497 lines
61 KiB
XML
497 lines
61 KiB
XML
<document id="1B572C66F1DA1ADD37194F0C0EB8B94F" ID-DOI="10.1016/j.phytochem.2019.112055" ID-ISSN="1873-3700" ID-Zenodo-Dep="10483285" IM.bibliography_approvedBy="valdenar" IM.illustrations_approvedBy="valdenar" IM.materialsCitations_approvedBy="felipe" IM.metadata_approvedBy="felipe" IM.tables_approvedBy="valdenar" IM.taxonomicNames_approvedBy="felipe" IM.treatments_approvedBy="valdenar" checkinTime="1704934860277" checkinUser="felipe" docAuthor="Hulcová, Daniela, Maříková, Jana, Korábečný, Jan, Hošťálková, Anna, Jun, Daniel, Kuneš, Jiří, Chlebek, Jakub, Opletal, Lubomír, Simone, Angela De, Nováková, Lucie, Andrisano, Vincenza, Růžička, Aleš & Cahlíková, Lucie" docDate="2019" docId="5C7FA13EFFF06B52FCF89AC0E57DF804" docLanguage="en" docName="Phytochemistry.165.112055.pdf" docOrigin="Phytochemistry 165" docSource="http://dx.doi.org/10.1016/j.phytochem.2019.112055" docStyle="DocumentStyle:9E596C34F4E94307D29315B03ACE1007.6:Phytochemistry.2014-2019.journal_article" docStyleId="9E596C34F4E94307D29315B03ACE1007" docStyleName="Phytochemistry.2014-2019.journal_article" docStyleVersion="6" docTitle="Amaryllidaceae" docType="treatment" docVersion="4" lastPageNumber="3" masterDocId="A046D946FFF16B51FFCA9950E770FFC3" masterDocTitle="Amaryllidaceae alkaloids from Narcissus pseudonarcissus L. cv. Dutch Master as potential drugs in treatment of Alzheimer's disease" masterLastPageNumber="9" masterPageNumber="1" pageNumber="2" updateTime="1706542871975" updateUser="valdenar">
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<mods:title id="280FB14F478764C0ADB8039655F43F92">Amaryllidaceae alkaloids from Narcissus pseudonarcissus L. cv. Dutch Master as potential drugs in treatment of Alzheimer's disease</mods:title>
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<mods:namePart id="9959011FD0774C94AD982B3349424589">Hulcová, Daniela</mods:namePart>
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<mods:affiliation id="0F40B9BCC7211F3CC1C9C6DDD7493500">∗ & ADINACO Research Group, Department of Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech & Department of Pharmacognosy, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic</mods:affiliation>
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<mods:namePart id="C1EA69BBEF4CC7B1B6B45B9788D5183F">Nováková, Lucie</mods:namePart>
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<mods:namePart id="E1559155D5C5D5799071ED6BD9EC203F">Andrisano, Vincenza</mods:namePart>
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<mods:title id="5908D9199C345A5A0F07262A77F79055">Phytochemistry</mods:title>
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<mods:date id="5F28DAE94F5DCDE4730FDD6DE4078F5D">2019</mods:date>
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<mods:number id="D44C8C2CE7F7333113B5393F604794D4">2019-09-30</mods:number>
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<mods:number id="9E6215747EE1EE61AE333219114D491C">165</mods:number>
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<mods:identifier id="4F6F0903184B8346F9B018C9FEC772E6" type="DOI">10.1016/j.phytochem.2019.112055</mods:identifier>
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<treatment id="5C7FA13EFFF06B52FCF89AC0E57DF804" LSID="urn:lsid:plazi:treatment:5C7FA13EFFF06B52FCF89AC0E57DF804" httpUri="http://treatment.plazi.org/id/5C7FA13EFFF06B52FCF89AC0E57DF804" lastPageId="3" lastPageNumber="3" pageId="1" pageNumber="2">
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<subSubSection id="9CCC43A3FFF06B50FCF89AC0E2EAFC60" box="[818,1434,912,931]" pageId="1" pageNumber="2" type="nomenclature">
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2.1. Isolation and structural elucidation of
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<taxonomicName id="13D66BABFFF06B50FB729AC0E232FC60" ID-CoL="694" ID-ENA="4668" box="[1208,1346,912,931]" class="Liliopsida" family="Amaryllidaceae" kingdom="Plantae" order="Asparagales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="family">Amaryllidaceae</taxonomicName>
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alkaloids
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Twenty-one known
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alkaloids (1–5, 7–22), and one new alkaloid (6) were isolated from fresh bulbs of
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<taxonomicName id="13D66BABFFF06B50FAE49AB4E4F2FBD0" class="Liliopsida" family="Amaryllidaceae" genus="Narcissus" kingdom="Plantae" order="Asparagales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="pseudonarcissus">
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<emphasis id="E6A2CC3AFFF06B50FAE49AB4E4F2FBD0" bold="true" italics="true" pageId="1" pageNumber="2">Narcissus pseudonarcissus</emphasis>
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cv. Dutch Master (
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<taxonomicName id="13D66BABFFF06B50FB829D50E3AEFBD0" box="[1096,1246,1024,1043]" class="Liliopsida" family="Amaryllidaceae" kingdom="Plantae" order="Asparagales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="family">Amaryllidaceae</taxonomicName>
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) by common chromatographic methods. The compounds were identified by MS, ESI-HRMS, 1D and 2D NMR spectroscopic analyses and by comparison of the obtained data with the literature for homolycorine (1) (
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<bibRefCitation id="B0476DD9FFF06B50FACF9D04E2B1FBA4" author="Huang, S. - D. & Zhang, Y. & He, H. - P. & Li, S. - F. & Tang, G. - H. & Chen, D. - Z. & Cao, M. - M. & Di, Y. - T. & Hao, X. - J." box="[1285,1473,1107,1127]" pageId="1" pageNumber="2" pagination="406 - 410" refId="ref12112" refString="Huang, S. - D., Zhang, Y., He, H. - P., Li, S. - F., Tang, G. - H., Chen, D. - Z., Cao, M. - M., Di, Y. - T., Hao, X. - J., 2013. A new Amaryllidaceae alkaloid from the bulbs of Lycoris radiata. Chin. J. Nat. Med. 11, 406 - 410. https: // doi. org / 10.1016 / S 1875 - 5364 (13) 60060 - 6." type="journal article" year="2013">Huang et al., 2013</bibRefCitation>
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), masonine (2) (
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<bibRefCitation id="B0476DD9FFF06B50FC0A9D3FE317FB40" author="Pigni, N. B. & Rios-Ruiz, S. & Martinez-Frances, V. & Nair, J. J. & Viladomat, F. & Codina, C. & Bastida, J." box="[960,1127,1135,1155]" pageId="1" pageNumber="2" pagination="1643 - 1647" refId="ref13622" refString="Pigni, N. B., Rios-Ruiz, S., Martinez-Frances, V., Nair, J. J., Viladomat, F., Codina, C., Bastida, J., 2012. Alkaloids from Narcissus serotinus. J. Nat. Prod. 75, 1643 - 1647. https: // doi. org / 10.1021 / np 3003595." type="journal article" year="2012">Pigni et al., 2012</bibRefCitation>
