267 lines
33 KiB
XML
267 lines
33 KiB
XML
<document id="91FA3B9435DCBCE96FF5060037F3704B" ID-DOI="10.1016/j.phytochem.2014.10.001" ID-ISSN="1873-3700" ID-Zenodo-Dep="10490544" IM.bibliography_approvedBy="felipe" IM.illustrations_approvedBy="carolina" IM.materialsCitations_approvedBy="felipe" IM.metadata_approvedBy="felipe" IM.tables_approvedBy="carolina" IM.taxonomicNames_approvedBy="carolina" IM.treatments_approvedBy="carolina" checkinTime="1704963521416" checkinUser="felipe" docAuthor="Prota, N., Mumm, R., Bouwmeester, H. J. & Jongsma, M. A." docDate="2014" docId="1A2A87A6FF99FFA34C55BCDCB5B866AA" docLanguage="en" docName="Phytochemistry.108.129-136.pdf" docOrigin="Phytochemistry 108" docSource="http://dx.doi.org/10.1016/j.phytochem.2014.10.001" docStyle="DocumentStyle:9E596C34F4E94307D29315B03ACE1007.6:Phytochemistry.2014-2019.journal_article" docStyleId="9E596C34F4E94307D29315B03ACE1007" docStyleName="Phytochemistry.2014-2019.journal_article" docStyleVersion="6" docTitle="Persicaria Mill." docType="treatment" docVersion="1" lastPageNumber="130" masterDocId="E613FFDEFF98FFA24C02B860B67D6169" masterDocTitle="Comparison of the chemical composition of three species of smartweed (genus Persicaria) with a focus on drimane sesquiterpenoids" masterLastPageNumber="136" masterPageNumber="129" pageNumber="130" updateTime="1706224304975" updateUser="carolina">
|
||
<mods:mods id="7B7D4CB155F181893935A1DB0EA63F70" xmlns:mods="http://www.loc.gov/mods/v3">
|
||
<mods:titleInfo id="F3093A6C16A3EAC3E63B4F6704D8D75E">
|
||
<mods:title id="4CE12C1C98A1DB7DCBE9FFF3C7B00463">Comparison of the chemical composition of three species of smartweed (genus Persicaria) with a focus on drimane sesquiterpenoids</mods:title>
|
||
</mods:titleInfo>
|
||
<mods:name id="E00323845FEBE48BEB038732F930FCD5" type="personal">
|
||
<mods:role id="1FE7F784EC12B38F963CE2CB9C65CA87">
|
||
<mods:roleTerm id="B1467D8D1EE32603A388171E28FED0B2">Author</mods:roleTerm>
|
||
</mods:role>
|
||
<mods:namePart id="BF3D56D536BB995CFF000B8CDD220E6E">Prota, N.</mods:namePart>
|
||
<mods:affiliation id="7B216C65A60D5D318676C17974AC1FBC">Plant Research International, PO Box 619, 6700 AP Wageningen, The Netherlands & Laboratory of Plant Physiology, Wageningen University, PO Box 658, 6700 AR Wageningen, The Netherlands</mods:affiliation>
|
||
</mods:name>
|
||
<mods:name id="D4C2A75806C218A72BFCA79B76126F87" type="personal">
|
||
<mods:role id="C3F5FCFBC57A28851CE3B94236AD451B">
|
||
<mods:roleTerm id="EF9D78ABE5E077A712068FB0911A57F4">Author</mods:roleTerm>
|
||
</mods:role>
|
||
<mods:namePart id="199B878F6E9317CDFD6589B309F35CF0">Mumm, R.</mods:namePart>
|
||
</mods:name>
|
||
<mods:name id="7A426C96A051ECE00054B40CC817902C" type="personal">
|
||
<mods:role id="214E6D5A19731134F4DB2B6657379739">
|
||
<mods:roleTerm id="8572FAC46BD93578DBF946D4A471375B">Author</mods:roleTerm>
|
||
</mods:role>
|
||
<mods:namePart id="A6FDD29F78D9233331E8F828061643F7">Bouwmeester, H. J.</mods:namePart>
|
||
</mods:name>
|
||
<mods:name id="8D2AD9681BDDB51A809F75956901D987" type="personal">
|
||
<mods:role id="711A361A49AB0C9888236E6BEF037191">
|
||
<mods:roleTerm id="9C8E0BB9CF958854FB71C2E563509C82">Author</mods:roleTerm>
|
||
</mods:role>
|
||
<mods:namePart id="DDDA06D54B0B03881FFFF556EB073684">Jongsma, M. A.</mods:namePart>
|
||
</mods:name>
|
||
<mods:typeOfResource id="75BAD75EC747327D9538512A411FBC8F">text</mods:typeOfResource>
|
||
<mods:relatedItem id="8EE49963AC098483285D12879E62FF55" type="host">
|
||
<mods:titleInfo id="A29721B64DA5D021E0B0AF8A274ED1DA">
|
||
<mods:title id="A87C1D797BDC32755EDEC26B5AEF79C3">Phytochemistry</mods:title>
|
||
</mods:titleInfo>
|
||
<mods:part id="9397F60BE230F6EB4209F9F8871397B1">
|
||
<mods:date id="691D74F2E9BB10C283E0E443B76CF641">2014</mods:date>
|
||
<mods:detail id="316D35A011B8AC18A4A95D69EE842E77" type="pubDate">
|
||
<mods:number id="1E880D356141A05B0F35EACBB88C58B0">2014-12-31</mods:number>
|
||
</mods:detail>
|
||
<mods:detail id="86B6B2ACA9F11A6D5413512C51751168" type="volume">
|
||
<mods:number id="BD481BFCD06DA8D3BA864280A8DDF165">108</mods:number>
|
||
</mods:detail>
|
||
<mods:extent id="669637323511F0B22D0C166587AC391C" unit="page">
|
||
<mods:start id="9FAAE081A42DB680B6781E92FC89D767">129</mods:start>
|
||
<mods:end id="354738C5EA9591AB9BF54EB0FD6823CB">136</mods:end>
|
||
</mods:extent>
