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Pure Appl. Chem., 1994, Vol. 66, No. 10-11, pp. 2023-2028

The formation of benzophenanthridine alkaloids

M. H. Zenk

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  • Qing Zhi-Xing, Cheng Pi, Liu Xiu-Bin, Liu Yi-Song, Zeng Jian-Guo, Wang Wei: Structural speculation and identification of alkaloids in Macleaya cordata fruits by high-performance liquid chromatography/quadrupole-time-of-flight mass spectrometry combined with a screening procedure. Rapid Commun. Mass Spectrom. 2014, 28, 1033. <>
  • Schütz Ingeborg, Moritz Gerald B., Roos Werner: Alkaloid metabolism in thrips-Papaveraceae interaction: Recognition and mutual response. Journal of Plant Physiology 2014, 171, 119. <>
  • Takemura Tomoya, Ikezawa Nobuhiro, Iwasa Kinuko, Sato Fumihiko: Molecular cloning and characterization of a cytochrome P450 in sanguinarine biosynthesis from Eschscholzia californica cells. Phytochemistry 2013, 91, 100. <>
  • Hagel J. M., Facchini P. J.: Benzylisoquinoline Alkaloid Metabolism: A Century of Discovery and a Brave New World. Plant and Cell Physiology 2013, 54, 647. <>
  • Gathungu Rose M., Oldham John T., Bird Susan S., Lee-Parsons Carolyn W. T., Vouros Paul, Kautz Roger: Application of an integrated LC-UV-MS-NMR platform to the identification of secondary metabolites from cell cultures: benzophenanthridine alkaloids from elicited Eschscholzia californica (california poppy) cell cultures. Anal. Methods 2012, 4, 1315. <>
  • Panjikar Santosh, Stoeckigt Joachim, O'Connor Sarah, Warzecha Heribert: The impact of structural biology on alkaloid biosynthesis research. Nat. Prod. Rep. 2012, 29, 1176. <>
  • ZENK M. H.: ChemInform Abstract: The Formation of Benzophenanthridine Alkaloids. ChemInform 2010, 26, no. <>
  • Vrublová Eva, Ulrichová Jitka, Šimánek Vilím, Fojta Miroslav, Vacek Jan: Oxidation of Protopine at a Pyrolytic Graphite Electrode Using Cyclic and Square-Wave Voltammetry. Electroanalysis (N Y ) 2010, 22, 2879. <>
  • Angelova S., Buchheim M., Frowitter D., Schierhorn A., Roos W.: Overproduction of Alkaloid Phytoalexins in California Poppy Cells Is Associated with the Co-Expression of Biosynthetic and Stress-Protective Enzymes. MOL PLANT 2010, 3, 927. <>
  • Vacek Jan, Walterová Daniela, Vrublová Eva, Šimánek Vilím: The Chemical and Biological Properties of Protopine and Allocryptopine. HETEROCYCLES 2010, 81, 1773. <>
  • Ikezawa Nobuhiro, Iwasa Kinuko, Sato Fumihiko: CYP719A subfamily of cytochrome P450 oxygenases and isoquinoline alkaloid biosynthesis in Eschscholzia californica . Plant Cell Rep 2009, 28, 123. <>
  • Slaninová Iva, Slanina Jiří, Táborská Eva: Quaternary benzo[c]phenanthridine alkaloids—novel cell permeant and red fluorescing DNA probes. Cytometry 2007, 71a, 700. <>
  • Cui Wenhua, Iwasa Kinuko, Sugiura Makiko, Takeuchi Atsuko, Tode Chisato, Nishiyama Yumi, Moriyasu Masataka, Tokuda Harukuni, Takeda Kazuyoshi: Biotransformation of Phenolic 1-Benzyl-N-methyltetrahydroisoquinolines in Plant Cell Cultures Followed by LC/NMR, LC/MS, and LC/CD. J. Nat. Prod. 2007, 70, 1771. <>
  • Ikezawa Nobuhiro, Iwasa Kinuko, Sato Fumihiko: Molecular cloning and characterization of methylenedioxy bridge-forming enzymes involved in stylopine biosynthesis in Eschscholzia californica : Stylopine synthase from Eschscholzia californica. FEBS J 2007, 274, 1019. <>
  • Iwasa Kinuko, Kuribayashi Ayako, Sugiura Makiko, Moriyasu Masataka, Lee Dong-Ung, Wiegrebe Wolfgang: LC–NMR and LC–MS analysis of 2,3,10,11-oxygenated protoberberine metabolites in Corydalis cell cultures. Phytochemisry 2003, 64, 1229. <>
  • Lee Jintae, Pedersen Henrik: Stable Genetic Transformation of Eschscholzia Californica Expressing Synthetic Green Fluorescent Proteins. Biotechnol Progress 2001, 17, 247. <>
  • Sotomayor Nuria, Domínguez Esther, Lete Esther: Isoquinoline formation via iminium ions cyclization: A direct approach to c-2′ functionalized 3-aryltetrahydroisoquinolines. Tetrahedron 1995, 51, 12159. <>