Aristolochic acids

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Aristolochic acid I / A, from which the other representatives of the substance group are derived

Aristolochic acid are phytochemicals , in a variety of species of the genera Aristolochia ( Aristolochia ), Asarum ( subungulates ) Saruma and Thottea , all the family of Aristolochiaceae ( aristolochiaceae were properly) detected. Biogenetically, they are derived from aporphine alkaloids , as shown by the structural similarity with z. B. the aporphine alkaloids apomorphine or bulbocapnine can be recognized. The relatively rare nitro group in natural productsarises from oxidation of the nitrogen atom in the former piperidine ring .

Representative

Various derivatives with the same basic structure are called aristolochic acids . The three radicals (R 1 , R 2 and R 3 ) can be hydrogen , hydroxy or methoxy groups . The most important representative is aristolochic acid I.

Aristolochic acids
Surname Aristolochic Acid I. Aristolochic acid Ia Aristolochic acid II Aristolochic acid III Aristolochic acid IVa Aristolochic Acid IV Aristolochic acid E.
other names Aristolochic Acid A. Aristolochic acid B Aristolochic acid C Aristolochic acid D.
Structural formula Basic structure
R 1 -H -H -H -OH -OH -OCH 3 -H
R 2 -H -H -H -H -H -H -OCH 3
R 3 -OCH 3 -OH -H -H -OCH 3 -OCH 3 -OH
CAS number 313-67-7 38965-71-8 475-80-9 4849-90-5 17413-38-6 15918-62-4 107259-48-3
PubChem 2236 148297 108168 165274 161218 167493 147113
Molecular formula C 17 H 11 NO 7 C 16 H 9 NO 7 C 16 H 9 NO 6 C 16 H 9 NO 7 C 17 H 11 NO 8 C 18 H 13 NO 8 C 17 H 11 NO 8
Molar mass 341.27 g mol −1 327.25 g mol −1 311.25 g mol −1 327.25 g mol −1 357.27 g mol −1 371.30 g mol −1 357.27 g mol −1
Physical state firmly
Brief description yellow powder
Melting point 269-270 ° C
solubility soluble in DMSO and ethanol
GHS
labeling
06 - Toxic or very toxic
danger
H and P phrases 301
no EUH phrases
301 + 310
Toxicological data 190 mg kg −1 ( LD 50 ,  rat ,  oral , mixture of I, II and III)

Occurrence

Easter luzei ( Aristolochia clematitis )

The occurrence of aristolochic acids outside of the Aristolochiaceae family has not been documented in plants. The roots of the easter egg ( Aristolochia clematitis ) contain up to one percent aristolochic acids, while the content in the leaves is below 0.1%.

use

Various aristolochic acids used to be contained in some common slimming products , especially those derived from Chinese medicine , and in the strengthening tonic Frauengold . The preparation Tardolyt ® contained aristolochic acid as sodium salt and was used as a phagocytosis activator in infections .

toxicology

Aristolochic acids have a high toxic potential. The compounds were found to be genotoxic in in-vitro and in-vivo tests and were also carcinogenic in animal experiments . They also have a nephrotoxic (kidney-damaging) effect . The Balkan nephropathy is endemic in some regions of the Balkan occurring chronic toxic kidney disease, which is mainly caused by aristolochic acid.

The biochemical mechanism of the mutagenicity of the aristolochic acids is based on a transversion of AT nucleotide pairs according to TA at different locations in the genome.

In Germany, based on a step- by- step plan procedure (dated June 3, 1981), all " aristolochic acid-containing human and veterinary medicinal products, including phytotherapeutic and homeopathic medicines that are manufactured using plants containing aristolochic acid " are considered questionable. Placing on the market is therefore prohibited according to Section 5 AMG . The order also affects the sale of the corresponding medicinal drugs themselves. However, the phased plan procedure does not include homeopathic medicinal products containing preparations of plants of the genera Aristolochia and Asarum from potency level D11 - based on the finished medicinal product .

Others

The caterpillars of some butterfly genera from the knight butterfly family (Papilionidae) have specialized in plant species from the genera mentioned above. They are immune to the toxins they contain and become poisonous when consumed, which provides a degree of protection against predators.

Individual evidence

  1. ^ Hesse, Alkaloidchemie, Georg Thieme Verlag 1978, ISBN 3-13-381801-5 .
  2. ^ PubChem : Aristolochic Acids
  3. ↑ Entry on aristolochic acids. In: Römpp Online . Georg Thieme Verlag, accessed on May 21, 2014.
  4. ↑ a b c Data sheet Aristolochic acid I from Sigma-Aldrich , accessed on February 8, 2010 ( PDF ). .
  5. ↑ Data sheet Aristolochic acid I from Sigma-Aldrich , accessed on April 26, 2011 ( PDF ).
  6. ↑ gift plants.com: Easter luzei (Aristolochia clematitis)
  7. ↑ Red List 1969, Federal Association of the Pharmaceutical Industry e. V. (Ed.), Editio Cantor Verlag Aulendorf.
  8. ↑ Arthur P. Grollman, Shinya Shibutani, Masaaki Moriya et al .: Aristolochic acid and the etiology of endemic (Balkan) nephropathy . In: Proceedings of the National Academy of Sciences . tape 104 , no. 29 , July 17, 2007, pp. 12129-12134 , doi : 10.1073 / pnas.0701248104 .
  9. ↑ ML Hoang, C.-H. Chen et al. a .: Mutational Signature of Aristolochic Acid Exposure as Revealed by Whole-Exome Sequencing. In: Science Translational Medicine. 5, 2013, pp. 197ra102-197ra102, doi: 10.1126 / scitranslmed.3006200 .
  10. ↑ JV Euw, T. Reichstein, Miriam Rothschild: Aristolochic Acid-I in the Swallowtail Butterfly (Fabr.) (Papilionidae). In: Israel Journal of Chemistry . 6, 1968, p. 659, doi: 10.1002 / ijch.196800084 .

literature