|
||
</mods:part>
|
||
</mods:relatedItem>
|
||
<mods:location id="3126CA11488596939F749D74DDE69CFB">
|
||
<mods:url id="37A33A2582047E9E1D4FBAE3D339BC56">http://dx.doi.org/10.1016/j.phytochem.2014.10.001</mods:url>
|
||
</mods:location>
|
||
<mods:classification id="8B3FA4FE39475A45873076153FD97774">journal article</mods:classification>
|
||
<mods:identifier id="0E9B1BCA94D6A559357E72F4EA34591D" type="DOI">10.1016/j.phytochem.2014.10.001</mods:identifier>
|
||
<mods:identifier id="48DB2EFBF05CA9F3A7E49EB49311333A" type="ISSN">1873-3700</mods:identifier>
|
||
<mods:identifier id="43A2DC4C7C6C7AB514B7280A99704B87" type="Zenodo-Dep">10490544</mods:identifier>
|
||
</mods:mods>
|
||
<treatment id="1A2A87A6FF99FFA34C55BCDCB5B866AA" LSID="urn:lsid:plazi:treatment:1A2A87A6FF99FFA34C55BCDCB5B866AA" httpUri="http://treatment.plazi.org/id/1A2A87A6FF99FFA34C55BCDCB5B866AA" lastPageNumber="130" pageId="1" pageNumber="130">
|
||
<subSubSection id="DA99653BFF99FFA34C55BCDCB48B65B9" box="[87,758,1212,1232]" pageId="1" pageNumber="130" type="nomenclature">
|
||
<paragraph id="923C36B0FF99FFA34C55BCDCB48B65B9" blockId="1.[87,758,1212,1232]" box="[87,758,1212,1232]" pageId="1" pageNumber="130">
|
||
<heading id="C97481DCFF99FFA34C55BCDCB48B65B9" box="[87,758,1212,1232]" centered="true" fontSize="36" level="2" pageId="1" pageNumber="130" reason="3">
|
||
<emphasis id="A0F7EAA2FF99FFA34C55BCDCB48B65B9" box="[87,758,1212,1232]" italics="true" pageId="1" pageNumber="130">
|
||
2.1. Interspecific variation of the chemical composition of
|
||
<taxonomicName id="55834D33FF99FFA34E6DBCDCB4B665B9" ID-CoL="6LSN" authorityName="Mill." baseAuthorityName="(L.)" box="[623,715,1212,1232]" class="Magnoliopsida" family="Polygonaceae" genus="Persicaria" kingdom="Plantae" order="Caryophyllales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="genus">Persicaria</taxonomicName>
|
||
spp.
|
||
</emphasis>
|
||
</heading>
|
||
</paragraph>
|
||
</subSubSection>
|
||
<subSubSection id="DA99653BFF99FFA34C74BC94B5B866AA" pageId="1" pageNumber="130" type="description">
|
||
<paragraph id="923C36B0FF99FFA34C74BC94B2736222" blockId="1.[87,758,1267,1316]" lastBlockId="1.[805,1475,182,1987]" pageId="1" pageNumber="130">
|
||
Seeds of three species of the
|
||
<taxonomicName id="55834D33FF99FFA34DA4BC93B479646E" box="[422,516,1267,1287]" class="Magnoliopsida" family="Polygonaceae" genus="Persicaria" kingdom="Plantae" order="Caryophyllales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="genus">
|
||
<emphasis id="A0F7EAA2FF99FFA34DA4BC93B479646E" box="[422,516,1267,1287]" italics="true" pageId="1" pageNumber="130">Persicaria</emphasis>
|
||
</taxonomicName>
|
||
genus,
|
||
<taxonomicName id="55834D33FF99FFA34E56BC93B4AA646E" box="[596,727,1267,1287]" class="Magnoliopsida" family="Polygonaceae" genus="Persicaria" kingdom="Plantae" order="Caryophyllales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="species" species="hydropiper">
|
||
<emphasis id="A0F7EAA2FF99FFA34E56BC93B4AA646E" box="[596,727,1267,1287]" italics="true" pageId="1" pageNumber="130">P. hydropiper</emphasis>
|
||
</taxonomicName>
|
||
,
|
||
<taxonomicName id="55834D33FF99FFA34EE6BC93B6EC644A" baseAuthorityName="Eggelte" baseAuthorityYear="2007" class="Magnoliopsida" family="Polygonaceae" genus="Persicaria" kingdom="Plantae" order="Caryophyllales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="species" species="minor">
|
||
<emphasis id="A0F7EAA2FF99FFA34EE6BC93B6EC644A" italics="true" pageId="1" pageNumber="130">P. minor</emphasis>
|
||
</taxonomicName>
|
||
and
|
||
<taxonomicName id="55834D33FF99FFA34CC6BD6FB74A644A" box="[196,311,1295,1315]" class="Magnoliopsida" family="Polygonaceae" genus="Persicaria" kingdom="Plantae" order="Caryophyllales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="species" species="maculosa">
|
||
<emphasis id="A0F7EAA2FF99FFA34CC6BD6FB74A644A" box="[196,311,1295,1315]" italics="true" pageId="1" pageNumber="130">P. maculosa</emphasis>
|
||
</taxonomicName>
|
||
, were collected in the woods in close range of each other. The three species were identified by taxonomist Ronald van den Berg (Wageningen UR) (Supplementary
|
||
