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C3784

Castanospermine

Name: Castanospermine
Brand: SIGMA

≥94% (GC), BioUltra, from Castanospermum australe seeds

Synonym(s):

(1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyoctahydroindolizidine, (1S,6S,7R,8R,8aR)-Octahydro-1,6,7,8-indolizinetetrol

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About This Item

Empirical Formula (Hill Notation):

C₈H₁₅NO₄

CAS Number:

79831-76-8

Molecular Weight:

189.21

Beilstein:

3588654

MDL number:

MFCD00017555

UNSPSC Code:

12352200

PubChem Substance ID:

24892642

biological source

Castanospermum australe seeds

product line

BioUltra

Assay

≥94% (GC)

form

powder

mp

212-215 °C (dec.)

solubility

1 M HCl: 20 mg/mL, clear, colorless to faintly yellow

storage temp.

2-8°C

SMILES string

O[C@H]1CCN2C[C@H](O)[C@@H](O)[C@H](O)[C@@H]12

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

InChI key

JDVVGAQPNNXQDW-TVNFTVLESA-N

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Biochem/physiol Actions

α-glucosidase Inhibitor

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Effects of the anti-inflammatory compounds castanospermine, mannose-6-phosphate and fucoidan on allograft rejection and elicited peritoneal exudates.

M R Bartlett et al.

Immunology and cell biology, 72(5), 367-374 (1994-10-01)

The glycoprotein processing inhibitor castanospermine (CS) and the monosaccharide mannose-6-phosphate (M6P), as well as some sulfated polysaccharides (SPS), have been shown to inhibit inflammation in rat models of experimental autoimmune encephalomyelitis and adjuvant-induced arthritis. Here, the anti-inflammatory effects of these

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.

K S Ajish Kumar et al.

Organic & biomolecular chemistry, 6(4), 703-711 (2008-02-12)

The utility of a D-glucose-derived aziridine carboxylate was demonstrated for the synthesis of polyhydroxylated quinolizidine and indolizidine alkaloids. The chemoselective reduction of 1 followed by two-carbon homologation by the Wittig reaction afforded gamma,delta-aziridino-alpha,beta-unsaturated ester 9, which on regioselective nucleophilic aziridine

Asymmetric [2 + 2] cycloaddition: total synthesis of (-)-swainsonine and (+)-6-epicastanospermine.

Julien Ceccon et al.

Organic letters, 8(21), 4739-4742 (2006-10-06)

[reaction: see text] An asymmetric total synthesis of (-)-swainsonine and (+)-6-epicastanospermine is described from a common intermediate, which is obtained through diastereoselective [2 + 2] cycloaddition of dichloroketene to a chiral enol ether.

Dose- and schedule-dependent protective efficacy of celgosivir in a lethal mouse model for dengue virus infection informs dosing regimen for a proof of concept clinical trial.

Satoru Watanabe et al.

Antiviral research, 96(1), 32-35 (2012-08-08)

Celgosivir (6-O-butanoyl castanospermine), a pro-drug of the naturally occurring castanospermine, is an inhibitor of α-glucosidase I and II that is found to be a potent inhibitor of several enveloped viruses including all four serotypes of dengue virus. We showed previously

Synthesis of 1-deoxy-1-hydroxymethyl- and 1-deoxy-1-epi-hydroxymethyl castanospermine as new potential immunomodulating agents.

Vinod P Vyavahare et al.

Journal of medicinal chemistry, 50(22), 5519-5523 (2007-10-09)

Two new C-1 epimeric hydroxymethyl castanospermine congeners 2a and 2b, synthesized by stereocontrolled intramolecular double reductive amination of D-glucose derived beta-keto ester as a key step, showed impressive immuno-potentiating property. The bioactivity was mediated through up-regulation of T(H1)/T(H2) cytokine ratio.

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