W 1, Canada</mods:affiliation>
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<mods:namePart id="781AD976947B06967AACD99AD0B53322">Casaretto, José A.</mods:namePart>
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<mods:namePart id="865D455C4F2DDF871AB649D2C23EE1C3">Geddes-McAlister, Jennifer</mods:namePart>
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<mods:namePart id="5E31106D808F8B4EDFBDBF2488CC8B0A">Rothstein, Steven J.</mods:namePart>
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<mods:namePart id="7D412BD2F9717D4A8F7F85BA3034A2A7">Akhtar, Tariq A.</mods:namePart>
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<mods:title id="0CFEF064F99FC2AD30604CF408F51BD9">Phytochemistry</mods:title>
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<treatment id="AC68879FFFB7BD1CFFE045FA3423782E" ID-GBIF-Taxon="220662854" LSID="urn:lsid:plazi:treatment:AC68879FFFB7BD1CFFE045FA3423782E" httpUri="http://treatment.plazi.org/id/AC68879FFFB7BD1CFFE045FA3423782E" lastPageNumber="166" pageId="4" pageNumber="166">
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<subSubSection id="6CDB6502FFB7BD1CFFE045FA37FF7EC5" pageId="4" pageNumber="166" type="nomenclature">
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<paragraph id="247E3689FFB7BD1CFFE045FA37FF7EC5" blockId="4.[100,770,159,178]" lastBlockId="4.[100,431,187,206]" pageId="4" pageNumber="166">
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<heading id="7F3681E5FFB7BD1CFFE045FA35527EB9" bold="true" box="[100,770,159,178]" centered="true" fontSize="36" level="1" pageId="4" pageNumber="166" reason="1">
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2.3. Phylogenetic analysis of
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<taxonomicName id="E3C14D0AFFB7BD1CFEE845FA37EA7EB9" ID-CoL="QM84" baseAuthorityName="McPartland and Russo" baseAuthorityYear="2001" box="[364,442,159,178]" class="Magnoliopsida" family="Cannabaceae" genus="Cannabis" kingdom="Plantae" order="Rosales" pageId="4" pageNumber="166" phylum="Tracheophyta" rank="species" species="sativa">C. sativa</taxonomicName>
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O-methyltransferases involved in the
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<heading id="7F3681E5FFB7BD1CFFE045DE37FF7EC5" box="[100,431,187,206]" fontSize="8" level="3" pageId="4" pageNumber="166" reason="8">methylation of luteolin to chryseoriol</heading>
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</emphasis>
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</paragraph>
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<subSubSection id="6CDB6502FFB7BD1CFF0145963423782E" pageId="4" pageNumber="166" type="description">
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<paragraph id="247E3689FFB7BD1CFF01459634777D5B" blockId="4.[100,770,243,1573]" pageId="4" pageNumber="166">
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The observation that CsPT3 preferentially prenylates chrysoeriol,
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<emphasis id="16B5EA9BFFB7BD1CFD75459636DC7F29" bold="true" italics="true" pageId="4" pageNumber="166">in vitro</emphasis>
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, and that prenylated luteolin is apparently absent in extracts from
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<taxonomicName id="E3C14D0AFFB7BD1CFFE0444E36E57F35" baseAuthorityName="McPartland and Russo" baseAuthorityYear="2001" box="[100,181,299,318]" class="Magnoliopsida" family="Cannabaceae" genus="Cannabis" kingdom="Plantae" order="Rosales" pageId="4" pageNumber="166" phylum="Tracheophyta" rank="species" species="sativa">
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<emphasis id="16B5EA9BFFB7BD1CFFE0444E36E57F35" bold="true" box="[100,181,299,318]" italics="true" pageId="4" pageNumber="166">C. sativa</emphasis>
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</taxonomicName>
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implies,
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<emphasis id="16B5EA9BFFB7BD1CFE95444E37067F35" bold="true" box="[273,342,299,318]" italics="true" pageId="4" pageNumber="166">a priori</emphasis>
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, that methylation of luteolin to chrysoeriol must occur first in the cannflavin A and/or B pathway. We reasoned that the alleged enzyme that methylates luteolin at the 3′-hydroxyl position of the flavone B-ring to yield chrysoeriol would likely fall into the class of
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<emphasis id="16B5EA9BFFB7BD1CFF6044FF36BF7FA6" bold="true" box="[228,239,410,429]" italics="true" pageId="4" pageNumber="166">S</emphasis>
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-
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<subScript id="B84534CCFFB7BD1CFF7144FF370D7FA6" attach="left" box="[245,349,410,429]" fontSize="6" pageId="4" pageNumber="166">adenosyl-L-</subScript>
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methionine (AdoMet)-dependent
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<emphasis id="16B5EA9BFFB7BD1CFD2044FF34E37FA6" bold="true" box="[676,691,410,429]" italics="true" pageId="4" pageNumber="166">O</emphasis>
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-methyltransferases (OMTs), which are widely distributed throughout the plant kingdom (
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<bibRefCitation id="40504B78FFB7BD1CFF4344B737DA7FEE" author="Ibrahim, R. K. & Bruneau, A. & Bantignies, B." box="[199,394,466,485]" pageId="4" pageNumber="166" pagination="1 - 10" refId="ref10139" refString="Ibrahim, R. K., Bruneau, A., Bantignies, B., 1998. Plant O-methyltransferases: molecular analysis, common signature and classification. Plant Mol. Biol. 36, 1 - 10." type="journal article" year="1998">Ibrahim et al., 1998</bibRefCitation>
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||
;
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||
<bibRefCitation id="40504B78FFB7BD1CFE1C44B734717FEE" author="Ibrahim, R. K." box="[408,545,466,485]" pageId="4" pageNumber="166" pagination="433 - 450" refId="ref10105" refString="Ibrahim, R. K., 2005. A forty-year journey in plant research: original contributions to flavonoid biochemistry. Can. J. Bot. 83, 433 - 450." type="journal article" year="2005">Ibrahim, 2005</bibRefCitation>
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||
;
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||
<bibRefCitation id="40504B78FFB7BD1CFDAB44B7349D7FEE" author="Kim, B. G. & Sung, S. H. & Chong, Y. & Lim, Y. & Ahn, J. H." box="[559,717,466,485]" pageId="4" pageNumber="166" pagination="321 - 329" refId="ref10331" refString="Kim, B. G., Sung, S. H., Chong, Y., Lim, Y., Ahn, J. H., 2010. Plant flavonoid o-methyltransferases: substrate specificity and application. J. Plant Biol. 53, 321 - 329." type="journal article" year="2010">Kim et al., 2010</bibRefCitation>
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). We focused our initial searches of the TSA database for
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<taxonomicName id="E3C14D0AFFB7BD1CFDD7448B34F17C0A" baseAuthorityName="McPartland and Russo" baseAuthorityYear="2001" box="[595,673,494,513]" class="Magnoliopsida" family="Cannabaceae" genus="Cannabis" kingdom="Plantae" order="Rosales" pageId="4" pageNumber="166" phylum="Tracheophyta" rank="species" species="sativa">
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<emphasis id="16B5EA9BFFB7BD1CFDD7448B34F17C0A" bold="true" box="[595,673,494,513]" italics="true" pageId="4" pageNumber="166">C. sativa</emphasis>
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</taxonomicName>
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on
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<typeStatus id="FB7A882BFFB7BD1CFD42448B34BF7C0A" box="[710,751,494,513]" pageId="4" pageNumber="166">type</typeStatus>
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1 OMTs, which specifically methylate hydroxyl moieties of phenylpropanoid-based compounds (
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<bibRefCitation id="40504B78FFB7BD1CFEE0474334547C32" author="Noel, J. P. & Dixon, R. A. & Pickersky, E. & Zubieta, C. & Ferrer, J. L." box="[356,516,550,569]" pageId="4" pageNumber="166" pagination="37 - 58" refId="ref11125" refString="Noel, J. P., Dixon, R. A., Pickersky, E., Zubieta, C., Ferrer, J. L., 2003. Structural, functional and evolutionary basis for methylation of plant small molecules. Recent Adv. Phytochem. 37, 37 - 58." type="journal article" year="2003">Noel et al., 2003</bibRefCitation>
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). Using a previously characterized flavonoid-
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<emphasis id="16B5EA9BFFB7BD1CFEA7472737627C5E" bold="true" box="[291,306,578,597]" italics="true" pageId="4" pageNumber="166">O</emphasis>
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-methyltransferase from
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<taxonomicName id="E3C14D0AFFB7BD1CFDA5472734C57C5E" box="[545,661,578,597]" class="Liliopsida" family="Poaceae" genus="Oryza" kingdom="Plantae" order="Poales" pageId="4" pageNumber="166" phylum="Tracheophyta" rank="species" species="sativa">
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<emphasis id="16B5EA9BFFB7BD1CFDA5472734C57C5E" bold="true" box="[545,661,578,597]" italics="true" pageId="4" pageNumber="166">Oryza sativa</emphasis>
