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HomeProduct name listCASTANOSPERMINE

CASTANOSPERMINE

Synonym(s):Castanospermine;(1S,6S,7R,8R,8aR)-Octahydro-1,6,7,8-indolizinetetrol;(1S,6S,7R,8aR)-Tetrahydroxyoctahydroindolizine;1,6,7,8-Tetrahydroxyoctahydroindolizine;(1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyoctahydroindolizidine

CASTANOSPERMINE Structural

What is CASTANOSPERMINE?

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 Ki values of 0.1 and 10 μM, respectively, and lysosomal and cytosolic β-glucosidases with Ki 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.

The Uses of CASTANOSPERMINE

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.

The Uses of CASTANOSPERMINE

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.

The Uses of CASTANOSPERMINE

a-L-fucosidases inhibitor

What are the applications of Application

Castanospermine is a glycosidase inhibitor and antiinflammatory agent

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) Saul et al. (1984), Studies on the mechanism of castanospermine inhibition of alpha- and beta-glucosidases; Arch. Biochem. Biophys, 230 668 2) Repp et al. (1985), The effects of processing inhibitors on N-linked oligosaccharides on the intracellular migration of glycoprotein E2 of mouse hepatitis virus and the maturation of coronavirus particles; J. Biol. Chem., 260 15873 3) Gruters et al. (1987), Interference with HIV-induced syncytium formation and viral infectivity by inhibitors of trimming glucosidase; Nature, 330 74 4) Franc et al. (1990), Effects of deoxymannojirimycin and castanospermine on the polarized secretion of thyroglobulin; Endocrinology, 126 1464 5) Pili et al. (1995), The alpha-glucosidase I inhibitor castanospermine alters endothelial cell glycosylation, prevents angiogenesis, and inhibits tumor growth; Mol. Cancer Res., 55 2920 6) Rhinehart et al. (1987), Castanospermine blocks the hyperglycemic response to carbohydrates in vivo: a result of intestinal disaccharidase inhibition; Life Sci., 41 2325

Properties of CASTANOSPERMINE

Melting point: 213-217 °C (lit.)
Boiling point: 421.9±45.0 °C(Predicted)
alpha  D25 +79.7° (c = 0.93 in water)
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 for CASTANOSPERMINE

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H312:Acute toxicity,dermal
H332:Acute toxicity,inhalation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P321:Specific treatment (see … on this label).
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

Computed Descriptors for CASTANOSPERMINE

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