Biological activities of the nortropane alkaloid, calystegine b2, and analogs: Structure-function relationships

Journal of Natural Products

Volumn 59, Issue 12, 1996, Pages 1137-1142

  Goldmann, Ariette ^a   Message, Brigitte ^a   Tepfer, David ^a   Molyneux, Russell J ^b   Duclos, Olivier ^c   Boyer, François Didier ^c   Pan, Y T ^d   Elbein, Alan D ^d  

^a CEMAGREF   (France)

^b WESTERN REGIONAL RESEARCH CENTER   (United States)

^c UNIVERSITÉ PARIS DESCARTES   (France)

^d UNIVERSITY OF ARKANSAS FOR MEDICAL SCIENCES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ALPHA GALACTOSIDASE; BETA GLUCOSIDASE; CALYSTEGINE B2; GLYCOSIDASE INHIBITOR; NORTROPANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; ENANTIOMER; FABRY DISEASE; NONHUMAN; PLANT; PSEUDOMONAS; SINORHIZOBIUM MELILOTI; SOIL MICROFLORA; STRUCTURE ACTIVITY RELATION;

ALPHA-GALACTOSIDASE; BACTERIA; DNA, BACTERIAL; ENZYME INHIBITORS; GLYCOSIDE HYDROLASES; NORTROPANES; PLANT ROOTS; PLANTS, MEDICINAL; PSEUDOMONAS; SEEDS; SINORHIZOBIUM MELILOTI; SOLANACEOUS ALKALOIDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030459691     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np960409v     Document Type: Article

References (47)

1. These compounds were originally named as "calystegins", but the term "calystegines" has subsequently been adopted by certain research groups. Because the former name was previously assigned to a different class of compounds (Chu, J.-H.; Chian, Y.-H. Chem. Zentralblatt. 1960, 131, 1859-1860), and in order to conform with the convention used for naming other polyhydroxy alkaloids, the latter term is now preferred.
2. Goldmann, A.; Milat, M. L.; Ducrot, P. H.; Lallemand, J.-Y.; Maille, M.; Lepingle, A.; Charpin, I.; Tepfer, D. Phytochemistry 1990, 29, 2125-2127.
3. Ducrot, P.-H.; Lallemand, J.-Y. Tetrahedron Lett. 1990, 31, 3879-3882.
4. Tepfer, D.; Goldmann, A.; Fleury, V.; Maille, M.; Message, B.; Pamboukdjian, N.; Boivin, C.; Dénarié, J.; Rosenberg, C.; Lallemand, J.-Y.; Descoins, C.; Charpin, I.; Amarger, N. In Molecular Genetics of Plant-Microbe Interactions; Palacios, R., Verma, D., Eds.; APS Press: St. Paul, 1988; pp 139-144.
5. Molyneux, R. J.; McKenzie, R. A.; O'Sullivan, B. M.; Elbein, A. D. J. Nat. Prod. 1995, 58, 878-886.
6. Dräger, B.; Funck, C.; Höhler, A.; Mrachatz, G.; Nahrstedt, A.; Portsteffen, A.; Schaal, A.; Schmidt, R. Plant Cell Tissue Organ Cult. 1994, 38, 235-240.
7. Dräger, B.; van Almsick, A.; Mrachatz, G. Planta Med. 1995, 61, 577-579.
8. Nash, R.J.; Rothschild, M.; Porter, E. A.; Watson, A. A.; Waigh, R. D.; Waterman, P. G. Phytochemistry 1993, 34, 1281-1283.
9. Asano, N.; Kato, A.; Oseki, K.; Kizu, H.; Matsui, K. Eur. J. Biochem. 1995, 229, 369-376.
10. Asano, N.; Tomioka, E.; Kizu, H.; Matsui, K. Carbohydr. Res. 1994, 253, 235-245.
11. Asano, N.; Oseki, K.; Tomioka, E.; Kizu, H.; Matsui, K. Carbohydr. Res. 1994, 259, 243-255.
12. Duclos, O.; Mondange, M.; Duréault, A.; Depezay, J.-C. Tetrahedron Lett. 1992, 33, 8061-8064.
13. Boyer, F.-D.; Lallemand, J.-Y. Synlett 1992, 969-971.
14. Boyer, F.-D.; Lallemand, J.-Y. Tetrahedron 1994, 50, 10443-10458.
15. Boyer, F.-D.; Ducrot, P.-H.; Henryon, V.; Soulié, J.; Lallemand, J.-Y. Synlett 1992, 357-359.
16. Johnson, C. R.; Bis, S. J. J. Org. Chem. 1995, 60, 616-623.
17. Tepfer, D.; Goldmann, A.; Pamboukdjian, N.; Maille, M.; Lépingle, A.; Chevalier, D.; Dénarié, J.; Rosenberg, C. J. Bacteriol. 1988, 170, 1153-1161.
18. Boivin, C.; Malpica, C.; Rosenberg, C.; Dénarié, J.; Goldmann, A.; Fleury, V.; Maille, M.; Message, B.; Tepfer, D. In Molecular Signals in the Microbe-Plant Symbiotic and Pathogenic Systems; Lugtenberg, B., Ed.; Springer Verlag: Berlin, 1989; pp 401-407.
19. Boivin, C. Etude génétique chez Rhizobium meliloti du catabolisme des calystégines et de la trigonelline, metabolites secondaires végétaux. (Genetic Study in Rhizobium melioti of Catabolism of the Calystegines and Trigonelline Plant Secondary Metabolites.) Ph.D. Thesis, Université Paul Sabatier, Toulouse, 1991.
20. Molyneux, R. J.; Pan, Y. T.; Goldmann, A.; Tepfer, D. A.; Elbein, A. D. Arch. Biochem. Biophys. 1993, 304, 81-88.
21. Molyneux, R. J.; James, L. F.; Ralphs, M. H.; Pfister, J. A.; Panter, K. E.; Nash, R. J. In Poisonous Plants of the World: Agricultural, Phytochemical and Ecological Aspects; Colegate, S. M., Dorling, P. R., Eds.; CAB International: Wallingford, U.K., 1994; pp 107-112.
22. Elbein, A. D. Semin. Cell Biol. 1991, 2, 309-317.
23. Campbell, R.; Greaves, M. P. In The Rhizosphere; Lynch, J. M., Ed.; John Wiley & Sons: Chichester, 1990; pp 11-34.
24. Barber, D. A.; Martin, J. K. New Phytol. 1976, 76, 69-80.
25. Haller, T.; Stolp, H. Plant Soil 1985, 86, 207-216.
26. Nutman, P. S. In Ecology of Soil-Borne Pathogens; Baker, K. F., Snyder, W. C., Eds.; University of California Press: Berkeley, 1965; pp 231-247.
27. Rovira, A. D. Ann. Rev. Microbiol. 1965, 19, 241-266.
28. Schrot, M. N.; Hildebrand, D. C. Ann. Rev. Phytopathol. 1964, 2, 101-132.
29. Haas, D.; Keel, C.; Laville, J.; Maurhofer, M.; Oberhansli, T.; Schnider, U.; Voisard, C.; Wuthrich, B.; Defago, G. In Advances in Molecular Genetics of Plant-Microbe Interactions; Hennecke, H., Verma, D. P. S., Eds.; Kluwer Academic Publ.: Dordrecht, The Netherlands, 1991; Vol. 1, pp 450-456.
30. Fellows, L. E.; Kite, G. C.; Nash, R. J.; Simmonds, M. S. J.; Scofield, A. M. Phytochemistry 1989, 23, 395-427.
31. Elbein, A. D.; Molyneux, R. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley and Sons: New York, 1987; Vol. 5, Chapter 1, pp 1-54.
32. Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199-210.
33. Stevens, K. L.; Molyneux, R. J. J. Chem. Ecol. 1988, 14, 1467-1473.
34. Putnam, A.; DeFranck, J. Crop Prot. 1983, 2, 173-181.
35. Molyneux, R. J.; Pan, Y. T.; Tropea, J. E.; Benson, M.; Kaushal, G. P.; Elbein, A. D. Biochemistry 1991, 30, 9981-9987.
36. Tan, A.; van der Broek, L.; van Boeckel, S.; Ploegh, H.; Bolscher, J. J. Biol. Chem. 1991, 266, 14504-14510.
37. Al Daher, S.; Fleet, G.; Namgoong, S. K.; Winchester, B. Biochem. J. 1989, 258, 613-615.
38. Asano, N.; Kizu, H.; Oseki, K.; Tomicka, E.; Matsui, K.; Okamoto, M.; Baba, M. J. Med. Chem. 1995, 38, 2349-2356.
39. Rosenberg, C.; Boistard, P.; Dénarié, J.; Casse-Delbard. Mol. Gen. Genet. 1981, 184, 326-333.
40. Kondorosi, E.; Banfalvi, Z.; Kondorosi, A. Mol. Gen. Genet. 1984, 193, 445-452.
41. Rosenberg, C.; Huguet, T. Mol. Gen. Genet. 1984, 196, 533-536.
42. Petit, A.; Tempé, J. Mol. Gen. Genet. 1978, 187, 147-155.
43. Klapwijk, P. M.; Houdshoorn, M.; Schilperoort, R. A. J. Gen. Microbiol. 1977, 102, 1-11.
44. Southern, E. J. Mol. Biol. 1975, 98, 503-517.
45. Tepfer, D. Cell 1984, 37, 959-967.
46. Tepfer, D.; Tempé, J. C. R. Acad. Sci. 1981, 292, 153-156.
47. Murashige, T.; Skoog, F. Physiol. Plant 1962, 15, 473-497.