Naturally occurring glycosidase inhibitors

Bioactive Natural Products: Detection, Isolation, and Structural Determination, Second Edition

Volumn , Issue , 2007, Pages 407-420

  Nash, Robert J ^a  

^a Summit (Wales) Limited   (United Kingdom)

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EID: 70449668194     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (35)

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2. Nash, R.J., Watson, A.A., and Evinson, E.L., Immunomodulatory compositions, European Patent EP04703841.9, 2003.
3. De Mello, E.B., Gomes, A.S., and Carvalho, I., α- and β-Glucosidase inhibitors: chemical structure and biological activity, Tetrahedron, 62, 10277, 2006.
4. Nash, R.J., Watson, A.A., and Asano, N., Polyhydroxylated alkaloids that inhibit glycosidases, in Alkaloids: Chemical and Biological Perspectives, Vol. 11, Pelletier, S.W., Ed., Elsevier Science Ltd., Oxford, 1996, Chap. 5.
5. Watson, A.A., The Physiology of Swainsonine Production by the Entomopathogenic Fungus Metarhizium anisopliae, PhD thesis, University of London, UK, 1999.
6. Nash, R.J., Rothschild, M., Porter, E.A., Watson, A.A., Waigh, R.D., and Waterman, P.G., Calystegines in Solanum and Datura species and the Death’s Head Hawkmoth (Acherontia atropus), Phytochemistry, 34, 1281, 1993.
7. Nash, R.J. and Watson, A.A., Inhibition of glycosidases by Lepidoptera; roles in the insects and leads to novel compounds? Chemoecology, 5/6, 167, 1995.
8. Molyneux, R.J., James, L.F., Ralphs, M.H., Pfister, J.A., Panter, K.P., and Nash, R.J., Polyhydroxyalkaloid glycosidase inhibitors from poisonous plants of global distribution: analysis and identification, in Plant-Associated Toxins: Agricultural, Phytochemical and Ecological Aspects, Colegate, S.M. and Dorling, P.R., Eds., CAB International, Wallingford, UK, 1994, Chap. 21.
9. Molyneux, R.J., McKenzie, R.A., O’Sullivan, B.M., and Elbein, A.D., Identification of the glycosidase inhibitors swainsonine and calystegine B2 in Weir vine (Ipomoea sp. Q6 [aff calobra]) and correlation with toxicity, J. Nat. Prod., 58, 878, 1995.
10. Huxtable, C.R. and Dorling, P.R., Mannoside storage and axonal dystrophy in sensory neurons of swainsonine-treated rats: morphologenesis of lesions, Acta Neuropathol., 68, 65, 1985.
11. Taguchi, T., Yamashita, E., Mizutani, T., Nakajima, H., Yabuuchi, M., Asano, N., and Miwa, I., Hepatic glycogen breakdown is implicated in the maintenance of plasma mannose concentration, Am. J. Physiol. Endocrinol. Metabol., 288, E534, 2005.
12. Stegelmeier, B.L., Molyneux, R.J., Elbein, A.D., and James, L.F., The lesions of locoweed (Astragalus mollissimus), swainsonine and castanospermine in rats, Vet. Pathol., 32, 289, 1995.
13. Inouye, S., Tsurouka, T., and Niida, T., The structure of nojirimycin, a piperidinose sugar antibiotic, J. Antibiot. Ser. A, 19, 288, 1966.
14. Jones, D.W.C., Nash, R.J., Bell, E.A., and Williams, J.M., Identification of the 2-hydroxymethyl-3,4- dihydroxypyrrolidine (or 1,4-dideoxy-1,4-iminopentitol) from Angylocalyx boutiqueanus and from Arachniodes standishii as the (2R,3R,4S)-isomer by the synthesis of its enantiomer, Tetrahedron Lett., 26, 3125, 1985.
15. Brock, A., Herzfeld, T., Paschke, R., Koch, M., and Draeger, B., Brassicaceae contain nortropane alkaloids, Phytochemistry, 67, 2050, 2006.
16. Renwick, J.H., Anencephaly and spina bifida are usually preventable by avoidance of a specific but unidentified substance present in certain potato tubers, Brit. J. Prev. Med., 26, 67, 1972.
17. Asano, N., Kato, A., Matsui, K., Watson, A.A., Nash, R.J., Molyneux, R.J., Hackett, L., Topping, J., and Winchester, B., The effects of calystegines isolated from edible fruits and vegetables on mammalian liver glycosidases, Glycobiology, 7, 1085, 1997.
18. Wormald, M.R., Nash, R.J., Watson, A.A., Bhadoria, B.K., Langford, R., Sims, M., and Fleet, G.W.J., Casuarine-6-α-d-glucoside from Casuarina equisetifolia and Eugenia jambolana, Carbohydr. Lett., 2, 169, 1996.
19. Kato, A., Adachi, I., Miyauchi, M., Ikeda, K., Komae, T., Kizu, H., Kameda, Y., Watson, A.A., Nash, R., Wormald, M.R., Fleet, G.W.J., and Asano, N., Polyhydroxylated pyrrolidine and pyrrolizidine alkaloids from Hyacinthoides non-scripta and Scilla campanulata, Carbohydr. Res., 316, 95, 1999.
20. Harris, C.M., Schneider, M.J., Ungemach, F.S., Hill, J.E., and Harris, T.M., Biosynthesis of the toxic indolizidine alkaloids slaframine and swainsonine in Rhizoctonia leguminicola: metabolism of 1-hydroxyindolizidines, J. Am Chem. Soc., 110, 940, 1988.
21. Dennis, J.W., Granovsky, M., and Warren, C.E., Glycoprotein glycosylation and cancer progression, Biochim. Biophys. Acta, 1473, 21, 1999.
22. Woynarowska, B., Wikiel, H., Sharma, M., Carpenter, N., Fleet, G.W.J., and Bernacki, R.J., Inhibition of human ovarian carcinoma cell- and hexosaminidase- mediated degradation of extracellular matrix by sugar analogs, Anticancer Res., 12, 161, 1992.
23. Lipinski, C.A., Lombardo, F., Dominy, B.W., and Feeney, P.J., Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings, Adv. Drug Del. Rev., 46, 3, 2001.
24. Carroll, M.W. and Nash, R.J., A sweeter future for imino sugars, SCRIP Mag., September, 16, 2005.
25. Winchester, B., Lysosomal metabolism of glycoproteins, Glycobiology, 15, 1R, 2005.
26. Molyneux, R.J., Gardner, D.R., James, L.F., and Colegate, S.M., Polyhydroxy alkaloids: chromatographic analysis, J. Chromatogr. A, 967, 57, 2002.
27. Thursby-Pelham, H.C., Suspected Scilla non-scripta (Bluebell) poisoning in cattle, Vet. Rec., 80, 709, 1967.
28. Chen, T-M., George, R.C., Weir, J.L., and Leapheart, T., Thermospray liquid chromatographic-mass spectrometric analysis of castanospermine-related alkaloids in Castanospermum australe, J. Nat. Prod., 53, 359, 1990.
29. Donaldson, M.J., Broby, H., Adlard, M.W., and Bucke, C., Analysis of certain alkaloids, Phytochem. Anal., 1, 1, 1990.
30. Scholl, Y., Asano, N., and Dräger, B., Automated multiple development thin layer chromatography for calystegines and their biosynthetic precursors, J. Chromatogr. A, 928, 217, 2001.
31. Hohenschutz, L.D., Bell, E.A., Jewess, P.J., Leworthy, D.P., Pryce, R.J., Arnold, E., and Clardy, J., Castanospermine, a 1,6,7,8-tetrahydroxy-octahydroindolizidine alkaloid from seeds of Castanospermum australe, Phytochemistry, 20, 811, 1981.
32. Matsumura, T., Kasai, M., Hayashi, T., Arisawa, M., Momose, Y., Arai, I., Amagaya, S., and Komatsu, Y., α-Glucosidase inhibitors from Paraguayan natural medicine, Nangapiry, the leaves of Eugenia uniflora, Pharmaceut. Biol., 38, 302, 2000.
33. Colegate, S.M., Dorling, P.R., and Huxtable, C.R., A spectroscopic investigation of swainsonine, a specific inhibitor of α-mannosidase isolated from Swainsona canescens, Aust. J. Chem., 32, 2257, 1979.
34. Watson, A.A., Nash, R.J., Wormald, M.R., Harvey, D.J., Dealler, S., Lees, E., Asano, N., Kizu, H., Kato, A., Griffiths, R.C., Cairns, A.J., and Fleet, G.W.J., Glycosidase-inhibiting pyrrolidine alkaloids from Hyacinthoides non-scripta, Phytochemistry, 46, 255, 1997.
35. Wormald, M.R., Nash, R.J., White, J.D., Molyneux, R.J., and Fleet, G.W.J., Configurational and conformational analysis of pyrrolizidines: resolution of the uncertainties concerning the structural identification of certain naturally occurring 7a-epi-alexines, Tetrahedron Asymmetr., 9, 2549, 1998.