treatments-xml/data/03/F8/87/03F88786C314FFD1F81448FCFA42FAA8.xml
2024-06-21 12:22:17 +02:00

187 lines
26 KiB
XML
Raw Permalink Blame History

This file contains ambiguous Unicode characters

This file contains Unicode characters that might be confused with other characters. If you think that this is intentional, you can safely ignore this warning. Use the Escape button to reveal them.

<document id="D01FF1094C65F1F5CA71ED4F3D8AF0CF" ID-DOI="10.1016/j.phytochem.2021.112734" ID-ISSN="1873-3700" ID-Zenodo-Dep="8258534" IM.bibliography_approvedBy="diego" IM.illustrations_approvedBy="diego" IM.materialsCitations_approvedBy="diego" IM.metadata_approvedBy="felipe" IM.tables_approvedBy="diego" IM.taxonomicNames_approvedBy="diego" IM.treatments_approvedBy="diego" checkinTime="1692306212869" checkinUser="felipe" docAuthor="de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A. &amp; Henriques, Amelia T." docDate="2021" docId="03F88786C314FFD1F81448FCFA42FAA8" docLanguage="en" docName="Phytochemistry.186.112734.pdf" docOrigin="Phytochemistry (112734) 186" docSource="http://dx.doi.org/10.1016/j.phytochem.2021.112734" docStyle="DocumentStyle:F36D69FC8B198FBE91029DF9C24697D3.5:Phytochemistry.2020-.journal_article" docStyleId="F36D69FC8B198FBE91029DF9C24697D3" docStyleName="Phytochemistry.2020-.journal_article" docStyleVersion="5" docTitle="Grazielia gaudichaudeana" docType="treatment" docVersion="3" lastPageNumber="2" masterDocId="FFC1FFFEC315FFD3FD584E1BFFD7FF8D" masterDocTitle="Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae" masterLastPageNumber="23" masterPageNumber="1" pageNumber="2" updateTime="1692635409478" updateUser="ExternalLinkService">
<mods:mods id="0075C0980D22AE0667F123FCCF8BAB5A" xmlns:mods="http://www.loc.gov/mods/v3">
<mods:titleInfo id="8F9FDB421585B9D4F7CD48480BF53534">
<mods:title id="417088CEED8C5E5AA91BB2B6836D04A6">Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae</mods:title>
</mods:titleInfo>
<mods:name id="12C8EF9DB98227BEC6E31B3DA8BD4394" type="personal">
<mods:role id="24D9477F229E28CBBBC180BC18E0897E">
<mods:roleTerm id="F2BF2BE4EFF43EB038E3E20A455212B7">Author</mods:roleTerm>
</mods:role>
<mods:namePart id="639C38993A2AFA62C3BD1E73513DD5EF">de Souza, Tiago J. T.</mods:namePart>
<mods:affiliation id="9FAB7BB432BD6634460566DFA4723E34">* &amp; Faculdade de Farm´acia, Universidade Federal do Rio Grande do Sul (UFRGS), Av. Ipiranga, 2752, 90610 - 000, Porto Alegre, Brazil</mods:affiliation>
</mods:name>
<mods:name id="2AF44E6F0DD2577F5BC6E3FE71491CEF" type="personal">
<mods:role id="ACABD5F4BBD95D8103A699312CC69C8F">
<mods:roleTerm id="F644C476C684A7B90599170AC2AD99E4">Author</mods:roleTerm>
</mods:role>
<mods:namePart id="51DBF20AD2CE6F6CDCB643A12167CF60">S</mods:namePart>
</mods:name>
<mods:name id="DB7B0C290020891E30DF5A0F93CAAAB9" type="personal">
<mods:role id="AD55E9BC9AC5C42AF56345D541437A9E">
<mods:roleTerm id="F2FC092B5E41A7BD11E2A9FF16EBDF8C">Author</mods:roleTerm>
</mods:role>
<mods:namePart id="8C375CCAD240EDEA130937424E6D0FEB">Bordignon, ergio A. L.</mods:namePart>
<mods:affiliation id="C401D1982326D68EC0F96F71C1ED8CEF">Programa de P´os-Graduaç ˜ ao em Avaliaç ˜ ao de Impactos Ambientais, Centro Universit´ario La Salle, Canoas, Brazil</mods:affiliation>
</mods:name>
<mods:name id="C4B3EB39357C0D44A16697F43E455B06" type="personal">
<mods:role id="DE90678A99C566A45BC4683B0F38ADB7">
<mods:roleTerm id="6A1B1B5474712A78AE14F43C138E3C43">Author</mods:roleTerm>
</mods:role>
<mods:namePart id="0BE920D863FDF9BB21236E81C1262169">Apel, Miriam A.</mods:namePart>
</mods:name>
<mods:name id="63F30061ED78A080F346A05DA36A3E20" type="personal">
<mods:role id="BE7AB1FEFDF04D15C0F6623A08CE9431">
<mods:roleTerm id="310F370A9D95B6FF4AC6F12BC62CF2EC">Author</mods:roleTerm>
</mods:role>
<mods:namePart id="AA5C1143077EB9AE589FBA26312E9D78">Henriques, Amelia T.</mods:namePart>
</mods:name>
<mods:typeOfResource id="DFA80C75F768C7F9223D1698B51E477B">text</mods:typeOfResource>
<mods:relatedItem id="AF4DA70F24E566C4D54B8137AFC1E202" type="host">
<mods:titleInfo id="837FE51B91BB8E65C9B6FD3C962237FB">
<mods:title id="7D35807687836BACB4F7C575BB6D46A8">Phytochemistry</mods:title>
</mods:titleInfo>
<mods:part id="B3003844DEB97A93B573DBCF763893D0">
<mods:date id="9C2A78F36FC45E0A5F44BD4FCAE280A4">2021</mods:date>
<mods:detail id="D469B5495CC929640BF6519533E9BD8E" type="series">
<mods:title id="C0F9905F3928094B8F0928619B559070">112734</mods:title>
</mods:detail>
<mods:detail id="43F56779F20D5B5419583ABD1A9A93FF" type="pubDate">
<mods:number id="9734E214C1764C8285A4B0B2A0A0F43D">2021-06-30</mods:number>
</mods:detail>
<mods:detail id="9C0EEDB96383086280E49FBC2FB9F146" type="volume">
<mods:number id="69C5F2483C0F5B8F011E5161FFC89EF6">186</mods:number>
</mods:detail>
<mods:extent id="A87E1AE018CA6DBD45F0649272D96D0B" unit="page">
<mods:start id="5300469CC267E0A02E0007C974E800DD">1</mods:start>
<mods:end id="CDA893B69D8D325104FF9D0791AA4EC4">23</mods:end>
</mods:extent>
</mods:part>
</mods:relatedItem>
<mods:location id="DD427EDD32A0BB020DFC541AC57BAEC0">
<mods:url id="ECC23FB89191FF23F627AAE0D0DADD10">http://dx.doi.org/10.1016/j.phytochem.2021.112734</mods:url>
</mods:location>
<mods:classification id="3D0862FC2D4B584B0C514E62A00D74B5">journal article</mods:classification>
<mods:identifier id="0E18A181F868288491B78B012AD67720" type="DOI">10.1016/j.phytochem.2021.112734</mods:identifier>
<mods:identifier id="8D959B37434BE4D1B8F5550D0A53E177" type="ISSN">1873-3700</mods:identifier>
<mods:identifier id="5A4B6BF519C6450FF024F686E575253E" type="Zenodo-Dep">8258534</mods:identifier>
</mods:mods>
<treatment id="03F88786C314FFD1F81448FCFA42FAA8" ID-DOI="http://doi.org/10.5281/zenodo.8270307" ID-Zenodo-Dep="8270307" LSID="urn:lsid:plazi:treatment:03F88786C314FFD1F81448FCFA42FAA8" httpUri="http://treatment.plazi.org/id/03F88786C314FFD1F81448FCFA42FAA8" lastPageId="2" lastPageNumber="2" pageId="1" pageNumber="2">
<subSubSection id="C34B651BC314FFD2F81448FCFB41F89B" pageId="1" pageNumber="2" type="nomenclature">
<paragraph id="8BEE3690C314FFD2F81448FCFB41F89B" blockId="1.[818,1488,1460,1983]" pageId="1" pageNumber="2">
<taxonomicName id="4C514D13C314FFD2F81448FCFC0AF89B" authority="(DC.)" baseAuthorityName="DC." class="Magnoliopsida" family="Asteraceae" genus="Grazielia" kingdom="Plantae" order="Asterales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="gaudichaudeana">
<emphasis id="B925EA82C314FFD2F81448FCFC74F89B" bold="true" italics="true" pageId="1" pageNumber="2">Grazielia gaudichaudeana</emphasis>
(DC.)
