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<document id="29A3BC002100F763CA715634A9B5DD34" ID-CLB-Dataset="55368" ID-DOI="10.1016/j.phytochem.2021.112662" ID-GBIF-Dataset="c2a0cd6a-4d45-4488-9357-509b5fa38fc8" ID-ISSN="1873-3700" ID-Zenodo-Dep="8259664" IM.bibliography_approvedBy="carolina" 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="1692309280030" checkinUser="felipe" docAuthor="Barny, Lea A., Tasca, Julia A., Sanchez, Hugo A., Smith, Chelsea R., Koptur, Suzanne, Livshultz, Tatyana &amp; Minbiole, Kevin P. C." docDate="2021" docId="06510721387BFFC403649B41545BFC52" docLanguage="en" docName="Phytochemistry.185.112662.pdf" docOrigin="Phytochemistry (112662) 185" docSource="http://dx.doi.org/10.1016/j.phytochem.2021.112662" docStyle="DocumentStyle:F36D69FC8B198FBE91029DF9C24697D3.5:Phytochemistry.2020-.journal_article" docStyleId="F36D69FC8B198FBE91029DF9C24697D3" docStyleName="Phytochemistry.2020-.journal_article" docStyleVersion="5" docTitle="Malouetieae" docType="treatment" docVersion="3" lastPageNumber="8" masterDocId="FA687F59387CFFC303009E6B511BFF90" masterDocTitle="Chemotaxonomic investigation of Apocynaceae for retronecine-type pyrrolizidine alkaloids using HPLC-MS / MS" masterLastPageNumber="15" masterPageNumber="1" pageNumber="8" updateTime="1692713795367" updateUser="ExternalLinkService">
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<mods:title id="7AB8D7DA02C82C49F67B3F2F0C977D09">Chemotaxonomic investigation of Apocynaceae for retronecine-type pyrrolizidine alkaloids using HPLC-MS / MS</mods:title>
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<mods:namePart id="65932B26FC6E2D1FF75B6098289D4702">Barny, Lea A.</mods:namePart>
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<mods:namePart id="FC924B3E62F6EB876C6BB919C7BE982E">Tasca, Julia A.</mods:namePart>
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<mods:namePart id="81B0641BFD16EC78467D40F7EA8A010B">Sanchez, Hugo A.</mods:namePart>
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<mods:namePart id="0EF4F2B80DB40448ED661886D070384C">Smith, Chelsea R.</mods:namePart>
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<mods:namePart id="B88105AEFCFB5363A5AD25379AD929AB">Koptur, Suzanne</mods:namePart>
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<mods:namePart id="29D824A37BF389FBD5F0790EC1B93137">Livshultz, Tatyana</mods:namePart>
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<mods:namePart id="5F427E66B50127F9ACEB00E391A72866">Minbiole, Kevin P. C.</mods:namePart>
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<mods:date id="FFA5D21C1F1FD292A2B26C53FA972A85">2021</mods:date>
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<treatment id="06510721387BFFC403649B41545BFC52" LSID="urn:lsid:plazi:treatment:06510721387BFFC403649B41545BFC52" httpUri="http://treatment.plazi.org/id/06510721387BFFC403649B41545BFC52" lastPageNumber="8" pageId="7" pageNumber="8">
<subSubSection id="C6E2E5BC387BFFC403649B41501AFAAD" box="[100,257,1322,1341]" pageId="7" pageNumber="8" type="nomenclature">
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<emphasis id="BC8C6A25387BFFC403649B41501AFAAD" bold="true" box="[100,257,1322,1341]" italics="true" pageId="7" pageNumber="8">
2.5.
<taxonomicName id="49F8CDB4387BFFC403959B41501AFAAD" box="[149,257,1322,1341]" class="Magnoliopsida" family="Apocynaceae" kingdom="Plantae" order="Gentianales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="tribe">Malouetieae</taxonomicName>
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<paragraph id="8E47B637387BFFC403849B0955B6FE77" blockId="7.[100,771,1378,1593]" lastBlockId="7.[818,1488,384,962]" pageId="7" pageNumber="8">
Eleven species from nine of 13 genera of Malouetieae were sampled. PAs were detected with moderate confidence in
<taxonomicName id="49F8CDB4387BFFC401349B155219FA01" authority="Stapf" authorityName="Stapf" box="[564,770,1406,1425]" class="Magnoliopsida" family="Apocynaceae" genus="Eucorymbia" kingdom="Plantae" order="Gentianales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="alba">
<emphasis id="BC8C6A25387BFFC401349B1553D1FA01" bold="true" box="[564,714,1406,1425]" italics="true" pageId="7" pageNumber="8">Eucorymbia alba</emphasis>
Stapf
</taxonomicName>
(two samples) and
<taxonomicName id="49F8CDB4387BFFC402179BF25399FA3D" authority="Woodson" authorityName="Woodson" box="[279,642,1433,1453]" class="Magnoliopsida" family="Apocynaceae" genus="Galactophora" kingdom="Plantae" order="Gentianales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="schomburgkiana">
<emphasis id="BC8C6A25387BFFC402179BF2533EFA3C" bold="true" box="[279,549,1433,1452]" italics="true" pageId="7" pageNumber="8">Galactophora schomburgkiana</emphasis>
Woodson
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(one sample) (
<tableCitation id="C37A838C387BFFC4036C9BDD51AFFA59" box="[108,180,1462,1481]" captionStart="Table 2" captionStartId="5.[100,150,150,166]" captionTargetBox="[116,1426,264,1935]" captionText="Table 2 Samples analyzed on all PREC scans (m/z 120, 138, 156). Samples determined as N: no candidate ions detected, Y (low): low confidence, candidate ions detected only in PREC 120, Y (mod):moderate confidence, candidate ions detected in PREC 120 and PREC 138; Y (low): only candidate ion with mass 432.4–432.5 detected in PREC 120 and PREC 138; Y (high): high confidence, candidate ions detected in PREC 120, 138, and 156. ND: not detected. Vouchers in Table S2. Tribe Species Author sample organ Determination PREC PREC PREC Uncorrected Relative # 120 138 156 Retention Time (min) Vinceae Ochrosia poweri F.M.Bailey 28097 leaf N ND ND ND Rauvolfia balansae (Baill.) Boiteau 28131 leaf N ND ND ND Rauvolfia verticillata (Lour.) Baill. 28099 leaf N ND ND ND Rauvolfia vomitoria Afzel. 28116 leaf N ND ND ND Melodineae Craspidospermum Bojer ex Decne. 630 leaf N ND ND ND verticillatum Wrightieae Wrightia antidysenterica (L.) R. Br. 28422 leaf Y (low) 432.5 a 432.5 ND 11.43 Wrightia dubia (Sims) Spreng. 28418 leaf Y (low) 432.5a 432.5 ND 11.4 Wrightia dubia (Sims) Spreng. 28421 leaf Y (low) 432.5a 432.5 ND 11.39 Wrightia karaketii D.J. Middleton 28451 leaf Y (low) 432.5 a 432.5 ND 11.48 Wrightia tinctoria R.Br. 29370 seed Y (mod) 210.2 ND ND 7.56 328.5 ND ND 9.99 460 ND ND 10.16 300.2 300.2 ND ~10.36 432.4 a 432.4 ND ~10.36 328.5 328.5 ND ~10.36 270.3 270.3 ND ~10.36 352.1 ND ND 11.4 Wrightia tinctoria R.Br. 29371 seed Y (mod) 210.2 ND ND 7.32 328.5 ND ND 9.96 460 ND ND 10.19 300.2 300.2 ND ~10.36 328.5 328.5 ND ~10.36 270.3 270.3 ND ~10.36 432.4 a 432.4 ND ~10.36 352.1 ND ND 11.36 Wrightia versicolor S.T. Blake 28423 leaf Y (mod) 432.4 a 432.4 ND 11.33 300.2 300.2 ND 11.66 Malouetieae Eucorymbia alba Stapf 28111 leaf Y (mod) 238.3 238.3 ND 11.79 354.4 354.4 ND 11.93 396.4 ND ND 12.96 436.5 ND ND 14.72 Eucorymbia alba Stapf 28112 leaf Y (mod) 238.3 238.3 ND 11.798 354.4 354.4 ND 11.932 436.5 ND ND 14.67 Galactophora Woodson 116 leaf Y (mod) 270.4 270.4 ND 9.76 schomburgkiana 238.2 238.2 ND 11.92 Holarrhena pubescens Wall. ex G. Don 231 leaf N ND ND ND Holarrhena pubescens Wall. ex G. Don 233 leaf N ND ND ND Holarrhena pubescens Wall. ex G. Don 234 leaf N ND ND ND Holarrhena pubescens Wall. ex G.Don 29372 seed Y (low) 474.4 ND ND 9.52 498.4 ND ND 9.83 Malouetia calva Markgr. 28965 leaf N ND ND ND Malouetia cestroides Müll.Arg. 28966 leaf N ND ND ND Apocyneae Amphineurion (Roxb.) G. Don 23 leaf Y (low) 320.4 ND ND 15.16 marginatum Amphineurion (Roxb.) G. Don 52 leaf N ND ND ND marginatum Amphineurion (Roxb.) G. Don 270 leaf Y (low) 320.4 ND ND 15.16 marginatum Apocynum cannabinum L. 28918 leaf N ND ND ND Beaumontia murtonii Craib 267 leaf N ND ND ND Beaumontia murtonii Craib 268 leaf N ND ND ND Trachelospermum Nakai 81 leaf N ND ND ND asiaticum Vallaris solanacea (Roth) O. Kuntze 90 leaf N ND ND ND Odontadenieae Pentalinon luteum (L.) B.F.Hansen &amp; 28673 leaf N ND ND ND Wunderlin Pentalinon luteum (L.) B.F.Hansen &amp; 28676 leaf N ND ND ND Wunderlin Mesechiteae Mandevilla boliviensis (Hook. f.) Woodson 76 leaf Y (low) 444.2 ND ND 9.76 458.5 ND ND 9.96 Echiteae Bahiella infundibuliflora J.F.Morales 28143 leaf Y (high) 300.1 300.1 300.1 10.22 Echites panduratus A. DC. 28459 leaf N ND ND ND Echites umbellatus Jacq. 28516 leaf Y (high) 318.4 318.4 318.4 10.43 300.5 300.5 300.5 10.73 456.2 456.2 456.2 11.93 470.5 470.5 470.5 12.57 444.4 444.4 444.4 12.73 458.3 458.3 ND 12.87 (continued on next page)" pageId="7" pageNumber="8">Table 2</tableCitation>
). This is the first report of specialized metabolites from these genera. No PAs were detected in the single sample of
<taxonomicName id="49F8CDB4387BFFC4018A9BBA5090F990" authority="(Mull. Arg.) Woodson" authorityName="Woodson" baseAuthorityName="Mull. Arg." class="Magnoliopsida" family="Apocynaceae" genus="Galactophora" kingdom="Plantae" order="Gentianales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="crassifolia">
<emphasis id="BC8C6A25387BFFC4018A9BBA51A5F990" bold="true" italics="true" pageId="7" pageNumber="8">Galactophora crassifolia</emphasis>
(Müll.Arg.) Woodson
</taxonomicName>
analyzed (
<tableCitation id="C37A838C387BFFC402F39B86535FF991" box="[499,580,1517,1537]" captionStart="Table 2" captionStartId="5.[100,150,150,166]" captionTargetBox="[116,1426,264,1935]" captionText="Table 2 Samples analyzed on all PREC scans (m/z 120, 138, 156). Samples determined as N: no candidate ions detected, Y (low): low confidence, candidate ions detected only in PREC 120, Y (mod):moderate confidence, candidate ions detected in PREC 120 and PREC 138; Y (low): only candidate ion with mass 432.4–432.5 detected in PREC 120 and PREC 138; Y (high): high confidence, candidate ions detected in PREC 120, 138, and 156. ND: not detected. Vouchers in Table S2. Tribe Species Author sample organ Determination PREC PREC PREC Uncorrected Relative # 120 138 156 Retention Time (min) Vinceae Ochrosia poweri F.M.Bailey 28097 leaf N ND ND ND Rauvolfia balansae (Baill.) Boiteau 28131 leaf N ND ND ND Rauvolfia verticillata (Lour.) Baill. 28099 leaf N ND ND ND Rauvolfia vomitoria Afzel. 28116 leaf N ND ND ND Melodineae Craspidospermum Bojer ex Decne. 630 leaf N ND ND ND verticillatum Wrightieae Wrightia antidysenterica (L.) R. Br. 28422 leaf Y (low) 432.5 a 432.5 ND 11.43 Wrightia dubia (Sims) Spreng. 28418 leaf Y (low) 432.5a 432.5 ND 11.4 Wrightia dubia (Sims) Spreng. 28421 leaf Y (low) 432.5a 432.5 ND 11.39 Wrightia karaketii D.J. Middleton 28451 leaf Y (low) 432.5 a 432.5 ND 11.48 Wrightia tinctoria R.Br. 29370 seed Y (mod) 210.2 ND ND 7.56 328.5 ND ND 9.99 460 ND ND 10.16 300.2 300.2 ND ~10.36 432.4 a 432.4 ND ~10.36 328.5 328.5 ND ~10.36 270.3 270.3 ND ~10.36 352.1 ND ND 11.4 Wrightia tinctoria R.Br. 29371 seed Y (mod) 210.2 ND ND 7.32 328.5 ND ND 9.96 460 ND ND 10.19 300.2 300.2 ND ~10.36 328.5 328.5 ND ~10.36 270.3 270.3 ND ~10.36 432.4 a 432.4 ND ~10.36 352.1 ND ND 11.36 Wrightia versicolor S.T. Blake 28423 leaf Y (mod) 432.4 a 432.4 ND 11.33 300.2 300.2 ND 11.66 Malouetieae Eucorymbia alba Stapf 28111 leaf Y (mod) 238.3 238.3 ND 11.79 354.4 354.4 ND 11.93 396.4 ND ND 12.96 436.5 ND ND 14.72 Eucorymbia alba Stapf 28112 leaf Y (mod) 238.3 238.3 ND 11.798 354.4 354.4 ND 11.932 436.5 ND ND 14.67 Galactophora Woodson 116 leaf Y (mod) 270.4 270.4 ND 9.76 schomburgkiana 238.2 238.2 ND 11.92 Holarrhena pubescens Wall. ex G. Don 231 leaf N ND ND ND Holarrhena pubescens Wall. ex G. Don 233 leaf N ND ND ND Holarrhena pubescens Wall. ex G. Don 234 leaf N ND ND ND Holarrhena pubescens Wall. ex G.Don 29372 seed Y (low) 474.4 ND ND 9.52 498.4 ND ND 9.83 Malouetia calva Markgr. 28965 leaf N ND ND ND Malouetia cestroides Müll.Arg. 28966 leaf N ND ND ND Apocyneae Amphineurion (Roxb.) G. Don 23 leaf Y (low) 320.4 ND ND 15.16 marginatum Amphineurion (Roxb.) G. Don 52 leaf N ND ND ND marginatum Amphineurion (Roxb.) G. Don 270 leaf Y (low) 320.4 ND ND 15.16 marginatum Apocynum cannabinum L. 28918 leaf N ND ND ND Beaumontia murtonii Craib 267 leaf N ND ND ND Beaumontia murtonii Craib 268 leaf N ND ND ND Trachelospermum Nakai 81 leaf N ND ND ND asiaticum Vallaris solanacea (Roth) O. Kuntze 90 leaf N ND ND ND Odontadenieae Pentalinon luteum (L.) B.F.Hansen &amp; 28673 leaf N ND ND ND Wunderlin Pentalinon luteum (L.) B.F.Hansen &amp; 28676 leaf N ND ND ND Wunderlin Mesechiteae Mandevilla boliviensis (Hook. f.) Woodson 76 leaf Y (low) 444.2 ND ND 9.76 458.5 ND ND 9.96 Echiteae Bahiella infundibuliflora J.F.Morales 28143 leaf Y (high) 300.1 300.1 300.1 10.22 Echites panduratus A. DC. 28459 leaf N ND ND ND Echites umbellatus Jacq. 28516 leaf Y (high) 318.4 318.4 318.4 10.43 300.5 300.5 300.5 10.73 456.2 456.2 456.2 11.93 470.5 470.5 470.5 12.57 444.4 444.4 444.4 12.73 458.3 458.3 ND 12.87 (continued on next page)" pageId="7" pageNumber="8">Table S2</tableCitation>
), a species that was previously reported as lacking alkaloids (
<bibRefCitation id="EA69CBC6387BFFC402EA986253B5F98C" author="daRocha, A. I. &amp; Luz, A. I. R. &amp; Rodrigues, W. A." box="[490,686,1545,1565]" pageId="7" pageNumber="8" pagination="381 - 387" refId="ref16664" refString="daRocha, A. I., Luz, A. I. R., Rodrigues, W. A., 1982. A presenca de alcaloides´em esp´ecies botˆanicas da Amazonia ˆ. VII - Apocynaceae. Acta Amazonica 12, 381 - 387." type="journal article" year="1982">daRocha et al., 1982</bibRefCitation>
). Evenly massed ions were detected in the
<collectionCode id="E8E92EF2387BFFC402A4984E50C3F9A8" box="[420,472,1573,1592]" pageId="7" pageNumber="8">PREC</collectionCode>
120 (with
<collectionCode id="E8E92EF2387BFFC40141984E5369F9A8" box="[577,626,1573,1592]" country="Australia" httpUri="http://grbio.org/cool/xkx2-bm0k" name="Museum of Central Australia" pageId="7" pageNumber="8" type="Museum">MCA</collectionCode>
) scan in one of two samples of
<taxonomicName id="49F8CDB4387BFFC400CB9FEB540BFE04" authority="King &amp; Gamble" authorityName="King &amp; Gamble" box="[971,1296,384,404]" class="Magnoliopsida" family="Apocynaceae" genus="Holarrhena" kingdom="Plantae" order="Gentianales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="curtisii">
<emphasis id="BC8C6A25387BFFC400CB9FEB556FFE04" bold="true" box="[971,1140,384,404]" italics="true" pageId="7" pageNumber="8">Holarrhena curtisii</emphasis>
King &amp; Gamble
</taxonomicName>
(
<emphasis id="BC8C6A25387BFFC406219FEA545EFE04" bold="true" box="[1313,1349,385,404]" italics="true" pageId="7" pageNumber="8">m/z</emphasis>
284.3, 300.1) (
<tableCitation id="C37A838C387BFFC4003A9FF65292FE20" box="[826,905,413,432]" captionStart="Table 2" captionStartId="5.[100,150,150,166]" captionTargetBox="[116,1426,264,1935]" captionText="Table 2 Samples analyzed on all PREC scans (m/z 120, 138, 156). Samples determined as N: no candidate ions detected, Y (low): low confidence, candidate ions detected only in PREC 120, Y (mod):moderate confidence, candidate ions detected in PREC 120 and PREC 138; Y (low): only candidate ion with mass 432.4–432.5 detected in PREC 120 and PREC 138; Y (high): high confidence, candidate ions detected in PREC 120, 138, and 156. ND: not detected. Vouchers in Table S2. Tribe Species Author sample organ Determination PREC PREC PREC Uncorrected Relative # 120 138 156 Retention Time (min) Vinceae Ochrosia poweri F.M.Bailey 28097 leaf N ND ND ND Rauvolfia balansae (Baill.) Boiteau 28131 leaf N ND ND ND Rauvolfia verticillata (Lour.) Baill. 28099 leaf N ND ND ND Rauvolfia vomitoria Afzel. 28116 leaf N ND ND ND Melodineae Craspidospermum Bojer ex Decne. 630 leaf N ND ND ND verticillatum Wrightieae Wrightia antidysenterica (L.) R. Br. 28422 leaf Y (low) 432.5 a 432.5 ND 11.43 Wrightia dubia (Sims) Spreng. 28418 leaf Y (low) 432.5a 432.5 ND 11.4 Wrightia dubia (Sims) Spreng. 28421 leaf Y (low) 432.5a 432.5 ND 11.39 Wrightia karaketii D.J. Middleton 28451 leaf Y (low) 432.5 a 432.5 ND 11.48 Wrightia tinctoria R.Br. 29370 seed Y (mod) 210.2 ND ND 7.56 328.5 ND ND 9.99 460 ND ND 10.16 300.2 300.2 ND ~10.36 432.4 a 432.4 ND ~10.36 328.5 328.5 ND ~10.36 270.3 270.3 ND ~10.36 352.1 ND ND 11.4 Wrightia tinctoria R.Br. 29371 seed Y (mod) 210.2 ND ND 7.32 328.5 ND ND 9.96 460 ND ND 10.19 300.2 300.2 ND ~10.36 328.5 328.5 ND ~10.36 270.3 270.3 ND ~10.36 432.4 a 432.4 ND ~10.36 352.1 ND ND 11.36 Wrightia versicolor S.T. Blake 28423 leaf Y (mod) 432.4 a 432.4 ND 11.33 300.2 300.2 ND 11.66 Malouetieae Eucorymbia alba Stapf 28111 leaf Y (mod) 238.3 238.3 ND 11.79 354.4 354.4 ND 11.93 396.4 ND ND 12.96 436.5 ND ND 14.72 Eucorymbia alba Stapf 28112 leaf Y (mod) 238.3 238.3 ND 11.798 354.4 354.4 ND 11.932 436.5 ND ND 14.67 Galactophora Woodson 116 leaf Y (mod) 270.4 270.4 ND 9.76 schomburgkiana 238.2 238.2 ND 11.92 Holarrhena pubescens Wall. ex G. Don 231 leaf N ND ND ND Holarrhena pubescens Wall. ex G. Don 233 leaf N ND ND ND Holarrhena pubescens Wall. ex G. Don 234 leaf N ND ND ND Holarrhena pubescens Wall. ex G.Don 29372 seed Y (low) 474.4 ND ND 9.52 498.4 ND ND 9.83 Malouetia calva Markgr. 28965 leaf N ND ND ND Malouetia cestroides Müll.Arg. 28966 leaf N ND ND ND Apocyneae Amphineurion (Roxb.) G. Don 23 leaf Y (low) 320.4 ND ND 15.16 marginatum Amphineurion (Roxb.) G. Don 52 leaf N ND ND ND marginatum Amphineurion (Roxb.) G. Don 270 leaf Y (low) 320.4 ND ND 15.16 marginatum Apocynum cannabinum L. 28918 leaf N ND ND ND Beaumontia murtonii Craib 267 leaf N ND ND ND Beaumontia murtonii Craib 268 leaf N ND ND ND Trachelospermum Nakai 81 leaf N ND ND ND asiaticum Vallaris solanacea (Roth) O. Kuntze 90 leaf N ND ND ND Odontadenieae Pentalinon luteum (L.) B.F.Hansen &amp; 28673 leaf N ND ND ND Wunderlin Pentalinon luteum (L.) B.F.Hansen &amp; 28676 leaf N ND ND ND Wunderlin Mesechiteae Mandevilla boliviensis (Hook. f.) Woodson 76 leaf Y (low) 444.2 ND ND 9.76 458.5 ND ND 9.96 Echiteae Bahiella infundibuliflora J.F.Morales 28143 leaf Y (high) 300.1 300.1 300.1 10.22 Echites panduratus A. DC. 28459 leaf N ND ND ND Echites umbellatus Jacq. 28516 leaf Y (high) 318.4 318.4 318.4 10.43 300.5 300.5 300.5 10.73 456.2 456.2 456.2 11.93 470.5 470.5 470.5 12.57 444.4 444.4 444.4 12.73 458.3 458.3 ND 12.87 (continued on next page)" pageId="7" pageNumber="8">Table S2</tableCitation>
).
<taxonomicName id="49F8CDB4387BFFC4009C9FF75412FE20" authority="(Pierre) Woodson" authorityName="Woodson" baseAuthorityName="Pierre" box="[924,1289,412,432]" class="Magnoliopsida" family="Apocynaceae" genus="Kibatalia" kingdom="Plantae" order="Gentianales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="macrophylla">
<emphasis id="BC8C6A25387BFFC4009C9FF7557BFE3F" bold="true" box="[924,1120,412,431]" italics="true" pageId="7" pageNumber="8">Kibatalia macrophylla</emphasis>
(Pierre) Woodson
</taxonomicName>
(one of two samples) contained three possible PAs in its
<collectionCode id="E8E92EF2387BFFC4076F9FD255B8FE5C" box="[1135,1187,441,460]" pageId="7" pageNumber="8">PREC</collectionCode>
120 (with
<collectionCode id="E8E92EF2387BFFC406069FD2542CFE5C" box="[1286,1335,441,460]" country="Australia" httpUri="http://grbio.org/cool/xkx2-bm0k" name="Museum of Central Australia" pageId="7" pageNumber="8" type="Museum">MCA</collectionCode>
) mass spectrum,
<emphasis id="BC8C6A25387BFFC400329FBF524DFE77" bold="true" box="[818,854,468,487]" italics="true" pageId="7" pageNumber="8">m/z</emphasis>
284.3, 302.4, and 314.0 (
<tableCitation id="C37A838C387BFFC4074E9FBF5584FE77" box="[1102,1183,468,487]" captionStart="Table 2" captionStartId="5.[100,150,150,166]" captionTargetBox="[116,1426,264,1935]" captionText="Table 2 Samples analyzed on all PREC scans (m/z 120, 138, 156). Samples determined as N: no candidate ions detected, Y (low): low confidence, candidate ions detected only in PREC 120, Y (mod):moderate confidence, candidate ions detected in PREC 120 and PREC 138; Y (low): only candidate ion with mass 432.4–432.5 detected in PREC 120 and PREC 138; Y (high): high confidence, candidate ions detected in PREC 120, 138, and 156. ND: not detected. Vouchers in Table S2. Tribe Species Author sample organ Determination PREC PREC PREC Uncorrected Relative # 120 138 156 Retention Time (min) Vinceae Ochrosia poweri F.M.Bailey 28097 leaf N ND ND ND Rauvolfia balansae (Baill.) Boiteau 28131 leaf N ND ND ND Rauvolfia verticillata (Lour.) Baill. 28099 leaf N ND ND ND Rauvolfia vomitoria Afzel. 28116 leaf N ND ND ND Melodineae Craspidospermum Bojer ex Decne. 630 leaf N ND ND ND verticillatum Wrightieae Wrightia antidysenterica (L.) R. Br. 28422 leaf Y (low) 432.5 a 432.5 ND 11.43 Wrightia dubia (Sims) Spreng. 28418 leaf Y (low) 432.5a 432.5 ND 11.4 Wrightia dubia (Sims) Spreng. 28421 leaf Y (low) 432.5a 432.5 ND 11.39 Wrightia karaketii D.J. Middleton 28451 leaf Y (low) 432.5 a 432.5 ND 11.48 Wrightia tinctoria R.Br. 29370 seed Y (mod) 210.2 ND ND 7.56 328.5 ND ND 9.99 460 ND ND 10.16 300.2 300.2 ND ~10.36 432.4 a 432.4 ND ~10.36 328.5 328.5 ND ~10.36 270.3 270.3 ND ~10.36 352.1 ND ND 11.4 Wrightia tinctoria R.Br. 29371 seed Y (mod) 210.2 ND ND 7.32 328.5 ND ND 9.96 460 ND ND 10.19 300.2 300.2 ND ~10.36 328.5 328.5 ND ~10.36 270.3 270.3 ND ~10.36 432.4 a 432.4 ND ~10.36 352.1 ND ND 11.36 Wrightia versicolor S.T. Blake 28423 leaf Y (mod) 432.4 a 432.4 ND 11.33 300.2 300.2 ND 11.66 Malouetieae Eucorymbia alba Stapf 28111 leaf Y (mod) 238.3 238.3 ND 11.79 354.4 354.4 ND 11.93 396.4 ND ND 12.96 436.5 ND ND 14.72 Eucorymbia alba Stapf 28112 leaf Y (mod) 238.3 238.3 ND 11.798 354.4 354.4 ND 11.932 436.5 ND ND 14.67 Galactophora Woodson 116 leaf Y (mod) 270.4 270.4 ND 9.76 schomburgkiana 238.2 238.2 ND 11.92 Holarrhena pubescens Wall. ex G. Don 231 leaf N ND ND ND Holarrhena pubescens Wall. ex G. Don 233 leaf N ND ND ND Holarrhena pubescens Wall. ex G. Don 234 leaf N ND ND ND Holarrhena pubescens Wall. ex G.Don 29372 seed Y (low) 474.4 ND ND 9.52 498.4 ND ND 9.83 Malouetia calva Markgr. 28965 leaf N ND ND ND Malouetia cestroides Müll.Arg. 28966 leaf N ND ND ND Apocyneae Amphineurion (Roxb.) G. Don 23 leaf Y (low) 320.4 ND ND 15.16 marginatum Amphineurion (Roxb.) G. Don 52 leaf N ND ND ND marginatum Amphineurion (Roxb.) G. Don 270 leaf Y (low) 320.4 ND ND 15.16 marginatum Apocynum cannabinum L. 28918 leaf N ND ND ND Beaumontia murtonii Craib 267 leaf N ND ND ND Beaumontia murtonii Craib 268 leaf N ND ND ND Trachelospermum Nakai 81 leaf N ND ND ND asiaticum Vallaris solanacea (Roth) O. Kuntze 90 leaf N ND ND ND Odontadenieae Pentalinon luteum (L.) B.F.Hansen &amp; 28673 leaf N ND ND ND Wunderlin Pentalinon luteum (L.) B.F.Hansen &amp; 28676 leaf N ND ND ND Wunderlin Mesechiteae Mandevilla boliviensis (Hook. f.) Woodson 76 leaf Y (low) 444.2 ND ND 9.76 458.5 ND ND 9.96 Echiteae Bahiella infundibuliflora J.F.Morales 28143 leaf Y (high) 300.1 300.1 300.1 10.22 Echites panduratus A. DC. 28459 leaf N ND ND ND Echites umbellatus Jacq. 28516 leaf Y (high) 318.4 318.4 318.4 10.43 300.5 300.5 300.5 10.73 456.2 456.2 456.2 11.93 470.5 470.5 470.5 12.57 444.4 444.4 444.4 12.73 458.3 458.3 ND 12.87 (continued on next page)" pageId="7" pageNumber="8">Table S2</tableCitation>
).
</paragraph>
<paragraph id="8E47B637387BFFC400519F9B545BFC52" blockId="7.[818,1488,384,962]" pageId="7" pageNumber="8">
The only previous report of PAs in Malouetieae used the Mattocks’ test (
<bibRefCitation id="EA69CBC6387BFFC4005F9C6752F4FD8F" author="Mattocks, A. R." box="[863,1007,524,543]" pageId="7" pageNumber="8" pagination="443 - 447" refId="ref19713" refString="Mattocks, A. R., 1967. Spectrometric determination of unsaturated pyrrolizidine alkaloids. Anal. Chem. 39, 443 - 447." type="journal article" year="1967">Mattocks, 1967</bibRefCitation>
), a colorimetric assay with absorption at
<quantity id="49001BD2387BFFC4066C9C6754AFFDB0" box="[1388,1460,524,544]" metricMagnitude="-7" metricUnit="m" metricValue="5.65" pageId="7" pageNumber="8" unit="nm" value="565.0">565 nm</quantity>
, to detect unsaturated PAs in the seeds of
<taxonomicName id="49F8CDB4387BFFC4079F9C4352CBFDC7" authority="(Arseculeratne et al., 1981)" baseAuthorityName="Arseculeratne" baseAuthorityYear="1981" class="Magnoliopsida" family="Apocynaceae" genus="Holarrhena" kingdom="Plantae" order="Gentianales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="pubescens">
<emphasis id="BC8C6A25387BFFC4079F9C43547AFDAB" bold="true" box="[1183,1377,552,571]" italics="true" pageId="7" pageNumber="8">Holarrhena pubescens</emphasis>
(
<bibRefCitation id="EA69CBC6387BFFC406709C4352DDFDC7" author="Arseculeratne, S. N. &amp; Gunatilaka, A. A. L. &amp; Panabokke, R. G." pageId="7" pageNumber="8" pagination="159 - 177" refId="ref15825" refString="Arseculeratne, S. N., Gunatilaka, A. A. L., Panabokke, R. G., 1981. Studies on medicinal plants of Sri Lanka: occurrence of pyrrolizidine alkaloids and hepatotoxic properties in some traditional medicinal herbs. J. Ethnopharmacol. 4, 159 - 177. https: // doi. org / 10.1016 / 0378 - 8741 (81) 90033 - 7." type="journal article" year="1981">Arseculeratne et al., 1981</bibRefCitation>
)
</taxonomicName>
. In our study, crude extracts of
<taxonomicName id="49F8CDB4387BFFC407EE9C2F5444FDC7" box="[1262,1375,580,599]" class="Magnoliopsida" family="Apocynaceae" genus="Holarrhena" kingdom="Plantae" order="Gentianales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="pubescens">
<emphasis id="BC8C6A25387BFFC407EE9C2F5444FDC7" bold="true" box="[1262,1375,580,599]" italics="true" pageId="7" pageNumber="8">H. pubescens</emphasis>
</taxonomicName>
leaves were evaluated for PAs via LC-MS/MS, with no strong evidence of PAs in the
<collectionCode id="E8E92EF2387BFFC400329C17527DFD1F" box="[818,870,636,655]" pageId="7" pageNumber="8">PREC</collectionCode>
scans. In seeds of
<taxonomicName id="49F8CDB4387BFFC407169C175592FD1E" box="[1046,1161,635,655]" class="Magnoliopsida" family="Apocynaceae" genus="Holarrhena" kingdom="Plantae" order="Gentianales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="pubescens">
<emphasis id="BC8C6A25387BFFC407169C175592FD1E" bold="true" box="[1046,1161,635,655]" italics="true" pageId="7" pageNumber="8">H. pubescens</emphasis>
</taxonomicName>
, two even-massed ions were identified in the
<collectionCode id="E8E92EF2387BFFC400A59CF352C2FD3B" box="[933,985,664,683]" pageId="7" pageNumber="8">PREC</collectionCode>
120 scan only,
<emphasis id="BC8C6A25387BFFC4076D9CF3558AFD3B" bold="true" box="[1133,1169,664,683]" italics="true" pageId="7" pageNumber="8">m/z</emphasis>
476.4 and 498.4 (
<tableCitation id="C37A838C387BFFC4063F9CF3549EFD3B" box="[1343,1413,664,683]" captionStart="Table 2" captionStartId="5.[100,150,150,166]" captionTargetBox="[116,1426,264,1935]" captionText="Table 2 Samples analyzed on all PREC scans (m/z 120, 138, 156). Samples determined as N: no candidate ions detected, Y (low): low confidence, candidate ions detected only in PREC 120, Y (mod):moderate confidence, candidate ions detected in PREC 120 and PREC 138; Y (low): only candidate ion with mass 432.4–432.5 detected in PREC 120 and PREC 138; Y (high): high confidence, candidate ions detected in PREC 120, 138, and 156. ND: not detected. Vouchers in Table S2. Tribe Species Author sample organ Determination PREC PREC PREC Uncorrected Relative # 120 138 156 Retention Time (min) Vinceae Ochrosia poweri F.M.Bailey 28097 leaf N ND ND ND Rauvolfia balansae (Baill.) Boiteau 28131 leaf N ND ND ND Rauvolfia verticillata (Lour.) Baill. 28099 leaf N ND ND ND Rauvolfia vomitoria Afzel. 28116 leaf N ND ND ND Melodineae Craspidospermum Bojer ex Decne. 630 leaf N ND ND ND verticillatum Wrightieae Wrightia antidysenterica (L.) R. Br. 28422 leaf Y (low) 432.5 a 432.5 ND 11.43 Wrightia dubia (Sims) Spreng. 28418 leaf Y (low) 432.5a 432.5 ND 11.4 Wrightia dubia (Sims) Spreng. 28421 leaf Y (low) 432.5a 432.5 ND 11.39 Wrightia karaketii D.J. Middleton 28451 leaf Y (low) 432.5 a 432.5 ND 11.48 Wrightia tinctoria R.Br. 29370 seed Y (mod) 210.2 ND ND 7.56 328.5 ND ND 9.99 460 ND ND 10.16 300.2 300.2 ND ~10.36 432.4 a 432.4 ND ~10.36 328.5 328.5 ND ~10.36 270.3 270.3 ND ~10.36 352.1 ND ND 11.4 Wrightia tinctoria R.Br. 29371 seed Y (mod) 210.2 ND ND 7.32 328.5 ND ND 9.96 460 ND ND 10.19 300.2 300.2 ND ~10.36 328.5 328.5 ND ~10.36 270.3 270.3 ND ~10.36 432.4 a 432.4 ND ~10.36 352.1 ND ND 11.36 Wrightia versicolor S.T. Blake 28423 leaf Y (mod) 432.4 a 432.4 ND 11.33 300.2 300.2 ND 11.66 Malouetieae Eucorymbia alba Stapf 28111 leaf Y (mod) 238.3 238.3 ND 11.79 354.4 354.4 ND 11.93 396.4 ND ND 12.96 436.5 ND ND 14.72 Eucorymbia alba Stapf 28112 leaf Y (mod) 238.3 238.3 ND 11.798 354.4 354.4 ND 11.932 436.5 ND ND 14.67 Galactophora Woodson 116 leaf Y (mod) 270.4 270.4 ND 9.76 schomburgkiana 238.2 238.2 ND 11.92 Holarrhena pubescens Wall. ex G. Don 231 leaf N ND ND ND Holarrhena pubescens Wall. ex G. Don 233 leaf N ND ND ND Holarrhena pubescens Wall. ex G. Don 234 leaf N ND ND ND Holarrhena pubescens Wall. ex G.Don 29372 seed Y (low) 474.4 ND ND 9.52 498.4 ND ND 9.83 Malouetia calva Markgr. 28965 leaf N ND ND ND Malouetia cestroides Müll.Arg. 28966 leaf N ND ND ND Apocyneae Amphineurion (Roxb.) G. Don 23 leaf Y (low) 320.4 ND ND 15.16 marginatum Amphineurion (Roxb.) G. Don 52 leaf N ND ND ND marginatum Amphineurion (Roxb.) G. Don 270 leaf Y (low) 320.4 ND ND 15.16 marginatum Apocynum cannabinum L. 28918 leaf N ND ND ND Beaumontia murtonii Craib 267 leaf N ND ND ND Beaumontia murtonii Craib 268 leaf N ND ND ND Trachelospermum Nakai 81 leaf N ND ND ND asiaticum Vallaris solanacea (Roth) O. Kuntze 90 leaf N ND ND ND Odontadenieae Pentalinon luteum (L.) B.F.Hansen &amp; 28673 leaf N ND ND ND Wunderlin Pentalinon luteum (L.) B.F.Hansen &amp; 28676 leaf N ND ND ND Wunderlin Mesechiteae Mandevilla boliviensis (Hook. f.) Woodson 76 leaf Y (low) 444.2 ND ND 9.76 458.5 ND ND 9.96 Echiteae Bahiella infundibuliflora J.F.Morales 28143 leaf Y (high) 300.1 300.1 300.1 10.22 Echites panduratus A. DC. 28459 leaf N ND ND ND Echites umbellatus Jacq. 28516 leaf Y (high) 318.4 318.4 318.4 10.43 300.5 300.5 300.5 10.73 456.2 456.2 456.2 11.93 470.5 470.5 470.5 12.57 444.4 444.4 444.4 12.73 458.3 458.3 ND 12.87 (continued on next page)" pageId="7" pageNumber="8">Table 2</tableCitation>
). These are considered candidate PAs with low confidence. The specialized metabolites of
<taxonomicName id="49F8CDB4387BFFC400BF9CBB5529FD72" box="[959,1074,719,739]" class="Magnoliopsida" family="Apocynaceae" genus="Holarrhena" kingdom="Plantae" order="Gentianales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="pubescens">
<emphasis id="BC8C6A25387BFFC400BF9CBB5529FD72" bold="true" box="[959,1074,719,739]" italics="true" pageId="7" pageNumber="8">H. pubescens</emphasis>
</taxonomicName>
(syn.
<taxonomicName id="49F8CDB4387BFFC4076D9CBB540BFD72" box="[1133,1296,719,739]" class="Magnoliopsida" family="Apocynaceae" genus="Wrightia" kingdom="Plantae" order="Gentianales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="antidysenterica">
<emphasis id="BC8C6A25387BFFC4076D9CBB540BFD72" bold="true" box="[1133,1296,719,739]" italics="true" pageId="7" pageNumber="8">H. antidysenterica</emphasis>
</taxonomicName>
(
<collectionCode id="E8E92EF2387BFFC4061D9CBB5436FD73" box="[1309,1325,720,739]" country="Netherlands" lsid="urn:lsid:biocol.org:col:15678" name="Nationaal Herbarium Nederland, Leiden University branch" pageId="7" pageNumber="8" type="Herbarium">L</collectionCode>
.) Wall. ex A.DC.,
<taxonomicName id="49F8CDB4387BFFC400329C87557DFD6E" authority="T. Durand &amp; Schinz" authorityName="T. Durand &amp; Schinz" box="[818,1126,747,767]" class="Magnoliopsida" family="Apocynaceae" genus="Holarrhena" kingdom="Plantae" order="Gentianales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="floribunda">
<emphasis id="BC8C6A25387BFFC400329C8752B1FD6E" bold="true" box="[818,938,747,767]" italics="true" pageId="7" pageNumber="8">H. floribunda</emphasis>
T.Durand &amp; Schinz
</taxonomicName>
) are well studied, with steroidal alkaloids and glycosides of primary interest for their potential bioactivity (
<bibRefCitation id="EA69CBC6387BFFC4003A9D485501FCA6" author="Kumar, N. &amp; Singh, B. &amp; Bhandari, P. &amp; Gupta, A. P. &amp; Kaul, V. K." box="[826,1050,803,822]" pageId="7" pageNumber="8" pagination="912 - 914" refId="ref18811" refString="Kumar, N., Singh, B., Bhandari, P., Gupta, A. P., Kaul, V. K., 2007. Steroidal alkaloids from Holarrhena antidysenterica (L.) Wall. Chem. Pharm. Bull. 55, 912 - 914. https: // doi. org / 10.1248 / cpb. 55.912." type="journal article" year="2007">Kumar et al., 2007</bibRefCitation>
;
<bibRefCitation id="EA69CBC6387BFFC407379D485416FCA6" author="Sinha, S. &amp; Sharma, A. &amp; Reddy, P. H. &amp; Rathi, B. &amp; Prasad, N. V. S. R. K. &amp; Vashishtha, A." box="[1079,1293,803,822]" pageId="7" pageNumber="8" pagination="488 - 492" refId="ref20852" refString="Sinha, S., Sharma, A., Reddy, P. H., Rathi, B., Prasad, N. V. S. R. K., Vashishtha, A., 2013. Evaluation of phytochemical and pharmacological aspects of Holarrhena antidysenterica (Wall.): a comprehensive review. J. Pharm. Res. 6, 488 - 492. https: // doi. org / 10.1016 / j. jopr. 2013.04.004." type="journal article" year="2013">Sinha et al., 2013</bibRefCitation>
). Three steroidal amino-glycosides previously reported from
<taxonomicName id="49F8CDB4387BFFC407C99D545427FCC2" box="[1225,1340,831,850]" class="Magnoliopsida" family="Apocynaceae" genus="Holarrhena" kingdom="Plantae" order="Gentianales" pageId="7" pageNumber="8" phylum="Tracheophyta" rank="species" species="pubescens">
<emphasis id="BC8C6A25387BFFC407C99D545427FCC2" bold="true" box="[1225,1340,831,850]" italics="true" pageId="7" pageNumber="8">H. pubescens</emphasis>
</taxonomicName>
(holantosine B, D, and F, MW
<emphasis id="BC8C6A25387BFFC400B39D3052D8FCFE" bold="true" box="[947,963,859,878]" pageId="7" pageNumber="8">=</emphasis>
475.3 Da) correspond in mass to one of the ions detected in
<collectionCode id="E8E92EF2387BFFC4004B9D1C5264FC1A" box="[843,895,887,906]" pageId="7" pageNumber="8">PREC</collectionCode>
120 (
<bibRefCitation id="EA69CBC6387BFFC400B99D1C5571FC1A" author="Afendi, F. M. &amp; Okada, T. &amp; Yamazaki, M. &amp; Hirai-Morita, A. &amp; Nakamura, Y. &amp; Nakamura, K. &amp; Ikeda, S. &amp; Takahashi, H. &amp; Altaf-Ul-Amin, M. &amp; Darusman, L. K. &amp; Saito, K. &amp; Kanaya, S." box="[953,1130,887,906]" pageId="7" pageNumber="8" pagination="1" refId="ref15644" refString="Afendi, F. M., Okada, T., Yamazaki, M., Hirai-Morita, A., Nakamura, Y., Nakamura, K., Ikeda, S., Takahashi, H., Altaf-Ul-Amin, M., Darusman, L. K., Saito, K., Kanaya, S., 2011. KNApSAcK family databases: integrated metabolite - plant species databases for multifaceted plant research. Plant Cell Physiol. 53, e 1. https: // doi. org / 10.1093 / pcp / pcr 165 queried 16 July 2020." type="journal article" year="2011">Afendi et al., 2011</bibRefCitation>
;
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). Analysis of standards and/or alternative analytical techniques would be required for absolute identification of the compounds detected here.
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</subSubSection>
</treatment>
</document>
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