CASTANOSPERMINE
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03754 |
| CAS | 79831-76-8 |
| Molecular Weight | 189.21 |
| Molecular Formula | C8H15NO4 |
| Purity | >98% |
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Description
Castanospermine is an inhibitor of all forms of α- and β-glucosidases, especially glucosidase l. It inhibits lysosomal and neutral α-glucosidases with Ki values of 0.1 and 10 μM, respectively. It also inhibits lysosomal and cytosolic β-glucosidases with Ki values of 7 and 40 μM, respectively. It inhibits HIV syncytium formation and replication. It catalyzes the cleavage of individual glucosyl residues from various glycoconjugates, including complex carbohydrates and glycoproteins. It is effective both in vitro and in vivo. It blocks N-linked glycosylation during post-translational modification of proteins, affecting protein trafficking and cell functions, including angiogenesis. It also interferes with viral replication and infection. It is a potent and specific inhibitor of mammalian and plant α-and β-D-glucosidases in vitro.
Specification
| Synonyms | 1,6,7,8-Tetrahydroxyoctahydroindolizine |
| Shelf Life | 2 month in rt, long time |
| Storage | Store at -20°C |
| IUPAC Name | (1S,6S,7R,8R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,6,7,8-tetrol |
| Canonical SMILES | C1CN2CC(C(C(C2C1O)O)O)O |
| 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 |
| InChI Key | JDVVGAQPNNXQDW-TVNFTVLESA-N |
| Source | Castanospermum australe (plant extract) |
Properties
| Appearance | White to Yellow Powder |
| Application | Castanospermine inhibits HIV syncytium formation and replication. It catalyzes the cleavage of individual glucosyl residues from various glycoconjugates, including complex carbohydrates and glycoproteins. It blocks N-linked glycosylation during post-translational modification of proteins, affecting protein trafficking and cell functions, including angiogenesis. It also interferes with viral replication and infection. |
| Boiling Point | 421.9±45.0°C |
| Melting Point | 202-208°C (dec.) |
| Density | 1.53±0.1 g/cm3 |
| Solubility | Soluble in DMSO, Water |
Reference Reading
1.The toxicity of Castanospermum australe seeds for cattle.
McKenzie RA1, Reichmann KG, Dimmock CK, Dunster PJ, Twist JO. Aust Vet J. 1988 Jun;65(6):165-7.
Two calves given a mean of 16.1 g and 16.4 g ripe Castanospermum australe seeds/kg body weight daily for 13 and 16 days respectively developed haemorrhagic gastroenteritis. The first calf died. The second calf had mild myocardial degeneration and necrosis and mild nephrosis at necropsy. Two calves given a mean of 16.8 g unripe C. australe seeds/kg body weight daily for 18 days remained clinically normal and had mild gastritis at necropsy. The activity of alpha-glucosidase was reduced in the mononuclear cells of peripheral blood and in skeletal muscle. This was attributed to the presence of the indolizidine alkaloid, castanospermine, in the seeds. The toxin causing the gastroenteritis and other lesions is unknown.
2.The influence of indigenous food procurement techniques on populations of cyanobacteria in pre-European Australia: a potential small-scale water amelioration tool.
Sadgrove NJ1. Ecohealth. 2009 Sep;6(3):390-403. doi: 10.1007/s10393-010-0276-3. Epub 2010 Jan 27.
During times of pre-European Australia, indigenous people utilized methods of food procurement that resulted in toxic phytochemicals from plants entering their waterholes. This paper focuses on three of these plants, namely the leaves of Acacia colei and Duboisia hopwoodii, which were used by hunters to poison water holes to stun fish or a drinking animal, and the seeds of Castanospermum australe, which were eaten following the leaching of toxins into a running stream. If consumed by humans, the main toxins from these plants--saponins/sesquiterpenes, nicotine/nornicotine, and australine/castanospermine--are fatal. However, it is undetermined whether populations of Cyanobacteria also can be affected. During this study, the previously mentioned plants were administered to populations of the species Anabaena circinalis, Microcystis aeruginosa, and Nodularia spumigena, while mimicking the traditional applications of these plants as closely as possible.
3.The effects of castanospermine and swainsonine on the activity and synthesis of intestinal sucrase.
Pan YT1, Ghidoni J, Elbein AD. Arch Biochem Biophys. 1993 May 15;303(1):134-44.
Castanospermine is an indolizidine alkaloid that is found in the seeds of the Australian tree Castanospermum australe. These seeds have been reported to be toxic to animals and to cause severe gastrointestinal upset. In order to determine whether castanospermine is responsible for this toxicity, the alkaloid was injected into young mice or rats, and its effects on various intestinal disaccharidases were determined. Another indolizidine alkaloid, the alpha-mannosidase inhibitor swainsonine, was also tested to compare its effects to those of castanospermine. Castanospermine strongly and rapidly inhibited the activity of the disaccharidases, sucrase, maltase, and trehalase, with sucrase being the most sensitive to inhibition. The loss of activity of these enzymes, especially sucrase, in injected animals appeared to be due to a direct inhibition of enzyme activity, rather than to a change in the structure of the glycan chains of the enzyme, since only minor alterations in carbohydrates were observed.
4.Antihyperglycemic activity with DPP-IV inhibition of alkaloids from seed extract of Castanospermum australe: Investigation by experimental validation and molecular docking.
Bharti SK1, Krishnan S, Kumar A, Rajak KK, Murari K, Bharti BK, Gupta AK. Phytomedicine. 2012 Dec 15;20(1):24-31. doi: 10.1016/j.phymed.2012.09.009. Epub 2012 Oct 10.
The antidiabetic actions of Castanospermum australe Cunn., seed (CAS) extract were evaluated in Poloxamer-407 (PX-407) induced T2DM rats. The CAS extract (100 and 150 mg/kg body weight) was administered orally once a day for 5 weeks after the animals were confirmed diabetic. A significant increase in blood glucose, HbA₁c and serum insulin levels were observed in T2DM rats in comparison to citrate control rats. Treatment with CAS extract in T2DM rats reduced the elevated levels of blood glucose, HbA₁c and insulin with significant (p≤0.001) improvement in OGT. The CAS extract treatment also increased (p≤0.001) the K(ITT) and prevented increase in HOMA-R level in T2DM rats. The DPP-IV inhibitory potential of CAS extract showed IC₅₀ value of 13.96 μg/ml whilst the standard Diprotin A displayed the IC₅₀ value of 1.543 μg/ml. Molecular docking of the three reported alkaloids from the seeds of C. australe showed comparable DPP-IV inhibition with berberine.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
