918 lines
126 KiB
XML
918 lines
126 KiB
XML
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<mods:title id="113B19DA38C768041B1ABC8CA668CDBE">Secondary metabolites of the lichen Hypogymnia physodes (L.) Nyl. and their presence in spruce (Picea abies (L.) H. Karst.) bark</mods:title>
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<mods:namePart id="731B6A1B8B2CF55CDE67281ED4F682A9">Latkowska, Ewa</mods:namePart>
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<mods:namePart id="B12F9B93FFC8C58FE9A2035DEF173ADC">Bober, Beata</mods:namePart>
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<mods:namePart id="E2A5CF1542002D716837120E2E3E73F1">Chrapusta, Ewelina</mods:namePart>
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<mods:namePart id="604C570BBCD71C74B0D42290770E9299">Adamski, Michal</mods:namePart>
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<mods:namePart id="F1E5AF5A658CEFA1B5D65A6AEC20AB32">Kaminski, Ariel</mods:namePart>
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<mods:namePart id="0C7AB2507F3D499196BB8FCE09C19F66">Bialczyk, Jan</mods:namePart>
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<mods:title id="A1AB8A8DD78B6F69D2973029CAB810C4">Phytochemistry</mods:title>
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<heading id="8E309441C910FFEC2572F99DFCBD8A07" box="[114,783,1632,1652]" centered="true" fontSize="36" level="2" pageId="1" pageNumber="117" reason="3">
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<emphasis id="E7B3FF3FC910FFEC2572F99DFCBD8A07" box="[114,783,1632,1652]" italics="true" pageId="1" pageNumber="117">
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2.1. Qualitative determination of secondary metabolites in
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<taxonomicName id="12C758AEC910FFEC279FF99DFD6A8A07" ID-CoL="6MR42" authority="(L.) Nyl." authorityName="Nyl." baseAuthorityName="L." box="[671,728,1632,1652]" class="Lecanoromycetes" family="Parmeliaceae" genus="Hypogymnia" kingdom="Fungi" order="Lecanorales" pageId="1" pageNumber="117" phylum="Ascomycota" rank="species" species="physodes">lichen</taxonomicName>
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thalli
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<paragraph id="D578232DC910FFEC2591F964FBD88811" blockId="1.[113,783,1688,2015]" lastBlockId="1.[831,1501,182,2015]" pageId="1" pageNumber="117">
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Ten compounds (hp1–hp10) were isolated from
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<emphasis id="E7B3FF3FC910FFEC2797F965FCBC8ADF" box="[663,782,1688,1708]" italics="true" pageId="1" pageNumber="117">H. physodes</emphasis>
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thalli during the
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–
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/
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procedure (
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). The first three compounds (hp1–hp3) showed absorption maxima in the range of
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,
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and
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(
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), which are characteristic ranges for depsidones of the
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<emphasis id="E7B3FF3FC910FFEC274AF8F5FDE48B68" bold="true" box="[586,598,1800,1819]" italics="true" pageId="1" pageNumber="117">β</emphasis>
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-orcinol-type with an aldehyde or a hydroxymethyl group at position
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(
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) in the aromatic ring on the left-hand side (A-ring) of the molecule (
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). The mass spectra in negative ion mode displayed deprotonated molecules [M
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</emphasis>
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that were detected at
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<emphasis id="E7B3FF3FC910FFEC25EFF86EFEB08BD4" box="[239,258,1939,1959]" italics="true" pageId="1" pageNumber="117">m</emphasis>
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/
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<emphasis id="E7B3FF3FC910FFEC2409F86EFEA18BD4" box="[265,275,1939,1959]" italics="true" pageId="1" pageNumber="117">z</emphasis>
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417, 373 and 415 for compounds hp1, hp2 and hp3, respectively (
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). A detailed analysis of the
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/
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spectra revealed that the most intense peaks of the product ions were formed due to the loss of small molecules (
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,
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or OCH
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) from the parent and daughter ions (Suppl.
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<figureCitation id="4DFC3FA8C910FFEC2063FF2FFA7D8C96" box="[1379,1487,210,229]" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="1" pageNumber="117">Fig. S1A–C</figureCitation>
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). The proposed scheme of the fragmentation pathways is presented in
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<figureCitation id="4DFC3FA8C910FFEC2658FEF7FC3C8D6E" box="[856,910,266,285]" captionStart="Fig" captionStartId="3.[209,235,1499,1513]" captionTargetBox="[287,1324,184,1469]" captionTargetId="graphics-370@3.[353,1209,280,1212]" captionTargetPageId="3" captionText="Fig. 2. Proposed scheme of fragmentation pathways of compounds: hp1 – conphysodalic acid; hp2 – protocetraric acid and hp3 – physodalic acid." figureDoi="http://doi.org/10.5281/zenodo.10488553" httpUri="https://zenodo.org/record/10488553/files/figure.png" pageId="1" pageNumber="117">Fig. 2</figureCitation>
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. The loss of
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<collectionCode id="B3D6BBE8C910FFEC212FFEF7FBDE8D6E" box="[1071,1132,266,285]" pageId="1" pageNumber="117">COOH</collectionCode>
|
||
groups from the parent ions of compounds hp1 and hp3 formed the product ions observed at
|
||
<emphasis id="E7B3FF3FC910FFEC208BFED8FA2C8D4A" box="[1419,1438,293,313]" italics="true" pageId="1" pageNumber="117">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC910FFEC20A6FED8FA028D4A" box="[1446,1456,293,313]" italics="true" pageId="1" pageNumber="117">z</emphasis>
|
||
357 and 355, respectively. Further loss of one and two
|
||
<collectionCode id="B3D6BBE8C910FFEC2036FEBFFAE18D26" box="[1334,1363,322,341]" country="France" lsid="urn:lsid:biocol.org:col:13662" name="Museum National d'Histoire Naturelle" pageId="1" pageNumber="117" type="Herbarium">CO</collectionCode>
|
||
<subScript id="49432168C910FFEC2052FEB6FAE98D24" attach="left" box="[1362,1371,331,343]" fontSize="5" pageId="1" pageNumber="117">2</subScript>
|
||
groups from the ion at
|
||
<emphasis id="E7B3FF3FC910FFEC26A5FEA0FC0A8D02" box="[933,952,349,369]" italics="true" pageId="1" pageNumber="117">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC910FFEC26C0FEA0FC788D02" box="[960,970,349,369]" italics="true" pageId="1" pageNumber="117">z</emphasis>
|
||
357 (hp1) led to ions at
|
||
<emphasis id="E7B3FF3FC910FFEC21C1FEA0FB668D02" box="[1217,1236,349,369]" italics="true" pageId="1" pageNumber="117">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC910FFEC21DCFEA0FB548D02" box="[1244,1254,349,369]" italics="true" pageId="1" pageNumber="117">z</emphasis>
|
||
313 and 269. The corresponding ion fragments for compound hp3 were observed at
|
||
<emphasis id="E7B3FF3FC910FFEC20B8FE85FA798DFF" box="[1464,1483,376,396]" italics="true" pageId="1" pageNumber="117">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC910FFEC20D2FE85FA6E8DFF" box="[1490,1500,376,396]" italics="true" pageId="1" pageNumber="117">z</emphasis>
|
||
311 and 267, respectively. Additional elimination of the
|
||
<collectionCode id="B3D6BBE8C910FFEC2072FE6BFA308DDA" box="[1394,1410,406,425]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="1" pageNumber="117" type="Herbarium">H</collectionCode>
|
||
<subScript id="49432168C910FFEC2082FE63FA398DD9" attach="both" box="[1410,1419,414,426]" fontSize="5" pageId="1" pageNumber="117">2</subScript>
|
||
<collectionCode id="B3D6BBE8C910FFEC208CFE6BFA2E8DDA" box="[1420,1436,406,425]" country="Norway" lsid="urn:lsid:biocol.org:col:13093" name="Botanical Museum - University of Oslo" pageId="1" pageNumber="117" type="Herbarium">O</collectionCode>
|
||
molecule from the product ion at
|
||
<emphasis id="E7B3FF3FC910FFEC216EFE4DFB338DB7" box="[1134,1153,432,452]" italics="true" pageId="1" pageNumber="117">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC910FFEC2189FE4DFB218DB7" box="[1161,1171,432,452]" italics="true" pageId="1" pageNumber="117">z</emphasis>
|
||
269 (hp1) yielded the ion fragment at
|
||
<emphasis id="E7B3FF3FC910FFEC2699FE31FC1E8D93" box="[921,940,460,480]" italics="true" pageId="1" pageNumber="117">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC910FFEC26B4FE31FC0C8D93" box="[948,958,460,480]" italics="true" pageId="1" pageNumber="117">z</emphasis>
|
||
251. The loss of all of the above-mentioned groups in an alternative sequence resulted in the following fragments in the mass spectrum of compound hp1:
|
||
<emphasis id="E7B3FF3FC910FFEC21E0FDF9FB418E6B" box="[1248,1267,516,536]" italics="true" pageId="1" pageNumber="117">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC910FFEC21FAFDF9FAB68E6B" box="[1274,1284,516,536]" italics="true" pageId="1" pageNumber="117">z</emphasis>
|
||
399, 355, 339, 311, 295 and 251. It is worth noting that both compounds hp1 and hp3 have a partially coincident fragmentation pattern (
|
||
<figureCitation id="4DFC3FA8C910FFEC207BFDC0FA018E23" box="[1403,1459,573,592]" captionStart="Fig" captionStartId="3.[209,235,1499,1513]" captionTargetBox="[287,1324,184,1469]" captionTargetId="graphics-370@3.[353,1209,280,1212]" captionTargetPageId="3" captionText="Fig. 2. Proposed scheme of fragmentation pathways of compounds: hp1 – conphysodalic acid; hp2 – protocetraric acid and hp3 – physodalic acid." figureDoi="http://doi.org/10.5281/zenodo.10488553" httpUri="https://zenodo.org/record/10488553/files/figure.png" pageId="1" pageNumber="117">Fig. 2</figureCitation>
|
||
). In addition, the product ions at
|
||
<emphasis id="E7B3FF3FC910FFEC2177FDA5FB388E1F" box="[1143,1162,600,620]" italics="true" pageId="1" pageNumber="117">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC910FFEC2192FDA5FB2E8E1F" box="[1170,1180,600,620]" italics="true" pageId="1" pageNumber="117">z</emphasis>
|
||
311 and 267 are likely structurally equivalent with hp2 and hp3 (Suppl.
|
||
<figureCitation id="4DFC3FA8C910FFEC201AFD88FA348EFB" box="[1306,1414,629,648]" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="1" pageNumber="117">Fig. S1B–C</figureCitation>
|
||
). In the lower
|
||
<emphasis id="E7B3FF3FC910FFEC2683FD72FC248ED0" box="[899,918,655,675]" italics="true" pageId="1" pageNumber="117">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC910FFEC269EFD72FC1A8ED0" box="[926,936,655,675]" italics="true" pageId="1" pageNumber="117">z</emphasis>
|
||
range of the
|
||
<collectionCode id="B3D6BBE8C910FFEC2140FD6CFBD28ED7" box="[1088,1120,657,676]" country="Italy" lsid="urn:lsid:biocol.org:col:14396" name="Herbarium Messanaensis, Università di Messina" pageId="1" pageNumber="117" type="Herbarium">MS</collectionCode>
|
||
/
|
||
<collectionCode id="B3D6BBE8C910FFEC2168FD6CFB3A8ED7" box="[1128,1160,657,676]" country="Italy" lsid="urn:lsid:biocol.org:col:14396" name="Herbarium Messanaensis, Università di Messina" pageId="1" pageNumber="117" type="Herbarium">MS</collectionCode>
|
||
spectra of compounds hp2 and hp3, daughter ions at
|
||
<emphasis id="E7B3FF3FC910FFEC211BFD56FB9C8ECC" box="[1051,1070,683,703]" italics="true" pageId="1" pageNumber="117">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC910FFEC2136FD56FBF28ECC" box="[1078,1088,683,703]" italics="true" pageId="1" pageNumber="117">z</emphasis>
|
||
151 and 177 derived from typical A-ring fragmentation were observed (Suppl.
|
||
<figureCitation id="4DFC3FA8C910FFEC21B9FD35FB4B8EA8" box="[1209,1273,712,731]" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="1" pageNumber="117">Fig. S1</figureCitation>
|
||
). Most of the obtained fragments from hp2 (Suppl.
|
||
<figureCitation id="4DFC3FA8C910FFEC2164FD19FB068E84" box="[1124,1204,740,759]" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="1" pageNumber="117">Fig. S1B</figureCitation>
|
||
) corresponded to those presented previously by
|
||
<bibRefCitation id="B1565EDCC910FFEC2119FCFDFB5A8F60" author="Huneck, S. & Feige, G. B. & Schmidt, J." box="[1049,1256,768,788]" pageId="1" pageNumber="117" pagination="51 - 58" refId="ref8053" refString="Huneck, S., Feige, G. B., Schmidt, J., 2004. Chemie von Cladonia furcata und Cladonia rangiformis. Herzogia 17, 51 - 58." type="journal article" year="2004">Huneck et al. (2004)</bibRefCitation>
|
||
and
|
||
<bibRefCitation id="B1565EDCC910FFEC201CFCFCFA6E8F60" author="Parrot, D. & Jan, S. & Baert, N. & Guyot, S. & Tomasi, S." box="[1308,1500,768,788]" pageId="1" pageNumber="117" pagination="114 - 124" refId="ref8788" refString="Parrot, D., Jan, S., Baert, N., Guyot, S., Tomasi, S., 2013. Comparative metabolite profiling and chemical study of Ramalina siliquosa complex using LC - ESI-MS / MS approach. Phytochemistry 89, 114 - 124." type="journal article" year="2013">Parrot et al. (2013)</bibRefCitation>
|
||
for protocetraric acid. The partial compatibility between compounds hp1–hp3 supported their structure similarities (
|
||
<bibRefCitation id="B1565EDCC910FFEC2090FCC5FBA98F14" author="Huneck, S. & Yoshimura, I." pageId="1" pageNumber="117" refId="ref8031" refString="Huneck, S., Yoshimura, I., 1996. Identification of Lichen Substances. Springer Verlag, Berlin." type="book" year="1996">Huneck and Yoshimura, 1996</bibRefCitation>
|
||
) and biosynthetic relationship (
|
||
<bibRefCitation id="B1565EDCC910FFEC2069FCA9FA7D8F14" author="Elix, J. A." box="[1385,1487,852,871]" pageId="1" pageNumber="117" refId="ref7613" refString="Elix, J. A., 2014. A Catalogue of Standardized Chromatographic Data and Biosynthetic Relationships for Lichen Substances, third ed. Canberra, Published by the author." type="book" year="2014">Elix, 2014</bibRefCitation>
|
||
). Based on the present data (
|
||
<tableCitation id="98451696C910FFEC2162FC8DFB1D8FF0" box="[1122,1199,880,899]" captionStart="Table 1" captionStartId="2.[87,131,728,742]" captionTargetPageId="2" captionText="Table 1 Chemical features of compounds isolated from H. physodes thalli. Retention times (R) from the UPLC analysis, UV absorption maxima (λ), molecular ion masses ([M—H] —), and t max relative retention factors (Rf) from the TLC analysis." httpUri="http://table.plazi.org/id/81B873A5C913FFEF2557FD25FE418F60" pageId="1" pageNumber="117" tableUuid="81B873A5C913FFEF2557FD25FE418F60">Table 1</tableCitation>
|
||
, Suppl.
|
||
<figureCitation id="4DFC3FA8C910FFEC2005FC8DFAC38FF0" box="[1285,1393,880,899]" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="1" pageNumber="117">Fig. S1A–C</figureCitation>
|
||
) and proposed scheme of fragmentation (
|
||
<figureCitation id="4DFC3FA8C910FFEC2199FC76FB618FEC" box="[1177,1235,907,927]" captionStart="Fig" captionStartId="3.[209,235,1499,1513]" captionTargetBox="[287,1324,184,1469]" captionTargetId="graphics-370@3.[353,1209,280,1212]" captionTargetPageId="3" captionText="Fig. 2. Proposed scheme of fragmentation pathways of compounds: hp1 – conphysodalic acid; hp2 – protocetraric acid and hp3 – physodalic acid." figureDoi="http://doi.org/10.5281/zenodo.10488553" httpUri="https://zenodo.org/record/10488553/files/figure.png" pageId="1" pageNumber="117">Fig. 2</figureCitation>
|
||
), they were identified as conphysodalic acid (hp1), protocetraric acid (hp2) and physodalic acid (hp3); all of these acids belong to the
|
||
<emphasis id="E7B3FF3FC910FFEC2002FC3EFABC8FA5" bold="true" box="[1282,1294,963,982]" italics="true" pageId="1" pageNumber="117">β</emphasis>
|
||
-orcinol depsidones. The identification of hp3 as physodalic acid was further confirmed by comparing its
|
||
<emphasis id="E7B3FF3FC910FFEC26F5FC07FBB58863" box="[1013,1031,1018,1040]" italics="true" pageId="1" pageNumber="117">
|
||
<subScript id="49432168C910FFEC26F5FC07FBB58863" attach="left" box="[1013,1031,1018,1040]" fontSize="5" pageId="1" pageNumber="117">Rf</subScript>
|
||
</emphasis>
|
||
value of the TLC analysis (
|
||
<tableCitation id="98451696C910FFEC2021FC06FADE887D" box="[1313,1388,1019,1038]" captionStart="Table 1" captionStartId="2.[87,131,728,742]" captionTargetPageId="2" captionText="Table 1 Chemical features of compounds isolated from H. physodes thalli. Retention times (R) from the UPLC analysis, UV absorption maxima (λ), molecular ion masses ([M—H] —), and t max relative retention factors (Rf) from the TLC analysis." httpUri="http://table.plazi.org/id/81B873A5C913FFEF2557FD25FE418F60" pageId="1" pageNumber="117" tableUuid="81B873A5C913FFEF2557FD25FE418F60">Table 1</tableCitation>
|
||
) with that described by
|
||
<bibRefCitation id="B1565EDCC910FFEC26C5FBEAFB3F8859" author="Orange, A. & James, P. W. & White, F. J." box="[965,1165,1047,1066]" pageId="1" pageNumber="117" refId="ref8753" refString="Orange, A., James, P. W., White, F. J., 2001. Microchemical Methods for the Identification of Lichens. British Lichen Society, London." type="book" year="2001">Orange et al. (2001)</bibRefCitation>
|
||
. No spots were detected for conphysodalic acid and protocetraric acid because of their very low concentrations in the extract.
|
||
</paragraph>
|
||
<paragraph id="D578232DC910FFEF265EFB96FD058AFA" blockId="1.[831,1501,182,2015]" lastBlockId="2.[87,757,1374,2008]" lastPageId="2" lastPageNumber="118" pageId="1" pageNumber="117">
|
||
Hp4–hp8 compounds had UV absorption maxima in the range of
|
||
<quantity id="123F8EC8C910FFEC265DFB7AFC6C88E9" box="[861,990,1159,1178]" metricMagnitude="-7" metricUnit="m" metricValue="2.16" metricValueMax="2.2399999999999998" metricValueMin="2.08" pageId="1" pageNumber="117" unit="nm" value="216.0" valueMax="224.0" valueMin="208.0">208–224 nm</quantity>
|
||
,
|
||
<quantity id="123F8EC8C910FFEC26ECFB7BFBD988E9" box="[1004,1131,1158,1178]" metricMagnitude="-7" metricUnit="m" metricValue="2.6" metricValueMax="2.7" metricValueMin="2.5" pageId="1" pageNumber="117" unit="nm" value="260.0" valueMax="270.0" valueMin="250.0">250–270 nm</quantity>
|
||
and
|
||
<quantity id="123F8EC8C910FFEC21A7FB7AFA9788E9" box="[1191,1317,1159,1178]" metricMagnitude="-7" metricUnit="m" metricValue="3.165" metricValueMax="3.3299999999999996" metricValueMin="3.0" pageId="1" pageNumber="117" unit="nm" value="316.5" valueMax="333.0" valueMin="300.0">300–333 nm</quantity>
|
||
(
|
||
<tableCitation id="98451696C910FFEC2039FB7AFA3588E9" box="[1337,1415,1159,1178]" captionStart="Table 1" captionStartId="2.[87,131,728,742]" captionTargetPageId="2" captionText="Table 1 Chemical features of compounds isolated from H. physodes thalli. Retention times (R) from the UPLC analysis, UV absorption maxima (λ), molecular ion masses ([M—H] —), and t max relative retention factors (Rf) from the TLC analysis." httpUri="http://table.plazi.org/id/81B873A5C913FFEF2557FD25FE418F60" pageId="1" pageNumber="117" tableUuid="81B873A5C913FFEF2557FD25FE418F60">Table 1</tableCitation>
|
||
), which are typical for orcinol depsidones (
|
||
<bibRefCitation id="B1565EDCC910FFEC21A3FB5FFA7D88C6" author="Huneck, S. & Yoshimura, I." box="[1187,1487,1186,1205]" pageId="1" pageNumber="117" refId="ref8031" refString="Huneck, S., Yoshimura, I., 1996. Identification of Lichen Substances. Springer Verlag, Berlin." type="book" year="1996">Huneck and Yoshimura, 1996</bibRefCitation>
|
||
). The major compounds hp4 and hp7 that revealed the deprotonated molecules [M
|
||
<emphasis id="E7B3FF3FC910FFEC26C7FB27FC6A889E" box="[967,984,1242,1261]" italics="true" pageId="1" pageNumber="117">—</emphasis>
|
||
<collectionCode id="B3D6BBE8C910FFEC26D7FB26FC58889D" box="[983,1002,1243,1262]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="1" pageNumber="117" type="Herbarium">H</collectionCode>
|
||
]
|
||
<emphasis id="E7B3FF3FC910FFEC26F0FB2BFC4E8890" box="[1008,1020,1238,1251]" italics="true" pageId="1" pageNumber="117">
|
||
<superScript id="22B28E65C910FFEC26F0FB2BFC4E8890" attach="left" box="[1008,1020,1238,1251]" fontSize="5" pageId="1" pageNumber="117">—</superScript>
|
||
</emphasis>
|
||
at
|
||
<emphasis id="E7B3FF3FC910FFEC211BFB24FB9C889E" box="[1051,1070,1241,1261]" italics="true" pageId="1" pageNumber="117">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC910FFEC2135FB24FB8D889E" box="[1077,1087,1241,1261]" italics="true" pageId="1" pageNumber="117">z</emphasis>
|
||
485 and 469 (
|
||
<tableCitation id="98451696C910FFEC21D0FB27FAAB889E" box="[1232,1305,1242,1261]" captionStart="Table 1" captionStartId="2.[87,131,728,742]" captionTargetPageId="2" captionText="Table 1 Chemical features of compounds isolated from H. physodes thalli. Retention times (R) from the UPLC analysis, UV absorption maxima (λ), molecular ion masses ([M—H] —), and t max relative retention factors (Rf) from the TLC analysis." httpUri="http://table.plazi.org/id/81B873A5C913FFEF2557FD25FE418F60" pageId="1" pageNumber="117" tableUuid="81B873A5C913FFEF2557FD25FE418F60">Table 1</tableCitation>
|
||
) as well as similarities in the fragmentation pathways (
|
||
<figureCitation id="4DFC3FA8C910FFEC21B8FB0BFB5C897A" box="[1208,1262,1270,1289]" captionStart="Fig" captionStartId="4.[87,113,1280,1294]" captionTargetBox="[299,1255,184,1265]" captionTargetId="graphics-342@4.[678,870,706,839]" captionTargetPageId="4" captionText="Fig. 3. Proposed scheme of fragmentation pathways of compounds: hp4 – 3-hydroxyphysodic acid; hp5 – 4-O-methylphysodic acid; hp6 – 20-O-methylphysodic acid; hp7 – physodic acid; hp8 – OE-alectoronic acid." figureDoi="http://doi.org/10.5281/zenodo.10530148" httpUri="https://zenodo.org/record/10530148/files/figure.png" pageId="1" pageNumber="117">Fig. 3</figureCitation>
|
||
) were considered to be 3-hydroxyphysodic acid and physodic acid, respectively. Their fragmentation spectra revealed product ions corresponding to the loss of
|
||
<collectionCode id="B3D6BBE8C910FFEC2684FAB7FC26892E" box="[900,916,1354,1373]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="1" pageNumber="117" type="Herbarium">H</collectionCode>
|
||
<subScript id="49432168C910FFEC2694FAAEFC2F892C" attach="both" box="[916,925,1363,1375]" fontSize="5" pageId="1" pageNumber="117">2</subScript>
|
||
<collectionCode id="B3D6BBE8C910FFEC269DFAB7FC1F892E" box="[925,941,1354,1373]" country="Norway" lsid="urn:lsid:biocol.org:col:13093" name="Botanical Museum - University of Oslo" pageId="1" pageNumber="117" type="Herbarium">O</collectionCode>
|
||
or one or two
|
||
<collectionCode id="B3D6BBE8C910FFEC213FFAB7FBEE892E" box="[1087,1116,1354,1373]" country="France" lsid="urn:lsid:biocol.org:col:13662" name="Museum National d'Histoire Naturelle" pageId="1" pageNumber="117" type="Herbarium">CO</collectionCode>
|
||
<subScript id="49432168C910FFEC215CFAAEFBD7892C" attach="left" box="[1116,1125,1363,1375]" fontSize="5" pageId="1" pageNumber="117">2</subScript>
|
||
groups (
|
||
<figureCitation id="4DFC3FA8C910FFEC21BDFAB7FB41892E" box="[1213,1267,1354,1373]" captionStart="Fig" captionStartId="4.[87,113,1280,1294]" captionTargetBox="[299,1255,184,1265]" captionTargetId="graphics-342@4.[678,870,706,839]" captionTargetPageId="4" captionText="Fig. 3. Proposed scheme of fragmentation pathways of compounds: hp4 – 3-hydroxyphysodic acid; hp5 – 4-O-methylphysodic acid; hp6 – 20-O-methylphysodic acid; hp7 – physodic acid; hp8 – OE-alectoronic acid." figureDoi="http://doi.org/10.5281/zenodo.10530148" httpUri="https://zenodo.org/record/10530148/files/figure.png" pageId="1" pageNumber="117">Fig. 3</figureCitation>
|
||
). Additionally, the product ions at
|
||
<emphasis id="E7B3FF3FC910FFEC26BAFA98FC7F890A" box="[954,973,1381,1401]" italics="true" pageId="1" pageNumber="117">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC910FFEC26D4FA98FC6C890A" box="[980,990,1381,1401]" italics="true" pageId="1" pageNumber="117">z</emphasis>
|
||
423 (hp4) and 407 (hp7) corresponding to the loss of
|
||
<collectionCode id="B3D6BBE8C910FFEC265BFA7FFCD989E6" box="[859,875,1410,1429]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="1" pageNumber="117" type="Herbarium">H</collectionCode>
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||
<subScript id="49432168C910FFEC266BFA76FCC689E4" attach="both" box="[875,884,1419,1431]" fontSize="5" pageId="1" pageNumber="117">2</subScript>
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<collectionCode id="B3D6BBE8C910FFEC2675FA7FFC3789E6" box="[885,901,1410,1429]" country="Norway" lsid="urn:lsid:biocol.org:col:13093" name="Botanical Museum - University of Oslo" pageId="1" pageNumber="117" type="Herbarium">O</collectionCode>
|
||
molecule and successively one
|
||
<collectionCode id="B3D6BBE8C910FFEC21D2FA7FFB5D89E6" box="[1234,1263,1410,1429]" country="France" lsid="urn:lsid:biocol.org:col:13662" name="Museum National d'Histoire Naturelle" pageId="1" pageNumber="117" type="Herbarium">CO</collectionCode>
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<subScript id="49432168C910FFEC21EFFA76FB4A89E4" attach="left" box="[1263,1272,1419,1431]" fontSize="5" pageId="1" pageNumber="117">2</subScript>
|
||
group were detected. Furthermore, the fragments at
|
||
<emphasis id="E7B3FF3FC910FFEC217AFA61FB3F89C3" box="[1146,1165,1436,1456]" italics="true" pageId="1" pageNumber="117">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC910FFEC2195FA61FB2D89C3" box="[1173,1183,1436,1456]" italics="true" pageId="1" pageNumber="117">z</emphasis>
|
||
399 (hp4) and 383 (hp7) were formed by the loss of
|
||
<collectionCode id="B3D6BBE8C910FFEC2121FA44FB8C89BF" box="[1057,1086,1465,1484]" country="France" lsid="urn:lsid:biocol.org:col:13662" name="Museum National d'Histoire Naturelle" pageId="1" pageNumber="117" type="Herbarium">CO</collectionCode>
|
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<subScript id="49432168C910FFEC213EFA3EFBF589BC" attach="left" box="[1086,1095,1475,1487]" fontSize="5" pageId="1" pageNumber="117">2</subScript>
|
||
and (
|
||
<collectingCountry id="ADD063BDC910FFEC2182FA44FB1089BF" box="[1154,1186,1465,1484]" name="Switzerland" pageId="1" pageNumber="117">CH</collectingCountry>
|
||
<subScript id="49432168C910FFEC21A1FA3EFB1889BC" attach="left" box="[1185,1194,1475,1487]" fontSize="5" pageId="1" pageNumber="117">2</subScript>
|
||
–
|
||
<collectionCode id="B3D6BBE8C910FFEC21B7FA44FB6589BF" box="[1207,1239,1465,1484]" country="France" lsid="urn:lsid:biocol.org:col:13662" name="Museum National d'Histoire Naturelle" pageId="1" pageNumber="117" type="Herbarium">CO</collectionCode>
|
||
) groups. The authenticity of 3-hydroxyphysodic acid and physodic acid was confirmed by comparing the results of the TLC analysis (
|
||
<tableCitation id="98451696C910FFEC200CFA0CFAE88A77" box="[1292,1370,1521,1540]" captionStart="Table 1" captionStartId="2.[87,131,728,742]" captionTargetPageId="2" captionText="Table 1 Chemical features of compounds isolated from H. physodes thalli. Retention times (R) from the UPLC analysis, UV absorption maxima (λ), molecular ion masses ([M—H] —), and t max relative retention factors (Rf) from the TLC analysis." httpUri="http://table.plazi.org/id/81B873A5C913FFEF2557FD25FE418F60" pageId="1" pageNumber="117" tableUuid="81B873A5C913FFEF2557FD25FE418F60">Table 1</tableCitation>
|
||
) with those reported previously (
|
||
<bibRefCitation id="B1565EDCC910FFEC211BF9F0FB518A53" author="Orange, A. & James, P. W. & White, F. J." box="[1051,1251,1549,1569]" pageId="1" pageNumber="117" refId="ref8753" refString="Orange, A., James, P. W., White, F. J., 2001. Microchemical Methods for the Identification of Lichens. British Lichen Society, London." type="book" year="2001">Orange et al., 2001</bibRefCitation>
|
||
). The minor compound hp8 that displayed the deprotonated molecular ion [M
|
||
<emphasis id="E7B3FF3FC910FFEC2088F9D4FA2B8A4F" box="[1416,1433,1577,1596]" italics="true" pageId="1" pageNumber="117">—</emphasis>
|
||
<collectionCode id="B3D6BBE8C910FFEC2099F9D7FA198A4E" box="[1433,1451,1578,1597]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="1" pageNumber="117" type="Herbarium">H</collectionCode>
|
||
]
|
||
<emphasis id="E7B3FF3FC910FFEC20B1F9D9FA0F8A42" box="[1457,1469,1572,1585]" italics="true" pageId="1" pageNumber="117">
|
||
<superScript id="22B28E65C910FFEC20B1F9D9FA0F8A42" attach="left" box="[1457,1469,1572,1585]" fontSize="5" pageId="1" pageNumber="117">—</superScript>
|
||
</emphasis>
|
||
at
|
||
<emphasis id="E7B3FF3FC910FFEC263FF9B9FCE08A2B" box="[831,850,1604,1624]" italics="true" pageId="1" pageNumber="117">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC910FFEC2659F9B9FCD18A2B" box="[857,867,1604,1624]" italics="true" pageId="1" pageNumber="117">z</emphasis>
|
||
511 has been identified as
|
||
<emphasis id="E7B3FF3FC910FFEC2171F9BEFBCC8A2B" bold="true" box="[1137,1150,1603,1624]" italics="true" pageId="1" pageNumber="117">OE</emphasis>
|
||
-alectoronic acid. Its fragmentation pattern was partially consistent with the fragmentation route described above for 3-hydroxyphysodic acid and physodic acid (
|
||
<figureCitation id="4DFC3FA8C910FFEC2647F964FC358ADF" box="[839,903,1689,1708]" captionStart="Fig" captionStartId="4.[87,113,1280,1294]" captionTargetBox="[299,1255,184,1265]" captionTargetId="graphics-342@4.[678,870,706,839]" captionTargetPageId="4" captionText="Fig. 3. Proposed scheme of fragmentation pathways of compounds: hp4 – 3-hydroxyphysodic acid; hp5 – 4-O-methylphysodic acid; hp6 – 20-O-methylphysodic acid; hp7 – physodic acid; hp8 – OE-alectoronic acid." figureDoi="http://doi.org/10.5281/zenodo.10530148" httpUri="https://zenodo.org/record/10530148/files/figure.png" pageId="1" pageNumber="117">Fig. 3</figureCitation>
|
||
). The
|
||
<collectionCode id="B3D6BBE8C910FFEC26DAF964FC488ADF" box="[986,1018,1689,1708]" country="Italy" lsid="urn:lsid:biocol.org:col:14396" name="Herbarium Messanaensis, Università di Messina" pageId="1" pageNumber="117" type="Herbarium">MS</collectionCode>
|
||
/
|
||
<collectionCode id="B3D6BBE8C910FFEC2102F964FB908ADF" box="[1026,1058,1689,1708]" country="Italy" lsid="urn:lsid:biocol.org:col:14396" name="Herbarium Messanaensis, Università di Messina" pageId="1" pageNumber="117" type="Herbarium">MS</collectionCode>
|
||
spectrum of
|
||
<emphasis id="E7B3FF3FC910FFEC21C6F96AFB618ADF" bold="true" box="[1222,1235,1687,1708]" italics="true" pageId="1" pageNumber="117">OE</emphasis>
|
||
-alectoronic acid (Suppl.
|
||
<figureCitation id="4DFC3FA8C910FFEC263FF949FC208ABB" box="[831,914,1716,1736]" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="1" pageNumber="117">Fig. S1H</figureCitation>
|
||
) revealed product ions corresponding to the loss of
|
||
<collectionCode id="B3D6BBE8C910FFEC20B3F948FA718ABB" box="[1459,1475,1717,1736]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="1" pageNumber="117" type="Herbarium">H</collectionCode>
|
||
<subScript id="49432168C910FFEC20C3F943FA7E8AB9" attach="both" box="[1475,1484,1726,1738]" fontSize="5" pageId="1" pageNumber="117">2</subScript>
|
||
<collectionCode id="B3D6BBE8C910FFEC20CCF948FA6E8ABB" box="[1484,1500,1717,1736]" country="Norway" lsid="urn:lsid:biocol.org:col:13093" name="Botanical Museum - University of Oslo" pageId="1" pageNumber="117" type="Herbarium">O</collectionCode>
|
||
(at
|
||
<emphasis id="E7B3FF3FC910FFEC2662F932FCC78A90" box="[866,885,1743,1763]" italics="true" pageId="1" pageNumber="117">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC910FFEC267CF932FC348A90" box="[892,902,1743,1763]" italics="true" pageId="1" pageNumber="117">z</emphasis>
|
||
493) or a
|
||
<collectionCode id="B3D6BBE8C910FFEC26F2F92CFBBD8A97" box="[1010,1039,1745,1764]" country="France" lsid="urn:lsid:biocol.org:col:13662" name="Museum National d'Histoire Naturelle" pageId="1" pageNumber="117" type="Herbarium">CO</collectionCode>
|
||
<subScript id="49432168C910FFEC210FF924FBAA8A96" attach="left" box="[1039,1048,1753,1765]" fontSize="5" pageId="1" pageNumber="117">2</subScript>
|
||
group (at
|
||
<emphasis id="E7B3FF3FC910FFEC2185F932FB2A8A90" box="[1157,1176,1743,1763]" italics="true" pageId="1" pageNumber="117">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC910FFEC21A0F932FB188A90" box="[1184,1194,1743,1763]" italics="true" pageId="1" pageNumber="117">z</emphasis>
|
||
467). Moreover, the daughter ions at
|
||
<emphasis id="E7B3FF3FC910FFEC2687F916FC288A8C" box="[903,922,1771,1791]" italics="true" pageId="1" pageNumber="117">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC910FFEC26A2F916FC1E8A8C" box="[930,940,1771,1791]" italics="true" pageId="1" pageNumber="117">z</emphasis>
|
||
449 and 423 resulted from the loss of a
|
||
<collectionCode id="B3D6BBE8C910FFEC203FF911FAEE8A8C" box="[1343,1372,1772,1791]" country="France" lsid="urn:lsid:biocol.org:col:13662" name="Museum National d'Histoire Naturelle" pageId="1" pageNumber="117" type="Herbarium">CO</collectionCode>
|
||
<subScript id="49432168C910FFEC205CF908FAD78B72" attach="left" box="[1372,1381,1781,1793]" fontSize="5" pageId="1" pageNumber="117">2</subScript>
|
||
group from the above-mentioned product ions. In addition, trace quantities were detected of the other two compounds hp5 and hp6, which did not
|
||
<taxonomicName id="12C758AEC910FFEC2694F8BDFBAB8B20" box="[916,1049,1856,1875]" form="distinct" pageId="1" pageNumber="117" rank="form">form distinct</taxonomicName>
|
||
peaks on the
|
||
<collectionCode id="B3D6BBE8C910FFEC21B2F8BDFB548B20" box="[1202,1254,1856,1875]" pageId="1" pageNumber="117">UPLC</collectionCode>
|
||
chromatogram (
|
||
<figureCitation id="4DFC3FA8C910FFEC2096F8BDFA7D8B20" box="[1430,1487,1856,1875]" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="1" pageNumber="117">Fig. 1</figureCitation>
|
||
). Based on the conformity of their UV absorption maxima (
|
||
<tableCitation id="98451696C910FFEC208AF8A1FA668B1C" box="[1418,1492,1884,1903]" captionStart="Table 1" captionStartId="2.[87,131,728,742]" captionTargetPageId="2" captionText="Table 1 Chemical features of compounds isolated from H. physodes thalli. Retention times (R) from the UPLC analysis, UV absorption maxima (λ), molecular ion masses ([M—H] —), and t max relative retention factors (Rf) from the TLC analysis." httpUri="http://table.plazi.org/id/81B873A5C913FFEF2557FD25FE418F60" pageId="1" pageNumber="117" tableUuid="81B873A5C913FFEF2557FD25FE418F60">Table 1</tableCitation>
|
||
) with literature (
|
||
<bibRefCitation id="B1565EDCC910FFEC26E4F885FAA18BF8" author="Huneck, S. & Yoshimura, I." box="[996,1299,1912,1931]" pageId="1" pageNumber="117" refId="ref8031" refString="Huneck, S., Yoshimura, I., 1996. Identification of Lichen Substances. Springer Verlag, Berlin." type="book" year="1996">Huneck and Yoshimura, 1996</bibRefCitation>
|
||
) and similarities of the mass spectra (Suppl.
|
||
<figureCitation id="4DFC3FA8C910FFEC2140F869FB158BD4" box="[1088,1191,1940,1959]" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="1" pageNumber="117">Fig. S1E–F</figureCitation>
|
||
), they were identified as 4-
|
||
<emphasis id="E7B3FF3FC910FFEC20C5F86EFA668BD4" box="[1477,1492,1939,1959]" italics="true" pageId="1" pageNumber="117">
|
||
<collectionCode id="B3D6BBE8C910FFEC20C5F86EFA668BD4" box="[1477,1492,1939,1959]" country="Norway" lsid="urn:lsid:biocol.org:col:13093" name="Botanical Museum - University of Oslo" pageId="1" pageNumber="117" type="Herbarium">O</collectionCode>
|
||
</emphasis>
|
||
- methylphysodic acid and 2
|
||
<emphasis id="E7B3FF3FC910FFEC2155F850FBC08BB0" box="[1109,1138,1965,1987]" italics="true" pageId="1" pageNumber="117">
|
||
<superScript id="22B28E65C910FFEC2155F850FBEB8BCA" attach="none" box="[1109,1113,1965,1977]" fontSize="5" pageId="1" pageNumber="117">0</superScript>
|
||
-
|
||
<collectionCode id="B3D6BBE8C910FFEC2163F852FBC08BB0" box="[1123,1138,1967,1987]" country="Norway" lsid="urn:lsid:biocol.org:col:13093" name="Botanical Museum - University of Oslo" pageId="1" pageNumber="117" type="Herbarium">O</collectionCode>
|
||
</emphasis>
|
||
-methylphysodic acid, respectively; all of which belong to the orcinol depsidones. They were recognised by their characteristic daughter ions derived from the typical depsidone A-ring fragmentation (
|
||
<bibRefCitation id="B1565EDCC913FFEF24B2FA87FDAA89FE" author="Elix, J. A." box="[434,536,1402,1421]" pageId="2" pageNumber="118" pagination="849 - 858" refId="ref7572" refString="Elix, J. A., 1975. 2 0 - O - methylphysodic acid and hydroxyphysodic acid: two new depsidones from the lichen Hypogymnia billardieri. Aust. J. Chem. 28, 849 - 858." type="journal article" year="1975">Elix, 1975</bibRefCitation>
|
||
). In the negative ion mass spectrum of 4-
|
||
<emphasis id="E7B3FF3FC913FFEF243BFA68FEF889DA" box="[315,330,1429,1449]" italics="true" pageId="2" pageNumber="118">
|
||
<collectionCode id="B3D6BBE8C913FFEF243BFA68FEF889DA" box="[315,330,1429,1449]" country="Norway" lsid="urn:lsid:biocol.org:col:13093" name="Botanical Museum - University of Oslo" pageId="2" pageNumber="118" type="Herbarium">O</collectionCode>
|
||
</emphasis>
|
||
-methylphysodic acid, the daughter ion was observed at
|
||
<emphasis id="E7B3FF3FC913FFEF2403FA4CFEA489B6" box="[259,278,1457,1477]" italics="true" pageId="2" pageNumber="118">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC913FFEF241EFA4CFE9A89B6" box="[286,296,1457,1477]" italics="true" pageId="2" pageNumber="118">z</emphasis>
|
||
261 (Suppl.
|
||
<figureCitation id="4DFC3FA8C913FFEF24AAFA4FFE4A89B6" box="[426,504,1458,1477]" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="2" pageNumber="118">Fig. S1E</figureCitation>
|
||
), in contrast to the fragmentation spectrum of 2
|
||
<emphasis id="E7B3FF3FC913FFEF244FFA36FEDE8992" box="[335,364,1483,1505]" italics="true" pageId="2" pageNumber="118">
|
||
<superScript id="22B28E65C913FFEF244FFA36FEE189A4" attach="none" box="[335,339,1483,1495]" fontSize="5" pageId="2" pageNumber="118">0</superScript>
|
||
-
|
||
<collectionCode id="B3D6BBE8C913FFEF245DFA30FEDE8992" box="[349,364,1485,1505]" country="Norway" lsid="urn:lsid:biocol.org:col:13093" name="Botanical Museum - University of Oslo" pageId="2" pageNumber="118" type="Herbarium">O</collectionCode>
|
||
</emphasis>
|
||
-methylphysodic acid in which the corresponding product ion was detected at
|
||
<emphasis id="E7B3FF3FC913FFEF24F4FA14FDB5898E" box="[500,519,1513,1533]" italics="true" pageId="2" pageNumber="118">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC913FFEF270FFA14FDAB898E" box="[527,537,1513,1533]" italics="true" pageId="2" pageNumber="118">z</emphasis>
|
||
247 (Suppl.
|
||
<figureCitation id="4DFC3FA8C913FFEF279AFA17FD5A898E" box="[666,744,1514,1533]" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="2" pageNumber="118">Fig. S1F</figureCitation>
|
||
). The ion at
|
||
<emphasis id="E7B3FF3FC913FFEF25BFF9F8FF608A6A" box="[191,210,1541,1561]" italics="true" pageId="2" pageNumber="118">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC913FFEF25D9F9F8FF518A6A" box="[217,227,1541,1561]" italics="true" pageId="2" pageNumber="118">z</emphasis>
|
||
247 was also present in the mass spectra of physodic acid and the related depsidone
|
||
<emphasis id="E7B3FF3FC913FFEF2492F9DDFE2D8A46" bold="true" box="[402,415,1568,1589]" italics="true" pageId="2" pageNumber="118">OE</emphasis>
|
||
-alectoronic acid (Suppl.
|
||
<figureCitation id="4DFC3FA8C913FFEF2798F9DFFFD58A22" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="2" pageNumber="118">Fig. S1G– H</figureCitation>
|
||
). The presence of this product ion resulted from the structural similarities of these molecules; they all have the same aromatic ring structure on the left-hand side of the molecule (
|
||
<figureCitation id="4DFC3FA8C913FFEF2773F988FD188AFA" box="[627,682,1653,1673]" captionStart="Fig" captionStartId="4.[87,113,1280,1294]" captionTargetBox="[299,1255,184,1265]" captionTargetId="graphics-342@4.[678,870,706,839]" captionTargetPageId="4" captionText="Fig. 3. Proposed scheme of fragmentation pathways of compounds: hp4 – 3-hydroxyphysodic acid; hp5 – 4-O-methylphysodic acid; hp6 – 20-O-methylphysodic acid; hp7 – physodic acid; hp8 – OE-alectoronic acid." figureDoi="http://doi.org/10.5281/zenodo.10530148" httpUri="https://zenodo.org/record/10530148/files/figure.png" pageId="2" pageNumber="118">Fig. 3</figureCitation>
|
||
).
|
||
</paragraph>
|
||
<caption id="81B873A5C913FFEF25D4FD71FAF58EE9" ID-DOI="http://doi.org/10.5281/zenodo.10488551" ID-Zenodo-Dep="10488551" box="[212,1351,652,667]" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="2" pageNumber="118" startId="2.[212,238,652,666]" targetBox="[171,1380,184,623]" targetPageId="2" targetType="figure">
|
||
<paragraph id="D578232DC913FFEF25D4FD71FAF58EE9" blockId="2.[212,1351,652,667]" box="[212,1351,652,667]" pageId="2" pageNumber="118">
|
||
<emphasis id="E7B3FF3FC913FFEF25D4FD71FEB48EE9" bold="true" box="[212,262,652,666]" pageId="2" pageNumber="118">Fig. 1.</emphasis>
|
||
Chromatogram of extracts from
|
||
<taxonomicName id="12C758AEC913FFEF2715FD71FDC38EE8" box="[533,625,652,667]" class="Lecanoromycetes" family="Parmeliaceae" genus="Hypogymnia" kingdom="Fungi" order="Lecanorales" pageId="2" pageNumber="118" phylum="Ascomycota" rank="species" species="physodes">
|
||
<emphasis id="E7B3FF3FC913FFEF2715FD71FDC38EE8" box="[533,625,652,667]" italics="true" pageId="2" pageNumber="118">H. physodes</emphasis>
|
||
</taxonomicName>
|
||
thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites.
|
||
</paragraph>
|
||
</caption>
|
||
<caption id="81B873A5C913FFEF2557FD25FE418F60" ID-Table-UUID="81B873A5C913FFEF2557FD25FE418F60" httpUri="http://table.plazi.org/id/81B873A5C913FFEF2557FD25FE418F60" pageId="2" pageNumber="118" startId="2.[87,131,728,742]" targetBox="[110,1451,807,1296]" targetIsTable="true" targetPageId="2" targetType="table">
|
||
<paragraph id="D578232DC913FFEF2557FD25FE418F60" blockId="2.[87,1474,727,790]" pageId="2" pageNumber="118">
|
||
<emphasis id="E7B3FF3FC913FFEF2557FD25FF218E96" bold="true" box="[87,147,727,742]" pageId="2" pageNumber="118">Table 1</emphasis>
|
||
Chemical features of compounds isolated from
|
||
<taxonomicName id="12C758AEC913FFEF24C8FD13FD928E8E" box="[456,544,750,765]" class="Lecanoromycetes" family="Parmeliaceae" genus="Hypogymnia" kingdom="Fungi" order="Lecanorales" pageId="2" pageNumber="118" phylum="Ascomycota" rank="species" species="physodes">
|
||
<emphasis id="E7B3FF3FC913FFEF24C8FD13FD928E8E" box="[456,544,750,765]" italics="true" pageId="2" pageNumber="118">H. physodes</emphasis>
|
||
</taxonomicName>
|
||
thalli. Retention times (
|
||
<emphasis id="E7B3FF3FC913FFEF27DDFD13FD408E8F" box="[733,754,750,765]" italics="true" pageId="2" pageNumber="118">R)</emphasis>
|
||
from the UPLC analysis, UV absorption maxima (
|
||
<emphasis id="E7B3FF3FC913FFEF2172FD13FBC98E8E" bold="true" box="[1138,1147,750,765]" italics="true" pageId="2" pageNumber="118">λ</emphasis>
|
||
), molecular ion masses ([M
|
||
<emphasis id="E7B3FF3FC913FFEF206CFD13FACB8E8E" box="[1388,1401,750,765]" italics="true" pageId="2" pageNumber="118">—</emphasis>
|
||
H]
|
||
<emphasis id="E7B3FF3FC913FFEF208CFD17FA248E87" box="[1420,1430,746,756]" italics="true" pageId="2" pageNumber="118">
|
||
<superScript id="22B28E65C913FFEF208CFD17FA248E87" attach="none" box="[1420,1430,746,756]" fontSize="4" pageId="2" pageNumber="118">—</superScript>
|
||
</emphasis>
|
||
), and
|
||
<subScript id="49432168C913FFEF27E7FD09FB268E8D" attach="left" box="[743,1172,756,767]" fontSize="4" pageId="2" pageNumber="118">
|
||
<emphasis id="E7B3FF3FC913FFEF27E7FD09FD5E8E8C" box="[743,748,756,767]" italics="true" pageId="2" pageNumber="118">t</emphasis>
|
||
max
|
||
</subScript>
|
||
relative retention factors (
|
||
<emphasis id="E7B3FF3FC913FFEF2428FCF9FE848F65" box="[296,310,772,790]" italics="true" pageId="2" pageNumber="118">
|
||
<subScript id="49432168C913FFEF2428FCF9FE848F65" attach="left" box="[296,310,772,790]" fontSize="4" pageId="2" pageNumber="118">Rf</subScript>
|
||
</emphasis>
|
||
) from the TLC analysis.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="D578232DC913FFEF256EFCD6FA37897E" pageId="2" pageNumber="118">
|
||
<table id="A7C7D18DC9130012256EFCDAFA198963" box="[110,1451,807,1296]" gridcols="6" gridrows="11" pageId="2" pageNumber="118">
|
||
<tr id="6BF7216FC9130012256EFCDAFA198F4F" box="[110,1451,807,828]" gridrow="0" pageId="2" pageNumber="118">
|
||
<th id="28264813C9130012256EFCDAFF748F4F" box="[110,198,807,828]" gridcol="0" gridrow="0" pageId="2" pageNumber="118">Compound</th>
|
||
<th id="28264813C91300122445FCDAFE348F4F" box="[325,390,807,828]" gridcol="1" gridrow="0" pageId="2" pageNumber="118">
|
||
<emphasis id="E7B3FF3FC913FFEF2445FCD6FEE68F4F" box="[325,340,811,828]" italics="true" pageId="2" pageNumber="118">Rt</emphasis>
|
||
(min)
|
||
</th>
|
||
<th id="28264813C91300122704FCDAFD138F4F" box="[516,673,807,828]" gridcol="2" gridrow="0" pageId="2" pageNumber="118">
|
||
UV
|
||
<emphasis id="E7B3FF3FC913FFEF2722FCD6FD998F49" bold="true" box="[546,555,811,826]" italics="true" pageId="2" pageNumber="118">λ</emphasis>
|
||
max (nm)
|
||
</th>
|
||
<th id="28264813C91300122620FCDAFC238F4F" box="[800,913,807,828]" gridcol="3" gridrow="0" pageId="2" pageNumber="118">
|
||
[M
|
||
<emphasis id="E7B3FF3FC913FFEF2637FCD6FCF68F49" box="[823,836,811,826]" italics="true" pageId="2" pageNumber="118">—</emphasis>
|
||
H]
|
||
<emphasis id="E7B3FF3FC913FFEF2658FCDAFCD08F42" box="[856,866,807,817]" italics="true" pageId="2" pageNumber="118">—</emphasis>
|
||
(
|
||
<emphasis id="E7B3FF3FC913FFEF266EFCD6FCCF8F49" box="[878,893,811,826]" italics="true" pageId="2" pageNumber="118">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC913FFEF2683FCD6FC398F49" box="[899,907,811,826]" italics="true" pageId="2" pageNumber="118">z</emphasis>
|
||
)
|
||
</th>
|
||
<th id="28264813C91300122110FCDAFBEE8F4F" box="[1040,1116,807,828]" gridcol="4" gridrow="0" pageId="2" pageNumber="118">
|
||
<emphasis id="E7B3FF3FC913FFEF2110FCD6FBAC8F4F" box="[1040,1054,811,828]" italics="true" pageId="2" pageNumber="118">Rf</emphasis>
|
||
(
|
||
<emphasis id="E7B3FF3FC913FFEF212AFCD6FB858F49" box="[1066,1079,811,826]" italics="true" pageId="2" pageNumber="118">×</emphasis>
|
||
100)
|
||
</th>
|
||
<th id="28264813C913001221DAFCDAFA198F4F" box="[1242,1451,807,828]" gridcol="5" gridrow="0" pageId="2" pageNumber="118">Identification</th>
|
||
</tr>
|
||
<tr id="6BF7216FC9130012256EFCB0FA198F07" box="[110,1451,845,884]" gridrow="1" pageId="2" pageNumber="118">
|
||
<th id="28264813C9130012256EFCB0FF748F07" box="[110,198,845,884]" gridcol="0" gridrow="1" pageId="2" pageNumber="118">hp1</th>
|
||
<td id="28264813C91300122445FCB0FE348F07" box="[325,390,845,884]" gridcol="1" gridrow="1" pageId="2" pageNumber="118">4.5</td>
|
||
<td id="28264813C91300122704FCB0FD138F07" box="[516,673,845,884]" gridcol="2" gridrow="1" pageId="2" pageNumber="118">212; 266; 312</td>
|
||
<td id="28264813C91300122620FCB0FC238F07" box="[800,913,845,884]" gridcol="3" gridrow="1" pageId="2" pageNumber="118">417</td>
|
||
<td id="28264813C91300122110FCB0FBEE8F07" box="[1040,1116,845,884]" gridcol="4" gridrow="1" pageId="2" pageNumber="118">n.d.</td>
|
||
<td id="28264813C913001221DAFCB0FA198F07" box="[1242,1451,845,884]" gridcol="5" gridrow="1" pageId="2" pageNumber="118">Conphysodalic acid C20H18O10, Mr 418.3</td>
|
||
</tr>
|
||
<tr id="6BF7216FC9130012256EFC86FA198FD1" box="[110,1451,891,930]" gridrow="2" pageId="2" pageNumber="118">
|
||
<th id="28264813C9130012256EFC86FF748FD1" box="[110,198,891,930]" gridcol="0" gridrow="2" pageId="2" pageNumber="118">hp2</th>
|
||
<td id="28264813C91300122445FC86FE348FD1" box="[325,390,891,930]" gridcol="1" gridrow="2" pageId="2" pageNumber="118">5.0</td>
|
||
<td id="28264813C91300122704FC86FD138FD1" box="[516,673,891,930]" gridcol="2" gridrow="2" pageId="2" pageNumber="118">211; 243; 314</td>
|
||
<td id="28264813C91300122620FC86FC238FD1" box="[800,913,891,930]" gridcol="3" gridrow="2" pageId="2" pageNumber="118">373</td>
|
||
<td id="28264813C91300122110FC86FBEE8FD1" box="[1040,1116,891,930]" gridcol="4" gridrow="2" pageId="2" pageNumber="118">n.d.</td>
|
||
<td id="28264813C913001221DAFC86FA198FD1" box="[1242,1451,891,930]" gridcol="5" gridrow="2" pageId="2" pageNumber="118">Protocetraric acid C18H14O9, Mr 374.3</td>
|
||
</tr>
|
||
<tr id="6BF7216FC9130012256EFC55FA198FA3" box="[110,1451,936,976]" gridrow="3" pageId="2" pageNumber="118">
|
||
<th id="28264813C9130012256EFC55FF748FA3" box="[110,198,936,976]" gridcol="0" gridrow="3" pageId="2" pageNumber="118">hp3</th>
|
||
<td id="28264813C91300122445FC55FE348FA3" box="[325,390,936,976]" gridcol="1" gridrow="3" pageId="2" pageNumber="118">6.1</td>
|
||
<td id="28264813C91300122704FC55FD138FA3" box="[516,673,936,976]" gridcol="2" gridrow="3" pageId="2" pageNumber="118">211; 242; 315</td>
|
||
<td id="28264813C91300122620FC55FC238FA3" box="[800,913,936,976]" gridcol="3" gridrow="3" pageId="2" pageNumber="118">415</td>
|
||
<td id="28264813C91300122110FC55FBEE8FA3" box="[1040,1116,936,976]" gridcol="4" gridrow="3" pageId="2" pageNumber="118">19</td>
|
||
<td id="28264813C913001221DAFC55FA198FA3" box="[1242,1451,936,976]" gridcol="5" gridrow="3" pageId="2" pageNumber="118">Physodalic acid C20H16O10, Mr 416.3</td>
|
||
</tr>
|
||
<tr id="6BF7216FC9130012256EFC2BFA198F8E" box="[110,1451,982,1021]" gridrow="4" pageId="2" pageNumber="118">
|
||
<th id="28264813C9130012256EFC2BFF748F8E" box="[110,198,982,1021]" gridcol="0" gridrow="4" pageId="2" pageNumber="118">hp4</th>
|
||
<td id="28264813C91300122445FC2BFE348F8E" box="[325,390,982,1021]" gridcol="1" gridrow="4" pageId="2" pageNumber="118">6.9</td>
|
||
<td id="28264813C91300122704FC2BFD138F8E" box="[516,673,982,1021]" gridcol="2" gridrow="4" pageId="2" pageNumber="118">218; 278; 308</td>
|
||
<td id="28264813C91300122620FC2BFC238F8E" box="[800,913,982,1021]" gridcol="3" gridrow="4" pageId="2" pageNumber="118">485</td>
|
||
<td id="28264813C91300122110FC2BFBEE8F8E" box="[1040,1116,982,1021]" gridcol="4" gridrow="4" pageId="2" pageNumber="118">13</td>
|
||
<td id="28264813C913001221DAFC2BFA198F8E" box="[1242,1451,982,1021]" gridcol="5" gridrow="4" pageId="2" pageNumber="118">3-Hydroxyphysodic acid C26H30O9, Mr 486.5</td>
|
||
</tr>
|
||
<tr id="6BF7216FC9130012256EFC02FA198858" box="[110,1451,1023,1067]" gridrow="5" pageId="2" pageNumber="118">
|
||
<th id="28264813C9130012256EFC02FF748858" box="[110,198,1023,1067]" gridcol="0" gridrow="5" pageId="2" pageNumber="118">hp5</th>
|
||
<td id="28264813C91300122445FC02FE348858" box="[325,390,1023,1067]" gridcol="1" gridrow="5" pageId="2" pageNumber="118">7.0 *</td>
|
||
<td id="28264813C91300122704FC02FD138858" box="[516,673,1023,1067]" gridcol="2" gridrow="5" pageId="2" pageNumber="118">204; 215; 269</td>
|
||
<td id="28264813C91300122620FC02FC238858" box="[800,913,1023,1067]" gridcol="3" gridrow="5" pageId="2" pageNumber="118">483</td>
|
||
<td id="28264813C91300122110FC02FBEE8858" box="[1040,1116,1023,1067]" gridcol="4" gridrow="5" pageId="2" pageNumber="118">n.d.</td>
|
||
<td id="28264813C913001221DAFC02FA198858" box="[1242,1451,1023,1067]" gridcol="5" gridrow="5" pageId="2" pageNumber="118">
|
||
4-
|
||
<emphasis id="E7B3FF3FC913FFEF21ECFBFFFB4A8861" box="[1260,1272,1026,1042]" italics="true" pageId="2" pageNumber="118">O</emphasis>
|
||
-methylphysodic acid C27H32O8, Mr484.5
|
||
</td>
|
||
</tr>
|
||
<tr id="6BF7216FC9130012256EFBD0FA19882A" box="[110,1451,1069,1113]" gridrow="6" pageId="2" pageNumber="118">
|
||
<th id="28264813C9130012256EFBD0FF74882A" box="[110,198,1069,1113]" gridcol="0" gridrow="6" pageId="2" pageNumber="118">hp6</th>
|
||
<td id="28264813C91300122445FBD0FE34882A" box="[325,390,1069,1113]" gridcol="1" gridrow="6" pageId="2" pageNumber="118">7.2 *</td>
|
||
<td id="28264813C91300122704FBD0FD13882A" box="[516,673,1069,1113]" gridcol="2" gridrow="6" pageId="2" pageNumber="118">216; 245; 319</td>
|
||
<td id="28264813C91300122620FBD0FC23882A" box="[800,913,1069,1113]" gridcol="3" gridrow="6" pageId="2" pageNumber="118">483</td>
|
||
<td id="28264813C91300122110FBD0FBEE882A" box="[1040,1116,1069,1113]" gridcol="4" gridrow="6" pageId="2" pageNumber="118">n.d.</td>
|
||
<td id="28264813C913001221DAFBD0FA19882A" box="[1242,1451,1069,1113]" gridcol="5" gridrow="6" pageId="2" pageNumber="118">
|
||
2
|
||
<emphasis id="E7B3FF3FC913FFEF21E5FBD3FB5B884A" box="[1253,1257,1070,1081]" italics="true" pageId="2" pageNumber="118">0</emphasis>
|
||
<emphasis id="E7B3FF3FC913FFEF21E9FBCFFB4E8833" box="[1257,1276,1072,1088]" italics="true" pageId="2" pageNumber="118">-O</emphasis>
|
||
-methylphysodic acid C27H32O8, Mr484.5
|
||
</td>
|
||
</tr>
|
||
<tr id="6BF7216FC9130012256EFBA2FA1988F4" box="[110,1451,1119,1159]" gridrow="7" pageId="2" pageNumber="118">
|
||
<th id="28264813C9130012256EFBA2FF7488F4" box="[110,198,1119,1159]" gridcol="0" gridrow="7" pageId="2" pageNumber="118">hp7</th>
|
||
<td id="28264813C91300122445FBA2FE3488F4" box="[325,390,1119,1159]" gridcol="1" gridrow="7" pageId="2" pageNumber="118">7.6</td>
|
||
<td id="28264813C91300122704FBA2FD1388F4" box="[516,673,1119,1159]" gridcol="2" gridrow="7" pageId="2" pageNumber="118">209; 259; 318</td>
|
||
<td id="28264813C91300122620FBA2FC2388F4" box="[800,913,1119,1159]" gridcol="3" gridrow="7" pageId="2" pageNumber="118">469</td>
|
||
<td id="28264813C91300122110FBA2FBEE88F4" box="[1040,1116,1119,1159]" gridcol="4" gridrow="7" pageId="2" pageNumber="118">18</td>
|
||
<td id="28264813C913001221DAFBA2FA1988F4" box="[1242,1451,1119,1159]" gridcol="5" gridrow="7" pageId="2" pageNumber="118">Physodic acid C26H30O8, Mr470.5</td>
|
||
</tr>
|
||
<tr id="6BF7216FC9130012256EFB77FA1988C7" box="[110,1451,1162,1204]" gridrow="8" pageId="2" pageNumber="118">
|
||
<th id="28264813C9130012256EFB77FF7488C7" box="[110,198,1162,1204]" gridcol="0" gridrow="8" pageId="2" pageNumber="118">hp8</th>
|
||
<td id="28264813C91300122445FB77FE3488C7" box="[325,390,1162,1204]" gridcol="1" gridrow="8" pageId="2" pageNumber="118">7.9</td>
|
||
<td id="28264813C91300122704FB77FD1388C7" box="[516,673,1162,1204]" gridcol="2" gridrow="8" pageId="2" pageNumber="118">214; 255; 318</td>
|
||
<td id="28264813C91300122620FB77FC2388C7" box="[800,913,1162,1204]" gridcol="3" gridrow="8" pageId="2" pageNumber="118">511</td>
|
||
<td id="28264813C91300122110FB77FBEE88C7" box="[1040,1116,1162,1204]" gridcol="4" gridrow="8" pageId="2" pageNumber="118">n.d.</td>
|
||
<td id="28264813C913001221DAFB77FA1988C7" box="[1242,1451,1162,1204]" gridcol="5" gridrow="8" pageId="2" pageNumber="118">
|
||
<emphasis id="E7B3FF3FC913FFEF21DAFB77FB5688EF" bold="true" box="[1242,1252,1162,1180]" italics="true" pageId="2" pageNumber="118">OE</emphasis>
|
||
-Alectoronic acid C28H32O9, Mr 512.5
|
||
</td>
|
||
</tr>
|
||
<tr id="6BF7216FC9130012256EFB46FA198891" box="[110,1451,1211,1250]" gridrow="9" pageId="2" pageNumber="118">
|
||
<th id="28264813C9130012256EFB46FF748891" box="[110,198,1211,1250]" gridcol="0" gridrow="9" pageId="2" pageNumber="118">hp9</th>
|
||
<td id="28264813C91300122445FB46FE348891" box="[325,390,1211,1250]" gridcol="1" gridrow="9" pageId="2" pageNumber="118">8.8</td>
|
||
<td id="28264813C91300122704FB46FD138891" box="[516,673,1211,1250]" gridcol="2" gridrow="9" pageId="2" pageNumber="118">211; 252; 321</td>
|
||
<td id="28264813C91300122620FB46FC238891" box="[800,913,1211,1250]" gridcol="3" gridrow="9" pageId="2" pageNumber="118">373</td>
|
||
<td id="28264813C91300122110FB46FBEE8891" box="[1040,1116,1211,1250]" gridcol="4" gridrow="9" pageId="2" pageNumber="118">79</td>
|
||
<td id="28264813C913001221DAFB46FA198891" box="[1242,1451,1211,1250]" gridcol="5" gridrow="9" pageId="2" pageNumber="118">Atranorin C19H18O8, Mr 374.3</td>
|
||
</tr>
|
||
<tr id="6BF7216FC9130012256EFB15FA198963" box="[110,1451,1256,1296]" gridrow="10" pageId="2" pageNumber="118">
|
||
<th id="28264813C9130012256EFB15FF748963" box="[110,198,1256,1296]" gridcol="0" gridrow="10" pageId="2" pageNumber="118">hp10</th>
|
||
<td id="28264813C91300122445FB15FE348963" box="[325,390,1256,1296]" gridcol="1" gridrow="10" pageId="2" pageNumber="118">9.1</td>
|
||
<td id="28264813C91300122704FB15FD138963" box="[516,673,1256,1296]" gridcol="2" gridrow="10" pageId="2" pageNumber="118">211; 250; 315; 350</td>
|
||
<td id="28264813C91300122620FB15FC238963" box="[800,913,1256,1296]" gridcol="3" gridrow="10" pageId="2" pageNumber="118">407</td>
|
||
<td id="28264813C91300122110FB15FBEE8963" box="[1040,1116,1256,1296]" gridcol="4" gridrow="10" pageId="2" pageNumber="118">n.d.</td>
|
||
<td id="28264813C913001221DAFB15FA198963" box="[1242,1451,1256,1296]" gridcol="5" gridrow="10" pageId="2" pageNumber="118">Chloroatranorin C19H17ClO8, Mr 408.8</td>
|
||
</tr>
|
||
</table>
|
||
</paragraph>
|
||
<tableNote id="282122A3C913FFEF2567FADCFF5F8947" box="[103,237,1313,1332]" pageId="2" pageNumber="118" targetBox="[110,1451,807,1296]" targetPageId="2">
|
||
<paragraph id="D578232DC913FFEF2567FADCFFDC8958" blockId="2.[103,237,1313,1332]" box="[103,110,1313,1323]" pageId="2" pageNumber="118">*</paragraph>
|
||
<paragraph id="D578232DC913FFEF2577FADBFF5F8947" blockId="2.[103,237,1313,1332]" box="[119,237,1318,1332]" pageId="2" pageNumber="118">Trace amount.</paragraph>
|
||
</tableNote>
|
||
<paragraph id="D578232DC913FFEF2576F96CFAC589B6" blockId="2.[87,757,1374,2008]" lastBlockId="2.[805,1475,1374,2008]" pageId="2" pageNumber="118">
|
||
The UV spectra of compounds hp9 and hp10 displayed a high similarity (
|
||
<tableCitation id="98451696C913FFEF25C9F950FEA78AB2" box="[201,277,1709,1729]" captionStart="Table 1" captionStartId="2.[87,131,728,742]" captionTargetPageId="2" captionText="Table 1 Chemical features of compounds isolated from H. physodes thalli. Retention times (R) from the UPLC analysis, UV absorption maxima (λ), molecular ion masses ([M—H] —), and t max relative retention factors (Rf) from the TLC analysis." httpUri="http://table.plazi.org/id/81B873A5C913FFEF2557FD25FE418F60" pageId="2" pageNumber="118" tableUuid="81B873A5C913FFEF2557FD25FE418F60">Table 1</tableCitation>
|
||
) and corresponded to the
|
||
<emphasis id="E7B3FF3FC913FFEF272EF950FD888AB3" bold="true" box="[558,570,1709,1728]" italics="true" pageId="2" pageNumber="118">β</emphasis>
|
||
-orcinol
|
||
<emphasis id="E7B3FF3FC913FFEF2792F951FD0C8AB3" box="[658,702,1708,1728]" italics="true" pageId="2" pageNumber="118">para</emphasis>
|
||
-depsides atranorin and chloroatranorin, respectively (
|
||
<bibRefCitation id="B1565EDCC913FFEF2775F934FEB68A8B" author="Huneck, S. & Yoshimura, I." pageId="2" pageNumber="118" refId="ref8031" refString="Huneck, S., Yoshimura, I., 1996. Identification of Lichen Substances. Springer Verlag, Berlin." type="book" year="1996">Huneck and Yoshimura, 1996</bibRefCitation>
|
||
). Their ion mass spectra contained the deprotonated molecules [M
|
||
<emphasis id="E7B3FF3FC913FFEF241BF8FCFE9E8B67" box="[283,300,1793,1812]" italics="true" pageId="2" pageNumber="118">—</emphasis>
|
||
<collectionCode id="B3D6BBE8C913FFEF242CF8FCFE8C8B67" box="[300,318,1793,1812]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="2" pageNumber="118" type="Herbarium">H</collectionCode>
|
||
]
|
||
<emphasis id="E7B3FF3FC913FFEF2444F901FEE28B7A" box="[324,336,1788,1801]" italics="true" pageId="2" pageNumber="118">
|
||
<superScript id="22B28E65C913FFEF2444F901FEE28B7A" attach="left" box="[324,336,1788,1801]" fontSize="5" pageId="2" pageNumber="118">—</superScript>
|
||
</emphasis>
|
||
at
|
||
<emphasis id="E7B3FF3FC913FFEF246DF8FDFE328B67" box="[365,384,1792,1812]" italics="true" pageId="2" pageNumber="118">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC913FFEF2488F8FDFE208B67" box="[392,402,1792,1812]" italics="true" pageId="2" pageNumber="118">z</emphasis>
|
||
373 and 407, respectively (
|
||
<tableCitation id="98451696C913FFEF27A0F8FCFD5A8B67" box="[672,744,1793,1812]" captionStart="Table 1" captionStartId="2.[87,131,728,742]" captionTargetPageId="2" captionText="Table 1 Chemical features of compounds isolated from H. physodes thalli. Retention times (R) from the UPLC analysis, UV absorption maxima (λ), molecular ion masses ([M—H] —), and t max relative retention factors (Rf) from the TLC analysis." httpUri="http://table.plazi.org/id/81B873A5C913FFEF2557FD25FE418F60" pageId="2" pageNumber="118" tableUuid="81B873A5C913FFEF2557FD25FE418F60">Table 1</tableCitation>
|
||
). The major fragment ions, which were detected at
|
||
<emphasis id="E7B3FF3FC913FFEF2749F8E1FDEE8B43" box="[585,604,1820,1840]" italics="true" pageId="2" pageNumber="118">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC913FFEF2764F8E1FDDC8B43" box="[612,622,1820,1840]" italics="true" pageId="2" pageNumber="118">z</emphasis>
|
||
195, 177 and 163 for atranorin (Suppl.
|
||
<figureCitation id="4DFC3FA8C913FFEF2459F8C4FE138B3F" box="[345,417,1849,1868]" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="2" pageNumber="118">Fig. S1I</figureCitation>
|
||
) and at
|
||
<emphasis id="E7B3FF3FC913FFEF24F6F8C5FDBB8B3F" box="[502,521,1848,1868]" italics="true" pageId="2" pageNumber="118">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC913FFEF2710F8C5FDA88B3F" box="[528,538,1848,1868]" italics="true" pageId="2" pageNumber="118">z</emphasis>
|
||
211, 195 and 163 for chloroatranorin (Suppl.
|
||
<figureCitation id="4DFC3FA8C913FFEF2451F8A8FE2F8B1B" box="[337,413,1877,1896]" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="2" pageNumber="118">Fig. S1J</figureCitation>
|
||
), were consistent with the data reported by
|
||
<bibRefCitation id="B1565EDCC913FFEF25E3F88CFE608BF7" author="Hiserodt, R. D. & Swijter, D. F. H. & Mussinan, C. J." box="[227,466,1905,1924]" pageId="2" pageNumber="118" pagination="103 - 111" refId="ref7887" refString="Hiserodt, R. D., Swijter, D. F. H., Mussinan, C. J., 2000. Identification of atranorin and related potential allergens in oakmoss absolute by high-performance liquid chromatography - tandem mass spectrometry using negative ion atmospheric pressure chemical ionization. J. Chromatogr. A 888, 103 - 111." type="journal article" year="2000">Hiserodt et al. (2000)</bibRefCitation>
|
||
and
|
||
<bibRefCitation id="B1565EDCC913FFEF2713F88CFF288BEC" author="Huneck, S. & Schmidt, J." pageId="2" pageNumber="118" pagination="199 - 203" refId="ref8003" refString="Huneck, S., Schmidt, J., 2006. Phenolische Verbindungen einiger Flechten aus der Familie Physciaceae. Herzogia 19, 199 - 203." type="journal article" year="2006">Huneck and Schmidt (2006)</bibRefCitation>
|
||
. The product ions at
|
||
<emphasis id="E7B3FF3FC913FFEF246CF876FECD8BEC" box="[364,383,1931,1951]" italics="true" pageId="2" pageNumber="118">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC913FFEF2487F876FE238BEC" box="[391,401,1931,1951]" italics="true" pageId="2" pageNumber="118">z</emphasis>
|
||
177 (atranorin) or 211 (chloroatranorin) and 195 originated from the cleavage of the ester bond of the molecule (
|
||
<figureCitation id="4DFC3FA8C913FFEF25EAF839FE938BA4" box="[234,289,1988,2007]" captionStart="Fig" captionStartId="4.[321,347,1999,2013]" captionTargetBox="[323,1238,1432,1968]" captionTargetId="graphics-783@4.[601,834,1663,1752]" captionTargetPageId="4" captionText="Fig. 4. Proposed scheme of fragmentation pathways of compounds: hp9 – atranorin and hp10 – chloroatranorin." figureDoi="http://doi.org/10.5281/zenodo.10488555" httpUri="https://zenodo.org/record/10488555/files/figure.png" pageId="2" pageNumber="118">Fig. 4</figureCitation>
|
||
). The product ion at
|
||
<emphasis id="E7B3FF3FC913FFEF24F8F83EFDB98BA4" box="[504,523,1987,2007]" italics="true" pageId="2" pageNumber="118">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC913FFEF2712F83EFDAE8BA4" box="[530,540,1987,2007]" italics="true" pageId="2" pageNumber="118">z</emphasis>
|
||
163 present for both compounds was produced by the loss of methanol from the ion at
|
||
<emphasis id="E7B3FF3FC913FFEF2625FA84FC8A89FE" box="[805,824,1401,1421]" italics="true" pageId="2" pageNumber="118">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC913FFEF263FFA84FCFB89FE" box="[831,841,1401,1421]" italics="true" pageId="2" pageNumber="118">z</emphasis>
|
||
195. The relative retention factor (
|
||
<emphasis id="E7B3FF3FC913FFEF21B8FA84FB7889FC" box="[1208,1226,1401,1423]" italics="true" pageId="2" pageNumber="118">
|
||
<subScript id="49432168C913FFEF21B8FA84FB7889FC" attach="left" box="[1208,1226,1401,1423]" fontSize="5" pageId="2" pageNumber="118">Rf</subScript>
|
||
</emphasis>
|
||
) obtained from the TLC analysis for atranorin (
|
||
<tableCitation id="98451696C913FFEF210AFA6BFBE689DA" box="[1034,1108,1430,1449]" captionStart="Table 1" captionStartId="2.[87,131,728,742]" captionTargetPageId="2" captionText="Table 1 Chemical features of compounds isolated from H. physodes thalli. Retention times (R) from the UPLC analysis, UV absorption maxima (λ), molecular ion masses ([M—H] —), and t max relative retention factors (Rf) from the TLC analysis." httpUri="http://table.plazi.org/id/81B873A5C913FFEF2557FD25FE418F60" pageId="2" pageNumber="118" tableUuid="81B873A5C913FFEF2557FD25FE418F60">Table 1</tableCitation>
|
||
) was consistent with that described by
|
||
<bibRefCitation id="B1565EDCC913FFEF2644FA4FFBBD89B6" author="Orange, A. & James, P. W. & White, F. J." box="[836,1039,1458,1478]" pageId="2" pageNumber="118" refId="ref8753" refString="Orange, A., James, P. W., White, F. J., 2001. Microchemical Methods for the Identification of Lichens. British Lichen Society, London." type="book" year="2001">Orange et al. (2001)</bibRefCitation>
|
||
. Chloroatranorin was not detected.
|
||
</paragraph>
|
||
<paragraph id="D578232DC913FFEE2644FA33FBD88A20" blockId="2.[805,1475,1374,2008]" lastBlockId="3.[831,1500,1572,1619]" lastPageId="3" lastPageNumber="119" pageId="2" pageNumber="118">
|
||
In these analyses, we used a liquid chromatography–tandem mass spectrometry (LC–
|
||
<collectionCode id="B3D6BBE8C913FFEF2127FA17FBF5898E" box="[1063,1095,1514,1533]" country="Italy" lsid="urn:lsid:biocol.org:col:14396" name="Herbarium Messanaensis, Università di Messina" pageId="2" pageNumber="118" type="Herbarium">MS</collectionCode>
|
||
/
|
||
<collectionCode id="B3D6BBE8C913FFEF214EFA17FBDC898E" box="[1102,1134,1514,1533]" country="Italy" lsid="urn:lsid:biocol.org:col:14396" name="Herbarium Messanaensis, Università di Messina" pageId="2" pageNumber="118" type="Herbarium">MS</collectionCode>
|
||
) method in negative ionisation mode, in which data for lichen metabolites were hardly available compared to data gained by positive ionisation mode (
|
||
<bibRefCitation id="B1565EDCC913FFEF2076F9DFFC488A22" author="Huneck, S. & Yoshimura, I." pageId="2" pageNumber="118" refId="ref8031" refString="Huneck, S., Yoshimura, I., 1996. Identification of Lichen Substances. Springer Verlag, Berlin." type="book" year="1996">Huneck and Yoshimura, 1996</bibRefCitation>
|
||
). The obtained results for some of the
|
||
<taxonomicName id="12C758AEC913FFEF207BF9C0FC7E8A1E" class="Lecanoromycetes" family="Parmeliaceae" genus="Hypogymnia" kingdom="Fungi" order="Lecanorales" pageId="2" pageNumber="119" phylum="Ascomycota" rank="subSpecies" species="physodes" subSpecies="secondary">
|
||
<emphasis id="E7B3FF3FC913FFEF207BF9C0FCEB8A1E" italics="true" pageId="2" pageNumber="118">H. physodes</emphasis>
|
||
secondary
|
||
</taxonomicName>
|
||
compounds (protocetraric acid, atranorin and chloroatranorin) were similar to previous reports (
|
||
<bibRefCitation id="B1565EDCC913FFEF202CF988FCE98AD6" author="Hiserodt, R. D. & Swijter, D. F. H. & Mussinan, C. J." pageId="2" pageNumber="118" pagination="103 - 111" refId="ref7887" refString="Hiserodt, R. D., Swijter, D. F. H., Mussinan, C. J., 2000. Identification of atranorin and related potential allergens in oakmoss absolute by high-performance liquid chromatography - tandem mass spectrometry using negative ion atmospheric pressure chemical ionization. J. Chromatogr. A 888, 103 - 111." type="journal article" year="2000">Hiserodt et al., 2000</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="B1565EDCC913FFEF266AF96CFB3C8AD7" author="Huneck, S. & Schmidt, J." box="[874,1166,1681,1700]" pageId="2" pageNumber="118" pagination="199 - 203" refId="ref8003" refString="Huneck, S., Schmidt, J., 2006. Phenolische Verbindungen einiger Flechten aus der Familie Physciaceae. Herzogia 19, 199 - 203." type="journal article" year="2006">Huneck and Schmidt, 2006</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="B1565EDCC913FFEF219EF96CFAC68AD6" author="Huneck, S. & Feige, G. B. & Schmidt, J." box="[1182,1396,1681,1701]" pageId="2" pageNumber="118" pagination="51 - 58" refId="ref8053" refString="Huneck, S., Feige, G. B., Schmidt, J., 2004. Chemie von Cladonia furcata und Cladonia rangiformis. Herzogia 17, 51 - 58." type="journal article" year="2004">Huneck et al., 2004</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="B1565EDCC913FFEF2084F96FFC208AB3" author="Parrot, D. & Jan, S. & Baert, N. & Guyot, S. & Tomasi, S." pageId="2" pageNumber="118" pagination="114 - 124" refId="ref8788" refString="Parrot, D., Jan, S., Baert, N., Guyot, S., Tomasi, S., 2013. Comparative metabolite profiling and chemical study of Ramalina siliquosa complex using LC - ESI-MS / MS approach. Phytochemistry 89, 114 - 124." type="journal article" year="2013">Parrot et al., 2013</bibRefCitation>
|
||
). For the others acids (conphysodalic, physodalic, 3-hydroxyphysodic, 4-
|
||
<emphasis id="E7B3FF3FC913FFEF26DAF935FC5B8AAF" box="[986,1001,1736,1756]" italics="true" pageId="2" pageNumber="118">
|
||
<collectionCode id="B3D6BBE8C913FFEF26DAF935FC5B8AAF" box="[986,1001,1736,1756]" country="Norway" lsid="urn:lsid:biocol.org:col:13093" name="Botanical Museum - University of Oslo" pageId="2" pageNumber="118" type="Herbarium">O</collectionCode>
|
||
</emphasis>
|
||
-methylphysodic, 2
|
||
<emphasis id="E7B3FF3FC913FFEF21ABF93AFB7A8AAF" box="[1195,1224,1735,1757]" italics="true" pageId="2" pageNumber="118">
|
||
<superScript id="22B28E65C913FFEF21ABF93AFB1D8AA0" attach="none" box="[1195,1199,1735,1747]" fontSize="5" pageId="2" pageNumber="118">0</superScript>
|
||
-
|
||
<collectionCode id="B3D6BBE8C913FFEF21B9F935FB7A8AAF" box="[1209,1224,1736,1756]" country="Norway" lsid="urn:lsid:biocol.org:col:13093" name="Botanical Museum - University of Oslo" pageId="2" pageNumber="118" type="Herbarium">O</collectionCode>
|
||
</emphasis>
|
||
-methylphysodic, physodic and
|
||
<emphasis id="E7B3FF3FC913FFEF2675F91EFC308A8B" bold="true" box="[885,898,1763,1784]" italics="true" pageId="2" pageNumber="118">OE</emphasis>
|
||
-alectoronic), we propose their fragmentation patterns in negative ionisation mode for the first time. The use of a modern sensitive analytical method allowed us to identify three additional metabolites of the lichen, i.e., conphysodalic,
|
||
<emphasis id="E7B3FF3FC913FFEF21EFF8CAFB4E8B3F" bold="true" box="[1263,1276,1847,1868]" italics="true" pageId="2" pageNumber="118">OE</emphasis>
|
||
-alectoronic, and 4-
|
||
<emphasis id="E7B3FF3FC913FFEF2625F8A9FC868B1B" box="[805,820,1876,1896]" italics="true" pageId="2" pageNumber="118">
|
||
<collectionCode id="B3D6BBE8C913FFEF2625F8A9FC868B1B" box="[805,820,1876,1896]" country="Norway" lsid="urn:lsid:biocol.org:col:13093" name="Botanical Museum - University of Oslo" pageId="2" pageNumber="118" type="Herbarium">O</collectionCode>
|
||
</emphasis>
|
||
-methylphysodic acids, which accumulated in thalli in minor or trace amounts (
|
||
<figureCitation id="4DFC3FA8C913FFEF26C3F88CFC4B8BF7" box="[963,1017,1905,1924]" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="2" pageNumber="118">Fig. 1</figureCitation>
|
||
). To the best of our knowledge,
|
||
<emphasis id="E7B3FF3FC913FFEF203DF892FAF88BF7" bold="true" box="[1341,1354,1903,1924]" italics="true" pageId="2" pageNumber="118">OE</emphasis>
|
||
-alectoronic acid has been previously described only in some species of the genus
|
||
<taxonomicName id="12C758AEC913FFEF2668F85AFC508BC8" box="[872,994,1959,1979]" class="Lecanoromycetes" family="Parmeliaceae" genus="Hypogymnia" kingdom="Fungi" order="Lecanorales" pageId="2" pageNumber="118" phylum="Ascomycota" rank="genus">
|
||
<emphasis id="E7B3FF3FC913FFEF2668F85AFC508BC8" box="[872,994,1959,1979]" italics="true" pageId="2" pageNumber="118">Hypogymnia</emphasis>
|
||
</taxonomicName>
|
||
growing in Australasia (
|
||
<bibRefCitation id="B1565EDCC913FFEF21DFF855FA078BC8" author="Elix, J. A. & James, P. W." box="[1247,1461,1960,1980]" pageId="2" pageNumber="118" pagination="200 - 246" refId="ref7645" refString="Elix, J. A., James, P. W., 1992. Hypogymniaceae. Fl. Australia 54, 200 - 246." type="journal article" year="1992">Elix and James, 1992</bibRefCitation>
|
||
). However, to date, none of these compounds has been identified in the lichen
|
||
<taxonomicName id="12C758AEC912FFEE25F2F9DEFED18A44" box="[242,355,1571,1591]" class="Lecanoromycetes" family="Parmeliaceae" genus="Hypogymnia" kingdom="Fungi" order="Lecanorales" pageId="3" pageNumber="119" phylum="Ascomycota" rank="species" species="physodes">
|
||
<emphasis id="E7B3FF3FC912FFEE25F2F9DEFED18A44" box="[242,355,1571,1591]" italics="true" pageId="3" pageNumber="119">H. physodes</emphasis>
|
||
</taxonomicName>
|
||
. All seven well-known secondary products of
|
||
<taxonomicName id="12C758AEC912FFEE258EF9C2FEB08A20" box="[142,258,1599,1619]" class="Lecanoromycetes" family="Parmeliaceae" genus="Hypogymnia" kingdom="Fungi" order="Lecanorales" pageId="3" pageNumber="119" phylum="Ascomycota" rank="species" species="physodes">
|
||
<emphasis id="E7B3FF3FC912FFEE258EF9C2FEB08A20" box="[142,258,1599,1619]" italics="true" pageId="3" pageNumber="119">H. physodes</emphasis>
|
||
</taxonomicName>
|
||
were detected in the present study (
|
||
<tableCitation id="98451696C912FFEE2789F9BDFD668A20" box="[649,724,1600,1619]" captionStart="Table 1" captionStartId="2.[87,131,728,742]" captionTargetPageId="2" captionText="Table 1 Chemical features of compounds isolated from H. physodes thalli. Retention times (R) from the UPLC analysis, UV absorption maxima (λ), molecular ion masses ([M—H] —), and t max relative retention factors (Rf) from the TLC analysis." httpUri="http://table.plazi.org/id/81B873A5C913FFEF2557FD25FE418F60" pageId="3" pageNumber="119" tableUuid="81B873A5C913FFEF2557FD25FE418F60">Table 1</tableCitation>
|
||
). The major compounds were physodalic, 3-hydroxyphysodic and physodic acids (
|
||
<figureCitation id="4DFC3FA8C912FFEE2413F985FEFB8AF8" box="[275,329,1656,1675]" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="3" pageNumber="119">Fig. 1</figureCitation>
|
||
). The present results confirm that this lichen species is qualitatively uniform and has only one chemotype (
|
||
<bibRefCitation id="B1565EDCC912FFEE257AF952FE3F8AB0" author="Molnar, K. & Farkas, E." box="[122,397,1711,1731]" pageId="3" pageNumber="119" pagination="473 - 482" refId="ref8581" refString="Molnar, K., Farkas, E., 2011. Depsides and depsidones in population of the lichen Hypogymnia physodes and its genetic diversity. Ann. Bot. Fenn. 48, 473 - 482." type="journal article" year="2011">Molnár and Farkas, 2011</bibRefCitation>
|
||
). The newly identified compounds belong to characteristic suite of
|
||
<taxonomicName id="12C758AEC912FFEE24B1F937FD3C8AAD" box="[433,654,1738,1758]" class="Lecanoromycetes" family="Parmeliaceae" genus="Hypogymnia" kingdom="Fungi" order="Lecanorales" pageId="3" pageNumber="119" phylum="Ascomycota" rank="subSpecies" species="physodes" subSpecies="secondary">
|
||
<emphasis id="E7B3FF3FC912FFEE24B1F937FD908AAD" box="[433,546,1738,1758]" italics="true" pageId="3" pageNumber="119">H. physodes</emphasis>
|
||
secondary
|
||
</taxonomicName>
|
||
metabolites, but until now, they have remained undetected because they are present in minor or trace amounts and/or as a consequence of equipment limitations. As previously reported for other
|
||
<taxonomicName id="12C758AEC912FFEE27C4F8E3FF178B3D" class="Lecanoromycetes" family="Parmeliaceae" genus="Hypogymnia" kingdom="Fungi" order="Lecanorales" pageId="3" pageNumber="119" phylum="Ascomycota" rank="species" species="physodes">
|
||
<emphasis id="E7B3FF3FC912FFEE27C4F8E3FF178B3D" italics="true" pageId="3" pageNumber="119">H. physodes</emphasis>
|
||
</taxonomicName>
|
||
metabolites, the content of these new substances in thalli may be modified by environmental factors such as light, UV radiation, temperature, air pollution, seasonal changes and geographical localisation (
|
||
<bibRefCitation id="B1565EDCC912FFEE25FBF872FD958BD1" author="Bialonska, D. & Dayan, F. E." box="[251,551,1935,1954]" pageId="3" pageNumber="119" pagination="2975 - 2991" refId="ref7317" refString="Bialonska, D., Dayan, F. E., 2005. Chemistry of the lichen Hypogymnia physodes transplanted to an industrial region. J. Chem. Ecol. 31, 2975 - 2991." type="journal article" year="2005">Białońska and Dayan, 2005</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="B1565EDCC912FFEE273AF872FCB98BD1" author="Hauck, M. & Boning, J. & Jacob, M. & Dittrich, S. & Feussner, I. & Leuschner, C." box="[570,779,1935,1954]" pageId="3" pageNumber="119" pagination="58 - 63" refId="ref7760" refString="Hauck, M., Boning, J., Jacob, M., Dittrich, S., Feussner, I., Leuschner, C., 2013. Lichen substance concentrations in the lichen Hypogymnia physodes are correlated with heavy metal concentrations in the substratum. Environ. Exp. Bot. 85, 58 - 63." type="journal article" year="2013">Hauck et al., 2013</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="B1565EDCC912FFEE2571F857FE808BCD" author="Solhaug, K. A. & Lind, M. & Nybakken, L. & Gauslaa, Y." box="[113,306,1962,1982]" pageId="3" pageNumber="119" pagination="40 - 48" refId="ref8994" refString="Solhaug, K. A., Lind, M., Nybakken, L., Gauslaa, Y., 2009. Possible functional roles of cortical depsides and medullary depsidones in the foliose lichen Hypogymnia physodes. Flora 204, 40 - 48." type="journal article" year="2009">Solhaug et al., 2009</bibRefCitation>
|
||
). Therefore, in some cases, these can be present in amounts that are below the limit of detection. Alternatively, these may occur as accessory substances, which are not consistently present in this species.
|
||
</paragraph>
|
||
<caption id="81B873A5C912FFEE25D1FA26FACC899A" ID-DOI="http://doi.org/10.5281/zenodo.10488553" ID-Zenodo-Dep="10488553" box="[209,1406,1499,1514]" httpUri="https://zenodo.org/record/10488553/files/figure.png" pageId="3" pageNumber="119" startId="3.[209,235,1499,1513]" targetBox="[287,1324,184,1469]" targetPageId="3" targetType="figure">
|
||
<paragraph id="D578232DC912FFEE25D1FA26FACC899A" blockId="3.[209,1406,1499,1514]" box="[209,1406,1499,1514]" pageId="3" pageNumber="119">
|
||
<emphasis id="E7B3FF3FC912FFEE25D1FA26FEB1899A" bold="true" box="[209,259,1499,1513]" pageId="3" pageNumber="119">Fig. 2.</emphasis>
|
||
Proposed scheme of fragmentation pathways of compounds: hp1 – conphysodalic acid; hp2 – protocetraric acid and hp3 – physodalic acid.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="D578232DC912FFEE263FF981FA748AE3" blockId="3.[831,1478,1660,1680]" box="[831,1478,1660,1680]" pageId="3" pageNumber="119">
|
||
<heading id="8E309441C912FFEE263FF981FA748AE3" box="[831,1478,1660,1680]" centered="true" fontSize="36" level="2" pageId="3" pageNumber="119" reason="3">
|
||
<emphasis id="E7B3FF3FC912FFEE263FF981FA748AE3" box="[831,1478,1660,1680]" italics="true" pageId="3" pageNumber="119">
|
||
2.2. Detection of
|
||
<taxonomicName id="12C758AEC912FFEE26E4F981FB0D8AE3" box="[996,1215,1660,1680]" class="Lecanoromycetes" family="Parmeliaceae" genus="Hypogymnia" kingdom="Fungi" order="Lecanorales" pageId="3" pageNumber="119" phylum="Ascomycota" rank="subSpecies" species="physodes" subSpecies="secondary">H. physodes secondary</taxonomicName>
|
||
metabolites in spruce bark
|
||
</emphasis>
|
||
</heading>
|
||
</paragraph>
|
||
<paragraph id="D578232DC912FFE8265EF949FE838825" blockId="3.[831,1501,1716,2015]" lastBlockId="5.[113,784,1062,2003]" lastPageId="5" lastPageNumber="121" pageId="3" pageNumber="119">
|
||
The UPLC chromatogram of spruce bark extract at
|
||
<quantity id="123F8EC8C912FFEE208FF949FA6E8ABB" box="[1423,1500,1716,1736]" metricMagnitude="-7" metricUnit="m" metricValue="2.54" pageId="3" pageNumber="119" unit="nm" value="254.0">254 nm</quantity>
|
||
revealed many peaks of unknown substances in the range of retention times from 1.4 to 3.7 min and from 9.6 to 10.8 min (
|
||
<figureCitation id="4DFC3FA8C912FFEE2073F911FA0B8A8C" box="[1395,1465,1772,1791]" captionStart="Fig" captionStartId="5.[113,139,968,982]" captionTargetBox="[155,1484,177,953]" captionTargetId="figure-771@5.[204,1406,181,938]" captionTargetPageId="5" captionText="Fig. 5. Chromatograms of extracts of spruce bark with lichen thalli (A) and without lichens – control (B) monitored at 254 nm. The inside of the flats enlarged range at Rt 4.0–9.5 min." figureDoi="http://doi.org/10.5281/zenodo.10488557" httpUri="https://zenodo.org/record/10488557/files/figure.png" pageId="3" pageNumber="119">Fig. 5A</figureCitation>
|
||
). In these two parts of the chromatogram, there were several intense peaks (e.g.,
|
||
<emphasis id="E7B3FF3FC912FFEE26B5F8DEFC758B49" box="[949,967,1827,1850]" italics="true" pageId="3" pageNumber="119">
|
||
<subScript id="49432168C912FFEE26B5F8DEFC758B49" attach="left" box="[949,967,1827,1850]" fontSize="5" pageId="3" pageNumber="119">Rt</subScript>
|
||
</emphasis>
|
||
at 2.6, 3.2, 9.8, and 10.3 min), which seemed to correspond with the characteristic components of the bark. They also appeared in the control bark of spruce branches (but in relatively lower amounts) (
|
||
<figureCitation id="4DFC3FA8C912FFEE26EDF885FB818BF8" box="[1005,1075,1912,1931]" captionStart="Fig" captionStartId="5.[113,139,968,982]" captionTargetBox="[155,1484,177,953]" captionTargetId="figure-771@5.[204,1406,181,938]" captionTargetPageId="5" captionText="Fig. 5. Chromatograms of extracts of spruce bark with lichen thalli (A) and without lichens – control (B) monitored at 254 nm. The inside of the flats enlarged range at Rt 4.0–9.5 min." figureDoi="http://doi.org/10.5281/zenodo.10488557" httpUri="https://zenodo.org/record/10488557/files/figure.png" pageId="3" pageNumber="119">Fig. 5B</figureCitation>
|
||
), however they were absent in the extract of the lichen thalli (
|
||
<figureCitation id="4DFC3FA8C912FFEE210EF869FBF48BD4" box="[1038,1094,1940,1959]" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="3" pageNumber="119">Fig. 1</figureCitation>
|
||
). These substances likely belong to the plant phenolic compounds, which have been shown to be accumulated into a higher extent in the spruce bark covered with the lichen
|
||
<taxonomicName id="12C758AEC914FFE825B4FBDBFDAA8849" ID-CoL="6MR42" authority="(Latkowska et al., 2015)" baseAuthorityName="Latkowska" baseAuthorityYear="2015" box="[180,536,1062,1083]" class="Lecanoromycetes" family="Parmeliaceae" genus="Hypogymnia" kingdom="Fungi" order="Lecanorales" pageId="5" pageNumber="121" phylum="Ascomycota" rank="species" species="physodes">
|
||
<emphasis id="E7B3FF3FC914FFE825B4FBDBFE978849" box="[180,293,1062,1082]" italics="true" pageId="5" pageNumber="121">H. physodes</emphasis>
|
||
(
|
||
<bibRefCitation id="B1565EDCC914FFE82433FBDAFDA38849" author="Latkowska, E. & Chrapusta, E. & Bober, B. & Kaminski, A. & Adamski, M. & Bialczyk, J." box="[307,529,1063,1083]" pageId="5" pageNumber="121" pagination="129 - 138" refId="ref8128" refString="Latkowska, E., Chrapusta, E., Bober, B., Kaminski, A., Adamski, M., Bialczyk, J., 2015. Allelopathic effects of epiphytic lichen Hypogymnia physodes (L.) Nyl. colonization on the spruce (Picea abies (L.) Karst.) bark. Allelopathy J. 35, 129 - 138." type="journal article" year="2015">Latkowska et al., 2015</bibRefCitation>
|
||
)
|
||
</taxonomicName>
|
||
as a response of the tree to lichen infection.
|
||
</paragraph>
|
||
<caption id="81B873A5C915FFE92557FAFDFE618956" ID-DOI="http://doi.org/10.5281/zenodo.10530148" ID-Zenodo-Dep="10530148" httpUri="https://zenodo.org/record/10530148/files/figure.png" pageId="4" pageNumber="120" startId="4.[87,113,1280,1294]" targetBox="[299,1255,184,1265]" targetPageId="4" targetType="figure">
|
||
<paragraph id="D578232DC915FFE92557FAFDFE618956" blockId="4.[87,1475,1278,1319]" pageId="4" pageNumber="120">
|
||
<emphasis id="E7B3FF3FC915FFE92557FAFDFF39897D" bold="true" box="[87,139,1280,1294]" pageId="4" pageNumber="120">Fig. 3.</emphasis>
|
||
Proposed scheme of fragmentation pathways of compounds: hp4 – 3-hydroxyphysodic acid; hp5 – 4-
|
||
<emphasis id="E7B3FF3FC915FFE926E7FB02FC41897C" box="[999,1011,1279,1295]" italics="true" pageId="4" pageNumber="120">O</emphasis>
|
||
-methylphysodic acid; hp6 – 2
|
||
<emphasis id="E7B3FF3FC915FFE921F4FB03FAB9897C" box="[1268,1291,1278,1295]" italics="true" pageId="4" pageNumber="120">
|
||
<superScript id="22B28E65C915FFE921F4FB03FB4A897B" attach="right" box="[1268,1272,1278,1288]" fontSize="4" pageId="4" pageNumber="120">0</superScript>
|
||
-O
|
||
</emphasis>
|
||
-methylphysodic acid; hp7 – physodic acid; hp8 –
|
||
<emphasis id="E7B3FF3FC915FFE9243BFAE8FEF78954" bold="true" box="[315,325,1301,1319]" italics="true" pageId="4" pageNumber="120">OE</emphasis>
|
||
-alectoronic acid.
|
||
</paragraph>
|
||
</caption>
|
||
<caption id="81B873A5C915FFE92441F832FB688BAE" ID-DOI="http://doi.org/10.5281/zenodo.10488555" ID-Zenodo-Dep="10488555" box="[321,1242,1999,2013]" httpUri="https://zenodo.org/record/10488555/files/figure.png" pageId="4" pageNumber="120" startId="4.[321,347,1999,2013]" targetBox="[323,1238,1432,1968]" targetPageId="4" targetType="figure">
|
||
<paragraph id="D578232DC915FFE92441F832FB688BAE" blockId="4.[321,1242,1999,2013]" box="[321,1242,1999,2013]" pageId="4" pageNumber="120">
|
||
<emphasis id="E7B3FF3FC915FFE92441F832FEC18BAE" bold="true" box="[321,371,1999,2013]" pageId="4" pageNumber="120">Fig. 4.</emphasis>
|
||
Proposed scheme of fragmentation pathways of compounds: hp9 – atranorin and hp10 – chloroatranorin.
|
||
</paragraph>
|
||
</caption>
|
||
<caption id="81B873A5C914FFE82571FC35FF598F9E" ID-DOI="http://doi.org/10.5281/zenodo.10488557" ID-Zenodo-Dep="10488557" httpUri="https://zenodo.org/record/10488557/files/figure.png" pageId="5" pageNumber="121" startId="5.[113,139,968,982]" targetBox="[155,1484,177,953]" targetPageId="5" targetType="figure">
|
||
<paragraph id="D578232DC914FFE82571FC35FF598F9E" blockId="5.[113,1501,968,1007]" pageId="5" pageNumber="121">
|
||
<emphasis id="E7B3FF3FC914FFE82571FC35FF168FA5" bold="true" box="[113,164,968,982]" pageId="5" pageNumber="121">Fig. 5.</emphasis>
|
||
Chromatograms of extracts of spruce bark with lichen thalli (A) and without lichens – control (B) monitored at 254 nm. The inside of the flats enlarged range at
|
||
<emphasis id="E7B3FF3FC914FFE82571FC23FF338F9C" box="[113,129,990,1007]" italics="true" pageId="5" pageNumber="121">
|
||
<subScript id="49432168C914FFE82571FC23FF338F9C" attach="left" box="[113,129,990,1007]" fontSize="4" pageId="5" pageNumber="121">Rt</subScript>
|
||
</emphasis>
|
||
4.0–9.5 min.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="D578232DC914FFE82591FBA2FF428B0C" blockId="5.[113,784,1062,2003]" pageId="5" pageNumber="121">
|
||
In addition to plant phenolics, a few lichen metabolites were detected in the samples of bark of the branch colonised by
|
||
<taxonomicName id="12C758AEC914FFE827C7FB87FF1788D9" ID-CoL="6MR42" class="Lecanoromycetes" family="Parmeliaceae" genus="Hypogymnia" kingdom="Fungi" order="Lecanorales" pageId="5" pageNumber="121" phylum="Ascomycota" rank="species" species="physodes">
|
||
<emphasis id="E7B3FF3FC914FFE827C7FB87FF1788D9" italics="true" pageId="5" pageNumber="121">H. physodes</emphasis>
|
||
</taxonomicName>
|
||
thalli. The peaks detected at retention times of 6.1 (hp3), 6.9 (hp4), 7.6 (hp7) and 8.8 (hp9) min (
|
||
<figureCitation id="4DFC3FA8C914FFE824DAFB4EFD9388B5" box="[474,545,1203,1222]" captionStart="Fig" captionStartId="5.[113,139,968,982]" captionTargetBox="[155,1484,177,953]" captionTargetId="figure-771@5.[204,1406,181,938]" captionTargetPageId="5" captionText="Fig. 5. Chromatograms of extracts of spruce bark with lichen thalli (A) and without lichens – control (B) monitored at 254 nm. The inside of the flats enlarged range at Rt 4.0–9.5 min." figureDoi="http://doi.org/10.5281/zenodo.10488557" httpUri="https://zenodo.org/record/10488557/files/figure.png" pageId="5" pageNumber="121">Fig. 5A</figureCitation>
|
||
), which were displayed in the MS analysis as deprotonated molecules at
|
||
<emphasis id="E7B3FF3FC914FFE8275CFB33FDDD8891" box="[604,623,1230,1250]" italics="true" pageId="5" pageNumber="121">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC914FFE82777FB33FD338891" box="[631,641,1230,1250]" italics="true" pageId="5" pageNumber="121">z</emphasis>
|
||
415, 485, 469 and 373 (Suppl.
|
||
<figureCitation id="4DFC3FA8C914FFE82416FB16FEEA888D" box="[278,344,1259,1278]" captionStart="Fig" captionStartId="3.[209,235,1499,1513]" captionTargetBox="[287,1324,184,1469]" captionTargetId="graphics-370@3.[353,1209,280,1212]" captionTargetPageId="3" captionText="Fig. 2. Proposed scheme of fragmentation pathways of compounds: hp1 – conphysodalic acid; hp2 – protocetraric acid and hp3 – physodalic acid." figureDoi="http://doi.org/10.5281/zenodo.10488553" httpUri="https://zenodo.org/record/10488553/files/figure.png" pageId="5" pageNumber="121">Fig. S2</figureCitation>
|
||
), were recognised as physodalic, 3-hydroxyphysodic, physodic acids and atranorin, respectively. Both the retention times and molecular masses of the compounds were consistent with those obtained for the corresponding substances in the extract of the lichen thalli (
|
||
<tableCitation id="98451696C914FFE82484FAA7FE7C891E" box="[388,462,1370,1389]" captionStart="Table 1" captionStartId="2.[87,131,728,742]" captionTargetPageId="2" captionText="Table 1 Chemical features of compounds isolated from H. physodes thalli. Retention times (R) from the UPLC analysis, UV absorption maxima (λ), molecular ion masses ([M—H] —), and t max relative retention factors (Rf) from the TLC analysis." httpUri="http://table.plazi.org/id/81B873A5C913FFEF2557FD25FE418F60" pageId="5" pageNumber="121" tableUuid="81B873A5C913FFEF2557FD25FE418F60">Table 1</tableCitation>
|
||
). Moreover, their fragment ions (Suppl.
|
||
<figureCitation id="4DFC3FA8C914FFE825BEFA8BFF4C89FA" box="[190,254,1398,1417]" captionStart="Fig" captionStartId="3.[209,235,1499,1513]" captionTargetBox="[287,1324,184,1469]" captionTargetId="graphics-370@3.[353,1209,280,1212]" captionTargetPageId="3" captionText="Fig. 2. Proposed scheme of fragmentation pathways of compounds: hp1 – conphysodalic acid; hp2 – protocetraric acid and hp3 – physodalic acid." figureDoi="http://doi.org/10.5281/zenodo.10488553" httpUri="https://zenodo.org/record/10488553/files/figure.png" pageId="5" pageNumber="121">Fig. S2</figureCitation>
|
||
) were compatible with those obtained for the corresponding compounds from lichen thalli (Suppl.
|
||
<figureCitation id="4DFC3FA8C914FFE82753FA6FFD2689D6" box="[595,660,1426,1445]" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="5" pageNumber="121">Fig. S1</figureCitation>
|
||
). For example, in the MS/MS spectrum of physodalic acid, characteristic daughter ions were observed at
|
||
<emphasis id="E7B3FF3FC914FFE824CFFA34FE5089AE" box="[463,482,1481,1501]" italics="true" pageId="5" pageNumber="121">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC914FFE824EAFA34FE4689AE" box="[490,500,1481,1501]" italics="true" pageId="5" pageNumber="121">z</emphasis>
|
||
355, 311 and 267 (Suppl.
|
||
<figureCitation id="4DFC3FA8C914FFE82571FA1BFF4B898A" box="[113,249,1510,1529]" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="5" pageNumber="121">Fig. S1C and S</figureCitation>
|
||
<figureCitation id="4DFC3FA8C914FFE825F9FA1BFEA6898A" box="[249,276,1510,1529]" captionStart="Fig" captionStartId="3.[209,235,1499,1513]" captionTargetBox="[287,1324,184,1469]" captionTargetId="graphics-370@3.[353,1209,280,1212]" captionTargetPageId="3" captionText="Fig. 2. Proposed scheme of fragmentation pathways of compounds: hp1 – conphysodalic acid; hp2 – protocetraric acid and hp3 – physodalic acid." figureDoi="http://doi.org/10.5281/zenodo.10488553" httpUri="https://zenodo.org/record/10488553/files/figure.png" pageId="5" pageNumber="121">2A</figureCitation>
|
||
), corresponding to the sequential loss of
|
||
<collectingCountry id="ADD063BDC914FFE827ABFA1BFD7A898A" box="[683,712,1510,1529]" name="Switzerland" pageId="5" pageNumber="121">CH</collectingCountry>
|
||
<subScript id="49432168C914FFE827C9FA12FD608988" attach="right" box="[713,722,1519,1531]" fontSize="5" pageId="5" pageNumber="121">3</subScript>
|
||
COOH and two CO
|
||
<subScript id="49432168C914FFE825E6F9F6FF5D8A64" attach="left" box="[230,239,1547,1559]" fontSize="5" pageId="5" pageNumber="121">2</subScript>
|
||
groups, respectively. The mass spectrum of 3-hydroxyphysodic acid contained product ions at
|
||
<emphasis id="E7B3FF3FC914FFE8271FF9E1FD808A43" box="[543,562,1564,1584]" italics="true" pageId="5" pageNumber="121">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC914FFE82739F9E1FDF18A43" box="[569,579,1564,1584]" italics="true" pageId="5" pageNumber="121">z</emphasis>
|
||
467, 441, 423, 399, 397 (Suppl.
|
||
<figureCitation id="4DFC3FA8C914FFE825EDF9C4FE8F8A3F" box="[237,317,1593,1612]" captionStart="Fig" captionStartId="3.[209,235,1499,1513]" captionTargetBox="[287,1324,184,1469]" captionTargetId="graphics-370@3.[353,1209,280,1212]" captionTargetPageId="3" captionText="Fig. 2. Proposed scheme of fragmentation pathways of compounds: hp1 – conphysodalic acid; hp2 – protocetraric acid and hp3 – physodalic acid." figureDoi="http://doi.org/10.5281/zenodo.10488553" httpUri="https://zenodo.org/record/10488553/files/figure.png" pageId="5" pageNumber="121">Fig. S2B</figureCitation>
|
||
), all of which have been observed previously in samples of the lichen thalli (Suppl.
|
||
<figureCitation id="4DFC3FA8C914FFE82704F9A8FDEA8A1B" box="[516,600,1621,1640]" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="5" pageNumber="121">Fig. S1D</figureCitation>
|
||
). In addition, the physodic acid isolated from bark samples displayed the formation of typical fragment ions at
|
||
<emphasis id="E7B3FF3FC914FFE82495F971FE1A8AD3" box="[405,424,1676,1696]" italics="true" pageId="5" pageNumber="121">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC914FFE824B0F971FE088AD3" box="[432,442,1676,1696]" italics="true" pageId="5" pageNumber="121">z</emphasis>
|
||
451, 425, 407, 383, 381 (Suppl.
|
||
<figureCitation id="4DFC3FA8C914FFE82571F954FF0C8ACF" box="[113,190,1705,1724]" captionStart="Fig" captionStartId="3.[209,235,1499,1513]" captionTargetBox="[287,1324,184,1469]" captionTargetId="graphics-370@3.[353,1209,280,1212]" captionTargetPageId="3" captionText="Fig. 2. Proposed scheme of fragmentation pathways of compounds: hp1 – conphysodalic acid; hp2 – protocetraric acid and hp3 – physodalic acid." figureDoi="http://doi.org/10.5281/zenodo.10488553" httpUri="https://zenodo.org/record/10488553/files/figure.png" pageId="5" pageNumber="121">Fig. S2C</figureCitation>
|
||
), which were described herein for the samples of the lichen thalli (Suppl.
|
||
<figureCitation id="4DFC3FA8C914FFE825F7F938FEF58AAB" box="[247,327,1733,1752]" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="5" pageNumber="121">Fig. S1G</figureCitation>
|
||
). The mass spectrum of atranorin detected in spruce bark covered by lichen thalli displayed product ions at
|
||
<emphasis id="E7B3FF3FC914FFE827EBF91DFD4C8A87" box="[747,766,1760,1780]" italics="true" pageId="5" pageNumber="121">m</emphasis>
|
||
/
|
||
<emphasis id="E7B3FF3FC914FFE82605F91DFCBD8A87" box="[773,783,1760,1780]" italics="true" pageId="5" pageNumber="121">z</emphasis>
|
||
192, 177 and 162 (Suppl.
|
||
<figureCitation id="4DFC3FA8C914FFE82475F900FE748B63" box="[373,454,1789,1808]" captionStart="Fig" captionStartId="3.[209,235,1499,1513]" captionTargetBox="[287,1324,184,1469]" captionTargetId="graphics-370@3.[353,1209,280,1212]" captionTargetPageId="3" captionText="Fig. 2. Proposed scheme of fragmentation pathways of compounds: hp1 – conphysodalic acid; hp2 – protocetraric acid and hp3 – physodalic acid." figureDoi="http://doi.org/10.5281/zenodo.10488553" httpUri="https://zenodo.org/record/10488553/files/figure.png" pageId="5" pageNumber="121">Fig. S2D</figureCitation>
|
||
). The slight divergences in mass of the fragment ions in comparison to those described in the lichen thali (Suppl.
|
||
<figureCitation id="4DFC3FA8C914FFE825F1F8C9FE8B8B3B" box="[241,313,1844,1864]" captionStart="Fig" captionStartId="2.[212,238,652,666]" captionTargetBox="[171,1380,184,623]" captionTargetId="figure-540@2.[170,1380,181,623]" captionTargetPageId="2" captionText="Fig. 1. Chromatogram of extracts from H. physodes thalli monitored at 254 nm. hp1–hp10 represent analysed lichen secondary metabolites." figureDoi="http://doi.org/10.5281/zenodo.10488551" httpUri="https://zenodo.org/record/10488551/files/figure.png" pageId="5" pageNumber="121">Fig. S1I</figureCitation>
|
||
) may be due to the presence of small amounts of atranorin in the sample, but they are within the limits of error of the analysis.
|
||
</paragraph>
|
||
<paragraph id="D578232DC914FFE82591F875FB8C8922" blockId="5.[113,784,1062,2003]" lastBlockId="5.[831,1501,1063,2003]" pageId="5" pageNumber="121">
|
||
None of the four compounds detected in the bark of spruce branches colonised by
|
||
<taxonomicName id="12C758AEC914FFE82463F85EFE6B8BC4" box="[355,473,1955,1975]" class="Lecanoromycetes" family="Parmeliaceae" genus="Hypogymnia" kingdom="Fungi" order="Lecanorales" pageId="5" pageNumber="121" phylum="Ascomycota" rank="species" species="physodes">
|
||
<emphasis id="E7B3FF3FC914FFE82463F85EFE6B8BC4" box="[355,473,1955,1975]" italics="true" pageId="5" pageNumber="121">H. physodes</emphasis>
|
||
</taxonomicName>
|
||
, or any of the other six secondary metabolites produced by this lichen, have been found in bark without lichen, which served as control (
|
||
<figureCitation id="4DFC3FA8C914FFE82006FBDAFAF98849" box="[1286,1355,1063,1082]" captionStart="Fig" captionStartId="5.[113,139,968,982]" captionTargetBox="[155,1484,177,953]" captionTargetId="figure-771@5.[204,1406,181,938]" captionTargetPageId="5" captionText="Fig. 5. Chromatograms of extracts of spruce bark with lichen thalli (A) and without lichens – control (B) monitored at 254 nm. The inside of the flats enlarged range at Rt 4.0–9.5 min." figureDoi="http://doi.org/10.5281/zenodo.10488557" httpUri="https://zenodo.org/record/10488557/files/figure.png" pageId="5" pageNumber="121">Fig. 5B</figureCitation>
|
||
). The obtained results demonstrate the presence of the lichen secondary metabolites in the spruce bark in direct contact with
|
||
<taxonomicName id="12C758AEC914FFE82005FBA3FAC48801" box="[1285,1398,1118,1138]" class="Lecanoromycetes" family="Parmeliaceae" genus="Hypogymnia" kingdom="Fungi" order="Lecanorales" pageId="5" pageNumber="121" phylum="Ascomycota" rank="species" species="physodes">
|
||
<emphasis id="E7B3FF3FC914FFE82005FBA3FAC48801" box="[1285,1398,1118,1138]" italics="true" pageId="5" pageNumber="121">H. physodes</emphasis>
|
||
</taxonomicName>
|
||
. This may be the result of their translocation from the lichen thalli into the spruce bark and/or their production inside the bark by some hyphae penetrating the tree tissues. The fact, that these substances belong to three different groups of compounds,
|
||
<emphasis id="E7B3FF3FC914FFE82039FB32FAF78891" bold="true" box="[1337,1349,1231,1250]" italics="true" pageId="5" pageNumber="121">β</emphasis>
|
||
-orcinol depsidones (physodalic acid), orcinol depsidones (3-hydroxyphysodic acid and physodic acid) and
|
||
<emphasis id="E7B3FF3FC914FFE8216FFAFAFBC98969" bold="true" box="[1135,1147,1287,1306]" italics="true" pageId="5" pageNumber="121">β</emphasis>
|
||
-orcinol
|
||
<emphasis id="E7B3FF3FC914FFE821D3FAF8FB4D896A" box="[1235,1279,1285,1305]" italics="true" pageId="5" pageNumber="121">para</emphasis>
|
||
-depsides (atranorin), suggests that their molecular structure has insignificant or no effect on their allocation.
|
||
</paragraph>
|
||
<paragraph id="D578232DC914FFEB265EFAA7FF798E1F" blockId="5.[831,1501,1063,2003]" lastBlockId="6.[87,757,182,620]" lastPageId="6" lastPageNumber="122" pageId="5" pageNumber="121">
|
||
The content of
|
||
<taxonomicName id="12C758AEC914FFE826F5FAA4FBD4891E" box="[1013,1126,1369,1389]" class="Lecanoromycetes" family="Parmeliaceae" genus="Hypogymnia" kingdom="Fungi" order="Lecanorales" pageId="5" pageNumber="121" phylum="Ascomycota" rank="species" species="physodes">
|
||
<emphasis id="E7B3FF3FC914FFE826F5FAA4FBD4891E" box="[1013,1126,1369,1389]" italics="true" pageId="5" pageNumber="121">H. physodes</emphasis>
|
||
</taxonomicName>
|
||
depsides and depsidones may represent more than 20% of the dry weight of the thalli (
|
||
<bibRefCitation id="B1565EDCC914FFE8204EFA8BFCC389D6" author="Solhaug, K. A. & Lind, M. & Nybakken, L. & Gauslaa, Y." pageId="5" pageNumber="121" pagination="40 - 48" refId="ref8994" refString="Solhaug, K. A., Lind, M., Nybakken, L., Gauslaa, Y., 2009. Possible functional roles of cortical depsides and medullary depsidones in the foliose lichen Hypogymnia physodes. Flora 204, 40 - 48." type="journal article" year="2009">Solhaug et al., 2009</bibRefCitation>
|
||
). Lichen substances detected in tree bark belong to major secondary metabolites that are produced and accumulated by
|
||
<taxonomicName id="12C758AEC914FFE82095FA50FCC189AE" class="Lecanoromycetes" family="Parmeliaceae" genus="Hypogymnia" kingdom="Fungi" order="Lecanorales" pageId="5" pageNumber="121" phylum="Ascomycota" rank="species" species="physodes">
|
||
<emphasis id="E7B3FF3FC914FFE82095FA50FCC189AE" italics="true" pageId="5" pageNumber="121">H. physodes</emphasis>
|
||
</taxonomicName>
|
||
thalli (
|
||
<bibRefCitation id="B1565EDCC914FFE826C3FA37FB2089AE" author="Solhaug, K. A. & Lind, M. & Nybakken, L. & Gauslaa, Y." box="[963,1170,1482,1501]" pageId="5" pageNumber="121" pagination="40 - 48" refId="ref8994" refString="Solhaug, K. A., Lind, M., Nybakken, L., Gauslaa, Y., 2009. Possible functional roles of cortical depsides and medullary depsidones in the foliose lichen Hypogymnia physodes. Flora 204, 40 - 48." type="journal article" year="2009">Solhaug et al., 2009</bibRefCitation>
|
||
). It seems most likely that the amount of the substances translocated into the tree bark correlates with their quantity in the lichen thalli. The other six minor metabolites of
|
||
<taxonomicName id="12C758AEC914FFE826D5F9E1FBF48A43" box="[981,1094,1564,1584]" class="Lecanoromycetes" family="Parmeliaceae" genus="Hypogymnia" kingdom="Fungi" order="Lecanorales" pageId="5" pageNumber="121" phylum="Ascomycota" rank="species" species="physodes">
|
||
<emphasis id="E7B3FF3FC914FFE826D5F9E1FBF48A43" box="[981,1094,1564,1584]" italics="true" pageId="5" pageNumber="121">H. physodes</emphasis>
|
||
</taxonomicName>
|
||
were not detected in the tree bark samples, likely because they were present at levels below the limit of detection rather than an inability to translocate. The limited amount of the substances translocated into the bark may be also explained by their low or moderate (considering the polar groups on the molecules) solubility in water. Moreover, the lichen substances may undergo enzymatic and/or hydrolytic degradation (
|
||
<bibRefCitation id="B1565EDCC914FFE82647F91CFBB58A87" author="Lawrey, J. D. & Torzilli, A. P. & Chandhoke, V." box="[839,1031,1761,1780]" pageId="5" pageNumber="121" pagination="184 - 189" refId="ref8198" refString="Lawrey, J. D., Torzilli, A. P., Chandhoke, V., 1999. Destruction of lichen chemical defenses by a fungal pathogen. Am. J. Bot. 86, 184 - 189." type="journal article" year="1999">Lawrey et al., 1999</bibRefCitation>
|
||
), but in the present study, we did not investigate the degradation products. Atraric acid, the hydrolysis product of atranorin, has been identified and quantified in cork, sapwood and the outer heartwood of oak trunks colonised by
|
||
<taxonomicName id="12C758AEC914FFE82063F8CEFA6F8B3B" box="[1379,1501,1843,1864]" class="Lecanoromycetes" family="Parmeliaceae" genus="Parmelia" kingdom="Fungi" order="Lecanorales" pageId="5" pageNumber="121" phylum="Ascomycota" rank="species" species="undetermined">
|
||
<emphasis id="E7B3FF3FC914FFE82063F8CEFA0A8B34" box="[1379,1464,1843,1863]" italics="true" pageId="5" pageNumber="121">Parmelia</emphasis>
|
||
sp.
|
||
</taxonomicName>
|
||
(
|
||
<bibRefCitation id="B1565EDCC914FFE82647F8ADFBAF8B10" author="Bourgeois, G. & Suire, C. & Vivas, N. & Vitry, C." box="[839,1053,1872,1892]" pageId="5" pageNumber="121" pagination="281 - 283" refId="ref7355" refString="Bourgeois, G., Suire, C., Vivas, N., Vitry, C., 1999. Atraric acid, a marker for epiphytic lichens in the wood used in cooperage: identification and quantification by GC / MS / (MS). Analusis 27, 281 - 283." type="journal article" year="1999">Bourgeois et al., 1999</bibRefCitation>
|
||
) due to the ability of this lichen to penetrate tree tissues up to the phloem and cambium (
|
||
<bibRefCitation id="B1565EDCC914FFE82023F891FA128B0C" author="Brodo, I. M." box="[1315,1440,1900,1919]" pageId="5" pageNumber="121" pagination="401 - 441" refId="ref7444" refString="Brodo, I. M., 1973. Substrate ecology. In: Ahmadjian, V., Hale, M. E. (Eds.), The Lichens. New York Academic Press, New York, pp. 401 - 441." type="book chapter" year="1973">Brodo, 1973</bibRefCitation>
|
||
). The hyphae of some fruticose lichens such as
|
||
<taxonomicName id="12C758AEC914FFE82004F87AFA038BE8" box="[1284,1457,1927,1947]" class="Lecanoromycetes" family="Parmeliaceae" genus="Evernia" kingdom="Fungi" order="Lecanorales" pageId="5" pageNumber="121" phylum="Ascomycota" rank="species" species="prunastri">
|
||
<emphasis id="E7B3FF3FC914FFE82004F87AFA038BE8" box="[1284,1457,1927,1947]" italics="true" pageId="5" pageNumber="121">Evernia prunastri</emphasis>
|
||
</taxonomicName>
|
||
(L.) Ach. has a compact holdfast that reaches up to the inside of xylem vessels within tree branches (
|
||
<bibRefCitation id="B1565EDCC914FFE82179F83DFA8F8BA0" author="Ascaso, C. & Gonzales, C. & Vicente, C." box="[1145,1341,1984,2003]" pageId="5" pageNumber="121" pagination="43 - 51" refId="ref7223" refString="Ascaso, C., Gonzales, C., Vicente, C., 1980. Epiphytic Evernia prunastri (L.) Ach.: ultrastructural facts. Cryptogamie Bryol. Lichenol. 1, 43 - 51." type="journal article" year="1980">Ascaso et al., 1980</bibRefCitation>
|
||
). Therefore, its main metabolites, evernic, everninic and usnic acids, were present in the xylem sap of oak and birch branches that were richly covered by
|
||
<taxonomicName id="12C758AEC917FFEB25AAFF10FEA88D72" box="[170,282,237,257]" class="Lecanoromycetes" family="Parmeliaceae" genus="Evernia" kingdom="Fungi" order="Lecanorales" pageId="6" pageNumber="122" phylum="Ascomycota" rank="species" species="prunastri">
|
||
<emphasis id="E7B3FF3FC917FFEB25AAFF10FEA88D72" box="[170,282,237,257]" italics="true" pageId="6" pageNumber="122">E. prunastri</emphasis>
|
||
</taxonomicName>
|
||
(
|
||
<bibRefCitation id="B1565EDCC917FFEB2429FF13FE578D72" author="Avalos, A. & Legaz, M. E. & Vicente, C." box="[297,485,238,257]" pageId="6" pageNumber="122" pagination="381 - 384" refId="ref7264" refString="Avalos, A., Legaz, M. E., Vicente, C., 1986. The occurrence of the lichen phenolics in the xylem sap of Quercus pyrenaica, their translocation to leaves and biological significance. Biochem. Syst. Ecol. 14, 381 - 384." type="journal article" year="1986">Avalos et al., 1986</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="B1565EDCC917FFEB24EFFF13FD188D72" author="Monso, M. A. & Legaz, M. E. & Vicente, C." box="[495,682,238,257]" pageId="6" pageNumber="122" pagination="299 - 303" refId="ref8620" refString="Monso, M. A., Legaz, M. E., Vicente, C., 1993. A biochemical approach to the hemiparasitic action of the epiphytic lichen Evernia prunastri on Betula pendula. Ann. Bot. Fenn. 30, 299 - 303." type="journal article" year="1993">Monsó et al., 1993</bibRefCitation>
|
||
). Some of the lichen metabolites were also translocated into the leaves (
|
||
<bibRefCitation id="B1565EDCC917FFEB255FFEDBFEAA8D4A" author="Avalos, A. & Legaz, M. E. & Vicente, C." box="[95,280,294,313]" pageId="6" pageNumber="122" pagination="381 - 384" refId="ref7264" refString="Avalos, A., Legaz, M. E., Vicente, C., 1986. The occurrence of the lichen phenolics in the xylem sap of Quercus pyrenaica, their translocation to leaves and biological significance. Biochem. Syst. Ecol. 14, 381 - 384." type="journal article" year="1986">Avalos et al., 1986</bibRefCitation>
|
||
). The foliose lichen
|
||
<taxonomicName id="12C758AEC917FFEB24E4FED8FDE48D4A" box="[484,598,293,313]" class="Lecanoromycetes" family="Parmeliaceae" genus="Hypogymnia" kingdom="Fungi" order="Lecanorales" pageId="6" pageNumber="122" phylum="Ascomycota" rank="species" species="physodes">
|
||
<emphasis id="E7B3FF3FC917FFEB24E4FED8FDE48D4A" box="[484,598,293,313]" italics="true" pageId="6" pageNumber="122">H. physodes</emphasis>
|
||
</taxonomicName>
|
||
, which belongs to the family
|
||
<taxonomicName id="12C758AEC917FFEB25DDFEBCFEEE8D26" box="[221,348,321,341]" class="Lecanoromycetes" family="Parmeliaceae" kingdom="Fungi" order="Lecanorales" pageId="6" pageNumber="122" phylum="Ascomycota" rank="family">
|
||
<emphasis id="E7B3FF3FC917FFEB25DDFEBCFEEE8D26" box="[221,348,321,341]" italics="true" pageId="6" pageNumber="122">Parmeliaceae</emphasis>
|
||
</taxonomicName>
|
||
, has no specific structure but is typically attached to the substratum by folds or, rarely, by most of the lower cortex (
|
||
<bibRefCitation id="B1565EDCC917FFEB25A6FE84FEEE8DFE" author="Smith, C. W. & Aptroot, A. & Coppins, B. J. & Fletcher, A. & Gilbert, O. L. & James, P. W. & Wolseley, P. A." box="[166,348,377,397]" pageId="6" pageNumber="122" refId="ref8932" refString="Smith, C. W., Aptroot, A., Coppins, B. J., Fletcher, A., Gilbert, O. L., James, P. W., Wolseley, P. A., 2009. The Lichens of Great Britain and Ireland. The British Lichen Society, London." type="book" year="2009">Smith et al., 2009</bibRefCitation>
|
||
). For this reason, it penetrates only the superficial layer of the periderm (
|
||
<bibRefCitation id="B1565EDCC917FFEB24B9FE68FD848DDA" author="Brodo, I. M." box="[441,566,405,425]" pageId="6" pageNumber="122" pagination="401 - 441" refId="ref7444" refString="Brodo, I. M., 1973. Substrate ecology. In: Ahmadjian, V., Hale, M. E. (Eds.), The Lichens. New York Academic Press, New York, pp. 401 - 441." type="book chapter" year="1973">Brodo, 1973</bibRefCitation>
|
||
). Our results confirmed that the secondary metabolites of this lichen species were present in the surrounding host tree tissues. These metabolites might be the cause of the long-lasting negative effects on spruce trees that we have been observed in our previous studies (
|
||
<bibRefCitation id="B1565EDCC917FFEB255FFDDCFEEB8E47" author="Latkowska, E. & Chrapusta, E. & Bober, B. & Kaminski, A. & Adamski, M. & Bialczyk, J." box="[95,345,545,564]" pageId="6" pageNumber="122" pagination="129 - 138" refId="ref8128" refString="Latkowska, E., Chrapusta, E., Bober, B., Kaminski, A., Adamski, M., Bialczyk, J., 2015. Allelopathic effects of epiphytic lichen Hypogymnia physodes (L.) Nyl. colonization on the spruce (Picea abies (L.) Karst.) bark. Allelopathy J. 35, 129 - 138." type="journal article" year="2015">Latkowska et al., 2015</bibRefCitation>
|
||
). However, further experiments with extracted lichen substances are necessary to justify this hypothesis.
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |