135 lines
16 KiB
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135 lines
16 KiB
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<mods:title id="AE2ACF69EA1AC1228950DDE872BB47C0">Chemotaxonomic investigation of Apocynaceae for retronecine-type pyrrolizidine alkaloids using HPLC-MS / MS</mods:title>
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<mods:namePart id="5B8791683F3C46C579451B888A4D7D5D">Barny, Lea A.</mods:namePart>
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1.1.
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<taxonomicName id="49F8CDB4387DFFC203959C385012FDF6" ID-CoL="6L2" ID-ENA="4056" authorityName="Juss." box="[149,265,595,614]" class="Magnoliopsida" family="Apocynaceae" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="family">Apocynaceae</taxonomicName>
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<taxonomicName id="49F8CDB4387DFFC203849CE051E4FD0E" box="[132,255,651,670]" class="Magnoliopsida" family="Apocynaceae" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="family">Apocynaceae</taxonomicName>
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is the tenth largest angiosperm plant family, with ca. 5300 species classified in 378 genera (
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<bibRefCitation id="EA69CBC6387DFFC202C49CCC5362FD2A" author="Endress, M. E. & Meve, U. & Middleton, D. J. & Liede-Schumann, S." box="[452,633,679,698]" pageId="1" pageNumber="2" pagination="207 - 411" refId="ref17110" refString="Endress, M. E., Meve, U., Middleton, D. J., Liede-Schumann, S., 2018. Apocynaceae. In: Kadereit, J., Bittrich, V. (Eds.), Flowering Plants. Eudicots. Apiales, Gentianales (Except Rubiaceae), vol. 15. Springer International Publishing, pp. 207 - 411." type="book chapter" year="2018">Endress et al., 2018</bibRefCitation>
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). The family is of particular importance in natural products research because of the occurrence of multiple medicinally important species and compounds including monoterpenoid indole alkaloids, exemplified by the chemotherapy drugs vincristine and vinblastine from
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<taxonomicName id="49F8CDB4387DFFC201249D7D53C1FCBA" box="[548,730,790,810]" class="Magnoliopsida" family="Apocynaceae" genus="Catharanthus" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="roseus">
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<emphasis id="BC8C6A25387DFFC201249D7D53C1FCBA" bold="true" box="[548,730,790,810]" italics="true" pageId="1" pageNumber="2">Catharanthus roseus</emphasis>
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</taxonomicName>
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(L.) G.Don (
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<bibRefCitation id="EA69CBC6387DFFC203AD9D59504DFCD6" author="Aslam, J. & Khan, S. & Siddiqui, Z. & Zohra, F. & Mehpara, M. & Bhat, M. & Nasim, S. & Ilah, A. & Ahmad, I. & Khan, S. & Mujib, A. & Sharma, M." box="[173,342,818,838]" pageId="1" pageNumber="2" pagination="1 - 16" refId="ref15900" refString="Aslam, J., Khan, S., Siddiqui, Z., Zohra, F., Mehpara, M., Bhat, M., Nasim, S., Ilah, A., Ahmad, I., Khan, S., Mujib, A., Sharma, M., 2010. Catharanthus roseus (L.) G. Don. An important drug: its applications and production. Pharmacie Globale: International Journal of Comprehensive Pharmacy 4, 1 - 16." type="journal article" year="2010">Aslam et al., 2010</bibRefCitation>
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). The expense and difficulty of deriving these valuable molecules from natural sources has motivated the complete biochemical elucidation of their biosynthetic pathway as a steppingstone to its genetic engineering (
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<bibRefCitation id="EA69CBC6387DFFC202909DED5321FC09" author="Caputi, L. & Franke, J. & Farrow, S. C. & Chung, K. & Payne, R. M. E. & Nguyen, T. - D. & Dang, T. - T. T. & Soares Teto Carqueijeiro, I. & Koudounas, K. & Bernonville, T. & Ameyaw, B. & Jones, D. M. & Vieira, I. J. C. & Courdavault, V. & Connor, S. E." box="[400,570,902,921]" pageId="1" pageNumber="2" pagination="1235 - 1239" refId="ref16285" refString="Caputi, L., Franke, J., Farrow, S. C., Chung, K., Payne, R. M. E., Nguyen, T. - D., Dang, T. - T. T., Soares Teto Carqueijeiro, I., Koudounas, K., Duge´de Bernonville, T., Ameyaw, B., Jones, D. M., Vieira, I. J. C., Courdavault, V., O' Connor, S. E., 2018. Missing enzymes in the biosynthesis of the anticancer drug vinblastine in Madagascar periwinkle. Science 360, 1235 - 1239. https: // doi. org / 10.1126 / science. aat 4100." type="journal article" year="2018">Caputi et al., 2018</bibRefCitation>
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;
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<bibRefCitation id="EA69CBC6387DFFC201449DED53D7FC09" author="Qu, Y. & Safonova, O. & De Luca, V." box="[580,716,902,921]" pageId="1" pageNumber="2" pagination="257 - 266" refId="ref20210" refString="Qu, Y., Safonova, O., De Luca, V., 2019. Completion of the canonical pathway for assembly of anticancer drugs vincristine / vinblastine in Catharanthus roseus. Plant J. 97, 257 - 266. https: // doi. org / 10.1111 / tpj. 14111." type="journal article" year="2019">Qu et al., 2019</bibRefCitation>
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). The genus
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<taxonomicName id="49F8CDB4387DFFC203A19DC951E9FC25" box="[161,242,930,949]" class="Magnoliopsida" family="Apocynaceae" genus="Asclepias" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="genus">
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<emphasis id="BC8C6A25387DFFC203A19DC951E9FC25" bold="true" box="[161,242,930,949]" italics="true" pageId="1" pageNumber="2">Asclepias</emphasis>
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</taxonomicName>
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L. and its specialized herbivores are a model system in chemical ecology and evolution of reciprocal adaptations between plants and herbivores, with a particular focus on cardenolides (
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<bibRefCitation id="EA69CBC6387DFFC201B39DB151C5FB99" author="Agrawal, A. A. & Petschenka, G. & Bingham, R. A. & Weber, M. G. & Rasmann, S." pageId="1" pageNumber="2" pagination="28 - 45" refId="ref15752" refString="Agrawal, A. A., Petschenka, G., Bingham, R. A., Weber, M. G., Rasmann, S., 2012. Toxic cardenolides: chemical ecology and coevolution of specialized plant - herbivore interactions. New Phytol. 194, 28 - 45. https: // doi. org / 10.1111 / j. 1469 - 8137.2011.04049. x." type="journal article" year="2012">Agrawal et al., 2012</bibRefCitation>
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). Pyrrolizidine alkaloids (PAs) are also implicated in co-evolution between
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<taxonomicName id="49F8CDB4387DFFC202379A7950A9FBB5" box="[311,434,1042,1061]" class="Magnoliopsida" family="Apocynaceae" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="family">Apocynaceae</taxonomicName>
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and one of their specialized herbivore lineages,
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<taxonomicName id="49F8CDB4387DFFC203F39A465078FBD0" authorityName="Linnaeus" authorityYear="1758" box="[243,355,1069,1088]" class="Magnoliopsida" kingdom="Plantae" order="Lepidoptera" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="order">Lepidoptera</taxonomicName>
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subfamily
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<taxonomicName id="49F8CDB4387DFFC202D29A465331FBD0" authorityName="Boisduval" authorityYear="1833" box="[466,554,1069,1088]" class="Insecta" family="Danainae" higherTaxonomySource="GBIF" kingdom="Animalia" order="Lepidoptera" pageId="1" pageNumber="2" phylum="Arthropoda" rank="family">Danainae</taxonomicName>
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(milkweed and clearwing butterflies). Evolution of the first gene of the PA biosynthetic pathway, homospermidine synthase (
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<emphasis id="BC8C6A25387DFFC202D39A0E50F5FBE8" bold="true" box="[467,494,1125,1144]" italics="true" pageId="1" pageNumber="2">hss</emphasis>
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), has been elucidated (
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<bibRefCitation id="EA69CBC6387DFFC201DE9A0E5003FB04" author="Livshultz, T. & Kaltenegger, E. & Straub, S. C. K. & Weitemier, K. & Hirsch, E. & Koval, K. & Mema, L. & Liston, A." pageId="1" pageNumber="2" pagination="762 - 773" refId="ref19392" refString="Livshultz, T., Kaltenegger, E., Straub, S. C. K., Weitemier, K., Hirsch, E., Koval, K., Mema, L., Liston, A., 2018 a. Evolution of pyrrolizidine alkaloid biosynthesis in Apocynaceae: revisiting the defence de-escalation hypothesis. New Phytol. 218, 762 - 773. https: // doi. org / 10.1111 / nph. 15061." type="journal article" year="2018">Livshultz et al., 2018a</bibRefCitation>
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). Researchers have detected phylogenetic signals in the distribution of all of these compounds and others, including steroidal and phenanthroindolizidine alkaloids and steroidal glycosides, in
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<taxonomicName id="49F8CDB4387DFFC203649ABE50A8FB78" authority="(Endress et al., 2018)" baseAuthorityName="Endress" baseAuthorityYear="2018" box="[100,435,1237,1256]" class="Magnoliopsida" family="Apocynaceae" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="family">
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Apocynaceae (
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<bibRefCitation id="EA69CBC6387DFFC203EF9ABE50B1FB78" author="Endress, M. E. & Meve, U. & Middleton, D. J. & Liede-Schumann, S." box="[239,426,1237,1256]" pageId="1" pageNumber="2" pagination="207 - 411" refId="ref17110" refString="Endress, M. E., Meve, U., Middleton, D. J., Liede-Schumann, S., 2018. Apocynaceae. In: Kadereit, J., Bittrich, V. (Eds.), Flowering Plants. Eudicots. Apiales, Gentianales (Except Rubiaceae), vol. 15. Springer International Publishing, pp. 207 - 411." type="book chapter" year="2018">Endress et al., 2018</bibRefCitation>
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)
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</taxonomicName>
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, but knowledge of their taxonomic distribution still lags progress on the phylogeny of the family (
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<bibRefCitation id="EA69CBC6387DFFC201B29A9A51CBFAB0" author="Fishbein, M. & Livshultz, T. & Straub, S. C. K. & Simtoes, A. O. & Boutte, J. & McDonnell, A. & Foote, A." pageId="1" pageNumber="2" pagination="1 - 19" refId="ref17334" refString="Fishbein, M., Livshultz, T., Straub, S. C. K., Simtoes, A. O., Boutte, J., McDonnell, A., Foote, A., 2018. Evolution on the backbone: Apocynaceae phylogenomics and new perspectives on growth forms, flowers, and fruits. Am. J. Bot. 105, 1 - 19. https: // doi. org / 10.1002 / ajb 2.1067." type="journal article" year="2018">Fishbein et al., 2018</bibRefCitation>
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).
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</paragraph>
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