Persin

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Structural formula
Structure of persin
General
Surname Persin
other names

(12 Z , 15 Z ) -2-Hydroxy-4-oxo-12,15-henicosadien-1-yl-acetate

Molecular formula C 23 H 40 O 4
External identifiers / databases
CAS number
  • 60640-59-7 [( S ) form]
  • 56164-07-9 8 [( R ) -form]
PubChem 5283266
ChemSpider 4446387
Wikidata Q633921
properties
Molar mass 380.6 g mol −1
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Persin is an acetogenin , a toxin from the group of polyketides , a fatty acid derivative that is contained, for example, in the leaves of the avocado ( Persea americana ). The common name is also derived from the generic name Persea of the avocado.

It is considered to be harmless to humans, while it is poisonous to almost all domestic animals (horses, sheep, goats, rabbits, pet birds , ostriches , poultry) and fish. General symptoms of persine poisoning are shortness of breath, palpitations, cyanosis , edema, vomiting, and colic.

Avocado leaves

In human medicine, on the other hand, it is intensively studied in breast cancer research due to its breast cell-specific effect .

In mice, non-fatal damage to the mammary gland tissue was described at 60 to 100 mg / kg and necrosis of myocardial tissue at 100 mg / kg persin.

The lethal dose is not yet known, the effect varies depending on the species. Lethal doses of around 200 mg / kg body weight have been described for mice.

Individual evidence

  1. ↑ Shmuel Yannai: Dictionary of Food Compounds. Chapman & Hall, 2004, ISBN 1-58488-416-9 , p. 324.
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ↑ Tam Garland, A. Catherine Barr: Toxic Plants and Other Natural Toxicants. CABI, 1998, 1999, ISBN 0-85199-263-3 , pp. 86-89.
  4. ^ Gerhard Habermehl and Petra Zimmer: Poison Plants and Intoxications. M. & H. Schaper, 2009, ISBN 978-3-7944-0208-3 , pp. 71, 172-173.
  5. ↑ Persea americana - Toxins on vetpharm.uzh.ch, accessed on November 20, 2017.
  6. ↑ Persea americana - Veterinary toxicology on vetpharm.uzh.ch, accessed on December 28, 2017.
  7. ↑ CG Roberts, E. Gurisik, TJ Biden, RL Sutherland, AJ Butt: Synergistic cytotoxicity between tamoxifen and the plant toxin persin in human breast cancer cells is dependent on Bim expression and mediated by modulation of ceramide metabolism . In: Molecular Cancer Therapeutics . 6, No. 10, 2007, pp. 2777-85. doi : 10.1158 / 1535-7163.MCT-07-0374 . PMID 17913853 .
  8. ↑ a b P. B. Oelrichs, JC Ng, AA Seawright, A. Ward, L. Schäffeler, JK MacLeod: Isolation and identification of a compound from avocado ( Persea americana ) leaves which causes necrosis of the acinar epithelium of the lactating mammary gland and the myocardium . In: Nat. Toxins . 3, No. 5, 1995, pp. 344-9. doi : 10.1002 / nt.2620030504 . PMID 8581318 . "Non-fatal injury to the lactating mammary gland of the mouse is from 60 to 100 mg / kg. At doses of person above 100 mg / kg, necrosis of myocardial fibers may occur and areas of myocardial fibrosis can be observed in animals surviving for seven days. Hydrothorax and / or pulmonary edema may be present in more severely affected animals. [..] there have been few attempts to investigate the cause of possible toxic effects of the plant in mammals. "

literature

  • AM Hargis et al .: Avocado ( Persea americana ) intoxication in caged birds. In: J. Am. Vet. Med. Assoc. 194 (1), 1989, 64-6, PMID 2914792 .
  • PB Oelrichs et al .: Isolation and identification of a compound from avocado ( Persea americana ) leaves which causes necrosis of the acinar epithelium of the lactating mammary gland and the myocardium. In: Nat. Toxins. 3 (5), 1995, 344-9, PMID 8581318 .
  • KH Plumlee: Plant hazards. In: Vet. Clin. North Am. Small Anim. Pract. 32 (2), 2002, 383-95, PMID 12012742 .

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