Castanospermine

• CAT Number: I004913
• CAS Number: 79831-76-8
• Molecular Formula: C₈H₁₅NO₄
• Molecular Weight: 189.21
• Purity: ≥95%
• Synonyms: (1S,6S,7R,8R,8aR)-octahydroindolizine-1,6,7,8-tetraol
• Target: Glycosylases
• Solubility: Soluble to 50 mM in DMSO and to 100 mM in water
• Storage: Store at RT
• InChI: 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
• InChIKey: JDVVGAQPNNXQDW-TVNFTVLESA-N
• SMILES: C1CN2CC(C(C(C2C1O)O)O)O

Castanospermine (CAT: I004913) is a natural alkaloid derived from the seeds of the Castanospermum australe tree. It is known for its inhibitory activity against glycosidases, enzymes involved in carbohydrate metabolism. Castanospermine acts by binding to the active site of glycosidases, preventing the hydrolysis of glycosidic bonds. This inhibition can have various biological effects, including the modulation of protein glycosylation and the disruption of viral replication. Castanospermine has been studied for its potential antiviral, anticancer, and antiparasitic properties. It serves as a valuable tool in glycobiology research and drug development targeting glycosidase-related pathways.

Reference

[1]. Bryan G, Anthony C et al. The structural basis of the inhibition of human glycosidases by
castanospermine analogues. Biochem. J. (1990) 269, 227-231.

[2]. Eisaku Tsujii et al. Nectrisine Is a Potent Inhibitor of a-Glucosidases, Demonstrating
Activities Similarly at Enzyme and Cellular Levels. Biochemical and Biophysical Research Communications 220, 459-466 (1996)

[3]. Pili R et al. The alpha-glucosidase I inhibitor castanospermine alters endothelial cell glycosylation, preventsangiogenesis, and inhibits tumor growth. Cancer Res. 1995 Jul 1;55(13):2920-6.