183 lines
20 KiB
XML
183 lines
20 KiB
XML
<document id="ED40334D8A5E436137C32A5D0F8E46E0" ID-DOI="10.1016/j.phytochem.2021.112796" ID-ISSN="1873-3700" ID-Zenodo-Dep="8259205" IM.bibliography_approvedBy="felipe" IM.illustrations_approvedBy="jonas" IM.materialsCitations_approvedBy="felipe" IM.metadata_approvedBy="jonas" IM.tables_approvedBy="jonas" IM.taxonomicNames_approvedBy="jonas" IM.treatments_approvedBy="jonas" checkinTime="1692308221054" checkinUser="felipe" docAuthor="Nishidono, Yuto, Niwa, Kotaro, Kitajima, Aoi, Watanabe, Shiro, Tezuka, Yasuhiro, Arita, Masanori, Takabayashi, Junji & Tanaka, Ken" docDate="2021" docId="03BA87A2FF83FFAAFE39F8817994FADC" docLanguage="en" docName="Phytochemistry.188.112796.pdf" docOrigin="Phytochemistry (112796) 188" docSource="http://dx.doi.org/10.1016/j.phytochem.2021.112796" docStyle="DocumentStyle:F36D69FC8B198FBE91029DF9C24697D3.5:Phytochemistry.2020-.journal_article" docStyleId="F36D69FC8B198FBE91029DF9C24697D3" docStyleName="Phytochemistry.2020-.journal_article" docStyleVersion="5" docTitle="Saposhnikovia divaricata Schischk" docType="treatment" docVersion="1" lastPageNumber="4" masterDocId="FF83FFDAFF81FFA9FD0BFFD67836FF82" masterDocTitle="α-Linolenic acid in Papilio machaon larvae regurgitant induces a defensive response in Apiaceae" masterLastPageNumber="7" masterPageNumber="1" pageNumber="3" updateTime="1692620131718" updateUser="jonas">
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<mods:title id="8E5442277D36D9DB586D6E7AA7B129E4">α-Linolenic acid in Papilio machaon larvae regurgitant induces a defensive response in Apiaceae</mods:title>
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<mods:namePart id="80595B3C0121467F8B71343D300EA227">Nishidono, Yuto</mods:namePart>
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<mods:affiliation id="6DADA7C440EA947D7800E41AA6269261">College of Pharmaceutical Sciences, Ritsumeikan University, 1 - 1 - 1 Noji-Higashi, Kusatsu, Shiga, 525 - 8577, Japan</mods:affiliation>
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<mods:namePart id="EF1C338341D98C13310E694E1C19D542">Niwa, Kotaro</mods:namePart>
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<mods:affiliation id="A8C85A151512ED85786902A3DE3D1BFB">College of Pharmaceutical Sciences, Ritsumeikan University, 1 - 1 - 1 Noji-Higashi, Kusatsu, Shiga, 525 - 8577, Japan</mods:affiliation>
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<mods:nameIdentifier id="BC49757276DABAFB109FAA6CC8BAE8CE" type="email">ph0106hv@ed.ritsumei.ac.jp</mods:nameIdentifier>
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<mods:namePart id="A67EDA8172B846BB83F1F0A2D97D2BBE">Kitajima, Aoi</mods:namePart>
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<mods:affiliation id="099FC19AA2BD66B0599E06F83051B0F9">College of Pharmaceutical Sciences, Ritsumeikan University, 1 - 1 - 1 Noji-Higashi, Kusatsu, Shiga, 525 - 8577, Japan</mods:affiliation>
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<mods:nameIdentifier id="5AC7CF8692126D290CA7638A299DFAA7" type="email">ph0103xx@ed.ritsumei.ac.jp</mods:nameIdentifier>
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<mods:namePart id="5E061C73AB789AA3E47D27FEFD87FAAB">Watanabe, Shiro</mods:namePart>
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<mods:affiliation id="F9B581403089F2FC5F5D7A3F58F36A15">Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama, 930 - 0194, Japan</mods:affiliation>
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<mods:nameIdentifier id="300909D43200C7CF85A1FF58D3FFD8C3" type="email">shirowat@inm. u-toyama.ac.jp</mods:nameIdentifier>
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<mods:namePart id="E1589BED72073DDDAC283E3C8E2ADCD5">Tezuka, Yasuhiro</mods:namePart>
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<mods:affiliation id="F3B092955F9FB01A5AE95E991D8385EC">Faculty of Pharmaceutical Sciences, Hokuriku University, Ho- 3 Kanagawa-machi, Kanazawa, Ishikawa, 920 - 1181, Japan</mods:affiliation>
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<mods:nameIdentifier id="96D6E0AEEA0CE6096D9E1C86ECB53D6F" type="email">y-tezuka@hokuriku-u.ac.jp</mods:nameIdentifier>
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<mods:namePart id="DA26CB9929293DD4031CC6D6E7C7A41C">Arita, Masanori</mods:namePart>
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<mods:affiliation id="9450E116F7D47B2272192F1A30CC1F7B">National Institute of Genetics, 1111 Yata, Mishima, Shizuoka, 411 - 8540, Japan & RIKEN Center for Sustainable Resource Science, 1 - 7 - 22 Suehiro, Tsurumi, Yokohama, Kanagawa, 230 - 0045, Japan &</mods:affiliation>
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<mods:nameIdentifier id="CC87A64D32728A44C39D4DF9DDE4DDD7" type="email">arita@nig.ac.jp</mods:nameIdentifier>
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<mods:namePart id="3592E9842322327D23785444033D5FC9">Takabayashi, Junji</mods:namePart>
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<mods:affiliation id="CF4E058E54457579E47E6D1BBC63240F">Center for Ecological Research, Kyoto University, 2 - 509 - 3 Hirano, Otsu, Shiga, 520 - 2113, Japan</mods:affiliation>
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<mods:nameIdentifier id="203371FB379B2EAEF15ECAC8F878654E" type="email">junji@ecology.kyoto-u.ac.jp</mods:nameIdentifier>
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<mods:namePart id="C7E4630233611E2CDD3BF02EA734A6D0">Tanaka, Ken</mods:namePart>
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<mods:affiliation id="4B256883AB7C98ED01B571D279D297A2">College of Pharmaceutical Sciences, Ritsumeikan University, 1 - 1 - 1 Noji-Higashi, Kusatsu, Shiga, 525 - 8577, Japan</mods:affiliation>
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<mods:nameIdentifier id="C13604D2F1735744DAD8190859E09995" type="email">ktanaka@fc.ritsumei.ac.jp</mods:nameIdentifier>
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<mods:title id="11AF4827DA36792B6DD188764FB59509">Phytochemistry</mods:title>
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<mods:date id="D01FCB125DC964AA724D8A71A110D708">2021</mods:date>
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<mods:title id="F65DE856D4E204A43EB27D5191A529D3">112796</mods:title>
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<mods:number id="4957B5D4658427FEFE44A810D7002A5C">2021-08-31</mods:number>
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<mods:number id="9503A108F8AC66A3E40CA1D63DC153CC">188</mods:number>
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<mods:url id="B1A79F4707C8D6276749F210A15F9542">http://dx.doi.org/10.1016/j.phytochem.2021.112796</mods:url>
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<mods:classification id="FE2F4289CDD4AD50ACCEB86B6501D8EA">journal article</mods:classification>
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<mods:identifier id="A8AB95C39AA182E55974711518531100" type="DOI">10.1016/j.phytochem.2021.112796</mods:identifier>
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<mods:identifier id="CFDD088CD1D775154E54327327AFCD91" type="ISSN">1873-3700</mods:identifier>
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<treatment id="03BA87A2FF83FFAAFE39F8817994FADC" LSID="urn:lsid:plazi:treatment:03BA87A2FF83FFAAFE39F8817994FADC" httpUri="http://treatment.plazi.org/id/03BA87A2FF83FFAAFE39F8817994FADC" lastPageId="3" lastPageNumber="4" pageId="2" pageNumber="3">
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<subSubSection id="C309653FFF83FFABFE39F8817C13F807" pageId="2" pageNumber="3" type="nomenclature">
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<paragraph id="8BAC36B4FF83FFABFE39F8817C13F807" blockId="2.[818,1416,1878,1926]" pageId="2" pageNumber="3">
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<heading id="D0E481D8FF83FFABFE39F8817C13F807" fontSize="8" level="3" pageId="2" pageNumber="3" reason="8">
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<emphasis id="B967EAA6FF83FFABFE39F8817BEDF8E8" bold="true" box="[818,987,1878,1898]" italics="true" pageId="2" pageNumber="3">2.3. The effects of</emphasis>
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<emphasis id="B967EAA6FF83FFABFEE9F8817BC2F8E8" box="[994,1012,1879,1900]" italics="true" pageId="2" pageNumber="3">
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α
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<emphasis id="B967EAA6FF83FFABFEE5F8817BC2F8E8" bold="true" box="[1006,1012,1879,1898]" pageId="2" pageNumber="3">-</emphasis>
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</emphasis>
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<emphasis id="B967EAA6FF83FFABFEF8F8817C13F807" bold="true" italics="true" pageId="2" pageNumber="3">
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LA on the production of defensive specialized metabolites in
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<taxonomicName id="4C134D37FF83FFABFEBFF8A57C13F807" ID-CoL="79KXR" ID-ENA="203717" authority="(Turcz.) Schischk" authorityName="Schischk" baseAuthorityName="Turcz." box="[948,1061,1906,1926]" class="Magnoliopsida" family="Apiaceae" genus="Saposhnikovia" kingdom="Plantae" order="Apiales" pageId="2" pageNumber="3" phylum="Tracheophyta" rank="species" species="divaricata">S. divaricata</taxonomicName>
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</emphasis>
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</heading>
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</paragraph>
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</subSubSection>
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<subSubSection id="C309653FFF83FFAAFE5AF87D7994FADC" lastPageId="3" lastPageNumber="4" pageId="2" pageNumber="3" type="biology_ecology">
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<paragraph id="8BAC36B4FF83FFAAFE5AF87D7A12FC55" blockId="2.[849,1487,1963,1982]" lastBlockId="3.[100,770,797,1374]" lastPageId="3" lastPageNumber="4" pageId="2" pageNumber="3">
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Detailed comparative analysis of GC–MS data revealed that the contents of two compounds, (
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<emphasis id="B967EAA6FF82FFAAFCAEFCCB7985FCB2" bold="true" box="[421,435,797,816]" italics="true" pageId="3" pageNumber="4">R</emphasis>
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||
)-falcarinol and bergapten, were increased in the whole plant after α- LA treatment of the plant (
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<figureCitation id="13282A31FF82FFAAFFB5FCEF7AC2FCCE" box="[702,756,825,844]" captionStart="Fig" captionStartId="4.[818,848,1833,1850]" captionTargetBox="[824,1483,1379,1804]" captionTargetId="figure-230@4.[823,1484,1378,1805]" captionTargetPageId="4" captionText="Fig. 5. GC–MS TIC chromatograms of extracts of S. divaricata treated with water (1) or α-LA (2) for 5 days." figureDoi="http://doi.org/10.5281/zenodo.8259215" httpUri="https://zenodo.org/record/8259215/files/figure.png" pageId="3" pageNumber="4">Fig. 5</figureCitation>
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). The peaks were annotated or identified as shown in Table S3. The quantitative results of (
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<emphasis id="B967EAA6FF82FFAAFC4AFCA77979FC06" bold="true" box="[321,335,881,900]" italics="true" pageId="3" pageNumber="4">R</emphasis>
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)-falcarinol and bergapten contents are shown in
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<figureCitation id="13282A31FF82FFAAFD77FC5B7887FC22" box="[124,177,909,928]" captionStart="Fig" captionStartId="5.[100,130,565,582]" captionTargetBox="[109,764,150,532]" captionTargetId="graphics-1208@5.[200,437,200,525]" captionTargetPageId="5" captionText="Fig. 6. Accumulation of specialized metabolites in S. divaricata treated with α-LA or water for 5 days. Contents in fresh plants are shown. Values are presented as means ± SE with n = 3 plants per group. The differences were analyzed using Student’s t-test. The significance was set at *P <0.05 compared with water treatment (control)." figureDoi="http://doi.org/10.5281/zenodo.8259217" httpUri="https://zenodo.org/record/8259217/files/figure.png" pageId="3" pageNumber="4">Fig. 6</figureCitation>
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. There was a significant difference in the extent of the increase in (
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<emphasis id="B967EAA6FF82FFAAFD8EFC7F78A5FC3E" bold="true" box="[133,147,937,956]" italics="true" pageId="3" pageNumber="4">R</emphasis>
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)-falcarinol (
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<emphasis id="B967EAA6FF82FFAAFC01FC7F791DFC3E" box="[266,299,937,956]" italics="true" pageId="3" pageNumber="4">
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<emphasis id="B967EAA6FF82FFAAFC01FC7F7922FC3E" bold="true" box="[266,276,937,956]" italics="true" pageId="3" pageNumber="4">p</emphasis>
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<
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</emphasis>
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0.05). Similarly, the bergapten content tended to increase, but the difference was not significant.
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</paragraph>
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<caption id="DF6C663CFF82FFAAFD6FFD1F7B95FD76" ID-DOI="http://doi.org/10.5281/zenodo.8259211" ID-Zenodo-Dep="8259211" httpUri="https://zenodo.org/record/8259211/files/figure.png" pageId="3" pageNumber="4" startId="3.[100,130,713,730]" targetBox="[170,1418,149,685]" targetPageId="3" targetType="figure">
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<paragraph id="8BAC36B4FF82FFAAFD6FFD1F7B95FD76" blockId="3.[100,1488,713,757]" pageId="3" pageNumber="4">
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||
<emphasis id="B967EAA6FF82FFAAFD6FFD1F78ABFD58" bold="true" box="[100,157,713,730]" pageId="3" pageNumber="4">Fig. 3.</emphasis>
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Time course of induction of volatile components by α- LA or water treatment. GC–MS TIC chromatograms of
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<taxonomicName id="4C134D37FF82FFAAF937FD1F7C97FD58" box="[1084,1185,713,730]" class="Magnoliopsida" family="Apiaceae" genus="Saposhnikovia" kingdom="Plantae" order="Apiales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="divaricata">
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<emphasis id="B967EAA6FF82FFAAF937FD1F7C97FD58" bold="true" box="[1084,1185,713,730]" italics="true" pageId="3" pageNumber="4">S. divaricata</emphasis>
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</taxonomicName>
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treated with α- LA (A) or water (D),
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<taxonomicName id="4C134D37FF82FFAAFD6FFD3578F6FD76" box="[100,192,739,756]" class="Magnoliopsida" family="Apiaceae" genus="Cryptotaenia" kingdom="Plantae" order="Apiales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="japonica">
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<emphasis id="B967EAA6FF82FFAAFD6FFD3578F6FD76" bold="true" box="[100,192,739,756]" italics="true" pageId="3" pageNumber="4">C. japonica</emphasis>
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</taxonomicName>
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treated with α- LA (B) or water (E), and
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<taxonomicName id="4C134D37FF82FFAAFF16FD357A44FD76" box="[541,626,739,756]" class="Magnoliopsida" family="Apiaceae" genus="Petroselinum" kingdom="Plantae" order="Apiales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="crispum">
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<emphasis id="B967EAA6FF82FFAAFF16FD357A44FD76" bold="true" box="[541,626,739,756]" italics="true" pageId="3" pageNumber="4">P. crispum</emphasis>
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</taxonomicName>
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treated with α- LA (C) or water (F).
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</paragraph>
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</caption>
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<paragraph id="8BAC36B4FF82FFAAFD8FFC367994FADC" blockId="3.[100,770,797,1374]" pageId="3" pageNumber="4">
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<bibRefCitation id="EF824B45FF82FFAAFD8FFC367902FC71" author="Berenbaum, M." box="[132,308,992,1011]" pageId="3" pageNumber="4" pagination="163 - 179" refId="ref6775" refString="Berenbaum, M., 1983. Coumarins and caterpillars: a case for coevolution. Evolution 37, 163 - 179. https: // doi. org / 10.2307 / 2408184." type="journal article" year="1983">Berenbaum (1983)</bibRefCitation>
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reported that coumarin and its derivatives, linear and angular furanocoumarins, are toxic to Lepidopteran insects in the context of coevolution and furanocoumarins, such as bergapten, are more toxic to herbivores than coumarin. These compounds are thought to act as direct defense compounds in plants of the
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<taxonomicName id="4C134D37FF82FFAAFF41FB867AA9FBE1" box="[586,671,1104,1123]" class="Magnoliopsida" family="Rutaceae" kingdom="Plantae" order="Sapindales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="family">Rutaceae</taxonomicName>
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and
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<taxonomicName id="4C134D37FF82FFAAFFC4FB8678B8FBFD" baseAuthorityName="Wiklund" baseAuthorityYear="1975" class="Magnoliopsida" family="Apiaceae" kingdom="Plantae" order="Apiales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="family">Apiaceae</taxonomicName>
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families. Furthermore, studies have reported the insecticidal (mosquitocidal and nematocidal) activities of (
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<emphasis id="B967EAA6FF82FFAAFF3EFB5E7A75FB19" bold="true" box="[565,579,1160,1179]" italics="true" pageId="3" pageNumber="4">R</emphasis>
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)-falcarinol, a polyacetylene compound in
|
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<taxonomicName id="4C134D37FF82FFAAFC5EFB75799CFB34" baseAuthorityName="Wiklund" baseAuthorityYear="1975" box="[341,426,1187,1206]" class="Magnoliopsida" family="Apiaceae" kingdom="Plantae" order="Apiales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="family">Apiaceae</taxonomicName>
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and
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||
<taxonomicName id="4C134D37FF82FFAAFCE8FB757A70FB34" box="[483,582,1187,1206]" class="Magnoliopsida" family="Araliaceae" kingdom="Plantae" order="Apiales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="family">Araliaceae</taxonomicName>
|
||
plants (
|
||
<bibRefCitation id="EF824B45FF82FFAAFF96FB7578E1FB51" author="Eckenbach, U. & Lampman, R. L. & Seigler, D. S. & Ebinger, J. & Novak, R. J." pageId="3" pageNumber="4" pagination="1885 - 1893" refId="ref6993" refString="Eckenbach, U., Lampman, R. L., Seigler, D. S., Ebinger, J., Novak, R. J., 1999. Mosquitocidal activity of acetylenic compounds from Cryptotaenia canadensis. J. Chem. Ecol. 25, 1885 - 1893. https: // doi. org / 10.1023 / A: 1020938001272." type="journal article" year="1999">Eckenbach et al., 1999</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="EF824B45FF82FFAAFDECFB6979B4FB50" author="Liu, G. & Lai, D. W. & Liu, Q. Z. & Zhou, L. G. & Liu, Z. L." box="[231,386,1215,1235]" pageId="3" pageNumber="4" pagination="1276" refId="ref7806" refString="Liu, G., Lai, D. W., Liu, Q. Z., Zhou, L. G., Liu, Z. L., 2016. Identification of nematicidal constituents of Notopterygium incisum rhizomes against Bursaphelenchus xylophilus and Meloidogyne incognita. Molecules 21, 1276. https: // doi. org / 10.3390 / molecules 21101276." type="journal article" year="2016">Liu et al., 2016</bibRefCitation>
|
||
). In addition,
|
||
<bibRefCitation id="EF824B45FF82FFAAFF1EFB697B34FB51" author="Czyzewska, M. M. & Chrobok, L. & Kania, A. & Jatczak, M. & Pollastro, F. & Appendino, G. & Mozrzymas, J. W." box="[533,770,1215,1235]" pageId="3" pageNumber="4" pagination="2671 - 2677" refId="ref6918" refString="Czyzewska, M. M., Chrobok, L., Kania, A., Jatczak, M., Pollastro, F., Appendino, G., Mozrzymas, J. W., 2014. Dietary acetylenic oxylipin falcarinol differentially modulates GABAA receptors. J. Nat. Prod. 77, 2671 - 2677. https: // doi. org / 10.1021 / np 500615 j." type="journal article" year="2014">Czyzewska et al. (2014)</bibRefCitation>
|
||
indicated the potent insecticidal activity of falcarinol associated with γ- aminobutyric acidergic block in herbivorous insects. These results suggest that α- LA, a major component in the regurgitant of
|
||
<taxonomicName id="4C134D37FF82FFAAFF93FAC578FEFAC0" authorityName="C. Felder et R. Felder" authorityYear="1864" class="Insecta" family="Papilionidae" genus="Papilio" kingdom="Animalia" order="Lepidoptera" pageId="3" pageNumber="4" phylum="Arthropoda" rank="subSpecies" species="machaon" subSpecies="hippocrates">
|
||
<emphasis id="B967EAA6FF82FFAAFF93FAC578FEFAC0" bold="true" italics="true" pageId="3" pageNumber="4">P. machaon hippocrates</emphasis>
|
||
</taxonomicName>
|
||
larvae, can induce the biosynthesis of compounds involved in the direct defense of
|
||
<taxonomicName id="4C134D37FF82FFAAFC20FA9D79ADFADF" box="[299,411,1354,1374]" class="Magnoliopsida" family="Apiaceae" genus="Saposhnikovia" kingdom="Plantae" order="Apiales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="divaricata">
|
||
<emphasis id="B967EAA6FF82FFAAFC20FA9D79ADFADF" bold="true" box="[299,411,1354,1374]" italics="true" pageId="3" pageNumber="4">S. divaricata</emphasis>
|
||
</taxonomicName>
|
||
.
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |