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Castanospermine, Swainsonine and Related Polyhydroxy Alkaloids: Structure, Distribution and Biological Activity

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Plant Nitrogen Metabolism

Part of the book series: Recent Advances in Phytochemistry ((RAPT,volume 23))

Abstract

Alkaloids which are inhibitors of glycosidases are now believed to be widespread in plants and microorganisms. Those isolated to date carry several hydroxyl substituents on a ring in a configuration that suggests a structural resemblance to monosaccharides. Despite their relatively recent detection (most have been discovered during the last ten years), they are now providing molecular biologists with tools with which to probe many hitherto intractable problems of molecular biology, including cancer metastasis, viral infectivity and the immune response. One, castanospermine, is under evaluation as a drug for the clinical management of HIV infection (AIDS). This paper outlines their structural range, natural distribution and biological activity.

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References

  1. FELLOWS, L.E. 1986. The biological activity of polyhydroxyalkaloids from plants. Pestic. Sci. 17: 602–606.

    Article  Google Scholar 

  2. FELLOWS, L.E., FLEET, G.W.J. 1988. Alkaloidal glycosidase inhibitors from plants. In Natural Products Isolation. (G.H. Wagman, R. Cooper, eds.), Elsevier, Amsterdam, pp. 540–560.

    Google Scholar 

  3. NASH, R.J., L.E. FELLOWS, J.V. DRING, G.W.J. FLEET, A.E. DEROME, T.A. HAMOR, A.M. SCOFIELD, D.J. WATKIN. 1988. Isolation from Alexa leiopetala and X-ray crystal structure of alexine, (1R,2R,3R,7S,8S)-3-hydroxymethyl-l,2,7-trihydroxypyrrolizidine [(2R,3R,4R,5S,6S)-2-hydroxymethyl-l-azabicyclo[3.3.0]octan-3,4,6-triol], a unique pyrrolizidine alkaloid. Tetrahedron Lett. 29: 2487–2490.

    Article  Google Scholar 

  4. SHIBATA, T., O. NAKAYAMA, Y. TSURUMI, M. OKUHARA, H. TERAN0, M. KOHSAKA. 1988. A new immuno-modulator, FR-900483. J. Antibiot. 61: 296–301.

    Google Scholar 

  5. NASH, R.J., L.E. FELLOWS, A.C. PLANT, G.W.J. FLEET, A.E. DEROME, P.D. BAIRD, M.P. HEGARTY, A.M. SCOFIELD. 1988. Isolation from Castanospermum australe and X-ray crystal structure of 3,8-diepialexine, (1R,2R,3S,7S,8R)-3-hydroxymethyl-1,2,7-trihydroxypyrrolizidine [(2S,3R,4R,5S,6R)-2-hydroxymethyl-1-azabicyclo [3.30]octan-3,4,6-triol]. Tetrahedron 44: 5959–5964.

    Article  Google Scholar 

  6. INOUYE, S., T. TSURUOKA, T. NTIDA. 1966. The structure of nojirimycin, a piperidinose sugar antibiotic. J. Antiobiot. Ser. A 19: 288–292.

    Google Scholar 

  7. ISHIDA, N., K. KUMAGAI, T. NIIDA, T. TSURUOKA, H. YUMOTO. 1967. Nojirimycin, a new antibiotic. II. Isolation, characterization and biological activity. J. Antibiot. 20: 66–71.

    Google Scholar 

  8. NIWA, T., S. INOUYE, T. TSURUOKA, Y. KOAZE, T. NIIDA. 1970. Nojirimycin as a potent inhibitor of glucosidase. Agric. Biol. Chem. 34: 966–968.

    Article  Google Scholar 

  9. REESE, E.T., F.W. PARRISH. 1971. Nojirimycin and D-glucono-1,5-lactone as inhibitors of carbohydrases. Carbohydr. Res. 18: 381–388.

    Article  Google Scholar 

  10. NIWA, T., T. TSURUOKA, H. GOI, Y. KODAMA, J. ITOH, S. INOUYE, Y. YAMADA, T. NIIDA, M. NOBE, Y. OGAWA. 1984. Novel glycosidase inhibitors, nojirimycin B and D-mannonic-δ-lactam. J. Antibiot. 37: 1579–1586.

    Google Scholar 

  11. MIYAKE, Y., M. EBATA. 1987. Galactostatin, a new β-galactosidase inhibitor from Streptomyces lydicus. J. Antibiot. 40: 122–123.

    Google Scholar 

  12. SCHMIDT, D.D., W. FROMMER, L. MULLER, E. TRUSCHEIT. 1979. Glucosidase Inhibitoren aus Bazillen. Naturwissenschaften 66: 584–585.

    Article  ADS  Google Scholar 

  13. MURAO, S., S. MIYATA. 1980. Isolation and characterization of a new trehalase inhibitor, S-GI. Agric. Biol. Chem. 44: 219–221.

    Article  Google Scholar 

  14. GUENGERICH, F.P., S.J. DIMARI, H.P. BROQUIST. Isolation and characterization of a 1-pyridine fungal alkaloid. J. Am. Chem. Soc. 95: 2055–2056.

    Google Scholar 

  15. SCHNEIDER, M.J., F.S. UNGEMACH, H.P. BROQUIST, T.M. HARRIS. 1983. (IS,2R,8R,8aR)-l,2,8-trihydroyoctahydroindolizine (swainsonine), an α-mannosidase inhibitor from Rhizoctonia leguminicola. Tetrahedron 39: 29–32.

    Article  Google Scholar 

  16. HINO, M., O. NAKAYAMA, Y. TSURUMI, K. ADACHI, T. SHIBATA, H. TERANO, M. KOHSAKA, H. AOKI, H. IMANAKA. 1985. Studies of an immunomodulator, swainsonine. 1. Enhancement of immune response by swainsonine in vitro. J. Antibiot. 38: 926–935.

    Google Scholar 

  17. YAGI, M., T. KOUNO, Y. AOYAGI, H. MURAI. 1976. The structure of moranoline, a piperidine alkaloid from Morus species. Nippon Nogeikagaku Kaishi 50: 571–572.

    Article  Google Scholar 

  18. MURAI, H., K. OHATA, H. ENOMOTO, Y. YOSHIKUNI, T. KONO, M. YAGI. 1977. 2-Hydroxymethyl-3,4,5-trihydroxypiperidine and extraction process for its manufacture. Ger. Offen. 2,656,602, 30th June.

    Google Scholar 

  19. KITE, G.C., L.E. FELLOWS, G.W.J. FLEET, P.S. LIU, A.M. SCOFIELD, N.G. SMITH. 1988. Alpha-homonojirimycin (2,6-dideoxy-2,6-imino-D-glycero-L-gulo-heptitol) from Omphalea diandra L.: Isolation and glucosidase inhibition. Tetrahedron. Lett. 29: 6483–6486.

    Article  Google Scholar 

  20. WELTER, A., J. JADOT, G. DARDENNE, M. MARLIER, J. CASIMIR. 1976. 2,5-Hydroxymethyl 3,4-dihydroxypyrrolidine dans les feuilles de Derris elliptica. Phytochemistry 15: 747–749.

    Article  Google Scholar 

  21. FLEET, G.W.J., P.W. SMITH. 1985. Enantiospecific syntheses of deoxymannojirimycin, fagomine and 2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine from D-glucose. Tetrahedron Lett. 26: 1469–1472.

    Article  Google Scholar 

  22. EVANS, S.V., A.M.R. GATEHOUSE, L.E. FELLOWS. 1985. Detrimental effects of 2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine in some tropical legumes on larvae of the bruchid Callosobruchus maculatus. Entomol. Exp. Appl. 37: 257–261.

    Article  Google Scholar 

  23. SCOFIELD, A.M. L.E. FELLOWS, R.J. NASH, G.W.J. FLEET. 1986. Inhibition of mammalian disac-charidases by polyhydroxy alkaloids. Life Sci. 39: 645–650.

    Article  Google Scholar 

  24. HORN, J.M., D.C. LEES, N.G. SMITH, R.J. NASH, L.E. FELLOWS, E.A. BELL. 1986. The Urania/ Omphalea interaction: host plant secondary chemistry. In Proceedings of the 6th International Symposium of Plant-Insect Relationships. (V. Labeyrie, G. fabres, D. Lachaise, eds.), Dr. W. Junk, Dordrecht, p. 394.

    Google Scholar 

  25. BROWER, L.P., J. VAN, Z. BROWER, J.M. CORVINA. 1967. Plant poisons in a terrestrial food chain. Proc. Nat. Acad. Sci. USA 57: 893–898.

    Article  ADS  Google Scholar 

  26. FELLOWS, L.E., E.A. BELL, D.G. LYNN, F. PILKIEWICZ, I. MIURA, K. NAKANISHI. 1979. Isolation and structure of an unusual cyclic amino alditol from a legume. J. Chem. Soc. Chem. Commun. 977–978.

    Google Scholar 

  27. FUHRMANN, U., E. BAUSE, G. LEGLER, H. PLOEGH. 1984. Novel mannosidase inhibitor blocking conversion of high mannose to complex oligosaccharides. Nature 307: 755–758.

    Article  ADS  Google Scholar 

  28. EVANS, S.V., L.E. FELLOWS, T.K.M. SHING, G.W.J. FLEET. 1985. Glycosidase inhibition by plant alkaloids which are structural analogues of monosaccharides. Phytochemistry 24: 1953–1955.

    Article  Google Scholar 

  29. LEGLER, G., S. POHL. 1986. Synthesis of 5-amino-5-deoxy-D-galactopyranose and 1,5-dideoxy-l,5-imino-D-galactitol, and their inhibition of α- and β-D-galactosidases. Carbohydr. Res. 155: 119–129.

    Article  Google Scholar 

  30. POLHILL, R.M. 1981. Galegeae. In Advances in Legume Systematics. (R.M. Polhill, P.H. Raven, eds.), Royal Botanic Garden, Kew, Richmond, United Kingdom, pp. 357–363.

    Google Scholar 

  31. COLEGATE, S.M., P.R. DORLING, C.R. HUXTABLE. 1979. A spectroscopic investigation of swainsonine: an α-mannosidase inhibitor isolated from Swainsona canescens. Aust. J. Chem. 32: 2257–2264.

    Article  Google Scholar 

  32. ELBEIN, A.D., P.R. DORLING, K. VOSBECK. M. HORISBERGER. 1982. Swainsonine prevents the processing of the oligosaccharide chains of influenza virus hemagglutinin. J. Biol. Chem. 257: 1573–1576.

    Google Scholar 

  33. MOLYNEUX, R.J., L.F. JAMES. 1981. Loco intoxication: indolizidine alkaloids of spotted loco-weed Astragalus lentiginosus. Science 216: 190–191.

    Article  ADS  Google Scholar 

  34. HOHENSCHUTZ, L.D., E.A. BELL, P.J. JEWESS, D.P. LEWORTHY, R.J. PRYCE, E. ARNOLD, J. CLARDY. 1981. Castanospermine, a 1,6,7,8-tetrahydro-indolizine alkaloid from seeds of Castanospermum australe. Phytochemistry 20: 811–814.

    Article  Google Scholar 

  35. SASAK, V.W., J.M. ORDOVAS, A.D. ELBEIN, R.W. BERNINGER. 1985. Castanospermine inhibits glucosidase I and glycoprotein secretion in human hepatoma cells. Biochem. J. 232: 759–766.

    Google Scholar 

  36. GEESINK, R. 1981. Tephrosieae. Op. cit. Reference 30, pp. 245–260.

    Google Scholar 

  37. KINGHORN, A.D., R.A. HUSSAIN, E.F. ROBBINE, M.F. BALADRIN, C.H. STIRTON. 1988. Alkaloid distribution in seeds of Ormosia, Pericopsis and Haplormosia. Phytochemistry 27: 439–444.

    Article  Google Scholar 

  38. NASH, R.J., E.A. BELL, J.M. WILLIAMS. 1985. 2-Hydroxymethyl-3,4-dihydroxypyrrolidine in fruits of Angylocalyx boutiqueanus. Phytochemistry 24: 1620–1622.

    Article  Google Scholar 

  39. JONES, D.W.C., R.J. NASH, E.A. BELL, J.M. WILLIAMS. 1985. Identification of the 2-hydroxymethyl-3,4-dihydroxypyrrolidine (or 1,4-dideoxy1,4-iminopentitol) from Angylocalyx boutiqueanus and from Arachnoides standishii as the (2R,3R,4S) isomer by the synthesis of its enantiomer. Tetrahedron Lett. 26: 3125–3126.

    Article  Google Scholar 

  40. FLEET, G.W.J., S.J. NICHOLAS, P.W. SMITH, S.V. EVANS, L.E. FELLOWS, R.J. NASH. 1985. Potent competitive inhibition of α-galactosidase and α-glucosidase activity by 1,4-dideoxy-1,4-iminopentitols: syntheses of 1,4-didieoxy-1,4-imino-D-lyxitol and of both enantiomers of 1,4-dideoxy-1,4-iminoarabinitol. Tetrahedron Lett. 26: 3127–3130.

    Article  Google Scholar 

  41. MANNING, K.S., D.G. LYNN, J. SHABANOWITZ, L.E. FELLOWS, M. SINGH, B.D. SCHRIRE. 1985. A glucuronidase inhibitor from the seeds of Baphia racemosa: application of fast atom bombardment coupled with collision activated dissociation in natural product structure assignment. J. Chem. Soc. Chem. Commun. 127–129.

    Google Scholar 

  42. EVANS, S.V., A.R. HAYMAN, L.E. FELLOWS, T.K.M. SHING, A.E. DEROME, G.W.J. FLEET. 1985. Lack of glycosidase inhibition by, and isolation from Xanthocercis zambesiaca (Leguminoasae) of 4-0-(beta-D-glucopyranosyl)-fagomine, [1,2,5-trideoxy-4-0-(beta-D-glucopyranosyl)-l,5-imino-D-arabino-hexitol], a novel glucoside of a polyhydroxylated piperidine alkaloid. Tetrahedron Lett. 26: 1465–1468.

    Article  Google Scholar 

  43. NASH, R.J., E.A. BELL, G.W.J. FLEET, R.H. JONES, J.M. WILLIAMS. 1985. The identification of a hydroxylated pyrrolidine derivative from Castanospermum australe. J. Chem. Soc. Chem. Commun. 738–740.

    Google Scholar 

  44. MOLYNEUX, R.J., J.N. ROITMAN, G. DUNNHEIM, T. SZUMILO, A.D. ELBEIN. 1986. 6-Epicastano-spermine, a novel indolizidine alkaloid that inhibits α-glucosidase. Arch. Biochem. Biophys. 251: 450–457.

    Article  Google Scholar 

  45. NASH, R.J., L.E. FELLOWS, J.V. DRING, C.H. STIRTON, D. CARTER, M.P. HEGARTY, E.A. BELL. 1988. Castanospermine in Alexa species. Phytochemistry 27: 1403–1404.

    Article  Google Scholar 

  46. SMITH, A.G., J.C. BRIDEN, G.E. DREWRY. 1973. Phanerozoic world maps. Spec. Pap. Palaeontol. 12: 1–42.

    Google Scholar 

  47. SCHWARTZ, R.T., R. DATEMA. 1984. Inhibitors of trimming: new tools in glycoprotein research. Trends Biochem. Sci. 9: 32–34.

    Article  Google Scholar 

  48. FUHRMANN, U., E. BAUSE, H. PLOEGH. 1985. Inhibitors of oligosaccharide processing. Biochim. Biophys. Acta 825: 95–110.

    Google Scholar 

  49. ELBEIN, A.D., R.J. MOLYNEUX. 1987. The chemistry and biochemistry of simple indolizidine and related polyhydroxy alkaloids. In Alkaloids: Chemical and Biological Perspectives. (S.W. Pelletier, ed.), Wiley Interscience, New York. Vol. 5, pp. 1–54.

    Google Scholar 

  50. TYMS, A.S., E.M. BERRIE, T.A. RYDER, R.J. NASH, M.P. HEGARTY, D.L. TAYLOR, M.A. MOBBERLEY, J.M. DAVIS, E.A. BELL, D.J. JEFFRIES, D. TAYLOR-ROBINSON, L.E. FELLOWS. 1987. Castanospermine and other plant alkaloid inhibitors of glucosidase activity block the growth of HIV. Lancet, 1025–1026.

    Google Scholar 

  51. GRUTERS, R.A., J.J. NEEFJES, M. TERSMETTE, R.E.Y. DE GOEDE, A. TULP, H.G. HUISMAN, F. MIEDEMA, H.L. PLOEGH. 1987. Interference with HIV-induced syncytium formation and viral infectivity by inhibitors of trimming glucosidase. Nature 330: 74–77.

    Article  ADS  Google Scholar 

  52. WALKER, B.D., M. KOWALSKI, W.C. GOH, K. KOZARSKY, M. KRIEGER, C. ROSEN, L. ROHRSCHNEIDER, W.A. HASELTINE, J. SODROSKI. 1987. Inhibition of human immunodeficiency virus syncytium formation and virus replication by castanospermine. Proc. Natl. Acad. Sci. USA 84: 8120–8124.

    Article  ADS  Google Scholar 

  53. SUNKARA, P.S., T.L. BOLIN, P.S. LIU, A.A. SJOERDSMA. 1987. Antiretroviral activity of castanospermine and deoxynojirimycin, specific inhibitors of glycoprotein processing. Biochem. Biophys. Commun. 148: 206–210.

    Article  Google Scholar 

  54. TAYLOR, D.L., L.E. FELLOWS, G.H. FARRAR, R.J. NASH, D. TAYLOR-ROBONSON, M.A. MOBBERLEY, T.A. RYDER, D.J. JEFFRIES, A.S. TYMS. 1988. Loss of cytomegalovirus infectivity after reaction with castanospermine or related plant alkaloids relates to aberrant glycoprotein synthesis. Antiviral Res. 10: 11–26.

    Article  Google Scholar 

  55. PAN, Y.T., H. HORI, R. SAUL, B.A. SANFORD, R.J. MOLYNEUX, A.D. ALBEIN. 1983. Castanospermine inhibits the processing of the oligosaccharide portion of the influenza viral hemagglutinin. Biochemistry 22: 3975–3984.

    Article  Google Scholar 

  56. BURKE, B., K. MATLIN, E. BAUSE, G. LEGLER, N. PEYRIERAS, H. PLOEGH. 1984. Inhibition of N-linked oligosaccharide trimming does not interfere with surface expression of certain integral membrane proteins. EMBO J. 3: 551–556.

    Google Scholar 

  57. BOSCH, V., R.T. SCHWARZ. 1984. Processing of gPr92env, the precursor to the glycoproteins of Rous sarcoma virus: use of inhibitors of oligosaccharide trimming and glycoprotein transport. Virology 132: 95–109.

    Article  Google Scholar 

  58. ROMERO, P.A., R. DATEMA, R.T. SCHWARZ. 1983. N-methyl-l-deoxynojirimycin, a novel inhibitor of glycoprotein processing and its effect on fowl plague virus maturation. Virology 130: 238–242.

    Article  Google Scholar 

  59. WARREN, L., C.A. BUCK. G.P. TUSGYNSKI. 1978. Glycopeptide changes and malignant transformation: a possible role for carbohydrates in malignant behavior. Nature 253: 457–460.

    Google Scholar 

  60. SANTER, U.V., M.C. GLICK. 1979. Partial structure of a membrane glycoprotein from virus transformed hamster cells. Biochemistry 18: 2533–2540.

    Article  Google Scholar 

  61. COLLARD, J.G., W.P. VAN BEEK, J.W.G. JANSSEN, J.F. SCHIJVEN. 1985. Transfection by human oncogenes: concomitant induction of tumori-genicity and tumor-associated membrane alteration. Int. J. Cancer 35: 207–214.

    Article  Google Scholar 

  62. HADWIGER, A., H. NIEMANN, A. KABISCH, H. BAUER, T. TAMURA. 1986. Appropriate glycosylation of the fms gene product is a prerequisite for its transforming potency. EMBO J. 5: 689–694.

    Google Scholar 

  63. OSTRANDER, G.K., N.K. SCRIBNER, L.R. ROHRSCHNEIDER. 1988. Inhibition of v-fms-induced tumor growth in nude mice by castanospermine. Cancer Res. 48: 1091–0194.

    Google Scholar 

  64. DESANTIS, R., U.V. SANTER, M.C. GLICK. 1987. NIH 3T3 cells transfected with human tumor DNA lose the transformed phenotype when treated with swainsonine. Biochem. Biophys. Res. Commun. 142: 348–353.

    Article  Google Scholar 

  65. HUMPHRIES, M.J., K. MATSUMOTO, S.L. WHITE, K. OLDEN. 1986. Oligosaccharide modification by swainsonine treatment inhibits pulmonary colonization by B16-F10 murine melanoma cells. Proc. Nat. Acad. Sci. USA 83: 1752–1756.

    Article  ADS  Google Scholar 

  66. HUMPHRIES, M.J., K. MATSUMOTO, S.L. WHITE, K. OLDEN. 1986. Inhibition of experimental metastasis by castanospermine in mice: blockage of two distinct stages of tumor colonization by oligosaccharide processing inhibitors. Cancer Res. 46: 5215– 5222.

    Google Scholar 

  67. HUMPHRIES, M.J., K. MATSUMOTO, S.L. WHITE, R.J. MOLYNEUX, K. OLDEN. 1988. Augmentation of murin natural killer cell activity by swainsonine, a new antimetastatic immunomodulator. Cancer Res. 48: 1410–1415.

    Google Scholar 

  68. DENNIS, J.W. Effects of swainsonine and poly-inosinic: polycytidylic acid on murine tumor cell growth and metastasis. Cancer Res. 46: 5131–5136.

    Google Scholar 

  69. KINO, T., N. INAMURA, K. NAKAHARA, S. KIYOTO, T. GOTO, H. TERANO, M. KOHSAKA, H. AOKI, H. IMANAKA. 1985. Studies of an immunomodulator, swainsonine. II. Effect of swainsonine on mouse immunodeficient system and experimental murine tumor. J. Antibiot. 37: 936–940.

    Google Scholar 

  70. WALL, K.A., J.D. PIERCE, A.D. ELBEIN. 1988. Inhibitors of glycoprotein processing alter T-cell proliferative responses to antigen and to interleukin 2. Proc. Nat. Acad. Sci. USA 85: 5644–5648.

    Article  ADS  Google Scholar 

  71. BERNACKI, R., M.J. NIEDBALA, W. KORYTNYK. 1985. Glycosidases in cancer and invasion. Cancer Metast. Rev. 4: 81–102.

    Article  Google Scholar 

  72. HORI, H., Y.T. PAN, R.J. MOLYNEUX, A.D. ELBEIN. 1984. Inhibition of plant N-linked oligosaccharides by castanospermine. Arch. Biochem. Biophys. 228: 525–533.

    Article  Google Scholar 

  73. SZUMILO, T., G.P. KAUSHAL, H. HORI, A.D. ELBEIN. 1986. Purification and properties of a glycoprotein processing α-mannosidase from mung bean seedlings. Plant Physiol. 81: 383–389.

    Article  Google Scholar 

  74. CHRISPEELS, M.J., A. VITALE. 1985. Abnormal processing of the modified oligosaccharide side chains of phytohemagglutinin in the presence of swainsonine and deoxynojirimycin. Plant Physiol. 78: 704–709.

    Article  Google Scholar 

  75. YAMASAKI, Y., H. KONNO. 1985. Three forms of α-glucosidase from suspension-cultured rice cells. Agric. Biol. Chem. 49: 3383–3390.

    Article  Google Scholar 

  76. McGEE, C.M, D.R. MURRAY. 1986. Comparative, studies of acid glycosidases from three legumes. Ann. Bot. (Lond.) 57: 179–190.

    Google Scholar 

  77. LIZOTTE, P.A., J.E. POULTON. 1988. Catabolism of cyanogenic glycosides by vicianin hydrolase from Squirrel’s Foot fern (Davalia trichomanoides Blume). Plant Physiol. 86: 322–324.

    Article  Google Scholar 

  78. SAKURAI, N., Y. MASUDA. 1978. Auxin-induced changes in barley coleoptile cell wall composition. Plant Cell Physiol. 19: 1217–1223.

    Google Scholar 

  79. WALLNER, S.J., D.J. NEVINS. 1974. Changes in cell walls associated with cell separation in suspension cultures of Paul’s Scarlet Rose. J. Exp. Bot. 25: 1020–1029.

    Article  Google Scholar 

  80. NAGAHASHI, G., P.M. BARNETT, S.I. TU, J. BROUILLETTE. 1986.Purification of primary cell walls from corn roots: inhibition of cell-wall associated enzymes with indolizidine alkaloids. In Regulation of Carbon and Nitrogen Reduction and Utilization in Maize. (J.C. Shannon, D.P. Knievel, C.D. Boyer, eds.), Am. Soc. Plant Physiologists, Rockville, Maryland, pp. 289–293.

    Google Scholar 

  81. ROSENFIELD, C.L., P. MATILE. 1979. Glycosidases in pear pollen tube development. Plant Cell Physiol. 20: 605–613.

    Google Scholar 

  82. MÜLLER, L. 1986. Microbial glycosidase inhibitors. In Microbial Products II. (H. Pape, H.J. Rehm, eds.), VCH Verlagesellschaft, Weinheim, pp. 532–567.

    Google Scholar 

  83. SAMULITIS, B.K., T. GODA, S.M. LEE, O. K0LD0VSKI. 1987. Inhibitory mechanism of acarbose and 1-deoxynojirimycin derivatives on carbohydrases in rat small intestine. Drugs Exp. Clin. Res. 13: 517–524.

    Google Scholar 

  84. RHINEHART, G.L., K.M. ROBINSON, A.J. PAYNE, M.E. WHEATELY, J.L. FISHER, P.S. LIU, W. CHENG. 1987. Castanospermine blocks the hyperglycemic response to carbohydrates in vivo: a result of intestinal disaccharidase inhibition. Life Sci. 41: 2325–2331.

    Article  Google Scholar 

  85. NASH, R.J., K.A. FENTON. A.M.R. GATEHOUSE, E.A. BELL. 1986. Effects of the plant alkaloid castanospermine as an antimetabolite of storage pests. Entomol. Exp. Appl 42: 71–77.

    Article  Google Scholar 

  86. CAMPBELL, B.C., R.J. MOLYNEUX, K.C. JONES. 1987. Differential inhibition by castanospermine of various insect disaccharidases. J. Chem. Ecol. 13: 1759–1770.

    Article  Google Scholar 

  87. BLANEY, W.M., M.S.J. SIMMONDS, S.V. EVANS, L.E. FELLOWS. 1984. The role of the plant secondary compound 2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine as a feeding inhibitor for insects. Entomol. Exp. Appl. 36: 209–216.

    Article  Google Scholar 

  88. DREYER, D.L., K.C. JONES, R.J. MOLYNEUX. 1985. Feeding deterrency of some pyrrolizidine, indoolizidine and quinolizidine alkaloids towards pea aphid (Acyrthosiphon pisum) and evidence for phloem transport of the indolizidine alkaloid swainsonine. J. Chem. Ecol. 11: 1045– 1051.

    Article  Google Scholar 

  89. BLANEY, W.M. 1974. Electrophysiological responses of the terminal sensilla on the maxillary palps Locusta migratoria to some electrolytes and non-electrolytes. J. Exp. Biol. 60: 275–293.

    Google Scholar 

  90. SIMMONDS, M.S.J., W.M. BLANEY. 1984. Some effects of azadirachtin on lepidopterous larvae. In Proceedings of the 2nd International Neem Conference. (H. Schmutterer, K.R.S. Ascher, eds.), GTZ Eschborn, pp. 163–180.

    Google Scholar 

  91. BLANEY, W.M., M.S.J. SIMMONDS, S.V. LEY, P.S. JONES. 1988. Insect antifeedants: a behavioral and electrophysiological investigation of natural and synthetically derived clerodane diterpenoids. Entomol. Exp. Appl. 46: 267–274.

    Article  Google Scholar 

  92. FLEET, G.W.J., A.N. SHAW, S.V. EVANS, L.E. FELLOWS. 1985. Synthesis from glucose of 2,5-dideoxy-1,5-imino-L-fucitol, a potent α-L-fucosidase inhibitor. J. Chem. Soc. Chem. Commun. 841–842.

    Google Scholar 

  93. INOUYE, S., T. TSURUOKA, T. ITO, T. NIIDA. 1968. Structure and synthesis of nojirimycin. Tetrahedron 23: 2125–2144.

    Article  Google Scholar 

  94. HARRIS, C.M., M.J. SCHNEIDER, F.S. UNGEMACH, J.E. HILL, T.M. HARRIS. 1988. Biosynthesis of the toxic indolizidine alkaloids slaframine and swainsonine in Rhizoctonia leguminicola: metabolism of 1-hydroxyindolizidines. J. Am. Chem. Soc. 110: 940–949.

    Article  Google Scholar 

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Authors and Affiliations

  1. Jodrell Laboratory, Royal Botanic Gardens, TW9 3DS, Kew, UK

    Linda E. Fellows, Geoffrey C. Kite, Robert J. Nash & Monique S. J. Simmonds

  2. University of London Wye College Wye, TN25 5AH, Wye, Ashford Kent, UK

    Anthony M. Scofield

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  1. Linda E. Fellows
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  2. Geoffrey C. Kite
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  3. Robert J. Nash
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  4. Monique S. J. Simmonds
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  5. Anthony M. Scofield
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Editors and Affiliations

  1. University of lowa, Iowa City, Iowa, USA

    Jonathan E. Poulton

  2. University of South Florida, Tampa, Florida, USA

    John T. Romeo

  3. University of California, Davis, California, Davis, USA

    Eric E. Conn

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© 1989 Plenum Press, New York

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Fellows, L.E., Kite, G.C., Nash, R.J., Simmonds, M.S.J., Scofield, A.M. (1989). Castanospermine, Swainsonine and Related Polyhydroxy Alkaloids: Structure, Distribution and Biological Activity. In: Poulton, J.E., Romeo, J.T., Conn, E.E. (eds) Plant Nitrogen Metabolism. Recent Advances in Phytochemistry, vol 23. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-0835-5_11

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  • DOI: https://doi.org/10.1007/978-1-4613-0835-5_11

  • Publisher Name: Springer, Boston, MA

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