457 lines
52 KiB
XML
457 lines
52 KiB
XML
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<mods:title id="6782E40BB5EA64CC0A9E3419E933ECBE">Biosynthesis of natural and novel C-glycosylflavones utilising recombinant Oryza sativa C-glycosyltransferase (OsCGT) and Desmodium incanum root proteins</mods:title>
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<mods:namePart id="9B6C6B17696782CE027AE604F7D17195">Hao, B.</mods:namePart>
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<mods:affiliation id="E548266FEA8F7AD71EB479BF688E7772">College of Science, Northwest A & F University, Yangling, Shaanxi 712100, China & Department of Biological Chemistry and Crop Protection, Rothamsted Research, Harpenden, Hertfordshire AL 5 2 JQ, UK</mods:affiliation>
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<mods:namePart id="5F2B755C64A3A05E5782419F746D1C40">Caulfield, J. C.</mods:namePart>
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<mods:namePart id="0BDA3A9FA38801064C667F5F22E8E906">Hamilton, M. L.</mods:namePart>
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<mods:namePart id="D7131E66B127776F937A566DB2D7C1CA">Pickett, J. A.</mods:namePart>
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<mods:namePart id="60A5874A9225989E5965B90B1D4307CB">Midega, C. A. O.</mods:namePart>
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<mods:namePart id="F8BFB536F781E1F690CF07D4FF246D23">Khan, Z. R.</mods:namePart>
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<mods:namePart id="2D47995469376C2CC2CD3E488C289D57">Wang, J.</mods:namePart>
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<mods:namePart id="6825EAF569E3A34C00582C570A743AFA">Hooper, A. M.</mods:namePart>
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<mods:title id="1E9EF97D136483A774BC3CE95761B240">Phytochemistry</mods:title>
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<mods:date id="505D97562C0D316D47A617E7651EBB64">2016</mods:date>
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<mods:number id="119CBB49AC7BDBD8190C496AF547609D">2016-05-31</mods:number>
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<mods:number id="D141BBCE5691535C8EB2DDDB1D4779DB">125</mods:number>
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<treatment id="E9788781A153FFE1E936F900FD22F97E" ID-DOI="http://doi.org/10.5281/zenodo.10530339" ID-Zenodo-Dep="10530339" LSID="urn:lsid:plazi:treatment:E9788781A153FFE1E936F900FD22F97E" httpUri="http://treatment.plazi.org/id/E9788781A153FFE1E936F900FD22F97E" lastPageId="7" lastPageNumber="77" pageId="4" pageNumber="77">
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<subSubSection id="29CB651CA153FFE2E936F900FC60F97F" pageId="4" pageNumber="77" type="nomenclature">
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<paragraph id="616E3697A153FFE2E936F900FC60F97F" blockId="4.[831,1500,1715,1791]" pageId="4" pageNumber="77">
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<emphasis id="53A5EA85A153FFE2E936F900FC60F97F" italics="true" pageId="4" pageNumber="77">
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2.6. Synthesis of 6,8-di-C-glycosylflavones using 6-C-glucosyl-2- hydroxyflavanone substrates created by OsCGT and CGT enzymes from
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<taxonomicName id="A6D14D14A153FFE2E936F958FC60F97F" ID-CoL="3538J" authority="DC." box="[831,942,1771,1791]" class="Magnoliopsida" family="Fabaceae" genus="Desmodium" kingdom="Plantae" order="Fabales" pageId="4" pageNumber="77" phylum="Tracheophyta" rank="species" species="incanum">D. incanum</taxonomicName>
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</emphasis>
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</paragraph>
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<paragraph id="616E3697A153FFE1E957F897FD22F97E" blockId="4.[831,1501,1828,2015]" lastBlockId="7.[87,757,1464,1790]" lastPageId="7" lastPageNumber="80" pageId="4" pageNumber="77">
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The results of incubating synthetic 2-hydroxyflavanones with UDP-glucose and OsCGT (
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<tableCitation id="2C53032CA153FFE2EE4EF8F3FB53F8D3" box="[1095,1181,1856,1875]" captionStart="Table 1" captionStartId="3.[87,131,183,197]" captionTargetPageId="3" captionText="Table 1 Generation of natural product mono-C-glucosylflavones from 2-hydroxyflavanones and UDP-glucose by the Oryza sativa OsCGT." httpUri="http://table.plazi.org/id/35AE661FA154FFE5EA5EFF04FB81FF5C" pageId="4" pageNumber="77" tableUuid="35AE661FA154FFE5EA5EFF04FB81FF5C">Tables 1</tableCitation>
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and
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||
<tableCitation id="2C53032CA153FFE2EEDAF8F3FB2EF8D3" box="[1235,1248,1856,1875]" captionStart="Table 2" captionStartId="5.[87,131,183,197]" captionTargetPageId="5" captionText="Table 2 Generation of novel mono-C-glucosylfavones from 2-hydroxyflavanones and UDP-glucose by the Oryza sativa OsCGT. OH R3' R3' HO R' OH R'4 R4' 3 OH O R4' HO OHO O HO OH R5' R5' UDP-Glu HO O O R5' HCl OH O OH O HO OH OH O OH" httpUri="http://table.plazi.org/id/35AE661FA152FFE3EA5EFF04FC34FF5C" pageId="4" pageNumber="77" tableUuid="35AE661FA152FFE3EA5EFF04FC34FF5C">2</tableCitation>
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) revealed substrate that can be used to generate
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<emphasis id="53A5EA85A153FFE2EE49F8E8FB82F8EF" box="[1088,1100,1883,1903]" italics="true" pageId="4" pageNumber="77">
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<collectionCode id="07C0AE52A153FFE2EE49F8E8FB82F8EF" box="[1088,1100,1883,1903]" country="Denmark" name="University of Copenhagen" pageId="4" pageNumber="77" type="Herbarium">C</collectionCode>
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</emphasis>
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-glucosyl-2-hydroxyflavanones (
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<emphasis id="53A5EA85A153FFE2EF9FF8EFFA6DF8EF" bold="true" box="[1430,1443,1884,1903]" pageId="4" pageNumber="77">4</emphasis>
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||
) that may be themselves substrates for a second glycosylations. In our work to understand the biosynthesis of di-
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||
<emphasis id="53A5EA85A153FFE2EF0DF820FADEF827" box="[1284,1296,1939,1959]" italics="true" pageId="4" pageNumber="77">
