{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,13]],"date-time":"2026-01-13T16:58:36Z","timestamp":1768323516966,"version":"3.49.0"},"reference-count":75,"publisher":"American Association for the Advancement of Science (AAAS)","issue":"4712","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Science"],"published-print":{"date-parts":[[1985,8,2]]},"abstract":"<jats:p>\n            The toxicity of macrocyclic pyrrolizidine alkaloids in the livers of man and animals has been attributed to the formation of reactive pyrroles from dihydropyrrolizines. Now a novel metabolite,\n            <jats:italic>trans<\/jats:italic>\n            -4-hydroxy-2-hexenal, has been isolated from the macrocyclic pyrrolizidine alkaloid senecionine, in an in vitro hepatic microsomal system. Other alkenals such as\n            <jats:italic>trans<\/jats:italic>\n            -4-hydroxy-2-nonenal have previously been isolated from microsomal systems when treated with halogenated hydrocarbons or subjected to lipid peroxidation. The in vivo pathology caused by\n            <jats:italic>trans<\/jats:italic>\n            -4-hydroxy-2-hexenal appears to be identical to that previously attributed to reactive pyrroles. There are similarities between the toxic effects of this alkenal and those of centrilobular hepatotoxins such as CCl\n            <jats:sub>4<\/jats:sub>\n            and other alkenals formed during lipid peroxidation.\n          <\/jats:p>","DOI":"10.1126\/science.4012327","type":"journal-article","created":{"date-parts":[[2006,10,5]],"date-time":"2006-10-05T19:42:50Z","timestamp":1160077370000},"page":"472-475","source":"Crossref","is-referenced-by-count":63,"title":["<i>Trans<\/i>\n            -4-Hydroxy-2-Hexenal: a Reactive Metabolite from the Macrocyclic Pyrrolizidine Alkaloid Senecionine"],"prefix":"10.1126","volume":"229","author":[{"given":"H. J.","family":"Segall","sequence":"first","affiliation":[{"name":"School of Veterinary Medicine, Department of Pharmacology and Toxicology, University of California, Davis 95616"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"D. W.","family":"Wilson","sequence":"additional","affiliation":[{"name":"School of Veterinary Medicine, Department of Pathology, University of California, Davis 95616"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"J. L.","family":"Dallas","sequence":"additional","affiliation":[{"name":"Department of Biological Chemistry, University of California, Davis"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"William F.","family":"Haddon","sequence":"additional","affiliation":[{"name":"Western Regional Research Center, U.S. Department ofAgriculture, Berkeley, California 94710"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"221","reference":[{"key":"e_1_2_1_1_1","first-page":"2809","volume":"28","year":"1979","unstructured":"BENEDETTI, A, BIOCH PHARM 28: 2809 (1979).","journal-title":"BIOCH PHARM"},{"key":"e_1_2_1_2_1","doi-asserted-by":"crossref","first-page":"303","DOI":"10.1042\/bj1800303","volume":"180","year":"1979","unstructured":"BENEDETTI, A, EFFECTS OF DIFFUSIBLE PRODUCTS OF PEROXIDATION OF RAT-LIVER MICROSOMAL LIPIDS, BIOCHEMICAL JOURNAL 180: 303 (1979).","journal-title":"BIOCHEMICAL JOURNAL"},{"key":"e_1_2_1_3_1","doi-asserted-by":"crossref","first-page":"281","DOI":"10.1016\/0005-2760(80)90209-X","volume":"620","year":"1980","unstructured":"BENEDETTI, A, IDENTIFICATION OF 4-HYDROXYNONEAL AS A CYTO-TOXIC PRODUCT ORIGINATING FROM THE PEROXIDATION OF LIVER MICROSOMAL LIPIDS, BIOCHIMICA ET BIOPHYSICA ACTA 620: 281 (1980).","journal-title":"BIOCHIMICA ET BIOPHYSICA ACTA"},{"key":"e_1_2_1_4_1","doi-asserted-by":"crossref","first-page":"172","DOI":"10.1016\/0005-2760(84)90219-4","volume":"792","year":"1984","unstructured":"BENEDETTI, A, CYTO-TOXIC ALDEHYDES ORIGINATING FROM THE PEROXIDATION OF LIVER MICROSOMAL LIPIDS - IDENTIFICATION OF 4,5-DIHYDROXYDECENAL, BIOCHIMICA ET BIOPHYSICA ACTA 792: 172 (1984).","journal-title":"BIOCHIMICA ET BIOPHYSICA ACTA"},{"key":"e_1_2_1_5_1","doi-asserted-by":"crossref","first-page":"331","DOI":"10.1016\/0009-2797(81)90008-9","volume":"35","year":"1981","unstructured":"BENEDETTI, A, INHIBITION OF PROTEIN-SYNTHESIS BY CARBONYL-COMPOUNDS (4-HYDROXYALKENALS) ORIGINATING FROM THE PEROXIDATION OF LIVER MICROSOMAL LIPIDS, CHEMICO-BIOLOGICAL INTERACTIONS 35: 331 (1981).","journal-title":"CHEMICO-BIOLOGICAL INTERACTIONS"},{"key":"e_1_2_1_6_1","first-page":"56","year":"1981","unstructured":"BENEDETTI, A, RECENT ADV LIPID PER: 56 (1981).","journal-title":"RECENT ADV LIPID PER"},{"key":"e_1_2_1_7_1","first-page":"165","volume":"136","year":"1960","unstructured":"BILBEY, DLJ, THE SEGMENTAL ANATOMY OF THE HUMAN LIVER, ANATOMICAL RECORD 136: 165 (1960).","journal-title":"ANATOMICAL RECORD"},{"key":"e_1_2_1_8_1","doi-asserted-by":"crossref","first-page":"357","DOI":"10.1016\/S0031-9422(00)88063-2","volume":"3","year":"1964","unstructured":"BOTTOMLEY, W, PYRROLIZIDINE ALKALOIDS - THE BIOSYNTHESIS OF RETRONECINE, PHYTOCHEMISTRY 3: 357 (1964).","journal-title":"PHYTOCHEMISTRY"},{"key":"e_1_2_1_9_1","unstructured":"BULL L.B. 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