Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C8H15NO4 |
| Molecular Weight | 189.209 |
| 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](O)[C@@H](O)[C@@H]2O
InChI
InChIKey=JDVVGAQPNNXQDW-TVNFTVLESA-N
InChI=1S/C8H15NO4/c10-4-1-2-9-3-5(11)7(12)8(13)6(4)9/h4-8,10-13H,1-3H2/t4-,5-,6+,7+,8+/m0/s1
| Molecular Formula | C8H15NO4 |
| Molecular Weight | 189.209 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|
| Anti-HIV activity of castanospermine analogues. | 1989 May 27 |
|
| Inhibition of glycoprotein processing and HIV replication by castanospermine analogues. | 1990 |
|
| Castanospermine vs. its 6-O-butanoyl analog: a comparison of toxicity and antiviral activity in vitro and in vivo. | 1991 |
|
| 6-0-butanoylcastanospermine (MDL 28,574) inhibits glycoprotein processing and the growth of HIVs. | 1991 Jun |
|
| 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 |
|
| 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 |
|
| Inhibition of N-linked glycosylation. | 2001 May |
|
| Action of celgosivir (6 O-butanoyl castanospermine) against the pestivirus BVDV: implications for the treatment of hepatitis C. | 2004 May |
|
| Glucose trimming of N-glycan in endoplasmic reticulum is indispensable for the growth of Raphanus sativus seedling (kaiware radish). | 2005 Jul |
|
| A novel approach for N-glycosylation studies using detergent extracted microsomes. | 2005 Oct |
|
| 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 |
|
| Antiviral effects of glycosylation and glucose trimming inhibitors on human parainfluenza virus type 3. | 2006 Oct |
|
| Asymmetric [2 + 2] cycloaddition: total synthesis of (-)-swainsonine and (+)-6-epicastanospermine. | 2006 Oct 12 |
|
| Interference with O-glycosylation in RMA lymphoma cells leads to a reduced in vivo growth of the tumor. | 2006 Sep 15 |
|
| Indolizidine and quinolizidine alkaloids. | 2007 Feb |
|
| Posttranslational N-glycosylation of the hepatitis B virus large envelope protein. | 2007 May 30 |
|
| Synthesis of 1-deoxy-1-hydroxymethyl- and 1-deoxy-1-epi-hydroxymethyl castanospermine as new potential immunomodulating agents. | 2007 Nov 1 |
|
| Vinylogous Mukaiyama aldol reactions with 4-oxy-2-trimethylsilyloxypyrroles: relevance to castanospermine synthesis. | 2007 Nov 3 |
|
| A divergent asymmetric approach to aza-spiropyran derivative and (1S,8aR)-1-hydroxyindolizidine. | 2007 Nov 8 |
|
| Carboazidation of chiral allylsilanes: experimental and theoretical investigations. | 2008 |
|
| Indolizidine and quinolizidine alkaloids. | 2008 Feb |
|
| 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 |
|
| Role of receptor polymorphism and glycosylation in syncytium induction and host range variation of ecotropic mouse gammaretroviruses. | 2008 Jan 10 |
|
| The comparative pathology of the glycosidase inhibitors swainsonine, castanospermine, and calystegines A3, B2, and C1 in mice. | 2008 Jul |
|
| Inhibition of the glucosyltransferase activity of clostridial Rho/Ras-glucosylating toxins by castanospermine. | 2008 Jun 25 |
|
| Synthesis and evaluation of sulfamide-type indolizidines as glycosidase inhibitors. | 2008 May 1 |
|
| Divergence of catalytic mechanism within a glycosidase family provides insight into evolution of carbohydrate metabolism by human gut flora. | 2008 Oct 20 |
|
| Broad-spectrum drugs against viral agents. | 2008 Sep |
|
| Celgosivir, an alpha-glucosidase I inhibitor for the potential treatment of HCV infection. | 2009 Aug |
|
| Disruption of N-linked glycosylation enhances ubiquitin-mediated proteasomal degradation of the human ATP-binding cassette transporter ABCG2. | 2009 Dec |
|
| Promotion of IL-4- and IL-5-dependent differentiation of anti-mu-primed B cells by ascorbic acid 2-glucoside. | 2009 Feb 21 |
|
| Substrate specificity of the oxidoreductase ERp57 is determined primarily by its interaction with calnexin and calreticulin. | 2009 Jan 23 |
|
| Glycosidase inhibition by ring-modified castanospermine analogues: tackling enzyme selectivity by inhibitor tailoring. | 2009 Jul 7 |
|
| Synthesis of thiohydantoin-castanospermine glycomimetics as glycosidase inhibitors. | 2009 May 1 |
|
| Asymmetric synthesis of (+)-castanospermine through enol ether metathesis-hydroboration/oxidation. | 2009 May 21 |
|
| Loss of specific chaperones involved in membrane glycoprotein biosynthesis during the maturation of human erythroid progenitor cells. | 2009 May 22 |
|
| Alternative splicing and transcriptome profiling of experimental autoimmune encephalomyelitis using genome-wide exon arrays. | 2009 Nov 10 |
|
| A concise synthesis of castanospermine by the use of a transannular cyclization. | 2009 Nov 20 |
|
| Inhibition of the exo-beta-D-glucosaminidase CsxA by a glucosamine-configured castanospermine and an amino-australine analogue. | 2009 Oct 21 |
|
| Tetrapisispora phaffii killer toxin is a highly specific beta-glucanase that disrupts the integrity of the yeast cell wall. | 2009 Oct 27 |
|
| Six host range variants of the xenotropic/polytropic gammaretroviruses define determinants for entry in the XPR1 cell surface receptor. | 2009 Oct 7 |
|
| Single chain variable fragment against nicastrin inhibits the gamma-secretase activity. | 2009 Oct 9 |
|
| Alpha-glucosidase promotes hemozoin formation in a blood-sucking bug: an evolutionary history. | 2009 Sep 9 |
|
| N-glycan-dependent quality control of the Na,K-ATPase beta(2) subunit. | 2010 Apr 13 |
|
| N-Glycosylation plays a role in protein folding of human UGT1A9. | 2010 Apr 15 |
|
| Glycosidase inhibition: assessing mimicry of the transition state. | 2010 Jan 21 |
|
| A new synthetic access to bicyclic polyhydroxylated alkaloid analogues from pyranosides. | 2010 Jun 7 |
|
| QSAR Studies on andrographolide derivatives as α-glucosidase inhibitors. | 2010 Mar 2 |
|
| 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.
| Substance Class |
Chemical
Created
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Edited
Fri Dec 15 15:53:19 GMT 2023
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| Record UNII |
Q0I3184XM7
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| Record Status |
Validated (UNII)
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| Record Version |
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CASTANOSPERMINE
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ACTIVE MOIETY |
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