Streptomyces deoxynojirimycin

Bellenamine, (R)-3,6-diamino-V-(aminomethyl)hexanamide is a (very) small-molecular-weight (MW 174) antibiotic produced by Streptomyces nashvillensis. It has only weak antibacterial activity but inhibits HIV-1 infection at an IC50 of 0.62 pg/ml (3.6 iM). With a CC50 of > 2 mg/ml (11.5 mM), the selectivity index of bellenamine can be estimated at well above 2000. Similarl to the well-established glycosylation inhibitors castanospermine and 1-deoxynojirimycin, bellenamine inhibits the secondary spread of HIV, although, unlike the glycosylation inhibitors, bellenamine had no apparent inhibitory effect on the glycosylation process. Therefore, its antiviral mechanism remains to be elucidated. 

Deoxynojirimycin (DNJ, 1) was originally prepared by catalytic hydrogenation of nojirimycin, which was discovered as the first glucose-mimicking antibiotic produced by Streptomyces spp., with a platinum catalyst or by chemical reduction with NaBH4 [5,6]. Later it was isolated from the root bark of mulberry trees and called moranoline [7]. DNJ is also produced by many strains in the genera Bacillus and Streptomyces [8,9]. 

Deoxynojirimycin (DNJ) (14) Streptomyces lavandulae subsp. trehalostaticus no. 2882 [21] Bacillus amyloliquefaciens, Bacillus polymyxa. Bacillus subtilis [22] Moms sp. (Moraceae) roots [10,23] Moms bombycis (Moraceae) leaves [9]... 

Deoxynojirimycin-2-O-, 3-0-, 4-0- a-D-ghicopyranosides and 2- 0-, 6-O-a-D-galactopyranosides and 2-0, 4-0-, 6-0-(3-D-glucopyranosides Morns alba (Moraceae) roots [ 10] Streptomyces lavandulae GC-148 [24]... 

Scheme 5. Biosynthesis of deoxymannojirimycin and deoxynojirimycin in Streptomyces subrulilis.

Streptomyces lavendulae SEN-158 (1-deoxynojirimycin), 106 Streptomyces lydicus PA-5726 (galactonojirimycin), 141 Streptomyces nojiriensis sp. SF-426 (nojirimycin), 105 Streptomyces roseochromogenes (anisomycin), 46... 

Glucose has been shown to be the biosynthetic (Hccursor of deoxynojirimycin and deoxymannnojirimycin in Streptomyces subrutilus. ... 

Subsequent calystegine isolations followed enrichment schemes that were developed for the isolation of other polyhydroxy alkaloids, such as swainsonine (5) and 1-deoxynojirimycin (6) from S. canescens (Fabaceae) (7) and from Streptomyces strains (31), respectively. Due to the hydrophilicity and the basic nature of those alkaloids, they were purified from aqueous extracts by a sequence of ion exchange resin columns that were designed to bind the alkaloids as cations, or to adsorb contaminating anions, while the alkaloids were eluted with water (Figure 3, method 2). An overview of the procedures was expertly summarised by Fellows and Fleet (32). Calystegines of the A-group are the most difficult to... 

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