Castanospermine

Castanospermine^[1][2]

Names
IUPAC name (1S,6S,7R,8R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,6,7,8-tetrol
Identifiers
CAS Number	79831-76-8
3D model (Jmol)	Interactive image
ChEBI	CHEBI:27860
ChEMBL	ChEMBL311226
ChemSpider	49177
ECHA InfoCard	100.127.469
PubChem	54445
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 Key: JDVVGAQPNNXQDW-TVNFTVLESA-N InChI=1/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 Key: JDVVGAQPNNXQDW-TVNFTVLEBE
SMILES O[C@H]1CCN2[C@H]1[C@@H](O)[C@H](O)[C@@H](O)C2
Properties
Chemical formula	C8H15NO4
Molar mass	189.209 g/mol
Appearance	White to off-white solid
Melting point	212 to 215 °C (414 to 419 °F; 485 to 488 K)
Solubility in water	Soluble
Hazards
R-phrases	R20/21/22
S-phrases	S26 S36
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Castanospermine is an indolizidine alkaloid first isolated from the seeds of Castanospermum australe.^[3] It is a potent inhibitor of some glucosidase enzymes^[4] and has antiviral activity in vitro and in mouse models.^[5]

Castanospermine was a lead to celgosivir.

See also

• Swainsonine

References

1. Merck Index, 11th Edition, 1902.
2. Castanospermine at Fermentek
3. Hohenschutz, Liza D.; Bell, E. Arthur; Jewess, Phillip J.; Leworthy, David P.; Pryce, Robert J.; Arnold, Edward; Clardy, Jon (1981). "Castanospermine, a 1,6,7,8-tetrahydroxyoctahydroindolizine alkaloid, from seeds of Castanospermum australe". Phytochemistry. 20 (4): 811–14. doi:10.1016/0031-9422(81)85181-3.
4. R Saul; J J Ghidoni; R J Molyneux & A D Elbein (1985). "Castanospermine inhibits alpha-glucosidase activities and alters glycogen distribution in animals". PNAS. 82 (1): 93–97. doi:10.1073/pnas.82.1.93. PMC 396977. PMID 3881759.
5. Whitby K, Pierson TC, Geiss B, Lane K, Engle M, Zhou Y, Doms RW, Diamond MS (2005). "Castanospermine, a potent inhibitor of dengue virus infection in vitro and in vivo". J Virol. 79 (14): 8698–706. doi:10.1128/JVI.79.14.8698-8706.2005. PMC 1168722. PMID 15994763.