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<document id="8D67EC1B84A7D574F2BE3D2F918751A9" ID-DOI="10.1016/j.phytochem.2015.12.009" ID-ISSN="1873-3700" ID-Zenodo-Dep="10485477" IM.bibliography_approvedBy="julia" IM.illustrations_approvedBy="julia" IM.materialsCitations_approvedBy="julia" IM.metadata_approvedBy="julia" IM.tables_approvedBy="julia" IM.taxonomicNames_approvedBy="julia" IM.treatments_approvedBy="julia" checkinTime="1704944972007" checkinUser="felipe" docAuthor="Stipanovic, Robert, Puckhaber, Lorraine, Jr., James Frelichowski, Esquivel, Jesus, Westbrook, John, ONeil, Mike, Bell, Alois, Dowd, Michael, Hake, Kater &amp; Duke, Sara" docDate="2016" docId="7144C772FF8FFFA1FCE99F19FD73F875" docLanguage="en" docName="Phytochemistry.122.165-171.pdf" docOrigin="Phytochemistry 122" docSource="http://dx.doi.org/10.1016/j.phytochem.2015.12.009" docStyle="DocumentStyle:9E596C34F4E94307D29315B03ACE1007.6:Phytochemistry.2014-2019.journal_article" docStyleId="9E596C34F4E94307D29315B03ACE1007" docStyleName="Phytochemistry.2014-2019.journal_article" docStyleVersion="6" docTitle="Helicoverpa zea subsp. larvae" docType="treatment" docVersion="1" lastPageNumber="167" masterDocId="8D7DBF0AFF8DFFA2FFD69C76FFC7FFAB" masterDocTitle="Gossypolhemiquinone, a dimeric sesquiterpenoid identified in cotton (Gossypium)" masterLastPageNumber="171" masterPageNumber="165" pageNumber="167" updateTime="1705342832530" updateUser="julia">
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<mods:title id="759CF4A55EF4F595C502B98362A4208A">Gossypolhemiquinone, a dimeric sesquiterpenoid identified in cotton (Gossypium)</mods:title>
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<mods:namePart id="89EAF0ACE240E7C0418095587BAE5E8E">Puckhaber, Lorraine</mods:namePart>
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<mods:namePart id="D8C6DF1B44B8E74EF139FA2227DCDB6D">Jr., James Frelichowski</mods:namePart>
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<mods:namePart id="DDB027A3478233527F46DC779B041125">Esquivel, Jesus</mods:namePart>
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<mods:namePart id="C9AF66743C4E1C7CEB0B5DF0EF586A76">Westbrook, John</mods:namePart>
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<mods:namePart id="6B1E6DE827B29A51C355A192099F856B">ONeil, Mike</mods:namePart>
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<mods:namePart id="8E634BA5B087C17FAF48A4F2602E09A4">Bell, Alois</mods:namePart>
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<mods:namePart id="CE648ADADD5CBF59AE3A78CE59D2B7CC">Dowd, Michael</mods:namePart>
<mods:affiliation id="ACE8E7C581B0A9DCEE88A5A9C6504411">USDA, Agricultural Research Service, Southern Regional Research Center, New Orleans, LA 70124, United States</mods:affiliation>
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<mods:namePart id="C2B93C215904B8F2B11709F1534145C9">Hake, Kater</mods:namePart>
<mods:affiliation id="F04181AEC56325E43F0CE1DC4F6999E6">Cotton Incorporated, 6399 Weston Parkway, Cary, NC 27513, United States</mods:affiliation>
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<mods:title id="84E49BD3B67B41401B5511D73163851E">Phytochemistry</mods:title>
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<treatment id="7144C772FF8FFFA1FCE99F19FD73F875" LSID="urn:lsid:plazi:treatment:7144C772FF8FFFA1FCE99F19FD73F875" httpUri="http://treatment.plazi.org/id/7144C772FF8FFFA1FCE99F19FD73F875" lastPageId="3" lastPageNumber="167" pageId="2" pageNumber="167">
<subSubSection id="B1F725EFFF8FFFA0FCE99F19FA02FC28" box="[831,1477,879,899]" pageId="2" pageNumber="167" type="nomenclature">
<paragraph id="F9527664FF8FFFA0FCE99F19FA02FC28" blockId="2.[831,1477,879,899]" box="[831,1477,879,899]" pageId="2" pageNumber="167">
<heading id="A21AC108FF8FFFA0FCE99F19FA02FC28" box="[831,1477,879,899]" fontSize="36" level="2" pageId="2" pageNumber="167" reason="3">
<emphasis id="CB99AA76FF8FFFA0FCE99F19FA02FC28" box="[831,1477,879,899]" italics="true" pageId="2" pageNumber="167">
2.4. Effect of GHQ (
<emphasis id="CB99AA76FF8FFFA0FC2F9F06FBC1FC28" bold="true" box="[1017,1030,880,899]" italics="true" pageId="2" pageNumber="167">9</emphasis>
) on growth and development of
<taxonomicName id="3EED0DE7FF8FFFA0FA919F19FA45FC28" authority="Boddie, 1850" box="[1351,1410,879,899]" class="Insecta" family="Noctuidae" genus="Helicoverpa" kingdom="Animalia" order="Lepidoptera" pageId="2" pageNumber="167" phylum="Arthropoda" rank="subSpecies" species="zea" subSpecies="larvae">H. zea</taxonomicName>
larvae
</emphasis>
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</paragraph>
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<subSubSection id="B1F725EFFF8FFFA1FC889FD1FD73F875" lastPageId="3" lastPageNumber="168" pageId="2" pageNumber="167" type="description">
<paragraph id="F9527664FF8FFFA0FC889FD1FB2DFA8E" blockId="2.[831,1501,935,2015]" pageId="2" pageNumber="167">
Since gossypol (
<emphasis id="CB99AA76FF8FFFA0FC2B9FD1FBCDFC11" bold="true" box="[1021,1034,935,954]" pageId="2" pageNumber="167">1</emphasis>
) and related terpenoids are important components in the plants arsenal of terpenoids that protect it from herbivorous insects, it seemed appropriate to test the toxicity of GHQ (
<emphasis id="CB99AA76FF8FFFA0FC919F8DFC93FBA5" bold="true" box="[839,852,1019,1038]" pageId="2" pageNumber="167">9</emphasis>
) to insects. Thus, racemic gossypol (
<emphasis id="CB99AA76FF8FFFA0FB0B9F8DFB2DFBA5" bold="true" box="[1245,1258,1019,1038]" pageId="2" pageNumber="167">1</emphasis>
) and racemic GHQ (
<emphasis id="CB99AA76FF8FFFA0FA119F8DFA13FBA5" bold="true" box="[1479,1492,1019,1038]" pageId="2" pageNumber="167">9</emphasis>
) were individually incorporated into a soybean artificial diet using the non-nutritive additive, Alphacel, at concentrations of 0.00% (control), 0.06%, 0.12% and 0.18%. To determine if GHQ (
<emphasis id="CB99AA76FF8FFFA0FA5F9839FA51FBC9" bold="true" box="[1417,1430,1103,1122]" pageId="2" pageNumber="167">9</emphasis>
) has a synergistic effect with gossypol (
<emphasis id="CB99AA76FF8FFFA0FB5A981DFB5EFBD5" bold="true" box="[1164,1177,1131,1150]" pageId="2" pageNumber="167">1</emphasis>
), diets were also prepared with a total concentration of terpenoids of 0.06%, 0.12% and 0.18%, and a 15.5:84.5 ratio of GHQ (
<emphasis id="CB99AA76FF8FFFA0FBE298D4FB86FB1E" bold="true" box="[1076,1089,1186,1205]" pageId="2" pageNumber="167">9</emphasis>
):gossypol (
<emphasis id="CB99AA76FF8FFFA0FB6198D4FB03FB1E" bold="true" box="[1207,1220,1186,1205]" pageId="2" pageNumber="167">1</emphasis>
). One-day-old
<taxonomicName id="3EED0DE7FF8FFFA0FA8A98D7FA1BFB1E" box="[1372,1500,1185,1205]" class="Insecta" family="Noctuidae" genus="Helicoverpa" kingdom="Animalia" order="Lepidoptera" pageId="2" pageNumber="167" phylum="Arthropoda" rank="subSpecies" species="zea" subSpecies="larvae">
<emphasis id="CB99AA76FF8FFFA0FA8A98D7FA5FFB1E" box="[1372,1432,1185,1205]" italics="true" pageId="2" pageNumber="167">H. zea</emphasis>
larvae
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were placed in plastic cups containing the various diets described above. After pupation, the pupae were allowed to harden for one day and then weighed. Days-to-pupation, pupal weights and percent survival to adulthood were recorded.
</paragraph>
<paragraph id="F9527664FF8FFFA0FC889958FA90F98B" blockId="2.[831,1501,935,2015]" pageId="2" pageNumber="167">
The mean number days-to-pupation increased as the concentration of gossypol (
<emphasis id="CB99AA76FF8FFFA0FC3B993CFC3DFAF6" bold="true" box="[1005,1018,1354,1373]" pageId="2" pageNumber="167">1</emphasis>
) and GHQ (
<emphasis id="CB99AA76FF8FFFA0FBA4993CFBB8FAF6" bold="true" box="[1138,1151,1354,1373]" pageId="2" pageNumber="167">9</emphasis>
) increased compared to larvae fed the control diet (
<figureCitation id="61D66AE1FF8FFFA0FC3A9910FBE4FAD2" box="[1004,1059,1382,1401]" captionStart="Fig" captionStartId="3.[87,113,1750,1764]" captionTargetBox="[108,731,1335,1726]" captionTargetId="graphics-701@3.[157,724,1359,1708]" captionTargetPageId="3" captionText="Fig. 2. Mean number (with standard error bars) of days-to-pupation for Helicoverpa zea one-day-old larvae fed various concentrations of gossypol (1) or gossypolhemiquinone (GHQ) (9) or a 15.5:84.5 mixture of GHQ (9):gossypol (1) in an artificial diet." figureDoi="http://doi.org/10.5281/zenodo.10485481" httpUri="https://zenodo.org/record/10485481/files/figure.png" pageId="2" pageNumber="167">Fig. 2</figureCitation>
). However, the difference in days-to-pupation between the larvae fed the gossypol (
<emphasis id="CB99AA76FF8FFFA0FB2899F7FACCFA3F" bold="true" box="[1278,1291,1409,1428]" pageId="2" pageNumber="167">1</emphasis>
) and GHQ (
<emphasis id="CB99AA76FF8FFFA0FA5A99F7FA5EFA3F" bold="true" box="[1420,1433,1409,1428]" pageId="2" pageNumber="167">9</emphasis>
) were not significantly different. When the larvae were fed the 15.5:84.5 mixtures of GHQ (
<emphasis id="CB99AA76FF8FFFA0FBF799CFFBE9FA67" bold="true" box="[1057,1070,1465,1484]" pageId="2" pageNumber="167">9</emphasis>
) and gossypol (
<emphasis id="CB99AA76FF8FFFA0FB2199CFFAC3FA67" bold="true" box="[1271,1284,1465,1484]" pageId="2" pageNumber="167">1</emphasis>
), an extension in days-to-pupation was not observed at the 0.06% and 0.12% concentrations. However, at the 0.18% concentration, the days-to-pupation were significantly longer compared to all other diets.
</paragraph>
<paragraph id="F9527664FF8FFFA0FC889A5FFC34F948" blockId="2.[831,1501,935,2015]" pageId="2" pageNumber="167">
The mean pupal weights (
<figureCitation id="61D66AE1FF8FFFA0FBB49A5FFB5FF997" box="[1122,1176,1577,1596]" captionStart="Fig" captionStartId="3.[805,831,1350,1364]" captionTargetBox="[840,1442,966,1321]" captionTargetId="graphics-863@3.[881,1442,971,1321]" captionTargetPageId="3" captionText="Fig. 3. Mean (with standard error bars) pupal weights for Helicoverpa zea one-dayold larvae fed various concentrations of gossypol (1) or gossypolhemiquinone (GHQ) (9) or a 15.5:84.5 mixture of GHQ (9):gossypol (1) in an artificial diet." figureDoi="http://doi.org/10.5281/zenodo.10485479" httpUri="https://zenodo.org/record/10485479/files/figure.png" pageId="2" pageNumber="167">Fig. 3</figureCitation>
) were significantly less for diets containing 0.12% and 0.18% gossypol (
<emphasis id="CB99AA76FF8FFFA0FB689A33FB0CF9F3" bold="true" box="[1214,1227,1605,1624]" pageId="2" pageNumber="167">1</emphasis>
), GHQ (
<emphasis id="CB99AA76FF8FFFA0FACA9A33FAEEF9F3" bold="true" box="[1308,1321,1605,1624]" pageId="2" pageNumber="167">9</emphasis>
), or the 15.5:84.5 mixture of the two terpenoids compared to those fed the control diet. However, pupal weights for larvae fed gossypol (
<emphasis id="CB99AA76FF8FFFA0FAB59A0BFAB7F93B" bold="true" box="[1379,1392,1661,1680]" pageId="2" pageNumber="167">1</emphasis>
) were significantly less than those fed an equivalent concentration of GHQ (
<emphasis id="CB99AA76FF8FFFA0FC919AC2FC93F96C" bold="true" box="[839,852,1716,1735]" pageId="2" pageNumber="167">9</emphasis>
). No synergistic effect in reducing pupal weight was observed with the mixture.
</paragraph>
<paragraph id="F9527664FF8FFFA1FC889A9AFD73F875" blockId="2.[831,1501,935,2015]" lastBlockId="3.[87,757,1912,2015]" lastPageId="3" lastPageNumber="168" pageId="2" pageNumber="167">
The percent survival to adulthood of larvae fed 0.06% gossypol (
<emphasis id="CB99AA76FF8FFFA0FC919B7EFC93F8B0" bold="true" box="[839,852,1800,1819]" pageId="2" pageNumber="167">1</emphasis>
) or the 0.06% 15.5:84.5 GHQ (
<emphasis id="CB99AA76FF8FFFA0FB7B9B7EFB7DF8B0" bold="true" box="[1197,1210,1800,1819]" pageId="2" pageNumber="167">9</emphasis>
):gossypol (
<emphasis id="CB99AA76FF8FFFA0FAE09B7EFA84F8B0" bold="true" box="[1334,1347,1800,1819]" pageId="2" pageNumber="167">1</emphasis>
) mixture was greater than the control (
<figureCitation id="61D66AE1FF8FFFA0FB9F9B52FB45F89C" box="[1097,1154,1828,1847]" captionStart="Fig" captionStartId="3.[805,831,1821,1835]" captionTargetBox="[821,1460,1485,1792]" captionTargetId="graphics-1006@3.[883,1457,1489,1792]" captionTargetPageId="3" captionText="Fig. 4. Percent survival for Helicoverpa zea larvae fed various concentrations of gossypol (1), gossypolhemiquinone (GHQ) (9) or a 15.5:84.5 mixture of GHQ (9):gossypol (1) in an artificial diet." figureDoi="http://doi.org/10.5281/zenodo.10485483" httpUri="https://zenodo.org/record/10485483/files/figure.png" pageId="2" pageNumber="167">Fig. 4</figureCitation>
). This may be due to a hormetic effect (i.e., a biphasic doseresponse exhibited by some toxic substances when fed at low concentrations) that has been demonstrated in other gossypol (
<emphasis id="CB99AA76FF8FFFA0FB8A9B0EFBAEF820" bold="true" box="[1116,1129,1912,1931]" pageId="2" pageNumber="167">1</emphasis>
) feeding studies (
<bibRefCitation id="9D7C0B95FF8FFFA0FAFB9B0EFCB1F80C" author="Stipanovic, R. D. &amp; Williams, H. J. &amp; Smith, L." pageId="2" pageNumber="167" pagination="79 - 94" refId="ref8753" refString="Stipanovic, R. D., Williams, H. J., Smith, L., 1986. Cotton terpenoid inhibition of Heliothis virescens development. In: Green, M. A., Hedin, P. A. (Eds.), Natural Resistance of Plants to Pests, Symposium Series # 296. American Chemical Society, Washington, DC, pp. 79 - 94." type="proceedings paper" year="1986">Stipanovic et al., 1986</bibRefCitation>
;
<bibRefCitation id="9D7C0B95FF8FFFA0FC549BE2FB60F80C" author="Celorio-Mancera, M. P. &amp; Ahn, S. J. &amp; Vogel, H. &amp; Heckel, D. G." box="[898,1191,1940,1959]" pageId="2" pageNumber="167" pagination="575 - 590" refId="ref7587" refString="Celorio-Mancera, M. P., Ahn, S. J., Vogel, H., Heckel, D. G., 2011. Transcriptional responses underlying the hormetic and detrimental effects of the plant secondary metabolite gossypol on the generalist herbivore Helicoverpa armigera. BMC Genomics 12, 575 - 590." type="journal article" year="2011">Celorio-Mancera et al., 2011</bibRefCitation>
). Survival of larvae fed 0.06% or 0.12% GHQ (
<emphasis id="CB99AA76FF8FFFA0FC0A9BD9FC2EF869" bold="true" box="[988,1001,1967,1986]" pageId="2" pageNumber="167">9</emphasis>
) or the 15.5:84.5 mixtures were not affected. At 0.18%, gossypol (
<emphasis id="CB99AA76FF8FFFA0FC389BBDFC3CF875" bold="true" box="[1006,1019,1995,2014]" pageId="2" pageNumber="167">1</emphasis>
) and GHQ (
<emphasis id="CB99AA76FF8FFFA0FBAA9BBDFB4EF875" bold="true" box="[1148,1161,1995,2014]" pageId="2" pageNumber="167">9</emphasis>
) reduced survival with gossypol (
<emphasis id="CB99AA76FF8EFFA1FF899B0EFFABF820" bold="true" box="[95,108,1912,1931]" pageId="3" pageNumber="168">1</emphasis>
) showing mortality&gt;50% compared to larvae fed the control diet. However, the survival to adulthood of larvae fed the 0.18% 15.5:84.5 GHQ (
<emphasis id="CB99AA76FF8EFFA1FF2D9BD9FECFF869" bold="true" box="[251,264,1967,1986]" pageId="3" pageNumber="168">9</emphasis>
):gossypol (
<emphasis id="CB99AA76FF8EFFA1FEA89BD9FE4CF869" bold="true" box="[382,395,1967,1986]" pageId="3" pageNumber="168">1</emphasis>
) diet was less than one-third those fed the control diet indicating a potential synergistic effect.
</paragraph>
</subSubSection>
</treatment>
</document>