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Isolation and SAR studies of bicyclic iminosugars from Castanospermum australe as glycosidase inhibitors.
- Source :
-
Phytochemistry . Mar2015, Vol. 111, p124-131. 8p. - Publication Year :
- 2015
-
Abstract
- We report the isolation and structural determination of fourteen iminosugars, containing five pyrrolizidines and five indolizidines, from Castanospermum australe . The structure of a new alkaloid was elucidated by spectroscopic methods as 6,8-di epi -castanospermine ( 13 ). Our side-by-side comparison between bicyclic and corresponding monocyclic iminosugars revealed that inhibition potency and spectrum against each enzyme are clearly changed by their core structures. Castanospermine ( 10 ) and 1-deoxynojirimycin (DNJ) have a common d - gluco configuration, and they showed the expected similar inhibition potency and spectrum. In sharp contrast, 6- epi -castanospermine ( 12 ) and 1-deoxymannojirimycin ( manno -DNJ) both have the d - manno configuration but the α-mannosidase inhibition of 6- epi -castanospermine ( 12 ) was much better than that of manno -DNJ. 6,8-Di epi -castanospermine ( 13 ) could be regarded as a bicyclic derivative of talo -DNJ, but it showed a complete loss of α-galactosidase A inhibition. This behavior against α-galactosidase A is similar to that observed for 1- epi -australine ( 6 ) and altro -DMDP. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00319422
- Volume :
- 111
- Database :
- Academic Search Index
- Journal :
- Phytochemistry
- Publication Type :
- Academic Journal
- Accession number :
- 101017560
- Full Text :
- https://doi.org/10.1016/j.phytochem.2014.12.011