Dehydropyrrolizidine alkaloids, including monoesters with an unusual esterifying acid, from cultivated Crotalaria juncea (Sunn Hemp cv.'Tropic Sun')

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 14, 2012, Pages 3541-3550

  Colegate, Steven M ^a   Gardner, Dale R ^a   Joy, Robert J ^b   Betz, Joseph M ^c   Panter, Kip E ^a  

^a U S DEPARTMENT OF AGRICULTURE   (United States)

^b USDA NRCS   (United States)

^c NATIONAL INSTITUTES OF HEALTH   (United States)

Author keywords

'Tropic Sun'; Crotalaria juncea; hemijunceine; HPLC ESI MS; isohemijunceine; junceine; N oxides; pyrrolizidine alkaloids; trichodesmine

Indexed keywords

'TROPIC SUN'; CROTALARIA JUNCEA; HEMIJUNCEINE; HPLC-ESI/MS; ISOHEMIJUNCEINE; JUNCEINE; N-OXIDES; PYRROLIZIDINE ALKALOID; TRICHODESMINE;

HEMP; MANURES; METABOLITES; SEED; SPECTROSCOPIC ANALYSIS;

NITROGEN COMPOUNDS;

DRUG DERIVATIVE; LACTONE; MONOCROTALINE; PYRROLIZIDINE ALKALOID; TRICHODESMINE;

AGRICULTURE; ARTICLE; CHEMISTRY; CROTALARIA; ELECTROSPRAY MASS SPECTROMETRY; ESTERIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHODOLOGY; PLANT LEAF; PLANT ROOT; PLANT SEED; PLANT STEM; SOIL;

AGRICULTURE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CROTALARIA; ESTERIFICATION; LACTONES; MONOCROTALINE; PLANT LEAVES; PLANT ROOTS; PLANT STEMS; PYRROLIZIDINE ALKALOIDS; SEEDS; SOIL; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

CROTALARIA JUNCEA; NEMATODA;

EID: 84859588738     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf205296s     Document Type: Article

References (30)

1. Cook, C. G.; White, G. A. Crotalaria juncea: a potential multi-purpose fiber crop. In Progress in New Crops; Janick, J., Ed.; ASHS Press: Arlington, VA, 1996; http://www.hort.purdue.edu/newcrop/proceedings1996/v3-389.html (last accessed Nov 30, 2011).
2. U.S. Department of Agriculture.. Sunn Hemp: a Cover Crop for Southern and Tropical Farming Systems; Soil Quality-Agronomy Technical Note 10; 1999; http://soils.usda.gov/sqi/management/files/sq-atn-10.pdf (last accessed Nov 30, 2011).
3. USDA Natural Resources Conservation Service. 'Tropic Sun' Sunn Hemp, 2009; http://www.plant-materials.nrcs.usda.gov/pubs/hipmcrb8433.pdf (last accessed Nov 30, 2011).
4. Adams, R.; Gianturco, M. The alkaloids of Crotalaria juncea J. Am. Chem. Soc. 1956, 78, 1919-1921
5. Williams, M. C.; Molyneux, R. J. Occurrence, concentration and toxicity of pyrrolizidine alkaloids in Crotalaria seeds Weed Sci. 1987, 35, 476-481
6. Ji, X.; Khan, I.; Mosjidis, J. A.; Wang, H.; Livant, P. Variability for the presence of pyrrolizidine alkaloids in Crotalaria juncea L Pharmazie 2005, 60, 620-622
7. Edgar, J. A.; Colegate, S. M.; Boppré, M.; Molyneux, R. J. Pyrrolizidine alkaloids in food: a spectrum of potential health consequences Food Addit. Contam.: Part A 2011, 28, 308-324
8. Colegate, S. M.; Edgar, J. A.; Knill, A. M.; Lee, S. T. Solid phase extraction and LCMS profiling of pyrrolizidine alkaloids and their N -oxides: a case study of Echium plantagineum Phytochem. Anal. 2005, 16, 108-119
9. Bull, L. B.; Culvenor, C. C. J.; Dick, A. T. In The Pyrrolizidine Alkaloids: Their Chemistry, Pathogenicity and other Biological Properties; North-Holland: Amsterdam, The Netherlands, 1968; pp 60-66.
10. Molyneux, R. J.; Johnson, A. E.; Roitman, J. N.; Benson, M. E. Chemistry of toxic range plants. Determination of pyrrolizidine alkaloid content and composition in Senecio species by nuclear magnetic resonance spectroscopy J. Agric. Food Chem. 1979, 27, 494-499
11. Hartmann, T.; Witte, L. Chemistry, biology, and chemoecology of the pyrrolizidine alkaloids. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon Press: Oxford, U.K., 1995; Vol. 9, pp 155-233.
12. Peñaloza, G. C.; Peláez, J. C. A. Evaluation of biological activity of Crotalaria juncea extracts through a Drosophila melanogaster model Vitae 2008, 15, 279-284
13. Atal, C. K.; Sharma, R. K.; Culvenor, C. C. J.; Smith, L. W. Alkaloids of Crotalaria rubiginosa Willd. trichodesmine and junceine Aust. J. Chem. 1966, 19, 2189-2191
14. Roeder, E.; Sarg, T.; El-Dahmy, S.; Abdel Ghani, A. Pyrrolizidine alkaloids from Crotalaria aegyptiaca Phytochemistry 1993, 34, 1421-1423
15. Culvenor, C. C. J.; Edgar, J. A.; Frahn, J. L.; Smith, L. W.; Ulubelen, A.; Doganca, S. The structure of anadoline Aust. J. Chem. 1975, 28, 173-178
16. Röder, E. Medicinal plants in Europe containing pyrrolizidine alkaloids Pharmazie 1995, 50, 83-98
17. Williams, M. T.; Warnock, B. J.; Betz, J. M.; Beck, J. J.; Gardner, D. R.; Lee, S. T.; Molyneux, R. J.; Colegate, S. M. Detection of high levels of pyrrolizidine- N -oxides in the endangered plant Cryptantha crassipes (Terlingua Creek cat's-eye) using HPLC-ESI-MS Phytochem. Anal. 2011, 22, 532-540
18. Wiedenfeld, H.; Röder, E. Pyrrolizidine alkaloids from Ageratum conyzoides Planta Med. 1991, 57, 578-579
19. Weber, S.; Eisenreich, W.; Bacher, A.; Hartmann, T. Pyrrolizidine alkaloids of the lycopsamine type: biosynthesis of trachelanthic acid Phytochemistry 1999, 1005-1014
20. Logie, C. G.; Grue, M. R.; Liddell, J. R. Proton NMR spectroscopy of pyrrolizidine alkaloids Phytochemistry 1994, 37, 43-109
21. Jones, A. J.; Culvenor, C. C. J.; Smith, L. W. Pyrrolizidine alkaloids - a carbon-13 NMR study Aust. J. Chem. 1982, 35, 1173-1184
22. 13C-NMR spectra of saturated pyrrolizidine monoester alkaloids J. Nat. Prod. 1982, 45, 300-336
23. Pedersen, E.; Larsen, E. Mass spectrometry of some pyrrolizidine alkaloids J. Mass Spectrom. 1970, 4, 249-256
24. Stelljes, M. E.; Kelley, R. B.; Molyneux, R. J.; Seiber, J. N. GC-MS determination of pyrrolizidine alkaloids in four Senecio species J. Nat. Prod. 1991, 54, 759-773
25. Roitman, J. N. The pyrrolizidine alkaloids of Senecio triangularis Aust. J. Chem. 1983, 36, 1203-1213
26. Boppré, M.; Colegate, S. M.; Edgar, J. A. Pyrrolizidine alkaloids of Echium vulgare honey found in pure pollen J. Agric. Food Chem. 2005, 53, 594-600
27. Thoden, T. C.; Boppré, M. Plants producing pyrrolizidine alkaloids: sustainable tools for nematode management? Nematology 2010, 12, 1-24
28. Culvenor, C. C. J.; Edgar, J. A.; Jago, M. V.; Outteridge, A.; Peterson, J. E.; Smith, L. W. Hepato- and pneumotoxicity of pyrrolizidine alkaloids and derivatives in relation to molecular structure Chem.-Biol. Interact. 1976, 12, 299-324
29. Johnson, A. E.; Molyneux, R. J.; Merrill, G. B. Chemistry of toxic range plants. Variation in pyrrolizidine alkaloid content of Senecio, Amsinckia, and Crotalaria species J. Agric. Food Chem. 1985, 33, 50-55
30. Fletcher, M. T.; McKenzie, R. A.; Blaney, B. J.; Reichmann, K. G. Pyrrolizidine alkaloids in Crotalaria taxa from northern Australia: risk to grazing livestock J. Agric. Food Chem. 2009, 57, 311-319