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<collectionCode id="07C0AE52A153FFE2EF0DF820FADEF827" box="[1284,1296,1939,1959]" country="Denmark" name="University of Copenhagen" pageId="4" pageNumber="77" type="Herbarium">C</collectionCode>
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</emphasis>
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||
-glycosylflavones in the allelopathic root exudates of
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||
<taxonomicName id="A6D14D14A153FFE2EE8FF81CFB3DF843" box="[1158,1267,1967,1987]" class="Magnoliopsida" family="Fabaceae" genus="Desmodium" kingdom="Plantae" order="Fabales" pageId="4" pageNumber="77" phylum="Tracheophyta" rank="species" species="incanum">
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<emphasis id="53A5EA85A153FFE2EE8FF81CFB3DF843" box="[1158,1267,1967,1987]" italics="true" pageId="4" pageNumber="77">D. incanum</emphasis>
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</taxonomicName>
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we have demonstrated that the soluble plant enzyme extracts can
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<emphasis id="53A5EA85A153FFE2EF59F879FA92F85E" box="[1360,1372,1994,2014]" italics="true" pageId="4" pageNumber="77">
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<collectionCode id="07C0AE52A153FFE2EF59F879FA92F85E" box="[1360,1372,1994,2014]" country="Denmark" name="University of Copenhagen" pageId="4" pageNumber="77" type="Herbarium">C</collectionCode>
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</emphasis>
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||
-glucosylate,
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||
<emphasis id="53A5EA85A151FFE0EA78FF06FFB3FF49" box="[113,125,181,201]" italics="true" pageId="6" pageNumber="79">
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<collectionCode id="07C0AE52A151FFE0EA78FF06FFB3FF49" box="[113,125,181,201]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="79" type="Herbarium">C</collectionCode>
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</emphasis>
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||
-galactosylate and
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||
<emphasis id="53A5EA85A151FFE0EB53FF06FEA8FF49" box="[346,358,181,201]" italics="true" pageId="6" pageNumber="79">
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<collectionCode id="07C0AE52A151FFE0EB53FF06FEA8FF49" box="[346,358,181,201]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="79" type="Herbarium">C</collectionCode>
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</emphasis>
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-arabinoslyate the mono-
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<emphasis id="53A5EA85A151FFE0E88CFF06FD5FFF49" box="[645,657,181,201]" italics="true" pageId="6" pageNumber="79">
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<collectionCode id="07C0AE52A151FFE0E88CFF06FD5FFF49" box="[645,657,181,201]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="79" type="Herbarium">C</collectionCode>
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</emphasis>
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||
-glucosylflavanones
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<emphasis id="53A5EA85A151FFE0EAC5FF61FF2BFF65" bold="true" box="[204,229,210,229]" pageId="6" pageNumber="79">4a</emphasis>
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to produce di-
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<emphasis id="53A5EA85A151FFE0EB89FF62FE42FF65" box="[384,396,209,229]" italics="true" pageId="6" pageNumber="79">
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<collectionCode id="07C0AE52A151FFE0EB89FF62FE42FF65" box="[384,396,209,229]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="79" type="Herbarium">C</collectionCode>
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</emphasis>
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-glycosylflavonones that dehydrate to the respective flavones (
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<bibRefCitation id="05404B66A151FFE0EB66FF5DFD9EFE81" author="Hamilton, M. L. & Kuate, S. P. & Brazier-Hicks, M. & Caulfield, J. C. & Rose, R. & Edwards, R. & Torto, B. & Pickett, J. A. & Hooper, A. M." box="[367,592,238,257]" pageId="6" pageNumber="79" pagination="169 - 176" refId="ref23296" refString="Hamilton, M. L., Kuate, S. P., Brazier-Hicks, M., Caulfield, J. C., Rose, R., Edwards, R., Torto, B., Pickett, J. A., Hooper, A. M., 2012. Elucidation of the biosynthesis of the di- C - glycosylflavone isoschaftoside, an allelopathic component from Desmodium spp. that inhibits Striga spp. development. Phytochemistry 84, 169 - 176." type="journal article" year="2012">Hamilton et al., 2012</bibRefCitation>
|
||
;
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<bibRefCitation id="05404B66A151FFE0E855FF5DFCCCFE81" author="Hao, B. & Caulfield, J. C. & Hamilton, M. L. & Pickett, J. A. & Midega, C. A. O. & Khan, Z. R. & Wang, J. R. & Hooper, A. M." box="[604,770,238,257]" pageId="6" pageNumber="79" refId="ref23708" refString="Hao, B., Caulfield, J. C., Hamilton, M. L., Pickett, J. A., Midega, C. A. O., Khan, Z. R., Wang, J. R., Hooper, A. M., 2015. The biosynthesis of allelopathic di- C - glycosylflavones from the roots of Desmodium incanum (G. Mey.) DC. Org. Biomol. Chem. http: // dx. doi. org / 10.1039 / C 5 OB 01926 E. Advance Article." type="book" year="2015">Hao et al., 2015</bibRefCitation>
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||
). We therefore used synthetic 2-hydroxyflavanones that are well accepted by the OsCGT to generate natural and novel
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<emphasis id="53A5EA85A151FFE0E897FE96FD64FEB9" box="[670,682,293,313]" italics="true" pageId="6" pageNumber="79">
|
||
<collectionCode id="07C0AE52A151FFE0E897FE96FD64FEB9" box="[670,682,293,313]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="79" type="Herbarium">C</collectionCode>
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||
</emphasis>
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||
-glucosyl-2-hydroxyflavanones (
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<tableCitation id="2C53032CA151FFE0EB5AFEF1FE55FED5" box="[339,411,322,341]" captionStart="Table 3" captionStartId="5.[87,131,1065,1079]" captionTargetBox="[110,1451,1427,1958]" captionTargetPageId="5" captionText="Table 3 2-Hydroxyflavanones (3) and C-glucosylflvanones (4), generated by OsCGT, introduced to D. incanum soluble root proteins with UDP-sugar donors to generate C-glucosylflavones (5,6) or di-C-glycosylflavones (7–11). *(Hao et al., 2015)." httpUri="http://table.plazi.org/id/35AE661FA152FFE3EA5EFB9AFDD8FBE4" pageId="6" pageNumber="79" tableUuid="35AE661FA152FFE3EA5EFB9AFDD8FBE4">Table 3</tableCitation>
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). By using recombinant OsCGT, these unstable intermediates can be generated in good yields and purity without the need for separation from other flavonoids. The incubation of the substrates with UDP-glucose is expected to give three products (
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<emphasis id="53A5EA85A151FFE0EAD5FE02FECDFE44" bold="true" box="[220,259,433,453]" pageId="6" pageNumber="79">7–9</emphasis>
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), rather than one containing two glucose groups, as the
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<taxonomicName id="A6D14D14A151FFE0EAB7FE7FFE4BFE60" box="[190,389,460,480]" class="Magnoliopsida" family="Fabaceae" genus="Desmodium" kingdom="Plantae" order="Fabales" pageId="6" pageNumber="85" phylum="Tracheophyta" rank="subSpecies" species="incanum" subSpecies="soluble">
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<emphasis id="53A5EA85A151FFE0EAB7FE7FFEFCFE60" box="[190,306,460,480]" italics="true" pageId="6" pageNumber="79">D. incanum</emphasis>
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||
soluble
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||
</taxonomicName>
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||
enzyme extract is able to isomerise UDP-glucose to UDP-galactose which is subsequently incorporated and after dehydration can be fixed in either the
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<collectionCode id="07C0AE52A151FFE0E858FDB6FDA7FD98" box="[593,617,517,536]" pageId="6" pageNumber="79">C-</collectionCode>
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6 or
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<collectionCode id="07C0AE52A151FFE0E89CFDB6FD63FD98" box="[661,685,517,536]" pageId="6" pageNumber="79">C-</collectionCode>
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8 position to give two regiosiomers (
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<figureCitation id="F9EA2A12A151FFE0EB75FD92FE13FDB4" box="[380,477,545,564]" captionStart="Scheme 1" captionStartId="1.[87,152,1616,1630]" captionTargetBox="[170,1380,181,1586]" captionTargetId="figure-219@1.[170,1380,181,1586]" captionTargetPageId="1" captionText="Scheme 1. Production of di-C-glycosides by the soluble root protein of D. incanum and suitable sugar donor cofactors from the subtrate generated by recombinant OsCGT." figureDoi="http://doi.org/10.5281/zenodo.10530364" httpUri="https://zenodo.org/record/10530364/files/figure.png" pageId="6" pageNumber="79">Scheme 1</figureCitation>
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) (
|
||
<bibRefCitation id="05404B66A151FFE0EBFDFD92FD5DFDB4" author="Hao, B. & Caulfield, J. C. & Hamilton, M. L. & Pickett, J. A. & Midega, C. A. O. & Khan, Z. R. & Wang, J. R. & Hooper, A. M." box="[500,659,545,564]" pageId="6" pageNumber="79" refId="ref23708" refString="Hao, B., Caulfield, J. C., Hamilton, M. L., Pickett, J. A., Midega, C. A. O., Khan, Z. R., Wang, J. R., Hooper, A. M., 2015. The biosynthesis of allelopathic di- C - glycosylflavones from the roots of Desmodium incanum (G. Mey.) DC. Org. Biomol. Chem. http: // dx. doi. org / 10.1039 / C 5 OB 01926 E. Advance Article." type="book" year="2015">Hao et al., 2015</bibRefCitation>
|
||
). The incorporation of UDP-arabinose likewise produces two products (
|
||
<emphasis id="53A5EA85A151FFE0E8C3FD8EFD2DFDD0" bold="true" box="[714,739,573,592]" pageId="6" pageNumber="79">10</emphasis>
|
||
,
|
||
<emphasis id="53A5EA85A151FFE0E8E0FD8EFCCCFDD0" bold="true" box="[745,770,573,592]" pageId="6" pageNumber="79">11</emphasis>
|
||
), regioisomers with the
|
||
<emphasis id="53A5EA85A151FFE0EB5EFDEBFEADFDEC" box="[343,355,600,620]" italics="true" pageId="6" pageNumber="79">
|
||
<collectionCode id="07C0AE52A151FFE0EB5EFDEBFEADFDEC" box="[343,355,600,620]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="79" type="Herbarium">C</collectionCode>
|
||
</emphasis>
|
||
-arabinose in either the 6 or 8 position. In all cases, where the correct number of novel products was detected with the correct molecular weight, the fragmentation pattern was subsequently carried out under high cone voltage ESIMS conditions to demonstrate that the products are indeed di-
|
||
<emphasis id="53A5EA85A151FFE0E859FD74FD92FD5B" box="[592,604,711,731]" italics="true" pageId="6" pageNumber="79">
|
||
<collectionCode id="07C0AE52A151FFE0E859FD74FD92FD5B" box="[592,604,711,731]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="79" type="Herbarium">C</collectionCode>
|
||
</emphasis>
|
||
-glycosylflavones. In the case of
|
||
<emphasis id="53A5EA85A151FFE0EB09FD50FEC2FD77" box="[256,268,739,759]" italics="true" pageId="6" pageNumber="79">
|
||
<collectionCode id="07C0AE52A151FFE0EB09FD50FEC2FD77" box="[256,268,739,759]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="79" type="Herbarium">C</collectionCode>
|
||
</emphasis>
|
||
-hexosylflavones, loss of 90 and 120 amus indicate the correct
|
||
<emphasis id="53A5EA85A151FFE0EAECFD4CFF3FFC93" box="[229,241,767,787]" italics="true" pageId="6" pageNumber="79">
|
||
<collectionCode id="07C0AE52A151FFE0EAECFD4CFF3FFC93" box="[229,241,767,787]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="79" type="Herbarium">C</collectionCode>
|
||
</emphasis>
|
||
-link and with
|
||
<emphasis id="53A5EA85A151FFE0EB81FD4CFE5AFC93" box="[392,404,767,787]" italics="true" pageId="6" pageNumber="79">
|
||
<collectionCode id="07C0AE52A151FFE0EB81FD4CFE5AFC93" box="[392,404,767,787]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="79" type="Herbarium">C</collectionCode>
|
||
</emphasis>
|
||
-arabinosylflavones, loss of 60 and 90 amus is indicative of the correct structure (
|
||
<figureCitation id="F9EA2A12A151FFE0E83CFCAFFDA3FCAF" box="[565,621,796,815]" captionStart="Fig" captionStartId="4.[190,216,605,619]" captionTargetBox="[386,1220,181,576]" captionTargetId="figure-248@4.[386,1221,181,576]" captionTargetPageId="4" captionText="Fig. 1. Fragmentation of C-hexosides and C-pentosides under high cone voltage ESIMS conditions to generate fragments losses of 60, 90 and 120 amus." figureDoi="http://doi.org/10.5281/zenodo.10485003" httpUri="https://zenodo.org/record/10485003/files/figure.png" pageId="6" pageNumber="79">Fig. 1</figureCitation>
|
||
). The results of these experiment showed that there was a greater relaxed specificity for
|
||
<emphasis id="53A5EA85A151FFE0EB1CFCE0FEEFFCE7" box="[277,289,851,871]" italics="true" pageId="6" pageNumber="79">
|
||
<collectionCode id="07C0AE52A151FFE0EB1CFCE0FEEFFCE7" box="[277,289,851,871]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="79" type="Herbarium">C</collectionCode>
|
||
</emphasis>
|
||
-glucosylation and
|
||
<emphasis id="53A5EA85A151FFE0EBFEFCE0FDCDFCE7" box="[503,515,851,871]" italics="true" pageId="6" pageNumber="79">
|
||
<collectionCode id="07C0AE52A151FFE0EBFEFCE0FDCDFCE7" box="[503,515,851,871]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="79" type="Herbarium">C</collectionCode>
|
||
</emphasis>
|
||
-galactosylation than for
|
||
<emphasis id="53A5EA85A151FFE0E936FF06FC85FF49" box="[831,843,181,201]" italics="true" pageId="6" pageNumber="79">
|
||
<collectionCode id="07C0AE52A151FFE0E936FF06FC85FF49" box="[831,843,181,201]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="79" type="Herbarium">C</collectionCode>
|
||
</emphasis>
|
||
-arabinosylation. Substrates
|
||
<emphasis id="53A5EA85A151FFE0EE70FF05FB5FFF49" bold="true" box="[1145,1169,182,201]" pageId="6" pageNumber="79">4a</emphasis>
|
||
,
|
||
<emphasis id="53A5EA85A151FFE0EE9EFF05FB6AFF49" bold="true" box="[1175,1188,182,201]" pageId="6" pageNumber="79">b</emphasis>
|
||
,
|
||
<emphasis id="53A5EA85A151FFE0EEA0FF05FB79FF49" bold="true" box="[1193,1207,182,201]" pageId="6" pageNumber="79">d</emphasis>
|
||
,
|
||
<emphasis id="53A5EA85A151FFE0EEB5FF05FB0AFF49" bold="true" box="[1212,1220,182,201]" pageId="6" pageNumber="79">f</emphasis>
|
||
,
|
||
<emphasis id="53A5EA85A151FFE0EEC0FF05FB1BFF49" bold="true" box="[1225,1237,182,201]" pageId="6" pageNumber="79">g</emphasis>
|
||
,
|
||
<emphasis id="53A5EA85A151FFE0EED3FF05FB26FF49" bold="true" box="[1242,1256,182,201]" pageId="6" pageNumber="79">h</emphasis>
|
||
,
|
||
<emphasis id="53A5EA85A151FFE0EEE4FF05FAE1FF49" bold="true" box="[1261,1327,182,201]" pageId="6" pageNumber="79">k,o,p,s</emphasis>
|
||
all produced 3 new metabolites when incubated with UDP-glucose and
|
||
<taxonomicName id="A6D14D14A151FFE0EFC1FF62FC0CFE81" class="Magnoliopsida" family="Fabaceae" genus="Desmodium" kingdom="Plantae" order="Fabales" pageId="6" pageNumber="85" phylum="Tracheophyta" rank="subSpecies" species="incanum" subSpecies="root">
|
||
<emphasis id="53A5EA85A151FFE0EFC1FF62FC5DFE81" italics="true" pageId="6" pageNumber="79">D. incanum</emphasis>
|
||
root
|
||
</taxonomicName>
|
||
protein, deduced to be structures
|
||
<emphasis id="53A5EA85A151FFE0EF10FF5DFAE8FE81" bold="true" box="[1305,1318,238,257]" pageId="6" pageNumber="79">7</emphasis>
|
||
,
|
||
<emphasis id="53A5EA85A151FFE0EF39FF5DFAF3FE81" bold="true" box="[1328,1341,238,257]" pageId="6" pageNumber="79">8</emphasis>
|
||
and
|
||
<emphasis id="53A5EA85A151FFE0EF64FF5DFAB4FE81" bold="true" box="[1389,1402,238,257]" pageId="6" pageNumber="79">9</emphasis>
|
||
by ESIMS mass spectrometry (Supplementary data). In the case of
|
||
<emphasis id="53A5EA85A151FFE0EF73FEB9FA5BFE9D" bold="true" box="[1402,1429,266,285]" pageId="6" pageNumber="79">4b</emphasis>
|
||
, as the products are already present in
|
||
<taxonomicName id="A6D14D14A151FFE0EE84FE96FB30FEB9" box="[1165,1278,293,313]" class="Magnoliopsida" family="Fabaceae" genus="Desmodium" kingdom="Plantae" order="Fabales" pageId="6" pageNumber="79" phylum="Tracheophyta" rank="species" species="incanum">
|
||
<emphasis id="53A5EA85A151FFE0EE84FE96FB30FEB9" box="[1165,1278,293,313]" italics="true" pageId="6" pageNumber="79">D. incanum</emphasis>
|
||
</taxonomicName>
|
||
and are co-extracted with the proteins, the labelled sugar moiety UDP-α- D-[UL-
|
||
<superScript id="96A49BDFA151FFE0EF8AFE8DFA58FECA" attach="both" box="[1411,1430,318,330]" fontSize="5" pageId="6" pageNumber="79">13</superScript>
|
||
<collectionCode id="07C0AE52A151FFE0EF9CFEF1FA6CFED5" box="[1429,1442,322,341]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="79" type="Herbarium">C</collectionCode>
|
||
<subScript id="FD5534D2A151FFE0EFAAFEF8FA62FED7" attach="right" box="[1443,1452,331,343]" fontSize="5" pageId="6" pageNumber="79">6</subScript>
|
||
]glucose was used and incorporation judged by presence of the labelled [
|
||
<collectionCode id="07C0AE52A151FFE0E94DFEC9FC95FE0D" box="[836,859,378,397]" country="Germany" lsid="urn:lsid:biocol.org:col:15637" name="Botanische Staatssammlung München" pageId="6" pageNumber="79" type="Herbarium">M</collectionCode>
|
||
<emphasis id="53A5EA85A151FFE0E952FECAFCA2FE0C" box="[859,876,377,396]" italics="true" pageId="6" pageNumber="79">—</emphasis>
|
||
<collectionCode id="07C0AE52A151FFE0E965FECAFCB0FE0C" box="[876,894,377,396]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="6" pageNumber="79" type="Herbarium">H</collectionCode>
|
||
+6]
|
||
<emphasis id="53A5EA85A151FFE0E994FEC6FC67FE02" box="[925,937,373,386]" italics="true" pageId="6" pageNumber="79">
|
||
<superScript id="96A49BDFA151FFE0E994FEC6FC67FE02" attach="left" box="[925,937,373,386]" fontSize="5" pageId="6" pageNumber="79">—</superScript>
|
||
</emphasis>
|
||
615 ion with six
|
||
<superScript id="96A49BDFA151FFE0EE5DFEC5FBA9FE02" attach="right" box="[1108,1127,374,386]" fontSize="5" pageId="6" pageNumber="79">13</superScript>
|
||
<collectionCode id="07C0AE52A151FFE0EE6EFEC9FBBAFE0D" box="[1127,1140,378,397]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="79" type="Herbarium">C</collectionCode>
|
||
atoms. The ion trace, low cone voltage ESIMS spectrum and fragmented high cone voltage ESIMS spectra from compounds
|
||
<emphasis id="53A5EA85A151FFE0EE45FE02FBA8FE44" bold="true" box="[1100,1126,433,452]" pageId="6" pageNumber="79">7h</emphasis>
|
||
,
|
||
<emphasis id="53A5EA85A151FFE0EE7FFE02FB5EFE44" bold="true" box="[1142,1168,433,452]" pageId="6" pageNumber="79">8h</emphasis>
|
||
, and
|
||
<emphasis id="53A5EA85A151FFE0EEC6FE02FB27FE44" bold="true" box="[1231,1257,433,452]" pageId="6" pageNumber="79">9h</emphasis>
|
||
produced from
|
||
<emphasis id="53A5EA85A151FFE0EF91FE02FA7CFE44" bold="true" box="[1432,1458,433,452]" pageId="6" pageNumber="79">4h</emphasis>
|
||
are shown (
|
||
<figureCitation id="F9EA2A12A151FFE0E999FE7EFC08FE60" box="[912,966,461,480]" captionStart="Fig" captionStartId="6.[113,139,1976,1990]" captionTargetBox="[145,1468,933,1946]" captionTargetId="figure-602@6.[144,1469,932,1947]" captionTargetPageId="6" captionText="Fig. 3. (A) Ion scan for [M—H] — 621 showing three new metabolites found in (B) the LCMS ion trace. (C) Molecular ions of three new metabolites and (D) fragmentation under high cone voltage showing C-link fragments." figureDoi="http://doi.org/10.5281/zenodo.10485007" httpUri="https://zenodo.org/record/10485007/files/figure.png" pageId="6" pageNumber="79">Fig. 3</figureCitation>
|
||
). The selective ion trace at 621 amus (
|
||
<figureCitation id="F9EA2A12A151FFE0EF42FE7EFA5EFE60" box="[1355,1424,461,480]" captionStart="Fig" captionStartId="6.[113,139,1976,1990]" captionTargetBox="[145,1468,933,1946]" captionTargetId="figure-602@6.[144,1469,932,1947]" captionTargetPageId="6" captionText="Fig. 3. (A) Ion scan for [M—H] — 621 showing three new metabolites found in (B) the LCMS ion trace. (C) Molecular ions of three new metabolites and (D) fragmentation under high cone voltage showing C-link fragments." figureDoi="http://doi.org/10.5281/zenodo.10485007" httpUri="https://zenodo.org/record/10485007/files/figure.png" pageId="6" pageNumber="79">Fig. 3A</figureCitation>
|
||
) shows three new metabolites with the correct ion ([
|
||
<collectionCode id="07C0AE52A151FFE0EF1BFE5AFAE4FE7C" box="[1298,1322,489,508]" country="Germany" lsid="urn:lsid:biocol.org:col:15637" name="Botanische Staatssammlung München" pageId="6" pageNumber="79" type="Herbarium">M</collectionCode>
|
||
<emphasis id="53A5EA85A151FFE0EF23FE5AFAF5FE7C" box="[1322,1339,489,508]" italics="true" pageId="6" pageNumber="79">—</emphasis>
|
||
<collectionCode id="07C0AE52A151FFE0EF32FE5AFA83FE7C" box="[1339,1357,489,508]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="6" pageNumber="79" type="Herbarium">H</collectionCode>
|
||
]
|
||
<emphasis id="53A5EA85A151FFE0EF5AFE56FA91FE72" box="[1363,1375,485,498]" italics="true" pageId="6" pageNumber="79">
|
||
<superScript id="96A49BDFA151FFE0EF5AFE56FA91FE72" attach="left" box="[1363,1375,485,498]" fontSize="5" pageId="6" pageNumber="79">—</superScript>
|
||
</emphasis>
|
||
621) which was shown to be the anticipated molecular ion (
|
||
<figureCitation id="F9EA2A12A151FFE0EF2FFDB6FAA5FD98" box="[1318,1387,517,536]" captionStart="Fig" captionStartId="6.[113,139,1976,1990]" captionTargetBox="[145,1468,933,1946]" captionTargetId="figure-602@6.[144,1469,932,1947]" captionTargetPageId="6" captionText="Fig. 3. (A) Ion scan for [M—H] — 621 showing three new metabolites found in (B) the LCMS ion trace. (C) Molecular ions of three new metabolites and (D) fragmentation under high cone voltage showing C-link fragments." figureDoi="http://doi.org/10.5281/zenodo.10485007" httpUri="https://zenodo.org/record/10485007/files/figure.png" pageId="6" pageNumber="79">Fig. 3C</figureCitation>
|
||
). Fragmentation shows sequential losses of 90 ([
|
||
<collectionCode id="07C0AE52A151FFE0EEF0FD92FADFFDB4" box="[1273,1297,545,564]" country="Germany" lsid="urn:lsid:biocol.org:col:15637" name="Botanische Staatssammlung München" pageId="6" pageNumber="79" type="Herbarium">M</collectionCode>
|
||
<emphasis id="53A5EA85A151FFE0EF18FD92FAECFDB4" box="[1297,1314,545,564]" italics="true" pageId="6" pageNumber="79">—</emphasis>
|
||
<collectionCode id="07C0AE52A151FFE0EF28FD92FAFFFDB4" box="[1313,1329,545,564]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="6" pageNumber="79" type="Herbarium">H</collectionCode>
|
||
<emphasis id="53A5EA85A151FFE0EF3BFD92FA8DFDB4" box="[1330,1347,545,564]" italics="true" pageId="6" pageNumber="79">—</emphasis>
|
||
90]
|
||
<emphasis id="53A5EA85A151FFE0EF6DFDAFFABEFDA9" box="[1380,1392,540,553]" italics="true" pageId="6" pageNumber="79">
|
||
<superScript id="96A49BDFA151FFE0EF6DFDAFFABEFDA9" attach="left" box="[1380,1392,540,553]" fontSize="5" pageId="6" pageNumber="79">—</superScript>
|
||
</emphasis>
|
||
531 and [
|
||
<collectionCode id="07C0AE52A151FFE0E94DFD8EFC95FDD0" box="[836,859,573,592]" country="Germany" lsid="urn:lsid:biocol.org:col:15637" name="Botanische Staatssammlung München" pageId="6" pageNumber="79" type="Herbarium">M</collectionCode>
|
||
<emphasis id="53A5EA85A151FFE0E952FD8EFCA2FDD0" box="[859,876,573,592]" italics="true" pageId="6" pageNumber="79">—</emphasis>
|
||
<collectionCode id="07C0AE52A151FFE0E965FD8EFCB2FDD0" box="[876,892,573,592]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="6" pageNumber="79" type="Herbarium">H</collectionCode>
|
||
<emphasis id="53A5EA85A151FFE0E975FD8EFC43FDD0" box="[892,909,573,592]" italics="true" pageId="6" pageNumber="79">—</emphasis>
|
||
180]
|
||
<emphasis id="53A5EA85A151FFE0E9B2FD8BFC09FDC5" box="[955,967,568,581]" italics="true" pageId="6" pageNumber="79">
|
||
<superScript id="96A49BDFA151FFE0E9B2FD8BFC09FDC5" attach="left" box="[955,967,568,581]" fontSize="5" pageId="6" pageNumber="79">—</superScript>
|
||
</emphasis>
|
||
441} and 120 amus ([
|
||
<collectionCode id="07C0AE52A151FFE0EEEFFD8EFB30FDD0" box="[1254,1278,573,592]" country="Germany" lsid="urn:lsid:biocol.org:col:15637" name="Botanische Staatssammlung München" pageId="6" pageNumber="79" type="Herbarium">M</collectionCode>
|
||
<emphasis id="53A5EA85A151FFE0EEF7FD8EFAC1FDD0" box="[1278,1295,573,592]" italics="true" pageId="6" pageNumber="79">—</emphasis>
|
||
<collectionCode id="07C0AE52A151FFE0EF06FD8EFAD1FDD0" box="[1295,1311,573,592]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="6" pageNumber="79" type="Herbarium">H</collectionCode>
|
||
<emphasis id="53A5EA85A151FFE0EF16FD8EFAFEFDD0" box="[1311,1328,573,592]" italics="true" pageId="6" pageNumber="79">—</emphasis>
|
||
120]
|
||
<emphasis id="53A5EA85A151FFE0EF57FD8BFAA4FDC5" box="[1374,1386,568,581]" italics="true" pageId="6" pageNumber="79">
|
||
<superScript id="96A49BDFA151FFE0EF57FD8BFAA4FDC5" attach="left" box="[1374,1386,568,581]" fontSize="5" pageId="6" pageNumber="79">—</superScript>
|
||
</emphasis>
|
||
501 and [
|
||
<collectionCode id="07C0AE52A151FFE0E94DFDEAFC95FDEC" box="[836,859,601,620]" country="Germany" lsid="urn:lsid:biocol.org:col:15637" name="Botanische Staatssammlung München" pageId="6" pageNumber="79" type="Herbarium">M</collectionCode>
|
||
<emphasis id="53A5EA85A151FFE0E952FDEAFCA2FDEC" box="[859,876,601,620]" italics="true" pageId="6" pageNumber="79">—</emphasis>
|
||
<collectionCode id="07C0AE52A151FFE0E965FDEAFCB2FDEC" box="[876,892,601,620]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="6" pageNumber="79" type="Herbarium">H</collectionCode>
|
||
<emphasis id="53A5EA85A151FFE0E975FDEAFC43FDEC" box="[892,909,601,620]" italics="true" pageId="6" pageNumber="79">—</emphasis>
|
||
240]
|
||
