299 lines
39 KiB
XML
299 lines
39 KiB
XML
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<emphasis id="B97D0F5E5E2F9E25FC8CA9AC22BD90A2" bold="true" box="[818,1457,1460,1480]" italics="true" pageId="2" pageNumber="3">2.4. Establishing the metabolic network of isoquinoline alkaloids in the</emphasis>
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genus
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Metabolic networks can provide new insight into the biosynthesis pathways of some important compounds present in plant-derived medicines. Sanguinarine and chelerythrine, which are the main components of the
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genus, are used as animal food additives. We previously characterized the biosynthesis pathways of these two compounds in
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thoroughly (
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<bibRefCitation id="EF98AEBD5E2F9E25FBACAA8C23AF93CD" author="Liu, X. B. & Liu, Y. S. & Huang, P. & Ma, Y. S. & Qing, Z. X. & Tang, Q. & Cao, H. F. & Cheng, P. & Zheng, Y. J. & Yuan, Z. J. & Zhou, Y. & Liu, J. F. & Tang, Z. S. & Zhuo, Y. X. & Zhang, Y. C. & Yu, L. L. & Huang, J. L. & Yang, P. & Peng, Q. & Zhang, J. B. & Jiang, W. K. & Zhang, Z. H. & Lin, K. & Ro, D. K. & Chen, X. Y. & Xiong, X. Y. & Shang, Y. & Huang, S. W. & Zeng, J. G." box="[1042,1187,1684,1703]" pageId="2" pageNumber="3" pagination="975 - 989" refId="ref6370" refString="Liu, X. B., Liu, Y. S., Huang, P., Ma, Y. S., Qing, Z. X., Tang, Q., Cao, H. F., Cheng, P., Zheng, Y. J., Yuan, Z. J., Zhou, Y., Liu, J. F., Tang, Z. S., Zhuo, Y. X., Zhang, Y. C., Yu, L. L., Huang, J. L., Yang, P., Peng, Q., Zhang, J. B., Jiang, W. K., Zhang, Z. H., Lin, K., Ro, D. K., Chen, X. Y., Xiong, X. Y., Shang, Y., Huang, S. W., Zeng, J. G., 2017. The genome of medicinal plant Macleaya cordata provides new insights into benzylisoquinoline alkaloids metabolism. Mol. Plant 10 (7), 975 - 989. https: // doi. org / 10.1016 / j. molp. 2017.05.007." type="journal article" year="2017">Liu et al., 2017</bibRefCitation>
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). However, are there any other biosynthesis pathways involving either of these two alkaloids in the
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genus plants? Establishment of the metabolic networks is an effective method to answer this question. In this study, a metabolic framework was established primarily based on the reported biosynthesis pathways.
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specific metabolic network of isoquinoline alkaloids was then constructed based on the structural relations and differences for identified compounds’ metabolic levels at various growth stages and isotopically labeled [
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]-tyrosine feeding experiment.
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In the
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plants, most isoquinoline alkaloids are synthesized from the benzyltetrahydroisoquinoline alkaloids, which can then be converted to tetrahydroprotoberberine and aporphine alkaloids.
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- methyltetrahydroprotoberberine, protoberberine, and 7,8-dihydroprotoberberine are derived from tetrahydroprotoberberine-type alkaloids. Protopine is generated from an
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-methyltetrahydroprotoberberine-type alkaloid, and it is continually metabolized to dihydrobenzophenanthridine and benzophenanthridine alkaloids (
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;
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<bibRefCitation id="EF98AEBD5E2E9E24FD1DAD0727DC9424" author="Takemura, T. & Ikezawa, N. & Iwasa, K. & Sato, F." pageId="3" pageNumber="4" pagination="100 - 108" refId="ref7529" refString="Takemura, T., Ikezawa, N., Iwasa, K., Sato, F., 2013. Molecular cloning and characterization of a cytochrome P 450 in sanguinarine biosynthesis from Eschscholzia californica cells. Phytochemistry 91, 100 - 108. https: // doi. org / 10.1016 / j. phytochem. 2012.02.013." type="journal article" year="2013">Takemura et al., 2013</bibRefCitation>
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) (Fig.
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6(
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)).
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metabolic framework of isoquinoline alkaloids in the
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genus was established based on the above metabolism of alkaloids. Take alkaloids
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(3
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-hydroxy-
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,
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-dimethylcoclaurine) and
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(10-demethylmagnoflorine) as an example. Compounds
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||
and
|
||
<emphasis id="B97D0F5E5E2E9E24FE30ADB226BF94D7" bold="true" box="[398,435,426,445]" pageId="3" pageNumber="4">115</emphasis>
|
||
were identified as benzyltetrahydroisoquinoline- and aporphine-type alkaloids, respectively (
|
||
<figureCitation id="1332CFC95E2E9E24FD0FADDF25F894B0" box="[689,756,455,474]" captionStart="Fig" captionStartId="5.[498,528,1049,1066]" captionTargetBox="[213,1395,159,1013]" captionTargetId="figure-594@5.[187,1400,148,1021]" captionTargetPageId="5" captionText="Fig. 3. TICs of 0-day (A) and 36-day-old (B) tissue culture seedlings." figureDoi="http://doi.org/10.5281/zenodo.8259860" httpUri="https://zenodo.org/record/8259860/files/figure.png" pageId="3" pageNumber="4">Fig. S3</figureCitation>
|
||
). Both alkaloids have the same substituent groups, and the benzyltetrahydroisoquinoline can be converted to aporphine in the
|
||
<taxonomicName id="4C09A8CF5E2E9E24FD11ADE727949744" class="Magnoliopsida" family="Papaveraceae" kingdom="Plantae" order="Ranunculales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="family">Papaveraceae</taxonomicName>
|
||
family (
|
||
<bibRefCitation id="EF98AEBD5E2E9E24FF56AE02268C9747" author="Sato, F. & Inui, T. & Takemura, T." box="[232,384,538,558]" pageId="3" pageNumber="4" pagination="211 - 218" refId="ref7399" refString="Sato, F., Inui, T., Takemura, T., 2007. Metabolic engineering in isoquinoline alkaloid biosynthesis. Curr. Pharmaceut. Biotechnol. 8 (4), 211 - 218. https: // doi. org / 10.2174 / 138920107781387438." type="journal article" year="2007">Sato et al., 2007</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="EF98AEBD5E2E9E24FE35AE0225309747" author="Ziegler, J. & Schmidt, J. & Kramell, R. & Miersch, O. & Ammer, C. & Gesell, A. & Kutchan, T. M." box="[395,572,538,558]" pageId="3" pageNumber="4" pagination="177 - 192" refId="ref7976" refString="Ziegler, J., Voigtl ¨ ander, S., Schmidt, J., Kramell, R., Miersch, O., Ammer, C., Gesell, A., Kutchan, T. M., 2006. Comparative transcript and alkaloid profiling in Papaver species identifies a short chaindehydrogenase / reductase involved in morphine biosynthesis. Plant J. 48 (2), 177 - 192. https: // doi. org / 10.1111 / j. 1365 - 313 X. 2006.02860. x." type="journal article" year="2006">Ziegler et al., 2006</bibRefCitation>
|
||
). Therefore, alkaloid
|
||
<emphasis id="B97D0F5E5E2E9E24FFDAAE2E27719723" bold="true" box="[100,125,566,585]" pageId="3" pageNumber="4">17</emphasis>
|
||
was regarded as the precursor of
|
||
<emphasis id="B97D0F5E5E2E9E24FE76AE2E26E19723" bold="true" box="[456,493,566,585]" pageId="3" pageNumber="4">115</emphasis>
|
||
. The relations of substituent groups (Fig.
|
||
<collectionCode id="ED184B895E2E9E24FF64AE4A27EA970F" box="[218,230,594,613]" country="Sweden" lsid="urn:lsid:biocol.org:col:15668" name="Department of Botany, Swedish Museum of Natural History" pageId="3" pageNumber="4" type="Herbarium">S</collectionCode>
|
||
6(B)) that have been reported in the
|
||
<taxonomicName id="4C09A8CF5E2E9E24FD82AE49259E970F" box="[572,658,593,613]" class="Magnoliopsida" family="Papaveraceae" genus="Macleaya" kingdom="Plantae" order="Ranunculales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="genus">
|
||
<emphasis id="B97D0F5E5E2E9E24FD82AE49259E970F" bold="true" box="[572,658,593,613]" italics="true" pageId="3" pageNumber="4">Macleaya</emphasis>
|
||
</taxonomicName>
|
||
genus were employed for establishing the specific metabolic network of the same skeleton compounds (
|
||
<bibRefCitation id="EF98AEBD5E2E9E24FE83AE9226D197F7" author="Liu, X. B. & Liu, Y. S. & Huang, P. & Ma, Y. S. & Qing, Z. X. & Tang, Q. & Cao, H. F. & Cheng, P. & Zheng, Y. J. & Yuan, Z. J. & Zhou, Y. & Liu, J. F. & Tang, Z. S. & Zhuo, Y. X. & Zhang, Y. C. & Yu, L. L. & Huang, J. L. & Yang, P. & Peng, Q. & Zhang, J. B. & Jiang, W. K. & Zhang, Z. H. & Lin, K. & Ro, D. K. & Chen, X. Y. & Xiong, X. Y. & Shang, Y. & Huang, S. W. & Zeng, J. G." box="[317,477,650,669]" pageId="3" pageNumber="4" pagination="975 - 989" refId="ref6370" refString="Liu, X. B., Liu, Y. S., Huang, P., Ma, Y. S., Qing, Z. X., Tang, Q., Cao, H. F., Cheng, P., Zheng, Y. J., Yuan, Z. J., Zhou, Y., Liu, J. F., Tang, Z. S., Zhuo, Y. X., Zhang, Y. C., Yu, L. L., Huang, J. L., Yang, P., Peng, Q., Zhang, J. B., Jiang, W. K., Zhang, Z. H., Lin, K., Ro, D. K., Chen, X. Y., Xiong, X. Y., Shang, Y., Huang, S. W., Zeng, J. G., 2017. The genome of medicinal plant Macleaya cordata provides new insights into benzylisoquinoline alkaloids metabolism. Mol. Plant 10 (7), 975 - 989. https: // doi. org / 10.1016 / j. molp. 2017.05.007." type="journal article" year="2017">Liu et al., 2017</bibRefCitation>
|
||
). Take alkaloids
|
||
<emphasis id="B97D0F5E5E2E9E24FD2EAE92259097F7" bold="true" box="[656,668,650,669]" pageId="3" pageNumber="4">2</emphasis>
|
||
(4
|
||
<superScript id="7C7C7E045E2E9E24FD02AE9F25CD97FE" attach="none" box="[700,705,647,660]" fontSize="6" pageId="3" pageNumber="4">′</superScript>
|
||
-demethylcolletine) and
|
||
<emphasis id="B97D0F5E5E2E9E24FEA7AEBE263E97D3" bold="true" box="[281,306,678,697]" pageId="3" pageNumber="4">28</emphasis>
|
||
(colletine) as an example. Both of those compounds were identified as benzyltetrahydroisoquinoline-type alkaloids (
|
||
<figureCitation id="1332CFC95E2E9E24FFD2AEC527BC979B" box="[108,176,733,753]" captionStart="Fig" captionStartId="5.[498,528,1049,1066]" captionTargetBox="[213,1395,159,1013]" captionTargetId="figure-594@5.[187,1400,148,1021]" captionTargetPageId="5" captionText="Fig. 3. TICs of 0-day (A) and 36-day-old (B) tissue culture seedlings." figureDoi="http://doi.org/10.5281/zenodo.8259860" httpUri="https://zenodo.org/record/8259860/files/figure.png" pageId="3" pageNumber="4">Fig. S3</figureCitation>
|
||
). Their structures differed in that alkaloid
|
||
<emphasis id="B97D0F5E5E2E9E24FDE9AEC5257C979A" bold="true" box="[599,624,733,752]" pageId="3" pageNumber="4">28</emphasis>
|
||
has an –OCH
|
||
<subScript id="178DD1095E2E9E24FD47AEFD240E9799" attach="left" box="[761,770,741,755]" fontSize="6" pageId="3" pageNumber="4">3</subScript>
|
||
group at the site of C-4’; however, an –
|
||
<collectionCode id="ED184B895E2E9E24FE76AEE126EB9666" box="[456,487,761,780]" country="Czech Republic" lsid="urn:lsid:biocol.org:col:12554" name="Agricultural Museum of Praha" pageId="3" pageNumber="4" type="Herbarium">OH</collectionCode>
|
||
group was present in the same position for alkaloid
|
||
<emphasis id="B97D0F5E5E2E9E24FE91AF0D26379642" bold="true" box="[303,315,789,808]" pageId="3" pageNumber="4">2</emphasis>
|
||
. In the genus
|
||
<taxonomicName id="4C09A8CF5E2E9E24FE77AF0C25139642" box="[457,543,788,808]" class="Magnoliopsida" family="Papaveraceae" genus="Macleaya" kingdom="Plantae" order="Ranunculales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="genus">
|
||
<emphasis id="B97D0F5E5E2E9E24FE77AF0C25139642" bold="true" box="[457,543,788,808]" italics="true" pageId="3" pageNumber="4">Macleaya</emphasis>
|
||
</taxonomicName>
|
||
, the –
|
||
<collectionCode id="ED184B895E2E9E24FDE0AF0D25719642" box="[606,637,789,808]" country="Czech Republic" lsid="urn:lsid:biocol.org:col:12554" name="Agricultural Museum of Praha" pageId="3" pageNumber="4" type="Herbarium">OH</collectionCode>
|
||
can be transferred to an –OCH
|
||
<subScript id="178DD1095E2E9E24FEACAF202617962C" attach="left" box="[274,283,824,838]" fontSize="6" pageId="3" pageNumber="4">3</subScript>
|
||
group by the methyl transferase (MT), which is an enzyme encoded by various functional genes, such as 6-OMT, Mc2833, and McSMT (Han et al., 2010;
|
||
<bibRefCitation id="EF98AEBD5E2E9E24FEC3AF7125049616" author="Liu, X. B. & Liu, Y. S. & Huang, P. & Ma, Y. S. & Qing, Z. X. & Tang, Q. & Cao, H. F. & Cheng, P. & Zheng, Y. J. & Yuan, Z. J. & Zhou, Y. & Liu, J. F. & Tang, Z. S. & Zhuo, Y. X. & Zhang, Y. C. & Yu, L. L. & Huang, J. L. & Yang, P. & Peng, Q. & Zhang, J. B. & Jiang, W. K. & Zhang, Z. H. & Lin, K. & Ro, D. K. & Chen, X. Y. & Xiong, X. Y. & Shang, Y. & Huang, S. W. & Zeng, J. G." box="[381,520,873,892]" pageId="3" pageNumber="4" pagination="975 - 989" refId="ref6370" refString="Liu, X. B., Liu, Y. S., Huang, P., Ma, Y. S., Qing, Z. X., Tang, Q., Cao, H. F., Cheng, P., Zheng, Y. J., Yuan, Z. J., Zhou, Y., Liu, J. F., Tang, Z. S., Zhuo, Y. X., Zhang, Y. C., Yu, L. L., Huang, J. L., Yang, P., Peng, Q., Zhang, J. B., Jiang, W. K., Zhang, Z. H., Lin, K., Ro, D. K., Chen, X. Y., Xiong, X. Y., Shang, Y., Huang, S. W., Zeng, J. G., 2017. The genome of medicinal plant Macleaya cordata provides new insights into benzylisoquinoline alkaloids metabolism. Mol. Plant 10 (7), 975 - 989. https: // doi. org / 10.1016 / j. molp. 2017.05.007." type="journal article" year="2017">Liu et al., 2017</bibRefCitation>
|
||
). The structural relation of both compounds indicated that alkaloid
|
||
<emphasis id="B97D0F5E5E2E9E24FE5DAF9D26E396F2" bold="true" box="[483,495,901,920]" pageId="3" pageNumber="4">2</emphasis>
|
||
was the precursor of
|
||
<emphasis id="B97D0F5E5E2E9E24FD03AF9D25DA96F2" bold="true" box="[701,726,901,920]" pageId="3" pageNumber="4">28</emphasis>
|
||
.
|
||
</paragraph>
|
||
<paragraph id="8BB6D34C5E2E9E24FF3AAFB9257790C0" blockId="3.[100,771,147,1785]" pageId="3" pageNumber="4">
|
||
The changes in metabolite levels at different growth stages provided further obvious evidence for establishing the metabolic network. The peak area of alkaloid
|
||
<quantity id="4CF17EA95E2E9E24FE95AFC026429686" box="[299,334,984,1004]" metricMagnitude="-2" metricUnit="m" metricValue="5.08" pageId="3" pageNumber="4" unit="in" value="2.0">
|
||
<emphasis id="B97D0F5E5E2E9E24FE95AFC0263B9681" bold="true" box="[299,311,984,1003]" pageId="3" pageNumber="4">2</emphasis>
|
||
in
|
||
</quantity>
|
||
the TICs of tissue culture seedlings continually decreased from 0 to 36 days; however, the peak area of alkaloid
|
||
<emphasis id="B97D0F5E5E2E9E24FD57AFEC240E916D" bold="true" box="[745,770,1012,1031]" pageId="3" pageNumber="4">28</emphasis>
|
||
successively increased (
|
||
<figureCitation id="1332CFC95E2E9E24FEF6A808268C914E" box="[328,384,1040,1060]" captionStart="Fig" captionStartId="5.[498,528,1049,1066]" captionTargetBox="[213,1395,159,1013]" captionTargetId="figure-594@5.[187,1400,148,1021]" captionTargetPageId="5" captionText="Fig. 3. TICs of 0-day (A) and 36-day-old (B) tissue culture seedlings." figureDoi="http://doi.org/10.5281/zenodo.8259860" httpUri="https://zenodo.org/record/8259860/files/figure.png" pageId="3" pageNumber="4">Fig. 3</figureCitation>
|
||
). Interestingly, the level of change was nearly the same, which further demonstrated that the alkaloid
|
||
<emphasis id="B97D0F5E5E2E9E24FD05A83425CB9155" bold="true" box="[699,711,1068,1087]" pageId="3" pageNumber="4">2</emphasis>
|
||
could be converted to
|
||
<emphasis id="B97D0F5E5E2E9E24FEB3A850262A9131" bold="true" box="[269,294,1096,1115]" pageId="3" pageNumber="4">28</emphasis>
|
||
during plant growth. When we used a similar method, the specific metabolic network of other isoquinoline alkaloids in the
|
||
<taxonomicName id="4C09A8CF5E2E9E24FF11A867260991F9" box="[175,261,1151,1171]" class="Magnoliopsida" family="Papaveraceae" genus="Macleaya" kingdom="Plantae" order="Ranunculales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="genus">
|
||
<emphasis id="B97D0F5E5E2E9E24FF11A867260991F9" bold="true" box="[175,261,1151,1171]" italics="true" pageId="3" pageNumber="4">Macleaya</emphasis>
|
||
</taxonomicName>
|
||
genus was also established (
|
||
<figureCitation id="1332CFC95E2E9E24FD86A898257991F9" box="[568,629,1152,1171]" captionStart="Fig" captionStartId="4.[1152,1182,149,166]" captionTargetBox="[101,1126,149,1881]" captionTargetId="figure-7@4.[100,1128,148,1882]" captionTargetPageId="4" captionText="Fig. 2. Proposed metabolic network of isoquinoline alkaloids in the Macleaya genus. a the solid arrow represents verified biosynthesis pathways; b the dotted arrow represents unverified pathways, c the double arrow represents two or more steps needed for biosynthesis; d MT, GOA, and COA are abbreviation for methyl transferase, glycosyltransferase, and cyclooxygenase, respectively; e the red moieties represent the changed substituent groups, and f the blue moieties represent the 13C -labeled benzene ring. (For 6 interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)" figureDoi="http://doi.org/10.5281/zenodo.8259858" httpUri="https://zenodo.org/record/8259858/files/figure.png" pageId="3" pageNumber="4">Fig. 2</figureCitation>
|
||
). Finally, the [
|
||
<emphasis id="B97D0F5E5E2E9E24FFD3A883278391C5" bold="true" box="[109,143,1179,1199]" italics="true" pageId="3" pageNumber="4">ring</emphasis>
|
||
-
|
||
<superScript id="7C7C7E045E2E9E24FF28A88E27A491CE" attach="right" box="[150,168,1174,1188]" fontSize="6" pageId="3" pageNumber="4">13</superScript>
|
||
<collectionCode id="ED184B895E2E9E24FF16A88427B991C5" box="[168,181,1180,1199]" country="Denmark" name="University of Copenhagen" pageId="3" pageNumber="4" type="Herbarium">C</collectionCode>
|
||
<subScript id="178DD1095E2E9E24FF08A8BB27B391DB" attach="right" box="[182,191,1187,1201]" fontSize="6" pageId="3" pageNumber="4">6</subScript>
|
||
]-tyrosine feeding experiment provided visual evidence for establishing the metabolic network of isoquinoline alkaloids in the
|
||
<taxonomicName id="4C09A8CF5E2E9E24FFDAA8CB27B6918D" box="[100,186,1235,1255]" class="Magnoliopsida" family="Papaveraceae" genus="Macleaya" kingdom="Plantae" order="Ranunculales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="genus">
|
||
<emphasis id="B97D0F5E5E2E9E24FFDAA8CB27B6918D" bold="true" box="[100,186,1235,1255]" italics="true" pageId="3" pageNumber="4">Macleaya</emphasis>
|
||
</taxonomicName>
|
||
genus. The [
|
||
<emphasis id="B97D0F5E5E2E9E24FEF3A8CB2663918D" bold="true" box="[333,367,1235,1255]" italics="true" pageId="3" pageNumber="4">ring</emphasis>
|
||
-
|
||
<superScript id="7C7C7E045E2E9E24FEC8A8D6268491B6" attach="right" box="[374,392,1230,1244]" fontSize="6" pageId="3" pageNumber="4">13</superScript>
|
||
<collectionCode id="ED184B895E2E9E24FE36A8CC2699918D" box="[392,405,1236,1255]" country="Denmark" name="University of Copenhagen" pageId="3" pageNumber="4" type="Herbarium">C</collectionCode>
|
||
<subScript id="178DD1095E2E9E24FE2BA8C326929183" attach="left" box="[405,414,1243,1257]" fontSize="6" pageId="3" pageNumber="4">6</subScript>
|
||
]-labeled alkaloids
|
||
<emphasis id="B97D0F5E5E2E9E24FDDCA8CB2562918C" bold="true" box="[610,622,1235,1254]" pageId="3" pageNumber="4">2</emphasis>
|
||
and
|
||
<emphasis id="B97D0F5E5E2E9E24FD13A8CB25CA918C" bold="true" box="[685,710,1235,1254]" pageId="3" pageNumber="4">28</emphasis>
|
||
were detected simultaneously in the TICs of
|
||
<taxonomicName id="4C09A8CF5E2E9E24FE4EA8F7255B9069" box="[496,599,1263,1283]" class="Magnoliopsida" family="Papaveraceae" genus="Macleaya" kingdom="Plantae" order="Ranunculales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="cordata">
|
||
<emphasis id="B97D0F5E5E2E9E24FE4EA8F7255B9069" bold="true" box="[496,599,1263,1283]" italics="true" pageId="3" pageNumber="4">M. cordata</emphasis>
|
||
</taxonomicName>
|
||
seedlings, which further indicated that alkaloid
|
||
<emphasis id="B97D0F5E5E2E9E24FE3CA91326829074" bold="true" box="[386,398,1291,1310]" pageId="3" pageNumber="4">2</emphasis>
|
||
was the precursor of
|
||
<emphasis id="B97D0F5E5E2E9E24FDEAA91325619074" bold="true" box="[596,621,1291,1310]" pageId="3" pageNumber="4">28</emphasis>
|
||
. All [
|
||
<emphasis id="B97D0F5E5E2E9E24FD1FA91225CF9074" bold="true" box="[673,707,1290,1310]" italics="true" pageId="3" pageNumber="4">ring</emphasis>
|
||
-
|
||
<superScript id="7C7C7E045E2E9E24FD74A91E25D0907E" attach="right" box="[714,732,1286,1300]" fontSize="6" pageId="3" pageNumber="4">13</superScript>
|
||
<collectionCode id="ED184B895E2E9E24FD62A91325E59074" box="[732,745,1291,1310]" country="Denmark" name="University of Copenhagen" pageId="3" pageNumber="4" type="Herbarium">C</collectionCode>
|
||
<subScript id="178DD1095E2E9E24FD57A90B25FE904B" attach="left" box="[745,754,1299,1313]" fontSize="6" pageId="3" pageNumber="4">6</subScript>
|
||
]- labeled isoquinoline alkaloids were synthesized from [
|
||
<emphasis id="B97D0F5E5E2E9E24FDCAA93E259A9050" bold="true" box="[628,662,1318,1338]" italics="true" pageId="3" pageNumber="4">ring</emphasis>
|
||
-
|
||
<superScript id="7C7C7E045E2E9E24FD23A93A25A3905A" attach="right" box="[669,687,1314,1328]" fontSize="6" pageId="3" pageNumber="4">13</superScript>
|
||
<collectionCode id="ED184B895E2E9E24FD11A93F25B09050" box="[687,700,1319,1338]" country="Denmark" name="University of Copenhagen" pageId="3" pageNumber="4" type="Herbarium">C</collectionCode>
|
||
<subScript id="178DD1095E2E9E24FD02A93625C99056" attach="left" box="[700,709,1326,1340]" fontSize="6" pageId="3" pageNumber="4">6</subScript>
|
||
]-tyrosine, and their metabolic relationships could be relatively easily determined (
|
||
<figureCitation id="1332CFC95E2E9E24FF10A94727E89018" box="[174,228,1375,1394]" captionStart="Fig" captionStartId="4.[1152,1182,149,166]" captionTargetBox="[101,1126,149,1881]" captionTargetId="figure-7@4.[100,1128,148,1882]" captionTargetPageId="4" captionText="Fig. 2. Proposed metabolic network of isoquinoline alkaloids in the Macleaya genus. a the solid arrow represents verified biosynthesis pathways; b the dotted arrow represents unverified pathways, c the double arrow represents two or more steps needed for biosynthesis; d MT, GOA, and COA are abbreviation for methyl transferase, glycosyltransferase, and cyclooxygenase, respectively; e the red moieties represent the changed substituent groups, and f the blue moieties represent the 13C -labeled benzene ring. (For 6 interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)" figureDoi="http://doi.org/10.5281/zenodo.8259858" httpUri="https://zenodo.org/record/8259858/files/figure.png" pageId="3" pageNumber="4">Fig. 2</figureCitation>
|
||
). In addition, four enzymes, i.e., MT, glycosyltransferase (GTA), cyclooxygenase (COA), and oxidase, were proposed for each specific biosynthesis pathway in this metabolic network.
|
||
</paragraph>
|
||
<paragraph id="8BB6D34C5E2E9E24FF3AA9AB25039393" blockId="3.[100,771,147,1785]" pageId="3" pageNumber="4">
|
||
Although the isoquinoline alkaloids were screened from 45 TICs of samples, which were collected from various parts of
|
||
<taxonomicName id="4C09A8CF5E2E9E24FDEAA9D625A69088" box="[596,682,1486,1506]" class="Magnoliopsida" family="Papaveraceae" genus="Macleaya" kingdom="Plantae" order="Ranunculales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="genus">
|
||
<emphasis id="B97D0F5E5E2E9E24FDEAA9D625A69088" bold="true" box="[596,682,1486,1506]" italics="true" pageId="3" pageNumber="4">Macleaya</emphasis>
|
||
</taxonomicName>
|
||
plants at different growth stages, some intermediate alkaloids were still no detected or were absent in this metabolic network. Take alkaloids
|
||
<emphasis id="B97D0F5E5E2E9E24FD62AA1E240D9373" bold="true" box="[732,769,1542,1561]" pageId="3" pageNumber="4">144</emphasis>
|
||
(sanguinarine) and
|
||
<emphasis id="B97D0F5E5E2E9E24FE92AA3A265D935F" bold="true" box="[300,337,1570,1589]" pageId="3" pageNumber="4">157</emphasis>
|
||
(10-methoxy-sanguinarine) as an example (
|
||
