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<document id="B01B27B710B63989FC3854D45097CC1C" ID-DOI="10.1016/j.phytochem.2014.10.022" ID-ISSN="1873-3700" ID-Zenodo-Dep="10488103" IM.bibliography_approvedBy="diego" IM.illustrations_approvedBy="diego" IM.materialsCitations_approvedBy="diego" IM.metadata_approvedBy="felipe" IM.tables_approvedBy="diego" IM.taxonomicNames_approvedBy="diego" IM.treatments_approvedBy="diego" checkinTime="1704954536271" checkinUser="felipe" docAuthor="Mihajlovic, Luka, Radosavljevic, Jelena, Burazer, Lidija, Smiljanic, Katarina &amp; Velickovic, Tanja Cirkovic" docDate="2015" docId="304587B90E6842069A35FD52FF18F907" docLanguage="en" docName="Phytochemistry.109.125-132.pdf" docOrigin="Phytochemistry 109" docSource="http://dx.doi.org/10.1016/j.phytochem.2014.10.022" docStyle="DocumentStyle:9E596C34F4E94307D29315B03ACE1007.6:Phytochemistry.2014-2019.journal_article" docStyleId="9E596C34F4E94307D29315B03ACE1007" docStyleName="Phytochemistry.2014-2019.journal_article" docStyleVersion="6" docTitle="Ambrosia artemisiifolia L." docType="treatment" docVersion="1" lastPageNumber="129" masterDocId="CC7CFFC10E6942029A62FFE0FFF6FFAC" masterDocTitle="Composition of polyphenol and polyamide compounds in common ragweed (Ambrosia artemisiifolia L.) pollen and sub-pollen particles" masterLastPageNumber="132" masterPageNumber="125" pageNumber="126" updateTime="1705496864739" updateUser="diego">
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<mods:title id="FE4DB9B171E9F2DBEBDC9A161C84E5D0">Composition of polyphenol and polyamide compounds in common ragweed (Ambrosia artemisiifolia L.) pollen and sub-pollen particles</mods:title>
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<mods:namePart id="3981AC5D9C2584EF184777AF8B6236DB">Mihajlovic, Luka</mods:namePart>
<mods:affiliation id="57883CD79B5ED8CAA2CC32CB1C6C19EE">Center of Excellence in Molecular Food Sciences, University of Belgrade - Faculty of Chemistry, Belgrade, Serbia</mods:affiliation>
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<mods:namePart id="823F5DDDE858C97F32D9388E932BDB70">Radosavljevic, Jelena</mods:namePart>
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<mods:namePart id="AF0D7062AD0D49930494CC0730F27B20">Burazer, Lidija</mods:namePart>
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<mods:namePart id="219EFBDB42C1FB29BE174389A09302F0">Smiljanic, Katarina</mods:namePart>
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<emphasis id="8A98EABD0E6842039A35FD52FD33FD6A" box="[87,709,690,710]" italics="true" pageId="1" pageNumber="126">2.1. Phenolics and flavonoid concentration in the pollen and SPP</emphasis>
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extracts of 
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A. artemisiifolia 
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<paragraph id="B85336AF0E6842039A14FCE6FD8AFC55" blockId="1.[87,757,774,1100]" pageId="1" pageNumber="126">
Separation scheme for extraction of phenolic compounds is given in 
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. It was determined that the ethanol-based extract of 
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<emphasis id="8A98EABD0E6842039ADCFCDDFEA3FCFD" box="[190,341,829,849]" italics="true" pageId="1" pageNumber="126">A. artemisiifolia</emphasis>
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. pollen contains phenolics at a concentration of 6.79 ± 
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GAE/g pollen, while its SPP value is 4.56 ± 
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GAE/g SPP, being 33% significantly lower from the whole pollen grain extract. In addition, flavonoid content in these extracts mounted up to 98% (4.45 ± 
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/g) of total phenolics in SPP and 70% for whole pollen extract (4.71 ± 
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/g). This is in accordance with structural data (
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and 
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).
</paragraph>
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Water-soluble phenolics are present at 4.51 ± 
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GAE/g pollen. This value of phenolics in 
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<emphasis id="8A98EABD0E6842039BC5FBFCFDCBFB9C" box="[423,573,1052,1072]" italics="true" pageId="1" pageNumber="126">A. artemisiifolia</emphasis>
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. pollen is significantly lower than the value previously reported for the phenolic content of 
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<emphasis id="8A98EABD0E68420399F7FF55FBDBFF65" box="[917,1069,181,201]" italics="true" pageId="1" pageNumber="126">A. artemisiifolia</emphasis>
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. herb, which can go as high as 4.35% of total dry weight (
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/g dry herb) (
<bibRefCitation id="DC7D4B5E0E6842039EAEFF32FA72FF49" author="Maksimovic, Z." box="[1228,1412,210,229]" pageId="1" pageNumber="126" pagination="356 - 360" refId="ref7235" refString="Maksimovic, Z., 2008. In vitro antioxidant activity of ragweed (Ambrosia artemisiifolia L., Asteraceae) herb. Ind. Crops Prod. 28, 356 - 360." type="journal article" year="2008">Maksimovic, 2008</bibRefCitation>
). This can be due to the different roles phenolics might play in pollen 
<emphasis id="8A98EABD0E6842039947FEE9FCC9FEB1" box="[805,831,265,285]" italics="true" pageId="1" pageNumber="126">vs.</emphasis>
plant leaves and stalks (
<bibRefCitation id="DC7D4B5E0E6842039E2BFEEAFAE6FEB1" author="Falasca, G. &amp; Franceschetti, M. &amp; Bagni, N. &amp; Altamura, M. M. &amp; Biasi, R." box="[1097,1296,266,285]" pageId="1" pageNumber="126" pagination="565 - 573" refId="ref6439" refString="Falasca, G., Franceschetti, M., Bagni, N., Altamura, M. M., Biasi, R., 2010. Polyamine biosynthesis and control of the development of functional pollen in kiwifruit. Plant Physiol. Biochem. 48, 565 - 573." type="journal article" year="2010">Falasca et al., 2010</bibRefCitation>
). The amount of flavonoids obtained from the aqueous pollen extract is 3.95 ± 
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/g pollen, which is 87.5% of total soluble phenolic content. It can be concluded that the flavonoids are the main components of pollen and SPP phenolic extracts, as opposed to dry plant flowering summits, where they make up less than 5% of total phenolics content (
<bibRefCitation id="DC7D4B5E0E6842039986FE51FB6CFE68" author="Maksimovic, Z." box="[996,1178,433,452]" pageId="1" pageNumber="126" pagination="356 - 360" refId="ref7235" refString="Maksimovic, Z., 2008. In vitro antioxidant activity of ragweed (Ambrosia artemisiifolia L., Asteraceae) herb. Ind. Crops Prod. 28, 356 - 360." type="journal article" year="2008">Maksimovic, 2008</bibRefCitation>
). In addition, values obtained for water- and ethanol extracts in 
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<emphasis id="8A98EABD0E6842039E1FFE2CFAE5FE4C" box="[1149,1299,460,480]" italics="true" pageId="1" pageNumber="126">A. artemisiifolia</emphasis>
</taxonomicName>
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. pollen are also lower than majority of bee pollen (flowering) species, while results on sub-pollen particle phenolics amount are novel and thus incomparable to literature data. However it is noticeable that SPP have one-third lower content of the total phenolics than the whole pollen grains, which could be important when concerned with allergy modulating properties of polyphenols. It is known that beside direct anti-allergic effect (
<bibRefCitation id="DC7D4B5E0E6842039E30FD71FAE9FD08" author="Yoon, M. S. &amp; Lee, J. S. &amp; Choi, B. M. &amp; Jeong, Y. I. &amp; Lee, C. M. &amp; Park, J. H. &amp; Moon, Y. &amp; Sung, S. C. &amp; Lee, S. K. &amp; Chang, Y. H. &amp; Chung, H. Y. &amp; Park, Y. M." box="[1106,1311,657,676]" pageId="1" pageNumber="126" pagination="1033 - 1044" refId="ref8031" refString="Yoon, M. S., Lee, J. S., Choi, B. M., Jeong, Y. I., Lee, C. M., Park, J. H., Moon, Y., Sung, S. C., Lee, S. K., Chang, Y. H., Chung, H. Y., Park, Y. M., 2006. Apigenin inhibits immunostimulatory function of dendritic cells: implication of immunotherapeutic adjuvant. Mol. Pharmacol. 70, 1033 - 1044." type="journal article" year="2006">Yoon et al., 2006</bibRefCitation>
), polyphenolic compounds could alleviate allergy by cross-linking with allergens and thus reducing their allergenicity (
<bibRefCitation id="DC7D4B5E0E6842039EC5FD28FA8AFD77" author="Tantoush, Z. &amp; Stanic, D. &amp; Stojadinovic, M. &amp; Ognjenovic, J. &amp; Mihajlovic, L. &amp; AtanaskovicMarkovic, M. &amp; Cirkovic Velickovic, T." box="[1191,1404,712,732]" pageId="1" pageNumber="126" pagination="84 - 91" refId="ref7833" refString="Tantoush, Z., Stanic, D., Stojadinovic, M., Ognjenovic, J., Mihajlovic, L., AtanaskovicMarkovic, M., Cirkovic Velickovic, T., 2011. Digestibility and allergenicity of β- lactoglobulin following laccase-mediated cross-linking in the presence of sour cherry phenolics. Food Chem. 125, 84 - 91." type="journal article" year="2011">Tantoush et al., 2011</bibRefCitation>
).
</paragraph>
<paragraph id="B85336AF0E6842039947FCEDFAA5FC8D" blockId="1.[805,1363,781,801]" box="[805,1363,781,801]" pageId="1" pageNumber="126">
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<emphasis id="8A98EABD0E6842039947FCEDFAA5FC8D" box="[805,1363,781,801]" italics="true" pageId="1" pageNumber="126">2.2. Antioxidative properties of the pollen and SPP extract</emphasis>
</heading>
</paragraph>
<paragraph id="B85336AF0E6842039926FCA6FB6FFBF8" blockId="1.[805,1475,838,1415]" pageId="1" pageNumber="126">
DPPH assay is commonly used to assess free radical scavenging of a compound or a mixture. 
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pollen extract showed 73 ± 2% free radical scavenging, as compared to a methanol blank. This value is equivalent to the scavenging activity of 28.4 µM butylated hydroxyl toluene (BHT) standard. SPP extract exhibited lower activity, with 56 ± 2% of free radical scavenging activity (23% decrease). The differences are statistically significant (
<emphasis id="8A98EABD0E684203994FFBE8FCCFFBB0" box="[813,825,1032,1052]" italics="true" pageId="1" pageNumber="126">p</emphasis>
&lt;0.001) (
<figureCitation id="20D72A2A0E68420399FDFBE9FC1FFBB0" box="[927,1001,1033,1052]" captionStart="Fig" captionStartId="2.[113,139,1728,1742]" captionTargetBox="[348,1260,1335,1698]" captionTargetId="figure-739@2.[348,1260,1334,1698]" captionTargetPageId="2" captionText="Fig. 2. (A) Relative free radical scavenging activity of A. artemisiifolia L. pollen and sub-pollen particles (SPP) aqueous extracts according to DPPH assay (p &lt;0.001). (B) Antioxidative activity of A. artemisiifolia L. pollen and sub-pollen particles (SPP) aqueous extracts according to ABTS+ assay (p &lt;0.001). ABTS assay showed similar results to the DPPH assay, with SPP extract exhibiting significantly diminished activity." figureDoi="http://doi.org/10.5281/zenodo.10488107" httpUri="https://zenodo.org/record/10488107/files/figure.png" pageId="1" pageNumber="126">Fig. 2A</figureCitation>
). Both values can be considered as significant free radical scavenging activity and are corroborated by papers by other authors (
<bibRefCitation id="DC7D4B5E0E68420399BFFBA1FB7AFBF8" author="Negri, G. &amp; Teixeira, E. W. &amp; Alves, M. L. &amp; Moreti, A. C. &amp; Otsuk, I. P. &amp; Borguini, R. G. &amp; Salatino, A." box="[989,1164,1089,1108]" pageId="1" pageNumber="126" pagination="5516 - 5522" refId="ref7384" refString="Negri, G., Teixeira, E. W., Alves, M. L., Moreti, A. C., Otsuk, I. P., Borguini, R. G., Salatino, A., 2011. Hydroxycinnamic acid amide derivatives, phenolic compounds and antioxidant activities of extracts of pollen samples from Southeast Brazil. J. Agric. Food Chem. 59, 5516 - 5522." type="journal article" year="2011">Negri et al., 2011</bibRefCitation>
).
</paragraph>
<paragraph id="B85336AF0E6842039926FBBDFBEEFA2B" blockId="1.[805,1475,838,1415]" pageId="1" pageNumber="126">
ABTS+ assay was used to measure the antioxidative ability of the extracts. 
<taxonomicName id="7FEC4D2C0E68420399CEFB99FBFAFB20" box="[940,1036,1145,1164]" class="Magnoliopsida" family="Asteraceae" genus="Ambrosia" kingdom="Plantae" order="Asterales" pageId="1" pageNumber="126" phylum="Tracheophyta" rank="genus">Ambrosia</taxonomicName>
pollen extract showed activity equivalent to 5.9 + 0.2 µM quercetin, while the activity of SPP extract was significantly lower (
<emphasis id="8A98EABD0E68420399B9FB4FFC11FB6F" box="[987,999,1199,1219]" italics="true" pageId="1" pageNumber="126">p</emphasis>
&lt;0.001) at 4.1 + 0.1 µM quercetin equivalent (31% decrease). The results are shown in 
<figureCitation id="20D72A2A0E6842039EB3FB2CFAEEFB4C" box="[1233,1304,1228,1248]" captionStart="Fig" captionStartId="2.[113,139,1728,1742]" captionTargetBox="[348,1260,1335,1698]" captionTargetId="figure-739@2.[348,1260,1334,1698]" captionTargetPageId="2" captionText="Fig. 2. (A) Relative free radical scavenging activity of A. artemisiifolia L. pollen and sub-pollen particles (SPP) aqueous extracts according to DPPH assay (p &lt;0.001). (B) Antioxidative activity of A. artemisiifolia L. pollen and sub-pollen particles (SPP) aqueous extracts according to ABTS+ assay (p &lt;0.001). ABTS assay showed similar results to the DPPH assay, with SPP extract exhibiting significantly diminished activity." figureDoi="http://doi.org/10.5281/zenodo.10488107" httpUri="https://zenodo.org/record/10488107/files/figure.png" pageId="1" pageNumber="126">Fig. 2B</figureCitation>
. Both values are lower than expected from the previously obtained values of pollen phenolics concentration. Although quercetin was used as a standard due to its structural similarity to main components of the mixture, most of the phenolics present in the extract are glycosylated or otherwise modified, which can affect the antioxidative capacity of the mixture.
</paragraph>
<paragraph id="B85336AF0E6842039947FA58FBB6FA44" blockId="1.[805,1415,1464,1512]" pageId="1" pageNumber="126">
<emphasis id="8A98EABD0E6842039947FA58FBB6FA44" italics="true" pageId="1" pageNumber="126">
2.3. Characterization of 
<taxonomicName id="7FEC4D2C0E6842039E6EFA58FB52FA60" box="[1036,1188,1464,1484]" class="Magnoliopsida" family="Asteraceae" genus="Ambrosia" kingdom="Plantae" order="Asterales" pageId="1" pageNumber="126" phylum="Tracheophyta" rank="species" species="artemisiifolia">A. artemisiifolia</taxonomicName>
<collectionCode id="DEFDAE6A0E6842039EC9FA58FB41FA60" box="[1195,1207,1464,1484]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="1" pageNumber="126" type="Herbarium">L</collectionCode>
. pollen water-soluble 
<heading id="E31B81C30E6842039947FA34FBB6FA44" box="[805,1088,1492,1512]" fontSize="8" level="3" pageId="1" pageNumber="126" reason="8">phenolics on Orbitrap LTQ XL</heading>
</emphasis>
</paragraph>
<paragraph id="B85336AF0E6842039926F9EDFAF5F948" blockId="1.[805,1475,1548,2015]" pageId="1" pageNumber="126">
An Orbitrap analysis showed that 
<taxonomicName id="7FEC4D2C0E6842039EDEF9ECFAAFF98C" box="[1212,1369,1548,1568]" class="Magnoliopsida" family="Asteraceae" genus="Ambrosia" kingdom="Plantae" order="Asterales" pageId="1" pageNumber="126" phylum="Tracheophyta" rank="species" species="artemisiifolia">
<emphasis id="8A98EABD0E6842039EDEF9ECFAAFF98C" box="[1212,1369,1548,1568]" italics="true" pageId="1" pageNumber="126">A. artemisiifolia</emphasis>
</taxonomicName>
<collectionCode id="DEFDAE6A0E6842039F04F9EEFA82F98D" box="[1382,1396,1550,1569]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="1" pageNumber="126" type="Herbarium">L</collectionCode>
. pollen phenolics have a complex and diverse composition, including phenolic derivates of polyamide spermidine, which we were unable to detect with the triple quadrupole detector (data not shown). All of the phenolic glycosides detected with high resolution and sensitive 
<collectionCode id="DEFDAE6A0E6842039947F979FC9BF900" box="[805,877,1689,1708]" pageId="1" pageNumber="126">UHPLC</collectionCode>
/ESI-LTQ-MS– 
<collectionCode id="DEFDAE6A0E6842039994F979FBE2F900" box="[1014,1044,1689,1708]" country="Italy" lsid="urn:lsid:biocol.org:col:14396" name="Herbarium Messanaensis, Università di Messina" pageId="1" pageNumber="126" type="Herbarium">MS</collectionCode>
Orbitrap, including 
<emphasis id="8A98EABD0E6842039E89F978FAF9F900" box="[1259,1295,1688,1708]" italics="true" pageId="1" pageNumber="126">m/z</emphasis>
higher than 570 (di- and tri-glycosides of isorhamnetin), are shown 
<tableCitation id="F56E03140E6842039F24F954FA65F964" box="[1350,1427,1716,1736]" captionStart="Table 1" captionStartId="2.[114,158,183,197]" captionTargetPageId="2" captionText="Table 1 Compounds detected in A. artemisiifolia L. pollen aqueous extract on the UHPLC/ESI-LTQ Orbitrap mass spectrometer." pageId="1" pageNumber="126">Table 1</tableCitation>
and its base peak chromatogram is shown in 
<figureCitation id="20D72A2A0E6842039EA5F930FB08F948" box="[1223,1278,1744,1764]" captionStart="Fig" captionStartId="3.[219,245,1003,1017]" captionTargetBox="[216,1347,185,974]" captionTargetId="figure-468@3.[216,1348,181,974]" captionTargetPageId="3" captionText="Fig. 3. Base peak chromatogram of the A. artemisiifolia L. aqueous pollen extract analysed on UHPLC/ESI-LTQ-Orbitrap mass spectrometer." figureDoi="http://doi.org/10.5281/zenodo.10488109" httpUri="https://zenodo.org/record/10488109/files/figure.png" pageId="1" pageNumber="126">Fig. 3</figureCitation>
.
</paragraph>
<paragraph id="B85336AF0E6842039926F90CFC22F8C3" blockId="1.[805,1475,1548,2015]" pageId="1" pageNumber="126">
All detected glycosides are derivatives of three main flavonols: quercetin, 
<emphasis id="8A98EABD0E68420399F9F8E7FC5CF8B7" box="[923,938,1799,1819]" italics="true" pageId="1" pageNumber="126">
<collectionCode id="DEFDAE6A0E68420399F9F8E7FC5CF8B7" box="[923,938,1799,1819]" country="Norway" lsid="urn:lsid:biocol.org:col:13093" name="Botanical Museum - University of Oslo" pageId="1" pageNumber="126" type="Herbarium">O</collectionCode>
</emphasis>
-methylquercetin (isorhamnetin), and kaempferol (
<figureCitation id="20D72A2A0E684203994FF8C4FC90F89B" box="[813,870,1828,1847]" captionStart="Fig" captionStartId="3.[257,283,1338,1352]" captionTargetBox="[216,1348,1077,1309]" captionTargetId="figure-490@3.[216,1349,1077,1309]" captionTargetPageId="3" captionText="Fig. 4. Main aglycones detected in the A. artemisiifolia L. aqueous pollen extract. (A) quercetin, (B) kaempferol, (C) isorhamnetin." figureDoi="http://doi.org/10.5281/zenodo.10488111" httpUri="https://zenodo.org/record/10488111/files/figure.png" pageId="1" pageNumber="126">Fig. 4</figureCitation>
). For each aglycone, a series of peaks (satellite sets) was observed, representing unsubstituted and malonylated hexosides and hexuronides.
</paragraph>
<paragraph id="B85336AF0E6842039926F898FC3CF873" blockId="1.[805,1475,1548,2015]" pageId="1" pageNumber="126">
Fragment analysis allowed identification of [Y 
<subScript id="246834EA0E6842039F76F861FAEBF821" attach="left" box="[1300,1309,1921,1933]" fontSize="5" pageId="1" pageNumber="126">0</subScript>
<emphasis id="8A98EABD0E6842039F7FF897FAD8F827" box="[1309,1326,1911,1931]" italics="true" pageId="1" pageNumber="126">—</emphasis>
2 
<collectionCode id="DEFDAE6A0E6842039F5BF898FABDF827" box="[1337,1355,1912,1931]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="1" pageNumber="126" type="Herbarium">H</collectionCode>
<emphasis id="8A98EABD0E6842039F29F897FAAAF827" box="[1355,1372,1911,1931]" italics="true" pageId="1" pageNumber="126">—</emphasis>
CO] 
<emphasis id="8A98EABD0E6842039FE2F893FA7AF82C" box="[1408,1420,1907,1920]" italics="true" pageId="1" pageNumber="126">
<superScript id="4F999BE70E6842039FE2F893FA7AF82C" attach="left" box="[1408,1420,1907,1920]" fontSize="5" pageId="1" pageNumber="126">—</superScript>
</emphasis>
ions, a characteristic ion-peak of 3-O-monoglucosides, confirming the structures proposed with preliminary results (
<bibRefCitation id="DC7D4B5E0E6842039F26F850FC4AF873" author="Vukics, V. &amp; Guttman, A." pageId="1" pageNumber="126" pagination="1 - 16" refId="ref7897" refString="Vukics, V., Guttman, A., 2010. Structural characterization of flavonoid glycosides by multi-stage mass spectrometry. Mass Spectrom. Rev. 29, 1 - 16." type="journal article" year="2010">Vukics and Guttman, 2010</bibRefCitation>
).
</paragraph>
<caption id="EC9366270E6842039A35F858FE3AF871" ID-DOI="http://doi.org/10.5281/zenodo.10488105" ID-Zenodo-Dep="10488105" httpUri="https://zenodo.org/record/10488105/files/figure.png" pageId="1" pageNumber="126" startId="1.[87,113,1976,1990]" targetBox="[101,742,1135,1947]" targetPageId="1" targetType="figure">
<paragraph id="B85336AF0E6842039A35F858FE3AF871" blockId="1.[87,757,1975,2013]" pageId="1" pageNumber="126">
<emphasis id="8A98EABD0E6842039A35F858FF7DF86A" bold="true" box="[87,139,1976,1990]" pageId="1" pageNumber="126">Fig. 1.</emphasis>
Schematic representation of aqueous phenolic extraction from 
<taxonomicName id="7FEC4D2C0E68420398FCF857FF74F871" class="Magnoliopsida" family="Asteraceae" genus="Ambrosia" kingdom="Plantae" order="Asterales" pageId="1" pageNumber="126" phylum="Tracheophyta" rank="species" species="artemisiifolia">
<emphasis id="8A98EABD0E68420398FCF857FF74F871" italics="true" pageId="1" pageNumber="126">A. artemisiifolia</emphasis>
</taxonomicName>
L. pollen and sub-pollen particles (SPP).
</paragraph>
</caption>
<caption id="EC9366270E6B42009A10FF57FBE0FF70" pageId="2" pageNumber="127" startId="2.[114,158,183,197]" targetBox="[136,1477,243,797]" targetIsTable="true" targetPageId="2" targetType="table">
<paragraph id="B85336AF0E6B42009A10FF57FF58FF69" blockId="2.[113,1046,183,220]" box="[114,174,183,197]" pageId="2" pageNumber="127">
<emphasis id="8A98EABD0E6B42009A10FF57FF58FF69" bold="true" box="[114,174,183,197]" pageId="2" pageNumber="127">Table 1</emphasis>
</paragraph>
<paragraph id="B85336AF0E6B42009A13FF2EFBE0FF70" blockId="2.[113,1046,183,220]" box="[113,1046,205,220]" pageId="2" pageNumber="127">
Compounds detected in 
<taxonomicName id="7FEC4D2C0E6B42009B51FF2DFE5CFF70" box="[307,426,205,220]" class="Magnoliopsida" family="Asteraceae" genus="Ambrosia" kingdom="Plantae" order="Asterales" pageId="2" pageNumber="127" phylum="Tracheophyta" rank="species" species="artemisiifolia">
<emphasis id="8A98EABD0E6B42009B51FF2DFE5CFF70" box="[307,426,205,220]" italics="true" pageId="2" pageNumber="127">A. artemisiifolia</emphasis>
</taxonomicName>
L. pollen aqueous extract on the UHPLC/ESI-LTQ Orbitrap mass spectrometer.
</paragraph>
</caption>
<paragraph id="B85336AF0E6B42009AEAFF14FADDFCBD" pageId="2" pageNumber="127">
<table id="CAECC40F0E6BBDFD9AEAFF13FA33FCB1" box="[136,1477,243,797]" gridcols="7" gridrows="24" pageId="2" pageNumber="127">
<tr id="06DC34ED0E6BBDFD9AEAFF13FA33FEAE" box="[136,1477,243,258]" gridrow="0" pageId="2" pageNumber="127" rowspan-4="1">
<th id="450D5D910E6BBDFD9AEAFF13FEC2FEAE" box="[136,308,243,258]" gridcol="0" gridrow="0" pageId="2" pageNumber="127">Retention time (min)</th>
<th id="450D5D910E6BBDFD9B1AFF13FE1CFEAE" box="[376,490,243,258]" gridcol="1" gridrow="0" pageId="2" pageNumber="127">
Measured 
<emphasis id="8A98EABD0E6B42009BAFFF13FE2AFEAE" box="[461,476,243,258]" italics="true" pageId="2" pageNumber="127">m</emphasis>
/ 
<emphasis id="8A98EABD0E6B42009B80FF13FE1CFEAE" box="[482,490,243,258]" italics="true" pageId="2" pageNumber="127">z</emphasis>
</th>
<th id="450D5D910E6BBDFD984DFF13FCFFFEAE" box="[559,777,243,258]" colspan="2" colspanRight="1" gridcol="2" gridrow="0" pageId="2" pageNumber="127">
Diagnostic fragments (
<emphasis id="8A98EABD0E6B42009885FF13FCF5FEAE" box="[743,771,243,258]" italics="true" pageId="2" pageNumber="127">m/z</emphasis>
)
</th>
<th id="450D5D910E6BBDFD99C8FF13FBB6FEAE" box="[938,1088,243,258]" gridcol="5" gridrow="0" pageId="2" pageNumber="127">Molecular formula</th>
<th id="450D5D910E6BBDFD9EE7FF13FA33FEAE" box="[1157,1477,243,258]" gridcol="6" gridrow="0" pageId="2" pageNumber="127">Compound name</th>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFEF2FA33FE8A" box="[136,1477,274,294]" gridrow="1" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFEF2FEC2FE8A" box="[136,308,274,294]" gridcol="0" gridrow="1" pageId="2" pageNumber="127">0.38</th>
<td id="450D5D910E6BBDFD9B1AFEF2FE1CFE8A" box="[376,490,274,294]" gridcol="1" gridrow="1" pageId="2" pageNumber="127">179.06</td>
<td id="450D5D910E6BBDFD984DFEF2FD90FE8A" box="[559,614,274,294]" gridcol="2" gridrow="1" pageId="2" pageNumber="127">161.02</td>
<td id="450D5D910E6BBDFD98CFFEF2FCFFFE8A" box="[685,777,274,294]" gridcol="3" gridrow="1" pageId="2" pageNumber="127">131.30</td>
<td id="450D5D910E6BBDFD9949FEF2FC95FE8A" box="[811,867,274,294]" gridcol="4" gridrow="1" pageId="2" pageNumber="127">115.13</td>
<td id="450D5D910E6BBDFD99C8FEF2FBB6FE8A" box="[938,1088,274,294]" gridcol="5" gridrow="1" pageId="2" pageNumber="127">C9H8O4</td>
<td id="450D5D910E6BBDFD9EE7FEF2FA33FE8A" box="[1157,1477,274,294]" gridcol="6" gridrow="1" pageId="2" pageNumber="127">Caffeic acid a</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFEC9FA33FE91" box="[136,1477,297,317]" gridrow="2" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFEC9FEC2FE91" box="[136,308,297,317]" gridcol="0" gridrow="2" pageId="2" pageNumber="127">0.49</th>
<td id="450D5D910E6BBDFD9B1AFEC9FE1CFE91" box="[376,490,297,317]" gridcol="1" gridrow="2" pageId="2" pageNumber="127">191.02</td>
<td id="450D5D910E6BBDFD984DFEC9FD90FE91" box="[559,614,297,317]" gridcol="2" gridrow="2" pageId="2" pageNumber="127">126.82</td>
<td id="450D5D910E6BBDFD98CFFEC9FCFFFE91" box="[685,777,297,317]" gridcol="3" gridrow="2" pageId="2" pageNumber="127">111.02</td>
<td id="450D5D910E6BBDFD9949FEC9FC95FE91" box="[811,867,297,317]" gridcol="4" gridrow="2" pageId="2" pageNumber="127">85.2</td>
<td id="450D5D910E6BBDFD99C8FEC9FBB6FE91" box="[938,1088,297,317]" gridcol="5" gridrow="2" pageId="2" pageNumber="127">C7H13O6</td>
<td id="450D5D910E6BBDFD9EE7FEC9FA33FE91" box="[1157,1477,297,317]" gridcol="6" gridrow="2" pageId="2" pageNumber="127">Quinic acid a</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFEA0FA33FEF8" box="[136,1477,320,340]" gridrow="3" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFEA0FEC2FEF8" box="[136,308,320,340]" gridcol="0" gridrow="3" pageId="2" pageNumber="127">0.52</th>
<td id="450D5D910E6BBDFD9B1AFEA0FE1CFEF8" box="[376,490,320,340]" gridcol="1" gridrow="3" pageId="2" pageNumber="127">162.98</td>
<td id="450D5D910E6BBDFD984DFEA0FD90FEF8" box="[559,614,320,340]" gridcol="2" gridrow="3" pageId="2" pageNumber="127">147.03</td>
<td id="450D5D910E6BBDFD98CFFEA0FCFFFEF8" box="[685,777,320,340]" gridcol="3" gridrow="3" pageId="2" pageNumber="127">119.05</td>
<td id="450D5D910E6BBDFD9949FEA0FC95FEF8" box="[811,867,320,340]" gridcol="4" gridrow="3" pageId="2" pageNumber="127">93.03</td>
<td id="450D5D910E6BBDFD99C8FEA0FBB6FEF8" box="[938,1088,320,340]" gridcol="5" gridrow="3" pageId="2" pageNumber="127">C9H8O3</td>
<td id="450D5D910E6BBDFD9EE7FEA0FA33FEF8" box="[1157,1477,320,340]" gridcol="6" gridrow="3" pageId="2" pageNumber="127">p-Coumaric acid a</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFEB6FA33FEC7" box="[136,1477,342,363]" gridrow="4" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFEB6FEC2FEC7" box="[136,308,342,363]" gridcol="0" gridrow="4" pageId="2" pageNumber="127">1.72</th>
<td id="450D5D910E6BBDFD9B1AFEB6FE1CFEC7" box="[376,490,342,363]" gridcol="1" gridrow="4" pageId="2" pageNumber="127">447.12</td>
<td id="450D5D910E6BBDFD984DFEB6FD90FEC7" box="[559,614,342,363]" gridcol="2" gridrow="4" pageId="2" pageNumber="127">285.07</td>
<td id="450D5D910E6BBDFD98CFFEB6FCFFFEC7" box="[685,777,342,363]" gridcol="3" gridrow="4" pageId="2" pageNumber="127">151.01</td>
<td id="450D5D910E6BBDFD9949FEB6FC95FEC7" box="[811,867,342,363]" gridcol="4" gridrow="4" pageId="2" pageNumber="127">133.2</td>
<td id="450D5D910E6BBDFD99C8FEB6FBB6FEC7" box="[938,1088,342,363]" gridcol="5" gridrow="4" pageId="2" pageNumber="127">C21H20O11</td>
<td id="450D5D910E6BBDFD9EE7FEB6FA33FEC7" box="[1157,1477,342,363]" gridcol="6" gridrow="4" pageId="2" pageNumber="127">Kaempferol 3-O-glucoside a</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFE91FA33FE2D" box="[136,1477,369,385]" gridrow="5" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFE91FEC2FE2D" box="[136,308,369,385]" gridcol="0" gridrow="5" pageId="2" pageNumber="127">1.87</th>
<td id="450D5D910E6BBDFD9B1AFE91FE1CFE2D" box="[376,490,369,385]" gridcol="1" gridrow="5" pageId="2" pageNumber="127">625.14</td>
<td id="450D5D910E6BBDFD984DFE91FD90FE2D" box="[559,614,369,385]" gridcol="2" gridrow="5" pageId="2" pageNumber="127">463.07</td>
<td id="450D5D910E6BBDFD98CFFE91FCFFFE2D" box="[685,777,369,385]" gridcol="3" gridrow="5" pageId="2" pageNumber="127">301.07</td>
<td id="450D5D910E6BBDFD9949FE91FC95FE2D" box="[811,867,369,385]" gridcol="4" gridrow="5" pageId="2" pageNumber="127">151.02</td>
<td id="450D5D910E6BBDFD99C8FE91FBB6FE2D" box="[938,1088,369,385]" gridcol="5" gridrow="5" pageId="2" pageNumber="127">C27H29O17</td>
<td id="450D5D910E6BBDFD9EE7FE91FA33FE2D" box="[1157,1477,369,385]" gridcol="6" gridrow="5" pageId="2" pageNumber="127">Quercetin diglucoside</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFE64FA33FE34" box="[136,1477,388,408]" gridrow="6" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFE64FEC2FE34" box="[136,308,388,408]" gridcol="0" gridrow="6" pageId="2" pageNumber="127">1.89</th>
<td id="450D5D910E6BBDFD9B1AFE64FE1CFE34" box="[376,490,388,408]" gridcol="1" gridrow="6" pageId="2" pageNumber="127">609.15</td>
<td id="450D5D910E6BBDFD984DFE64FD90FE34" box="[559,614,388,408]" gridcol="2" gridrow="6" pageId="2" pageNumber="127">463.08</td>
<td id="450D5D910E6BBDFD98CFFE64FCFFFE34" box="[685,777,388,408]" gridcol="3" gridrow="6" pageId="2" pageNumber="127">301.05</td>
<td id="450D5D910E6BBDFD9949FE64FC95FE34" box="[811,867,388,408]" gridcol="4" gridrow="6" pageId="2" pageNumber="127">151.02</td>
<td id="450D5D910E6BBDFD99C8FE64FBB6FE34" box="[938,1088,388,408]" gridcol="5" gridrow="6" pageId="2" pageNumber="127">C27H30O16</td>
<td id="450D5D910E6BBDFD9EE7FE64FA33FE34" box="[1157,1477,388,408]" gridcol="6" gridrow="6" pageId="2" pageNumber="127">Quercetin rutinoside isomer 1 a</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFE7BFA33FE03" box="[136,1477,411,431]" gridrow="7" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFE7BFEC2FE03" box="[136,308,411,431]" gridcol="0" gridrow="7" pageId="2" pageNumber="127">1.93</th>
<td id="450D5D910E6BBDFD9B1AFE7BFE1CFE03" box="[376,490,411,431]" gridcol="1" gridrow="7" pageId="2" pageNumber="127">639.16</td>
<td id="450D5D910E6BBDFD984DFE7BFD90FE03" box="[559,614,411,431]" gridcol="2" gridrow="7" pageId="2" pageNumber="127">477.16</td>
<td id="450D5D910E6BBDFD98CFFE7BFCFFFE03" box="[685,777,411,431]" gridcol="3" gridrow="7" pageId="2" pageNumber="127">315.11</td>
<td id="450D5D910E6BBDFD9949FE7BFC95FE03" box="[811,867,411,431]" gridcol="4" gridrow="7" pageId="2" pageNumber="127">300.08</td>
<td id="450D5D910E6BBDFD99C8FE7BFBB6FE03" box="[938,1088,411,431]" gridcol="5" gridrow="7" pageId="2" pageNumber="127">C28H32O17</td>
<td id="450D5D910E6BBDFD9EE7FE7BFA33FE03" box="[1157,1477,411,431]" gridcol="6" gridrow="7" pageId="2" pageNumber="127">Isorhamnetin 3-O-diglucoside a</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFE52FA33FE6A" box="[136,1477,434,454]" gridrow="8" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFE52FEC2FE6A" box="[136,308,434,454]" gridcol="0" gridrow="8" pageId="2" pageNumber="127">1.95</th>
