The chemical structure of 1-deoxynojirimycin, an example of a simple iminosugar.
An iminosugar, also known as an iminosaccharide, is any analog of a sugar where a nitrogen atom has replaced the oxygen atom in the ring of the structure.
Iminosugars are common components of plants and may be responsible for some of their medicinal properties.[1] The first iminosugar to be isolated from a natural source, 1-deoxynojirimycin (DNJ), found in Mulberry, was reported in 1976, but few others were discovered until many years later.[2]
In terms of biochemical activity for medicinal applications, DNJ and 1,4-dideoxy-1,4-imino-D-arabinitol (DAB, another early example of this class of compounds) are alpha-glucosidase inhibitors and were shown to have anti-diabetic and anti-viral activity. DNJ was modified to produce two derivatives now used as medicines, N-hydroxyethyl-DNJ (miglitol) for diabetes and N-butyl-DNJ (miglustat) for Gaucher's disease. Anti-cancer and anti-viral activity was subsequently observed for swainsonine—a mannose analogue—and castanospermine—a glucose analogue—in the 1980s.[3] More than 200 have now been reported from plants and micro-organisms. Although the early compounds had biological activities due to glycosidase inhibition, an increasing number are being shown to have therapeutic potential without being glycosidase inhibitors and may interact with sugar receptors in the body or chaperone deficient enzymes such as in lysosomal storage disorders or in cystic fibrosis.[2]
An iminosugar, also known as an iminosaccharide, is any analog of a sugar where a nitrogen atom has replaced the oxygen atom in the ring of the structure...
strains of streptomycetes, e.g. Streptomyces azureus. Nojirimycin, an iminosugar from a class of Streptomyces species. Tetrodotoxin, a neurotoxin produced...
due to various mutations, one of which is called N370S. Afegostat, an iminosugar, binds selectively to N370S glucocerebrosidase and restores its correct...
mainly obtained from a class of Streptomyces species. Chemically, it is an iminosugar. 1-deoxynojirimycin or duvoglustat 1-deoxygalactonojirimycin or migalastat...
has a nitrogen atom in the ring instead of an oxygen, which makes it an iminosugar. The structure is formally derived from nojirimycin.[citation needed]...
Castanospermine is an indolizidine alkaloid first isolated from the seeds of Castanospermum australe. It is a potent inhibitor of some glucosidase enzymes...
doesn't work; this is called substrate reduction therapy. Miglustat is an iminosugar, a synthetic analogue of D-glucose and a white to off-white crystalline...
Swainsonine is an indolizidine alkaloid. It is a potent inhibitor of Golgi alpha-mannosidase II, an immunomodulator, and a potential chemotherapy drug...
can be absorbed by the body. Miglitol, and other structurally-related iminosugars, inhibit glycoside hydrolase enzymes called alpha-glucosidases. Since...
from the seeds. Members of this and closely related genera accumulate iminosugars in their leaves. Due to its importance as a food, the blackbean tree...
collectively as pyrrolizidine alkaloids. It is one of five classes of iminosugars. These are often synthesized from a carbohydrate. Pyrrolizidine alkaloids...
ISBN 978-981-4303-48-4. editors; Compain, Philippe; Martin, Olivier R. (2007). Iminosugars from synthesis to therapeutic applications. Chichester, West Sussex,...
gardens. Members of this genus accumulate hydroxypipecolic acids and iminosugars in their leaves. Xanthocercis Baill. Plants of the World Online. Retrieved...
Celgosivir, in development by Migenix for the treatment of hepatitis C virus (HCV) infection, is an oral prodrug of the natural product castanospermine...
called carbasugars or C-glycosides, thiosugars or thioglycosides, or iminosugars or glycosylamines. When nitrogen is introduced, the glycomimetic may...
De Wild. Members of this genus accumulate hydroxypipecolic acids and iminosugars in their leaves. Angylocalyx Taub. Plants of the World Online. Retrieved...
stamens and gynoecium exserted." Also, members of this tribe accumulate iminosugars in their leaves, whereas other members of the ADA clade do not. Cardoso...
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