Preferences help
enabled [disable] Abstract
Number of results
2010 | 57 | 1 | 75-82
Article title

New method for the study of Amaryllidaceae alkaloid biosynthesis using biotransformation of deuterium-labeled precursor in tissue cultures

Title variants
Languages of publication
Biotransformation of deuterated-4'-O-methylnorbelladine into alkaloids galanthamine and lycorine in tissue cultures of Leucojum aestivum was demonstrated using HPLC coupled to mass spectrometry. GC-MS screening was also carried to investigate other native and deuterated alkaloids. A total of six labeled alkaloids were identified indicating that 4'-O-methyl-d3-norbelladine is incorporated into three different groups of Amaryllidaceae alkaloids that are biosynthesized by three modes of intramolecular oxidative phenol coupling.
Physical description
  • Groupe S.U.C.R.E.S., UMR 7565 CNRS-Nancy-Université, Nancy-Vandoeuvre, France
  • Groupe S.U.C.R.E.S., UMR 7565 CNRS-Nancy-Université, Nancy-Vandoeuvre, France
  • Department of Plant Breeding and Seed Science, Agricultural University, Kraków, Poland
  • Service Commun de Spectrométrie de Masse, UHP-Institut Jean Barriol, Nancy-Vandoeuvre, France
  • Groupe S.U.C.R.E.S., UMR 7565 CNRS-Nancy-Université, Nancy-Vandoeuvre, France
  • Groupe S.U.C.R.E.S., UMR 7565 CNRS-Nancy-Université, Nancy-Vandoeuvre, France
  • Groupe S.U.C.R.E.S., UMR 7565 CNRS-Nancy-Université, Nancy-Vandoeuvre, France
  • Groupe S.U.C.R.E.S., UMR 7565 CNRS-Nancy-Université, Nancy-Vandoeuvre, France
  • Barton DHR, Cohen T (1957) In Festschrift Arthur Stoll; p 117. Birkhäuser, Basel.
  • Barton DHR, Kirby GW, Taylor JB, Thomas GM (1963) Phenol oxidation and biosynthesis. Part VI. The biogenesis of Amaryllidaceae alkaloids. J Chem Soc 4545-4558.
  • Bastida J, Lavilla R, Viladomat F (2006) Chemical and biological aspects of Narcissus alkaloids. In The Alkaloids. Cordell GA, eds, 3: 87-179. Elsevier Inc.
  • Berkov S, Sidjimova B, Evstatieva L, Popov S (2004) Intraspecific variability in the alkaloid metabolism of Galanthus elwesii. Phytochemistry 65: 579-586.
  • Berkov S, Pavlov A, Ilieva M, Burrus M, Popov S, Stanilova M (2005) CGC-MS of alkaloids in Leucojum aestivum plants and their in vitro cultures. Phytochem Anal 16: 98-103.
  • Bernfeld P (1963) In Biogenesis of Natural Compounds; p 985. Pergamon Press Oxford.
  • Bourgaud F, Gravot A, Milesi S, Gontier E (2001) Production of plant secondary metabolites: a historical perspective. Plant Sci 161: 839-851.
  • Cui W, Iwasa K, Sugiura M, Takeuchi A, Tode C, Nishiyama Y, Moriyasu M, Tokuda H, Takeda K (2007) Biotransformation of phenolic 1-benzyl-N-methyltetrahydroisoquinolines in plant cell cultures followed by LC/NMR, LC/MS, and LC/CD. J Nat Prod 70: 1771-1778.
  • Eichhorn J, Takada T, Kita Y, Zenk MH (1998) Biosynthesis of the Amaryllidaceae alkaloid galanthamine. Phytochemistry 49: 1037-1047.
  • Guillou C, Beunard J, Gras E, Thal C (2001) An efficient total synthesis of (±)-galanthamine. Angew Chem Int Ed Engl 40: 4745-4746.
  • Herbert RB (2001) The biosynthesis of plant alkaloids and nitrogenous microbial metabolites. Nat Prod Rep 18: 50-65.
  • Ikezawa N, Iwasa K, Sato F (2007) Molecular cloning and characterization of methylenedioxy bridge-forming enzymes involved in stylopine biosynthesis in Escholzia californica. FEBS J 274: 1019-1035.
  • Iwasa K, Kim CW (1997) Biotransformations of protoberberines in cell cultures of Dicentra spectablis. Phytochemistry 46: 1359-1363.
  • Kornienko A, Evidente A (2008) Chemistry, biology, and medicinal potential of narciclasine and its congeners. Chem Rev 108: 1982-2014.
  • Kreh M, Matusch R, Witte L (1995) Capillary gas chromatography-mass spectrometry of Amaryllidaceae alkaloids. Phytochemistry 38: 773-776.
  • Kukhanova M, Victorova L, Krayevsky A (1983) Peptidyltransferase center of ribosomes: on the mechanism of action of alkaloid lycorine. FEBS Lett 160: 129-133.
  • Le Flem-Bonhomme V, Laurain-Mattar D, Fliniaux MA (2004) Hairy root induction of Papaver somniferum var. album, a difficult-to-transform plant, by A. rhizogenes LBA 9402. Planta 218: 890-893.
  • Marco-Contelles J, Leon R, de Los Rios C, Guglietta A, Terencio J, Lopez MG, Garcia AG, Villarroya M (2006) Novel multipotent tacrine-dihydropyridine hybrids with improved acetylcholinesterase inhibitory and neuroprotective activities as potential drugs for the treatment of Alzheimer's disease. J Med Chem 49: 7607-7610.
  • Markey SP, Powers K, Dubinsky D, Kopin IJ (1980) General method for the synthesis of methyl isotope labeled cathecolamine metabolites. Preparation of 4-hydroxy-3-methoxy-d3-(madelic acid, phenylacetic acid and phenylethylene glycol). J Labelled Comp Radiopharm 17: 103-114.
  • Murashige T, Skoog F (1962) A revised medium for rapid growth and bioassays with tobacco cultures. Physiol Plant 15: 473-497.
  • Ptak A, El Tahchy A, Dupire F, Boisbrun M, Henry M, Chapleur Y, Moś M, Laurain-Mattar D (2009) LCMS and GCMS for the screening of alkaloids in natural and in vitro extracts of Leucojum aestivum. J Nat Prod 72: 142-147.
  • Szewczyk J, Lewin AH, Carroll FI (1988) An improved synthesis of galanthamine. J Heterocyclic Chem 25: 1809-1811.
  • Szlávik L, Gyuris A, Minarovits J, Forgo P, Molnar J, Hohmann J (2004) Alkaloids from Leucojum vernum and antiretroviral activity of Amaryllidaceae alkaloids. Planta Med 70: 871-873.
  • Tram N, Mitova M, Bankova V, Handjieva N, Popov S (2002) GS-MS of Crinum latifolium L. alkaloids. Z Naturforsch C 57: 239-242.
  • Verpoorte R, van der Heijden R, Moreno PRH (1997) Biosynthesis of terpenoid indole alkaloids in Catharanthus roseus cells. In The Alkaloids. Cordell GA, eds, 49: 221-299. Academic Press, San Diego.
  • Verpoorte R, van der Heijden R, ten Hoopen HJG, Memelink J (1999) Metabolic engineering of plant secondary metabolite pathways for the production of fine chemicals. Biotechnol Lett 21: 467-479.
Document Type
Publication order reference
YADDA identifier
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.