<emphasis id="53A5EA85A151FFE0E9B2FDE7FC09FDE1" box="[955,967,596,609]" italics="true" pageId="6" pageNumber="79">
|
||
<superScript id="96A49BDFA151FFE0E9B2FDE7FC09FDE1" attach="left" box="[955,967,596,609]" fontSize="5" pageId="6" pageNumber="79">—</superScript>
|
||
</emphasis>
|
||
381) and combinations of losses ([
|
||
<collectionCode id="07C0AE52A151FFE0EF3EFDEAFA81FDEC" box="[1335,1359,601,620]" country="Germany" lsid="urn:lsid:biocol.org:col:15637" name="Botanische Staatssammlung München" pageId="6" pageNumber="79" type="Herbarium">M</collectionCode>
|
||
<emphasis id="53A5EA85A151FFE0EF47FDEAFA91FDEC" box="[1358,1375,601,620]" italics="true" pageId="6" pageNumber="79">—</emphasis>
|
||
<collectionCode id="07C0AE52A151FFE0EF56FDEAFAA1FDEC" box="[1375,1391,601,620]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="6" pageNumber="79" type="Herbarium">H</collectionCode>
|
||
<emphasis id="53A5EA85A151FFE0EF66FDEAFA4EFDEC" box="[1391,1408,601,620]" italics="true" pageId="6" pageNumber="79">—</emphasis>
|
||
90-120]
|
||
<emphasis id="53A5EA85A151FFE0EFD9FDE7FA12FDE1" box="[1488,1500,596,609]" italics="true" pageId="6" pageNumber="79">
|
||
<superScript id="96A49BDFA151FFE0EFD9FDE7FA12FDE1" attach="none" box="[1488,1500,596,609]" fontSize="5" pageId="6" pageNumber="79">—</superScript>
|
||
</emphasis>
|
||
411 (
|
||
<figureCitation id="F9EA2A12A151FFE0E97CFDC6FC73FD08" box="[885,957,629,648]" captionStart="Fig" captionStartId="6.[113,139,1976,1990]" captionTargetBox="[145,1468,933,1946]" captionTargetId="figure-602@6.[144,1469,932,1947]" captionTargetPageId="6" captionText="Fig. 3. (A) Ion scan for [M—H] — 621 showing three new metabolites found in (B) the LCMS ion trace. (C) Molecular ions of three new metabolites and (D) fragmentation under high cone voltage showing C-link fragments." figureDoi="http://doi.org/10.5281/zenodo.10485007" httpUri="https://zenodo.org/record/10485007/files/figure.png" pageId="6" pageNumber="79">Fig. 3D</figureCitation>
|
||
) indicating both sugars must be
|
||
<emphasis id="53A5EA85A151FFE0EF1AFDC7FAD1FD08" box="[1299,1311,628,648]" italics="true" pageId="6" pageNumber="79">
|
||
<collectionCode id="07C0AE52A151FFE0EF1AFDC7FAD1FD08" box="[1299,1311,628,648]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="79" type="Herbarium">C</collectionCode>
|
||
</emphasis>
|
||
-linked to the apigenin core (
|
||
<figureCitation id="F9EA2A12A151FFE0E9B3FD22FC3CFD24" box="[954,1010,657,676]" captionStart="Fig" captionStartId="4.[190,216,605,619]" captionTargetBox="[386,1220,181,576]" captionTargetId="figure-248@4.[386,1221,181,576]" captionTargetPageId="4" captionText="Fig. 1. Fragmentation of C-hexosides and C-pentosides under high cone voltage ESIMS conditions to generate fragments losses of 60, 90 and 120 amus." figureDoi="http://doi.org/10.5281/zenodo.10485003" httpUri="https://zenodo.org/record/10485003/files/figure.png" pageId="6" pageNumber="79">Fig. 1</figureCitation>
|
||
). This has previously been shown for
|
||
<emphasis id="53A5EA85A151FFE0EF75FD23FA5AFD23" bold="true" box="[1404,1428,656,675]" pageId="6" pageNumber="79">4a</emphasis>
|
||
where the three new metabolites produced were characterised through the NMR characterisation of natural standards as the di-
|
||
<emphasis id="53A5EA85A151FFE0EF7BFD74FAB0FD5B" box="[1394,1406,711,731]" italics="true" pageId="6" pageNumber="79">
|
||
<collectionCode id="07C0AE52A151FFE0EF7BFD74FAB0FD5B" box="[1394,1406,711,731]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="79" type="Herbarium">C</collectionCode>
|
||
</emphasis>
|
||
-glucosylated compound and two
|
||
<emphasis id="53A5EA85A151FFE0EE48FD50FB83FD77" box="[1089,1101,739,759]" italics="true" pageId="6" pageNumber="79">
|
||
<collectionCode id="07C0AE52A151FFE0EE48FD50FB83FD77" box="[1089,1101,739,759]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="79" type="Herbarium">C</collectionCode>
|
||
</emphasis>
|
||
-galactosylated regioisomers
|
||
<emphasis id="53A5EA85A151FFE0EF7DFD57FA42FD77" bold="true" box="[1396,1420,740,759]" pageId="6" pageNumber="79">7a</emphasis>
|
||
,
|
||
<emphasis id="53A5EA85A151FFE0EF91FD57FA7FFD77" bold="true" box="[1432,1457,740,759]" pageId="6" pageNumber="79">8a</emphasis>
|
||
and
|
||
<emphasis id="53A5EA85A151FFE0E936FCB3FC96FC93" bold="true" box="[831,856,768,787]" pageId="6" pageNumber="79">9a</emphasis>
|
||
(
|
||
<bibRefCitation id="05404B66A151FFE0E96CFCB2FBEDFC93" author="Hooper, A. M. & Caulfield, J. C. & Hao, B. & Pickett, J. A. & Midega, C. A. O. & Khan, Z. R." box="[869,1059,768,788]" pageId="6" pageNumber="79" pagination="380 - 389" refId="ref23639" refString="Hooper, A. M., Caulfield, J. C., Hao, B., Pickett, J. A., Midega, C. A. O., Khan, Z. R., 2015. Isolation and identification of Desmodium root exudates from drought tolerant species used as intercrops against Striga hermonthica. Phytochemistry 117, 380 - 389." type="journal article" year="2015">Hooper et al., 2015</bibRefCitation>
|
||
). The substrates that were not incorporated were
|
||
<emphasis id="53A5EA85A151FFE0E972FCAFFC5DFCAF" bold="true" box="[891,915,796,815]" pageId="6" pageNumber="79">4e</emphasis>
|
||
and
|
||
<emphasis id="53A5EA85A151FFE0E9C4FCAFFC2FFCAF" bold="true" box="[973,993,796,815]" pageId="6" pageNumber="79">4i</emphasis>
|
||
which both possess two oxygen atoms in
|
||
<emphasis id="53A5EA85A151FFE0EFA5FCA8FA13FCAF" box="[1452,1501,795,815]" italics="true" pageId="6" pageNumber="79">meta</emphasis>
|
||
positions. The more sterically bulky substrate
|
||
<emphasis id="53A5EA85A151FFE0EF3AFC8BFA89FCCB" bold="true" box="[1331,1351,824,843]" pageId="6" pageNumber="79">4l</emphasis>
|
||
was also not
|
||
<emphasis id="53A5EA85A151FFE0E936FCE0FC85FCE7" box="[831,843,851,871]" italics="true" pageId="6" pageNumber="79">
|
||
<collectionCode id="07C0AE52A151FFE0E936FCE0FC85FCE7" box="[831,843,851,871]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="79" type="Herbarium">C</collectionCode>
|
||
</emphasis>
|
||
-hexosylated. In the case of
|
||
<emphasis id="53A5EA85A151FFE0EE77FCE0FB44FCE7" box="[1150,1162,851,871]" italics="true" pageId="6" pageNumber="79">
|
||
<collectionCode id="07C0AE52A151FFE0EE77FCE0FB44FCE7" box="[1150,1162,851,871]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="79" type="Herbarium">C</collectionCode>
|
||
</emphasis>
|
||
-arabinosylation, however, there was a distinctly lower tolerance for different B-ring functionality with products only generated from substrates
|
||
<emphasis id="53A5EA85A150FFE1E848FA67FD98FA67" bold="true" box="[577,598,1492,1511]" pageId="7" pageNumber="80">4f</emphasis>
|
||
,
|
||
<emphasis id="53A5EA85A150FFE1E86CFA67FDB1FA67" bold="true" box="[613,639,1492,1511]" pageId="7" pageNumber="80">4h</emphasis>
|
||
and traces from
|
||
<emphasis id="53A5EA85A150FFE1EA9BFA43FF64F983" bold="true" box="[146,170,1520,1539]" pageId="7" pageNumber="80">
|
||
<quantity id="A6299B72A150FFE1EA9BFA43FF64F983" box="[146,170,1520,1539]" metricMagnitude="-3" metricUnit="kg" metricValue="4.0" pageId="7" pageNumber="80" unit="g" value="4.0">4g</quantity>
|
||
</emphasis>
|
||
, all very close in structure to the natural substrate
|
||
<emphasis id="53A5EA85A150FFE1E8DEFA43FD21F983" bold="true" box="[727,751,1520,1539]" pageId="7" pageNumber="80">4a</emphasis>
|
||
. These three substrates were incorporated to yield
|
||
<emphasis id="53A5EA85A150FFE1E874F9BFFD51F99F" bold="true" box="[637,671,1548,1567]" pageId="7" pageNumber="80">10f</emphasis>
|
||
,
|
||
<emphasis id="53A5EA85A150FFE1E8AAF9BFFD61F99F" bold="true" box="[675,687,1548,1567]" pageId="7" pageNumber="80">g</emphasis>
|
||
,
|
||
<emphasis id="53A5EA85A150FFE1E8BCF9BFFD0DF99F" bold="true" box="[693,707,1548,1567]" pageId="7" pageNumber="80">h</emphasis>
|
||
and
|
||
<emphasis id="53A5EA85A150FFE1EA5EF99BFFB7F9BB" bold="true" box="[87,121,1576,1595]" pageId="7" pageNumber="80">11f</emphasis>
|
||
,
|
||
<emphasis id="53A5EA85A150FFE1EA77F99BFF44F9BB" bold="true" box="[126,138,1576,1595]" pageId="7" pageNumber="80">g</emphasis>
|
||
,
|
||
<emphasis id="53A5EA85A150FFE1EA86F99BFF53F9BB" bold="true" box="[143,157,1576,1595]" pageId="7" pageNumber="80">h</emphasis>
|
||
(Supplementary data). Representative data (
|
||
<figureCitation id="F9EA2A12A150FFE1E867F99BFD69F9BB" box="[622,679,1576,1595]" captionStart="Fig" captionStartId="7.[87,113,1369,1383]" captionTargetBox="[118,1441,182,1338]" captionTargetId="figure-422@7.[117,1442,181,1339]" captionTargetPageId="7" captionText="Fig. 4. (A) Ion scan for [M—H] — 591 showing two new metabolites found in (B) the LCMS ion trace. (C) Molecular ions of two new metabolites and (D) fragmentation under high cone voltage showing C-link fragments." figureDoi="http://doi.org/10.5281/zenodo.10485009" httpUri="https://zenodo.org/record/10485009/files/figure.png" pageId="7" pageNumber="80">Fig. 4</figureCitation>
|
||
) reveal two compounds in the ion trace (
|
||
<figureCitation id="F9EA2A12A150FFE1EBDEF9F7FDEAF9D7" box="[471,548,1604,1623]" captionStart="Fig" captionStartId="7.[87,113,1369,1383]" captionTargetBox="[118,1441,182,1338]" captionTargetId="figure-422@7.[117,1442,181,1339]" captionTargetPageId="7" captionText="Fig. 4. (A) Ion scan for [M—H] — 591 showing two new metabolites found in (B) the LCMS ion trace. (C) Molecular ions of two new metabolites and (D) fragmentation under high cone voltage showing C-link fragments." figureDoi="http://doi.org/10.5281/zenodo.10485009" httpUri="https://zenodo.org/record/10485009/files/figure.png" pageId="7" pageNumber="80">Fig. 4B</figureCitation>
|
||
) with ions of 591 (
|
||
<figureCitation id="F9EA2A12A150FFE1EA56F9ECFF63F9F3" box="[95,173,1631,1651]" captionStart="Fig" captionStartId="7.[87,113,1369,1383]" captionTargetBox="[118,1441,182,1338]" captionTargetId="figure-422@7.[117,1442,181,1339]" captionTargetPageId="7" captionText="Fig. 4. (A) Ion scan for [M—H] — 591 showing two new metabolites found in (B) the LCMS ion trace. (C) Molecular ions of two new metabolites and (D) fragmentation under high cone voltage showing C-link fragments." figureDoi="http://doi.org/10.5281/zenodo.10485009" httpUri="https://zenodo.org/record/10485009/files/figure.png" pageId="7" pageNumber="80">Fig. 4A</figureCitation>
|
||
) which are revealed as molecular ions [
|
||
<collectionCode id="07C0AE52A150FFE1E87DF9D3FD45F9F3" box="[628,651,1632,1651]" country="Germany" lsid="urn:lsid:biocol.org:col:15637" name="Botanische Staatssammlung München" pageId="7" pageNumber="80" type="Herbarium">M</collectionCode>
|
||
<emphasis id="53A5EA85A150FFE1E882F9D3FD52F9F3" box="[651,668,1632,1651]" italics="true" pageId="7" pageNumber="80">—</emphasis>
|
||
<collectionCode id="07C0AE52A150FFE1E895F9D3FD61F9F3" box="[668,687,1632,1651]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="7" pageNumber="80" type="Herbarium">H</collectionCode>
|
||
]
|
||
<emphasis id="53A5EA85A150FFE1E8BDF9E8FD0EF9E8" box="[692,704,1627,1640]" italics="true" pageId="7" pageNumber="80">
|
||
<superScript id="96A49BDFA150FFE1E8BDF9E8FD0EF9E8" attach="left" box="[692,704,1627,1640]" fontSize="5" pageId="7" pageNumber="80">—</superScript>
|
||
</emphasis>
|
||
591 (
|
||
<figureCitation id="F9EA2A12A150FFE1EA56F9C8FF66F90E" box="[95,168,1659,1678]" captionStart="Fig" captionStartId="7.[87,113,1369,1383]" captionTargetBox="[118,1441,182,1338]" captionTargetId="figure-422@7.[117,1442,181,1339]" captionTargetPageId="7" captionText="Fig. 4. (A) Ion scan for [M—H] — 591 showing two new metabolites found in (B) the LCMS ion trace. (C) Molecular ions of two new metabolites and (D) fragmentation under high cone voltage showing C-link fragments." figureDoi="http://doi.org/10.5281/zenodo.10485009" httpUri="https://zenodo.org/record/10485009/files/figure.png" pageId="7" pageNumber="80">Fig. 4C</figureCitation>
|
||
) and which fragment to give losses of 60 ([
|
||
<collectionCode id="07C0AE52A150FFE1E877F9C8FD58F90E" box="[638,662,1659,1678]" country="Germany" lsid="urn:lsid:biocol.org:col:15637" name="Botanische Staatssammlung München" pageId="7" pageNumber="80" type="Herbarium">M</collectionCode>
|
||
<emphasis id="53A5EA85A150FFE1E89CF9C8FD68F90E" box="[661,678,1659,1678]" italics="true" pageId="7" pageNumber="80">—</emphasis>
|
||
<collectionCode id="07C0AE52A150FFE1E8AFF9CFFD78F90F" box="[678,694,1660,1679]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="7" pageNumber="80" type="Herbarium">H</collectionCode>
|
||
<emphasis id="53A5EA85A150FFE1E8BEF9C8FD06F90E" box="[695,712,1659,1678]" italics="true" pageId="7" pageNumber="80">—</emphasis>
|
||
60]
|
||
<emphasis id="53A5EA85A150FFE1E8E1F9C4FD3AF904" box="[744,756,1655,1668]" italics="true" pageId="7" pageNumber="80">
|
||
<superScript id="96A49BDFA150FFE1E8E1F9C4FD3AF904" attach="none" box="[744,756,1655,1668]" fontSize="5" pageId="7" pageNumber="80">—</superScript>
|
||
</emphasis>
|
||
531, losses of 90 [
|
||
<collectionCode id="07C0AE52A150FFE1EB6AF92BFEB4F92B" box="[355,378,1688,1707]" country="Germany" lsid="urn:lsid:biocol.org:col:15637" name="Botanische Staatssammlung München" pageId="7" pageNumber="80" type="Herbarium">M</collectionCode>
|
||
<emphasis id="53A5EA85A150FFE1EB73F924FE45F92A" box="[378,395,1687,1706]" italics="true" pageId="7" pageNumber="80">—</emphasis>
|
||
<collectionCode id="07C0AE52A150FFE1EB82F92BFE55F92B" box="[395,411,1688,1707]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="7" pageNumber="80" type="Herbarium">H</collectionCode>
|
||
<emphasis id="53A5EA85A150FFE1EB92F924FE62F92A" box="[411,428,1687,1706]" italics="true" pageId="7" pageNumber="80">—</emphasis>
|
||
90]
|
||
<emphasis id="53A5EA85A150FFE1EBC4F920FE17F920" box="[461,473,1683,1696]" italics="true" pageId="7" pageNumber="80">
|
||
<superScript id="96A49BDFA150FFE1EBC4F920FE17F920" attach="left" box="[461,473,1683,1696]" fontSize="5" pageId="7" pageNumber="80">—</superScript>
|
||
</emphasis>
|
||
501}, losses of 120 ([
|
||
<collectionCode id="07C0AE52A150FFE1EA6DF900FFB2F946" box="[100,124,1715,1734]" country="Germany" lsid="urn:lsid:biocol.org:col:15637" name="Botanische Staatssammlung München" pageId="7" pageNumber="80" type="Herbarium">M</collectionCode>
|
||
<emphasis id="53A5EA85A150FFE1EA75F900FF43F946" box="[124,141,1715,1734]" italics="true" pageId="7" pageNumber="80">—</emphasis>
|
||
<collectionCode id="07C0AE52A150FFE1EA84F907FF53F947" box="[141,157,1716,1735]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="7" pageNumber="80" type="Herbarium">H</collectionCode>
|
||
<emphasis id="53A5EA85A150FFE1EA94F900FF60F946" box="[157,174,1715,1734]" italics="true" pageId="7" pageNumber="80">—</emphasis>
|
||
120]
|
||
<emphasis id="53A5EA85A150FFE1EAD5F91CFF26F93C" box="[220,232,1711,1724]" italics="true" pageId="7" pageNumber="80">
|
||
<superScript id="96A49BDFA150FFE1EAD5F91CFF26F93C" attach="left" box="[220,232,1711,1724]" fontSize="5" pageId="7" pageNumber="80">—</superScript>
|
||
</emphasis>
|
||
471 and combinations of losses ([
|
||
<collectionCode id="07C0AE52A150FFE1E855F900FDBAF946" box="[604,628,1715,1734]" country="Germany" lsid="urn:lsid:biocol.org:col:15637" name="Botanische Staatssammlung München" pageId="7" pageNumber="80" type="Herbarium">M</collectionCode>
|
||
<emphasis id="53A5EA85A150FFE1E87AF900FD4AF946" box="[627,644,1715,1734]" italics="true" pageId="7" pageNumber="80">—</emphasis>
|
||
<collectionCode id="07C0AE52A150FFE1E88DF907FD5AF947" box="[644,660,1716,1735]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="7" pageNumber="80" type="Herbarium">H</collectionCode>
|
||
<emphasis id="53A5EA85A150FFE1E89CF900FD68F946" box="[661,678,1715,1734]" italics="true" pageId="7" pageNumber="80">—</emphasis>
|
||
60-90]
|
||
<emphasis id="53A5EA85A150FFE1E8E1F91CFD3AF93C" box="[744,756,1711,1724]" italics="true" pageId="7" pageNumber="80">
|
||
<superScript id="96A49BDFA150FFE1E8E1F91CFD3AF93C" attach="none" box="[744,756,1711,1724]" fontSize="5" pageId="7" pageNumber="80">—</superScript>
|
||
</emphasis>
|
||
441, [
|
||
<collectionCode id="07C0AE52A150FFE1EA87F963FF6BF963" box="[142,165,1744,1763]" country="Germany" lsid="urn:lsid:biocol.org:col:15637" name="Botanische Staatssammlung München" pageId="7" pageNumber="80" type="Herbarium">M</collectionCode>
|
||
<emphasis id="53A5EA85A150FFE1EAADF97CFF7BF962" box="[164,181,1743,1762]" italics="true" pageId="7" pageNumber="80">—</emphasis>
|
||
<collectionCode id="07C0AE52A150FFE1EABCF963FF0BF963" box="[181,197,1744,1763]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="7" pageNumber="80" type="Herbarium">H</collectionCode>
|
||
<emphasis id="53A5EA85A150FFE1EACCF97CFF18F962" box="[197,214,1743,1762]" italics="true" pageId="7" pageNumber="80">—</emphasis>
|
||
60-120]
|
||
<emphasis id="53A5EA85A150FFE1EB2FF979FEFCF957" box="[294,306,1738,1751]" italics="true" pageId="7" pageNumber="80">
|
||
<superScript id="96A49BDFA150FFE1EB2FF979FEFCF957" attach="left" box="[294,306,1738,1751]" fontSize="5" pageId="7" pageNumber="80">—</superScript>
|
||
</emphasis>
|
||
411 and [
|
||
<collectionCode id="07C0AE52A150FFE1EB9DF963FE65F963" box="[404,427,1744,1763]" country="Germany" lsid="urn:lsid:biocol.org:col:15637" name="Botanische Staatssammlung München" pageId="7" pageNumber="80" type="Herbarium">M</collectionCode>
|
||
<emphasis id="53A5EA85A150FFE1EBA2F97CFE72F962" box="[427,444,1743,1762]" italics="true" pageId="7" pageNumber="80">—</emphasis>
|
||
<collectionCode id="07C0AE52A150FFE1EBB5F963FE02F963" box="[444,460,1744,1763]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="7" pageNumber="80" type="Herbarium">H</collectionCode>
|
||
<emphasis id="53A5EA85A150FFE1EBC5F97CFE13F962" box="[460,477,1743,1762]" italics="true" pageId="7" pageNumber="80">—</emphasis>
|
||
90-120]
|
||
<emphasis id="53A5EA85A150FFE1E824F979FDF7F957" box="[557,569,1738,1751]" italics="true" pageId="7" pageNumber="80">
|
||
<superScript id="96A49BDFA150FFE1E824F979FDF7F957" attach="left" box="[557,569,1738,1751]" fontSize="5" pageId="7" pageNumber="80">—</superScript>
|
||
</emphasis>
|
||
381 (
|
||
<figureCitation id="F9EA2A12A150FFE1E87BF97CFD76F962" box="[626,696,1743,1762]" captionStart="Fig" captionStartId="7.[87,113,1369,1383]" captionTargetBox="[118,1441,182,1338]" captionTargetId="figure-422@7.[117,1442,181,1339]" captionTargetPageId="7" captionText="Fig. 4. (A) Ion scan for [M—H] — 591 showing two new metabolites found in (B) the LCMS ion trace. (C) Molecular ions of two new metabolites and (D) fragmentation under high cone voltage showing C-link fragments." figureDoi="http://doi.org/10.5281/zenodo.10485009" httpUri="https://zenodo.org/record/10485009/files/figure.png" pageId="7" pageNumber="80">Fig. 4D</figureCitation>
|
||
) indicating both sugars must be
|
||
<emphasis id="53A5EA85A150FFE1EB7BF959FEB0F97E" box="[370,382,1770,1790]" italics="true" pageId="7" pageNumber="80">
|
||
<collectionCode id="07C0AE52A150FFE1EB7BF959FEB0F97E" box="[370,382,1770,1790]" country="Denmark" name="University of Copenhagen" pageId="7" pageNumber="80" type="Herbarium">C</collectionCode>
|
||
</emphasis>
|
||
-linked to the apigenin core (
|
||
<figureCitation id="F9EA2A12A150FFE1E8A0F958FD11F97E" box="[681,735,1771,1790]" captionStart="Fig" captionStartId="4.[190,216,605,619]" captionTargetBox="[386,1220,181,576]" captionTargetId="figure-248@4.[386,1221,181,576]" captionTargetPageId="4" captionText="Fig. 1. Fragmentation of C-hexosides and C-pentosides under high cone voltage ESIMS conditions to generate fragments losses of 60, 90 and 120 amus." figureDoi="http://doi.org/10.5281/zenodo.10485003" httpUri="https://zenodo.org/record/10485003/files/figure.png" pageId="7" pageNumber="80">Fig. 1</figureCitation>
|
||
).
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |