Chapter Five Polyhydroxylated alkaloids that inhibit glycosidases

作者: Robert J Nash , Alison A. Watson , Naoki Asano

DOI: 10.1016/S0735-8210(96)80009-4

关键词: GlycosidePyranoseNojirimycinBicyclic moleculeOrganic chemistryPyrrolidinePyrrolizidineAlkaloidChemistryStereochemistryIndolizidine

摘要: Publisher Summary This chapter discusses the polyhydroxylated alkaloids that inhibit glycosidases. A remarkable range of monocyclic and bicyclic are specific potent glycosidase inhibitors have been isolated from plants, microbial filtrates, insects, though latter probably sequestered them their food-plants. They include derivatives pyrrolidine, piperidme, pyrrolizidine, octahydroindolizine (indolizidine) Atortropane ring systems. An increasing number being found which also occur as glycosides. These very widespread but long remained undetected because they do not react with reagents commonly used for alkaloid detection such Dragendorff's iodoplatinate readily dissolve in solvents chloroform. can be considered analogues monosaccharides oxygen has replaced by nitrogen. glycosidases mimicking pyranosyl furanosyl moiety natural substrates, e.g., nojirimycin corresponds to glucose pyranose configuration is an inhibitor α-and β-glucosidases various sources.

参考文章(124)
M T H Axamawaty, G W J Fleet, K A Hannah, S K Namgoong, M L Sinnott, Inhibition of the α-L-arabinofuranosidase III of Monilinia fructigena by 1,4-dideoxy-1,4-imino-L-threitol and 1,4-dideoxy-1,4-imino-L-arabinitol Biochemical Journal. ,vol. 266, pp. 245- 249 ,(1990) , 10.1042/BJ2660245
Umezawa K, Aoyagi T, Ochi Y, Atsumi S, Inhibition of tumor cell invasion in the Boyden chamber assay by a mannosidase inhibitor, mannostatin A. Anticancer Research. ,vol. 13, pp. 1421- 1424 ,(1993)
D R Tulsiani, T M Harris, O Touster, Swainsonine inhibits the biosynthesis of complex glycoproteins by inhibition of Golgi mannosidase II. Journal of Biological Chemistry. ,vol. 257, pp. 7936- 7939 ,(1982) , 10.1016/S0021-9258(18)34274-1
Naoki Asano, Atsushi Kato, Kengo Oseki, Haruhisa Kizu, Katsuhiko Matsui, Calystegins of Physalis alkekengi var. francheti (Solanaceae). Structure determination and their glycosidase inhibitory activities. FEBS Journal. ,vol. 229, pp. 369- 376 ,(1995) , 10.1111/J.1432-1033.1995.0369K.X
G P Kaushal, Y T Pan, J E Tropea, M Mitchell, P Liu, A D Elbein, Selective inhibition of glycoprotein-processing enzymes. Differential inhibition of glucosidases I and II in cell culture. Journal of Biological Chemistry. ,vol. 263, pp. 17278- 17283 ,(1988) , 10.1016/S0021-9258(19)77832-6
J.E. Tropea, G.P. Kaushal, A.D. Elbein, M. Mitchell, Kifunensine, a potent inhibitor of the glycoprotein processing mannosidase I. Journal of Biological Chemistry. ,vol. 265, pp. 15599- 15605 ,(1990) , 10.1016/S0021-9258(18)55439-9
Jose Baptiste, Paul E. Goss, Michael Baker, James W. Dennis, Berny Fernandes, A Phase I Study of Swainsonine in Patients with Advanced Malignancies Cancer Research. ,vol. 54, pp. 1450- 1457 ,(1994)
YOHJI EZURE, NOBUTOSHI OJIMA, KIYOTAKA KONNO, KATSUNORI MIYAZAKI, NAOYOSHI YAMADA, MAKOTO SUGIYAMA, MANABU ITOH, TERUYA NAKAMURA, Isolation of 1,5-dideoxy-1,5-imino-D-mannitol from culture broth of Streptomyces species. The Journal of Antibiotics. ,vol. 41, pp. 1142- 1144 ,(1988) , 10.7164/ANTIBIOTICS.41.1142