{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,4]],"date-time":"2025-11-04T10:10:58Z","timestamp":1762251058153},"reference-count":28,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2005,6,1]],"date-time":"2005-06-01T00:00:00Z","timestamp":1117584000000},"content-version":"vor","delay-in-days":5691,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Teratology"],"published-print":{"date-parts":[[1989,11]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A congenital deformity condition called crooked calf disease, of widespread occurrence in western North America, is known to be induced by maternal ingestion during gestation of certain members of the <jats:italic>Lupinus<\/jats:italic> genus containing the quinolizidine alkaloid teratogen anagyrine. Because some piperidine alkaloids from other sources induce a similar condition, we have investigated the alkaloid composition and teratogenicity of <jats:italic>Lupinus formousus<\/jats:italic>, reported by others to be low in quinolizidines but rich in the type of piperidine alkaloids that we have speculated would be teratogenic. GC\/MS analysis of <jats:italic>L. formosus<\/jats:italic> showed seven major and nine minor components in the total alkaloid fraction. All seven major and nine minor components in the total alkaloid fraction. All seven major and five of the nine minor components, representing all but 3% of the fraction, were identified by mass spectrometric fragmentation patterns and GC retention times. They included several potentially teratogenic piperidine alkaloids (including a very large amount of ammodendrine), as well as several nonteratogenic quinolizidine alkaloids plus a trace (at nonteratogenic levels) of the known quinolizidine teratogen anagyrine. The plant induced severe crooked calf disease with limb, spinal, and palate involvement in experimental calves. The deformities are believed to have been induced by ammodendrine.<\/jats:p>","DOI":"10.1002\/tera.1420400503","type":"journal-article","created":{"date-parts":[[2005,6,11]],"date-time":"2005-06-11T15:45:26Z","timestamp":1118504726000},"page":"423-432","source":"Crossref","is-referenced-by-count":59,"title":["Piperidine alkaloid composition and relation to crooked calf disease\u2010inducing potential of <i>Lupinus formosus<\/i>"],"prefix":"10.1002","volume":"40","author":[{"given":"Richard F.","family":"Keeler","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kip E.","family":"Panter","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2005,6]]},"reference":[{"key":"e_1_2_1_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/0003-2697(71)90344-7"},{"key":"e_1_2_1_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00822a032"},{"key":"e_1_2_1_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00934a008"},{"key":"e_1_2_1_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf00119a003"},{"key":"e_1_2_1_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/tera.1420070105"},{"key":"e_1_2_1_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/tera.1420070106"},{"key":"e_1_2_1_8_1","doi-asserted-by":"publisher","DOI":"10.3109\/15563657408987995"},{"key":"e_1_2_1_9_1","doi-asserted-by":"publisher","DOI":"10.1080\/15287397609529391"},{"key":"e_1_2_1_10_1","doi-asserted-by":"publisher","DOI":"10.3109\/15563657908989896"},{"key":"e_1_2_1_11_1","first-page":"301","volume-title":"Proceedings of the Second International Lupine Conference","author":"Keeler R. F.","year":"1984"},{"key":"e_1_2_1_12_1","unstructured":"Keeler R. F.(1988) Unpublished observations."},{"key":"e_1_2_1_13_1","doi-asserted-by":"publisher","DOI":"10.3109\/15563657809149583"},{"key":"e_1_2_1_14_1","doi-asserted-by":"publisher","DOI":"10.3109\/15563658308990049"},{"key":"e_1_2_1_15_1","first-page":"50","article-title":"Teratogenicity and toxicity of wild tree tobacco, Nicotiana glauca, in sheep","volume":"74","author":"Keeler R. F.","year":"1984","journal-title":"Cornell Vet."},{"key":"e_1_2_1_16_1","first-page":"324","volume-title":"Plant Toxicolgy","author":"Keeler R. F.","year":"1985"},{"key":"e_1_2_1_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/tera.1420300109"},{"key":"e_1_2_1_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/jps.2600670348"},{"key":"e_1_2_1_19_1","first-page":"4","volume-title":"Alkaloids: Chemical and Biological Perspectives","author":"Kinghorn A. D.","year":"1984"},{"key":"e_1_2_1_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0031-9422(00)83799-1"},{"key":"e_1_2_1_21_1","doi-asserted-by":"crossref","unstructured":"Panter K. E.(1983)Toxicity and Teratogenicity of Conium maculatum in Swine and Hamsters. Ph. D. Dissertation.106pp University of Illinois Urbana.","DOI":"10.1016\/0041-0101(83)90223-4"},{"key":"e_1_2_1_22_1","first-page":"1368","article-title":"Induction of cleft palate in newborn pigs by maternal ingestion of poison hemlock (Conium maculatum)","volume":"46","author":"Panter K. E.","year":"1985","journal-title":"Am. J. Vet. Res."},{"key":"e_1_2_1_23_1","doi-asserted-by":"publisher","DOI":"10.3109\/15563658809000345"},{"key":"e_1_2_1_24_1","first-page":"191","article-title":"Observations on crooked calf disease","volume":"151","author":"Shupe J. L.","year":"1967","journal-title":"J. Am. Vet. Med. Assoc."},{"key":"e_1_2_1_25_1","first-page":"198","article-title":"Lupine, a cause of crooked calf disease","volume":"151","author":"Shupe J. L.","year":"1967","journal-title":"J. Am. Vet. Med. Assoc."},{"key":"e_1_2_1_26_1","doi-asserted-by":"publisher","DOI":"10.1071\/AR9680335"},{"key":"e_1_2_1_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0031-9422(00)84842-6"},{"key":"e_1_2_1_28_1","unstructured":"Wink M.(1980)Physiologisch\u2010Chemische Grundlagen der Alkaloid\u2010Biosynthese(Part 3.2.1.1 A66.4 Tab 6). Dissertation. Technische Universiat Carolo\u2010Wilhelmina Braunschweig."},{"key":"e_1_2_1_29_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2007-969928"}],"container-title":["Teratology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Ftera.1420400503","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/tera.1420400503","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,22]],"date-time":"2023-10-22T07:16:56Z","timestamp":1697959016000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/tera.1420400503"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[1989,11]]},"references-count":28,"journal-issue":{"issue":"5","published-print":{"date-parts":[[1989,11]]}},"alternative-id":["10.1002\/tera.1420400503"],"URL":"https:\/\/doi.org\/10.1002\/tera.1420400503","archive":["Portico"],"relation":{},"ISSN":["0040-3709","1096-9926"],"issn-type":[{"value":"0040-3709","type":"print"},{"value":"1096-9926","type":"electronic"}],"subject":[],"published":{"date-parts":[[1989,11]]}}}