Amaryllidaceae Alkaloids of Different Structural Types from Narcissus L. cv. Professor Einstein and Their Cytotoxic Activity
Status PubMed-not-MEDLINE Jazyk angličtina Země Švýcarsko Médium electronic
Typ dokumentu časopisecké články
Grantová podpora
SVV UK 260 412; 260 401; Progres/UK Q40 and Q42
Univerzita Karlova
No. 00179906
Universitz Hospital, Hradec Králové, Czech Republic
Long-term development plan
Faculty of Military Health Sciences
Reg. No. CZ.02.1.01/0.0/0.0/18_069/0010046
European Union
PubMed
31978967
PubMed Central
PMC7076679
DOI
10.3390/plants9020137
PII: plants9020137
Knihovny.cz E-zdroje
- Klíčová slova
- 7-oxonorpluviine, Amaryllidaceae, Narcissus cv. Professor Einstein, cytotoxicity, pancracine,
- Publikační typ
- časopisecké články MeSH
In this detailed phytochemical study of Narcissus cv. Professor Einstein, we isolated 23 previously known Amaryllidaceae alkaloids (1-23) of several structural types and one previously undescribed alkaloid, 7-oxonorpluviine. The chemical structures were identified by various spectroscopic methods (GC-MS, LC-MS, 1D, and 2D NMR spectroscopy) and were compared with literature data. Alkaloids which had not previously been isolated and studied for cytotoxicity before and which were obtained in sufficient amounts were assayed for their cytotoxic activity on a panel of human cancer cell lines of different histotype. Above that, MRC-5 human fibroblasts were used as a control noncancerous cell line to determine the general toxicity of the tested compounds. The cytotoxicity of the tested alkaloids was evaluated using the WST-1 metabolic activity assay. The growth of all studied cancer cell lines was inhibited by pancracine (montanine-type alkaloid), with IC50 values which were in the range of 2.20 to 5.15 µM.
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Ingrassia L., Lefranc F., Mathieu V., Darro F., Kiss R. Amaryllidaceae isocarbostyril alkaloids and their derivatives as promising antitumor agents. Transl. Oncol. 2008;1:1–13. doi: 10.1593/tlo.08100. PubMed DOI PMC
Havelek R., Muthna D., Tomsik P., Kralovec K., Seifrtova M., Cahlikova L., Hostalkova A., Safratova M., Perwein M., Cermakova E., et al. Anticancer potential of Amaryllidaceae alkaloids evaluated by screening with a panel of human cells, real-time cellular analysis and Ehrlich tumor-bearing mice. Chem. Biol. Interact. 2017;275:121–132. doi: 10.1016/j.cbi.2017.07.018. PubMed DOI
Nair J.J., van Standen J. Cytotoxicity studies of lycorine alkaloids of the Amaryllidaceae. Nat. Prod. Commun. 2014;9:1193–1210. doi: 10.1177/1934578X1400900834. PubMed DOI
Cho N., Du Y., Valenciano A.L., Fernandez-Murga M.L., Goetz M., Clement J., Cassera M.B., Kingston D.G.I. Antiplasmodial alkaloids from bulbs of Amaryllis belladonna Steud. Bioor. Med. Chem. Lett. 2018;28:40–42. doi: 10.1016/j.bmcl.2017.11.021. PubMed DOI PMC
Zhan G., Zhou J., Liu R., Liu T., Guo G., Wang J., Xiang M., Xue Y., Luo Z., Zhang Y., et al. Galanthamine, plicamine, and secoplicamine alkaloids from Zephyranthes candida and their anti-acetylcholinesterase and antiinflammatory activities. J. Nat. Prod. 2016;79:760–766. doi: 10.1021/acs.jnatprod.5b00681. PubMed DOI
Locarek M., Novakova J., Kloucek P., Hostalkova A., Kokoska L., Gabrlova L., Safratova M., Opletal L., Cahlikova L. Antifugal and antibacterial activity of extracts and alkaloids of selected Amaryllidaceae plant species. Nat. Prod. Commun. 2015;10:1537–1540. PubMed
Hulcova D., Maříkova J., Korabecny J., Hostalkova A., Jun D., Kunes J., Chlebek J., Opletal L., De Simone A., Novakova L., et al. Amaryllidaceae alkaloids from Narcissus pseudonarcissus L. cv. Dutch Master as potential drugs in treatment of Alzheimer’s disease. Phytochemistry. 2019;165:112055. doi: 10.1016/j.phytochem.2019.112055. PubMed DOI
Castillo-Ordonez W.O., Tamarozzi E.R., da Silva G.M., Aristizabal-Pachon A.F., Sakamoto-Hojo E.T., Takahashi C.S., Giuliatti S. Exploration of the acetylcholinesterase inhibitory activity of some alkaloids from Amaryllidaceae family by molecular docking in silico. Neurochem. Res. 2017;42:2826–2830. doi: 10.1007/s11064-017-2295-8. PubMed DOI
Jin Z. Amaryllidaceae and Sceletium alkaloids. Nat. Prod. Rep. 2007;24:886–905. doi: 10.1039/b502163b. PubMed DOI
Safratova M., Hostalkova A., Hulcova D., Breiterova K., Hrabcova V., Machado M., Fontinha D., Prudêncio M., Kunes J., Chlebek J., et al. Alkaloids from Narcissus poeticus cv. Pink Parasol of various structural types and their biological activity. Arch. Pharm. Res. 2018;41:208–218. doi: 10.1007/s12272-017-1000-4. PubMed DOI
Maelicke A., Samochocki M., Jostock R., Fehrenbacher A., Ludwig J., Albuquerque E.X., Zerlin M. Allosteric sensitization of nicotinic receptors by galanthamine, a new treatment strategy for Alzheimer’s disease. Biol. Psychiatry. 2001;49:279–288. doi: 10.1016/S0006-3223(00)01109-4. PubMed DOI
Govindaraju K., Ingels A., Hasan M.N., Sun D., Mathieu V., Masi M., Evidente A., Kornienko A. Synthetic analogues of the montanine-type alkaloids with activity against apoptosis-resistant cancer cells. Bioorg. Med. Chem. Lett. 2018;28:589–593. doi: 10.1016/j.bmcl.2018.01.041. PubMed DOI PMC
Evidente A., Kireev A.S., Jenkins A.R., Romero A.E., Steelant W.F., Van Slambrouck S., Kornienko A. Biological evaluation of structurally diverse Amaryllidaceae alkaloids and their synthetic derivatives: Discovery of novel leads for anticancer drug design. Planta Med. 2009;75:501–507. doi: 10.1055/s-0029-1185340. PubMed DOI PMC
Ingrassia L., Lefranc F., Dewelle J., Pottier L., Mathieu V., Spiegl-Kreinecker S., Sauvage S., El Yazidi M., Dehoux M., Berger W., et al. Structure-activity relationship analysis of novel derivatives of narciclasine (an Amaryllidaceae isocarbostyril derivative) as potential anticancer agents. J. Med. Chem. 2009;52:1100–1114. doi: 10.1021/jm8013585. PubMed DOI
Havelek R., Seifrtova M., Kralovec K., Bruckova L., Cahlikova L., Dalecka M., Vavrova J., Rezacova M., Opletal L., Bilkova Z. The effect of Amaryllidaceae alkaloids haemanthamine and haemanthidine on cell cycle progression and apoptosis in p53-negative human leukemic Jurkat cells. Phytomedicine. 2014;21:479–490. doi: 10.1016/j.phymed.2013.09.005. PubMed DOI
Li L., Zhang Z., Yang Q., Ning M. Lycorine inhibited the cell growth of non-small cell lung cancer by modulating the miR-186/CDK1 axis. Life Sci. 2019;231:116528. doi: 10.1016/j.lfs.2019.06.003. PubMed DOI
Breiterova K., Locarek M., Kohelova E., Talackova M., Hulcova D., Opletal L., Cahlikova L. Daffodils as potential crops of biologically-active compounds: Assessment of 40 ornamental taxa for their alkaloid profile and cholinesterases inhibition activity. Nat. Prod. Commun. 2018;13:419–422. doi: 10.1177/1934578X1801300410. DOI
Kornienko A., Evidente A. Chemistry, biology, and medicinal potential of narciclasine and its congeners. Chem. Rev. 2008;108:1982–2014. doi: 10.1021/cr078198u. PubMed DOI PMC
Hartwell J.L. Plants used against cancer. A survey. Lloydia. 1967;30:379–436.
Kington S. The International Daffodil Register and Classified List. Royal Horticultural Society; London, UK: 2008.
Pettit G.R., Tan R., Bao G.-H., Melody N., Doubek D.L., Gao S., Chapuis J.-C., Williams L. Antineoplastic agents. 587. Isolation and structure of 3-epipancratistatin from Narcissus cv. Ice Follies. J. Nat. Prod. 2012;75:771–773. doi: 10.1021/np200862y. PubMed DOI PMC
Pigni N.B., Ríos-Ruiz S., Martínez-Francés V., Nair J.J., Viladomat F., Codina C., Bastida J. Alkaloids from Narcissus serotinus. J. Nat. Prod. 2012;75:1643–1647. doi: 10.1021/np3003595. PubMed DOI
Huang S., Zhang Y., He H., Li S., Tang G., Chen D., Cao M., Di Y., Hao X.J. A new Amaryllidaceae alkaloid from bulbs of Lycoris radiata. Chin. J. Nat. Med. 2013;11:406–410. doi: 10.3724/SP.J.1009.2013.00406. PubMed DOI PMC
Cowden C.J., Banwell M.G., Ho I.C.S. Synthesis of putative structure of 5,6-dihydrobicolorin. J. Nat. Prod. 1994;57:1746–1750. doi: 10.1021/np50114a023. DOI
Lamoral-Theys D., Andolfi A., Van Goietsenoven G., Cimmino A., Le Calvé B., Wauthoz N., Mégalizzi V., Gras T., Bruyere C., Dubois J., et al. 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. 2009;52:6244–6625. doi: 10.1021/jm901031h. PubMed DOI PMC
Chen J.-Q., Xie J.-H., Bao D.-H., Liu S., Zhou Q.-L. Total synthesis of (−)-galanthamine and (−)-lycoramine via catalytic asymmetric hydrogenation and intramolecular reductive Heck cyclization. Org. Lett. 2012;14:2714–2717. doi: 10.1021/ol300913g. PubMed DOI
Jegorov A., Buchta M., Sedmera P., Kuzma M., Havlicek V. Accurate product ion mass spectra of galanthamine derivatives. J. Mass. Spectrom. 2006;41:544–548. doi: 10.1002/jms.1015. PubMed DOI
Lee T.B.K., Goehring K.E., Ma Z. One-Step conversion of galanthamine to lycoraminone: A novel hydride-transfer reaction. J. Org. Chem. 1998;63:4535–4538. doi: 10.1021/jo980271g. DOI
Berkov S., Reyes-Chilpa R., Codina C., Viladomat F., Bastida J. Revised NMR data for incartine: An alkaloid from Galanthus elwesii. Molecules. 2007;12:1430–1435. doi: 10.3390/12071430. PubMed DOI PMC
Berkov S., Bastida J., Sidjimova B., Viladomat F., Codina C. Phytochemical differentiation of Galanthus nivalis and Galanthus elwesii (Amaryllidaceae): A case study. Biochem. Syst. Ecol. 2008;36:638–645. doi: 10.1016/j.bse.2008.04.002. DOI
Bastida J., Viladomat F., Bergonon S., Fernandez J.M., Codina C., Rubiralta M., Quirion J.-C. Alkaloids from Narcissus leonensis. Phytochemistry. 1993;34:1656–1658. doi: 10.1016/S0031-9422(00)90869-0. DOI
Bastida J., Lavilla R., Viladomat F. The Alkaloids: Chemical and biological aspects of Narcissus alkaloids. In: Cordell G.A., editor. The Alkaloids: Chemistry and Biology. Volume 63. Elsevier; Amsterdam, The Netherlands: 1998. pp. 87–179. PubMed PMC
Jeffs P.W., Abou-Donia A., Campau D. Structures of 9-O-demethylhomolycorine and 5α-hydroxyhomolycorine. alkaloids of Crinum defixum, C. scabrum, and C. latifolium. Assignment of aromatic substitution patterns from 1H-coupled 13C spectra. J. Org. Chem. 1985;50:1732–1737. doi: 10.1021/jo00210a031. DOI
Ghosal S., Ashutosh Razdan S. (+)-Epimaritidine, an alkaloid from Zephyranthes rosea. Phytochemistry. 1985;24:635–637. doi: 10.1016/S0031-9422(00)80796-7. DOI
Berkov S., Sidjimove B., Evstatieva L., Popov S. Intraspecific variability in the alkaloid metabolism of Galanthus elwesii. Phytochemistry. 2004;65:579–586. doi: 10.1016/j.phytochem.2003.12.013. PubMed DOI
Pham L.H., Gründemann E., Wagner J., Bartoszek M., Döpke W. Two novel Amaryllidaceae alkaloids from Hippeastrum equestre Herb.: 3-O-demethyltazettine and egonine. Phytochemistry. 1999;51:327–332. doi: 10.1016/S0031-9422(98)00743-2. DOI
Via J., Arriortura M.I., Ochando L.E., Reventos M.M., Amigo J.M., Bastida J. Structure of eugenine, an alkaloid from Narcissus eugeniae. Acta Cryst. C. 1989;45:2020–2022. doi: 10.1107/S0108270189007973. DOI
Berkov S., Romani S., Herrera M., Viladomat F., Codina C., Momekov G., Ionkova I., Bastida J. Antiproliferative alkaloids from Crinum zeylanicum. Phytother. Res. 2011;25:1686–1692. doi: 10.1002/ptr.3468. PubMed DOI
Bastida J., Llabrés J.M., Viladomat F., Codina C., Rubiralta M., Feliz M. 9-O-Demethylmaritidine: A new alkaloid from Narcissus radinganorum. Planta Med. 1988;54:524–526. doi: 10.1055/s-2006-962537. PubMed DOI
Bao X., Cao Y.-X., Chu W.-D., Qu H., Du J.-Y., Zhao X.-H., Ma X.-Y., Wang C.-T., Fan C.-A. Bioinspired total synthesis of montanine-type Amaryllidaceae alkaloids. Angew. Chem. Int. Edit. 2013;52:14167–14172. doi: 10.1002/anie.201307324. PubMed DOI
Farinon M., Clarimundo V.S., Pedrazza G.P., Gulko P.S., Zuanazzi J.A., Xavier R.M., de Oliveira P.G. Disease modifying anti-rheumatic activity of the alkaloid montanine on experimental arthritis and fibroblast-like synoviocytes. Eur. J. Pharmacol. 2017;15:180–187. doi: 10.1016/j.ejphar.2017.02.013. PubMed DOI
Masi M., van Slambrouck S., Gunawardana S., van Rensburg M.J., James P.C., Mochel J.G., Heliso P.S., Albalawi A.S., Cimmino A., van Otterlo W.A.L., et al. Alkaloids isolated from Haemanthus humilis Jacq., an indigenous South African Amaryllidaceae: Anticancer activity of coccinine and montanine. S. Afr. J. Bot. 2019;126:277–281. doi: 10.1016/j.sajb.2019.01.036. DOI
Havelek R., Siman P., Cmielova J., Stoklasova A., Vavrova J., Vinklarek J., Knizek J., Rezacova M. Differences in vanadocene dichloride and cisplatin effect on MOLT-4 leukemia and human peripheral blood mononuclear cells. Med. Chem. 2012;8:615–621. doi: 10.2174/157340612801216364. PubMed DOI
Undescribed Amaryllidaceae Alkaloids from Zephyranthes citrina and Their Cytotoxicity