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</taxonomicName>
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(OsOMT9) that methylates the 3′-hydroxyl group on a variety of flavonoids as a query (
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<bibRefCitation id="40504B78FFB7BD1CFF2E471F37177C86" author="Kim, B. G. & Lee, Y. & Hur, H. G. & Lim, Y. & Ahn, J. H." box="[170,327,634,653]" pageId="4" pageNumber="166" pagination="387 - 394" refId="ref10275" refString="Kim, B. G., Lee, Y., Hur, H. G., Lim, Y., Ahn, J. H., 2006. Flavonoid 3 ' - O-methyltransferase from rice: cDNA cloning, characterization and functional expression. Phytochemistry 67, 387 - 394." type="journal article" year="2006">Kim et al., 2006</bibRefCitation>
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), this search uncovered 40 unique nucleotide sequences corresponding to partial and/or full-length transcripts that were loosely annotated as ‘caffeic acid-
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<emphasis id="16B5EA9BFFB7BD1CFE5F47D437BA7CCF" bold="true" box="[475,490,689,708]" italics="true" pageId="4" pageNumber="166">O</emphasis>
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-methyltransferases’. We next compared these transcript sequences via BLASTn searches against the
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<taxonomicName id="E3C14D0AFFB7BD1CFFE0478C36EA7CF7" box="[100,186,745,764]" class="Magnoliopsida" family="Cannabaceae" genus="Cannabis" kingdom="Plantae" order="Rosales" pageId="4" pageNumber="166" phylum="Tracheophyta" rank="genus">Cannabis</taxonomicName>
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whole genome contig database to confirm their corresponding full-length open reading frames. This analysis revealed twenty-four unique protein sequences (
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<figureCitation id="BCFA2A0CFFB7BD1CFEE5464437F27D3F" box="[353,418,801,820]" captionStart="Figure 5" captionStartId="6.[1038,1096,152,169]" captionTargetBox="[100,1007,151,915]" captionTargetPageId="6" captionText="Figure 5. Enzymatic characterization of CsOMT21. (A) Three flavones (apigenin, luteolin and chrysoeriol) and two flavonols (quercetin and kaempferol) that typically accumulate in C. sativa were tested as potential substrates. (B) Relative enzyme activity and substrate preference. Recombinant CsOMT21 was purified by Ni2+-affinity chromatography (inset). Proteins were resolved by SDS-PAGE and stained with Coomassie Blue. Lanes 1 and 2 contain crude E. coli extracts containing CsOMT21 and the purified protein, respectively; Molecular weights (kDa) are indicated. The selected flavones and flavonols (as numbered above) were provided to recombinant CsOMT21 in enzyme assays along with [14C]-AdoMet as a methyl donor. Data are the means ± SD from three independent experiments and are presented as relative activity compared to that observed with the preferred substrate, luteolin. (C) Evidence for the conversion of luteolin to chrysoeriol by CsOMT21. Enzyme assays with CsOMT21 together with luteolin and unlabelled AdoMet as cosubstrates were extracted and analyzed by HPLC. Note the identical retention time and CID-Q-TOF mass spectral fragmentation pattern of the enzymatic product from these assays (bottom panel) with that of an authentic chrysoeriol standard (top panel). (D) Kinetic analysis of CsOMT21. Recombinant CsOMT21 was assayed under standard assay conditions at the indicated concentrations of luteolin. Kinetic parameters were determined by non-linear regression analysis using the Michaelis-Menten kinetics model of the SigmaPlot 12.3 software." figureDoi="http://doi.org/10.5281/zenodo.10483108" httpUri="https://zenodo.org/record/10483108/files/figure.png" pageId="4" pageNumber="166">Fig. S5</figureCitation>
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) which were subsequently annotated as
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<emphasis id="16B5EA9BFFB7BD1CFFFB465836B37D5B" bold="true" box="[127,227,829,848]" italics="true" pageId="4" pageNumber="166">
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<taxonomicName id="E3C14D0AFFB7BD1CFFFB4658369D7D5B" box="[127,205,829,848]" class="Liliopsida" family="Poaceae" genus="Oryza" kingdom="Plantae" order="Poales" pageId="4" pageNumber="166" phylum="Tracheophyta" rank="species" species="sativa">C. sativa</taxonomicName>
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O
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</emphasis>
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-methyltransferases (CsOMT1-24).
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</paragraph>
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<paragraph id="247E3689FFB7BD1CFF01463C3423782E" blockId="4.[100,770,243,1573]" pageId="4" pageNumber="166">
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A phylogenetic analysis of the CsOMT family was then performed to establish their evolutionary relatedness to various plant OMTs that have been previously identified to act on aromatic substrates. This analysis revealed that
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<typeStatus id="FB7A882BFFB7BD1CFF6E46C937437DB4" box="[234,275,940,959]" pageId="4" pageNumber="166">type</typeStatus>
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||
1 CsOMTs are distributed into four general groups (
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<figureCitation id="BCFA2A0CFFB7BD1CFFE846AD36F17DD0" box="[108,161,968,987]" captionStart="Fig" captionStartId="5.[1039,1069,152,169]" captionTargetBox="[100,1044,151,1203]" captionTargetId="graphics-488@5.[127,1001,152,1203]" captionTargetPageId="5" captionText="Fig. 4. Phylogenetic analysis of type 1 O-methyltransferases from C. sativa. A neighbour-joining phylogenetic tree (1000 replicates) of type 1 O-methyltransferases from diverse plants was constructed using the MEGA 6.0 software package. Included in this analysis are twenty-four unique type 1 O-methyltransferases (CsOMTs) that were identified in the C. sativa genome. Branch lengths indicate the number of amino acid substitutions per sequence and bootstrap values (> 60%) are indicated next to each branch. The amino acid sequences and species abbreviations for all of these type 1 o-methyltransferases are listed in Supplemental Fig. S1 along with their corresponding GenBank accession numbers. Note that the CsOMTs (bolded) are uniformly distributed amongst four main groups of plant type 1 proteins." figureDoi="http://doi.org/10.5281/zenodo.10483104" httpUri="https://zenodo.org/record/10483104/files/figure.png" pageId="4" pageNumber="166">Fig. 4</figureCitation>
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). It should be noted however, as
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<bibRefCitation id="40504B78FFB7BD1CFE5846AD34FB7DD0" author="Schroder, G. & Wehinger, E. & Schroder, J." box="[476,683,968,987]" pageId="4" pageNumber="166" pagination="1 - 8" refId="ref12090" refString="Schroder, G., Wehinger, E., Schroder, J., 2002. Predicting the substrates of cloned plant O-methyltransferases. Phytochemistry 59, 1 - 8." type="journal article" year="2002">Schrӧder et al. (2002)</bibRefCitation>
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and
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<bibRefCitation id="40504B78FFB7BD1CFD5E46AD36887DFC" author="Lam, K. C. & Ibrahim, R. K. & Behdad, B. & Dayanandan, S." pageId="4" pageNumber="166" pagination="1001 - 1013" refId="ref10445" refString="Lam, K. C., Ibrahim, R. K., Behdad, B., Dayanandan, S., 2007. Structure, function, and evolution of plant O-methyltransferases. Genome 50, 1001 - 1013." type="journal article" year="2007">Lam et al. (2007)</bibRefCitation>
|
||
previously pointed out, that assigning substrate preference based on sequence similarity alone for this class of plant enzymes is precarious. For example, the first group of
|
||
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|
||
1 plant OMTs depicted in our phylogenetic analysis includes enzymes that utilize a broad array of aromatic substrates - from simple phenolic compounds, such as chavicol, guaiacol and orcinol (
|
||
<bibRefCitation id="40504B78FFB7BD1CFE15411534667A88" author="Gang, D. R. & Lavid, N. & Zubieta, C. & Chen, F. & Beuerle, T. & Lewinsohn, E. & Noel, J. P. & Pichersky, E." box="[401,566,1136,1155]" pageId="4" pageNumber="166" pagination="505 - 519" refId="ref9979" refString="Gang, D. R., Lavid, N., Zubieta, C., Chen, F., Beuerle, T., Lewinsohn, E., Noel, J. P., Pichersky, E., 2002. Characterization of phenylpropene O-methyltransferases from sweet basil: facile change of substrate specificity and convergent evolution within a plant O-methyltransferase family. Plant Cell 14, 505 - 519." type="journal article" year="2002">Gang et al., 2002</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="40504B78FFB7BD1CFDC7411534AC7A88" author="Scalliet, G. & Lionnet, C. & Le Bechec, M. & Dutron, L. & Magnard, J. L. & Baudino, S. & Bergougnoux, V. & Jullien, F. & Chambrier, P. & Vergne, P. & Dumas, C. & Cock, J. M. & Hugueney, P." box="[579,764,1136,1155]" pageId="4" pageNumber="166" pagination="18 - 29" refId="ref11855" refString="Scalliet, G., Lionnet, C., Le Bechec, M., Dutron, L., Magnard, J. L., Baudino, S., Bergougnoux, V., Jullien, F., Chambrier, P., Vergne, P., Dumas, C., Cock, J. M., Hugueney, P., 2006. Role of petal-specific orcinol O-methyltransferases in the evolution of rose scent. Plant Physiol. 140, 18 - 29." type="journal article" year="2006">Scalliet et al., 2006</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="40504B78FFB7BD1CFFE041E9374A7A94" author="Akhtar, T. A. & Pichersky, E." box="[100,282,1164,1183]" pageId="4" pageNumber="166" pagination="52 - 62" refId="ref9318" refString="Akhtar, T. A., Pichersky, E., 2013. Veratrole biosynthesis in white campion. Plant Physiol. 162, 52 - 62." type="journal article" year="2013">Akhtar et al., 2013</bibRefCitation>
|
||
), to more complex heterocyclic aromatics, such as homoeriodictoyl, myricetin, and resveratrol (
|
||
<bibRefCitation id="40504B78FFB7BD1CFDA141CD34AC7AB0" author="Schroder, G. & Wehinger, E. & Lukacin, R. & Wellmann, F. & Seefelder, W. & Schwab, W. & Schroder, J." box="[549,764,1191,1211]" pageId="4" pageNumber="166" pagination="1085 - 1094" refId="ref12122" refString="Schroder, G., Wehinger, E., Lukacin, R., Wellmann, F., Seefelder, W., Schwab, W., Schroder, J., 2004. Flavonoid methylation: a novel 4 ' - O-methyltransferase from Catharanthus roseus, and evidence that partially methylated flavanones are substrates of four different flavonoid dioxygenases. Phytochemistry 65, 1085 - 1094." type="journal article" year="2004">Schrӧder et al., 2004</bibRefCitation>
|
||
; Schmidin et al., 2008;
|
||
<bibRefCitation id="40504B78FFB7BD1CFEC241A6345D7ADD" author="Schmidt, A. & Li, C. & Shi, F. & Jones, A. D. & Pichersky, E." box="[326,525,1219,1238]" pageId="4" pageNumber="166" pagination="1999 - 2009" refId="ref12022" refString="Schmidt, A., Li, C., Shi, F., Jones, A. D., Pichersky, E., 2011. Polymethylated myricetin in trichomes of the wild tomato species Solanum habrochaites and characterization of trichome-specific 3 ' / 5 ' - and 7 / 4 ' - myricetin O-methyltransferases. Plant Physiol. 155, 1999 - 2009." type="journal article" year="2011">Schmidt et al., 2011</bibRefCitation>
|
||
). We found nine CsOMT family members present within this group. The second group of
|
||
<typeStatus id="FB7A882BFFB7BD1CFD4241BA34BF7AF9" box="[710,751,1247,1266]" pageId="4" pageNumber="166">type</typeStatus>
|
||
1 OMTs appear specific to the
|
||
<taxonomicName id="E3C14D0AFFB7BD1CFE01419E34507B05" box="[389,512,1275,1294]" class="Magnoliopsida" family="Cannabaceae" kingdom="Plantae" order="Rosales" pageId="4" pageNumber="166" phylum="Tracheophyta" rank="family">Cannabaceae</taxonomicName>
|
||
family and include seven CsOMTs along with two OMTs from
|
||
<taxonomicName id="E3C14D0AFFB7BD1CFE47407234087B21" box="[451,600,1303,1322]" class="Magnoliopsida" family="Cannabaceae" genus="Humulus" kingdom="Plantae" order="Rosales" pageId="4" pageNumber="166" phylum="Tracheophyta" rank="species" species="lupulus">
|
||
<emphasis id="16B5EA9BFFB7BD1CFE47407234087B21" bold="true" box="[451,600,1303,1322]" italics="true" pageId="4" pageNumber="166">Humulus lupulus</emphasis>
|
||
</taxonomicName>
|
||
