Persin
- For an island in Bulgaria, see Persin Island
 | |
| Names | |
|---|---|
| IUPAC name
(R, 12Z,15Z)-2-Hydroxy-4-oxohenicosa-12,15-dienyl acetate | |
| Identifiers | |
60640-59-7  | |
| Jmol interactive 3D | Image |
| PubChem | 6365563 |
| |
| Properties | |
| C23H40O4 | |
| Molar mass | 380.57 g·mol−1 |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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| Infobox references | |
Persin is a fungicidal toxin present in the avocado.[1] It is generally harmless to humans, but when consumed by domestic animals in large quantities it is dangerous.[2]
Persin is an oil-soluble compound structurally similar to a fatty acid, and it leaches into the body of the fruit from the pits. Negative effects in humans seem to be primarily in allergic individuals.
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: vomiting, diarrhea.
- 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.[3]
Additional pharmacology
Animal studies show that exposure to persin leads to apoptosis in certain types of breast cancer cells.[4] It has also been shown to enhance the cytotoxic effect of tamoxifen in vitro.[5] Persin is however highly insoluble in aqueous solutions and more research will be needed to put it into a soluble tablet form.[5]
References
- ↑ 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.
- 1 2 ASPCA Poison Control: Avocado
- ↑ Clipsham, R. "Avocado Toxicity". Retrieved 2010-04-28.
- ↑ Butt AJ, Roberts CG, Seawright AA, Oelrichs PB, MacLeod JK, Liaw TYE, Kavallaris M, Somers-Edgar TJ, Lehrbach GM, Watts CK and 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.
- 1 2 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.