The alkaloid profiles of Lupinus sulphureus

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 4, 2009, Pages 1646-1653

  Cook, Daniel ^a   Lee, Stephen T ^a   Gardner, Dale R ^a   Pfister, James A ^a   Welch, Kevin D ^a   Green, Benedict T ^a   Davis, T Zane ^a   Panter, Kip E ^a  

^a AGRICULTURAL RESEARCH SERVICE   (United States)

Author keywords

Crooked calf disease; Lupine; Lupine alkaloids; Lupinus sulphureus

Indexed keywords

ALKALOID; TERATOGENIC AGENT;

ANIMAL; ANIMAL DISEASE; ARTICLE; CATTLE; CATTLE DISEASE; CHEMICALLY INDUCED DISORDER; CHEMISTRY; CLASSIFICATION; CONGENITAL MALFORMATION; FEMALE; LUPIN; MASS FRAGMENTOGRAPHY; PREGNANCY; UNITED STATES;

ABNORMALITIES, DRUG-INDUCED; ALKALOIDS; ANIMALS; CATTLE; CATTLE DISEASES; FEMALE; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; LUPINUS; PREGNANCY; TERATOGENS; UNITED STATES;

LUPINUS SULPHUREUS;

EID: 64549097310     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf803468q     Document Type: Article

References (28)

1. Kingsbury, J. M. Poisonous Plants of the United States and Canada; Prentice-Hall: Englewood Cliffs, NJ, 1964.
2. Wink, M. The role of quinolizidine alkaloids in plant-insect interactions. In Insect-Plant Interactions; Bernays, E. A., Ed.; CRC Press: Boca Raton, FL, 1992; pp 131-166.
3. Chesnut, V. K.; Wilcox, E. V. The stock poisoning plants of Montana: A preliminary report U. S. Department of Agriculture: Washington DC, 1901; Bulletin No. 26, pplOO-110.
4. Palotay, J. L. Crooked Calves. West. Vet. 1959, 6, 16-20.
5. Wagnon, K. A. Lupine poisoning as a possible factor in congenital deformities in cattle. J. Range Manage. 1960, 13, 89-91.
6. Binns, W.; James, L. F. A congenital deformity in calves, similar to "crooked calf disease" has been experimentally produced by feeding heifers lupine and lead. Proc. West. Sect. Am. Soc. Anim. Prod. 1961, 12, 1-3.
7. Shupe, J.; James, L. F.; Binns, W. Observations on crooked calf disease. J. Am. Vet. Med. Assoc. 1967, 151, 191-197.
8. Shupe, J.; Binns, W.; James, L.; Keeler, R. Lupine, a cause of crooked calf disease. J. Am. Vet. Med. Assoc. 1967, 151, 198-203.
9. Shupe, J.; Binns, W.; James, L.; Keeler, R. A congenital deformity in calves induced by the maternal consumption of lupin. Aust. J. Agric. Res 1968, 19, 335-340.
10. Keeler, R. F. Lupin alkaloids from teratogenic and nonteratogenic lupins. III. Identification of anagyrine as the probable teratogen by feeding trials. J. Toxicol. Environ. Health 1976, 1, 878-889.
11. Keeler, R. F.; Panter, K. E. Piperidine alkaloid composition and relation to crooked calf disease-inducing potential of Lupinus formosus. Teratology 1989, 40, 423-432.
12. Panter, K. E.; Gardner, D. R.; Molyneux, R. J. Teratogenic and fetotoxic effects of two piperidine alkaloid-containing lupines (L. formosus and L. arbustus) in cows. J. Nat. Tox. 1998, 7, 131-140.
13. Panter, K. E.; Bunch, T. D.; Keeler, R. F.; Sisson, D. V.; Callan, R. J. Multiple congenital contractures (MCC) and cleft palate induced in goats by ingestion of piperidine alkaloid-containing plants: Reduction in fet al. movement as the probable cause. Clin. Toxicol. 1990, 28, 69-83.
14. Panter, K. E.; Keeler, R. F. Induction of cleft palate in goats by Nicotiana glauca during a narrow gestational period and the relation to reduction in fet al. movement. J. Nat. Toxins 1992, 1, 25-32.
15. Lee, S. T.; Cook, D.; Panter, K. E.; Gardner, D. R.; Ralphs, M. H.; Motteram, E. S.; Pfister, J. A.; Gay, C. C. Lupine induced "Crooked Calf Disease" in Washington and Oregon: identification of the alkaloid profile in Lupinus sulfureus, Lupinus leucophyllus, and Lupinus sericeus. J. Agric. Food. Chem. 2007, 55, 10649-10655.
16. Wink, M.; Carey, D. B. Variability of quinolizidine alkaloid profiles of Lupinus argenteus (Fabaceae) from North America. Biochem. Syst. Ecol. 1994, 22, 663-669.
17. Wink, M.; Meiβner, C.; Witte, L. Patterns of quinolizidine alkaloids in 56 species of the genus Lupinus. Phytochemistry 1995, 38, 139-153.
18. Dolinger, P. M.; Ehrlich, P. R.; Fitch, W. L.; Breedlove, D. E. Alkaloid and predation patterns in Colorado lupine populations. Oecologia 1973, 13, 191-204.
19. Wink, M. Quinolizidine Alkaloids In Methods in Plant Biochemistry, Alkaloids and Sulphur Compounds; Waterman, P., Ed.; Academic Press: London, 1993; Vol. 8, pp 197-239.
20. Kinghorn, A. D.; Balandrin, M. F. Quinolizidine alkaloids of the leguminosae: Structural types, analysis, chemotaxonomy, and biological activities In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley and Sons, Inc.: New York, 1984; Vol. 4.
21. Panter, K. E.; Gardner, D. R.; Gay, C. C.; James, L. F.; Mills, R.; Gay, J. M.; Baldwin, T. J. Observations of Lupinus sulphureus-induced "crooked calf disease". J. Range Manage. 1997, 50, 587-592.
22. Keeler, R. F.; Baker, D. C. Myopathy in cattle induced by alkaloid extracts from Thermopsis montana, Laburnum anagyroides, and a Lupinus sp. J. Comp. Pathol. 1990, 103, 169-182.
23. Planchuelo-Ravelo, A. M.; Witte, L.; Wink, M. Quinolizidine alkaloid profiles of South American Lupins: Lupinus linearis and the Lupinus gibertianus complex. Z. Naturforsch. 1993, 48c, 702-706.
24. Lee, S. T.; Molyneux, R. J.; Panter, K. E.; Chang, C. W. T.; Gardner, D. R.; Pfister, J. A.; Garrossian, M. Ammodendrine and iV-methylammodendrine enantiomers: isolation, optical rotation, and toxicity. J. Nat. Prod. 2005, 68, 681-685.
25. Berenbaum, M. R.; Zangerl, A. R. Stalemates in the coevolutionary arms race: syntheses, synergisms, and sundry other sins In Chemical Mediation of Coevolution, Spenser, K. C, Ed.; Academic Press: San Diego, CA, 1988; pp 113-132.
26. Bowers, M. D.; Puttick, G. M. Response of generalist and specialist insects to qualitative allelochemical variation. J. Chem. Ecol. 1988, 14, 319-351.
27. Berenbaum, M. R.; Zangerl, A. R.; Lee, L. Chemical barriers to adaptation by a specialist herbivore. Oecologia 1989, 80, 501-506.
28. Majak, W.; Keller, W. J.; Duan, Z.; Munro, D.; Smith, R. A.; Davis, A. M.; Ogilvie, R. T. Alkaloid distribution in two species of Lupinus in Central British Columbia. Phytochemistry 1994, 36, 883-885.