Crossref Cited-by Linking logo

Collect. Czech. Chem. Commun. 1990, 55, 2840-2873
https://doi.org/10.1135/cccc19902840

Quaternary benzo[c]phenanthridine alkaloids

Jiří Dostála and Milan Potáčekb

a Department of Medical Chemistry and Biochemistry, Faculty of Medicine, Masaryk University, Komenského nam. 2, 662 43 Brno
b Department of Organic Chemistry, Faculty of Sciences, Masaryk University, Kotlářská 2, 611 37 Brno

Crossref Cited-by Linking

  • Marasco Daniela, Vicidomini Caterina, Krupa Pawel, Cioffi Federica, Huy Pham Dinh Quoc, Li Mai Suan, Florio Daniele, Broersen Kerensa, De Pandis Maria Francesca, Roviello Giovanni N.: Plant isoquinoline alkaloids as potential neurodrugs: A comparative study of the effects of benzo[c]phenanthridine and berberine-based compounds on β-amyloid aggregation. Chemico-Biological Interactions 2021, 334, 109300. <https://doi.org/10.1016/j.cbi.2020.109300>
  • Sett Riya, Sen Swagata, Paul Bijan K., Guchhait Nikhil: Effect of temperature and salts on niosome-bound anti-cancer drug along with disruptive influence of cyclodextrins. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2020, 234, 118261. <https://doi.org/10.1016/j.saa.2020.118261>
  • Lin Li, Liu Yan‐Chun, Huang Jia‐Lu, Liu Xiu‐Bin, Qing Zhi‐Xing, Zeng Jian‐Guo, Liu Zhao‐Ying: Medicinal plants of the genus Macleaya (Macleaya cordata, Macleaya microcarpa): A review of their phytochemistry, pharmacology, and toxicology. Phytotherapy Research 2018, 32, 19. <https://doi.org/10.1002/ptr.5952>
  • Lv Pei, Chen Yiliang, Shi Taozhong, Wu Xiangwei, Li Qing X., Hua Rimao: Synthesis and fungicidal activities of sanguinarine derivatives. Pesticide Biochemistry and Physiology 2018, 147, 3. <https://doi.org/10.1016/j.pestbp.2017.06.009>
  • Chen Han-bin, Luo Chao-dan, Liang Jia-li, Zhang Zhen-biao, Lin Guo-sheng, Wu Jia-zhen, Li Cai-lan, Tan Li-hua, Yang Xiao-bo, Su Zi-ren, Xie Jian-hui, Zeng Hui-fang: Anti-inflammatory activity of coptisine free base in mice through inhibition of NF-κB and MAPK signaling pathways. European Journal of Pharmacology 2017, 811, 222. <https://doi.org/10.1016/j.ejphar.2017.06.027>
  • Hošek Jan, Šebrlová Kristýna, Kaucká Petra, Peš Ondřej, Táborská Eva: The capability of minor quaternary benzophenanthridine alkaloids to inhibit TNF-α secretion and cyclooxygenase activity. Acta Vet. Brno 2017, 86, 223. <https://doi.org/10.2754/avb201786030223>
  • Hibino Satoshi: Synthetic Studies of Bioactive Heterocyclic Natural Products and Fused Heterocyclic Compounds Based on the Thermal Electrocyclic or Azaelectocyclic Reaction of 6π-Electron or Aza-6π-electron Systems. YAKUGAKU ZASSHI 2016, 136, 607. <https://doi.org/10.1248/yakushi.15-00273>
  • Satpathi Sagar, Gavvala Krishna, Hazra Partha: Fluorescence switching of sanguinarine in micellar environments. Phys. Chem. Chem. Phys. 2015, 17, 20725. <https://doi.org/10.1039/C5CP02818C>
  • Rájecký Michal, Šebrlová Kristýna, Mravec Filip, Táborský Petr, Tajmir-Riahi Heidar-Ali: Influence of Solvent Polarity and DNA-Binding on Spectral Properties of Quaternary Benzo[c]phenanthridine Alkaloids. PLoS ONE 2015, 10, e0129925. <https://doi.org/10.1371/journal.pone.0129925>
  • Choshi Tominari, Hibino Satoshi, Kurata Yuhki, Ishihara Yuhsuke, Hatae Noriyuki, Nishiyama Takashi: Total Synthesis of the Benzo[c]phenanthridine Alkaloids, Terihanine and Isoterihanine, and Their Antitumor Activity. HETEROCYCLES 2014, 88, 297. <https://doi.org/10.3987/COM-13-S(S)16>
  • Kadam Shivaji S., Maier Lukáš, Šolomek Tomáš, Nečas Marek, Šmejkal Karel, Dostál Jiří, Sklenář Vladimír, Marek Radek: Structure and NMR properties of 6‐substituted‐5,6‐dihydrobenzo[c]phenanthridine alkaloids. J of Physical Organic Chem 2013, 26, 814. <https://doi.org/10.1002/poc.3175>
  • Zhang Hua‐Hai, Wu Yong, Sun Zhi‐Liang, Liu Zhao‐Ying: Identification of sanguinarine metabolites in pig liver preparations by accurate mass measurements using electrospray ionization hybrid ion trap/time‐of‐flight mass spectrometry. Rapid Comm Mass Spectrometry 2013, 27, 979. <https://doi.org/10.1002/rcm.6538>
  • Vacek Jan, Papoušková Barbora, Kosina Pavel, Galandáková Adéla, Ulrichová Jitka: Mass spectrometric investigation of chelerythrine and dihydrochelerythrine biotransformation patterns in human hepatocytes. Journal of Chromatography B 2013, 941, 17. <https://doi.org/10.1016/j.jchromb.2013.09.037>
  • Rajecky Michal, Slaninova Iva, Mokrisova Petra, Urbanova Jana, Palkovsky Martin, Taborska Eva, Taborsky Petr: Alkaloid chelirubine and DNA: Blue and red luminescence. Talanta 2013, 105, 317. <https://doi.org/10.1016/j.talanta.2012.10.045>
  • Stýskala Jakub, Hlaváč Jan, Cankař Petr: Synthesis of oxidative dihydroxy metabolites of benzo[c]phenanthridines. Tetrahedron 2013, 69, 4670. <https://doi.org/10.1016/j.tet.2013.03.105>
  • Kumazawa Eri, Tokuhashi Takashi, Horibata Akiyoshi, Kurono Nobuhito, Senboku Hisanori, Tokuda Masao, Ohkuma Takashi, Orito Kazuhiko: Synthesis of Benzo[c]phenanthridine Alkaloids by Pd(OAc)2‐Induced Direct Aromatic Carbonylation. Eur J Org Chem 2012, 2012, 4622. <https://doi.org/10.1002/ejoc.201200262>
  • Pěnčíková K., Kollár P., Müller Závalová V., Táborská E., Urbanová J., Hošek J.: Investigation of sanguinarine and chelerythrine effects on LPS-induced inflammatory gene expression in THP-1 cell line. Phytomedicine 2012, 19, 890. <https://doi.org/10.1016/j.phymed.2012.04.001>
  • Weerasinghe Priya, Buja L. Maximilian: Oncosis: An important non-apoptotic mode of cell death. Experimental and Molecular Pathology 2012. <https://doi.org/10.1016/j.yexmp.2012.09.018>
  • Vacek Jan, Vrublová Eva, Kubala Martin, Janovská Marika, Fojta Miroslav, Šimková Eva, Stýskala Jakub, Skopalová Jana, Hrbáč Jan, Ulrichová Jitka: Oxidation of Sanguinarine and Its Dihydro‐Derivative at a Pyrolytic Graphite Electrode Using Ex Situ Voltammetry. Study of the Interactions of the Alkaloids with DNA. Electroanalysis 2011, 23, 1671. <https://doi.org/10.1002/elan.201100028>
  • Kosina Pavel, Vacek Jan, Papoušková Barbora, Stiborová Marie, Stýskala Jakub, Cankař Petr, Vrublová Eva, Vostálová Jitka, Šimánek Vilím, Ulrichová Jitka: Identification of benzo[c]phenanthridine metabolites in human hepatocytes by liquid chromatography with electrospray ion-trap and quadrupole time-of-flight mass spectrometry. Journal of Chromatography B 2011, 879, 1077. <https://doi.org/10.1016/j.jchromb.2011.03.023>
  • Ishihara Yuhsuke, Azuma Shuhei, Choshi Tominari, Kohno Kakujirou, Ono Kanako, Tsutsumi Hiroyuki, Ishizu Takashi, Hibino Satoshi: Total synthesis of benzo[c]phenanthridine alkaloids based on a microwave-assisted electrocyclic reaction of the aza 6π-electron system and structural revision of broussonpapyrine. Tetrahedron 2011, 67, 1320. <https://doi.org/10.1016/j.tet.2010.11.066>
  • Miskolczy Zsombor, Megyesi Mónika, Tárkányi Gábor, Mizsei Réka, Biczók László: Inclusion complex formation of sanguinarinealkaloid with cucurbit[7]uril: inhibition of nucleophilic attack and photooxidation. Org. Biomol. Chem. 2011, 9, 1061. <https://doi.org/10.1039/C0OB00666A>
  • Kerry Mark A, Duval Olivier, Waigh Roger D, Mackay Simon P: The Role of the Iminium Bond in the Inhibition of Reverse Transcriptase by Quaternary Benzophenanthridines. Journal of Pharmacy and Pharmacology 2011, 50, 1307. <https://doi.org/10.1111/j.2042-7158.1998.tb03350.x>
  • Hibino Satoshi, Choshi Tominari: Synthetic Studies on Nitrogen-Containing Fused-Heterocyclic Compounds Based on Thermal Electrocyclic Reactions of 6π-Electron and Aza 6π-Electron Systems. HETEROCYCLES 2011, 83, 1205. <https://doi.org/10.3987/REV-10-691>
  • Li Chang-Feng, Du Li-Ming, Zhang Hui-Ming: Study on the inclusion interaction of cucurbit[n]urils with sanguinarine by spectrofluorimetry and its analytical application. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2010, 75, 912. <https://doi.org/10.1016/j.saa.2009.12.036>
  • Pyrko A. N.: Synthesis of new benzo[c]phenanthridine derivatives. Russ J Org Chem 2010, 46, 1843. <https://doi.org/10.1134/S1070428010120134>
  • Kohno Kakujiro, Azuma Shuhei, Choshi Tominari, Nobuhiro Junko, Hibino Satoshi: A new synthesis of the benzo[c]phenanthridines nornitidine, noravicine, and isodecarine, based on a microwave-assisted electrocyclic reaction of the aza 6π-electron system. Tetrahedron Letters 2009, 50, 590. <https://doi.org/10.1016/j.tetlet.2008.11.076>
  • Reddy Naveen P., Das Mukul: Interaction of Sanguinarine Alkaloid, Isolated From Argemone Oil, With Hepatic Cytochrome P450 in Rats. Toxicology Mechanisms and Methods 2008, 18, 635. <https://doi.org/10.1080/15376510701738439>
  • Jančula Daniel, Suchomelová Jana, Gregor Jakub, Smutná Marie, Maršálek Blahoslav, Táborská Eva: Effects of aqueous extracts from five species of the family Papaveraceae on selected aquatic organisms. Environmental Toxicology 2007, 22, 480. <https://doi.org/10.1002/tox.20290>
  • Hallock Sarathi, Tang Shou-Ching, Buja L. Maximilian, Trump Benjamin F., Liepins Andrejs, Weerasinghe Priya: Aurintricarboxylic Acid Inhibits Protein Synthesis Independent, Sanguinarine-Induced Apoptosis and Oncosis. Toxicol Pathol 2007, 35, 300. <https://doi.org/10.1080/01926230701194211>
  • Slaninová Iva, Slunská Zdenka, Šinkora Jiří, Vlková Marcela, Táborská Eva: Screening of Minor Benzo(c.)phenanthridine Alkaloids for Antiproliferative and Apoptotic Activities. Pharmaceutical Biology 2007, 45, 131. <https://doi.org/10.1080/13880200601113099>
  • Weerasinghe Priya, Hallock Sarathi, Tang Shou-Ching, Trump Benjamin, Liepins Andrejs: Sanguinarine overcomes P-glycoprotein-mediated multidrug-resistance via induction of apoptosis and oncosis in CEM-VLB 1000 cells. Experimental and Toxicologic Pathology 2006, 58, 21. <https://doi.org/10.1016/j.etp.2006.01.008>
  • Vespalec Radim, Vlčková Markéta, Kubáň Vlastimil: Effects of the limited analyte solubility on its mobility and zone shape: Electrophoretic behavior of sanguinarine and chelerythrine around pH 7. Electrophoresis 2005, 26, 3265. <https://doi.org/10.1002/elps.200500344>
  • Harayama Takashi: Synthesis of Benzo[c]phenanthridine Alkaloids Using a Palladium-catalyzed Aryl-Aryl Coupling Reaction. HETEROCYCLES 2005, 65, 697. <https://doi.org/10.3987/REV-04-594>
  • Vlčková Markéta, Barták Petr, Kubáň Vlastimil: Capillary electrophoretic studies of acid–base properties of sanguinarine and chelerythrine alkaloids. Journal of Chromatography A 2004, 1040, 141. <https://doi.org/10.1016/j.chroma.2004.03.064>
  • Vespalec R., Vlčková M., Horáková H.: Aggregation and other intermolecular interactions of biological buffers observed by capillary electrophoresis and UV photometry. Journal of Chromatography A 2004, 1051, 75. <https://doi.org/10.1016/j.chroma.2004.05.051>
  • Barták Petr, Šimánek Vilím, Vlčková Markéta, Ulrichová Jitka, Vespalec Radim: Interactions of sanguinarine and chelerythrine with molecules containing a mercapto group. J of Physical Organic Chem 2003, 16, 803. <https://doi.org/10.1002/poc.659>
  • Vespalec Radim, Barták Petr, Šimánek Vilı́m, Vlčková Markéta: Electrophoretic investigation of interactions of sanguinarine and chelerythrine with molecules containing mercapto group. Journal of Chromatography B 2003, 797, 357. <https://doi.org/10.1016/S1570-0232(03)00308-8>
  • Sečkářová Pavlína, Marek Radek, Dostál Jiří, Dommisse Roger, Esmans Eddy L.: Structural studies of benzophenanthridine alkaloid free bases by NMR spectroscopy. Magnetic Reson in Chemistry 2002, 40, 147. <https://doi.org/10.1002/mrc.979>
  • Šedo Aleksi, Vlašicová Květoslava, Barták Petr, Vespalec Radim, Vičar Jaroslav, Šimánek Vilim, Ulrichová Jitka: Quaternary benzo[c]phenanthridine alkaloids as inhibitors of aminopeptidase N and dipeptidyl peptidase IV. Phytotherapy Research 2002, 16, 84. <https://doi.org/10.1002/ptr.969>
  • Toušek Jaromı́r, Dommisse Roger, Dostál Jiřı́, Žák Zdirad, Pieters Luc, Marek Radek: Configurations and conformations of sanguinarine and chelerythrine free bases stereoisomers. Journal of Molecular Structure 2002, 613, 103. <https://doi.org/10.1016/S0022-2860(02)00138-2>
  • Ishikawa Tsutomu: Benzo[c]phenanthridine bases and their antituberculosis activity. Med Res Rev 2001, 21, 61. <https://doi.org/10.1002/1098-1128(200101)21:1<61::AID-MED2>3.0.CO;2-F>
  • Ishikawa Tsutomu: Benzo[c]phenanthridine bases and their antituberculosis activity. Med. Res. Rev. 2001, 21, 61. <https://doi.org/10.1002/1098-1128(200101)21:1<61::AID-MED2>3.0.CO;2-F>
  • Fleury Fabrice, Sukhanova Alyona, Ianoul Anatoli, Devy Jerome, Kudelina Irina, Duval Olivier, Alix Alain J.P., Jardillier Jean Claude, Nabiev Igor: Molecular Determinants of Site-specific Inhibition of Human DNA Topoisomerase I by Fagaronine and Ethoxidine. Journal of Biological Chemistry 2000, 275, 3501. <https://doi.org/10.1074/jbc.275.5.3501>
  • Dostál Jirí, Slavík Jirí, Potácek Milan, Marek Radek, Sklenár Vladimír, De Hoffmann Edmond, Rozenberg Raoul, Tinant Bernard, Declercq Jean-Paul: Structure and transformations of the alkaloid sanguilutine. Phytochemistry 1998, 47, 879. <https://doi.org/10.1016/S0031-9422(97)00665-1>
  • Geen Graham R., Mann Inderjit S., Valerie Mullane M., McKillop Alexander: A versatile synthesis of fully aromatic benzo[c]phenanthridine alkaloids. Tetrahedron 1998, 54, 9875. <https://doi.org/10.1016/S0040-4020(98)00540-7>
  • Marek Radek, Sklenár Vladimír, Dostál Jiří, Slavík Jiří: Determination of a symmetrical dimer structure in benzo[c]phenanthridine alkaloids by pulsed-field-gradient HMBC. Tetrahedron Letters 1996, 37, 1655. <https://doi.org/10.1016/0040-4039(96)00084-6>
  • Dostál Jiří, Bochořáková Hana, Táborská Eva, Slavík Jiří, Potáček Milan, Buděšínský Miloš, de Hoffmann Edmond: Structure of Sanguinarine Base. J. Nat. Prod. 1996, 59, 599. <https://doi.org/10.1021/np960356h>
  • Krivjanský Viktor, Obernauerová Margita, Ulrichová Jitka, Å imánek Vilém, Å ubík Július: Induction of respiration-deficient mutants inSaccharomyces cerevisiaeby chelerythrine. FEMS Microbiology Letters 1994, 120, 87. <https://doi.org/10.1111/j.1574-6968.1994.tb07012.x>
  • Bentley K. W.: β-Phenylethylamines and the isoquinoline alkaloids. Nat. Prod. Rep. 1992, 9, 365. <https://doi.org/10.1039/NP9920900365>
  • DOSTAL J., POTACEK M.: ChemInform Abstract: Quaternary Benzo(c)phenanthridine Alkaloids. ChemInform 1991, 22. <https://doi.org/10.1002/chin.199113355>