<figureCitation id="0AB82A35FF99FFA3497EB8B2B3BF618C" box="[1404,1474,210,229]" captionStart="Fig" captionStartId="5.[87,113,1049,1063]" captionTargetBox="[208,1344,181,1020]" captionTargetId="figure-560@5.[208,1344,181,1020]" captionTargetPageId="5" captionText="Fig. 3. Similarity matrix of the compounds, obtained using the Log2-transformed peak areas of the different P. hydropiper flower samples throughout development. The similarity of the abundance pattern between two given compounds assumes values between —1 and 1, with 1 meaning a 100% identical pattern. The cells at the diagonal are always intensely red as they represent the comparison of the abundance pattern of one compound with itself." figureDoi="http://doi.org/10.5281/zenodo.10490550" httpUri="https://zenodo.org/record/10490550/files/figure.png" pageId="1" pageNumber="130">Fig. S3</figureCitation>
|
||
for images of the plants). Seven separate samples were taken from plants raised from the seeds: three developmental stages of flowers and four of leaves. In
|
||
<figureCitation id="0AB82A35FF99FFA3489BB946B2AB6050" box="[1177,1238,294,313]" captionStart="Fig" captionStartId="1.[87,113,1924,1938]" captionTargetBox="[101,744,1401,1895]" captionTargetId="figure-1076@1.[101,744,1401,1895]" captionTargetPageId="1" captionText="Fig. 1. Light micrograph of a longitudinal cross section of a paraffin embedded flower of P. hydropiper. Arrows indicate the valvate glands (cavities) where polygodial is stored." figureDoi="http://doi.org/10.5281/zenodo.10490546" httpUri="https://zenodo.org/record/10490546/files/figure.png" pageId="1" pageNumber="130">Fig. 1</figureCitation>
|
||
, a cross section of a
|
||
<taxonomicName id="55834D33FF99FFA34F27B921B5D7603C" box="[805,938,321,341]" class="Magnoliopsida" family="Polygonaceae" genus="Persicaria" kingdom="Plantae" order="Caryophyllales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="species" species="hydropiper">
|
||
<emphasis id="A0F7EAA2FF99FFA34F27B921B5D7603C" box="[805,938,321,341]" italics="true" pageId="1" pageNumber="130">P. hydropiper</emphasis>
|
||
</taxonomicName>
|
||
flower clearly shows the presence of the valvate glands in the tepals of the flowers. Samples were extracted in dichloromethane (DCM) and analysed by coupled gas chromatography–mass spectrometry (GC–MS). A total of 29 major metabolites could be identified across all three species, 15 of which were present in all. Nearly all (27/29) identified metabolites were terpenoids, most were sesquiterpenoids (21/29) and a quarter of those were drimanes (5/21) (
|
||
<tableCitation id="DF01030BFF99FFA34854BA65B2D16371" box="[1110,1196,517,536]" captionStart="Table 1" captionStartId="2.[114,158,183,197]" captionTargetPageId="2" captionText="Table 1 Chemical composition of organic extracts of flowers a of three Persicaria species." pageId="1" pageNumber="130">Tables 1</tableCitation>
|
||
and
|
||
<tableCitation id="DF01030BFF99FFA348E1BA65B28D6371" box="[1251,1264,517,536]" captionStart="Table 2" captionStartId="3.[87,131,183,197]" captionTargetPageId="3" captionText="Table 2 Chemical composition of organic extracts of leaves a of three Persicaria species." pageId="1" pageNumber="130">2</tableCitation>
|
||
, structures in
|
||
<figureCitation id="0AB82A35FF99FFA34988BA65B3C06371" box="[1418,1469,517,536]" captionStart="Fig" captionStartId="3.[87,113,1780,1794]" captionTargetBox="[140,1420,1466,1752]" captionTargetId="figure-465@3.[140,1420,1466,1752]" captionTargetPageId="3" captionText="Fig. 2. Structures of the five drimane sesquiterpenoids observed in the extracts of the analysed plants: (1) drimenol; (2) polygodial; (3) 9-epi-polygodial; (4) drimenin; (5) isodrimenin." figureDoi="http://doi.org/10.5281/zenodo.10490548" httpUri="https://zenodo.org/record/10490548/files/figure.png" pageId="1" pageNumber="130">Fig 2</figureCitation>
|
||
, and mass spectra in
|
||
<figureCitation id="0AB82A35FF99FFA34FFCBA41B23C635D" box="[1022,1089,545,564]" captionStart="Fig" captionStartId="1.[87,113,1924,1938]" captionTargetBox="[101,744,1401,1895]" captionTargetId="figure-1076@1.[101,744,1401,1895]" captionTargetPageId="1" captionText="Fig. 1. Light micrograph of a longitudinal cross section of a paraffin embedded flower of P. hydropiper. Arrows indicate the valvate glands (cavities) where polygodial is stored." figureDoi="http://doi.org/10.5281/zenodo.10490546" httpUri="https://zenodo.org/record/10490546/files/figure.png" pageId="1" pageNumber="130">Fig. S1</figureCitation>
|
||
).
|
||
<tableCitation id="DF01030BFF99FFA3485ABA41B2D9635D" box="[1112,1188,545,564]" captionStart="Table 1" captionStartId="2.[114,158,183,197]" captionTargetPageId="2" captionText="Table 1 Chemical composition of organic extracts of flowers a of three Persicaria species." pageId="1" pageNumber="130">Table 1</tableCitation>
|
||
shows the average relative abundance of the 29 metabolites in the flowers of the three species, while in
|
||
<tableCitation id="DF01030BFF99FFA34FADBA39B5846305" box="[943,1017,601,620]" captionStart="Table 2" captionStartId="3.[87,131,183,197]" captionTargetPageId="3" captionText="Table 2 Chemical composition of organic extracts of leaves a of three Persicaria species." pageId="1" pageNumber="130">Table 2</tableCitation>
|
||
the chemical profiles of the leaves are listed.
|
||
<taxonomicName id="55834D33FF99FFA34F27BA13B5DA63EE" box="[805,935,627,647]" class="Magnoliopsida" family="Polygonaceae" genus="Persicaria" kingdom="Plantae" order="Caryophyllales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="species" species="hydropiper">
|
||
<emphasis id="A0F7EAA2FF99FFA34F27BA13B5DA63EE" box="[805,935,627,647]" italics="true" pageId="1" pageNumber="130">P. hydropiper</emphasis>
|
||
</taxonomicName>
|
||
was the species with the widest variety of metabolites detected in our analyses; the only compound present in the other two species, but not in water-pepper, was b- selinene. In general, flower samples contained more different and higher quantities of metabolites compared to leaves, with the exception of the three neophytadiene isomers, which were more abundant in the leaves, because they are degradation products of chlorophyll (
|
||
<bibRefCitation id="F6124B41FF99FFA34F6ABB58B27C6222" author="Rowland, R. L." box="[872,1025,824,843]" pageId="1" pageNumber="130" pagination="5007 - 5010" refId="ref8171" refString="Rowland, R. L., 1957. Flue-cured Tobacco. II. Neophytadiene. J. Am. Chem. Soc. 79, 5007 - 5010." type="journal article" year="1957">Rowland, 1957</bibRefCitation>
|
||
).
|
||
</paragraph>
|
||
<paragraph id="923C36B0FF99FFA34F46BB34B5E96584" blockId="1.[805,1475,182,1987]" pageId="1" pageNumber="130">
|
||
The five sesquiterpene drimanes observed in the gas chromatogram were drimenol, polygodial, 9-
|
||
<emphasis id="A0F7EAA2FF99FFA3489ABB0FB2C862EA" box="[1176,1205,879,899]" italics="true" pageId="1" pageNumber="130">epi</emphasis>
|
||
-polygodial, drimenin and isodrimenin (
|
||
<figureCitation id="0AB82A35FF99FFA34FB2BBEBB59862F6" box="[944,997,907,927]" captionStart="Fig" captionStartId="3.[87,113,1780,1794]" captionTargetBox="[140,1420,1466,1752]" captionTargetId="figure-465@3.[140,1420,1466,1752]" captionTargetPageId="3" captionText="Fig. 2. Structures of the five drimane sesquiterpenoids observed in the extracts of the analysed plants: (1) drimenol; (2) polygodial; (3) 9-epi-polygodial; (4) drimenin; (5) isodrimenin." figureDoi="http://doi.org/10.5281/zenodo.10490548" httpUri="https://zenodo.org/record/10490548/files/figure.png" pageId="1" pageNumber="130">Fig 2</figureCitation>
|
||
). It is known that 9-
|
||
<emphasis id="A0F7EAA2FF99FFA348C4BBEAB29E62F7" box="[1222,1251,906,926]" italics="true" pageId="1" pageNumber="130">epi</emphasis>
|
||
-polygodial is formed from polygodial by base-treatment (
|
||
<bibRefCitation id="F6124B41FF99FFA3489ABBC8B32B62D2" author="Cortes, M. & Moreno, L. & Lopez, J." box="[1176,1366,935,955]" pageId="1" pageNumber="130" pagination="36 - 37" refId="ref7278" refString="Cortes, M., Moreno, L., Lopez, J., 1998. Partial synthesis of (-) - 11, 12 - dinordriman- 8 - one and the (-) - enantiomer of polywood. J. Chem. Res. Synop., 36 - 37." type="book chapter" year="1998">Cortés et al., 1998</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="F6124B41FF99FFA34963BBC7B5CD62BF" author="Kubo, I. & Ganjian, I." pageId="1" pageNumber="130" pagination="1063 - 1064" refId="ref7759" refString="Kubo, I., Ganjian, I., 1981. Insect antifeedant terpenes, hot-tasting to humans. Cell. Mol. Life Sci. 37, 1063 - 1064." type="journal article" year="1981">Kubo and Ganjian, 1981</bibRefCitation>
|
||
), and there are other reports of this compound being an artifact of the GC–MS analysis (
|
||
<bibRefCitation id="F6124B41FF99FFA34885BBBFB32A629B" author="Asakawa, Y. & Toyota, M. & Oiso, Y. & Braggins, J. E." box="[1159,1367,991,1011]" pageId="1" pageNumber="130" pagination="1380 - 1381" refId="ref7065" refString="Asakawa, Y., Toyota, M., Oiso, Y., Braggins, J. E., 2001. Occurrence of polygodial and 1 - (2,4,6 - trimethoxyphenyl) - but- 2 - en- 1 - one from some ferns and liverworts: role of pungent components in bryophytes and pteridophytes evolution. Chem. Pharm. Bull. 49, 1380 - 1381." type="journal article" year="2001">Asakawa et al., 2001</bibRefCitation>
|
||
). We confirmed that upon injection of a
|
||
<superScript id="65F69BF8FF99FFA3485FBB97B21B656A" attach="right" box="[1117,1126,1015,1027]" fontSize="5" pageId="1" pageNumber="130">1</superScript>
|
||
H NMR verified reference standard of pure polygodial, also 9-
|
||
<emphasis id="A0F7EAA2FF99FFA3482DBC76B2316543" box="[1071,1100,1046,1066]" italics="true" pageId="1" pageNumber="130">epi</emphasis>
|
||
-polygodial is observed, and that the ratio of the peaks versus 9-
|
||
<emphasis id="A0F7EAA2FF99FFA34859BC52B205652F" box="[1115,1144,1074,1094]" italics="true" pageId="1" pageNumber="130">epi</emphasis>
|
||
-polygodial varied from 1.6 to 0.8:1 depending on the injection temperature (
|
||
<figureCitation id="0AB82A35FF99FFA34905BC2FB334650B" box="[1287,1353,1103,1122]" captionStart="Fig" captionStartId="3.[87,113,1780,1794]" captionTargetBox="[140,1420,1466,1752]" captionTargetId="figure-465@3.[140,1420,1466,1752]" captionTargetPageId="3" captionText="Fig. 2. Structures of the five drimane sesquiterpenoids observed in the extracts of the analysed plants: (1) drimenol; (2) polygodial; (3) 9-epi-polygodial; (4) drimenin; (5) isodrimenin." figureDoi="http://doi.org/10.5281/zenodo.10490548" httpUri="https://zenodo.org/record/10490548/files/figure.png" pageId="1" pageNumber="130">Fig. S2</figureCitation>
|
||
). An earlier study, however, reports the
|
||
<superScript id="65F69BF8FF99FFA34848BC07B22E651A" attach="right" box="[1098,1107,1127,1139]" fontSize="5" pageId="1" pageNumber="130">1</superScript>
|
||
H NMR spectra for both epimers in
|
||
<taxonomicName id="55834D33FF99FFA34F27BCE6B2BF65F3" authority="(Rodriguez et al., 2005)" baseAuthorityName="Rodriguez" baseAuthorityYear="2005" box="[805,1218,1158,1178]" class="Magnoliopsida" family="Winteraceae" genus="Drymis" higherTaxonomySource="GBIF" kingdom="Plantae" order="Canellales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="species" species="winterii">
|
||
<emphasis id="A0F7EAA2FF99FFA34F27BCE6B5C265F3" box="[805,959,1158,1178]" italics="true" pageId="1" pageNumber="130">Drymis winterii</emphasis>
|
||
(
|
||
<bibRefCitation id="F6124B41FF99FFA34FD0BCE7B2C465F0" author="Rodriguez, B. & Zapata, N. & Medina, P. & Vinuela, E." box="[978,1209,1158,1178]" pageId="1" pageNumber="130" pagination="82 - 84" refId="ref8118" refString="Rodriguez, B., Zapata, N., Medina, P., Vinuela, E., 2005. A complete 1 H and 13 C NMR data assignment for four drimane sesquiterpenoids isolated from Drimys winterii. Magn. Reson. Chem. 43, 82 - 84." type="journal article" year="2005">Rodríguez et al., 2005</bibRefCitation>
|
||
)
|
||
</taxonomicName>
|
||
. As our GC–MS method does not allow the reliable estimation of the ratios, we report the combined concentrations of both epimers under the label of polygodial.
