CASTANOSPERMINE Chemical Properties

Melting point:

213-217 °C (lit.)

alpha 

D25 +79.7° (c = 0.93 in water)

Boiling point:

421.9±45.0 °C(Predicted)

Density 

1.53±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

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

form 

White solid

pka

6.09(at 25℃)

color 

White or off-white

optical activity

[α]20/D +80°, c = 0.9 in H2O

Water Solubility 

Soluble in water

Merck 

13,1906

BRN 

3588654

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in distilled water may be stored at -20°C for up to 3 months.

CAS DataBase Reference

79831-76-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

10-21

HS Code 

2921290090

MSDS

• Language:English Provider:SigmaAldrich

CASTANOSPERMINE Usage And Synthesis

Description

Glucosidases catalyze the cleavage of individual glucosyl residues from various glycoconjugates, including complex carbohydrates and glycoproteins. Castanospermine is an inhibitor of both α- and β-glucosidases, inhibiting lysosomal and neutral α-glucosidases with K_i values of 0.1 and 10 μM, respectively, and lysosomal and cytosolic β-glucosidases with K_i values of 7 and 40 μM, respectively. It is effective both in vitro and in vivo. Through its effects on glucosidases, castanospermine blocks N-linked glycosylation during post-translational modification of proteins, affecting protein trafficking and cell functions that are dependent on glycosylation, including angiogenesis. Castanospermine also interferes with viral replication and infection that is dependent on glucosidase activity.

Chemical Properties

White Crystalline Solid

Occurrence

The seeds of Castanospermum australe yield this simple alkaloid. It forms colourless crystals from EtOH and is dextrorotatory with a specific rotation of [α]D25 +79.7° (c 0.93, H20). Castano spermine has been characterized as the crystalline methiodide, m.p. 11O-112°C.

Uses

Castanospermine is a plant alkaloid shown to be a potent inhibitor of lysosomal a-or beta- glucosidase. It also inhibits mammalian glucosidase 1 and beta-mannosidase from sweet almonds and fungal beta-xylosidase.

Uses

a-L-fucosidases inhibitor

Uses

Castanospermine, is used as a glycosidase inhibitor and antiinflammatory agent.castanospermine is used 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. Castanospermine is an inhibitor of Glucosidase I, Maltase-glucoamylase, and MANBA. Potent inhibitor of α- and β-glucosidases, especially glucosidase l (required for glucoprotein processing by transfer of mannose and glucose from asparagine-linked lipids). Inhibits HIV syncytium formation and replication.

Definition

ChEBI: Castanospermine is a tetrahydroxyindolizidine alkaloid that consists of octahydroindolizine having four hydroxy substituents located at positions 1, 6, 7 and 8 (the 1S,6S,7R,8R,8aR-diastereomer). It has a role as a metabolite, an anti-HIV-1 agent, an anti-inflammatory agent and an EC 3.2.1.* (glycosidase) inhibitor.

Biological Activity

Potent inhibitor of α - and β -glucosidases, especially glucosidase l (required for glucoprotein processing by transfer of mannose and glucose from asparagine-linked lipids). Inhibits HIV syncytium formation and replication.

storage

Store at RT

References

[1] RICK SAUL  A. D E  R J Molyneux. Studies on the mechanism of castanospermine inhibition of α- and β-glucosidases[J]. Archives of biochemistry and biophysics, 1984, 230 2: Pages 668-675. DOI:10.1016/0003-9861(84)90448-x
[2] REINALD REPPS. The effects of processing inhibitors of N-linked oligosaccharides on the intracellular migration of glycoprotein E2 of mouse hepatitis virus and the maturation of coronavirus particles.[J]. The Journal of Biological Chemistry, 1985, 61 1: 15873-15879. DOI:10.1016/s0021-9258(17)36339-1
[3] ROB A. GRUTERS. Interference with HIV-induced syncytium formation and viral infectivity by inhibitors of trimming glucosidase[J]. Nature, 1987, 330 6143: 74-77. DOI:10.1038/330074a0
[4] J L FRANC  J L  A Giraud. Effects of deoxymannojirimycin and castanospermine on the polarized secretion of thyroglobulin.[J]. Endocrinology, 1990, 126 3: 1464-1470. DOI:10.1210/endo-126-3-1464
[5] R PILI. The alpha-glucosidase I inhibitor castanospermine alters endothelial cell glycosylation, prevents angiogenesis, and inhibits tumor growth.[J]. Cancer research, 1995, 55 13: 2920-2926.
[6] B.L. RHINEHART . Castanospermine blocks the hyperglycemic response to carbohydrates in vivo: A result of intestinal disaccharidase inhibition[J]. Life sciences, 1987, 41 20: Pages 2325-2331. DOI:10.1016/0024-3205(87)90546-7

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