</taxonomicName>
R.M.King &amp; H.Rob
</paragraph>
</subSubSection>
<subSubSection id="C34B651BC314FFD2F9C54918FB98F8BF" pageId="1" pageNumber="2" type="reference_group">
<paragraph id="8BEE3690C314FFD2F9C54918FB98F8BF" blockId="1.[818,1488,1460,1983]" pageId="1" pageNumber="2">
(=
<emphasis id="B925EA82C314FFD2F9E54918FB90F8BF" bold="true" italics="true" pageId="1" pageNumber="2">
<taxonomicName id="4C514D13C314FFD2F9E54918FA1CF89B" authorityName="DC." box="[1213,1483,1795,1814]" class="Magnoliopsida" family="Asteraceae" genus="Eupatorium" kingdom="Plantae" order="Asterales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="gaudichaudianum">Eupatorium gaudichaudianum</taxonomicName>
,
<taxonomicName id="4C514D13C314FFD2FE6A4904FB90F8BF" authorityName="DC." box="[818,1095,1823,1842]" class="Magnoliopsida" family="Asteraceae" genus="Dimorpholepis" kingdom="Plantae" order="Asterales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="gaudichaudeana">Dimorpholepis gaudichaudeana</taxonomicName>
</emphasis>
)
</paragraph>
</subSubSection>
<subSubSection id="C34B651BC314FFD1F90E4904FA42FAA8" lastPageId="2" lastPageNumber="3" pageId="1" pageNumber="2" type="discussion">
<paragraph id="8BEE3690C314FFD1F90E4904FA42FAA8" blockId="1.[818,1488,1460,1983]" lastBlockId="2.[818,1488,1019,1959]" lastPageId="2" lastPageNumber="3" pageId="1" pageNumber="2">
were collected in Canela and Paraíso do Sul, which exhibited VOs with very similar chemical compositions in terms of the monoterpene fraction. The major compounds in this fraction were α- pinene (12.415.5%), β- pinene (9.228.9%), and limonene (18.337.2%). The sample from Canela/05 also showed a large percentage of α- thujene (10.1%). In the sesquiterpene fraction, the VOs presented large quantitative differences. The VOs obtained from a region of higher altitude (Canela) were characterized by the presence of sesquiterpene hydrocarbon compounds with a germacrane nucleus, namely germacrene D and bicyclogermacrene (11.3 and 7.6%), these compounds did not reach 2% of the VOs obtained from the Paraíso do Sul/06 sample. In the VOs from the samples obtained from the lower central region, this fraction was characterized by the predominance of an oxygenated compound with an aromadendrane nucleus, spathulenol (20.5 and 9.4% in the leaves and inflorescences, respectively). The transformation of bicyclogermacrene and germacrene D into spathulenol has already been reported (
<bibRefCitation id="EFC04B61C317FFD1FCDE4B09FDE2FAA8" author="Toyota" box="[390,565,1298,1317]" etAl="et al." firstAuthor="Toyota" pageId="2" pageNumber="3" pagination="1347 - 1350" refId="ref18529" refString="Toyota, M., Koyama, H., Mizutani, M., Asakawa, Y., 1996. (-) - ENT-spathulenol isolated from liverworts is an artefact. Phytochemistry 41, 1347 - 1350. https: // doi. org / 10.1016 / 0031 - 9422 (95) 00798 - 9." type="journal article" year="1996">Toyota et al., 1996</bibRefCitation>
;
<bibRefCitation id="EFC04B61C317FFD1FF184B09FD23FAA8" author="Venturi" box="[576,756,1298,1317]" etAl="et al." firstAuthor="Venturi" pageId="2" pageNumber="3" pagination="682 - 688" refId="ref18931" refString="Venturi, C. R., Danielli, L. J., Klein, F., Apel, M. A., Montanha, J. A., Bordignon, S. A. L., Roehe, P. M., Fuentefria, A. M., Henriques, A. T., 2015. Chemical analysis and in vitro antiviral and antifungal activities of essential oils from Glechon spathulata and Glechon marifolia. Pharm. Biol. 53, 682 - 688. https: // doi. org / 10.3109 / 13880209.2014. 936944." type="journal article" year="2015">Venturi et al., 2015</bibRefCitation>