<td id="450D5D910E6BBDFD9B1AFE52FE1CFE6A" box="[376,490,434,454]" gridcol="1" gridrow="8" pageId="2" pageNumber="127">625.35</td>
<td id="450D5D910E6BBDFD984DFE52FD90FE6A" box="[559,614,434,454]" gridcol="2" gridrow="8" pageId="2" pageNumber="127">477.19</td>
<td id="450D5D910E6BBDFD98CFFE52FCFFFE6A" box="[685,777,434,454]" gridcol="3" gridrow="8" pageId="2" pageNumber="127">315.20</td>
<td id="450D5D910E6BBDFD9949FE52FC95FE6A" box="[811,867,434,454]" gridcol="4" gridrow="8" pageId="2" pageNumber="127">151.03</td>
<td id="450D5D910E6BBDFD99C8FE52FBB6FE6A" box="[938,1088,434,454]" gridcol="5" gridrow="8" pageId="2" pageNumber="127">C28H32O16</td>
<td id="450D5D910E6BBDFD9EE7FE52FA33FE6A" box="[1157,1477,434,454]" gridcol="6" gridrow="8" pageId="2" pageNumber="127">Isorhamnetin rutinoside a</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFE29FA33FE71" box="[136,1477,457,477]" gridrow="9" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFE29FEC2FE71" box="[136,308,457,477]" gridcol="0" gridrow="9" pageId="2" pageNumber="127">1.97</th>
<td id="450D5D910E6BBDFD9B1AFE29FE1CFE71" box="[376,490,457,477]" gridcol="1" gridrow="9" pageId="2" pageNumber="127">609.15</td>
<td id="450D5D910E6BBDFD984DFE29FD90FE71" box="[559,614,457,477]" gridcol="2" gridrow="9" pageId="2" pageNumber="127">445.15</td>
<td id="450D5D910E6BBDFD98CFFE29FCFFFE71" box="[685,777,457,477]" gridcol="3" gridrow="9" pageId="2" pageNumber="127">315.10</td>
<td id="450D5D910E6BBDFD9949FE29FC95FE71" box="[811,867,457,477]" gridcol="4" gridrow="9" pageId="2" pageNumber="127">300.05</td>
<td id="450D5D910E6BBDFD99C8FE29FBB6FE71" box="[938,1088,457,477]" gridcol="5" gridrow="9" pageId="2" pageNumber="127">C27H30O16</td>
<td id="450D5D910E6BBDFD9EE7FE29FA33FE71" box="[1157,1477,457,477]" gridcol="6" gridrow="9" pageId="2" pageNumber="127">Quercetin rutinoside isomer 2a</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFE03FA33FE58" box="[136,1477,483,500]" gridrow="10" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFE03FEC2FE58" box="[136,308,483,500]" gridcol="0" gridrow="10" pageId="2" pageNumber="127">2.01</th>
<td id="450D5D910E6BBDFD9B1AFE03FE1CFE58" box="[376,490,483,500]" gridcol="1" gridrow="10" pageId="2" pageNumber="127">595.14</td>
<td id="450D5D910E6BBDFD984DFE03FD90FE58" box="[559,614,483,500]" gridcol="2" gridrow="10" pageId="2" pageNumber="127">463.07</td>
<td id="450D5D910E6BBDFD98CFFE03FCFFFE58" box="[685,777,483,500]" gridcol="3" gridrow="10" pageId="2" pageNumber="127">301.06</td>
<td id="450D5D910E6BBDFD9949FE03FC95FE58" box="[811,867,483,500]" gridcol="4" gridrow="10" pageId="2" pageNumber="127">255.01</td>
<td id="450D5D910E6BBDFD99C8FE03FBB6FE58" box="[938,1088,483,500]" gridcol="5" gridrow="10" pageId="2" pageNumber="127">C26H28O16</td>
<td id="450D5D910E6BBDFD9EE7FE03FA33FE58" box="[1157,1477,483,500]" gridcol="6" gridrow="10" pageId="2" pageNumber="127">Quercetin 3-O-glucosyl-6-O-pentoside</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFE1AFA33FDA7" box="[136,1477,506,523]" gridrow="11" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFE1AFEC2FDA7" box="[136,308,506,523]" gridcol="0" gridrow="11" pageId="2" pageNumber="127">2.07</th>
<td id="450D5D910E6BBDFD9B1AFE1AFE1CFDA7" box="[376,490,506,523]" gridcol="1" gridrow="11" pageId="2" pageNumber="127">463.09</td>
<td id="450D5D910E6BBDFD984DFE1AFD90FDA7" box="[559,614,506,523]" gridcol="2" gridrow="11" pageId="2" pageNumber="127">301.04</td>
<td id="450D5D910E6BBDFD98CFFE1AFCFFFDA7" box="[685,777,506,523]" gridcol="3" gridrow="11" pageId="2" pageNumber="127">151.10</td>
<td id="450D5D910E6BBDFD9949FE1AFC95FDA7" box="[811,867,506,523]" gridcol="4" gridrow="11" pageId="2" pageNumber="127">149.02</td>
<td id="450D5D910E6BBDFD99C8FE1AFBB6FDA7" box="[938,1088,506,523]" gridcol="5" gridrow="11" pageId="2" pageNumber="127">C21H20O12</td>
<td id="450D5D910E6BBDFD9EE7FE1AFA33FDA7" box="[1157,1477,506,523]" gridcol="6" gridrow="11" pageId="2" pageNumber="127">Quercetin 3-O-glucoside</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFDEDFA33FD8D" box="[136,1477,525,545]" gridrow="12" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFDEDFEC2FD8D" box="[136,308,525,545]" gridcol="0" gridrow="12" pageId="2" pageNumber="127">2.07</th>
<td id="450D5D910E6BBDFD9B1AFDEDFE1CFD8D" box="[376,490,525,545]" gridcol="1" gridrow="12" pageId="2" pageNumber="127">593.15</td>
<td id="450D5D910E6BBDFD984DFDEDFD90FD8D" box="[559,614,525,545]" gridcol="2" gridrow="12" pageId="2" pageNumber="127">447.09</td>
<td id="450D5D910E6BBDFD98CFFDEDFCFFFD8D" box="[685,777,525,545]" gridcol="3" gridrow="12" pageId="2" pageNumber="127">315.07</td>
<td id="450D5D910E6BBDFD9949FDEDFC95FD8D" box="[811,867,525,545]" gridcol="4" gridrow="12" pageId="2" pageNumber="127">241.09</td>
<td id="450D5D910E6BBDFD99C8FDEDFBB6FD8D" box="[938,1088,525,545]" gridcol="5" gridrow="12" pageId="2" pageNumber="127">C27H30O15</td>
<td id="450D5D910E6BBDFD9EE7FDEDFA33FD8D" box="[1157,1477,525,545]" gridcol="6" gridrow="12" pageId="2" pageNumber="127">Kaempferol rutinoside a</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFDC4FA33FD94" box="[136,1477,548,568]" gridrow="13" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFDC4FEC2FD94" box="[136,308,548,568]" gridcol="0" gridrow="13" pageId="2" pageNumber="127">2.15</th>
<td id="450D5D910E6BBDFD9B1AFDC4FE1CFD94" box="[376,490,548,568]" gridcol="1" gridrow="13" pageId="2" pageNumber="127">549.09</td>
<td id="450D5D910E6BBDFD984DFDC4FD90FD94" box="[559,614,548,568]" gridcol="2" gridrow="13" pageId="2" pageNumber="127">505.13</td>
<td id="450D5D910E6BBDFD98CFFDC4FCFFFD94" box="[685,777,548,568]" gridcol="3" gridrow="13" pageId="2" pageNumber="127">463.07</td>
<td id="450D5D910E6BBDFD9949FDC4FC95FD94" box="[811,867,548,568]" gridcol="4" gridrow="13" pageId="2" pageNumber="127">300.87</td>
<td id="450D5D910E6BBDFD99C8FDC4FBB6FD94" box="[938,1088,548,568]" gridcol="5" gridrow="13" pageId="2" pageNumber="127">C24H22O15</td>
<td id="450D5D910E6BBDFD9EE7FDC4FA33FD94" box="[1157,1477,548,568]" gridcol="6" gridrow="13" pageId="2" pageNumber="127">Quercetin 3-O-malonyl glucoside a</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFDDEFA33FDE3" box="[136,1477,574,591]" gridrow="14" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFDDEFEC2FDE3" box="[136,308,574,591]" gridcol="0" gridrow="14" pageId="2" pageNumber="127">2.20</th>
<td id="450D5D910E6BBDFD9B1AFDDEFE1CFDE3" box="[376,490,574,591]" gridcol="1" gridrow="14" pageId="2" pageNumber="127">490.98</td>
<td id="450D5D910E6BBDFD984DFDDEFD90FDE3" box="[559,614,574,591]" gridcol="2" gridrow="14" pageId="2" pageNumber="127">301.03</td>
<td id="450D5D910E6BBDFD98CFFDDEFCFFFDE3" box="[685,777,574,591]" gridcol="3" gridrow="14" pageId="2" pageNumber="127">179.10</td>
<td id="450D5D910E6BBDFD9949FDDEFC95FDE3" box="[811,867,574,591]" gridcol="4" gridrow="14" pageId="2" pageNumber="127">151.01</td>
<td id="450D5D910E6BBDFD99C8FDDEFBB6FDE3" box="[938,1088,574,591]" gridcol="5" gridrow="14" pageId="2" pageNumber="127">C22H22O13</td>
<td id="450D5D910E6BBDFD9EE7FDDEFA33FDE3" box="[1157,1477,574,591]" gridcol="6" gridrow="14" pageId="2" pageNumber="127">Quercetin 3-O-methyl hexuronide</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFDB5FA33FDCA" box="[136,1477,597,614]" gridrow="15" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFDB5FEC2FDCA" box="[136,308,597,614]" gridcol="0" gridrow="15" pageId="2" pageNumber="127">2.21</th>
<td id="450D5D910E6BBDFD9B1AFDB5FE1CFDCA" box="[376,490,597,614]" gridcol="1" gridrow="15" pageId="2" pageNumber="127">505.10</td>
<td id="450D5D910E6BBDFD984DFDB5FD90FDCA" box="[559,614,597,614]" gridcol="2" gridrow="15" pageId="2" pageNumber="127">461.10</td>
<td id="450D5D910E6BBDFD98CFFDB5FCFFFDCA" box="[685,777,597,614]" gridcol="3" gridrow="15" pageId="2" pageNumber="127">315.04</td>
<td id="450D5D910E6BBDFD9949FDB5FC95FDCA" box="[811,867,597,614]" gridcol="4" gridrow="15" pageId="2" pageNumber="127">151.06</td>
<td id="450D5D910E6BBDFD99C8FDB5FBB6FDCA" box="[938,1088,597,614]" gridcol="5" gridrow="15" pageId="2" pageNumber="127">C23H24O13</td>
<td id="450D5D910E6BBDFD9EE7FDB5FA33FDCA" box="[1157,1477,597,614]" gridcol="6" gridrow="15" pageId="2" pageNumber="127">Isorhamnetin 3-O-methyl hexuronide</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFD8CFA33FDD1" box="[136,1477,620,637]" gridrow="16" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFD8CFEC2FDD1" box="[136,308,620,637]" gridcol="0" gridrow="16" pageId="2" pageNumber="127">2.25</th>
<td id="450D5D910E6BBDFD9B1AFD8CFE1CFDD1" box="[376,490,620,637]" gridcol="1" gridrow="16" pageId="2" pageNumber="127">477.10</td>
<td id="450D5D910E6BBDFD984DFD8CFD90FDD1" box="[559,614,620,637]" gridcol="2" gridrow="16" pageId="2" pageNumber="127">357.09</td>
<td id="450D5D910E6BBDFD98CFFD8CFCFFFDD1" box="[685,777,620,637]" gridcol="3" gridrow="16" pageId="2" pageNumber="127">314.03</td>
<td id="450D5D910E6BBDFD9949FD8CFC95FDD1" box="[811,867,620,637]" gridcol="4" gridrow="16" pageId="2" pageNumber="127">285.10</td>
<td id="450D5D910E6BBDFD99C8FD8CFBB6FDD1" box="[938,1088,620,637]" gridcol="5" gridrow="16" pageId="2" pageNumber="127">C22H22O12</td>
<td id="450D5D910E6BBDFD9EE7FD8CFA33FDD1" box="[1157,1477,620,637]" gridcol="6" gridrow="16" pageId="2" pageNumber="127">Isorhamnetin 3-O-glucoside</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFD63FA33FD38" box="[136,1477,643,660]" gridrow="17" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFD63FEC2FD38" box="[136,308,643,660]" gridcol="0" gridrow="17" pageId="2" pageNumber="127">2.34</th>
<td id="450D5D910E6BBDFD9B1AFD63FE1CFD38" box="[376,490,643,660]" gridcol="1" gridrow="17" pageId="2" pageNumber="127">533.09</td>
<td id="450D5D910E6BBDFD984DFD63FD90FD38" box="[559,614,643,660]" gridcol="2" gridrow="17" pageId="2" pageNumber="127">489.15</td>
<td id="450D5D910E6BBDFD98CFFD63FCFFFD38" box="[685,777,643,660]" gridcol="3" gridrow="17" pageId="2" pageNumber="127">428.89</td>
<td id="450D5D910E6BBDFD9949FD63FC95FD38" box="[811,867,643,660]" gridcol="4" gridrow="17" pageId="2" pageNumber="127">285.05</td>
<td id="450D5D910E6BBDFD99C8FD63FBB6FD38" box="[938,1088,643,660]" gridcol="5" gridrow="17" pageId="2" pageNumber="127">C24H20O14</td>
<td id="450D5D910E6BBDFD9EE7FD63FA33FD38" box="[1157,1477,643,660]" gridcol="6" gridrow="17" pageId="2" pageNumber="127">Kaempferol O-malonyl-acetyl glucoside</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFD7AFA33FD07" box="[136,1477,666,683]" gridrow="18" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFD7AFEC2FD07" box="[136,308,666,683]" gridcol="0" gridrow="18" pageId="2" pageNumber="127">2.38</th>
<td id="450D5D910E6BBDFD9B1AFD7AFE1CFD07" box="[376,490,666,683]" gridcol="1" gridrow="18" pageId="2" pageNumber="127">519.12</td>
<td id="450D5D910E6BBDFD984DFD7AFD90FD07" box="[559,614,666,683]" gridcol="2" gridrow="18" pageId="2" pageNumber="127">477.14</td>
<td id="450D5D910E6BBDFD98CFFD7AFCFFFD07" box="[685,777,666,683]" gridcol="3" gridrow="18" pageId="2" pageNumber="127">403.11</td>
<td id="450D5D910E6BBDFD9949FD7AFC95FD07" box="[811,867,666,683]" gridcol="4" gridrow="18" pageId="2" pageNumber="127">315.05</td>
<td id="450D5D910E6BBDFD99C8FD7AFBB6FD07" box="[938,1088,666,683]" gridcol="5" gridrow="18" pageId="2" pageNumber="127">C25H24O13</td>
<td id="450D5D910E6BBDFD9EE7FD7AFA33FD07" box="[1157,1477,666,683]" gridcol="6" gridrow="18" pageId="2" pageNumber="127">Isorhamnetin 3-O-acetyl glucoside</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFD51FA33FD6D" box="[136,1477,689,705]" gridrow="19" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFD51FEC2FD6D" box="[136,308,689,705]" gridcol="0" gridrow="19" pageId="2" pageNumber="127">2.38</th>
<td id="450D5D910E6BBDFD9B1AFD51FE1CFD6D" box="[376,490,689,705]" gridcol="1" gridrow="19" pageId="2" pageNumber="127">563.11</td>
<td id="450D5D910E6BBDFD984DFD51FD90FD6D" box="[559,614,689,705]" gridcol="2" gridrow="19" pageId="2" pageNumber="127">519.03</td>
<td id="450D5D910E6BBDFD98CFFD51FCFFFD6D" box="[685,777,689,705]" gridcol="3" gridrow="19" pageId="2" pageNumber="127">403.11</td>
<td id="450D5D910E6BBDFD9949FD51FC95FD6D" box="[811,867,689,705]" gridcol="4" gridrow="19" pageId="2" pageNumber="127">315.06</td>
<td id="450D5D910E6BBDFD99C8FD51FBB6FD6D" box="[938,1088,689,705]" gridcol="5" gridrow="19" pageId="2" pageNumber="127">C25H23O15</td>
<td id="450D5D910E6BBDFD9EE7FD51FA33FD6D" box="[1157,1477,689,705]" gridcol="6" gridrow="19" pageId="2" pageNumber="127">Isorhamnetin 3-O-malonyl glucoside</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFD27FA33FD74" box="[136,1477,711,728]" gridrow="20" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFD27FEC2FD74" box="[136,308,711,728]" gridcol="0" gridrow="20" pageId="2" pageNumber="127">2.93</th>
<td id="450D5D910E6BBDFD9B1AFD27FE1CFD74" box="[376,490,711,728]" gridcol="1" gridrow="20" pageId="2" pageNumber="127">598.26</td>
<td id="450D5D910E6BBDFD984DFD27FD90FD74" box="[559,614,711,728]" gridcol="2" gridrow="20" pageId="2" pageNumber="127">478.20</td>
<td id="450D5D910E6BBDFD98CFFD27FCFFFD74" box="[685,777,711,728]" gridcol="3" gridrow="20" pageId="2" pageNumber="127">436.17</td>
<td id="450D5D910E6BBDFD9949FD27FC95FD74" box="[811,867,711,728]" gridcol="4" gridrow="20" pageId="2" pageNumber="127">358.19</td>
<td id="450D5D910E6BBDFD99C8FD27FBB6FD74" box="[938,1088,711,728]" gridcol="5" gridrow="20" pageId="2" pageNumber="127">C34H37N3O7</td>
<td id="450D5D910E6BBDFD9EE7FD27FA33FD74" box="[1157,1477,711,728]" gridcol="6" gridrow="20" pageId="2" pageNumber="127">di Coumaroyl caffeoyl spermidine</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFD3EFA33FD43" box="[136,1477,734,751]" gridrow="21" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFD3EFEC2FD43" box="[136,308,734,751]" gridcol="0" gridrow="21" pageId="2" pageNumber="127">2.96</th>
<td id="450D5D910E6BBDFD9B1AFD3EFE1CFD43" box="[376,490,734,751]" gridcol="1" gridrow="21" pageId="2" pageNumber="127">582.26</td>
<td id="450D5D910E6BBDFD984DFD3EFD90FD43" box="[559,614,734,751]" gridcol="2" gridrow="21" pageId="2" pageNumber="127">462.22</td>
<td id="450D5D910E6BBDFD98CFFD3EFCFFFD43" box="[685,777,734,751]" gridcol="3" gridrow="21" pageId="2" pageNumber="127">436.17</td>
<td id="450D5D910E6BBDFD9949FD3EFC95FD43" box="[811,867,734,751]" gridcol="4" gridrow="21" pageId="2" pageNumber="127">342.16</td>
<td id="450D5D910E6BBDFD99C8FD3EFBB6FD43" box="[938,1088,734,751]" gridcol="5" gridrow="21" pageId="2" pageNumber="127">C34H37N3O6</td>
<td id="450D5D910E6BBDFD9EE7FD3EFA33FD43" box="[1157,1477,734,751]" gridcol="6" gridrow="21" pageId="2" pageNumber="127">tri-p-Coumaroyl spermidine</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFD15FA33FCAA" box="[136,1477,757,774]" gridrow="22" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFD15FEC2FCAA" box="[136,308,757,774]" gridcol="0" gridrow="22" pageId="2" pageNumber="127">3.03</th>
<td id="450D5D910E6BBDFD9B1AFD15FE1CFCAA" box="[376,490,757,774]" gridcol="1" gridrow="22" pageId="2" pageNumber="127">787.36</td>
<td id="450D5D910E6BBDFD984DFD15FD90FCAA" box="[559,614,757,774]" gridcol="2" gridrow="22" pageId="2" pageNumber="127">477.20</td>
<td id="450D5D910E6BBDFD98CFFD15FCFFFCAA" box="[685,777,757,774]" gridcol="3" gridrow="22" pageId="2" pageNumber="127">374.06</td>
<td id="450D5D910E6BBDFD9949FD15FC95FCAA" box="[811,867,757,774]" gridcol="4" gridrow="22" pageId="2" pageNumber="127">315.20</td>
<td id="450D5D910E6BBDFD99C8FD15FBB6FCAA" box="[938,1088,757,774]" gridcol="5" gridrow="22" pageId="2" pageNumber="127">C36H47O19</td>
<td id="450D5D910E6BBDFD9EE7FD15FA33FCAA" box="[1157,1477,757,774]" gridcol="6" gridrow="22" pageId="2" pageNumber="127">Isorhamnetin rutinosyl glucoside</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFCE8FA33FCB1" box="[136,1477,776,797]" gridrow="23" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFCE8FEC2FCB1" box="[136,308,776,797]" gridcol="0" gridrow="23" pageId="2" pageNumber="127">4.68</th>
<td id="450D5D910E6BBDFD9B1AFCE8FE1CFCB1" box="[376,490,776,797]" gridcol="1" gridrow="23" pageId="2" pageNumber="127">353.20</td>
<td id="450D5D910E6BBDFD984DFCE8FD90FCB1" box="[559,614,776,797]" gridcol="2" gridrow="23" pageId="2" pageNumber="127">309.25</td>
<td id="450D5D910E6BBDFD98CFFCE8FCFFFCB1" box="[685,777,776,797]" gridcol="3" gridrow="23" pageId="2" pageNumber="127">295.09</td>
<td id="450D5D910E6BBDFD9949FCE8FC95FCB1" box="[811,867,776,797]" gridcol="4" gridrow="23" pageId="2" pageNumber="127">262.48</td>
<td id="450D5D910E6BBDFD99C8FCE8FBB6FCB1" box="[938,1088,776,797]" gridcol="5" gridrow="23" pageId="2" pageNumber="127">C16H18O9</td>
<td id="450D5D910E6BBDFD9EE7FCE8FA33FCB1" box="[1157,1477,776,797]" gridcol="6" gridrow="23" pageId="2" pageNumber="127">Caffeoyl quinic acid a</td>
</tr>
</table>
</paragraph>
<paragraph id="B85336AF0E6B42009AE3FCCFFD6EFCED" blockId="2.[129,664,815,833]" box="[129,664,815,833]" pageId="2" pageNumber="127">
<tableNote id="450A37210E6B42009AE3FCCFFD6EFCED" box="[129,664,815,833]" pageId="2" pageNumber="127" targetBox="[136,1477,243,797]" targetPageId="2">
<superScript id="4F999BE70E6B42009AE3FCCFFF7EFC94" attach="left" box="[129,136,815,824]" fontSize="4" pageId="2" pageNumber="127">a</superScript>
Compounds found solely in whole pollen grains and not in SPP.
</tableNote>
</paragraph>
<caption id="EC9366270E6B42009A10FC64FBA0FC05" pageId="2" pageNumber="127" startId="2.[114,158,900,914]" targetBox="[136,1477,960,1263]" targetIsTable="true" targetPageId="2" targetType="table">
<paragraph id="B85336AF0E6B42009A10FC64FBA0FC05" blockId="2.[113,1110,900,937]" pageId="2" pageNumber="127">
<emphasis id="8A98EABD0E6B42009A10FC64FF58FC3E" bold="true" box="[114,174,900,914]" pageId="2" pageNumber="127">Table 2</emphasis>
Compounds detected in 
<taxonomicName id="7FEC4D2C0E6B42009B51FC7AFE5CFC05" box="[307,426,922,937]" class="Magnoliopsida" family="Asteraceae" genus="Ambrosia" kingdom="Plantae" order="Asterales" pageId="2" pageNumber="127" phylum="Tracheophyta" rank="species" species="artemisiifolia">
<emphasis id="8A98EABD0E6B42009B51FC7AFE5CFC05" box="[307,426,922,937]" italics="true" pageId="2" pageNumber="127">A. artemisiifolia</emphasis>
</taxonomicName>
L. sub-pollen particle aqueous extract on the UHPLC/ESI-Orbitrap mass spectrometer.
</paragraph>
</caption>
<paragraph id="B85336AF0E6B42009AEAFC21FA66FB40" pageId="2" pageNumber="127">
<table id="CAECC40F0E6BBDFD9AEAFC20FA33FB43" box="[136,1477,960,1263]" gridcols="7" gridrows="13" pageId="2" pageNumber="127">
<tr id="06DC34ED0E6BBDFD9AEAFC20FA33FC7C" box="[136,1477,960,976]" gridrow="0" pageId="2" pageNumber="127" rowspan-4="1">
<th id="450D5D910E6BBDFD9AEAFC20FEC2FC7C" box="[136,308,960,976]" gridcol="0" gridrow="0" pageId="2" pageNumber="127">Retention time (min)</th>
<th id="450D5D910E6BBDFD9B1AFC20FE1FFC7C" box="[376,489,960,976]" gridcol="1" gridrow="0" pageId="2" pageNumber="127">
Measured 
<emphasis id="8A98EABD0E6B42009BAFFC20FE1FFC63" box="[461,489,960,975]" italics="true" pageId="2" pageNumber="127">m/z</emphasis>
</th>
<th id="450D5D910E6BBDFD984CFC20FCFFFC7C" box="[558,777,960,976]" colspan="2" colspanRight="1" gridcol="2" gridrow="0" pageId="2" pageNumber="127">
Diagnostic fragments (
<emphasis id="8A98EABD0E6B42009884FC20FCF4FC63" box="[742,770,960,975]" italics="true" pageId="2" pageNumber="127">m/z</emphasis>
)
</th>
<th id="450D5D910E6BBDFD99C8FC20FBB6FC7C" box="[938,1088,960,976]" gridcol="5" gridrow="0" pageId="2" pageNumber="127">Molecular formula</th>
<th id="450D5D910E6BBDFD9EE7FC20FA33FC7C" box="[1157,1477,960,976]" gridcol="6" gridrow="0" pageId="2" pageNumber="127">Compound name</th>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFC03FA33FC5F" box="[136,1477,995,1011]" gridrow="1" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFC03FEC2FC5F" box="[136,308,995,1011]" gridcol="0" gridrow="1" pageId="2" pageNumber="127">1.87</th>
<td id="450D5D910E6BBDFD9B1AFC03FE1FFC5F" box="[376,489,995,1011]" gridcol="1" gridrow="1" pageId="2" pageNumber="127">625.14</td>
<td id="450D5D910E6BBDFD984CFC03FD93FC5F" box="[558,613,995,1011]" gridcol="2" gridrow="1" pageId="2" pageNumber="127">463.06</td>
<td id="450D5D910E6BBDFD98CFFC03FCFFFC5F" box="[685,777,995,1011]" gridcol="3" gridrow="1" pageId="2" pageNumber="127">301.07</td>
<td id="450D5D910E6BBDFD9949FC03FC94FC5F" box="[811,866,995,1011]" gridcol="4" gridrow="1" pageId="2" pageNumber="127">151.02</td>
<td id="450D5D910E6BBDFD99C8FC03FBB6FC5F" box="[938,1088,995,1011]" gridcol="5" gridrow="1" pageId="2" pageNumber="127">C27H29O17</td>
<td id="450D5D910E6BBDFD9EE7FC03FA33FC5F" box="[1157,1477,995,1011]" gridcol="6" gridrow="1" pageId="2" pageNumber="127">Quercetin di-glucoside</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFC1AFA33FBA6" box="[136,1477,1018,1034]" gridrow="2" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFC1AFEC2FBA6" box="[136,308,1018,1034]" gridcol="0" gridrow="2" pageId="2" pageNumber="127">2.08</th>
<td id="450D5D910E6BBDFD9B1AFC1AFE1FFBA6" box="[376,489,1018,1034]" gridcol="1" gridrow="2" pageId="2" pageNumber="127">595.14</td>
<td id="450D5D910E6BBDFD984CFC1AFD93FBA6" box="[558,613,1018,1034]" gridcol="2" gridrow="2" pageId="2" pageNumber="127">463.07</td>
<td id="450D5D910E6BBDFD98CFFC1AFCFFFBA6" box="[685,777,1018,1034]" gridcol="3" gridrow="2" pageId="2" pageNumber="127">301.06</td>
<td id="450D5D910E6BBDFD9949FC1AFC94FBA6" box="[811,866,1018,1034]" gridcol="4" gridrow="2" pageId="2" pageNumber="127">255.02</td>
<td id="450D5D910E6BBDFD99C8FC1AFBB6FBA6" box="[938,1088,1018,1034]" gridcol="5" gridrow="2" pageId="2" pageNumber="127">C26H28O16</td>
<td id="450D5D910E6BBDFD9EE7FC1AFA33FBA6" box="[1157,1477,1018,1034]" gridcol="6" gridrow="2" pageId="2" pageNumber="127">Quercetin 3-O-glucosyl-6-O-pentoside</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFBF1FA33FB8D" box="[136,1477,1041,1057]" gridrow="3" pageId="2" pageNumber="127" rowspan-4="1">
<th id="450D5D910E6BBDFD9AEAFBF1FEC2FB8D" box="[136,308,1041,1057]" gridcol="0" gridrow="3" pageId="2" pageNumber="127">2.13</th>
<td id="450D5D910E6BBDFD9B1AFBF1FE1FFB8D" box="[376,489,1041,1057]" gridcol="1" gridrow="3" pageId="2" pageNumber="127">463.09</td>
<td id="450D5D910E6BBDFD984CFBF1FD93FB8D" box="[558,613,1041,1057]" gridcol="2" gridrow="3" pageId="2" pageNumber="127">301.03</td>
<td id="450D5D910E6BBDFD98CFFBF1FCFFFB8D" box="[685,777,1041,1057]" gridcol="3" gridrow="3" pageId="2" pageNumber="127">179.10</td>
<td id="450D5D910E6BBDFD99C8FBF1FBB6FB8D" box="[938,1088,1041,1057]" gridcol="5" gridrow="3" pageId="2" pageNumber="127">C21H20O12</td>
<td id="450D5D910E6BBDFD9EE7FBF1FA33FB8D" box="[1157,1477,1041,1057]" gridcol="6" gridrow="3" pageId="2" pageNumber="127">Quercetin 3-O-glucoside</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFBC7FA33FB94" box="[136,1477,1063,1080]" gridrow="4" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFBC7FEC2FB94" box="[136,308,1063,1080]" gridcol="0" gridrow="4" pageId="2" pageNumber="127">2.18</th>
<td id="450D5D910E6BBDFD9B1AFBC7FE1FFB94" box="[376,489,1063,1080]" gridcol="1" gridrow="4" pageId="2" pageNumber="127">490.98</td>
<td id="450D5D910E6BBDFD984CFBC7FD93FB94" box="[558,613,1063,1080]" gridcol="2" gridrow="4" pageId="2" pageNumber="127">301.04</td>
<td id="450D5D910E6BBDFD98CFFBC7FCFFFB94" box="[685,777,1063,1080]" gridcol="3" gridrow="4" pageId="2" pageNumber="127">179.10</td>
<td id="450D5D910E6BBDFD9949FBC7FC94FB94" box="[811,866,1063,1080]" gridcol="4" gridrow="4" pageId="2" pageNumber="127">151.03</td>
<td id="450D5D910E6BBDFD99C8FBC7FBB6FB94" box="[938,1088,1063,1080]" gridcol="5" gridrow="4" pageId="2" pageNumber="127">C22H22O13</td>
<td id="450D5D910E6BBDFD9EE7FBC7FA33FB94" box="[1157,1477,1063,1080]" gridcol="6" gridrow="4" pageId="2" pageNumber="127">Quercetin O-methyl hexuronide</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFBDEFA33FBE3" box="[136,1477,1086,1103]" gridrow="5" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFBDEFEC2FBE3" box="[136,308,1086,1103]" gridcol="0" gridrow="5" pageId="2" pageNumber="127">2.21</th>
<td id="450D5D910E6BBDFD9B1AFBDEFE1FFBE3" box="[376,489,1086,1103]" gridcol="1" gridrow="5" pageId="2" pageNumber="127">505.10</td>
<td id="450D5D910E6BBDFD984CFBDEFD93FBE3" box="[558,613,1086,1103]" gridcol="2" gridrow="5" pageId="2" pageNumber="127">461.10</td>
<td id="450D5D910E6BBDFD98CFFBDEFCFFFBE3" box="[685,777,1086,1103]" gridcol="3" gridrow="5" pageId="2" pageNumber="127">315.04</td>
<td id="450D5D910E6BBDFD9949FBDEFC94FBE3" box="[811,866,1086,1103]" gridcol="4" gridrow="5" pageId="2" pageNumber="127">151.06</td>
<td id="450D5D910E6BBDFD99C8FBDEFBB6FBE3" box="[938,1088,1086,1103]" gridcol="5" gridrow="5" pageId="2" pageNumber="127">C23H24O13</td>
<td id="450D5D910E6BBDFD9EE7FBDEFA33FBE3" box="[1157,1477,1086,1103]" gridcol="6" gridrow="5" pageId="2" pageNumber="127">Isorhamnetin O-methyl hexuronide</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFBB5FA33FBCA" box="[136,1477,1109,1126]" gridrow="6" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFBB5FEC2FBCA" box="[136,308,1109,1126]" gridcol="0" gridrow="6" pageId="2" pageNumber="127">2.29</th>
<td id="450D5D910E6BBDFD9B1AFBB5FE1FFBCA" box="[376,489,1109,1126]" gridcol="1" gridrow="6" pageId="2" pageNumber="127">477.11</td>
<td id="450D5D910E6BBDFD984CFBB5FD93FBCA" box="[558,613,1109,1126]" gridcol="2" gridrow="6" pageId="2" pageNumber="127">357.08</td>
<td id="450D5D910E6BBDFD98CFFBB5FCFFFBCA" box="[685,777,1109,1126]" gridcol="3" gridrow="6" pageId="2" pageNumber="127">314.03</td>
<td id="450D5D910E6BBDFD9949FBB5FC94FBCA" box="[811,866,1109,1126]" gridcol="4" gridrow="6" pageId="2" pageNumber="127">285.08</td>
<td id="450D5D910E6BBDFD99C8FBB5FBB6FBCA" box="[938,1088,1109,1126]" gridcol="5" gridrow="6" pageId="2" pageNumber="127">C22H22O12</td>
<td id="450D5D910E6BBDFD9EE7FBB5FA33FBCA" box="[1157,1477,1109,1126]" gridcol="6" gridrow="6" pageId="2" pageNumber="127">Isorhamnetin 3-O-glucoside</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFB8CFA33FBD0" box="[136,1477,1132,1148]" gridrow="7" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFB8CFEC2FBD0" box="[136,308,1132,1148]" gridcol="0" gridrow="7" pageId="2" pageNumber="127">2.34</th>
<td id="450D5D910E6BBDFD9B1AFB8CFE1FFBD0" box="[376,489,1132,1148]" gridcol="1" gridrow="7" pageId="2" pageNumber="127">533.09</td>
<td id="450D5D910E6BBDFD984CFB8CFD93FBD0" box="[558,613,1132,1148]" gridcol="2" gridrow="7" pageId="2" pageNumber="127">489.15</td>
<td id="450D5D910E6BBDFD98CFFB8CFCFFFBD0" box="[685,777,1132,1148]" gridcol="3" gridrow="7" pageId="2" pageNumber="127">428.89</td>
<td id="450D5D910E6BBDFD9949FB8CFC94FBD0" box="[811,866,1132,1148]" gridcol="4" gridrow="7" pageId="2" pageNumber="127">285.05</td>
<td id="450D5D910E6BBDFD99C8FB8CFBB6FBD0" box="[938,1088,1132,1148]" gridcol="5" gridrow="7" pageId="2" pageNumber="127">C24H20O14</td>
<td id="450D5D910E6BBDFD9EE7FB8CFA33FBD0" box="[1157,1477,1132,1148]" gridcol="6" gridrow="7" pageId="2" pageNumber="127">Kaempferol O-malonyl-acetyl glucoside</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFB63FA33FB3F" box="[136,1477,1155,1171]" gridrow="8" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFB63FEC2FB3F" box="[136,308,1155,1171]" gridcol="0" gridrow="8" pageId="2" pageNumber="127">2.37</th>
<td id="450D5D910E6BBDFD9B1AFB63FE1FFB3F" box="[376,489,1155,1171]" gridcol="1" gridrow="8" pageId="2" pageNumber="127">519.12</td>
<td id="450D5D910E6BBDFD984CFB63FD93FB3F" box="[558,613,1155,1171]" gridcol="2" gridrow="8" pageId="2" pageNumber="127">487.11</td>
<td id="450D5D910E6BBDFD98CFFB63FCFFFB3F" box="[685,777,1155,1171]" gridcol="3" gridrow="8" pageId="2" pageNumber="127">403.11</td>
<td id="450D5D910E6BBDFD9949FB63FC94FB3F" box="[811,866,1155,1171]" gridcol="4" gridrow="8" pageId="2" pageNumber="127">315.03</td>
<td id="450D5D910E6BBDFD99C8FB63FBB6FB3F" box="[938,1088,1155,1171]" gridcol="5" gridrow="8" pageId="2" pageNumber="127">C25H24O13</td>
<td id="450D5D910E6BBDFD9EE7FB63FA33FB3F" box="[1157,1477,1155,1171]" gridcol="6" gridrow="8" pageId="2" pageNumber="127">Isorhamnetin O-acetyl glucoside</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFB7AFA33FB06" box="[136,1477,1178,1194]" gridrow="9" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFB7AFEC2FB06" box="[136,308,1178,1194]" gridcol="0" gridrow="9" pageId="2" pageNumber="127">2.43</th>
<td id="450D5D910E6BBDFD9B1AFB7AFE1FFB06" box="[376,489,1178,1194]" gridcol="1" gridrow="9" pageId="2" pageNumber="127">563.11</td>
<td id="450D5D910E6BBDFD984CFB7AFD93FB06" box="[558,613,1178,1194]" gridcol="2" gridrow="9" pageId="2" pageNumber="127">519.02</td>
<td id="450D5D910E6BBDFD98CFFB7AFCFFFB06" box="[685,777,1178,1194]" gridcol="3" gridrow="9" pageId="2" pageNumber="127">487.13</td>
<td id="450D5D910E6BBDFD9949FB7AFC94FB06" box="[811,866,1178,1194]" gridcol="4" gridrow="9" pageId="2" pageNumber="127">403.11</td>
<td id="450D5D910E6BBDFD99C8FB7AFBB6FB06" box="[938,1088,1178,1194]" gridcol="5" gridrow="9" pageId="2" pageNumber="127">C25H23O15</td>
<td id="450D5D910E6BBDFD9EE7FB7AFA33FB06" box="[1157,1477,1178,1194]" gridcol="6" gridrow="9" pageId="2" pageNumber="127">Isorhamnetin O-malonyl glucoside</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFB50FA33FB6D" box="[136,1477,1200,1217]" gridrow="10" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFB50FEC2FB6D" box="[136,308,1200,1217]" gridcol="0" gridrow="10" pageId="2" pageNumber="127">2.94</th>
<td id="450D5D910E6BBDFD9B1AFB50FE1FFB6D" box="[376,489,1200,1217]" gridcol="1" gridrow="10" pageId="2" pageNumber="127">598.26</td>
<td id="450D5D910E6BBDFD984CFB50FD93FB6D" box="[558,613,1200,1217]" gridcol="2" gridrow="10" pageId="2" pageNumber="127">478.20</td>
<td id="450D5D910E6BBDFD98CFFB50FCFFFB6D" box="[685,777,1200,1217]" gridcol="3" gridrow="10" pageId="2" pageNumber="127">436.17</td>
<td id="450D5D910E6BBDFD9949FB50FC94FB6D" box="[811,866,1200,1217]" gridcol="4" gridrow="10" pageId="2" pageNumber="127">358.19</td>
<td id="450D5D910E6BBDFD99C8FB50FBB6FB6D" box="[938,1088,1200,1217]" gridcol="5" gridrow="10" pageId="2" pageNumber="127">C34H37N3O7</td>
<td id="450D5D910E6BBDFD9EE7FB50FA33FB6D" box="[1157,1477,1200,1217]" gridcol="6" gridrow="10" pageId="2" pageNumber="127">di Coumaroyl caffeoyl spermidine</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFB27FA33FB74" box="[136,1477,1223,1240]" gridrow="11" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFB27FEC2FB74" box="[136,308,1223,1240]" gridcol="0" gridrow="11" pageId="2" pageNumber="127">2.97</th>
<td id="450D5D910E6BBDFD9B1AFB27FE1FFB74" box="[376,489,1223,1240]" gridcol="1" gridrow="11" pageId="2" pageNumber="127">582.26</td>
<td id="450D5D910E6BBDFD984CFB27FD93FB74" box="[558,613,1223,1240]" gridcol="2" gridrow="11" pageId="2" pageNumber="127">462.22</td>
<td id="450D5D910E6BBDFD98CFFB27FCFFFB74" box="[685,777,1223,1240]" gridcol="3" gridrow="11" pageId="2" pageNumber="127">436.17</td>
<td id="450D5D910E6BBDFD9949FB27FC94FB74" box="[811,866,1223,1240]" gridcol="4" gridrow="11" pageId="2" pageNumber="127">342.16</td>
<td id="450D5D910E6BBDFD99C8FB27FBB6FB74" box="[938,1088,1223,1240]" gridcol="5" gridrow="11" pageId="2" pageNumber="127">C34H37N3O6</td>
<td id="450D5D910E6BBDFD9EE7FB27FA33FB74" box="[1157,1477,1223,1240]" gridcol="6" gridrow="11" pageId="2" pageNumber="127">tri-p-Coumaroyl spermidine</td>
</tr>
<tr id="06DC34ED0E6BBDFD9AEAFB3EFA33FB43" box="[136,1477,1246,1263]" gridrow="12" pageId="2" pageNumber="127">
<th id="450D5D910E6BBDFD9AEAFB3EFEC2FB43" box="[136,308,1246,1263]" gridcol="0" gridrow="12" pageId="2" pageNumber="127">3.03</th>
<td id="450D5D910E6BBDFD9B1AFB3EFE1FFB43" box="[376,489,1246,1263]" gridcol="1" gridrow="12" pageId="2" pageNumber="127">787.36</td>
<td id="450D5D910E6BBDFD984CFB3EFD93FB43" box="[558,613,1246,1263]" gridcol="2" gridrow="12" pageId="2" pageNumber="127">477.20</td>
<td id="450D5D910E6BBDFD98CFFB3EFCFFFB43" box="[685,777,1246,1263]" gridcol="3" gridrow="12" pageId="2" pageNumber="127">374.06</td>
<td id="450D5D910E6BBDFD9949FB3EFC94FB43" box="[811,866,1246,1263]" gridcol="4" gridrow="12" pageId="2" pageNumber="127">315.20</td>
<td id="450D5D910E6BBDFD99C8FB3EFBB6FB43" box="[938,1088,1246,1263]" gridcol="5" gridrow="12" pageId="2" pageNumber="127">C36H47O19</td>
<td id="450D5D910E6BBDFD9EE7FB3EFA33FB43" box="[1157,1477,1246,1263]" gridcol="6" gridrow="12" pageId="2" pageNumber="127">Isorhamnetin rutinosyl glucoside</td>
</tr>
</table>
</paragraph>
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<emphasis id="8A98EABD0E6B42009A13F920FF53F962" bold="true" box="[113,165,1728,1742]" pageId="2" pageNumber="127">Fig. 2.</emphasis>
(A) Relative free radical scavenging activity of 
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<emphasis id="8A98EABD0E6B42009850F95FFD5BF962" box="[562,685,1727,1742]" italics="true" pageId="2" pageNumber="127">A. artemisiifolia</emphasis>
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L. pollen and sub-pollen particles (SPP) aqueous extracts according to DPPH assay (
<emphasis id="8A98EABD0E6B42009F09F95FFA83F962" box="[1387,1397,1727,1742]" italics="true" pageId="2" pageNumber="127">p</emphasis>
&lt;0.001). (B) Antioxidative activity of 
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<emphasis id="8A98EABD0E6B42009B5AF936FE47F949" box="[312,433,1750,1765]" italics="true" pageId="2" pageNumber="127">A. artemisiifolia</emphasis>
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L. pollen and sub-pollen particles (SPP) aqueous extracts according to ABTS+ assay (
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&lt;0.001). ABTS assay showed similar results to the DPPH assay, with SPP extract exhibiting significantly diminished activity.
</paragraph>
</caption>
<paragraph id="B85336AF0E6B42009AF3F8C4FD48F873" blockId="2.[113,783,1827,2015]" pageId="2" pageNumber="127">
In addition to the aglycone (Y 
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<emphasis id="8A98EABD0E6B42009BA0F8C3FE25F89B" box="[450,467,1827,1847]" italics="true" pageId="2" pageNumber="127">—</emphasis>
) fragment, an abundant radical aglycone [Y 
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] 
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</emphasis>
. product ion is also formed, indicating a loss of 3- O-glucosyl fragment (all fragments with 
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/ 
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of aglycone 285, 301, 315 accompanied by ions at masses 284, 300, 314), further proving that mostly 3-O-glycosilated fragments are present in the mixture (
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). Fragmentation of the flavonol derivative quercetin-3-glucoside-3-malonate is shown in 
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.
</paragraph>
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The abundance ratio of the radical aglycone to the regular aglycone product ion originating from cleavage at the 3- 
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glycosidic bond increases with increasing OH substitution on the B-ring, whereas the opposite holds for 7-O-glycosides (
<bibRefCitation id="DC7D4B5E0E6B42009F32F898FC87F80B" author="March, R. E. &amp; Lewars, E. G. &amp; Stadey, C. J. &amp; Miao, X. - S. &amp; Zhao, X. &amp; Metcalfe, C. D." pageId="2" pageNumber="127" pagination="61 - 85" refId="ref7269" refString="March, R. E., Lewars, E. G., Stadey, C. J., Miao, X. - S., Zhao, X., Metcalfe, C. D., 2006. A comparison of flavonoid glycosides by electrospray tandem mass spectrometry. Int. J. Mass Spectrom. 248, 61 - 85." type="journal article" year="2006">March et al., 2006</bibRefCitation>
). This phenomenon can be observed when comparing kaempferol and quercetin derivatives (peaks at retention time (RT) 1.72 and 2.09, as well as 1.89 and 2.09). Aglycone identities were confirmed by following 
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and 
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fragments present in the 
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spectra. Both quercetin and isorhamnetin can produce 
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fragment with 
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/ 
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of 
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negative mode, in a reaction that proceeds via retro Diels–Alder mechanism (RDA). These compounds were distinguished according to their molecular ions and Y 
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<emphasis id="8A98EABD0E6A42019AF8FA10FF5DF9A8" box="[154,171,1520,1540]" italics="true" pageId="3" pageNumber="128">—</emphasis>
2 
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<emphasis id="8A98EABD0E6A42019AAAFA10FF2FF9A8" box="[200,217,1520,1540]" italics="true" pageId="3" pageNumber="128">—</emphasis>
CO ions.
</paragraph>
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<emphasis id="8A98EABD0E6A42019AB9FC0BFEFBFC55" bold="true" box="[219,269,1003,1017]" pageId="3" pageNumber="128">Fig. 3.</emphasis>
Base peak chromatogram of the 
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<emphasis id="8A98EABD0E6A4201987FFC0AFD61FC55" box="[541,663,1002,1017]" italics="true" pageId="3" pageNumber="128">A. artemisiifolia</emphasis>
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L. aqueous pollen extract analysed on UHPLC/ESI-LTQ-Orbitrap mass spectrometer.
</paragraph>
</caption>
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<emphasis id="8A98EABD0E6A42019B63FADAFEC5FAE4" bold="true" box="[257,307,1338,1352]" pageId="3" pageNumber="128">Fig. 4.</emphasis>
Main aglycones detected in the 
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<emphasis id="8A98EABD0E6A42019822FAD9FD4FFAE4" box="[576,697,1337,1352]" italics="true" pageId="3" pageNumber="128">A. artemisiifolia</emphasis>
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L. aqueous pollen extract. (A) quercetin, (B) kaempferol, (C) isorhamnetin.
</paragraph>
</caption>
<paragraph id="B85336AF0E6A42019A14F9EDFD91F9D8" blockId="3.[87,757,1378,1652]" pageId="3" pageNumber="128">
Compounds having a methoxy substituent show relatively weaker RDA fragmentation, observable when comparing the fragmentation spectra of quercetin and isorhamnetin derivatives (RT 2.2 and 2.21, 1.72 and 1.93) (
<bibRefCitation id="DC7D4B5E0E6A42019BC9F981FDACF9D8" author="Fabre, N. &amp; Rustan, I. &amp; de Hoffmann, E. &amp; Quetin-Leclercq, J." box="[427,602,1633,1652]" pageId="3" pageNumber="128" pagination="707 - 715" refId="ref6381" refString="Fabre, N., Rustan, I., de Hoffmann, E., Quetin-Leclercq, J., 2001. Determination of flavone, flavonol, and flavanone aglycones by negative ion liquid chromatography electrospray ion trap mass spectrometry. J. Am. Soc. Mass Spectrom. 12, 707 - 715." type="journal article" year="2001">Fabre et al., 2001</bibRefCitation>
).
</paragraph>
<paragraph id="B85336AF0E6A42019A35F978FD19F900" blockId="3.[87,751,1688,1708]" box="[87,751,1688,1708]" pageId="3" pageNumber="128">
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<emphasis id="8A98EABD0E6A42019A35F978FD19F900" box="[87,751,1688,1708]" italics="true" pageId="3" pageNumber="128">
2.4. Spermidine derivatives in the pollen extract of 
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L
</emphasis>
</heading>
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<paragraph id="B85336AF0E6A42019A14F930FE62F80B" blockId="3.[87,757,1744,2015]" pageId="3" pageNumber="128">
Phenolamides constitute a diverse and quantitatively major group of secondary metabolites resulting from the conjugation of a phenolic moiety with polyamides, such as spermidine (
<bibRefCitation id="DC7D4B5E0E6A420198CAF8E8FF25F89B" author="Bassard, J. - E. &amp; Ullmann, P. &amp; Bernier, F. &amp; Werck-Reichhart, D." pageId="3" pageNumber="128" pagination="1808 - 1824" refId="ref6254" refString="Bassard, J. - E., Ullmann, P., Bernier, F., Werck-Reichhart, D., 2010. Phenolamides: bridging polyamines to the phenolic metabolism. Phytochemistry 71, 1808 - 1824." type="journal article" year="2010">Bassard et al., 2010</bibRefCitation>
). Several spermidine amide derivatives have been detected in the 
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<emphasis id="8A98EABD0E6A42019B66F8DFFE56F8FF" box="[260,416,1855,1875]" italics="true" pageId="3" pageNumber="128">A. artemisiifolia</emphasis>
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L. pollen extract. Among them, the most prominent were di-coumaroyl-caffeoyl and tri-coumaroyl containing compounds. Fragmentation patterns for spermidine derivatives are shown in 
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.
</paragraph>
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Peak at retention time 2.93, with 
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/ 
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of the [M 
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H] 
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ion of 598.2573 showed characteristic fragmentation pattern (
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) with fragments at 
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/ 
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478, attributed to the loss of 120 Da fragment from 
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-coumaric residue ([M 
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H] 
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HO 
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C6 
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H4 
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), 
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/ 
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436 (loss of coumaroyl residue) and 
<emphasis id="8A98EABD0E6A42019F0FFA7CFA76FA1C" box="[1389,1408,1436,1456]" italics="true" pageId="3" pageNumber="128">m</emphasis>
/ 
<emphasis id="8A98EABD0E6A42019FEAFA7CFA64FA1C" box="[1416,1426,1436,1456]" italics="true" pageId="3" pageNumber="128">z</emphasis>
358 (loss of 120 Da fragment at N 
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and breakage of C 
<emphasis id="8A98EABD0E6A42019F41FA5BFAC3FA60" bold="true" box="[1315,1333,1467,1484]" pageId="3" pageNumber="128">A</emphasis>
C bond of the caffeoyl residue linked at N 
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). The compound was identified as di-coumaroyl caffeoyl spermidine.
</paragraph>
<paragraph id="B85336AF0E6A42019926F9EDFB14F900" blockId="3.[805,1475,1381,2015]" pageId="3" pageNumber="128">
Observed masses can be explained by formation of homolytic cleavage/deprotonation products during fragmentation. Few papers have been published so far regarding the fragmentation of polyamide phenolics (
<bibRefCitation id="DC7D4B5E0E6A42019E64F981FAD7F9D8" author="Narvaez-Cuenca, C. E. &amp; Vincken, J. P. &amp; Zheng, C. &amp; Gruppen, H." box="[1030,1313,1633,1652]" pageId="3" pageNumber="128" pagination="1087 - 1097" refId="ref7336" refString="Narvaez-Cuenca, C. E., Vincken, J. P., Zheng, C., Gruppen, H., 2013. Diversity of (dihydro) hydroxycinnamic acid conjugates in Colombian potato tubers. Food Chem. 139, 1087 - 1097." type="journal article" year="2013">Narvaez-Cuenca et al., 2013</bibRefCitation>
). To the best of our knowledge, formation of radical products of spermidine derivatives in MS 
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has not been described so far.
</paragraph>
<paragraph id="B85336AF0E6A42019926F954FA63F8C3" blockId="3.[805,1475,1381,2015]" pageId="3" pageNumber="128">
Similarly, at 2.96 min retention time, a peak with 
<emphasis id="8A98EABD0E6A42019F1EF953FA79F96B" box="[1404,1423,1715,1735]" italics="true" pageId="3" pageNumber="128">m</emphasis>
/ 
<emphasis id="8A98EABD0E6A42019FF4F953FA56F96B" box="[1430,1440,1715,1735]" italics="true" pageId="3" pageNumber="128">z</emphasis>
of 582.262 for the [M 
<emphasis id="8A98EABD0E6A42019991F92FFBF2F94F" box="[1011,1028,1743,1763]" italics="true" pageId="3" pageNumber="128">—</emphasis>
H] 
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</emphasis>
ion, with corresponding fragments in MS 
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at 
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/ 
<emphasis id="8A98EABD0E6A420199E9F90BFC63F953" box="[907,917,1771,1791]" italics="true" pageId="3" pageNumber="128">z</emphasis>
462, 436 and 358 has identical fragmentation mechanism as for the previous compound, with the only 16 Da difference for the 
<emphasis id="8A98EABD0E6A4201990CF8C3FC77F89B" box="[878,897,1827,1847]" italics="true" pageId="3" pageNumber="128">m</emphasis>
/ 
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462 and 
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/ 
<emphasis id="8A98EABD0E6A42019E6EF8C3FBE0F89B" box="[1036,1046,1827,1847]" italics="true" pageId="3" pageNumber="128">z</emphasis>
436 fragments. The difference stems from the replacement of a caffeoyl residue with a coumaroyl residue. The compound was identified as tri- 
<emphasis id="8A98EABD0E6A42019EF4F8BBFB54F8C3" box="[1174,1186,1883,1903]" italics="true" pageId="3" pageNumber="128">p</emphasis>
-coumaroyl spermidine.
</paragraph>
<paragraph id="B85336AF0E6A42069926F898FDD6F98C" blockId="3.[805,1475,1381,2015]" lastBlockId="4.[113,783,1242,1708]" lastPageId="4" lastPageNumber="129" pageId="3" pageNumber="128">
Spermidine and other polyamide compounds are widely present in all organisms, known to affect many processes, in both plants (
<bibRefCitation id="DC7D4B5E0E6A42019910F850FBC4F86F" author="Falasca, G. &amp; Franceschetti, M. &amp; Bagni, N. &amp; Altamura, M. M. &amp; Biasi, R." box="[882,1074,1968,1987]" pageId="3" pageNumber="128" pagination="565 - 573" refId="ref6439" refString="Falasca, G., Franceschetti, M., Bagni, N., Altamura, M. M., Biasi, R., 2010. Polyamine biosynthesis and control of the development of functional pollen in kiwifruit. Plant Physiol. Biochem. 48, 565 - 573." type="journal article" year="2010">Falasca et al., 2010</bibRefCitation>
), and animals (
<bibRefCitation id="DC7D4B5E0E6A42019EB0F850FCA1F873" author="Igarashi, K. &amp; Kashiwagi, K." pageId="3" pageNumber="128" pagination="39 - 51" refId="ref6908" refString="Igarashi, K., Kashiwagi, K., 2010. Modulation of cellular function by polyamines. Int. J. Biochem. Cell Biol. 42, 39 - 51." type="journal article" year="2010">Igarashi and Kashiwagi, 2010</bibRefCitation>
). They have been shown to function naturally as free radical et al., 2006). UHPLC/ESI-MS–MS analysis was conducted on the Orbitrap instrument, using the same method as the one used for whole pollen analysis. The results show that flavonoid- 
<emphasis id="8A98EABD0E6D42069FE5FF0DFA60FEAD" box="[1415,1430,237,257]" italics="true" pageId="4" pageNumber="129">O</emphasis>
-glycosides are the principal components of SPP phenolic fraction in 
<taxonomicName id="7FEC4D2C0E6D42069FA8FEE9FC4BFE95" class="Magnoliopsida" family="Asteraceae" genus="Ambrosia" kingdom="Plantae" order="Asterales" pageId="4" pageNumber="129" phylum="Tracheophyta" rank="species" species="artemisiifolia">
<emphasis id="8A98EABD0E6D42069FA8FEE9FC4BFE95" italics="true" pageId="4" pageNumber="129">A. artemisiifolia</emphasis>
</taxonomicName>
L. (
<tableCitation id="F56E03140E6D42069981FEC6FBDBFE95" box="[995,1069,294,313]" captionStart="Table 2" captionStartId="2.[114,158,900,914]" captionTargetPageId="2" captionText="Table 2 Compounds detected in A. artemisiifolia L. sub-pollen particle aqueous extract on the UHPLC/ESI-Orbitrap mass spectrometer." pageId="4" pageNumber="129">Table 2</tableCitation>
). Compared to the whole pollen phenolics composition, SPP exhibit similar composition but with lower total phenolic amount and lack of the small phenolic molecules, below 450 Da, that are extensively present in pollen. Main components are monoglycoside derivatives of isorhamnetin and quercetin, with characteristic fragmentation patterns (
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A 
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and 
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B 
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fragments) (
<tableCitation id="F56E03140E6D42069925FE2DFC66FE4C" box="[839,912,461,480]" captionStart="Table 2" captionStartId="2.[114,158,900,914]" captionTargetPageId="2" captionText="Table 2 Compounds detected in A. artemisiifolia L. sub-pollen particle aqueous extract on the UHPLC/ESI-Orbitrap mass spectrometer." pageId="4" pageNumber="129">Table 2</tableCitation>
). Di-glycosides of isorhamnetin found in the whole pollen extract haven’t been detected and this could be due to the mode of their formation from pollen cytoplasm. Spermidine derivatives are present, with implications regarding the immunomodulatory effects they could exert. scavengers (
<bibRefCitation id="DC7D4B5E0E6D42069A8FFB3AFE8DFB41" author="Ha, H. C. &amp; Yager, J. D. &amp; Woster, P. A. &amp; Casero Jr., R. A." box="[237,379,1242,1261]" pageId="4" pageNumber="129" pagination="298 - 303" refId="ref6716" refString="Ha, H. C., Yager, J. D., Woster, P. A., Casero Jr., R. A., 1998. Structural specificity of polyamines and polyamine analogues in the protection of DNA from strand breaks induced by reactive oxygen species. Biochem. Biophys. Res. Commun. 244, 298 - 303." type="journal article" year="1998">Ha et al., 1998</bibRefCitation>
). Spermidine acyl derivatives such as its amides have already been reported in pollen (
<bibRefCitation id="DC7D4B5E0E6D42069826FB16FCFDFAA5" author="Bassard, J. - E. &amp; Ullmann, P. &amp; Bernier, F. &amp; Werck-Reichhart, D." box="[580,779,1270,1289]" pageId="4" pageNumber="129" pagination="1808 - 1824" refId="ref6254" refString="Bassard, J. - E., Ullmann, P., Bernier, F., Werck-Reichhart, D., 2010. Phenolamides: bridging polyamines to the phenolic metabolism. Phytochemistry 71, 1808 - 1824." type="journal article" year="2010">Bassard et al., 2010</bibRefCitation>
; 
<bibRefCitation id="DC7D4B5E0E6D42069A13FAF2FEE7FA89" author="Kite, G. C. &amp; Larsson, S. &amp; Veitch, N. C. &amp; Porter, E. A. &amp; Ding, N. &amp; Simmonds, M. S." box="[113,273,1298,1317]" pageId="4" pageNumber="129" pagination="3501 - 3508" refId="ref7095" refString="Kite, G. C., Larsson, S., Veitch, N. C., Porter, E. A., Ding, N., Simmonds, M. S., 2013. Acyl spermidines in inflorescence extracts of elder (Sambucus nigra L., Adoxaceae) and elderflower drinks. J. Agric. Food Chem. 61, 3501 - 3508." type="journal article" year="2013">Kite et al., 2013</bibRefCitation>
). Recently, polyamides were reviewed by 
<bibRefCitation id="DC7D4B5E0E6D420698A0FAF2FEF3FAED" author="Bassard, J. - E. &amp; Ullmann, P. &amp; Bernier, F. &amp; Werck-Reichhart, D." pageId="4" pageNumber="129" pagination="1808 - 1824" refId="ref6254" refString="Bassard, J. - E., Ullmann, P., Bernier, F., Werck-Reichhart, D., 2010. Phenolamides: bridging polyamines to the phenolic metabolism. Phytochemistry 71, 1808 - 1824." type="journal article" year="2010">Bassard et al. (2010)</bibRefCitation>
, who concluded that di- and tri-substituted hydroxy-cinnamoyl conjugates, particularly of spermidine and putrescine, are major metabolites of pollen and suggested to have an ecological role as defense compounds against viruses, bacteria, and fungi, and could deter herbivores from eating plants. The spermidine conjugates are implicated in protection against pathogens, detoxifying phenolic compounds, and/or serving as a reserve of polyamines that are available to actively proliferating tissues, although not always essential for survival.
</paragraph>
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<paragraph id="B85336AF0E6D42069AFBFB48FD1FFB1A" blockId="4.[153,745,1192,1206]" box="[153,745,1192,1206]" pageId="4" pageNumber="129">
<emphasis id="8A98EABD0E6D42069AFBFB48FF3DFB1A" bold="true" box="[153,203,1192,1206]" pageId="4" pageNumber="129">Fig. 5.</emphasis>
Fragmentation pattern of quercetin-3-O-(3-O-malonyl) glycoside.
</paragraph>
</caption>
<paragraph id="B85336AF0E6D42069AF3F9C9FF18F907" blockId="4.[113,783,1242,1708]" pageId="4" pageNumber="129">
In addition, polyamides and their derivatives play a regulatory role in several immunologic processes, including allergic reactions (
<bibRefCitation id="DC7D4B5E0E6D42069A18F980FEDBF9D8" author="Bueb, J. L. &amp; Mousli, M. &amp; Landry, Y." box="[122,301,1632,1652]" pageId="4" pageNumber="129" pagination="84 - 87" refId="ref6295" refString="Bueb, J. L., Mousli, M., Landry, Y., 1991. Molecular basis for cellular effects of naturally occurring polyamines. Agents Actions 33, 84 - 87." type="journal article" year="1991">Bueb et al., 1991</bibRefCitation>
; 
<bibRefCitation id="DC7D4B5E0E6D42069B59F981FDC5F9D8" author="Hoet, P. H. &amp; Nemery, B." box="[315,563,1632,1652]" pageId="4" pageNumber="129" pagination="433" refId="ref6818" refString="Hoet, P. H., Nemery, B., 2000. Polyamines in the lung: polyamine uptake and polyamine-linked pathological or toxicological conditions. Am. J. Physiol. Lung Cell. Mol. Physiol. 278, L 417 - L 433." type="journal article" year="2000">Hoet and Nemery, 2000</bibRefCitation>
), regulation of T cell function, cell migration and growth in local inflammation (
<bibRefCitation id="DC7D4B5E0E6D420698B2F99CFF17F907" author="Ferioli, M. E. &amp; Pirona, L. &amp; Pinotti, O." pageId="4" pageNumber="129" pagination="51 - 56" refId="ref6492" refString="Ferioli, M. E., Pirona, L., Pinotti, O., 2000. Prolactin and polyamine catabolism: specific effect on polyamine oxidase activity in rat thymus. Mol. Cell. Endocrinol. 165, 51 - 56." type="journal article" year="2000">Ferioli et al., 2000</bibRefCitation>
).
</paragraph>
</subSubSection>
</treatment>
</document>