Isolation and NMR Study on Swainsonine from Locoweed, Astragalus strictus

Agricultural Sciences in China

Volumn 8, Issue 1, 2009, Pages 115-120

  ZHAO, Bao yu ^a   LIU, Zhong yan ^a   WANG, Jian jun ^b   SUN, Li sha ^a   WANG, Zhan xin ^a   WANG, Yin chao ^a,c  

^a NORTHWEST A F UNIVERSITY   (China)

^b Xi'an Municipal Public Security Bureau   (China)

^c KUNMING INSTITUTE OF BOTANY   (China)

Author keywords

chemical shift assignment; locoweed; NMR; swainsonine

Indexed keywords

EID: 58449121604     PISSN: 16712927     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1671-2927(09)60016-X     Document Type: Article

References (20)

1. Bennett III R.B., Choi J.-R., Montgomery W.D., and Cha J.K. A short, enantioselective synthesis of (-)-swainsonine. Journal of the America Society 111 (1989) 2580-2582
2. Buschmann N., Rückert A., and Blechert S. A new approach to (-)-swainsonine by ruthenium-catalyzed ring rearrangement. Journal of Organical Chemistry 67 (2002) 4325-4329
3. Cao G.R., Li S.J., Duan D.X., and Zhao X.W. The isolation and identification of toxic components from Oxytropis ochrocephala. Journal of Northwest Sci-Tech University of Agriculture and Forestry 17 (1989) 1-8 (in Chinese)
4. Colegate S.M., Dorling P.R., and Huxtable C.R. A spectroscopic investigation of swainsonine: an [.alpha]mannosidase inhibitor isolated from Swaisona canescens. Australian Journal of Chemistry 32 (1979) 2257-2264
5. Elbein A.D., Solf R., Dorling P.R., and Vosbeck K. Swainsonine: An inhibitor of glycoprotein processing. The Proceedings of National Academy of Sciences of the USA 78 (1981) 7393-7397
6. Fujita T., Nagasawa H., Uto Y., Hashimoto T., Asakawa Y., and Hori H. Synthesis of the new mannosidase inhibitors, diversity-oriented 5-substituted swainsonine analogues, via stereoselective mannich reaction. Organic Letters 6 (2004) 827-830
7. Goss P.E., Baptiste J., Fernandes B., Baker M., and Dennis J.W. A phase I study of swainsonine in patients with advanced malignancies. Cancer Research 54 (1994) 1450-1457
8. Hunt J.A., and Roush W.R. 4,5-Diisopropyl-B-[(E)-[(3́- menthofuryl)dimethylsilyl]allyl]-1,3,2-dioxaborolane, an improved china reagent for the anti [.alpha]-hydroxyallylation of aldehydes: application to the enantioselective synthesis of (-)-swainsonine. Journal of Organic Chemistry 62 (1997) 1112-1124
9. Lindsay K.B., and Pyne S.G. Asymmetric synthesis of (-)- swainsonine, (+)-1,2-di-epi-swainsonine and (+)-1,2,8-tri- epi-swainsonine. Journal of Organic Chemistry 67 (2002) 7774-7780
10. McDonald T.P., Jeffree C.E., Li P., Rixon H.W., Brown G., Aitken J.D., MacLellan K., and Sugrue R.J. Evidence that maturation of the N-linked glycans of the respiratory syncytial virus (RSV) glycoproteins is required for virus-mediated cell fusion: The effect of [.alpha]-mannosidase inhibitors on RSV infectivity. Virology 350 (2006) 289-301
11. Miller S.A., and Chamberlin R. Enantiomerically pure polyhydroxylated acyliminium ions, synthesis of the glycosidase inhibitors (-)-swainsonine and (+)- castanospermine. Journal of the America Society 112 (1990) 8100-8112
12. Molyneux R.J., and James L.F. Loco intoxication: Indolizidine alkaloids of spotted locoweed (Astragalus lentiginosus). Science 216 (1982) 190-191
13. Mukai C., Sugimoto Y., Miyazawa K., Yamaguchi S., and Hanaoka M. Stereoselective total synthesis of (±)-swainsonine based on endo mode cyclization. Journal of Organic Chemistry 63 (1998) 6281-6287
14. Pearson W.H., and Hembre E.J. A practical synthesis of (-)- swainsonine. Journal of Organic Chemistry 61 (1996) 7217-7221
15. Stegelmeier B.L., James L.F., Gardner D.R., Panter K.E., Lee S.T., Ralphs M.H., Pfister J.A., and Spraker T.R. Locoweed (Oxytropis sericea)-induced lesions in mule deer (Odocoileius hemionus). Veterinary Pathology 42 (2005) 566-578
16. Tulsiani D.R.P., Skudlarek M.D., and Orgebin-Crist M. Swainsonine induces the production of hybrid glycoproteins and accumulation of oligosaccharides in male reproductive tissues of the rat. Biology of Reproduction 43 (1990) 130-138
17. Zhao B.Y. Astragalus and its poisoning for livestock in China. Chinese Journal of Veterinary Medicine 20 (1994) 15-16 (in Chinese)
18. Zhao B.Y., Cao G.R., Duan D.X., Li S.J., Lu X.K., and Wang J.B. A study on toxicity of Astragalus strictus in goats in Tibet. Acta Veterinaria et Zootechnica Sinica 23 (1992) 276-280 (in Chinese)
19. Zhao B.Y., Fan Y.Y., Fan Z.F., Dong Q., Cao H.M., Li G.Z., and Da N.T. Hazards of locoweed in the west grassland of China and the control of animals loco-toxicosis. Grass-Feeding Livestock 130 (2006) 12-15 (in Chinese)
20. Zhao H., Hans S., Cheng X.H., and Mootoo D.R. Allylated monosaccharides as precursors in triple Reductive amination strategies: Synthesis of castanospermine and swainsonine. Journal of Organic Chemistry 66 (2001) 1761-1767