). Previously, several diterpenes bearing an ent-caurane nucleus have been isolated from this species collected in S˜ao Paulo state (
<bibRefCitation id="EFC04B61C317FFD1FF014B52FD2DFAD0" author="Taleb" box="[601,762,1353,1373]" etAl="et al." firstAuthor="Taleb" pageId="2" pageNumber="3" pagination="547 - 549" refId="ref18315" refString="Taleb, S. H., De Oliveira, D. C. R., Lopes, J. L. C., 1999. Constituents of Grazielia gaudichaudiana (Asteraceae). Biochem. Syst. Ecol. 27, 547 - 549. https: // doi. org / 10.1016 / S 0305 - 1978 (98) 00104 - 5." type="journal article" year="1999">Taleb et al., 1999</bibRefCitation>
) and from a sample collected in
<collectingRegion id="4995F872C317FFD1FCD24B7DFE1CFAF4" box="[394,459,1382,1401]" country="Brazil" name="Parana" pageId="2" pageNumber="3">Parana</collectingRegion>
´state, a cytotoxic 18-nor-ent-labdane furan was isolated together with sterols, triterpenes, and flavonols (
<bibRefCitation id="EFC04B61C317FFD1FD344B86FEFFFA3D" author="Balbinot" box="[108,296,1437,1457]" etAl="et al." firstAuthor="Balbinot" pageId="2" pageNumber="3" pagination="1800644" refId="ref12653" refString="Balbinot, R. B., de Oliveira, J. A. M., Bernardi, D. I., Melo, U. Z., Zanqueta, E´. B., Endo, E. H., Ribeiro, F. M., Volpato, H., Figueiredo, M. C., Back, D. F., Basso, E. A., Ruiz, A. L. T. G., de Carvalho, J. E., Foglio, M. A., Prado Filho, B. D., Nakamura, T. U., Nakamura, C. V., do Carmo, M. R. B., Sarragiotto, M. H., Baldoqui, D. C., 2019. Structural characterization and biological evaluation of 18 - Nor-ent-labdane Diterpenoids from Grazielia gaudichaudeana. Chem. Biodivers. 16, e 1800644 https: // doi. org / 10.1002 / cbdv. 201800644." type="journal article" year="2019">Balbinot et al., 2019</bibRefCitation>
). The yield of the VOs has already been reported to be 1.091.29% (in dry and fresh inflorescences, respectively), which was in the same range as our samples, but the chemical composition has not been previously reported (
<bibRefCitation id="EFC04B61C317FFD1FC314BEAFE37F989" author="Souza" box="[361,480,1521,1540]" firstAuthor="Souza" pageId="2" pageNumber="3" refId="ref17917" refString="Souza, M. T. de, 2015. Bioprospecctao da flora arom´atica de um segmento de floresta Ombrofila´Mista Montana do Parana´." type="book" year="2015">Souza, 2015</bibRefCitation>
). In Southeastern
<collectingCountry id="F3467600C317FFD1FFC14BEAFD05F989" box="[665,722,1521,1540]" name="Brazil" pageId="2" pageNumber="3">Brazil</collectingCountry>
, this species has been reported to be associated with
<taxonomicName id="4C514D13C317FFD1FF464816FD7EF9AD" box="[542,681,1549,1568]" class="Insecta" family="Cecidomyiidae" kingdom="Animalia" order="Diptera" pageId="2" pageNumber="3" phylum="Arthropoda" rank="family">Cecidomyiidae</taxonomicName>
stem gall inducers (
<bibRefCitation id="EFC04B61C317FFD1FD9C4832FEABF9B1" author="Coelho" box="[196,380,1577,1596]" etAl="et al." firstAuthor="Coelho" pageId="2" pageNumber="3" pagination="139 - 151" refId="ref13436" refString="Coelho, M. S., Carneiro, M. A. A., Branco, C., Borges, R. A. X., Fernandes, G. W., 2013. Gallinducing insects from campos de Altitude, Brazil. Biota Neotrop 13, 139 - 151. https: // doi. org / 10.1590 / s 1676 - 06032013000400015." type="journal article" year="2013">Coelho et al., 2013</bibRefCitation>
) and an unknown lepidopteran leaf gall inducer whose galls were occupied by coleopterans (
<bibRefCitation id="EFC04B61C317FFD1FF28485FFF25F9F9" author="Maia and Mascarenhas" firstAuthor="Maia" pageId="2" pageNumber="3" pagination="505 - 575" refId="ref15785" refString="Maia, V. C., Mascarenhas, B., 2017. Insect galls of the parque nacional do Itatiaia (Southeast region, Brazil). An. Acad. Bras. Cienc. 89, 505 - 575. https: // doi. org / 10.1590 / 0001 - 3765201720160877." type="journal article" year="2017">Maia and Mascarenhas, 2017</bibRefCitation>
). In addition, its flower heads have been reported to be a feeding site for adults of the very endangered endemic
<taxonomicName id="4C514D13C317FFD1FFDC4867FCD5F902" box="[644,770,1660,1679]" class="Insecta" family="Nymphalidae" kingdom="Animalia" order="Lepidoptera" pageId="2" pageNumber="3" phylum="Arthropoda" rank="family">Nymphalidae</taxonomicName>
butterfly
<taxonomicName id="4C514D13C317FFD1FDE34883FDC5F926" authority="(Francini et al., 2005)" baseAuthorityName="Francini" baseAuthorityYear="2005" box="[187,530,1688,1708]" class="Insecta" family="Nymphalidae" genus="Actinote" kingdom="Animalia" order="Lepidoptera" pageId="2" pageNumber="3" phylum="Arthropoda" rank="species" species="zikani">
<emphasis id="B925EA82C317FFD1FDE34883FE97F926" bold="true" box="[187,320,1688,1707]" italics="true" pageId="2" pageNumber="3">Actinote zikani</emphasis>
(
<bibRefCitation id="EFC04B61C317FFD1FC154883FDDEF926" author="Francini" box="[333,521,1688,1708]" etAl="et al." firstAuthor="Francini" pageId="2" pageNumber="3" pagination="134 - 142" refId="ref14217" refString="Francini, R. B., Freitas, A. V. L., Brown, K. S., 2005. Rediscovery of Actinote zikani (D' Almeida) (Nymphalidae, heliconiinae, Acraeini): natural history, population biology and conservation of an endangered butterfly in SE Brazil. J. Lepid. Soc. 59, 134 - 142." type="journal article" year="2005">Francini et al., 2005</bibRefCitation>
)
</taxonomicName>
, the threatened Pierideae butterfly
<taxonomicName id="4C514D13C317FFD1FDE748AFFDE5F94A" authority="(Freitas et al., 2011)" baseAuthorityName="Freitas" baseAuthorityYear="2011" box="[191,562,1716,1735]" class="Insecta" family="Pieridae" genus="Charonias" kingdom="Animalia" order="Lepidoptera" pageId="2" pageNumber="3" phylum="Arthropoda" rank="species" species="theano">
<emphasis id="B925EA82C317FFD1FDE748AFFE88F94A" bold="true" box="[191,351,1716,1735]" italics="true" pageId="2" pageNumber="3">Charonias theano</emphasis>
(
<bibRefCitation id="EFC04B61C317FFD1FC2848AFFDFDF94A" author="Freitas" box="[368,554,1716,1735]" etAl="et al." firstAuthor="Freitas" pageId="2" pageNumber="3" pagination="669 - 676" refId="ref14400" refString="Freitas, A. V. L., Kaminski, L. A., Iserhard, C. A., Barbosa, E. P., Filho, O. J. M., 2011. The endangered butterfly charonias theano (Boisduval) (Lepidoptera: Pieridae): Current status, threats and its rediscovery in the state of Stao Paulo, Southeastern Brazil. Neotrop. Entomol. 40, 669 - 676. https: // doi. org / 10.1590 / S 1519 - 566 X 2011000600006." type="journal article" year="2011">Freitas et al., 2011</bibRefCitation>
)
</taxonomicName>
, and the Ithomiiniae
<taxonomicName id="4C514D13C317FFD1FD3C48CBFEF4F96E" box="[100,291,1744,1763]" class="Insecta" family="Nymphalidae" genus="Placidula" kingdom="Animalia" order="Lepidoptera" pageId="2" pageNumber="3" phylum="Arthropoda" rank="species" species="euryanassa">
<emphasis id="B925EA82C317FFD1FD3C48CBFEF4F96E" bold="true" box="[100,291,1744,1763]" italics="true" pageId="2" pageNumber="3">Placidula euryanassa</emphasis>
</taxonomicName>
(which also feeds on other
<taxonomicName id="4C514D13C317FFD1FF6348CBFD79F96E" box="[571,686,1744,1763]" class="Magnoliopsida" family="Asteraceae" genus="Eupatorieae" higherTaxonomySource="GBIF" kingdom="Plantae" order="Asterales" pageId="2" pageNumber="1" phylum="Tracheophyta" rank="genus">Eupatorieae</taxonomicName>
, such as
<taxonomicName id="4C514D13C317FFD1FD3C48F0FEE7F973" box="[100,304,1771,1790]" class="Magnoliopsida" family="Asteraceae" genus="Chromolaena" kingdom="Plantae" order="Asterales" pageId="2" pageNumber="3" phylum="Tracheophyta" rank="species" species="laevigata">
<emphasis id="B925EA82C317FFD1FD3C48F0FEE7F973" bold="true" box="[100,304,1771,1790]" italics="true" pageId="2" pageNumber="3">Chromolaena laevigata</emphasis>
</taxonomicName>
and
<taxonomicName id="4C514D13C317FFD1FC3848F7FDEEF973" box="[352,569,1771,1791]" class="Magnoliopsida" family="Asteraceae" genus="Barrosoa" kingdom="Plantae" order="Asterales" pageId="2" pageNumber="3" phylum="Tracheophyta" rank="species" species="betoniciiformis">
<emphasis id="B925EA82C317FFD1FC3848F7FDEEF973" bold="true" box="[352,569,1771,1791]" italics="true" pageId="2" pageNumber="3">Barrosoa betoniciiformis</emphasis>
</taxonomicName>
) (
<bibRefCitation id="EFC04B61C317FFD1FF1748F7FD1DF972" author="Freitas" box="[591,714,1772,1791]" firstAuthor="Freitas" pageId="2" pageNumber="3" pagination="87 - 105" refId="ref14285" refString="Freitas, A. V. L., 1993. Biology and population dynamics of Placidula euryanassa, a relict ithomiine butterfly (Nymphalidae: ithomiinae). J. Lepid. Soc. 47, 87 - 105." type="journal article" year="1993">Freitas, 1993</bibRefCitation>
). The role of VOs in the interactions between plants and insects, gall inducers, leaf-suckers, and leaf-eaters has been previously studied (
<bibRefCitation id="EFC04B61C317FFD1FFC8493FFF43F8DE" author="Jiang" etAl="et al." firstAuthor="Jiang" pageId="2" pageNumber="3" pagination="160 - 175" refId="ref15338" refString="Jiang, Y., Veromann-Jurgenson, L., Ye, J., Niinemets, U., 2018. Oak gall wasp infections of Quercus robur leaves lead to profound modifications in foliage photosynthetic and volatile emission characteristics. Plant Cell Environ. 41, 160 - 175." type="journal article" year="2018">Jiang et al., 2018</bibRefCitation>
; Rost´as et al., 2013; Tooker et al., 2008;
<bibRefCitation id="EFC04B61C317FFD1FF7C495BFF43F8E2" author="Tooker and De Moraes" firstAuthor="Tooker" pageId="2" pageNumber="3" pagination="503 - 504" refId="ref18438" refString="Tooker, J. F., De Moraes, C. M., 2008. Gall insects and indirect plant defenses: a case of active manipulation? Plant Signal. Behav. 3, 503 - 504." type="journal article" year="2008">Tooker and De Moraes, 2008</bibRefCitation>
). For instance,
<taxonomicName id="4C514D13C317FFD1FC684940FE3EF8E3" box="[304,489,1883,1902]" class="Insecta" family="Lasiocampidae" genus="Malacosoma" kingdom="Animalia" order="Lepidoptera" pageId="2" pageNumber="3" phylum="Arthropoda" rank="species" species="disstria">
<emphasis id="B925EA82C317FFD1FC684940FE3EF8E3" bold="true" box="[304,489,1883,1902]" italics="true" pageId="2" pageNumber="3">Malacosoma disstria</emphasis>
</taxonomicName>
caterpillars induce a germacrene D synthase in
<taxonomicName id="4C514D13C317FFD1FC71496CFE0CF807" box="[297,475,1911,1930]" class="Magnoliopsida" family="Salicaceae" genus="Populus" kingdom="Plantae" order="Malpighiales" pageId="2" pageNumber="3" phylum="Tracheophyta" rank="species" species="trichocarpa">
<emphasis id="B925EA82C317FFD1FC71496CFE0CF807" bold="true" box="[297,475,1911,1930]" italics="true" pageId="2" pageNumber="3">Populus trichocarpa</emphasis>
</taxonomicName>
×
<emphasis id="B925EA82C317FFD1FCA4496CFD9EF807" bold="true" box="[508,585,1911,1930]" italics="true" pageId="2" pageNumber="3">deltoides</emphasis>
by feeding on that species, possibly implying a role for this compound in attracting the caterpillar s natural enemies in a tri-trophic interaction (
<bibRefCitation id="EFC04B61C317FFD1F81E4DE0FCB5FBA7" author="Arimura" etAl="et al." firstAuthor="Arimura" pageId="2" pageNumber="3" pagination="603 - 616" refId="ref12580" refString="Arimura, G., Huber, D. P. W., Bohlmann, J., 2004. Forest tent caterpillars (Malacosoma disstria) induce local and systemic diurnal emissions of terpenoid volatiles in hybrid poplar (Populus trichocarpa × deltoides): cDNA cloning, functional characterization, and patterns of gene expression of () - germacre. Plant J. 37, 603 - 616." type="journal article" year="2004">Arimura et al., 2004</bibRefCitation>
). On the other hand, the moth
<taxonomicName id="4C514D13C317FFD1F9C34A0DFAE8FBA7" baseAuthorityName="Fabricius" baseAuthorityYear="1777" box="[1179,1343,1046,1066]" class="Insecta" family="Noctuidae" genus="Heliothis" higherTaxonomySource="GBIF" kingdom="Animalia" order="Lepidoptera" pageId="2" pageNumber="3" phylum="Arthropoda" rank="species" species="virescens">
<emphasis id="B925EA82C317FFD1F9C34A0DFAE8FBA7" bold="true" box="[1179,1343,1046,1066]" italics="true" pageId="2" pageNumber="3">Heliothis virescens</emphasis>
</taxonomicName>
(
<taxonomicName id="4C514D13C317FFD1F8164A0CFA66FBA7" box="[1358,1457,1047,1066]" class="Insecta" family="Noctuidae" kingdom="Animalia" order="Lepidoptera" pageId="2" pageNumber="3" phylum="Arthropoda" rank="family">Noctuidae</taxonomicName>
) is attracted by ()-germacrene D in tobacco, enhancing oviposition in the plant (
<bibRefCitation id="EFC04B61C317FFD1FE374A55FB96FBEF" author="Mozuraitis" box="[879,1089,1102,1122]" etAl="et al." firstAuthor="Mozuraitis" pageId="2" pageNumber="3" pagination="505 - 509" refId="ref16276" refString="Mozuraitis, R., Stranden, M., Ramirez, M. I., Borg-Karlson, A. - K., Mustaparta, H., 2002. (-) - Germacrene D increases attraction and oviposition by the tobacco budworm moth Heliothis virescens. Chem. Senses 27, 505 - 509." type="journal article" year="2002">Mozuraitis et al., 2002</bibRefCitation>
;
<bibRefCitation id="EFC04B61C317FFD1F9144A54FAC6FBEF" author="Rostelien" box="[1100,1297,1102,1122]" etAl="et al." firstAuthor="Rostelien" pageId="2" pageNumber="3" pagination="141 - 148" refId="ref17375" refString="Rostelien, T., Borg-Karlson, A. - K., F ¨ aldt, J., Jacobsson, U., Mustaparta, H., 2000. The plant sesquiterpene germacrene D specifically activates a major type of antennal receptor neuron of the tobacco budworm moth Heliothis virescens. Chem. Senses 25, 141 - 148." type="journal article" year="2000">Røstelien et al., 2000</bibRefCitation>
). Limonene exhibits insect repellent activity (
<bibRefCitation id="EFC04B61C317FFD1F97E4A71FB3BFBF0" author="Hebeish" box="[1062,1260,1130,1150]" etAl="et al." firstAuthor="Hebeish" pageId="2" pageNumber="3" pagination="268 - 273" refId="ref15121" refString="Hebeish, A., Fouda, M. M. G., Hamdy, I. A., El-Sawy, S. M., Abdel-Mohdy, F. A., 2008. Preparation of durable insect repellent cotton fabric: limonene as insecticide. Carbohydr. Polym. 74, 268 - 273." type="journal article" year="2008">Hebeish et al., 2008</bibRefCitation>
;
<bibRefCitation id="EFC04B61C317FFD1F9A34A71FA16FBF0" author="Tripathi" box="[1275,1473,1130,1150]" etAl="et al." firstAuthor="Tripathi" pageId="2" pageNumber="3" pagination="990 - 995" refId="ref18589" refString="Tripathi, A. K., Prajapati, V., Khanuja, S. P. S., Kumar, S., 2003. Effect of d-limonene on three stored-product beetles. J. Econ. Entomol. 96, 990 - 995." type="journal article" year="2003">Tripathi et al., 2003</bibRefCitation>
), while β- pinene has also been shown to be neurotoxic to the coleopteran
<taxonomicName id="4C514D13C317FFD1FE6A4AB9FC2AFB38" baseAuthorityName="Herbst" baseAuthorityYear="1797" box="[818,1021,1186,1205]" class="Insecta" family="Tenebrionidae" genus="Tribolium" kingdom="Animalia" order="Coleoptera" pageId="2" pageNumber="3" phylum="Arthropoda" rank="species" species="castaneum">
<emphasis id="B925EA82C317FFD1FE6A4AB9FC2AFB38" bold="true" box="[818,1021,1186,1205]" italics="true" pageId="2" pageNumber="3">Tribolium castaneum</emphasis>
</taxonomicName>
by inducing the overexpression of the histamine-gated chloride channel 2 (Hiscl2), GABA-gated ion channel (Grd), and acetylcholinesterase (Ace1) Ace1 genes (
<bibRefCitation id="EFC04B61C317FFD1F84E4AC1FCB5FA84" author="Pajaro-Castro" etAl="et al." firstAuthor="Pajaro-Castro" pageId="2" pageNumber="3" pagination="2052" refId="ref16480" refString="Pajaro-Castro, N., Caballero-Gallardo, K., Olivero-Verbel, J., 2017. Neurotoxic effects of linalool and β- pinene on Tribolium castaneum Herbst. Molecules 22, 2052." type="journal article" year="2017">Pajaro-Castro et al., 2017</bibRefCitation>
). The role of the VOs produced by
<taxonomicName id="4C514D13C317FFD1F9EC4AEDFAB1FA85" box="[1204,1382,1269,1289]" class="Magnoliopsida" family="Asteraceae" genus="Grazielia" kingdom="Plantae" order="Asterales" pageId="2" pageNumber="3" phylum="Tracheophyta" rank="species" species="gaudichaudieana">
<emphasis id="B925EA82C317FFD1F9EC4AEDFAB1FA85" bold="true" box="[1204,1382,1269,1289]" italics="true" pageId="2" pageNumber="3">G. gaudichaudieana</emphasis>
</taxonomicName>
during the interaction of this species with insects remains to be established.
</paragraph>
</subSubSection>
</treatment>
</document>