{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,23]],"date-time":"2026-07-23T18:25:59Z","timestamp":1784831159800,"version":"3.55.0"},"reference-count":25,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2006,5,30]],"date-time":"2006-05-30T00:00:00Z","timestamp":1148947200000},"content-version":"vor","delay-in-days":3924,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Natural Toxins"],"published-print":{"date-parts":[[1995,9]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>It is well known that when lactating livestock eat avocado (<jats:italic>Persea americana<\/jats:italic>) leaves they may develop non\u2010infectious mastitis and agalactia. This is associated with extensive coagulative necrosis of the secretory acinar epithelium and interstitial oedema, congestion, and haemorrhage. Similar lesions have been produced in mammary glands of lactating mice fed a diet containing a small percentage of freeze\u2010dried avocado leaf. Tests using these animals have been used to isolate the active principle, termed persin, from avocado leaves. The purified persin was examined using IR, NMR, and UV spectroscopy and mass spectrometry, and identified as (Z,Z)\u20101\u2010(acetyloxy)\u20102\u2010hydroxy\u201012,15\u2010heneicosadien\u20104\u2010one. Persin has previously been isolated from avocado leaves and shown to have antifungal properties and to be toxic to silkworms. Our tests have shown that persin at the dose rate of 60\u2010100 mg\/kg has the same effect on mammary glands in lactating mice as leaves from avocado. Enantioselective syntheses of the R and the S isomers of persin and related derivatives were carried out. These compounds were tested for activity required to induce widespread lactating mammary gland necrosis in mice, and only the <jats:italic>R<\/jats:italic> isomer was found active. At doses of persin above 100 mg\/kg necrosis of myocardial fibres may occur and hydrothorax may be present in severely affected animals. The mechanism of action of persin on both the mammary gland and the myocardium remain to be resolved. \u00a9 1995 Wiley\u2010Liss, inc.<\/jats:p>","DOI":"10.1002\/nt.2620030504","type":"journal-article","created":{"date-parts":[[2006,10,18]],"date-time":"2006-10-18T02:30:02Z","timestamp":1161138602000},"page":"344-349","source":"Crossref","is-referenced-by-count":75,"title":["Isolation and identification of a compound from avocado (<i>Persea americana<\/i>) leaves which causes necrosis of the acinar epithelium of the lactating mammary gland and the myocardium"],"prefix":"10.1002","volume":"3","author":[{"given":"Peter B.","family":"Oelrichs","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jack C.","family":"Ng","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alan A.","family":"Seawright","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Annemarie","family":"Ward","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lothar","family":"Sch\u00e4ffeler","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"John K.","family":"Macleod","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2006,5,30]]},"reference":[{"key":"e_1_2_1_2_1","first-page":"606","volume-title":"Comprehensive Organic Chemistry","author":"Barton D","year":"1979"},{"key":"e_1_2_1_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf60182a019"},{"key":"e_1_2_1_4_1","doi-asserted-by":"publisher","DOI":"10.1071\/CH9941661"},{"key":"e_1_2_1_5_1","first-page":"546","volume-title":"Plant\u2010Associated Toxins: Agricultural, Phytochemical and Ecological Aspects","author":"Burger WP","year":"1994"},{"key":"e_1_2_1_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/np50067a003"},{"key":"e_1_2_1_7_1","doi-asserted-by":"publisher","DOI":"10.1271\/bbb1961.39.1167"},{"key":"e_1_2_1_8_1","first-page":"381","article-title":"Toxicity of avocado (Persea americana [Guatemalan var.]) leaves: Review and preliminary report. 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