|
||
</paragraph>
|
||
<paragraph id="923C36B0FF99FFA34F46BC96B379678D" blockId="1.[805,1475,182,1987]" pageId="1" pageNumber="130">
|
||
Polygodial was the most abundant compound in
|
||
<taxonomicName id="55834D33FF99FFA34942BC95B3BF6460" box="[1344,1474,1269,1289]" class="Magnoliopsida" family="Polygonaceae" genus="Persicaria" kingdom="Plantae" order="Caryophyllales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="species" species="hydropiper">
|
||
<emphasis id="A0F7EAA2FF99FFA34942BC95B3BF6460" box="[1344,1474,1269,1289]" italics="true" pageId="1" pageNumber="130">P. hydropiper</emphasis>
|
||
</taxonomicName>
|
||
flowers, making up for 77% of the extract, equivalent to
|
||
<quantity id="557B9B55FF99FFA34F27BD4EB5156428" box="[805,872,1326,1345]" metricMagnitude="-6" metricUnit="kg" metricValue="6.2" pageId="1" pageNumber="130" unit="mg" value="6.2">6.2 mg</quantity>
|
||
g FW
|
||
<superScript id="65F69BF8FF99FFA34FA3BD49B5CB645F" attach="left" box="[929,950,1321,1334]" fontSize="5" pageId="1" pageNumber="130">
|
||
<emphasis id="A0F7EAA2FF99FFA34FA3BD49B5D0645F" box="[929,941,1321,1334]" italics="true" pageId="1" pageNumber="130">—</emphasis>
|
||
1
|
||
</superScript>
|
||
(
|
||
<tableCitation id="DF01030BFF99FFA34FCABD4EB2636428" box="[968,1054,1326,1345]" captionStart="Table 1" captionStartId="2.[114,158,183,197]" captionTargetPageId="2" captionText="Table 1 Chemical composition of organic extracts of flowers a of three Persicaria species." pageId="1" pageNumber="130">Tables 1</tableCitation>
|
||
and
|
||
<tableCitation id="DF01030BFF99FFA34854BD4EB21E6428" box="[1110,1123,1326,1345]" captionStart="Table 3" captionStartId="4.[114,158,183,197]" captionTargetPageId="4" captionText="Table 3 Species-specific content of polygodial a in different tissues." pageId="1" pageNumber="130">3</tableCitation>
|
||
). It was 200 times less abundant in
|
||
<taxonomicName id="55834D33FF99FFA34F46BD29B5E76434" baseAuthorityName="Eggelte" baseAuthorityYear="2007" box="[836,922,1353,1373]" class="Magnoliopsida" family="Polygonaceae" genus="Persicaria" kingdom="Plantae" order="Caryophyllales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="species" species="minor">
|
||
<emphasis id="A0F7EAA2FF99FFA34F46BD29B5E76434" box="[836,922,1353,1373]" italics="true" pageId="1" pageNumber="130">P. minor</emphasis>
|
||
</taxonomicName>
|
||
flowers (
|
||
<quantity id="557B9B55FF99FFA34803BD2AB2226434" box="[1025,1119,1354,1373]" metricMagnitude="-8" metricUnit="kg" metricValue="3.2" pageId="1" pageNumber="130" unit="mg" value="0.032">0.032 mg</quantity>
|
||
g FW
|
||
<superScript id="65F69BF8FF99FFA3489ABD25B2D0643B" attach="left" box="[1176,1197,1349,1362]" fontSize="5" pageId="1" pageNumber="130">
|
||
<emphasis id="A0F7EAA2FF99FFA3489ABD25B2D9643B" box="[1176,1188,1349,1362]" italics="true" pageId="1" pageNumber="130">—</emphasis>
|
||
1
|
||
</superScript>
|
||
), representing 25% of the total compounds, and 100,000 times less abundant in
|
||
<taxonomicName id="55834D33FF99FFA3494DBD05B3BF6410" box="[1359,1474,1381,1401]" class="Magnoliopsida" family="Polygonaceae" genus="Persicaria" kingdom="Plantae" order="Caryophyllales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="species" species="maculosa">
|
||
<emphasis id="A0F7EAA2FF99FFA3494DBD05B3BF6410" box="[1359,1474,1381,1401]" italics="true" pageId="1" pageNumber="130">P. maculosa</emphasis>
|
||
</taxonomicName>
|
||
flowers (
|
||
<quantity id="557B9B55FF99FFA34F86BDE2B5C064FC" box="[900,957,1410,1429]" metricMagnitude="-11" metricUnit="kg" metricValue="7.0" pageId="1" pageNumber="130" unit="ng" value="70.0">70 ng</quantity>
|
||
g FW
|
||
<superScript id="65F69BF8FF99FFA34FF7BD1DB27764E3" attach="left" box="[1013,1034,1405,1418]" fontSize="5" pageId="1" pageNumber="130">
|
||
<emphasis id="A0F7EAA2FF99FFA34FF7BD1DB27C64E3" box="[1013,1025,1405,1418]" italics="true" pageId="1" pageNumber="130">—</emphasis>
|
||
1
|
||
</superScript>
|
||
), representing 0.1% of total compounds (
|
||
<tableCitation id="DF01030BFF99FFA34F2FBDFEB5F964D8" box="[813,900,1438,1457]" captionStart="Table 1" captionStartId="2.[114,158,183,197]" captionTargetPageId="2" captionText="Table 1 Chemical composition of organic extracts of flowers a of three Persicaria species." pageId="1" pageNumber="130">Tables 1</tableCitation>
|
||
and
|
||
<tableCitation id="DF01030BFF99FFA34FBCBDFEB5B664D8" box="[958,971,1438,1457]" captionStart="Table 3" captionStartId="4.[114,158,183,197]" captionTargetPageId="4" captionText="Table 3 Species-specific content of polygodial a in different tissues." pageId="1" pageNumber="130">3</tableCitation>
|
||
). The drimane sesquiterpene lactones drimenin and isodrimenin were minor compounds when compared to polygodial, accounting for only 2% of the
|
||
<taxonomicName id="55834D33FF99FFA348A3BDB4B3596481" box="[1185,1316,1492,1512]" class="Magnoliopsida" family="Polygonaceae" genus="Persicaria" kingdom="Plantae" order="Caryophyllales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="species" species="hydropiper">
|
||
<emphasis id="A0F7EAA2FF99FFA348A3BDB4B3596481" box="[1185,1316,1492,1512]" italics="true" pageId="1" pageNumber="130">P. hydropiper</emphasis>
|
||
</taxonomicName>
|
||
flower extract. Relative to
|
||
<taxonomicName id="55834D33FF99FFA34F97BD90B269676D" box="[917,1044,1520,1540]" class="Magnoliopsida" family="Polygonaceae" genus="Persicaria" kingdom="Plantae" order="Caryophyllales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="species" species="hydropiper">
|
||
<emphasis id="A0F7EAA2FF99FFA34F97BD90B269676D" box="[917,1044,1520,1540]" italics="true" pageId="1" pageNumber="130">P. hydropiper</emphasis>
|
||
</taxonomicName>
|
||
, they were 10- and 100-fold less abundant in
|
||
<taxonomicName id="55834D33FF99FFA34F43BE6CB5E96749" baseAuthorityName="Eggelte" baseAuthorityYear="2007" box="[833,916,1548,1568]" class="Magnoliopsida" family="Polygonaceae" genus="Persicaria" kingdom="Plantae" order="Caryophyllales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="species" species="minor">
|
||
<emphasis id="A0F7EAA2FF99FFA34F43BE6CB5E96749" box="[833,916,1548,1568]" italics="true" pageId="1" pageNumber="130">P. minor</emphasis>
|
||
</taxonomicName>
|
||
flowers, respectively, and not detected in
|
||
<taxonomicName id="55834D33FF99FFA3494CBE6CB3BF6749" box="[1358,1474,1548,1568]" class="Magnoliopsida" family="Polygonaceae" genus="Persicaria" kingdom="Plantae" order="Caryophyllales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="species" species="maculosa">
|
||
<emphasis id="A0F7EAA2FF99FFA3494CBE6CB3BF6749" box="[1358,1474,1548,1568]" italics="true" pageId="1" pageNumber="130">P. maculosa</emphasis>
|
||
</taxonomicName>
|
||
flowers. Drimenol, the putative precursor of polygodial (
|
||
<bibRefCitation id="F6124B41FF99FFA3497ABE49B5256731" author="Pickett, J. A." pageId="1" pageNumber="130" pagination="235 - 239" refId="ref7982" refString="Pickett, J. A., 1985. Production of behaviour-controlling chemicals by crop plants. Philos. Trans. R. Soc. Lond. B, Biol. Sci. 310, 235 - 239." type="journal article" year="1985">Pickett, 1985</bibRefCitation>
|
||
) was only detected at low concentrations in
|
||
<taxonomicName id="55834D33FF99FFA3493CBE24B3BF6731" box="[1342,1474,1604,1624]" class="Magnoliopsida" family="Polygonaceae" genus="Persicaria" kingdom="Plantae" order="Caryophyllales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="species" species="hydropiper">
|
||
<emphasis id="A0F7EAA2FF99FFA3493CBE24B3BF6731" box="[1342,1474,1604,1624]" italics="true" pageId="1" pageNumber="130">P. hydropiper</emphasis>
|
||
</taxonomicName>
|
||
and not in the other species, presumably because it serves as an intermediate and it is promptly converted. Comparing leaves to flowers, polygodial was 10
|
||
<emphasis id="A0F7EAA2FF99FFA34832BEF8B23C67C5" box="[1072,1089,1688,1708]" italics="true" pageId="1" pageNumber="130">×</emphasis>
|
||
more abundant in flowers of
|
||
<taxonomicName id="55834D33FF99FFA34969BEF8B52B67AE" class="Magnoliopsida" family="Polygonaceae" genus="Persicaria" kingdom="Plantae" order="Caryophyllales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="species" species="hydropiper">
|
||
<emphasis id="A0F7EAA2FF99FFA34969BEF8B52B67AE" italics="true" pageId="1" pageNumber="130">P. hydropiper</emphasis>
|
||
</taxonomicName>
|
||
, equally abundant in
|
||
<taxonomicName id="55834D33FF99FFA3482CBED3B20267AE" baseAuthorityName="Eggelte" baseAuthorityYear="2007" box="[1070,1151,1715,1735]" class="Magnoliopsida" family="Polygonaceae" genus="Persicaria" kingdom="Plantae" order="Caryophyllales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="species" species="minor">
|
||
<emphasis id="A0F7EAA2FF99FFA3482CBED3B20267AE" box="[1070,1151,1715,1735]" italics="true" pageId="1" pageNumber="130">P. minor</emphasis>
|
||
</taxonomicName>
|
||
leaves and flowers and 10
|
||
<emphasis id="A0F7EAA2FF99FFA34984BED3B3EA67AE" box="[1414,1431,1715,1735]" italics="true" pageId="1" pageNumber="130">×</emphasis>
|
||
less abundant in flowers than leaves of
|
||
<taxonomicName id="55834D33FF99FFA3488EBEAFB282678A" box="[1164,1279,1743,1763]" class="Magnoliopsida" family="Polygonaceae" genus="Persicaria" kingdom="Plantae" order="Caryophyllales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="species" species="maculosa">
|
||
<emphasis id="A0F7EAA2FF99FFA3488EBEAFB282678A" box="[1164,1279,1743,1763]" italics="true" pageId="1" pageNumber="130">P. maculosa</emphasis>
|
||
</taxonomicName>
|
||
.
|
||
</paragraph>
|
||
<paragraph id="923C36B0FF99FFA34F46BE8CB5B866AA" blockId="1.[805,1475,182,1987]" pageId="1" pageNumber="130">
|
||
The low levels of polygodial in
|
||
<taxonomicName id="55834D33FF99FFA3489ABE8BB3736796" box="[1176,1294,1771,1791]" class="Magnoliopsida" family="Polygonaceae" genus="Persicaria" kingdom="Plantae" order="Caryophyllales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="species" species="maculosa">
|
||
<emphasis id="A0F7EAA2FF99FFA3489ABE8BB3736796" box="[1176,1294,1771,1791]" italics="true" pageId="1" pageNumber="130">P. maculosa</emphasis>
|
||
</taxonomicName>
|
||
were earlier not found by
|
||
<bibRefCitation id="F6124B41FF99FFA34F85BF68B2FA6672" author="Hagendoorn, M. J. M. & Geelen, T. A. M. & Vanbeek, T. A. & Jamar, D. C. L. & Tetteroo, F. A. A. & Vanderplas, L. H. W." box="[903,1159,1800,1820]" pageId="1" pageNumber="130" pagination="595 - 600" refId="ref7644" refString="Hagendoorn, M. J. M., Geelen, T. A. M., Vanbeek, T. A., Jamar, D. C. L., Tetteroo, F. A. A., Vanderplas, L. H. W., 1994. Occurrence of polygodial in plant organs and tissueculture of Polygonum hydropiper. Physiol. Plant. 92, 595 - 600." type="journal article" year="1994">Hagendoorn et al. (1994)</bibRefCitation>
|
||
for specimens collected in
|
||
<collectingCountry id="EA947620FF99FFA349A3BF68B5DC665E" name="Netherlands" pageId="1" pageNumber="130">the Netherlands</collectingCountry>
|
||
, but they are in line with the results of
|
||
<bibRefCitation id="F6124B41FF99FFA3494ABF44B51A663A" author="Derita, M. G. & Gattuso, S. J. & Zacchino, S. A." pageId="1" pageNumber="130" pagination="55 - 58" refId="ref7439" refString="Derita, M. G., Gattuso, S. J., Zacchino, S. A., 2008. Occurrence of polygodial in species of Polygonum genus belonging to Persicaria section. Biochem. Syst. Ecol. 36, 55 - 58." type="journal article" year="2008">Derita et al. (2008)</bibRefCitation>
|
||
who detected low amounts of polygodial (
|
||
<quantity id="557B9B55FF99FFA34914BF20B315663A" box="[1302,1384,1856,1875]" metricMagnitude="-7" metricUnit="kg" metricValue="5.4" pageId="1" pageNumber="130" unit="mg" value="0.54">0.54 mg</quantity>
|
||
g DW
|
||
<superScript id="65F69BF8FF99FFA349A7BF5BB3C76621" attach="right" box="[1445,1466,1851,1864]" fontSize="5" pageId="1" pageNumber="130">
|
||
<emphasis id="A0F7EAA2FF99FFA349A7BF5BB3CC6621" box="[1445,1457,1851,1864]" italics="true" pageId="1" pageNumber="130">—</emphasis>
|
||
1
|
||
</superScript>
|
||
) in leaves of
|
||
<taxonomicName id="55834D33FF99FFA34FA6BF3BB2646606" box="[932,1049,1883,1903]" class="Magnoliopsida" family="Polygonaceae" genus="Persicaria" kingdom="Plantae" order="Caryophyllales" pageId="1" pageNumber="130" phylum="Tracheophyta" rank="species" species="maculosa">
|
||
<emphasis id="A0F7EAA2FF99FFA34FA6BF3BB2646606" box="[932,1049,1883,1903]" italics="true" pageId="1" pageNumber="130">P. maculosa</emphasis>
|
||
</taxonomicName>
|
||
from
|
||
<collectingCountry id="EA947620FF99FFA34859BF3CB2BD6606" box="[1115,1216,1884,1903]" name="Argentina" pageId="1" pageNumber="130">Argentina</collectingCountry>
|
||
. Yet, by comparison, our specimen contains only
|
||
<quantity id="557B9B55FF99FFA34829BF18B21F66E2" box="[1067,1122,1912,1931]" metricMagnitude="-11" metricUnit="kg" metricValue="7.0" pageId="1" pageNumber="130" unit="ng" value="70.0">70 ng</quantity>
|
||
g FW
|
||
<superScript id="65F69BF8FF99FFA34898BF13B2CD66E9" attach="left" box="[1178,1200,1907,1920]" fontSize="5" pageId="1" pageNumber="130">
|
||
<emphasis id="A0F7EAA2FF99FFA34898BF13B2DB66E9" box="[1178,1190,1907,1920]" italics="true" pageId="1" pageNumber="130">—</emphasis>
|
||
1
|
||
</superScript>
|
||
. Taking into account the FW/DW comparison, this is still 100 times less than accessions from
|
||
<collectingCountry id="EA947620FF99FFA34F5EBFD0B5BC66AA" box="[860,961,1968,1987]" name="Argentina" pageId="1" pageNumber="130">Argentina</collectingCountry>
|
||
.
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |