Castanospermine

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^[1][2]

Names
Preferred IUPAC name (1S,6S,7R,8R,8aR)-Octahydroindolizine-1,6,7,8-tetrol
Identifiers
CAS Number	79831-76-8 Y[EBI]
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27860 Y
ChEMBL	ChEMBL311226 N
ChemSpider	49177 N
DrugBank	DB01816
ECHA InfoCard	100.127.469
EC Number	616-743-4
KEGG	C02256
PubChem CID	54445
UNII	Q0I3184XM7 Y
CompTox Dashboard (EPA)	DTXSID601026043
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 N Key: JDVVGAQPNNXQDW-TVNFTVLESA-N 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
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H332
Precautionary statements	P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

The castanospermine derivative celgosivir is an antiviral drug candidate that as of 2009 was in development for possible use in treating hepatitis C virus (HCV) infection.^[6]

Biosynthesis

L-Lysine undergoes a transamination to form α-aminoadipic acid. α-Aminoadipic acid undergoes a ring closure and then a reduction to form L-pipecolic acid.^[7][8][9]

Biosynthesis of castanospermine - pathway 1: transamination of L-Lys

In the alternate pathway L-Lys cyclizes and forms the enamine, which reduces to L-pipecolic acid.

HSCoA and then malonyl-CoA react in a Claisen reaction with L-pipecolic acid to form SCoA ester which undergoes a ring closure to form 1-indolizidinone. The carbonyl on 1-indolizidinone is reduced to the hydroxyl group. The molecule is then further hydroxylated to form the final product castanospermine.^[10]

Figure 2: Biosynthesis of castanospermine - pathway 2: cyclization of L-Lys to form pipecolic acid

See also

• Swainsonine