From Castanospermum austral

Castanospermine (6), isolated from Castanospermum australe by Ho-henschutz and coworkers and characterized as a strong inhibitor for )S-d-... 

R. J. Molyneux, M. Benson, R. Y. Wong, J. E. Tropea, and A. D. Elbein, Australine, a novel pyrrolizidine alkaloid glucosidase inhibitor from Castanospermum australe, J. Nat. Prod., 51 (1988) 1198-1206. 

Alternatively, the diastereomeric mixture of aldol adducts undergoes lithium aluminum hydride reduction, primary alcohol silylation, and chromatographic separation to afford 291. Subsequent Mitsunobu inversion at C-3 to furnish the j -alcohol 292 followed by a depro-tective sequence and ring closure provides (+ )-castanospermine (293). This poly-hydroxylated indolizidine alkaloid isolated from Castanospermum australe and Alexa leipetala is a potent inhibitor of various a- and j8-glucosidases [98] (Scheme 68). 

A more complex alkaloid, swainsonine (40) (from Swain-sona species, Fabaceae), also inhibits a-mannosidase activity. A similar complex alkaloid, castanospermine (41) (from Castanospermum australe, Fabaceae) inhibits 3-glucosi-dases [but not a-glucosidases as in (38)] (Fellows, 1987 Fellows et al., 1992). 

Hohenschntz ED, Bell EA, Jewess PJ, Leworthy DP, Pryce RJ, Arnold E, Clardy J. (1981) Castanospermine, a 1,6,7,8-tetrahydroxyoctahydroin-dolizine alkaloid, from seeds of Castanospermum australe. Phytochemistry 20 811-814. 

This compound exhibits the same relationship to (3-D-fructofuranose as 1-deoxy-nojirimcin does to D-glucopyranose. In 1979, a polyhydroxyindolizidine alkaloid was isolated from the poisonous fruit of Castanospermum australe, a handsome Australian indigenous tree, and coined castanospermine (8) after its source.28 A compound subsequently isolated from the seeds of this plant was the pyrrolizidine australine (9),29 also found in Alexa leiopetala,30 along with other compounds. These discoveries increasingly supported the hypothesis that imino sugars and their structural relatives might be a fairly common family of natural products, and their widespread... 

Castanospermine, a new alkaloid isolated from toxic seeds of the Australian legume Castanospermum australe, has been shown to be 8a/Tindolizidine-lcr,6/ ,7cr,8/ -tetraol (1). The structure and relative configuration were determined by X-ray crystallography.1... 

Castanospermine, isolated from the seeds of Castanospermum australe and from dried pods of Alexa leiopetala [6], is another polyhydroxylated indolizidine v th a potent, competitive and reversible inhibitory effect on several glycosidases. For this reason it has been largely used as a glycosidase identifier and as an auxiliary in the purification of glycosidases and mannosidases [120-125]. Castanospermine was also used in two other... 

Castanospermine (239) was originally isolated from seeds of the Australian legume Castanospermum australe (the Moreton Bay chestnut), and later from plants of the South American genus Alexa, which is also a member of the Leguminosae. Two minor diastereomers of ( + )-239, viz. (+ )-6-epicastanospermine (240) and (+ )-6,7-diepicastanospermine (241), were subsequently isolated from C. australe. Castanospermine owes its status as one of the most widely-investigated... 

An additional minor alkaloid isolated from the seeds of Castanospermum australe has proved to be (+ )-7-deoxy-6-epicastanospennine (242) ([a]o +18.3 , c... 

Castanogenol (184), from the bark of Castanospermum australe, has been prepared by lithium aluminium hydride reduction of bayogenin methyl ester (18 5). The structure of entagenic acid (186) has been revised. The vicinal glycol... 

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