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Journal articles on the topic 'Castanospermine'

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Published: 4 June 2021

Last updated: 25 April 2022

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1

St-Denis, Yves, and Tak Hang Chan. "Synthesis of 8-epi-castanospermine and 6,7,8-tri-epi-castanospermine." Canadian Journal of Chemistry 78, no. 6 (June 1, 2000): 776–83. http://dx.doi.org/10.1139/v00-043.

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8-epi-Castanospermine (11) and 6,7,8-tri-epi-castanospermine (12) were synthesized from the hydroxyproline precursor 13 which was obtained enantioselectively via an enzymatic process.Key words: castanospermine, synthesis of, enzymatic reduction, enzymatic resolution, asymmetric synthesis.

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2

Whitby, Kevin, Theodore C. Pierson, Brian Geiss, Kelly Lane, Michael Engle, Yi Zhou, Robert W. Doms, and Michael S. Diamond. "Castanospermine, a Potent Inhibitor of Dengue Virus Infection In Vitro and In Vivo." Journal of Virology 79, no. 14 (July 2005): 8698–706. http://dx.doi.org/10.1128/jvi.79.14.8698-8706.2005.

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ABSTRACT Previous studies have suggested that α-glucosidase inhibitors such as castanospermine and deoxynojirimycin inhibit dengue virus type 1 infection by disrupting the folding of the structural proteins prM and E, a step crucial to viral secretion. We extend these studies by evaluating the inhibitory activity of castanospermine against a panel of clinically important flaviviruses including all four serotypes of dengue virus, yellow fever virus, and West Nile virus. Using in vitro assays we demonstrated that infections by all serotypes of dengue virus were inhibited by castanospermine. In contrast, yellow fever virus and West Nile virus were partially and almost completely resistant to the effects of the drug, respectively. Castanospermine inhibited dengue virus infection at the level of secretion and infectivity of viral particles. Importantly, castanospermine prevented mortality in a mouse model of dengue virus infection, with doses of 10, 50, and 250 mg/kg of body weight per day being highly effective at promoting survival (P ≤ 0.0001). Correspondingly, castanospermine had no adverse or protective effect on West Nile virus mortality in an analogous mouse model. Overall, our data suggest that castanospermine has a strong antiviral effect on dengue virus infection and warrants further development as a possible treatment in humans.

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3

Palamarczyk, G., and A. D. Elbein. "The effect of castanospermine on the oligosaccharide structures of glycoproteins from lymphoma cell lines." Biochemical Journal 227, no. 3 (May 1, 1985): 795–804. http://dx.doi.org/10.1042/bj2270795.

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The effect of castanospermine on the processing of N-linked oligosaccharides was examined in the parent mouse lymphoma cell line and in a mutant cell line that lacks glucosidase II. When the parent cell line was grown in the presence of castanospermine at 100 micrograms/ml, glucose-containing high-mannose oligosaccharides were obtained that were not found in the absence of inhibitor. These oligosaccharides bound tightly to concanavalin A-Sepharose and were eluted in the same position as oligosaccharides from the mutant cells grown in the absence or presence of the alkaloid. The castanospermine-induced oligosaccharides were characterized by gel filtration on Bio-Gel P-4, by h.p.l.c. analysis, by enzymic digestions and by methylation analysis of [3H]mannose-labelled and [3H]galactose-labelled oligosaccharides. The major oligosaccharide released by endoglucosaminidase H in either parent or mutant cells grown in castanospermine was a Glc3Man7GlcNAc, with smaller amounts of Glc3Man8GlcNAc and Glc3Man9GlcNAc. On the other hand, in the absence of castanospermine the mutant produces mostly Glc2Man7GlcNAc. In addition to the above oligosaccharides, castanospermine stimulated the formation of an endoglucosaminidase H-resistant oligosaccharide in both cell lines. This oligosaccharide was characterized as a Glc2Man5GlcNAc2 (i.e., Glc(1,2)Glc(1,3)Man(1,2)Man(1,2)Man(1,3)[Man(1,6)]Man-GlcNAc-GlcNAc). Castanospermine was tested directly on glucosidase I and glucosidase II in lymphoma cell extracts by using [Glc-3H]Glc3Man9GlcNAc and [Glc-3H]Glc2Man9GlcNAc as substrates. Castanospermine was a potent inhibitor of both activities, but glucosidase I appeared to be more sensitive to inhibition.

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4

Tiwari, Dipak Kumar, Kishor Chandra Bharadwaj, Vedavati G. Puranik, and Dharmendra Kumar Tiwari. "Divergent total synthesis of 1,6,8a-tri-epi-castanospermine and 1-deoxy-6,8a-di-epi-castanospermine from substituted azetidin-2-one (β-lactam), involving a cascade sequence of reactions as a key step." Org. Biomol. Chem. 12, no. 37 (2014): 7389–96. http://dx.doi.org/10.1039/c4ob00948g.

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5

Ratner, N., A. Elbein, M. B. Bunge, S. Porter, R. P. Bunge, and L. Glaser. "Specific asparagine-linked oligosaccharides are not required for certain neuron-neuron and neuron-Schwann cell interactions." Journal of Cell Biology 103, no. 1 (July 1, 1986): 159–70. http://dx.doi.org/10.1083/jcb.103.1.159.

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To determine whether specific asparagine-linked (N-linked) oligosaccharides present in cell surface glycoproteins are required for cell-cell interactions within the peripheral nervous system, we have used castanospermine to inhibit maturation of N-linked sugars in cell cultures of neurons or neurons plus Schwann cells. Maximally 10-15% of the N-linked oligosaccharides on neuronal proteins have normal structure when cells are cultured in the presence of 250 micrograms/ml castanospermine; the remaining oligosaccharides are present as immature carbohydrate chains not normally found in these glycoproteins. Although cultures were treated for 2 wk with castanospermine, cells always remained viable and appeared healthy. We have analyzed several biological responses of embryonic dorsal root ganglion neurons, with or without added purified populations of Schwann cells, in the presence of castanospermine. We have observed that a normal complement of mature, N-linked sugars are not required for neurite outgrowth, neuron-Schwann cell adhesion, neuron-induced Schwann cell proliferation, or ensheathment of neurites by Schwann cells. Treatment of neuronal cultures with castanospermine increases the propensity of neurites to fasciculate. Extracellular matrix deposition by Schwann cells and myelination of neurons by Schwann cells are greatly diminished in the presence of castanospermine as assayed by electron microscopy and immunocytochemistry, suggesting that specific N-linked oligosaccharides are required for the expression of these cellular functions.

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6

Wang, Ai-E., and Pei-Qiang Huang. "Efficient asymmetric syntheses of alkaloids and medicinally relevant molecules based on heterocyclic chiral building blocks." Pure and Applied Chemistry 86, no. 7 (July 22, 2014): 1227–35. http://dx.doi.org/10.1515/pac-2013-1210.

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AbstractIn this report, we present recent progress in synthetic methodologies based on three heterocyclic chiral building blocks developed from our laboratories. The potential of these chiral building block-based methods in the concise asymmetric synthesis of alkaloids and medicinally interesting molecules has been demonstrated by the total syntheses of 8-aza-prostaglandin E1, 11-hydroxylated analogues of the lead compounds CP-734432 and PF-04475270, (+)-castanospermine, (+)-1-epi-castanospermine, 7-deoxy-6-epi-castanospermine as well as 9-epi-sessilifoliamide J.

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7

Stegelmeier, B. L., R. J. Molyneux, A. D. Elbein, and L. F. James. "The Lesions of Locoweed (Astragalus mollissimus), Swainsonine, and Castanospermine in Rats." Veterinary Pathology 32, no. 3 (May 1995): 289–98. http://dx.doi.org/10.1177/030098589503200311.

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To better characterize and compare the toxicity of and lesions produced by locoweed ( Astragalus mollissimus) with those of swainsonine and a related glycoside inhibitor, castanospermine, 55 Sprague-Dawley rats were randomly divided into 11 groups of five animals each. The first eight groups were dosed via subcutaneous osmotic minipumps with swainsonine at 0,0.1,0.7,3.0,7.4, or 14.9 mg/kg/day or with castanospermine at 12.4 or 143.6 mg/kg/day for 28 days. The last three groups were fed alfalfa or locoweed pellets with swainsonine doses of 0, 0.9, or 7.2 mg/kg/day for 28 days. Swainsonine- and locoweed-treated rats gained less weight, ate less, and showed more signs of nervousness than did controls. Histologically, these animals developed vacuolar degeneration of the renal tubular epithelium, the thyroid follicular cells, and the macrophage-phagocytic cells of the lymph nodes, spleen, lung, liver, and thymus. Some rats also developed vacuolation of neurons, ependyma, adrenal cortex, exocrine pancreas, myocardial epicytes, interstitial cells, and gastric parietal cells. No differences in lesion severity or distribution were detected between animals dosed with swainsonine and those dosed with locoweed. Rats dosed with castanospermine were clinically normal; however, they developed mild vacuolation of the renal tubular epithelium, the thyroid follicular epithelium, hepatocytes, and skeletal myocytes. Special stains and lectin histochemical evaluation showed that swainsonine- and castanospermine-induced vacuoles contained mannose-rich oligosaccharides. Castanospermine-induced vacuoles also contained glycogen. These results suggest that 1) swainsonine causes lesions similar to those caused by locoweed and is probably the primary locoweed toxin; 2) castanospermine at high doses causes vacuolar changes in the kidney and thyroid gland; and 3) castanospermine intoxication results in degenerative vacuolation of hepatocytes and skeletal myocytes, similar to genetic glycogenosis.

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8

Machan, Theeraphan, Andrew S. Davis, Boonsom Liawruangrath, and Stephen G. Pyne. "Synthesis of castanospermine." Tetrahedron 64, no. 12 (March 2008): 2725–32. http://dx.doi.org/10.1016/j.tet.2008.01.073.

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9

Brown, RFC, DJ Collins, LM Lagniton, RJ Smith, and NR Wong. "Aromatization Reactions of Castanospermine Tetraacetate." Australian Journal of Chemistry 45, no. 2 (1992): 469. http://dx.doi.org/10.1071/ch9920469.

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The Polonovski reaction of castanospermine tetraacetate N-oxide with acetic anhydride gave (�)-1-acetoxy-8-hydroxy-2,3-dihydro-lH-indolizinium acetate (10) by aromatization of the piperidine ring. N- Bromosuccinimide oxidation of castanospermine tetraacetate gave a low yield (4%) of (+)-2-bromo-5,6,7,8-tetrahydroindolizine-6,7,8-triyl triacetate (13), by aromatization of the pyrrolidine ring.

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10

Liu, Gang, Tian-Jun Wu, Yuan-Ping Ruan, and Pei-Qiang Huang. "A Flexible Approach to Azasugars: Asymmetric Total Syntheses of (+)-Castanospermine, (+)-7-Deoxy-6-epi-castanospermine, and (+)-1-epi-Castanospermine." Chemistry - A European Journal 16, no. 19 (April 8, 2010): 5755–68. http://dx.doi.org/10.1002/chem.200903490.

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11

Winchester, B. G., I. Cenci di Bello, A. C. Richardson, R. J. Nash, L. E. Fellows, N. G. Ramsden, and G. Fleet. "The structural basis of the inhibition of human glycosidases by castanospermine analogues." Biochemical Journal 269, no. 1 (July 1, 1990): 227–31. http://dx.doi.org/10.1042/bj2690227.

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A series of epimers and deoxy derivatives of castanospermine has been synthesized to investigate the contribution of the different chiral centres to the specificity and potency of inhibition of human liver glycosidases. Castanospermine inhibits all forms of alpha- and beta-D-glucosidases, but alteration to any of the five chiral centres in castanospermine markedly decreases the inhibition. 6-Epicastanospermine, which is related to D-pyranomannose in the same way as castanospermine is to D-pyranoglucose, does not inhibit lysosomal (acidic) alpha-mannosidase, but is a good inhibitor of the cytosolic or neutral alpha-mannosidase. Conversely, 1-deoxy-6-epicastanospermine inhibits acidic alpha-mannosidase strongly, but not the neutral alpha-mannosidase. An explanation of this different inhibition based on preferential recognition of different configurations of mannose by the different forms of alpha-mannosidase is postulated. All derivatives of 6-epicastanospermine also have the minimum structural feature for the inhibition of alpha-L-fucosidase, but those with a beta-anomeric substituent do not inhibit the enzyme, or do so very weakly. 1-Deoxy-6,8a-diepicastanospermine, which has four chiral centres identical with alpha-L-fucose, is, however, a potent inhibitor of alpha-L-fucosidase (Ki 1.3 microM).

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12

Liu, Paul S., and Chi-Hsin R. King. "Synthesis of Castanospermine Glucosides." Synthetic Communications 22, no. 14 (July 1992): 2111–16. http://dx.doi.org/10.1080/00397919208021345.

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13

Anderson, Wayne K., and Pingzhong Tan. "Oxidative Degradation of Castanospermine." Synthetic Communications 24, no. 21 (November 1994): 3081–89. http://dx.doi.org/10.1080/00397919408011321.

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14

Nash, Robert J., Linda E. Fellows, Janet V. Dring, Charles H. Stirton, David Carter, Mervyn P. Hegarty, and E. Arthur Bell. "Castanospermine in Alexa species." Phytochemistry 27, no. 5 (January 1988): 1403–4. http://dx.doi.org/10.1016/0031-9422(88)80203-6.

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15

Furneaux, Richard H., Jennifer M. Mason, and Peter C. Tyler. "The chemistry of castanospermine, part II: Synthesis of deoxyfluoro analogues of castanospermine." Tetrahedron Letters 35, no. 19 (May 1994): 3143–46. http://dx.doi.org/10.1016/s0040-4039(00)76852-3.

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16

Hendry, David, Leslie Hough, and Anthony C. Richardson. "Enantiospecific synthesis of polyhydroxylated indolizidines related to castanospermine:1 1-deoxy-castanospermine." Tetrahedron 44, no. 19 (January 1988): 6143–52. http://dx.doi.org/10.1016/s0040-4020(01)89804-5.

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17

Szmidt-Jaworska, Adriana, Jacek Kęsy, and Jan Kopcewicz. "IAA-glucopyranoside stimulation of corn coleoptiles elongation." Acta Societatis Botanicorum Poloniae 66, no. 3-4 (2014): 343–46. http://dx.doi.org/10.5586/asbp.1997.041.

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It has been previously suggested that 1-O-IAGIuc growth stimulation occurs as the effect of its hydrolysis into a free IAA. In present experiments castanospermine, a known β-glucosidase inhibitor, was included. 1-O-IAGluc in the presence of castanospermine stimulated growth of corn coleoptiles segments even stronger then free IAA. So, it seems that 1-O-IAGluc itself, is responsible for the observed stimulation of corn coleoptile segments elongation.

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18

Kadmon, G., A. Kowitz, P. Altevogt, and M. Schachner. "Functional cooperation between the neural adhesion molecules L1 and N-CAM is carbohydrate dependent." Journal of Cell Biology 110, no. 1 (January 1, 1990): 209–18. http://dx.doi.org/10.1083/jcb.110.1.209.

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The neural cell adhesion molecules L1 and N-CAM have been suggested to interact functionally by formation of a complex between the two molecules (Kadmon, G., A. Kowitz, P. Altevogt, and M. Schachner. 1990. J. Cell Biol. 110:193-208). To determine the molecular mechanisms underlying this functional cooperation, we have studied the contribution of carbohydrates to the association of the two molecules at the cell surface. Aggregation or adhesion between L1- and N-CAM-positive neuroblastoma N2A cells was reduced when the synthesis of complex and/or hybrid glycans was modified by castanospermine. Fab fragments of polyclonal antibodies to L1 inhibited aggregation and adhesion of castanospermine-treated cells almost completely, whereas untreated cells were inhibited by approximately 50%. Fab fragments of polyclonal antibodies to N-CAM did not interfere with the interaction between castanospermine-treated cells, whereas they inhibited aggregation or adhesion of untreated cells by approximately 50%. These findings indicate that cell interactions depending both on L1 and N-CAM ("assisted homophilic" binding) can be reduced to an L1-dominated interaction ("homophilic binding"). Treatment of cells with the carbohydrate synthesis inhibitor swainsonine did not modify cell aggregation in the absence or presence of antibodies compared with untreated cells, indicating that castanospermine-sensitive, but swainsonine-insensitive glycans are involved. To investigate whether the appropriate carbohydrate composition is required for an association of L1 and N-CAM in the surface membrane (cis-interaction) or between L1 on one side and L1 and N-CAM on the other side of interacting partner cells (trans-interaction), an L1-positive lymphoid tumor cell line was coaggregated with and adhered to neuroblastoma cells in the various combinations of castanospermine-treated and untreated cells. The results show that it is the cis-interaction between L1 and N-CAM that depends on the appropriate carbohydrate structures.

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19

el Battari, A., P. Forget, F. Fouchier, and P. Pic. "Effect of inhibiting N-glycosylation or oligosaccharide processing on vasoactive intestinal peptide receptor binding activity and structure." Biochemical Journal 278, no. 2 (September 1, 1991): 527–33. http://dx.doi.org/10.1042/bj2780527.

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We used inhibitors of four steps of the glycosylation pathway to examine the contribution of carbohydrate moieties to the ligand-binding activity, cell-surface expression and apparent molecular mass of the human vasoactive intestinal peptide (VIP) receptor. Human melanoma IGR 39 cells, incubated for 60 h with the inhibitors tunicamycin, castanospermine, swainsonine or deoxymannojirimycin, under conditions where cell viability and protein synthesis were not affected, expressed VIP receptor species with different VIP-binding properties. The most pronounced effects on VIP binding were obtained with tunicamycin and deoxymannojirimycin, which respectively caused 80% and 67% inhibition. Treatment with either swainsonine or castanospermine resulted in only a 25-32% decrease in VIP specific binding. Based on Scatchard analyses of data from competition experiments, the decrease in VIP-binding activity in either swainsonine- or deoxymannojirimycin-treated cells was due to a decrease in ligand affinity; the cell-surface number of VIP-binding sites remained unchanged. In contrast, tunicamycin and castanospermine caused decreases in the cell-surface number of functional VIP receptors without affecting affinity. Besides, the drug-treated cells produced VIP-binding proteins with different molecular masses and endoglycosidase H (Endo H) sensitivities. When compared with their counterpart synthesized in control cells, VIP-binding proteins produced by deoxymannojirimycin- or swainsonine-treated cells were smaller in size and exhibited the expected sensitivity to Endo H. No modification in the apparent molecular mass was observed in the presence of either castanospermine or tunicamycin. In addition, after Endo F digestion, all of the deglycosylated proteins migrated with the same electrophoretic mobility. Finally, processing in the presence of castanospermine led to an Endo H-resistant receptor species which showed an unexpected neuraminidase-sensitivity, indicating that, as in control cells, these receptors carry V-linked oligosaccharides with terminal sialic acid residues.

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20

Sasak, V. W., J. M. Ordovas, A. D. Elbein, and R. W. Berninger. "Castanospermine inhibits glucosidase I and glycoprotein secretion in human hepatoma cells." Biochemical Journal 232, no. 3 (December 15, 1985): 759–66. http://dx.doi.org/10.1042/bj2320759.

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We studied the effect of the plant alkaloid castanospermine on the biosynthesis and secretion of human hepatoma glycoproteins. The HepG-2 cells, grown in the presence or absence of the alkaloid, were labelled with [2-3H]mannose and then the labelled glycopeptides were prepared by Pronase digestion. This material was analysed by gel filtration on Bio-Gel P-4 before and after treatment with endo-beta-N-acetylglucosaminidase H. Castanospermine caused an accumulation of high-mannose oligosaccharides, by 70-75% over control. The major accumulated product, which could also be labelled with [3H]galactose and was only partially susceptible to alpha-mannosidase digestion, was identified by h.p.l.c. as a Glc3Man9GlcNAc. Thus the alkaloid inhibits glucosidase I in the human hepatoma cells. Analysis of total glycoproteins secreted by the cells into the medium revealed the presence of only complex oligosaccharides in both control and treated cultures, and the amount of the oligosaccharides labelled with radioactive mannose, galactose or N-acetylmannosamine, secreted by treated cells, was decreased by about 60%. The rate of secretion of total protein labelled with [35S]methionine and precipitated from the medium with trichloroacetic acid was inhibited by up to 40% in the presence of castanospermine. Pulse-chase studies utilizing [35S]methionine labelling were performed to study the effect of the alkaloid on secretion of individual plasma proteins. Immunoprecipitation at different chase times with monospecific antisera showed that castanospermine markedly decreased the secretion rates of alpha 1-antitrypsin, caeruloplasmin and, to a lesser extent, that of antithrombin-III. Secretions of apolipoprotein E, a glycoprotein containing only O-linked oligosaccharide(s), and albumin, a non-glycosylated protein, were not affected by the drug. It is suggested that castanospermine inhibits secretion of at least some glycoproteins containing N-linked oligosaccharides, owing to the inhibition of oligosaccharide processing.

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21

Mulzer, Johann, Henrietta Dehmlow, Juergen Buschmann, and Peter Luger. "Stereocontrolled total synthesis of the unnatural enantiomers of castanospermine and 1-epi-castanospermine." Journal of Organic Chemistry 57, no. 11 (May 1992): 3194–202. http://dx.doi.org/10.1021/jo00037a043.

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22

Taylor, D. L., R. Nash, L. E. Fellows, M. S. Kang, and A. S. Tyms. "Naturally Occurring Pyrrolizidines: Inhibition of α-Glucosidase 1 and Anti-HIV Activity of One Stereoisomer." Antiviral Chemistry and Chemotherapy 3, no. 5 (October 1992): 273–77. http://dx.doi.org/10.1177/095632029200300504.

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Alexine, a naturally occurring pyrrolizidine alkaloid, isolated from Alexa leiopetala, and four stereoisomers, isolated from Castanospermum australe, were investigated for inhibitory activity against the growth of HIV-1. Only treatment with the 7,7a-diepialexine restricted virus growth (IC50 0.38 mm) although it was less active than the indolizidine alkaloid castanospermine (IC50 0.02 mm). The antiviral effects of 7,7a-diepialexine, like castanospermine, correlated with the inhibitory activity against purified pig kidney α-glucosidase 1 of the glycoprotein processing enzymes and the reduced cleavage of the precursor HIV-1 glycoprotein gp160.

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23

Ina, Hiroji, and Chihiro Kibayashi. "A total synthesis of (+)-Castanospermine." Tetrahedron Letters 32, no. 33 (August 1991): 4147–50. http://dx.doi.org/10.1016/s0040-4039(00)79888-1.

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24

Bhide, Rojeev, Reza Mortezaei, A. Scilimati, and Charles J. Sih. "A chemoenzymatic synthesis of (+)-castanospermine." Tetrahedron Letters 31, no. 34 (January 1990): 4827–30. http://dx.doi.org/10.1016/s0040-4039(00)97743-8.

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25

Chemla, F., J. Louvel, C. Botuha, E. Demont, F. Ferreira, and A. Pérez-Luna. "Synthesis of (+)-6-epi-Castanospermine." Synfacts 2010, no. 09 (August 23, 2010): 0974. http://dx.doi.org/10.1055/s-0030-1257933.

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26

Stevens, K. L., and R. J. Molyneux. "Castanospermine?a plant growth regulator." Journal of Chemical Ecology 14, no. 6 (June 1988): 1467–73. http://dx.doi.org/10.1007/bf01012418.

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27

Bartnicka, Ewa, and Aleksander Zamojski. "New syntheses of two epimers of (+)-castanospermine: (+)-8a-Epi- and (+)-1,8a-Di-epi-castanospermine." Tetrahedron 55, no. 7 (February 1999): 2061–76. http://dx.doi.org/10.1016/s0040-4020(98)01218-6.

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28

FURNEAUX, R. H., J. M. MASON, and P. C. TYLER. "ChemInform Abstract: The Chemistry of Castanospermine. Part 2. Synthesis of Deoxyfluoro Analogues of Castanospermine." ChemInform 25, no. 37 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199437232.

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29

Patil, Nitin T., Jayant N. Tilekar, and Dilip D. Dhavale. "A short and efficient synthesis of 1-deoxy-castanospermine and 1-deoxy-8a-epi-castanospermine." Tetrahedron Letters 42, no. 4 (January 2001): 747–49. http://dx.doi.org/10.1016/s0040-4039(00)02103-1.

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30

Yun, Hwayoung, Jongmin Kim, Jaehoon Sim, Sujin Lee, Young Taek Han, Dong-Jo Chang, Dae-Duk Kim, and Young-Ger Suh. "Asymmetric Syntheses of 1-Deoxy-6,8a-di-epi-castanospermine and 1-Deoxy-6-epi-castanospermine." Journal of Organic Chemistry 77, no. 12 (May 25, 2012): 5389–93. http://dx.doi.org/10.1021/jo300309z.

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31

Danielsen, E. M., and G. M. Cowell. "Biosynthesis of intestinal microvillar proteins Processing of N-linked carbohydrate is not required for surface expression." Biochemical Journal 240, no. 3 (December 15, 1986): 777–82. http://dx.doi.org/10.1042/bj2400777.

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Castanospermine, an inhibitor of glucosidase I, the initial enzyme in the trimming of N-linked carbohydrate, was used to study the importance of carbohydrate processing in the biosynthesis of microvillar enzymes in organ-cultured pig intestinal explants. For aminopeptidase N (EC 3.4.11.2), aminopeptidase A (EC 3.4.11.7), sucrase-isomaltase (EC 3.2.1.48-10) and maltase-glucoamylase (EC 3.2.1.20), castanospermine caused the formation of novel transient forms of higher Mr than corresponding controls, indicating a blocked removal of glucose residues. For the first three enzymes, the ‘mature’ (Golgi-processed) forms were similar in size to or slightly smaller than corresponding controls and were, as shown for aminopeptidase N, endoglycosidase-H-sensitive, evidence of a blocked attachment of complex sugars. Maltase-glucoamylase did not undergo conversion into a ‘mature’ form, suggesting that, unlike other microvillar enzymes, it does not receive post-translational O-linked carbohydrate. Castanospermine suppressed the synthesis of the four enzymes, but did not block their transport to the microvillar membrane, showing that processing of N-linked carbohydrate is not required for microvillar expression. The proteinase inhibitor leupeptin partially restored the suppressed synthesis, indicating that the majority of the wrongly processed enzymes, probably because of conformational instability, become degraded soon after synthesis rather than being transported to the microvillar membrane.

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32

Rhinehart, Barry L., Keith M. Robinson, Chi-Hsin R. King, and Paul S. Liu. "Castanospermine-glucosides as selective disaccharidase inhibitors." Biochemical Pharmacology 39, no. 10 (May 1990): 1537–43. http://dx.doi.org/10.1016/0006-2952(90)90518-p.

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33

Margolin, Alexey L., Deborah L. Delinck, and Michael R. Whalon. "Enzyme-catalyzed regioselective acylation of castanospermine." Journal of the American Chemical Society 112, no. 8 (April 1990): 2849–54. http://dx.doi.org/10.1021/ja00164a001.

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34

Landmesser, Nelson G., Hon-Chung Tsui, Chi-Hsin R. King, and Leo A. Paquette. "Regiocontrolled C-8 Acylation of Castanospermine." Synthetic Communications 26, no. 11 (June 1996): 2213–21. http://dx.doi.org/10.1080/00397919608003581.

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35

Sunkara, P. S., D. L. Taylor, M. S. Kang, T. L. Bowlin, P. S. Liu, A. S. Tyms, and A. Sjoerdsma. "ANTI-HIV ACTIVITY OF CASTANOSPERMINE ANALOGUES." Lancet 333, no. 8648 (May 1989): 1206. http://dx.doi.org/10.1016/s0140-6736(89)92787-6.

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36

Anderson, Wayne K., Robert A. Coburn, Ariamala Gopalsamy, and Trevor J. Howe. "A facile selective acylation of castanospermine." Tetrahedron Letters 31, no. 2 (January 1990): 169–70. http://dx.doi.org/10.1016/s0040-4039(00)94361-2.

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37

Kim, No Soo, Jong Ryoo Choi, and Jin Kun Cha. "A concise, enantioselective synthesis of castanospermine." Journal of Organic Chemistry 58, no. 25 (December 1993): 7096–99. http://dx.doi.org/10.1021/jo00077a034.

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38

ANDERSON, W. K., and P. TAN. "ChemInform Abstract: Oxidative Degradation of Castanospermine." ChemInform 26, no. 17 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199517215.

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39

Cheng, Bin, Yi-Xian Li, Yue-Mei Jia, and Chu-Yi Yu. "Concise synthesis of 1- epi -castanospermine." Chinese Chemical Letters 28, no. 8 (August 2017): 1688–92. http://dx.doi.org/10.1016/j.cclet.2017.05.013.

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40

Keenan, Roy W., Y. T. Pan, and Alan D. Elbein. "Preparation and characterization of radioactive castanospermine." Analytical Biochemistry 163, no. 2 (June 1987): 316–21. http://dx.doi.org/10.1016/0003-2697(87)90230-2.

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41

Schols, D., R. Pauwels, M. Witvrouw, J. Desmyter, and E. De Clercq. "Differential Activity of Polyanionic Compounds and Castanospermine against HIV Replication and HIV-Induced Syncytium Formation Depending on Virus Strain and Cell Type." Antiviral Chemistry and Chemotherapy 3, no. 1 (February 1992): 23–29. http://dx.doi.org/10.1177/095632029200300104.

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Abstract:

Polyanionic compounds [i.e. pentosan polysulphate, dextran sulphate, heparin, suramin, and aurintricarboxylic acid (ATA)] and castanospermine were examined for their inhibitory effect on human immunodeficiency virus (HIV) strains (HIV-1IIIB, HIV-1RF, HIV-2ROD and HIV-2EHO) in two different assays (HIV cytopathicity in MT-4 cells and HIV antigen expression in CEM cells). In the MT-4 assay dextran sulphate and pentosan polysulphate were more active against HIV-2ROD, suramin was more active against HIV-1RF, and ATA more active against HIV-2EHO-Heparin was less, but castanospermine was more, active against the two HIV-2 strains. In the CEM assay dextran sulphate and suramin were equally active against all HIV strains, pentosan polysulphate was more active against both HIV-2 strains, whereas heparin was less active against HIV-2ROD and ATA again was more active against HIV-2EHO. The compounds and soluble CD4 (sCD4) were also tested in the HIV-induced syncytium formation assay, where chronically infected HUT-78 cells were mixed with uninfected MOLT-4 or CEM cells. The inhibitory effect of suramin and ATA on syncytium formation was independent of the virus strain or cell type. For dextran sulphate and pentosan polysulphate, it was dependent on virus strain, and for heparin, castanospermine, and sCD4, it was dependent on both the virus strain and cell type.

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42

Ayalon-Soffer, M., M. Shenkman, and G. Z. Lederkremer. "Differential role of mannose and glucose trimming in the ER degradation of asialoglycoprotein receptor subunits." Journal of Cell Science 112, no. 19 (October 1, 1999): 3309–18. http://dx.doi.org/10.1242/jcs.112.19.3309.

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Abstract:

To gain insight into how sugar chain processing events modulate endoplasmic reticulum (ER)/proteasomal degradation we looked at human asialoglycoprotein receptor polypeptides H2a and H2b, variants which differ only by an extra pentapeptide (EGHRG) present in H2a. Membrane-bound H2a is a precursor of a soluble secreted form while H2b reaches the plasma membrane. Uncleaved precursor H2a molecules are completely retained in the ER and degraded as well as a portion of H2b. Inhibition of N-linked sugar chain mannose trimming stabilized both variants. In contrast, inhibition of glucose trimming with castanospermine greatly enhanced the degradation rate of H2a but not that of H2b. We studied a possible involvement of the ER chaperone calnexin, as inhibitors of glucose trimming are known to prevent calnexin binding. Incubation of cells with low concentrations of castanospermine (30 microg/ml) did not interfere with calnexin binding to H2a while causing the same accelerated degradation as high concentrations (>100 microg/ml) which did inhibit the association. Castanospermine treatment after calnexin binding blocked the dissociation of the chaperone but still caused accelerated degradation. The increased degradation could be blocked by a specific proteasome inhibitor, ZL(3)VS. Our results suggest that extensive mannose trimming or retention of glucose residues due to lack of glucose trimming are signals for ER/proteasomal degradation independent of interaction with calnexin.

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43

Furneaux, Richard H., Jennifer M. Mason, and Peter C. Tyler. "The chemistry of castanospermine, part III:1,2 Castanospermine-6-phosphate, an unusual route to a novel compound." Tetrahedron Letters 36, no. 17 (April 1995): 3055–58. http://dx.doi.org/10.1016/0040-4039(95)00425-c.

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44

VERHOEVEN, Adrie J. M., Bernadette P. NEVE, and Hans JANSEN. "Secretion and apparent activation of human hepatic lipase requires proper oligosaccharide processing in the endoplasmic reticulum." Biochemical Journal 337, no. 1 (December 17, 1998): 133–40. http://dx.doi.org/10.1042/bj3370133.

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Human hepatic lipase (HL) is a glycoprotein with four N-linked oligosaccharide side chains. The importance of glycosylation for the secretion of catalytically active HL was studied in HepG2 cells by using inhibitors of intracellular trafficking, N-glycosylation and oligosaccharide processing. Secretion of HL was inhibited by carbonyl cyanide m-chlorophenylhydrazone (CCCP), monensin, brefeldin A (BFA), tunicamycin, castanospermine and N-methyldeoxynojirimycin, but not by 1-deoxymannojirimycin. Secretion of α1-antitrypsin, an unrelated N-glycoprotein, was also inhibited by monensin, BFA and tunicamycin, but not by CCCP, castanospermine or N-methyldeoxynojirimycin. Intracellular HL activity decreased with CCCP, tunicamycin, castanospermine and N-methyldeoxynojirimycin, but increased with monensin and BFA. In the absence of protein synthesis de novo, HL activity secreted into the medium was 7.8±2.1-fold higher (mean±S.D., n = 7) than the simultaneous fall in intracellular HL activity. In cells pretreated with monensin or BFA, this factor decreased to 1.3±0.5, indicating that the apparent increase in HL activity had already occurred within these cells. After chromatography on Sepharose–heparin, the specific triacylglycerol hydrolase activity of secreted HL was only 1.7±0.3-fold higher than that of intracellular HL, indicating that the secretion-coupled increase in HL activity is only partly explained by true activation. We conclude that oligosaccharide processing by glucosidases in the endoplasmic reticulum is necessary for the transport of newly synthesized human HL, but not α1-antitrypsin, to the Golgi, where the catalytic activity of HL is unmasked.

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45

Wu, Tian-Jun, and Pei-Qiang Huang. "A concise approach to (+)-1-epi-castanospermine." Tetrahedron Letters 49, no. 2 (January 2008): 383–86. http://dx.doi.org/10.1016/j.tetlet.2007.11.033.

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46

Reymond, Jean-Louis, and Pierre Vogel. "A highly stereoselective total synthesis of (±)castanospermine." Tetrahedron Letters 30, no. 6 (1989): 705–6. http://dx.doi.org/10.1016/s0040-4039(01)80287-2.

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47

Anzeveno, Peter B., Paul T. Angell, Laura J. Creemer, and Michael R. Whalon. "An efficient, highly stereoselective synthesis of (+)-castanospermine." Tetrahedron Letters 31, no. 30 (January 1990): 4321–24. http://dx.doi.org/10.1016/s0040-4039(00)97611-1.

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48

Cronin, Linda, and Paul V. Murphy. "Novel Synthesis of Castanospermine and 1-Epicastanospermine." Organic Letters 7, no. 13 (June 2005): 2691–93. http://dx.doi.org/10.1021/ol0508577.

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49

Somfai, Peter, Patrice Marchand, Staffan Torsell, and Ulf M. Lindström. "Asymmetric synthesis of (+)-1-deoxynojirimycin and (+)-castanospermine." Tetrahedron 59, no. 8 (February 2003): 1293–99. http://dx.doi.org/10.1016/s0040-4020(02)01660-5.

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50

Setoi, Hiroyuki, Hidekazu Takeno, and Masashi Hashimoto. "Total synthesis of (+)-castanospermine from D-mannose." Tetrahedron Letters 26, no. 38 (January 1985): 4617–20. http://dx.doi.org/10.1016/s0040-4039(00)98767-7.

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