<figureCitation id="1332CFC95E2E9E24FFD2AA2627A0933B" box="[108,172,1598,1617]" captionStart="Fig" captionStartId="5.[498,528,1049,1066]" captionTargetBox="[213,1395,159,1013]" captionTargetId="figure-594@5.[187,1400,148,1021]" captionTargetPageId="5" captionText="Fig. 3. TICs of 0-day (A) and 36-day-old (B) tissue culture seedlings." figureDoi="http://doi.org/10.5281/zenodo.8259860" httpUri="https://zenodo.org/record/8259860/files/figure.png" pageId="3" pageNumber="4">Fig. S3</figureCitation>
|
||
). Sanguinarine can be converted to 10-hydroxy-sanguinarine by an oxidase, and the intermediate alkaloid can be methylated to
|
||
<taxonomicName id="4C09A8CF5E2E9E24FD6BAA4227BC93E3" form="alkaloid" pageId="3" pageNumber="4" rank="form">form alkaloid</taxonomicName>
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||
<quantity id="4CF17EA95E2E9E24FF07AA6E27F693E3" box="[185,250,1654,1673]" metricMagnitude="0" metricUnit="m" metricValue="3.9878" pageId="3" pageNumber="4" unit="in" value="157.0">
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<emphasis id="B97D0F5E5E2E9E24FF07AA6E27D293E3" bold="true" box="[185,222,1654,1673]" pageId="3" pageNumber="4">157</emphasis>
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in
|
||
</quantity>
|
||
the
|
||
<taxonomicName id="4C09A8CF5E2E9E24FE92AA6E26A093E3" box="[300,428,1654,1673]" class="Magnoliopsida" family="Papaveraceae" kingdom="Plantae" order="Ranunculales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="family">Papaveraceae</taxonomicName>
|
||
family (Fig.
|
||
<collectionCode id="ED184B895E2E9E24FD91AA6E253793E3" box="[559,571,1654,1673]" country="Sweden" lsid="urn:lsid:biocol.org:col:15668" name="Department of Botany, Swedish Museum of Natural History" pageId="3" pageNumber="4" type="Herbarium">S</collectionCode>
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||
7) (
|
||
<bibRefCitation id="EF98AEBD5E2E9E24FDDEAA6E279893CF" author="Tanahashi, T. & Zenk, M. H." pageId="3" pageNumber="4" pagination="579 - 586" refId="ref7590" refString="Tanahashi, T., Zenk, M. H., 1990. New hydroxylated benzo [c] phenanthridine alkaloids from Eschscholtzia californica cell suspension cultures. Journal of natural product 53 (3), 579 - 586. https: // doi. org / 10.1021 / np 50069 a 007." type="journal article" year="1990">Tanahashi et al., 1990</bibRefCitation>
|
||
). However, no detectable amount of 10-hydroxy-sanguinarine was found from the TICs of 45
|
||
<taxonomicName id="4C09A8CF5E2E9E24FE28AAB526E093AB" box="[406,492,1709,1729]" class="Magnoliopsida" family="Papaveraceae" genus="Macleaya" kingdom="Plantae" order="Ranunculales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="genus">
|
||
<emphasis id="B97D0F5E5E2E9E24FE28AAB526E093AB" bold="true" box="[406,492,1709,1729]" italics="true" pageId="3" pageNumber="4">Macleaya</emphasis>
|
||
</taxonomicName>
|
||
genus samples. Therefore, 10-hydroxy-sanguinarine was absent from the metabolic network of isoquinoline alkaloids in the
|
||
<taxonomicName id="4C09A8CF5E2E9E24FEC8AAFD26C09393" box="[374,460,1765,1785]" class="Magnoliopsida" family="Papaveraceae" genus="Macleaya" kingdom="Plantae" order="Ranunculales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="genus">
|
||
<emphasis id="B97D0F5E5E2E9E24FEC8AAFD26C09393" bold="true" box="[374,460,1765,1785]" italics="true" pageId="3" pageNumber="4">Macleaya</emphasis>
|
||
</taxonomicName>
|
||
genus.
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |