Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C12H21NO5 |
| Molecular Weight | 259.2988 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12[C@@H](O)CCN1C[C@H](OC(=O)CCC)[C@@H](O)[C@@H]2O
InChI
InChIKey=HTJGLYIJVSDQAE-VWNXEWBOSA-N
InChI=1S/C12H21NO5/c1-2-3-9(15)18-8-6-13-5-4-7(14)10(13)12(17)11(8)16/h7-8,10-12,14,16-17H,2-6H2,1H3/t7-,8-,10+,11+,12+/m0/s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/27509020 | https://www.ncbi.nlm.nih.gov/pubmed/19649930 | https://www.ncbi.nlm.nih.gov/pubmed/26794905https://www.ncbi.nlm.nih.gov/pubmed/3881759Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27986123 | https://www.ncbi.nlm.nih.gov/pubmed/15994763 | https://www.ncbi.nlm.nih.gov/pubmed/3300654
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27509020 | https://www.ncbi.nlm.nih.gov/pubmed/19649930 | https://www.ncbi.nlm.nih.gov/pubmed/26794905https://www.ncbi.nlm.nih.gov/pubmed/3881759
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27986123 | https://www.ncbi.nlm.nih.gov/pubmed/15994763 | https://www.ncbi.nlm.nih.gov/pubmed/3300654
Castanospermine (1,6,7,8-tetrahydroxyoctahydroindolizine) is an indolizine alkaloid first isolated from the seeds of Australian tree Castanospermum austral. Castanospermine is a potent inhibitor of some glucosidase enzymes and has antiviral, immunosuppressant and anti-inflammatory activity in vitro and in animal models. Castanospermine has been shown to be a potent inhibitor of almond emulsion β-glucosidase, and also to inhibit fungal β-xylosidase. Additionally, castanospermine may have the potential ability to inhibit syncytium formation between HIV-infected and CD4-expressing cells and may also interfere with infectivity. It has also been demonstrated that this agent inhibits inflammation at the level of leukocyte extravasation in rat models of experimental adjuvant-induced arthritis and autoimmune encephalomyelitis. Celgosivir, Castanospermine’s oral prodrug, is currently tested in clinical trials.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Castanospermine vs. its 6-O-butanoyl analog: a comparison of toxicity and antiviral activity in vitro and in vivo. | 1991 |
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| 6-0-butanoylcastanospermine (MDL 28,574) inhibits glycoprotein processing and the growth of HIVs. | 1991 Jun |
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| Inhibition of AIDS virus replication by acemannan in vitro. | 1991 Sep |
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| Inhibition of alpha-glucosidase I of the glycoprotein-processing enzymes by 6-O-butanoyl castanospermine (MDL 28,574) and its consequences in human immunodeficiency virus-infected T cells. | 1994 Aug |
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| The prevention of cell adhesion and the cell-to-cell spread of HIV-1 in vitro by the alpha-glucosidase 1 inhibitor, 6-O-butanoyl castanospermine (MDL 28574). | 1994 Oct |
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| Inhibition of N-linked glycosylation. | 2001 May |
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| Bioavailability of a series of novel acylated ascorbic acid derivatives, 6-O-acyl-2-O-alpha-D-glucopyranosyl-L-ascorbic acids, as an ascorbic acid supplement in rats and guinea pigs. | 2002 Aug |
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| Involvement of [beta]-glucans in the wide-spectrum antimicrobial activity of Williopsis saturnus var. mrakii MUCL 41968 killer toxin. | 2002 Nov |
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| Glycosylation processing inhibition by castanospermine prevents experimental autoimmune encephalomyelitis by interference with IL-2 receptor signal transduction. | 2002 Nov |
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| Isomaltose formed by alpha-glucosidases triggers amylase induction in Aspergillus nidulans. | 2002 Oct |
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| Association of the thyrotropin receptor with calnexin, calreticulin and BiP. Efects on the maturation of the receptor. | 2002 Oct |
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| Purification and biochemical characterization of a soluble alpha-glucosidase from the parasite Entamoeba histolytica. | 2003 |
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| Calreticulin promotes folding/dimerization of human lipoprotein lipase expressed in insect cells (sf21). | 2003 Aug 1 |
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| Expression and role of mannose receptor/terminal high-mannose type oligosaccharide on osteoclast precursors during osteoclast formation. | 2003 Feb |
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| Role of oligomannosidic N-glycans in the proliferation, adhesion and signalling of C6 glioblastoma cells. | 2003 Jan-Feb |
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| A deficiency in dolichyl-P-glucose:Glc1Man9GlcNAc2-PP-dolichyl alpha3-glucosyltransferase defines a new subtype of congenital disorders of glycosylation. | 2003 Mar 14 |
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| N-linked oligosaccharide processing, but not association with calnexin/calreticulin is highly correlated with endoplasmic reticulum-associated degradation of antithrombin Glu313-deleted mutant. | 2003 Mar 15 |
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| The cargo receptor ERGIC-53 is a target of the unfolded protein response. | 2003 May 16 |
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| Maturation of hepatic lipase. Formation of functional enzyme in the endoplasmic reticulum is the rate-limiting step in its secretion. | 2004 Feb 13 |
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| Action of celgosivir (6 O-butanoyl castanospermine) against the pestivirus BVDV: implications for the treatment of hepatitis C. | 2004 May |
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| Combined donor leucocyte administration and immunosuppressive drug treatment for survival of rat heart allografts. | 2004 Nov |
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| Conversion of the carbohydrate structures of glycoproteins in roots of Raphanus sativus using several glycosidase inhibitors. | 2004 Oct |
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| Indolizidine and quinolizidine alkaloids. | 2004 Oct |
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| Glucose trimming of N-glycan in endoplasmic reticulum is indispensable for the growth of Raphanus sativus seedling (kaiware radish). | 2005 Jul |
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| Novel synthesis of castanospermine and 1-epicastanospermine. | 2005 Jun 23 |
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| A novel approach for N-glycosylation studies using detergent extracted microsomes. | 2005 Oct |
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| Characterization of endoplasmic reticulum-associated degradation of a protein S mutant identified in a family of quantitative protein S deficiency. | 2006 |
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| Intramolecular 5-endo-trig aminomercuration of beta-hydroxy-gamma-alkenylamines: efficient route to a pyrrolidine ring and its application for the synthesis of (+)-castanospermine and analogues. | 2006 Jun 9 |
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| Asymmetric [2 + 2] cycloaddition: total synthesis of (-)-swainsonine and (+)-6-epicastanospermine. | 2006 Oct 12 |
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| Indolizidine and quinolizidine alkaloids. | 2007 Feb |
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| Posttranslational N-glycosylation of the hepatitis B virus large envelope protein. | 2007 May 30 |
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| Synthesis of 1-deoxy-1-hydroxymethyl- and 1-deoxy-1-epi-hydroxymethyl castanospermine as new potential immunomodulating agents. | 2007 Nov 1 |
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| Vinylogous Mukaiyama aldol reactions with 4-oxy-2-trimethylsilyloxypyrroles: relevance to castanospermine synthesis. | 2007 Nov 3 |
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| Indolizidine and quinolizidine alkaloids. | 2008 Feb |
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| Efficient synthesis of (+)-1,8,8a-tri-epi-swainsonine, (+)-1,2-di-epi-lentiginosine, (+)-9a-epi-homocastanospermine and (-)-9-deoxy-9a-epi-homocastanospermine from a D-glucose-derived aziridine carboxylate, and study of their glycosidase inhibitory activities. | 2008 Feb 21 |
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| Role of receptor polymorphism and glycosylation in syncytium induction and host range variation of ecotropic mouse gammaretroviruses. | 2008 Jan 10 |
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| Synthesis and evaluation of sulfamide-type indolizidines as glycosidase inhibitors. | 2008 May 1 |
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| Divergence of catalytic mechanism within a glycosidase family provides insight into evolution of carbohydrate metabolism by human gut flora. | 2008 Oct 20 |
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| Broad-spectrum drugs against viral agents. | 2008 Sep |
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| Celgosivir, an alpha-glucosidase I inhibitor for the potential treatment of HCV infection. | 2009 Aug |
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| Disruption of N-linked glycosylation enhances ubiquitin-mediated proteasomal degradation of the human ATP-binding cassette transporter ABCG2. | 2009 Dec |
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| Promotion of IL-4- and IL-5-dependent differentiation of anti-mu-primed B cells by ascorbic acid 2-glucoside. | 2009 Feb 21 |
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| Substrate specificity of the oxidoreductase ERp57 is determined primarily by its interaction with calnexin and calreticulin. | 2009 Jan 23 |
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| Glycosidase inhibition by ring-modified castanospermine analogues: tackling enzyme selectivity by inhibitor tailoring. | 2009 Jul 7 |
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| Loss of specific chaperones involved in membrane glycoprotein biosynthesis during the maturation of human erythroid progenitor cells. | 2009 May 22 |
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| Alternative splicing and transcriptome profiling of experimental autoimmune encephalomyelitis using genome-wide exon arrays. | 2009 Nov 10 |
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| Inhibition of the exo-beta-D-glucosaminidase CsxA by a glucosamine-configured castanospermine and an amino-australine analogue. | 2009 Oct 21 |
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| Tetrapisispora phaffii killer toxin is a highly specific beta-glucanase that disrupts the integrity of the yeast cell wall. | 2009 Oct 27 |
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| Alpha-glucosidase promotes hemozoin formation in a blood-sucking bug: an evolutionary history. | 2009 Sep 9 |
|
| A flexible approach to azasugars: asymmetric total syntheses of (+)-castanospermine, (+)-7-deoxy-6-epi-castanospermine, and (+)-1-epi-castanospermine. | 2010 May 17 |
Patents
Sample Use Guides
LoVo/Dx, W1PR, W1TR and A2780T1 cell lines were used for activity evaluation. The cells were seeded at 4x10^3 cells/well (200 μl) in 96-well culture plates and pre-incubated for 48 h. To examine the effect of BFA, CAS or chemotherapeutic drugs on cell survival, the cells were treated with increasing concentrations of BFA, CAS (Castanospermine, 10 μg/ml for LoVo/Dx, 50 μg/ml for W1PR and W1TR and 60 μg/ml for A2780T1 cells.) for 72 h. Subsequently, 10 μl of MTT labeling reagent was added to the medium (the final concentration of MTT was 0.5 mg/ml) for 4 h and 100 μl of the solubilized solution was then added to each well. After an overnight incubation, the absorbance was measured in a microplate reader at 570 nm with a reference wavelength of 720 nm.
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NCI_THESAURUS |
C281
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NCI_THESAURUS |
C2846
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C070715
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100000082063
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Celgosivir
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121104-96-9
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DTXSID70153153
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CHEMBL2110737
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DB06580
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SUB07435MIG
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C79567
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60734
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895VG117HN
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7608
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SUBSTANCE RECORD
