227 lines
23 KiB
XML
227 lines
23 KiB
XML
<document id="DCC1615D3B6B594FEABC448DD47C5BA9" ID-CLB-Dataset="285319" ID-DOI="10.1016/j.phytochem.2015.12.009" ID-GBIF-Dataset="5b997348-5f35-4147-812e-77402b84742b" 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, O’Neil, Mike, Bell, Alois, Dowd, Michael, Hake, Kater & Duke, Sara" docDate="2016" docId="7144C772FF8FFFA0FFA49B2DFC5BFCE0" 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="Gossypium" docType="treatment" docVersion="3" lastPageNumber="167" masterDocId="8D7DBF0AFF8DFFA2FFD69C76FFC7FFAB" masterDocTitle="Gossypolhemiquinone, a dimeric sesquiterpenoid identified in cotton (Gossypium)" masterLastPageNumber="171" masterPageNumber="165" pageNumber="167" updateTime="1705343815314" updateUser="ExternalLinkService">
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<mods:title id="6F042C331212AE8204FB885486738D13">Gossypolhemiquinone, a dimeric sesquiterpenoid identified in cotton (Gossypium)</mods:title>
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<mods:namePart id="6BAB31DDAFFBBDD567CB107CA46A48FC">Stipanovic, Robert</mods:namePart>
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<mods:namePart id="BF8ACD4E093720CB26435F4C0476C79F">Puckhaber, Lorraine</mods:namePart>
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<mods:affiliation id="3DD17403588C17ECBFD8E3F68507BC6F">USDA, Agricultural Research Service, Southern Plains Agricultural Research Center, College Station, TX 77845, United States</mods:affiliation>
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<mods:namePart id="64C9934B3AD3DACC3ACA15388A8288A8">Jr., James Frelichowski</mods:namePart>
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<mods:namePart id="873B434A7DFE9CAB72F40ABF6BDBC257">Esquivel, Jesus</mods:namePart>
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<mods:affiliation id="D698872E23F1CA4187B30B9320115D6F">USDA, Agricultural Research Service, Southern Plains Agricultural Research Center, College Station, TX 77845, United States</mods:affiliation>
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<mods:namePart id="9B92A3107D72AC2E9D010FAD9FDC505F">Westbrook, John</mods:namePart>
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<mods:affiliation id="7968EE448F2F465827769E85BB4D0757">USDA, Agricultural Research Service, Southern Plains Agricultural Research Center, College Station, TX 77845, United States</mods:affiliation>
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<mods:namePart id="81F96A0EE756D826683FB8BA418B06C2">O’Neil, Mike</mods:namePart>
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<mods:namePart id="C51DA9ECDAEF7EC0D303AED1D0C27CED">Bell, Alois</mods:namePart>
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<mods:affiliation id="5FF609C0F6D18A9837FAE1D8CFFABDE7">USDA, Agricultural Research Service, Southern Plains Agricultural Research Center, College Station, TX 77845, United States</mods:affiliation>
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<mods:namePart id="A77DB0E74EF498A4CCC164B30581B8BA">Dowd, Michael</mods:namePart>
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<mods:affiliation id="472B59EC05229FB74033780792ECEBEE">USDA, Agricultural Research Service, Southern Regional Research Center, New Orleans, LA 70124, United States</mods:affiliation>
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<mods:namePart id="214BADD717EA187AE70DD702D648121C">Hake, Kater</mods:namePart>
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<mods:affiliation id="A42E2DB4FEC58806BEAAA634AABC392B">Cotton Incorporated, 6399 Weston Parkway, Cary, NC 27513, United States</mods:affiliation>
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<mods:namePart id="492C710DE7D953DB8C8801F6E8832187">Duke, Sara</mods:namePart>
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<mods:affiliation id="E4988A79AEE98C155DE8B827F795034B">USDA, Agricultural Research Service, Southern Plains Agricultural Research Center, College Station, TX 77845, United States</mods:affiliation>
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<mods:title id="E28A80657B3097D039150735E07C8C71">Phytochemistry</mods:title>
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<mods:date id="50122D7529C4285FE1D2CAA77126F61D">2016</mods:date>
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<mods:number id="03EBBE65AD6D35A1E0C3209457760D7D">2016-02-29</mods:number>
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<mods:number id="A8D75FA6E903DA8B922B03FA783D29E3">122</mods:number>
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<treatment id="7144C772FF8FFFA0FFA49B2DFC5BFCE0" ID-DOI="http://doi.org/10.5281/zenodo.10514919" ID-Zenodo-Dep="10514919" LSID="urn:lsid:plazi:treatment:7144C772FF8FFFA0FFA49B2DFC5BFCE0" httpUri="http://treatment.plazi.org/id/7144C772FF8FFFA0FFA49B2DFC5BFCE0" lastPageNumber="167" pageId="2" pageNumber="167">
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<subSubSection id="B1F725EFFF8FFFA0FFA49B2DFEE9F820" pageId="2" pageNumber="167" type="nomenclature">
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<emphasis id="CB99AA76FF8FFFA0FFA49B2DFEE9F820" italics="true" pageId="2" pageNumber="167">
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2.3. GHQ (
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<emphasis id="CB99AA76FF8FFFA0FF019B2AFF23F8C4" bold="true" box="[215,228,1884,1903]" italics="true" pageId="2" pageNumber="167">9</emphasis>
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) and gossypol (
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<emphasis id="CB99AA76FF8FFFA0FEA89B2AFE4CF8C4" bold="true" box="[382,395,1884,1903]" italics="true" pageId="2" pageNumber="167">1</emphasis>
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) in the D genome of
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<taxonomicName id="3EED0DE7FF8FFFA0FD8D9B2DFD03F8C4" ID-CoL="4QG7" ID-ENA="3633" authority="L." box="[603,708,1883,1903]" class="Magnoliopsida" family="Malvaceae" genus="Gossypium" kingdom="Plantae" order="Malvales" pageId="2" pageNumber="167" phylum="Tracheophyta" rank="genus">Gossypium</taxonomicName>
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and in commercial cottons
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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="B1F725EFFF8FFFA0FF479BD9FC5BFCE0" pageId="2" pageNumber="167" type="description">
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<paragraph id="F9527664FF8FFFA0FF479BD9FC5BFCE0" blockId="2.[113,783,1967,2015]" lastBlockId="2.[831,1501,182,843]" pageId="2" pageNumber="167">
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<taxonomicName id="3EED0DE7FF8FFFA0FF479BD9FF3FF868" box="[145,248,1967,1987]" class="Magnoliopsida" family="Malvaceae" genus="Gossypium" kingdom="Plantae" order="Malvales" pageId="2" pageNumber="167" phylum="Tracheophyta" rank="species" species="thurberi">
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<emphasis id="CB99AA76FF8FFFA0FF479BD9FF3FF868" box="[145,248,1967,1987]" italics="true" pageId="2" pageNumber="167">G. thurberi</emphasis>
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||
</taxonomicName>
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is a member of the D genome of
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||
<taxonomicName id="3EED0DE7FF8FFFA0FD909BD9FD69F868" box="[582,686,1967,1987]" class="Magnoliopsida" family="Malvaceae" genus="Gossypium" kingdom="Plantae" order="Malvales" pageId="2" pageNumber="167" phylum="Tracheophyta" rank="genus">
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<emphasis id="CB99AA76FF8FFFA0FD909BD9FD69F868" box="[582,686,1967,1987]" italics="true" pageId="2" pageNumber="167">Gossypium</emphasis>
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||
</taxonomicName>
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||
. In a previous investigation of terpenoids in the young leaves of
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<taxonomicName id="3EED0DE7FF8FFFA0FD719BBCFCC8F875" box="[679,783,1994,2014]" class="Magnoliopsida" family="Malvaceae" genus="Gossypium" kingdom="Plantae" order="Malvales" pageId="2" pageNumber="167" phylum="Tracheophyta" rank="species" species="thurberi">
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<emphasis id="CB99AA76FF8FFFA0FD719BBCFCC8F875" box="[679,783,1994,2014]" italics="true" pageId="2" pageNumber="167">G. thurberi</emphasis>
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</taxonomicName>
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using TLC plates, only gossypol (
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<emphasis id="CB99AA76FF8FFFA0FB4E9CC0FB62FF62" bold="true" box="[1176,1189,182,201]" pageId="2" pageNumber="167">1</emphasis>
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) was identified in this tissue (
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<bibRefCitation id="9D7C0B95FF8FFFA0FC919CA4FBE9FF4E" author="Stipanovic, R. D. & Bell, A. A. & Lukefahr, M. J." box="[839,1070,210,230]" pageId="2" pageNumber="167" pagination="197 - 214" refId="ref8524" refString="Stipanovic, R. D., Bell, A. A., Lukefahr, M. J., 1977. Natural insecticides from cotton (Gossypium). In: Hedin, P. A. (Ed.), Host Plant Resistance to Pests, Symposium Series # 62. American Chemical Society, Washington, DC, pp. 197 - 214." type="proceedings paper" year="1977">Stipanovic et al., 1977</bibRefCitation>
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). Thus, terpenoids such as the sesquiterpenoid hemigossypolone (
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<emphasis id="CB99AA76FF8FFFA0FB999C98FB9BFEAA" bold="true" box="[1103,1116,238,257]" pageId="2" pageNumber="167">7</emphasis>
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) and the sesterterpenoids heliocides
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,
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,
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<subScript id="65697421FF8FFFA0FC749D65FC6CFEB4" attach="left" box="[930,939,275,287]" fontSize="5" pageId="2" pageNumber="167">3</subScript>
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and
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<collectionCode id="9FFCEEA1FF8FFFA0FC319D7CFC30FEB6" box="[999,1015,266,285]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="2" pageNumber="167" type="Herbarium">H</collectionCode>
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<subScript id="65697421FF8FFFA0FC219D65FBC7FEB4" attach="left" box="[1015,1024,275,287]" fontSize="5" pageId="2" pageNumber="167">4</subScript>
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(
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<emphasis id="CB99AA76FF8FFFA0FBC29D7CFBFDFEB6" bold="true" box="[1044,1082,266,285]" pageId="2" pageNumber="167">3–6</emphasis>
|
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) (
|
||
<figureCitation id="61D66AE1FF8FFFA0FB839D7CFB57FEB6" box="[1109,1168,266,285]" captionStart="Fig" captionStartId="1.[578,604,1125,1139]" captionTargetBox="[405,1147,184,1093]" captionTargetPageId="1" captionText="Fig. 1. Terpenoids identified in Gossypium foliage." figureDoi="http://doi.org/10.5281/zenodo.10514962" httpUri="https://zenodo.org/record/10514962/files/figure.png" pageId="2" pageNumber="167">Fig. 1</figureCitation>
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) that are found in commercial Upland cottons (
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||
<taxonomicName id="3EED0DE7FF8FFFA0FC3B9D53FB71FE92" box="[1005,1206,293,313]" class="Magnoliopsida" family="Malvaceae" genus="Gossypium" kingdom="Plantae" order="Malvales" pageId="2" pageNumber="167" phylum="Tracheophyta" rank="species" species="hirsutum">
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||
<emphasis id="CB99AA76FF8FFFA0FC3B9D53FB71FE92" box="[1005,1206,293,313]" italics="true" pageId="2" pageNumber="167">Gossypium hirsutum</emphasis>
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||
</taxonomicName>
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), as well as other members of
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<taxonomicName id="3EED0DE7FF8FFFA0FC8E9D37FC07FEFE" box="[856,960,321,341]" class="Magnoliopsida" family="Malvaceae" genus="Gossypium" kingdom="Plantae" order="Malvales" pageId="2" pageNumber="167" phylum="Tracheophyta" rank="genus">
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<emphasis id="CB99AA76FF8FFFA0FC8E9D37FC07FEFE" box="[856,960,321,341]" italics="true" pageId="2" pageNumber="167">Gossypium</emphasis>
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||
</taxonomicName>
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, were not found. To extend this investigation, several
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<taxonomicName id="3EED0DE7FF8FFFA0FCE99D2BFC6FFEDA" box="[831,936,349,369]" class="Magnoliopsida" family="Malvaceae" genus="Gossypium" kingdom="Plantae" order="Malvales" pageId="2" pageNumber="167" phylum="Tracheophyta" rank="genus">
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<emphasis id="CB99AA76FF8FFFA0FCE99D2BFC6FFEDA" box="[831,936,349,369]" italics="true" pageId="2" pageNumber="167">Gossypium</emphasis>
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</taxonomicName>
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accessions of the D genome available in the USDA Cotton Germplasm collection were grown in the greenhouse; leaves were collected, freeze dried, and ground. The ground tissue was extracted and immediately subjected to
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<collectionCode id="9FFCEEA1FF8FFFA0FB0E9DC7FACAFE6F" box="[1240,1293,433,452]" pageId="2" pageNumber="167">HPLC</collectionCode>
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analysis; the results are shown in
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<tableCitation id="B46F43DFFF8FFFA0FC1C9DBBFBD3FE4B" box="[970,1044,461,480]" captionStart="Table 3" captionStartId="3.[87,131,183,197]" captionTargetPageId="3" captionText="Table 3 Concentration of gossypol (Goss) (1) and gossypolhemiquinone (GHQ) (9) in freeze dried leaves of select D genome Gossypium greenhouse grown plants." httpUri="http://table.plazi.org/id/AD9226ECFF8EFFA1FF819CC1FADEFF77" pageId="2" pageNumber="167" tableUuid="AD9226ECFF8EFFA1FF819CC1FADEFF77">Table 3</tableCitation>
|
||
. As found previously, other sesquiterpenoids and sesterterpenoids normally in
|
||
<taxonomicName id="3EED0DE7FF8FFFA0FB459D9EFAC3FE57" box="[1171,1284,488,508]" class="Magnoliopsida" family="Malvaceae" genus="Gossypium" kingdom="Plantae" order="Malvales" pageId="2" pageNumber="167" phylum="Tracheophyta" rank="species" species="hirsutum">
|
||
<emphasis id="CB99AA76FF8FFFA0FB459D9EFAC3FE57" box="[1171,1284,488,508]" italics="true" pageId="2" pageNumber="167">G. hirsutum</emphasis>
|
||
</taxonomicName>
|
||
were not detected in
|
||
<taxonomicName id="3EED0DE7FF8FFFA0FCE99E72FC61FDB3" box="[831,934,516,536]" class="Magnoliopsida" family="Malvaceae" genus="Gossypium" kingdom="Plantae" order="Malvales" pageId="2" pageNumber="167" phylum="Tracheophyta" rank="species" species="thurberi">
|
||
<emphasis id="CB99AA76FF8FFFA0FCE99E72FC61FDB3" box="[831,934,516,536]" italics="true" pageId="2" pageNumber="167">G. thurberi</emphasis>
|
||
</taxonomicName>
|
||
nor in most other members of the D genome. However, GHQ (
|
||
<emphasis id="CB99AA76FF8FFFA0FCAB9E57FC4DFD9F" bold="true" box="[893,906,545,564]" pageId="2" pageNumber="167">9</emphasis>
|
||
) was present in small amounts in these cottons. As previously reported (
|
||
<bibRefCitation id="9D7C0B95FF8FFFA0FC369E4BFB07FDFB" author="Stipanovic, R. D. & Bell, A. A. & Lukefahr, M. J." box="[992,1216,573,592]" pageId="2" pageNumber="167" pagination="197 - 214" refId="ref8524" refString="Stipanovic, R. D., Bell, A. A., Lukefahr, M. J., 1977. Natural insecticides from cotton (Gossypium). In: Hedin, P. A. (Ed.), Host Plant Resistance to Pests, Symposium Series # 62. American Chemical Society, Washington, DC, pp. 197 - 214." type="proceedings paper" year="1977">Stipanovic et al., 1977</bibRefCitation>
|
||
), within the D genome only the leaves of
|
||
<taxonomicName id="3EED0DE7FF8FFFA0FC2E9E2EFAA5FDC7" authority="(Ulbrich)" baseAuthorityName="Ulbrich" box="[1016,1378,600,620]" class="Magnoliopsida" family="Malvaceae" genus="Gossypium" kingdom="Plantae" order="Malvales" pageId="2" pageNumber="167" phylum="Tracheophyta" rank="species" species="gossypioides">
|
||
<emphasis id="CB99AA76FF8FFFA0FC2E9E2EFB28FDC7" box="[1016,1263,600,620]" italics="true" pageId="2" pageNumber="167">Gossypium gossypioides</emphasis>
|
||
(Ulbrich)
|
||
</taxonomicName>
|
||
contained hemigossypolone (
|
||
<emphasis id="CB99AA76FF8FFFA0FBD49E03FBC8FD23" bold="true" box="[1026,1039,629,648]" pageId="2" pageNumber="167">7</emphasis>
|
||
) and heliocides (
|
||
<emphasis id="CB99AA76FF8FFFA0FB189E02FB33FD2C" bold="true" box="[1230,1268,628,648]" pageId="2" pageNumber="167">3–6</emphasis>
|
||
); the leaves of other members of the D genome did not contain these terpenoids. In addition, the leaves of
|
||
<taxonomicName id="3EED0DE7FF8FFFA0FBE29EDDFB68FD14" box="[1076,1199,683,703]" class="Magnoliopsida" family="Malvaceae" genus="Gossypium" kingdom="Plantae" order="Malvales" pageId="2" pageNumber="167" phylum="Tracheophyta" rank="species" species="raimondii">
|
||
<emphasis id="CB99AA76FF8FFFA0FBE29EDDFB68FD14" box="[1076,1199,683,703]" italics="true" pageId="2" pageNumber="167">G. raimondii</emphasis>
|
||
</taxonomicName>
|
||
contained only gossypol (
|
||
<emphasis id="CB99AA76FF8FFFA0FA119EDAFA13FD14" bold="true" box="[1479,1492,684,703]" pageId="2" pageNumber="167">1</emphasis>
|
||
) and the sesquiterpenoid, raimondal (
|
||
<emphasis id="CB99AA76FF8FFFA0FB6B9EBEFB0DFD70" bold="true" box="[1213,1226,712,731]" pageId="2" pageNumber="167">8</emphasis>
|
||
) (
|
||
<figureCitation id="61D66AE1FF8FFFA0FB349EBEFADDFD70" box="[1250,1306,712,731]" captionStart="Fig" captionStartId="1.[578,604,1125,1139]" captionTargetBox="[405,1147,184,1093]" captionTargetPageId="1" captionText="Fig. 1. Terpenoids identified in Gossypium foliage." figureDoi="http://doi.org/10.5281/zenodo.10514962" httpUri="https://zenodo.org/record/10514962/files/figure.png" pageId="2" pageNumber="167">Fig. 1</figureCitation>
|
||
). Four commercial cultivars of
|
||
<taxonomicName id="3EED0DE7FF8FFFA0FC6E9E95FBEDFD5C" box="[952,1066,739,759]" class="Magnoliopsida" family="Malvaceae" genus="Gossypium" kingdom="Plantae" order="Malvales" pageId="2" pageNumber="167" phylum="Tracheophyta" rank="species" species="hirsutum">
|
||
<emphasis id="CB99AA76FF8FFFA0FC6E9E95FBEDFD5C" box="[952,1066,739,759]" italics="true" pageId="2" pageNumber="167">G. hirsutum</emphasis>
|
||
</taxonomicName>
|
||
cotton also were analyzed (
|
||
<tableCitation id="B46F43DFFF8FFFA0FA9B9E92FA5FFD5C" box="[1357,1432,740,759]" captionStart="Table 4" captionStartId="3.[87,131,964,978]" captionTargetPageId="3" captionText="Table 4 Concentration (µg/mg) of gossypol (Goss) (1), hemigossypolone (HGQ) (7), heliocides H1–4 (3–6) and gossypolhemiquinone (GHQ) (9) in freeze dried leaves of commercial cultivars (the HPLC method did not separate heliocide H1 (3) from heliocide H3 (6); gossypolone (2) was not detected." httpUri="http://table.plazi.org/id/AD9226ECFF8EFFA1FF819FB2FEAFFB86" pageId="2" pageNumber="167" tableUuid="AD9226ECFF8EFFA1FF819FB2FEAFFB86">Table 4</tableCitation>
|
||
). GHQ (
|
||
<emphasis id="CB99AA76FF8FFFA0FC919F76FC93FCB8" bold="true" box="[839,852,768,787]" pageId="2" pageNumber="167">9</emphasis>
|
||
) was not detected in these plants, but, as expected, gossypol (
|
||
<emphasis id="CB99AA76FF8FFFA0FC919F6AFC93FC84" bold="true" box="[839,852,796,815]" pageId="2" pageNumber="167">1</emphasis>
|
||
), hemigossypolone (
|
||
<emphasis id="CB99AA76FF8FFFA0FBEA9F6AFB8EFC84" bold="true" box="[1084,1097,796,815]" pageId="2" pageNumber="167">7</emphasis>
|
||
) and heliocides
|
||
<collectionCode id="9FFCEEA1FF8FFFA0FAC69F6AFAE7FC84" box="[1296,1312,796,815]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="2" pageNumber="167" type="Herbarium">H</collectionCode>
|
||
<subScript id="65697421FF8FFFA0FAF79F53FAEDFC9A" attach="right" box="[1313,1322,805,817]" fontSize="5" pageId="2" pageNumber="167">1</subScript>
|
||
–
|
||
<collectionCode id="9FFCEEA1FF8FFFA0FAE09F6AFA80FC84" box="[1334,1351,796,815]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="2" pageNumber="167" type="Herbarium">H</collectionCode>
|
||
<subScript id="65697421FF8FFFA0FA919F53FA97FC9A" attach="left" box="[1351,1360,805,817]" fontSize="5" pageId="2" pageNumber="167">4</subScript>
|
||
(
|
||
<emphasis id="CB99AA76FF8FFFA0FABC9F6AFA56FC84" bold="true" box="[1386,1425,796,815]" pageId="2" pageNumber="167">3–6</emphasis>
|
||
) were detected.
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |