鱷梨素

鱷梨素
	IUPAC名; (2R,12Z,15Z)-2-Hydroxy-4-oxohenicosa-12,15-dien-1-yl acetate
識別
CAS號	56164-07-9
PubChem	6365563
SMILES	CCCCCC=CCC=CCCCCCCCC(=O)CC(COC(=O)C)O;
性質
化學式	C23H40O4
摩爾質量	380.56 g·mol−1
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

鱷梨素^[1]（英語：Persin）是一種存在於酪梨中的抗真菌毒素^[2]。其結構和脂肪酸相似，為無色脂溶性液體。

酪梨全株都含有鱷梨素，包括果實、葉片、莖和種子等，特別是葉子含量最多^[3]，為0.9-1%^[4]。

成熟果肉中鱷梨素含量相對較低，除對其過敏人士外，鱷梨素通常對人無害。但對家畜有毒，特別是攝入酪梨的葉、樹皮、種子和果皮時，會導致嚴重的中毒反應^[5]^[6]。

毒性

不同動物攝入酪梨的葉片、樹皮、果皮和果核後，會產生不同的不良反應^[5]^[7]：

鳥類對鱷梨素最敏感，產生的不良反應有心跳加速、心肌組織損害、頸部和胸部皮下水腫、呼吸困難、羽毛紊亂、不安、虛弱、缺乏活力和食欲不振等。高劑量下則造成嚴重窒息，並且在12-48小時內死亡。人工飼養的鳥似乎比野生鳥類對鱷梨素更敏感，但諸如雞和火雞等部分鳥類有更高的抵抗力。
處於哺乳期家兔和小鼠在食用葉子或樹皮後會出現非感染性乳腺炎和奶水減少。對於一般小鼠而言，攝入60-100 mg/kg的鱷梨素會對哺乳期母鼠乳腺造成非致命損傷，100 mg/kg則引起心肌纖維壞死，200 mg/kg則造成死亡^[2]。
家兔食用葉子後出現心律失常、頜下水腫和死亡。
牛和山羊在食用葉片或樹皮後會引起乳腺炎和奶水減少。山羊攝入20 g/kg的樹葉會導致嚴重乳腺炎，達到30 g/kg將引起心臟損傷。
對於馬。中毒症狀主要發生在母馬上，包括非感染性乳腺炎，偶爾伴有胃炎和急性腹痛。也可能出現頭部、舌頭和胸部腫脹。
對於貓和狗，可能會出現輕微胃部不適和心臟損害^[5]。相比而言，狗的抵抗力可能更強一些。
對於野兔、豬、大鼠、綿羊、鴕鳥、雞、火雞和魚等動物，鱷梨素中毒症狀和前面提到症狀相似，但其致死量尚未明確，且因具體物種而異^[8]。

診斷

對於鱷梨素中毒的診斷只能依據詢問接觸史和臨床症狀來確定，而且尚未有特定檢測方法^[9]。

治療

治療鱷梨素中毒採用的藥物有非甾體抗炎藥、止痛藥以及一些治療充血性心力衰竭的藥物^[7]。

藥理學

動物研究表明接觸鱷梨素會引起特定的乳腺癌細胞凋亡^[10]。在體外研究中，鱷梨素與他莫昔芬聯合會增強他莫昔芬的細胞毒性作用。然而作為一種脂溶性物質，鱷梨素在水中溶解度很差，如何製成水溶性片劑還是一個亟待研究的問題^[11]。

參考文獻

^ 陳方良、張松、陳超、星雲. 家庭养犬常见的有毒有害物. 中國工作犬業. 2018, (6): 21–22. doi:10.3969/j.issn.1673-0135.2018.06.005.
^ ^2.0 ^2.1 Oelrichs PB, Ng JC, Seawright AA, Ward A, Schäffeler L, MacLeod JK. 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. 1995, 3 (5): 344–9. PMID 8581318. doi:10.1002/nt.2620030504. 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.
^ Food Hazards - Special Pet Topics. MSD Veterinary Manual. [2023-12-05] （英語）.
^ Oelrichs, Peter B.; Ng, Jack C.; Seawright, Alan A.; Ward, Annemarie; Schäffeler, Lothar; Macleod, John K. 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. Natural Toxins. September 1995, 3 (5): 344–349. ISSN 1056-9014. doi:10.1002/nt.2620030504 （英語）.
^ ^5.0 ^5.1 ^5.2 ASPCA Poison Control: Avocado on aspca.org
^ Morton, Julia F. NewCROP - Avocado Persea americana. hort.purdue.edu. Purdue University. [3 December 2017].
^ ^7.0 ^7.1 Avocado Toxicosis in Animals - Toxicology. MSD Veterinary Manual. [2023-12-05] （英語）.
^ Clipsham, R. Avocado Toxicity. [2010-04-28].
^ Avocado Toxicosis in Animals - Toxicology.
^ Butt AJ, Roberts CG, Seawright AA, Oelrichs PB, MacLeod JK, Liaw TY, Kavallaris M, Somers-Edgar TJ, Lehrbach GM, Watts CK, Sutherland RL. 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. 2006, 5 (9): 2300–9. PMID 16985064. doi:10.1158/1535-7163.MCT-06-0170 .
^ Roberts CG, Gurisik E, Biden TJ, Sutherland RL, Butt AJ. 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. October 2007, 6 (10): 2777–85. PMID 17913853. doi:10.1158/1535-7163.MCT-07-0374 .

[1] 陳方良、張松、陳超、星雲. 家庭养犬常见的有毒有害物. 中國工作犬業. 2018, (6): 21–22. doi:10.3969/j.issn.1673-0135.2018.06.005.

[OelrichsSeawright1995-2] 2.0 ^2.1 Oelrichs PB, Ng JC, Seawright AA, Ward A, Schäffeler L, MacLeod JK. 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. 1995, 3 (5): 344–9. PMID 8581318. doi:10.1002/nt.2620030504. 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.

[3] Food Hazards - Special Pet Topics. MSD Veterinary Manual. [2023-12-05] （英語）.

[4] Oelrichs, Peter B.; Ng, Jack C.; Seawright, Alan A.; Ward, Annemarie; Schäffeler, Lothar; Macleod, John K. 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. Natural Toxins. September 1995, 3 (5): 344–349. ISSN 1056-9014. doi:10.1002/nt.2620030504 （英語）.

[aspca-5] 5.0 ^5.1 ^5.2 ASPCA Poison Control: Avocado on aspca.org

[JFM_(1987-2017)-6] Morton, Julia F. NewCROP - Avocado Persea americana. hort.purdue.edu. Purdue University. [3 December 2017].

[:0-7] 7.0 ^7.1 Avocado Toxicosis in Animals - Toxicology. MSD Veterinary Manual. [2023-12-05] （英語）.

[8] Clipsham, R. Avocado Toxicity. [2010-04-28].

[9] Avocado Toxicosis in Animals - Toxicology.

[10] Butt AJ, Roberts CG, Seawright AA, Oelrichs PB, MacLeod JK, Liaw TY, Kavallaris M, Somers-Edgar TJ, Lehrbach GM, Watts CK, Sutherland RL. 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. 2006, 5 (9): 2300–9. PMID 16985064. doi:10.1158/1535-7163.MCT-06-0170 .

[Roberts-11] Roberts CG, Gurisik E, Biden TJ, Sutherland RL, Butt AJ. 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. October 2007, 6 (10): 2777–85. PMID 17913853. doi:10.1158/1535-7163.MCT-07-0374 .

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]