Castanospermine

Structural formula
General
Surname	Castanospermine
other names	(1 S , 6 S , 7 R , 8 R , 8a R ) -1,6,7,8-tetrahydroxyindolizidine
Molecular formula	C 8 H 15 NO 4
Brief description	white solid
External identifiers / databases
EC number	616-743-4
ECHA InfoCard	100.127.469
PubChem	54445
ChemSpider	49177
DrugBank	DB01816
Wikidata	Q753104
properties
Molar mass	189.21 g mol −1
Physical state	firmly
Melting point	213-217 ° C
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-312-332
	P: 301 + 330 + 331-312-280-302 + 352-304 + 340
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Castanospermin is a poisonous alkaloid from the group of polyhydroxy alkaloids . It forms large white cubic crystals .

Occurrence

Australian legume tree

Castanospermine is found in the seeds of the Australian legume tree Castanospermum australe , from which it can also be extracted.

properties

Castanospermine inhibits α- and β- glucosidases , but is not as specific as the structurally related swainsonine . Also causes castanospermine accumulation of hochmannosylierten glycoproteins , such as in Concanavalin A .

Castanospermine works against AIDS viruses. It changes the surface glycoproteins of the HI virus (glycoprotein processing) so that the virus can no longer attach to the host cells ( T4 lymphocytes ) or reproduce. Furthermore, castanospermin has activity against cancer cells and herpes viruses . As a prodrug of castanospermine, celgosivir (6- O- butyrylcastanospermine) has been clinically investigated for the treatment of infections with the hepatitis C virus (HCV) and the dengue virus .

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet Castanospermine at AlfaAesar, accessed on June 3, 2020 ( PDF )(JavaScript required) .
↑ Rudolf Hänsel, Otto Sticher (Ed.): Pharmakognosie - Phytopharmazie . 9th edition. January 2, 2010, p. 1262 .
↑ ^a ^b ^c Entry on castanospermine. In: Römpp Online . Georg Thieme Verlag, accessed on June 3, 2020.
↑ Drug Profile Celgosivir on adisinsight.com, accessed July 8, 2020.

[Alfa-1] ↑ ^a ^b ^c ^d ^e data sheet Castanospermine at AlfaAesar, accessed on June 3, 2020 ( PDF )(JavaScript required) .

[2] Rudolf Hänsel, Otto Sticher (Ed.): Pharmakognosie - Phytopharmazie . 9th edition. January 2, 2010, p. 1262 .

[Römpp-3] Entry on castanospermine. In: Römpp Online . Georg Thieme Verlag, accessed on June 3, 2020.

[4] Drug Profile Celgosivir on adisinsight.com, accessed July 8, 2020.