that are involved in the synthesis xanthohumol (
|
||
<bibRefCitation id="40504B78FFB7BD1CFE034056347D7B4D" author="Nagel, J. & Culley, L. K. & Lu, Y. & Liu, E. & Matthews, P. D. & Stevens, J. F. & Page, J. E." box="[391,557,1331,1350]" pageId="4" pageNumber="166" pagination="186 - 200" refId="ref11056" refString="Nagel, J., Culley, L. K., Lu, Y., Liu, E., Matthews, P. D., Stevens, J. F., Page, J. E., 2008. EST analysis of hop glandular trichomes identifies an O-methyltransferase that catalyzes the biosynthesis of xanthohumol. Plant Cell 20, 186 - 200." type="journal article" year="2008">Nagel et al., 2008</bibRefCitation>
|
||
). The third and fourth groups represent two closely related sister clades of
|
||
<typeStatus id="FB7A882BFFB7BD1CFDD6402A342B7B69" box="[594,635,1359,1378]" pageId="4" pageNumber="166">type</typeStatus>
|
||
1 plant OMTs and contain the remaining members of the CsOMT family. Strikingly, all plant OMTs that are known to methylate the 3′-hydroxyl position of various flavonoids are confined to group three and include representatives from
|
||
<taxonomicName id="E3C14D0AFFB7BD1CFE9E40DA37D17BD9" box="[282,385,1471,1490]" class="Magnoliopsida" family="Brassicaceae" genus="Arabidopsis" kingdom="Plantae" order="Brassicales" pageId="4" pageNumber="166" phylum="Tracheophyta" rank="genus">
|
||
<emphasis id="16B5EA9BFFB7BD1CFE9E40DA37D17BD9" bold="true" box="[282,385,1471,1490]" italics="true" pageId="4" pageNumber="166">Arabidopsis</emphasis>
|
||
</taxonomicName>
|
||
, peppermint, rice, wheat, and American golden saxifrage (
|
||
<bibRefCitation id="40504B78FFB7BD1CFE9040BF37B47BE6" author="Gauthier, A. & Gulick, P. & Ibrahim, R. K." box="[276,484,1498,1517]" pageId="4" pageNumber="166" pagination="1163 - 1169" refId="ref10055" refString="Gauthier, A., Gulick, P., Ibrahim, R. K., 1996. cDNA cloning and characterization of a 3 ' / 5 ' - O-methyltransferase for partiallymethylated flavonols from Chrysosplenium americanum. Plant Mol. Biol. 32, 1163 - 1169." type="journal article" year="1996">Gauthier et al., 1996</bibRefCitation>
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||
;
|
||
<bibRefCitation id="40504B78FFB7BD1CFE7040BF34FE7BE6" author="Muzac, I. & Wang, J. & Anzellotti, D. & Zhang, H. & Ibrahim, R. K." box="[500,686,1498,1517]" pageId="4" pageNumber="166" pagination="385 - 388" refId="ref10929" refString="Muzac, I., Wang, J., Anzellotti, D., Zhang, H., Ibrahim, R. K., 2000. Functional expression of an Arabidopsis cDNA clone encoding a flavonol 3 - O-methyltransferase and characterization of the gene product. Arch. Biochem. Biophys. 375, 385 - 388." type="journal article" year="2000">Muzac et al., 2000</bibRefCitation>
|
||
; Willitis et al., 2004;
|
||
<bibRefCitation id="40504B78FFB7BD1CFF6D409337DE7802" author="Kim, B. G. & Lee, Y. & Hur, H. G. & Lim, Y. & Ahn, J. H." box="[233,398,1526,1545]" pageId="4" pageNumber="166" pagination="387 - 394" refId="ref10275" refString="Kim, B. G., Lee, Y., Hur, H. G., Lim, Y., Ahn, J. H., 2006. Flavonoid 3 ' - O-methyltransferase from rice: cDNA cloning, characterization and functional expression. Phytochemistry 67, 387 - 394." type="journal article" year="2006">Kim et al., 2006</bibRefCitation>
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||
;
|
||
<bibRefCitation id="40504B78FFB7BD1CFE1B4093341E7802" author="Zhou, J. M. & Gold, N. D. & Martin, V. J. J. & Wollenweber, E. & Ibrahim, R. K." box="[415,590,1526,1545]" pageId="4" pageNumber="166" pagination="1115 - 1124" refId="ref13276" refString="Zhou, J. M., Gold, N. D., Martin, V. J. J., Wollenweber, E., Ibrahim, R. K., 2006. Sequential O-methylation of tricetin by a single gene product in wheat. Biochim. Biophys. Acta 1760, 1115 - 1124." type="journal article" year="2006">Zhou et al., 2006</bibRefCitation>
|
||
). We found three CsOMTs (CsOMT6, 12 and 21) that fell into this group.
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |