Persin

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For the island in Bulgaria, see Persin Island.
Persin
Persin Structural Formulae V.1.svg
Names
Preferred IUPAC name
(2R,12Z,15Z)-2-Hydroxy-4-oxohenicosa-12,15-dien-1-yl acetate
Identifiers
  • 56164-07-9 checkY
3D model (JSmol)
UNII
  • CCCCCC=CCC=CCCCCCCCC(=O)CC(COC(=O)C)O
Properties
C23H40O4
Molar mass 380.569 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY  (what is checkY☒N ?)
Infobox references

Persin is a fungicidal toxin present in the avocado.[1] Persin is an oil-soluble compound structurally similar to a fatty acid, and it leaches into the body of the fruit from the seeds.

The relatively low concentrations of persin in the ripe pulp of the avocado fruit is generally considered harmless to humans. Negative effects in humans are primarily in allergic individuals. When persin is consumed by domestic animals through the leaves or bark of the avocado tree, or skins and seeds of the avocado fruit, it is toxic and dangerous.[2][3]

Pathology[]

Consumption of the leaves and bark of the avocado tree, or the skin and pit of the avocado fruit have been shown to have the following effects:[2]

  • In birds, which are particularly sensitive to the avocado toxin, the symptoms are: increased heart rate, myocardial tissue damage, labored breathing, disordered plumage, unrest, weakness, and apathy. High doses cause acute respiratory syndrome (asphyxia), with death approximately 12 to 24 hours after consumption.
  • Lactating rabbits and mice: non-infectious mastitis and agalactia after consumption of leaves or bark.
  • Rabbits: cardial arrhythmia, submandibular edema and death after consumption of leaves.
  • Cows and goats: mastitis, decreased milk production after consumption of leaves or bark.
  • Horses: clinical effects occur mainly in mares, and includes noninfectious mastitis, as well as occasional gastritis and colic.
  • Cats, dogs: mild stomach upset may occur, with potential to cause heart damage.[2]
  • Hares, pigs, rats, sheep, ostriches, chickens, turkeys and fish: symptoms of intoxication similar those described above. The lethal dose is not known; the effect is different depending upon the animal species.[4]
  • Mice: non-fatal injury to the lactating mammary gland from 60 to 100 mg/kg Persin. Necrosis of myocardial fibres with 100 mg/kg Persin. 200 mg/kg lethal.[1]

Additional pharmacology[]

Animal studies show that exposure to persin leads to apoptosis in certain types of breast cancer cells.[5] It has also been shown to enhance the cytotoxic effect of tamoxifen in vitro.[6] Persin is however highly insoluble in aqueous solutions and more research will be needed to put it into a soluble tablet form.[6]

References[]

  1. ^ a b Oelrichs PB, Ng JC, Seawright AA, Ward A, Schäffeler L, MacLeod JK (1995). "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". Nat. Toxins. 3 (5): 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 fibres may occur and areas of myocardial fibrosis can be observed in animals surviving for seven days. Hydrothorax and/or pulmonary oedema 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.
  2. ^ a b c ASPCA Poison Control: Avocado on aspca.org
  3. ^ Morton, Julia F. "NewCROP - Avocado Persea americana". hort.purdue.edu. Purdue University. Retrieved 3 December 2017.
  4. ^ Clipsham, R. "Avocado Toxicity". Retrieved 2010-04-28.
  5. ^ Butt AJ, Roberts CG, Seawright AA, Oelrichs PB, MacLeod JK, Liaw TY, Kavallaris M, Somers-Edgar TJ, Lehrbach GM, Watts CK, Sutherland RL (2006). "A novel plant toxin, persin, with in vivo activity in the mammary gland, induces Bim-dependent apoptosis in human breast cancer cells". Mol Cancer Ther. 5 (9): 2300–9. doi:10.1158/1535-7163.MCT-06-0170. PMID 16985064.
  6. ^ a b Roberts CG, Gurisik E, Biden TJ, Sutherland RL, Butt AJ (October 2007). "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". Mol. Cancer Ther. 6 (10): 2777–85. doi:10.1158/1535-7163.MCT-07-0374. PMID 17913853.
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