Acridone alkaloids

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Acridon, basic structure of the acridon alkaloids
Rue ( Ruta graveolens )

Acridon alkaloids are natural substances that are derived from acridon .

Occurrence

Acridon alkaloids are found in the bark, wood, leaves and roots of the rhombus family , especially in roots and suspension cultures of the rue .

Representative

This group is named after the Acridon . Further representatives are u. a. Acronycin , Melicopicin and Rutacridone :

  • Acronycin

  • Melicopicin

  • Rutacridone

A total of over 270 different acridone alkaloids have been described.

biosynthesis

The biosynthesis of the acridone alkaloids has been intensively researched. Feeding experiments with radionuclide- labeled compounds showed that the synthesis starts from anthranilic acid . This is in a first step with S -Adenosylmethionin N carboxymethylated and then N -Methylanthraniloyl- COA implemented. Catalyzed by the enzyme acridone synthase, the compound reacts with 3 molecules of malonyl-CoA and subsequent ring closure to form a 2-aminobenzophenone derivative as an intermediate. This is finally cyclized to 1,3-dihydroxy-10-methylacridone.

Biosynthesis of an acridone derivative

1,3-Dihydroxy-10-methylacridone and, to a lesser extent, 1,3-dihydroxyacridone, in turn, serve as starting products for almost all more complex acridone alkaloids.

properties

Many acridon alkaloids are methylated on the nitrogen atom and also have two oxygen functions, which can be free, alkylated or bound in rings. Acridon alkaloids show a blue-green fluorescence, so that they can be detected with the help of UV light. Some alkaloids in this group are effective against malaria pathogens. Acronycin also inhibits cell division.

Individual evidence

  1. ↑ a b c d Entry on Acridone. In: Römpp Online . Georg Thieme Verlag, accessed on April 21, 2020.
  2. ↑ a b R. Hansel, O. Sticher: Pharmakognosie Phytopharmazie . 8th edition. Springer Medizin Verlag, Heidelberg 2007, ISBN 978-3-540-26508-5 , p. 101.1326 .
  3. ↑ Acridone alkaloid biosynthesis. Retrieved April 22, 2020 (English).
  4. ↑ Joseph P. Michael: Acridone Alkaloids . In: The Alkaloids: Chemistry and Biology . tape 78 , 2017, chap. 1 , doi : 10.1016 / bs.alkal.2017.06.001 (English).
  5. ↑ a b Alexios Leandros Skaltsounis, Sofia Mitaku, François Tillequin: Acridone alkaloids . In: The Alkaloids: Chemistry and Biology . tape 54 , 2000, pp. 259 , doi : 10.1016 / S0099-9598 (00) 54004-8 (English).
  6. ↑ D. Gröger and S. Johne: On the biosynthesis of some alkaloids from Glycosmis arborea (Rutaceae) . In: Journal for Nature Research . 23B, 1968, pp. 1072-1075 ( mpg.de [PDF]).
  7. ↑ RH Prague, HM Thredgold: Studies using radioisotopes. III. The biosynthesis of acridone alkaloid . In: Australian Journal of Chemistry . tape 22 , no. 12 , 1969, p. 2627 , doi : 10.1071 / CH9692627 (English).
  8. ↑ A. Baumert, I. Kuzovkina, M. Hieke, D. Gröger: Biosynthesis of Rutacridone: The N-Methylation Step . In: Planta Medica . tape 48 , no. 07 July 1983, p. 142 , doi : 10.1055 / s-2007-969909 (English).
  9. ↑ A. Baumert, M. Hieke, D. Gröger: N-Methylation of Anthranilic Acid to N-Methylanthranilic Acid by Cell-free Extracts of Tissue Cultures . In: Planta Medica . tape 48 , no. 08 August 1983, p. 258 , doi : 10.1055 / s-2007-969929 (English).
  10. ^ Alfred Baumert, Andrea Porzel, Jürgen Schmidt, Detlef Gröger: Formation of 1,3-Dihydroxy-N-methylacridone from N-Methylanthraniloyl-CoA and Malonyl-CoA by Cell-Free Extracts of Ruta graveolens . In: Journal for Nature Research . 47C, 1992, pp. 365-368 (English, mpg.de [PDF]).
  11. ^ Walter Maier, Alfred Baumert, Brigitte Schumann, Hiroshi Furukawa, Detlef Gröger: Synthesis of 1,3-dihydroxy-N-methylacridone and its conversion to rutacridone by cell-free extracts of Ruta graveolens cell cultures . In: Phytochemistry . tape 32 , no. 3 , February 1993, p. 691 , doi : 10.1016 / S0031-9422 (00) 95155-0 (English).
  12. ^ Alfred Baumert, Walter Maier, Detlef Gröger: Purification and Properties of Acridone Synthase from Cell Suspension Cultures of Ruta gvaveolens L. In: Zeitschrift für Naturforschung . 49C, 1994, pp. 26–32 (English, mpg.de [PDF]).
  13. ↑ A. Baumert, D. Gröger: Synthesis of 1,3-dihydroxy-N-methylacridone by cell-free extracts of cell suspension cultures . In: FEBS Letters . tape 187 , no. 2 , August 5, 1985, pp. 311 , doi : 10.1016 / 0014-5793 (85) 81266-7 (English).
  14. ↑ A. Baumert, G. Schneider, and D. Gröger: Biosynthesis of Acridone Alkaloids. A Cell-Free System from Ruta graveolens Cell Suspension Cultures . In: Journal for Nature Research . 41C, 1986, pp. 187–192 (English, mpg.de [PDF]).

Web links

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