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), seco-isopowellaminone (3) (
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<bibRefCitation id="B0476DD9FFF06B50FA469D20E4DEFB5D" author="Kogure, N. & Katsuta, N. & Kitajima, M. & Takayama, H." pageId="1" pageNumber="2" pagination="1545 - 1548" refId="ref12699" refString="Kogure, N., Katsuta, N., Kitajima, M., Takayama, H., 2011. Two new alkaloids from Crinum asiaticum var. sinicum. Chem. Pharm. Bull. 59, 1545 - 1548. https: // doi. org / 10.1248 / cpb. 59.1545." type="journal article" year="2011">Kogure et al., 2011</bibRefCitation>
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),
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<emphasis id="E6A2CC3AFFF06B50FC019DDBE4AAFB5D" bold="true" box="[971,986,1163,1182]" italics="true" pageId="1" pageNumber="2">O</emphasis>
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-ethyllycorenine (4) (
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<bibRefCitation id="B0476DD9FFF06B50FB7F9DDCE20FFB5D" author="Huang, S. - D. & Zhang, Y. & He, H. - P. & Li, S. - F. & Tang, G. - H. & Chen, D. - Z. & Cao, M. - M. & Di, Y. - T. & Hao, X. - J." box="[1205,1407,1163,1183]" pageId="1" pageNumber="2" pagination="406 - 410" refId="ref12112" refString="Huang, S. - D., Zhang, Y., He, H. - P., Li, S. - F., Tang, G. - H., Chen, D. - Z., Cao, M. - M., Di, Y. - T., Hao, X. - J., 2013. A new Amaryllidaceae alkaloid from the bulbs of Lycoris radiata. Chin. J. Nat. Med. 11, 406 - 410. https: // doi. org / 10.1016 / S 1875 - 5364 (13) 60060 - 6." type="journal article" year="2013">Huang et al., 2013</bibRefCitation>
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),
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||
<emphasis id="E6A2CC3AFFF06B50FA569DDCE2DBFB5C" bold="true" box="[1436,1451,1164,1183]" italics="true" pageId="1" pageNumber="2">N</emphasis>
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-demethylmasonine (5) (
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<bibRefCitation id="B0476DD9FFF06B50FBCF9DF7E387FB79" author="Kreh, M. & Matusch, R." box="[1029,1271,1191,1210]" pageId="1" pageNumber="2" pagination="1533 - 1535" refId="ref12756" refString="Kreh, M., Matusch, R., 1995. O-Methyloduline and N-demethylmasonine, alkaloids from Narcissus pseudonarcissus. Phytochemistry 38, 1533 - 1535. https: // doi. org / 10. 1016 / 0031 - 9422 (94) 00827 - G." type="journal article" year="1995">Kreh and Matusch, 1995</bibRefCitation>
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),
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||
<emphasis id="E6A2CC3AFFF06B50FAC59DF7E26EFB79" bold="true" box="[1295,1310,1191,1210]" italics="true" pageId="1" pageNumber="2">O</emphasis>
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-acetylpluviine (7) (
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<bibRefCitation id="B0476DD9FFF06B50FCF09D93E482FB15" author="Harken, R. D. & Christensen, C. P. & Wildman, W. C." box="[826,1010,1219,1239]" pageId="1" pageNumber="2" pagination="2450 - 2454" refId="ref11859" refString="Harken, R. D., Christensen, C. P., Wildman, W. C., 1976. Interconversions in the pluviinelycorenine series. J. Org. Chem. 41, 2450 - 2454. https: // doi. org / 10.1021 / jo 00876 a 021." type="journal article" year="1976">Harken et al., 1976</bibRefCitation>
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), tazettine (8) (
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<bibRefCitation id="B0476DD9FFF06B50FB419D93E244FB15" author="Pham, L. H. & Grundemann, E. & Wagner, J. & Bartoszek, M. & Dopke, W." box="[1163,1332,1219,1239]" pageId="1" pageNumber="2" pagination="327 - 332" refId="ref13481" refString="Pham, L. H., Grundemann, E., Wagner, J., Bartoszek, M., Dopke, W., 1999. Two novel Amaryllidaceae alkaloids from Hippeastrum equestre Herb.: 3 - O-demethyltazettine and egonine. Phytochemistry 51, 327 - 332. https: // doi. org / 10.1016 / S 0031 - 9422 (98) 00743 - 2." type="journal article" year="1999">Pham et al., 1999</bibRefCitation>
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||
), galanthine (9) (
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||
<bibRefCitation id="B0476DD9FFF06B50FCF09D8FE498FB31" author="Kihara, M. & Xu, L. & Konishi, K. & Kida, K. & Nagao, Y. & Kobayashi, S. & Shingu, T." box="[826,1000,1247,1266]" pageId="1" pageNumber="2" pagination="289 - 292" refId="ref12546" refString="Kihara, M., Xu, L., Konishi, K., Kida, K., Nagao, Y., Kobayashi, S., Shingu, T., 1994. Isolation and structure elucidation of a novel alkaloid, incartine, a supposed biosynthetic intermediate, from flowers of lycoris incarnata. Chem. Pharm. Bull. 42, 289 - 292. https: // doi. org / 10.1248 / cpb. 42.289." type="journal article" year="1994">Kihara et al., 1994</bibRefCitation>
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), galanthamine (10) (
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<bibRefCitation id="B0476DD9FFF06B50FB729D8FE228FB31" author="Chen, J. - Q. & Xie, J. - H. & Bao, D. - H. & Liu, S. & Zhou, Q. - L." box="[1208,1368,1247,1266]" pageId="1" pageNumber="2" pagination="2714 - 2717" refId="ref10932" refString="Chen, J. - Q., Xie, J. - H., Bao, D. - H., Liu, S., Zhou, Q. - L., 2012. Total synthesis of (-) - Galanthamine and (-) - Lycoramine via catalytic asymmetric hydrogenation and intramolecular reductive heck cyclization. Org. Lett. 14, 2714 - 2717. https: // doi. org / 10.1021 / ol 300913 g." type="journal article" year="2012">Chen et al., 2012</bibRefCitation>
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), narwedine (11) (
|
||
<bibRefCitation id="B0476DD9FFF06B50FCA29DABE354FACD" author="Jegorov, A. & Buchta, M. & Sedmera, P. & Kuzma, M. & Havlicek, V." box="[872,1060,1275,1294]" pageId="1" pageNumber="2" pagination="544 - 548" refId="ref12486" refString="Jegorov, A., Buchta, M., Sedmera, P., Kuzma, M., Havlicek, V., 2006. Accurate product ion mass spectra of galanthamine derivatives. J. Mass Spectrom. 41, 544 - 548. https: // doi. org / 10.1002 / jms. 1015." type="journal article" year="2006">Jegorov et al., 2006</bibRefCitation>
|
||
), caranine (12) (
|
||
<bibRefCitation id="B0476DD9FFF06B50FB0F9DABE2B1FACD" author="Lamoral-Theys, D. & Andolfi, A. & Van Goietsenoven, G. & Cimmino, A. & Le Calve, B. & Wauthoz, N. & Megalizzi, V. & Gras, T. & Bruyere, C. & Dubois, J. & Mathieu, V. & Kornienko, A. & Kiss, R. & Evidente, A." box="[1221,1473,1275,1294]" pageId="1" pageNumber="2" pagination="6244 - 6256" refId="ref12865" refString="Lamoral-Theys, D., Andolfi, A., Van Goietsenoven, G., Cimmino, A., Le Calve, B., Wauthoz, N., Megalizzi, V., Gras, T., Bruyere, C., Dubois, J., Mathieu, V., Kornienko, A., Kiss, R., Evidente, A., 2009. Lycorine, the main phenanthridine Amaryllidaceae alkaloid, exhibits significant antitumor activity in cancer cells that display resistance to proapoptotic stimuli: An investigation of structure-activity relationship and mechanistic insight. J. Med. Chem. 52, 6244 - 6256. https: // doi. org / 10.1021 / jm 901031 h." type="journal article" year="2009">Lamoral-Theys et al., 2009</bibRefCitation>
|
||
), lycoraminone (13) (
|
||
<bibRefCitation id="B0476DD9FFF06B50FC3D9C47E3E5FAE9" author="Lee, T. B. K. & Goehring, K. E. & Ma, Z." box="[1015,1173,1303,1322]" pageId="1" pageNumber="2" pagination="4535 - 4538" refId="ref12995" refString="Lee, T. B. K., Goehring, K. E., Ma, Z., 1998. One-step conversion of galanthamine to Lycoraminone: a novel hydride-transfer reaction. J. Org. Chem. 63, 4535 - 4538. https: // doi. org / 10.1021 / jo 980271 g." type="journal article" year="1998">Lee et al., 1998</bibRefCitation>
|
||
), lycoramine (14) (
|
||
<bibRefCitation id="B0476DD9FFF06B50FA919C47E412FA85" author="Chen, J. - Q. & Xie, J. - H. & Bao, D. - H. & Liu, S. & Zhou, Q. - L." pageId="1" pageNumber="2" pagination="2714 - 2717" refId="ref10932" refString="Chen, J. - Q., Xie, J. - H., Bao, D. - H., Liu, S., Zhou, Q. - L., 2012. Total synthesis of (-) - Galanthamine and (-) - Lycoramine via catalytic asymmetric hydrogenation and intramolecular reductive heck cyclization. Org. Lett. 14, 2714 - 2717. https: // doi. org / 10.1021 / ol 300913 g." type="journal article" year="2012">Chen et al., 2012</bibRefCitation>
|
||
),
|
||
<emphasis id="E6A2CC3AFFF06B50FCBC9C63E4F5FA85" bold="true" box="[886,901,1331,1350]" italics="true" pageId="1" pageNumber="2">O</emphasis>
|
||
-methyllycorenine (15) (
|
||
<bibRefCitation id="B0476DD9FFF06B50FBA79C63E38DFA85" author="Liu, Z. - M. & Huang, X. - Y. & Cui, M. - R. & Zhang, X. - D. & Chen, Z. & Yang, B. - S. & Zhao, X. - K." box="[1133,1277,1331,1350]" pageId="1" pageNumber="2" pagination="188 - 193" refId="ref13055" refString="Liu, Z. - M., Huang, X. - Y., Cui, M. - R., Zhang, X. - D., Chen, Z., Yang, B. - S., Zhao, X. - K., 2015. Amaryllidaceae alkaloids from the bulbs of Lycoris radiata with cytotoxic and antiinflammatory activities. Fitoterapia 101, 188 - 193. https: // doi. org / 10.1016 / j. fitote. 2015.01. 003." type="journal article" year="2015">Liu et al., 2015</bibRefCitation>
|
||
), lycorenine (16) (
|
||
<bibRefCitation id="B0476DD9FFF06B50FA7B9C63E4D0FAA1" author="Liu, Z. - M. & Huang, X. - Y. & Cui, M. - R. & Zhang, X. - D. & Chen, Z. & Yang, B. - S. & Zhao, X. - K." pageId="1" pageNumber="2" pagination="188 - 193" refId="ref13055" refString="Liu, Z. - M., Huang, X. - Y., Cui, M. - R., Zhang, X. - D., Chen, Z., Yang, B. - S., Zhao, X. - K., 2015. Amaryllidaceae alkaloids from the bulbs of Lycoris radiata with cytotoxic and antiinflammatory activities. Fitoterapia 101, 188 - 193. https: // doi. org / 10.1016 / j. fitote. 2015.01. 003." type="journal article" year="2015">Liu et al., 2015</bibRefCitation>
|
||
), oduline (17) (
|
||
<bibRefCitation id="B0476DD9FFF06B50FBF79C1FE382FAA1" author="Huang, S. - D. & Zhang, Y. & He, H. - P. & Li, S. - F. & Tang, G. - H. & Chen, D. - Z. & Cao, M. - M. & Di, Y. - T. & Hao, X. - J." box="[1085,1266,1359,1378]" pageId="1" pageNumber="2" pagination="406 - 410" refId="ref12112" refString="Huang, S. - D., Zhang, Y., He, H. - P., Li, S. - F., Tang, G. - H., Chen, D. - Z., Cao, M. - M., Di, Y. - T., Hao, X. - J., 2013. A new Amaryllidaceae alkaloid from the bulbs of Lycoris radiata. Chin. J. Nat. Med. 11, 406 - 410. https: // doi. org / 10.1016 / S 1875 - 5364 (13) 60060 - 6." type="journal article" year="2013">Huang et al., 2013</bibRefCitation>
|
||
), haemanthamine (18) (
|
||
<bibRefCitation id="B0476DD9FFF06B50FCF09C3AE48AFABE" author="Bastida, J. & Lavilla, R. & Viladomat, F." box="[826,1018,1386,1406]" pageId="1" pageNumber="2" pagination="87 - 179" refId="ref10568" refString="Bastida, J., Lavilla, R., Viladomat, F., 2006. Chemical and biological aspects of Narcissus alkaloids. Alkaloids - Chem. Biol. 63, 87 - 179." type="journal article" year="2006">Bastida et al., 2006</bibRefCitation>
|
||
), tetrahydromasonine (19) (
|
||
<bibRefCitation id="B0476DD9FFF06B50FAD99C3AE412FA5A" author="Dopke, W. & Bienert, M." pageId="1" pageNumber="2" pagination="994 - 997" refId="ref11199" refString="Dopke, W., Bienert, M., 1966. Uber die Struktur und Stereochemie des Odulins und Masonins. Arch. Pharm. Pharm. Med. Chem. 299, 994 - 997. https: // doi. org / 10.1002 / ardp. 19662991205." type="journal article" year="1966">Döpke and Bienert, 1966</bibRefCitation>
|
||
), hippeastrine (20) (
|
||
<bibRefCitation id="B0476DD9FFF06B50FBE59CD6E3A4FA5A" author="Jeffs, P. W. & Abou-Donia, A. & Campau, D. & Staiger, D." box="[1071,1236,1414,1434]" pageId="1" pageNumber="2" pagination="1732 - 1737" refId="ref12390" refString="Jeffs, P. W., Abou-Donia, A., Campau, D., Staiger, D., 1985. Alkaloids of the Amaryllidaceae. 27. Structures of 9 - O-demethylhomolycorine and 5. alpha. - hydroxyhomolycorine. Alkaloids of Crinum defixum, C. scabrum, and C. latifolium. Assignment of aromatic substitution patterns from 1 H-coupled carbon- 13 spectra. J. Org. Chem. 50, 1732 - 1737. https: // doi. org / 10.1021 / jo 00210 a 031." type="journal article" year="1985">Jeffs et al., 1985</bibRefCitation>
|
||
), crinine (21) (
|
||
<bibRefCitation id="B0476DD9FFF06B50FAA49CD6E4EEFA76" author="Kobayashi, S. & Tokumoto, T. & Kihara, M. & Imakura, Y. & Shingu, T. & Taira, Z." pageId="1" pageNumber="2" pagination="3015 - 3022" refId="ref12630" refString="Kobayashi, S., Tokumoto, T., Kihara, M., Imakura, Y., Shingu, T., Taira, Z., 1984. Alkaloidal constituents of Crinum latifolium and Crinum bulbispermum (Amaryllidaceae). Chem. Pharm. Bull. 32, 3015 - 3022. https: // doi. org / 10.1248 / cpb. 32.3015." type="journal article" year="1984">Kobayashi et al., 1984</bibRefCitation>
|
||
), and epimaritidine (22) (
|
||
<bibRefCitation id="B0476DD9FFF06B50FB509CF2E23EFA76" author="Ghosal, S. & Ashutosh & Razdan, S." box="[1178,1358,1442,1462]" pageId="1" pageNumber="2" pagination="635 - 637" refId="ref11396" refString="Ghosal, S., Ashutosh, Razdan, S., 1985. (+) - Epimaritidine, an alkaloid from Zephyranthes rosea. Phytochemistry 24, 635 - 637. https: // doi. org / 10.1016 / S 0031 - 9422 (00) 80796 - 7." type="journal article" year="1985">Ghosal et al., 1985</bibRefCitation>
|
||
) (
|
||
<figureCitation id="4CED0CADFFF06B50FAAF9CF2E2EBFA76" box="[1381,1435,1442,1461]" captionStart="Fig" captionStartId="2.[421,451,1184,1201]" captionTargetBox="[226,1361,153,1160]" captionTargetId="figure-423@2.[225,1362,152,1161]" captionTargetPageId="2" captionText="Fig. 1. Structures of isolated alkaloids from Narcissus pseudonarcissus cv. Dutch Master." figureDoi="http://doi.org/10.5281/zenodo.10483287" httpUri="https://zenodo.org/record/10483287/files/figure.png" pageId="1" pageNumber="2">Fig. 1</figureCitation>
|
||
).
|
||
</paragraph>
|
||
<paragraph id="D4691028FFF06B50FC999CEEE316F80B" blockId="1.[818,1488,968,1992]" pageId="1" pageNumber="2">
|
||
The isolated alkaloids belong to the homolycorine (1, 2, 5, 15–17, 19, 20), galanthamine (10, 11, 13, 14), haemanthamine (3, 18), crinine (21, 22), lycorine (7, 9, 12) and tazettine (8) structure
|
||
<typeStatus id="0B6DAE8AFFF06B50FAF39CA6E21DF9CA" box="[1337,1389,1526,1545]" pageId="1" pageNumber="2">types</typeStatus>
|
||
. The basic core of the novel alkaloid narcimatuline (6) mimics galanthamine and galanthindole, both
|
||
<taxonomicName id="13D66BABFFF06B50FC3F9F7EE3F7F982" box="[1013,1159,1582,1601]" class="Liliopsida" family="Amaryllidaceae" kingdom="Plantae" order="Asparagales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="family">Amaryllidaceae</taxonomicName>
|
||
alkaloids. It is noteworthy that 6 amalgamates the structural features of narcipavline and narcikachnine isolated from
|
||
<taxonomicName id="13D66BABFFF06B50FC759F36E357F9BB" box="[959,1063,1637,1657]" class="Liliopsida" family="Amaryllidaceae" genus="Narcissus" kingdom="Plantae" order="Asparagales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="poeticus">
|
||
<emphasis id="E6A2CC3AFFF06B50FC759F36E357F9BB" bold="true" box="[959,1063,1637,1657]" italics="true" pageId="1" pageNumber="2">N. poeticus</emphasis>
|
||
</taxonomicName>
|
||
cv. Pink Parasol (
|
||
<bibRefCitation id="B0476DD9FFF06B50FB2D9F31E2B1F9BA" author="Safratova, M. & Hostalkova, A. & Hulcova, D. & Breiterova, K. & Hrabcova, V. & Machado, M. & Fontinha, D. & Prudencio, M. & Kunes, J. & Chlebek, J. & Jun, D. & Hrabinova, M. & Novakova, L. & Havelek, R. & Seifrtova, M. & Opletal, L. & Cahlikova, L." box="[1255,1473,1633,1657]" pageId="1" pageNumber="2" pagination="208 - 218" refId="ref13752" refString="Safratova, M., Hostalkova, A., Hulcova, D., Breiterova, K., Hrabcova, V., Machado, M., Fontinha, D., Prudencio, M., Kunes, J., Chlebek, J., Jun, D., Hrabinova, M., Novakova, L., Havelek, R., Seifrtova, M., Opletal, L., Cahlikova, L., 2018. Alkaloids from Narcissus poeticus cv. Pink Parasol of various structural types and their biological activity. Arch Pharm. Res. (Seoul) 41, 208 - 218. https: // doi. org / 10.1007 / s 12272 - 017 - 1000 - 4." type="journal article" year="2018">Šafratová et al., 2018</bibRefCitation>
|
||
). Moreover, 6 is similar to pallidiflorine, which embodies the galanthamine and tazettine templates (
|
||
<bibRefCitation id="B0476DD9FFF06B50FB879FCDE38DF973" author="Codina, C. & Viladomat, F. & Bastida, J. & Rubiralta, M. & Quirion, J. - C." box="[1101,1277,1693,1713]" pageId="1" pageNumber="2" pagination="2685 - 2687" refId="ref11018" refString="Codina, C., Viladomat, F., Bastida, J., Rubiralta, M., Quirion, J. - C., 1990. A heterodimer alkaloid from Narcissus pallidiflorus. Phytochemistry 29, 2685 - 2687. https: // doi. org / 10.1016 / 0031 - 9422 (90) 85214 - Z." type="journal article" year="1990">Codina et al., 1990</bibRefCitation>
|
||
). Alkaloids 1–5, 7–18, and 20–22 have already been isolated from the genus
|
||
<taxonomicName id="13D66BABFFF06B50FABF9FE9E2B9F90F" box="[1397,1481,1721,1740]" class="Liliopsida" family="Amaryllidaceae" genus="Narcissus" kingdom="Plantae" order="Asparagales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="genus">
|
||
<emphasis id="E6A2CC3AFFF06B50FABF9FE9E2B9F90F" bold="true" box="[1397,1481,1721,1740]" italics="true" pageId="1" pageNumber="2">Narcissus</emphasis>
|
||
</taxonomicName>
|
||
, whereas alkaloids 6 and 19 have been obtained for the first time from a natural source. The scaffold of 19 is already known since it has been previously prepared by reduction of oduline (
|
||
<bibRefCitation id="B0476DD9FFF06B50FB139E5DE2B1F8E3" author="Dopke, W. & Bienert, M." box="[1241,1473,1805,1824]" pageId="1" pageNumber="2" pagination="994 - 997" refId="ref11199" refString="Dopke, W., Bienert, M., 1966. Uber die Struktur und Stereochemie des Odulins und Masonins. Arch. Pharm. Pharm. Med. Chem. 299, 994 - 997. https: // doi. org / 10.1002 / ardp. 19662991205." type="journal article" year="1966">Döpke and Bienert, 1966</bibRefCitation>
|
||
). However, literature and databases do not contain any NMR and MS analysis support for 19. All proton and carbon signals of tetrahydromasonine (19) were completely assigned employing 2D-NMR experiments such as COSY, gHSQC, gHMBC and NOESY, and are summarized in Supplementary Material (
|
||
<tableCitation id="99542593FFF06B50FB5A9EC8E392F86F" box="[1168,1250,1944,1964]" captionStart="Table 1" captionStartId="3.[818,868,161,177]" captionTargetPageId="3" captionText="Table 1 1H-NMR and13C-NMR data of new alkaloid 6 (diastereomeric ratio 1:1.1) iso- lated from Narcissus pseudonarcissus cv. Duch Master." pageId="1" pageNumber="2">Table S1</tableCitation>
|
||
). Key gHMBC and COSY correlations are shown in
|
||
<figureCitation id="4CED0CADFFF06B50FBE09EE4E310F804" box="[1066,1120,1972,1991]" captionStart="Fig" captionStartId="2.[100,130,1663,1680]" captionTargetBox="[247,623,1242,1639]" captionTargetId="figure-438@2.[246,624,1241,1640]" captionTargetPageId="2" captionText="Fig. 2. Key gHMBC (blue arrows) and COSY (black dashed arrows) correlations of 19 isolated from Narcissus pseudonarcissus cv. Duch Master. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)" figureDoi="http://doi.org/10.5281/zenodo.10483289" httpUri="https://zenodo.org/record/10483289/files/figure.png" pageId="1" pageNumber="2">Fig. 2</figureCitation>
|
||
.
|
||
</paragraph>
|
||
<caption id="80A940A0FFF36B53FE6F9DF0E3E0FB73" ID-DOI="http://doi.org/10.5281/zenodo.10483287" ID-Zenodo-Dep="10483287" box="[421,1168,1184,1201]" httpUri="https://zenodo.org/record/10483287/files/figure.png" pageId="2" pageNumber="3" startId="2.[421,451,1184,1201]" targetBox="[226,1361,153,1160]" targetPageId="2" targetType="figure">
|
||
<paragraph id="D4691028FFF36B53FE6F9DF0E3E0FB73" blockId="2.[421,1168,1184,1201]" box="[421,1168,1184,1201]" pageId="2" pageNumber="3">
|
||
<emphasis id="E6A2CC3AFFF36B53FE6F9DF0E6AEFB72" bold="true" box="[421,478,1184,1201]" pageId="2" pageNumber="3">Fig. 1.</emphasis>
|
||
Structures of isolated alkaloids from
|
||
<taxonomicName id="13D66BABFFF36B53FCEB9DF0E482FB72" box="[801,1010,1184,1201]" class="Liliopsida" family="Amaryllidaceae" genus="Narcissus" kingdom="Plantae" order="Asparagales" pageId="2" pageNumber="3" phylum="Tracheophyta" rank="species" species="pseudonarcissus">
|
||
<emphasis id="E6A2CC3AFFF36B53FCEB9DF0E482FB72" bold="true" box="[801,1010,1184,1201]" italics="true" pageId="2" pageNumber="3">Narcissus pseudonarcissus</emphasis>
|
||
</taxonomicName>
|
||
cv. Dutch Master.
|
||
</paragraph>
|
||
</caption>
|
||
<caption id="80A940A0FFF36B53FFAE9F2FE623F91E" ID-DOI="http://doi.org/10.5281/zenodo.10483289" ID-Zenodo-Dep="10483289" httpUri="https://zenodo.org/record/10483289/files/figure.png" pageId="2" pageNumber="3" startId="2.[100,130,1663,1680]" targetBox="[247,623,1242,1639]" targetPageId="2" targetType="figure">
|
||
<paragraph id="D4691028FFF36B53FFAE9F2FE623F91E" blockId="2.[100,770,1663,1757]" pageId="2" pageNumber="3">
|
||
<emphasis id="E6A2CC3AFFF36B53FFAE9F2FE7EDF953" bold="true" box="[100,157,1663,1680]" pageId="2" pageNumber="3">Fig. 2.</emphasis>
|
||
Key gHMBC (blue arrows) and COSY (black dashed arrows) correlations of 19 isolated from
|
||
<taxonomicName id="13D66BABFFF36B53FEC59FC8E690F96A" box="[271,480,1688,1705]" class="Liliopsida" family="Amaryllidaceae" genus="Narcissus" kingdom="Plantae" order="Asparagales" pageId="2" pageNumber="3" phylum="Tracheophyta" rank="species" species="pseudonarcissus">
|
||
<emphasis id="E6A2CC3AFFF36B53FEC59FC8E690F96A" bold="true" box="[271,480,1688,1705]" italics="true" pageId="2" pageNumber="3">Narcissus pseudonarcissus</emphasis>
|
||
</taxonomicName>
|
||
cv. Duch Master. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="D4691028FFF36B53FF4F9E5AE24DFA12" blockId="2.[100,770,1802,1988]" lastBlockId="2.[818,1488,1246,1991]" pageId="2" pageNumber="3">
|
||
<materialsCitation id="64BE1A75FFF36B53FF4F9E5AE249FA12" collectionCode="R, S, OH, O, N, IUPAC" pageId="2" pageNumber="3" specimenCode="R2" specimenCount="1">
|
||
The absolute configuration of tetrahydromasonine has been determined by X-ray study. The solid state structure determined by single crystal X-ray diffraction (sc-XRD) techniques (
|
||
<figureCitation id="4CED0CADFFF36B53FDE59E12E519F896" box="[559,617,1858,1877]" captionStart="Fig" captionStartId="3.[100,130,734,751]" captionTargetBox="[266,591,172,705]" captionTargetId="figure-682@3.[257,612,152,711]" captionTargetPageId="3" captionText="Fig. 3. Molecular structure of 19 - ORTEP view, 50% probability. Selected interatomic distances (Å): O1-C6 1.431(4), C1′-C2′ 1.402(4), C1′-C6′ 1.411(5), C1′-C7 1.516(4), N1-C8 1.462(5), N1-C7A 1.484(4), N1-C2 1.484(4), C2′-C3′ 1.399(4), C2′-C9 1.521(5), C2-C3 1.523(5), O2-C9 1.422(4), C3-C3A 1.518(5), C3′-C4′ 1.363(5), O3-C4′ 1.386(4), O3-C10 1.427(4), C4-C3A 1.312(5), C4-C5, 1.502(5), O4-C5′ 1.384(4), O4-C10 1.437(4), C4′-C5′ 1.378(5), C5-C6 1.524(5), C5′-C6′ 1.369(5), C7-C7A 1.535(4), C7-C6 1.542(5), C3A-C7A 1.508(5)." figureDoi="http://doi.org/10.5281/zenodo.10483291" httpUri="https://zenodo.org/record/10483291/files/figure.png" pageId="2" pageNumber="3">Fig. 3</figureCitation>
|
||
) resembles the structures of natural products or their derivatives containing a similar core and arrangement of the skeletal heterocycle ((3a
|
||
<emphasis id="E6A2CC3AFFF36B53FD119E2AE599F84E" bold="true" box="[731,745,1914,1933]" italics="true" pageId="2" pageNumber="3">
|
||
<collectionCode id="B2C788EDFFF36B53FD119E2AE599F84E" box="[731,745,1914,1933]" country="Chile" name="Departamento de Geologia, Universidad de Chile" pageId="2" pageNumber="3">R</collectionCode>
|
||
</emphasis>
|
||
,5
|
||
<emphasis id="E6A2CC3AFFF36B53FD319E2AE71FF86A" bold="true" italics="true" pageId="2" pageNumber="3">
|
||
-
|
||
<collectionCode id="B2C788EDFFF36B53FFAE9EC6E71FF86A" box="[100,111,1942,1961]" country="Sweden" lsid="urn:lsid:biocol.org:col:15668" name="Department of Botany, Swedish Museum of Natural History" pageId="2" pageNumber="3" type="Herbarium">S</collectionCode>
|
||
</emphasis>
|
||
,5a
|
||
<emphasis id="E6A2CC3AFFF36B53FF469EC6E7EAF86A" bold="true" box="[140,154,1942,1961]" italics="true" pageId="2" pageNumber="3">
|
||
<collectionCode id="B2C788EDFFF36B53FF469EC6E7EAF86A" box="[140,154,1942,1961]" country="Chile" name="Departamento de Geologia, Universidad de Chile" pageId="2" pageNumber="3">R</collectionCode>
|
||
</emphasis>
|
||
,11b
|
||
<emphasis id="E6A2CC3AFFF36B53FF099EC6E7BEF86A" bold="true" box="[195,206,1942,1961]" italics="true" pageId="2" pageNumber="3">
|
||
<collectionCode id="B2C788EDFFF36B53FF099EC6E7BEF86A" box="[195,206,1942,1961]" country="Sweden" lsid="urn:lsid:biocol.org:col:15668" name="Department of Botany, Swedish Museum of Natural History" pageId="2" pageNumber="3" type="Herbarium">S</collectionCode>
|
||
</emphasis>
|
||
,11c
|
||
<emphasis id="E6A2CC3AFFF36B53FF3C9EC6E674F86A" bold="true" box="[246,260,1942,1961]" italics="true" pageId="2" pageNumber="3">
|
||
<collectionCode id="B2C788EDFFF36B53FF3C9EC6E674F86A" box="[246,260,1942,1961]" country="Chile" name="Departamento de Geologia, Universidad de Chile" pageId="2" pageNumber="3">R</collectionCode>
|
||
</emphasis>
|
||
)-5,5a-dihydroxyisopropylidene-1,2,3a,3b,4,5,11b,11c-octahydro-(1,3)dioxolo(4,5-f)pyrrolo(3,2,1-d,e) phenanthridine) (
|
||
<bibRefCitation id="B0476DD9FFF36B53FC149D8EE3D6FB31" author="Haning, H. & Giro-Manas, C. & Paddock, V. L. & Bochet, C. G. & White, A. J. P. & Bernardinelli, G. & Mann, I. & Oppolzer, W. & Spivey, A. C." box="[990,1190,1246,1266]" pageId="2" pageNumber="3" pagination="2809 - 2820" refId="ref11767" refString="Haning, H., Giro-Manas, C., Paddock, V. L., Bochet, C. G., White, A. J. P., Bernardinelli, G., Mann, I., Oppolzer, W., Spivey, A. C., 2011. Total synthesis of the Amaryllidaceae alkaloid clivonine. Org. Biomol. Chem. 9, 2809 - 2820. https: // doi. org / 10.1039 / C 0 OB 00895 H." type="journal article" year="2011">Haning et al., 2011</bibRefCitation>
|
||
). In detail, the compound is composed of two bicyclic systems interconnected by a typical single bond (
|
||
<figureCitation id="4CED0CADFFF36B53FCA59C46E4D4FAEA" box="[879,932,1302,1321]" captionStart="Fig" captionStartId="3.[100,130,734,751]" captionTargetBox="[266,591,172,705]" captionTargetId="figure-682@3.[257,612,152,711]" captionTargetPageId="3" captionText="Fig. 3. Molecular structure of 19 - ORTEP view, 50% probability. Selected interatomic distances (Å): O1-C6 1.431(4), C1′-C2′ 1.402(4), C1′-C6′ 1.411(5), C1′-C7 1.516(4), N1-C8 1.462(5), N1-C7A 1.484(4), N1-C2 1.484(4), C2′-C3′ 1.399(4), C2′-C9 1.521(5), C2-C3 1.523(5), O2-C9 1.422(4), C3-C3A 1.518(5), C3′-C4′ 1.363(5), O3-C4′ 1.386(4), O3-C10 1.427(4), C4-C3A 1.312(5), C4-C5, 1.502(5), O4-C5′ 1.384(4), O4-C10 1.437(4), C4′-C5′ 1.378(5), C5-C6 1.524(5), C5′-C6′ 1.369(5), C7-C7A 1.535(4), C7-C6 1.542(5), C3A-C7A 1.508(5)." figureDoi="http://doi.org/10.5281/zenodo.10483291" httpUri="https://zenodo.org/record/10483291/files/figure.png" pageId="2" pageNumber="3">Fig. 3</figureCitation>
|
||
). The presence of saturated as well as unsaturated bonds is demonstrated by values of interatomic distances recorded in the caption of
|
||
<figureCitation id="4CED0CADFFF36B53FC879C1EE4F4FAA2" box="[845,900,1358,1377]" captionStart="Fig" captionStartId="3.[100,130,734,751]" captionTargetBox="[266,591,172,705]" captionTargetId="figure-682@3.[257,612,152,711]" captionTargetPageId="3" captionText="Fig. 3. Molecular structure of 19 - ORTEP view, 50% probability. Selected interatomic distances (Å): O1-C6 1.431(4), C1′-C2′ 1.402(4), C1′-C6′ 1.411(5), C1′-C7 1.516(4), N1-C8 1.462(5), N1-C7A 1.484(4), N1-C2 1.484(4), C2′-C3′ 1.399(4), C2′-C9 1.521(5), C2-C3 1.523(5), O2-C9 1.422(4), C3-C3A 1.518(5), C3′-C4′ 1.363(5), O3-C4′ 1.386(4), O3-C10 1.427(4), C4-C3A 1.312(5), C4-C5, 1.502(5), O4-C5′ 1.384(4), O4-C10 1.437(4), C4′-C5′ 1.378(5), C5-C6 1.524(5), C5′-C6′ 1.369(5), C7-C7A 1.535(4), C7-C6 1.542(5), C3A-C7A 1.508(5)." figureDoi="http://doi.org/10.5281/zenodo.10483291" httpUri="https://zenodo.org/record/10483291/files/figure.png" pageId="2" pageNumber="3">Fig. 3</figureCitation>
|
||
. The presence and orientation of the
|
||
<collectionCode id="B2C788EDFFF36B53FB3C9C1EE265FAA2" box="[1270,1301,1358,1377]" country="Czech Republic" lsid="urn:lsid:biocol.org:col:12554" name="Agricultural Museum of Praha" pageId="2" pageNumber="3" type="Herbarium">OH</collectionCode>
|
||
groups lead to the formation of extensive supramolecular architecture promoted by
|
||
<collectionCode id="B2C788EDFFF36B53FCF89CD6E421FA5A" box="[818,849,1414,1433]" country="Czech Republic" lsid="urn:lsid:biocol.org:col:12554" name="Agricultural Museum of Praha" pageId="2" pageNumber="3" type="Herbarium">OH</collectionCode>
|
||
<emphasis id="E6A2CC3AFFF36B53FC9B9CD6E415FA5A" bold="true" box="[849,869,1414,1433]" pageId="2" pageNumber="3">⋯</emphasis>
|
||
<collectionCode id="B2C788EDFFF36B53FCAF9CD6E405FA5A" box="[869,885,1414,1433]" country="Norway" lsid="urn:lsid:biocol.org:col:13093" name="Botanical Museum - University of Oslo" pageId="2" pageNumber="3" type="Herbarium">O</collectionCode>
|
||
and
|
||
<collectionCode id="B2C788EDFFF36B53FC629CD6E4B7FA5A" box="[936,967,1414,1433]" country="Czech Republic" lsid="urn:lsid:biocol.org:col:12554" name="Agricultural Museum of Praha" pageId="2" pageNumber="3" type="Herbarium">OH</collectionCode>
|
||
<emphasis id="E6A2CC3AFFF36B53FC029CD6E4ACFA5A" bold="true" box="[968,988,1414,1433]" pageId="2" pageNumber="3">⋯</emphasis>
|
||
<collectionCode id="B2C788EDFFF36B53FC119CD6E49AFA5A" box="[987,1002,1414,1433]" country="China" lsid="urn:lsid:biocol.org:col:13092" name="Nanjing University" pageId="2" pageNumber="3" type="Herbarium">N</collectionCode>
|
||
bridge connections (Supplementary Material,
|
||
<figureCitation id="4CED0CADFFF36B53FA669CD6E439FA76" captionStart="Fig" captionStartId="2.[421,451,1184,1201]" captionTargetBox="[226,1361,153,1160]" captionTargetId="figure-423@2.[225,1362,152,1161]" captionTargetPageId="2" captionText="Fig. 1. Structures of isolated alkaloids from Narcissus pseudonarcissus cv. Dutch Master." figureDoi="http://doi.org/10.5281/zenodo.10483287" httpUri="https://zenodo.org/record/10483287/files/figure.png" pageId="2" pageNumber="3">Fig. S1</figureCitation>
|
||
,
|
||
<tableCitation id="99542593FFF36B53FC9C9CF2E4D8FA76" box="[854,936,1442,1461]" captionStart="Table 2" captionStartId="4.[100,150,1165,1181]" captionTargetPageId="4" captionText="Table 2 hAChE, hBuChE, POP and GSK-3β inhibitory activities of the tested Amaryllidaceae alkaloids isolated from Narcissus pseudonarcissus cv. Dutch Master expressed as IC50." pageId="2" pageNumber="3">Table S2</tableCitation>
|
||
). According to the
|
||
<collectionCode id="B2C788EDFFF36B53FBAF9CF2E3D3FA76" box="[1125,1187,1442,1461]" pageId="2" pageNumber="3">IUPAC</collectionCode>
|
||
nomenclature, rings of
|
||
<specimenCode id="8470B853FFF36B53FA439CF2E2D0FA69" box="[1417,1440,1438,1461]" collectionCode="R" country="Chile" name="Departamento de Geologia, Universidad de Chile" pageId="2" pageNumber="3">
|
||
R
|
||
<superScript id="23A3BD60FFF36B53FA5D9CCEE2D0FA69" attach="left" box="[1431,1440,1438,1450]" fontSize="5" pageId="2" pageNumber="3">2</superScript>
|
||
</specimenCode>
|
||
<subScript id="4852126DFFF36B53FA5D9CFBE2D0FA74" attach="left" box="[1431,1440,1451,1463]" fontSize="5" pageId="2" pageNumber="3">2</subScript>
|
||
(16)
|
||
<typeStatus id="0B6DAE8AFFF36B53FCF89CEEE42BFA12" box="[818,859,1470,1489]" pageId="2" pageNumber="3">type</typeStatus>
|
||
promote the formation of 1D chains of molecules
|
||
</materialsCitation>
|
||
.
|
||
</paragraph>
|
||
<paragraph id="D4691028FFF36B52FC999C8AE57DF804" blockId="2.[818,1488,1246,1991]" lastBlockId="3.[100,771,968,1992]" lastPageId="3" lastPageNumber="4" pageId="2" pageNumber="3">
|
||
The novel alkaloid 6 was obtained as a light yellow viscous solid. ESI-HRMS of 6 showed a molecular ion peak [M + H]
|
||
<superScript id="23A3BD60FFF36B53FAA49CA2E20EFA3D" attach="left" box="[1390,1406,1522,1534]" fontSize="5" pageId="2" pageNumber="3">+</superScript>
|
||
at m/z 539.2549, corresponding to formula C
|
||
<subScript id="4852126DFFF36B53FB6A9F4AE3C2F9E5" attach="both" box="[1184,1202,1562,1574]" fontSize="5" pageId="2" pageNumber="3">33</subScript>
|
||
H
|
||
<subScript id="4852126DFFF36B53FB089F4AE3A4F9E5" attach="both" box="[1218,1236,1562,1574]" fontSize="5" pageId="2" pageNumber="3">35</subScript>
|
||
N
|
||
<subScript id="4852126DFFF36B53FB299F4AE39CF9E5" attach="both" box="[1251,1260,1562,1574]" fontSize="5" pageId="2" pageNumber="3">2</subScript>
|
||
O
|
||
<subScript id="4852126DFFF36B53FB369F4AE275F9E5" attach="left" box="[1276,1285,1562,1574]" fontSize="5" pageId="2" pageNumber="3">5</subScript>
|
||
(calc. 539.2541).
|
||
<superScript id="23A3BD60FFF36B53FA7C9F5EE2CFF9D9" attach="right" box="[1462,1471,1550,1562]" fontSize="5" pageId="2" pageNumber="3">1</superScript>
|
||
H NMR and
|
||
<superScript id="23A3BD60FFF36B53FC5E9F79E4D6F9F6" attach="right" box="[916,934,1577,1589]" fontSize="5" pageId="2" pageNumber="3">13</superScript>
|
||
C NMR spectra showed signals apparently resembling the structural features of 6. The sample was isolated as a mixture of two diastereoisomers. The
|
||
<superScript id="23A3BD60FFF36B53FBC09F31E363F9AE" attach="right" box="[1034,1043,1633,1645]" fontSize="5" pageId="2" pageNumber="3">1</superScript>
|
||
H NMR spectra allowed to detect the diastereomeric ratio 1:1.1 (isomer A: isomer B). The
|
||
<superScript id="23A3BD60FFF36B53FADA9F2DE269F94A" attach="right" box="[1296,1305,1661,1673]" fontSize="5" pageId="2" pageNumber="3">1</superScript>
|
||
H NMR data of 6 (
|
||
<tableCitation id="99542593FFF36B53FCF09FCDE4F4F973" box="[826,900,1693,1712]" captionStart="Table 1" captionStartId="3.[818,868,161,177]" captionTargetPageId="3" captionText="Table 1 1H-NMR and13C-NMR data of new alkaloid 6 (diastereomeric ratio 1:1.1) iso- lated from Narcissus pseudonarcissus cv. Duch Master." pageId="2" pageNumber="3">Table 1</tableCitation>
|
||
) revealed the presence of 68 protons (34 protons for each isomer) with fourteen of them in the aromatic region and the rest of the signals in the aliphatic area. Four aromatic protons were singlets (
|
||
<subScript id="4852126DFFF36B53FA7D9F85E2BFF929" attach="left" box="[1463,1487,1749,1770]" fontSize="5" pageId="2" pageNumber="3">δH</subScript>
|
||
7.01, H3′ and 6.74, H7′ for isomer A; 7.07, H3′ and 6.77, H7′ for isomer B), typical for 1, 2, 4, 5-tetrasubstituted benzene ring of each isomer. Four aromatic signals were doublets with
|
||
<emphasis id="E6A2CC3AFFF36B53FB089E79E395F8FF" bold="true" box="[1218,1253,1833,1852]" italics="true" pageId="2" pageNumber="3">J =</emphasis>
|
||
8.0 Hz (
|
||
<subScript id="4852126DFFF36B53FAFE9E78E23CF8FD" attach="left" box="[1332,1356,1832,1854]" fontSize="5" pageId="2" pageNumber="3">δH</subScript>
|
||
6.65, H7 and
|
||
<subScript id="4852126DFFF36B53FCF89E14E439F89A" attach="left" box="[818,841,1860,1881]" fontSize="5" pageId="2" pageNumber="3">δH</subScript>
|
||
6.44, H8 for isomer A;
|
||
<subScript id="4852126DFFF36B53FBE59E14E336F89A" attach="left" box="[1071,1094,1860,1881]" fontSize="5" pageId="2" pageNumber="3">δH</subScript>
|
||
6.62, H7 and
|
||
<subScript id="4852126DFFF36B53FB189E14E399F89A" attach="left" box="[1234,1257,1860,1881]" fontSize="5" pageId="2" pageNumber="3">δH</subScript>
|
||
6.56, H8 for isomer B). The other aromatic doublets with
|
||
<emphasis id="E6A2CC3AFFF36B53FB4F9E30E3D8F8B0" bold="true" box="[1157,1192,1888,1907]" italics="true" pageId="2" pageNumber="3">J =</emphasis>
|
||
7.4 Hz (
|
||
<subScript id="4852126DFFF36B53FB339E30E261F8B6" attach="left" box="[1273,1297,1888,1909]" fontSize="5" pageId="2" pageNumber="3">δH</subScript>
|
||
7.03, H12′ and
|
||
<subScript id="4852126DFFF36B53FA729E30E2BFF8B6" attach="left" box="[1464,1487,1888,1909]" fontSize="5" pageId="2" pageNumber="3">δH</subScript>
|
||
6.83, H10′ for isomer A; ְ
|
||
<subScript id="4852126DFFF36B53FBEB9E2CE349F852" attach="left" box="[1057,1081,1916,1937]" fontSize="5" pageId="2" pageNumber="3">δH</subScript>
|
||
7.03, H12′ and
|
||
<subScript id="4852126DFFF36B53FB059E2CE396F852" attach="left" box="[1231,1254,1916,1937]" fontSize="5" pageId="2" pageNumber="3">δH</subScript>
|
||
6.71, H10′ for isomer B) and two triplets with
|
||
<emphasis id="E6A2CC3AFFF36B53FC339EC8E36CF868" bold="true" box="[1017,1052,1944,1963]" italics="true" pageId="2" pageNumber="3">J =</emphasis>
|
||
7.4 Hz (ְ
|
||
<subScript id="4852126DFFF36B53FBBB9EC8E3F8F86E" attach="left" box="[1137,1160,1944,1965]" fontSize="5" pageId="2" pageNumber="3">δH</subScript>
|
||
6.68, H11′ isomer A;
|
||
<subScript id="4852126DFFF36B53FA9B9EC8E218F86E" attach="left" box="[1361,1384,1944,1965]" fontSize="5" pageId="2" pageNumber="3">δH</subScript>
|
||
6.62, H11′ isomer B) proposed the structural fragments of 1, 2, 3-trisubstituted benzene ring. The signals in the upfield region were mostly multiplets. In the
|
||
<superScript id="23A3BD60FFF26B52FF629AB0E7CAFC2F" attach="right" box="[168,186,992,1004]" fontSize="5" pageId="3" pageNumber="4">13</superScript>
|
||
C NMR spectrum of 6, 58 carbon atoms were detected and assigned using gHSQC data. Eight carbons have shown identical positions of resonance for both diastereoisomers, namely: one signal for a carbonyl carbon (
|
||
<subScript id="4852126DFFF26B52FEC79D68E653FB8E" attach="left" box="[269,291,1080,1101]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
209.2, C3), three oxygenated quaternary sp
|
||
<superScript id="23A3BD60FFF26B52FD079D64E5A6FB83" attach="left" box="[717,726,1076,1088]" fontSize="5" pageId="3" pageNumber="4">2</superScript>
|
||
carbons (
|
||
<subScript id="4852126DFFF26B52FF579D04E7C3FBAA" attach="left" box="[157,179,1108,1129]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
146.9, C3a’;
|
||
<subScript id="4852126DFFF26B52FEE49D04E633FBAA" attach="left" box="[302,323,1108,1129]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
146.7, C5a;
|
||
<subScript id="4852126DFFF26B52FE739D04E6BEFBAA" attach="left" box="[441,462,1108,1129]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
143.6, C6), three quaternary sp
|
||
<superScript id="23A3BD60FFF26B52FD339D00E472FB9F" attach="left" box="[761,770,1104,1116]" fontSize="5" pageId="3" pageNumber="4">2</superScript>
|
||
carbons (
|
||
<subScript id="4852126DFFF26B52FF749D20E7A5FB46" attach="left" box="[190,213,1136,1157]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
132.0, C8b;
|
||
<subScript id="4852126DFFF26B52FE919D20E600FB46" attach="left" box="[347,368,1136,1157]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
129.9, C8a;
|
||
<subScript id="4852126DFFF26B52FE3E9D20E579FB46" attach="left" box="[500,521,1136,1157]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
122.8, C2′) and one sp
|
||
<superScript id="23A3BD60FFF26B52FD339D3CE472FBBB" attach="left" box="[761,770,1132,1144]" fontSize="5" pageId="3" pageNumber="4">2</superScript>
|
||
methine (
|
||
<subScript id="4852126DFFF26B52FF0B9DDBE7A7FB63" attach="left" box="[193,215,1163,1184]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
117.9, C11′). Signals that were separate for each of the isomers include two methoxy groups (
|
||
<subScript id="4852126DFFF26B52FE059DF7E695FB7F" attach="left" box="[463,485,1191,1212]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
55.96, C6-OCH
|
||
<subScript id="4852126DFFF26B52FDB69DE0E5F5FB7F" attach="left" box="[636,645,1200,1212]" fontSize="5" pageId="3" pageNumber="4">3</subScript>
|
||
isomer A;
|
||
<subScript id="4852126DFFF26B52FD279DF7E472FB7F" attach="left" box="[749,770,1191,1212]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
55.95, C6-OCH
|
||
<subScript id="4852126DFFF26B52FF399D9CE78CFB1B" attach="left" box="[243,252,1228,1240]" fontSize="5" pageId="3" pageNumber="4">3</subScript>
|
||
isomer B), two NCH
|
||
<subScript id="4852126DFFF26B52FE0A9D9CE6B9FB1B" attach="left" box="[448,457,1228,1240]" fontSize="5" pageId="3" pageNumber="4">3</subScript>
|
||
groups (
|
||
<subScript id="4852126DFFF26B52FDD69D93E542FB1B" attach="left" box="[540,562,1219,1240]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
38.8, N2′-
|
||
<collectingCountry id="ACC150B8FFF26B52FD5E9D92E5C3FB15" box="[660,691,1218,1238]" name="Switzerland" pageId="3" pageNumber="4">CH</collectingCountry>
|
||
<subScript id="4852126DFFF26B52FD799D9CE5CCFB1B" attach="left" box="[691,700,1228,1240]" fontSize="5" pageId="3" pageNumber="4">3</subScript>
|
||
isomer A;
|
||
<subScript id="4852126DFFF26B52FF4B9D8FE7E6FB37" attach="left" box="[129,150,1247,1268]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
38.7, N2′-
|
||
<collectingCountry id="ACC150B8FFF26B52FF319D8EE66AFB31" box="[251,282,1246,1266]" name="Switzerland" pageId="3" pageNumber="4">CH</collectingCountry>
|
||
<subScript id="4852126DFFF26B52FED09DB8E653FB37" attach="left" box="[282,291,1256,1268]" fontSize="5" pageId="3" pageNumber="4">3</subScript>
|
||
isomer B), twos -O-CH
|
||
<subScript id="4852126DFFF26B52FDCE9DB8E57DFB37" attach="left" box="[516,525,1256,1268]" fontSize="5" pageId="3" pageNumber="4">2</subScript>
|
||
-O- groups (
|
||
<subScript id="4852126DFFF26B52FD4B9D8FE5E7FB37" attach="left" box="[641,663,1247,1268]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
101.0, C5′ isomer A;
|
||
<subScript id="4852126DFFF26B52FF0F9DABE7AAFAD3" attach="left" box="[197,218,1275,1296]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
100.9, C5′ isomer B), twelve sp
|
||
<superScript id="23A3BD60FFF26B52FDCD9DA7E560FAC0" attach="left" box="[519,528,1271,1283]" fontSize="5" pageId="3" pageNumber="4">2</superScript>
|
||
methines (
|
||
<subScript id="4852126DFFF26B52FDB39DABE5FFFAD3" attach="left" box="[633,655,1275,1296]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
130.4, C10′ and
|
||
<subScript id="4852126DFFF26B52FF449C47E7D3FAEF" attach="left" box="[142,163,1303,1324]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
123.22, C12′ and
|
||
<subScript id="4852126DFFF26B52FE9B9C47E616FAEF" attach="left" box="[337,358,1303,1324]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
122.23, C8 and
|
||
<subScript id="4852126DFFF26B52FDCE9C47E569FAEF" attach="left" box="[516,537,1303,1324]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
110.9, C7 and
|
||
<subScript id="4852126DFFF26B52FD619C47E5B0FAEF" attach="left" box="[683,704,1303,1324]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
110.5, C7′ and
|
||
<subScript id="4852126DFFF26B52FF789C63E7B7FA8B" attach="left" box="[178,199,1331,1352]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
108.7, C3′ for isomer A;
|
||
<subScript id="4852126DFFF26B52FE7C9C63E6BBFA8B" attach="left" box="[438,459,1331,1352]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
130.2, C10′ and
|
||
<subScript id="4852126DFFF26B52FDA49C63E5F3FA8B" attach="left" box="[622,643,1331,1352]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
123.24, C12′ and
|
||
<subScript id="4852126DFFF26B52FF479C1FE7D2FAA7" attach="left" box="[141,162,1359,1380]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
122.20, C8 and
|
||
<subScript id="4852126DFFF26B52FEF69C1FE621FAA7" attach="left" box="[316,337,1359,1380]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
111.0, C7 and
|
||
<subScript id="4852126DFFF26B52FE159C1FE684FAA7" attach="left" box="[479,500,1359,1380]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
110.3, C7′ and
|
||
<subScript id="4852126DFFF26B52FD4D9C1FE5ECFAA7" attach="left" box="[647,668,1359,1380]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
108.4, C3′ for isomer B), two oxygenated methines (
|
||
<subScript id="4852126DFFF26B52FE359C3BE565FA43" attach="left" box="[511,533,1387,1408]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
88.3, C4a isomer A;
|
||
<subScript id="4852126DFFF26B52FD279C3BE472FA43" attach="left" box="[749,770,1387,1408]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
88.2, C4a isomer B), eight nitrogenated methylenes (
|
||
<subScript id="4852126DFFF26B52FD9E9CD7E51AFA58" attach="left" box="[596,618,1415,1435]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
57.6, C9 and
|
||
<subScript id="4852126DFFF26B52FD279CD7E472FA58" attach="left" box="[749,770,1415,1435]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
57.1, C14′ and
|
||
<subScript id="4852126DFFF26B52FF3F9CF2E67AFA74" attach="left" box="[245,266,1442,1463]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
54.9, C1′ and
|
||
<subScript id="4852126DFFF26B52FE5C9CF2E6DBFA74" attach="left" box="[406,427,1442,1463]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
52.3, C11 for isomer A;
|
||
<subScript id="4852126DFFF26B52FD5C9CF2E5DCFA74" attach="left" box="[662,684,1442,1463]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
57.9, C9 and
|
||
<subScript id="4852126DFFF26B52FF449CEEE7D3FA10" attach="left" box="[142,163,1470,1491]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
56.9, C14′ and
|
||
<subScript id="4852126DFFF26B52FEF69CEEE621FA10" attach="left" box="[316,337,1470,1491]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
53.7, C1′ and
|
||
<subScript id="4852126DFFF26B52FE179CEEE682FA10" attach="left" box="[477,498,1470,1491]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
51.1, C11 for isomer B) and ten methylene groups (
|
||
<subScript id="4852126DFFF26B52FE8A9C8AE627FA2C" attach="left" box="[320,343,1498,1519]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
40.05, C4 and
|
||
<subScript id="4852126DFFF26B52FE219C8AE570FA2C" attach="left" box="[491,512,1498,1519]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
37.4, C12 and
|
||
<subScript id="4852126DFFF26B52FD5F9C8AE5DAFA2C" attach="left" box="[661,682,1498,1519]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
35.7, C2 and 29.7, C1 and
|
||
<subScript id="4852126DFFF26B52FEC79CA6E652F9C8" attach="left" box="[269,290,1526,1547]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
28.6, C13′ for isomer A;
|
||
<subScript id="4852126DFFF26B52FDDA9CA6E555F9C8" attach="left" box="[528,549,1526,1547]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
40.03, C4 and
|
||
<subScript id="4852126DFFF26B52FD7D9CA6E5BCF9C8" attach="left" box="[695,716,1526,1547]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
36.4, C12 and
|
||
<subScript id="4852126DFFF26B52FF719F42E7A0F9E4" attach="left" box="[187,208,1554,1575]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
35.6, C2 and
|
||
<subScript id="4852126DFFF26B52FE909F42E61FF9E4" attach="left" box="[346,367,1554,1575]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
29.6, C1 and
|
||
<subScript id="4852126DFFF26B52FE329F42E57EF9E4" attach="left" box="[504,526,1554,1575]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
28.5, C13′ for isomer B). The
|
||
<superScript id="23A3BD60FFF26B52FF5F9F7AE7D7F9F5" attach="right" box="[149,167,1578,1590]" fontSize="5" pageId="3" pageNumber="4">13</superScript>
|
||
C-NMR spectrum also exhibited two oxygenated quaternary carbon atoms (
|
||
<subScript id="4852126DFFF26B52FF389F1AE678F99C" attach="left" box="[242,264,1610,1631]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
146.0, C6a′ isomer A;
|
||
<subScript id="4852126DFFF26B52FE2C9F1AE68BF99C" attach="left" box="[486,507,1610,1631]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
145.8, C6a′ isomer B), two nitrogenated quaternary sp
|
||
<superScript id="23A3BD60FFF26B52FEA79F32E606F9AD" attach="left" box="[365,374,1634,1646]" fontSize="5" pageId="3" pageNumber="4">2</superScript>
|
||
carbons (
|
||
<subScript id="4852126DFFF26B52FE169F36E682F9B8" attach="left" box="[476,498,1638,1659]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
150.5, C15a′ isomer A;
|
||
<subScript id="4852126DFFF26B52FD279F36E472F9B8" attach="left" box="[749,770,1638,1659]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
150.4, C15a′ isomer B), six quaternary sp
|
||
<superScript id="23A3BD60FFF26B52FE299F2EE69CF949" attach="left" box="[483,492,1662,1674]" fontSize="5" pageId="3" pageNumber="4">2</superScript>
|
||
carbons (
|
||
<subScript id="4852126DFFF26B52FD8F9FD1E52CF954" attach="left" box="[581,604,1665,1687]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
133.6, C8′ and
|
||
<subScript id="4852126DFFF26B52FD279FD1E472F954" attach="left" box="[749,770,1665,1687]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
131.7, C9′ and
|
||
<subScript id="4852126DFFF26B52FF379FCDE662F971" attach="left" box="[253,274,1693,1714]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
131.01, C12a′ for isomer A;
|
||
<subScript id="4852126DFFF26B52FDFF9FCDE53AF971" attach="left" box="[565,586,1693,1714]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
133.4, C8′ and
|
||
<subScript id="4852126DFFF26B52FD279FCDE472F971" attach="left" box="[749,770,1693,1714]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
131.4, C9′ and
|
||
<subScript id="4852126DFFF26B52FF3F9FE9E67AF90D" attach="left" box="[245,266,1721,1742]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
131.05, C12a′ for isomer B), and two quaternary sp
|
||
<superScript id="23A3BD60FFF26B52FD339FE5E472F902" attach="left" box="[761,770,1717,1729]" fontSize="5" pageId="3" pageNumber="4">3</superScript>
|
||
carbon atoms (
|
||
<subScript id="4852126DFFF26B52FF399F85E679F929" attach="left" box="[243,265,1749,1770]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
47.5, C13 isomer A;
|
||
<subScript id="4852126DFFF26B52FE1C9F85E69BF929" attach="left" box="[470,491,1749,1770]" fontSize="5" pageId="3" pageNumber="4">δC</subScript>
|
||
47.4, C13 isomer B). Signals have been successfully determined to the individual isomers. The 2D experiments such as gHMBC and gCOSY unequivocally assigned the constitution of compound 6 (
|
||
<figureCitation id="4CED0CADFFF26B52FEB09E79E6C0F8FF" box="[378,432,1833,1852]" captionStart="Fig" captionStartId="4.[100,130,800,817]" captionTargetBox="[181,688,153,777]" captionTargetId="figure-424@4.[180,689,152,778]" captionTargetPageId="4" captionText="Fig. 4. Key gHMBC (blue arrows) and COSY (black dashed arrows) correlations of new compound 6 isolated from Narcissus pseudonarcissus cv. Duch Master. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)" figureDoi="http://doi.org/10.5281/zenodo.10483293" httpUri="https://zenodo.org/record/10483293/files/figure.png" pageId="3" pageNumber="4">Fig. 4</figureCitation>
|
||
). The results allowed identification of three sub-structural fragments (
|
||
<figureCitation id="4CED0CADFFF26B52FE0A9E15E68BF89B" box="[448,507,1861,1880]" captionStart="Fig" captionStartId="4.[100,130,800,817]" captionTargetBox="[181,688,153,777]" captionTargetId="figure-424@4.[180,689,152,778]" captionTargetPageId="4" captionText="Fig. 4. Key gHMBC (blue arrows) and COSY (black dashed arrows) correlations of new compound 6 isolated from Narcissus pseudonarcissus cv. Duch Master. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)" figureDoi="http://doi.org/10.5281/zenodo.10483293" httpUri="https://zenodo.org/record/10483293/files/figure.png" pageId="3" pageNumber="4">Fig. 4</figureCitation>
|
||
): fragments A, B, and C. Fragment A was attached to fragment B via a methylene group (C1′) connecting the nitrogen of fragment A with carbon 2′ of fragment B. Connection of carbon 9′ of
|
||
<emphasis id="E6A2CC3AFFF26B52FEA89EC9E601F86F" bold="true" box="[354,369,1945,1964]" italics="true" pageId="3" pageNumber="4">N</emphasis>
|
||
-methylindoline to carbon 8′ of fragment B was determined by key gHMBC correlations.
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |