Nectrisine, discovered as an immunomodulator, was found to inhibit alpha-glucosidase, alpha- and beta-mannosidases, beta-glucosidase and beta-N-acetylglucosaminidase, in that order of inhibition strength. Beta-Galactosidase, alpha-fucosidase, and neuraminidase were insensitive to this antibiotic. Also sensitive was the trimming glucosidase I which participates in the first step of modifying N-glycosidic oligosaccharide. Nectrisine demonstrated an inhibitory effect at the cellular level as strong as expected based on its action at enzyme levels; castanospermine and 1-deoxynojirimycin did not. Nectrisine and castanospermine suppressed syncytium formation and hemolytic activity in Newcastle disease virus (NDV)-infected BHK cells, without blocking the synthesis and cell-surface expression of HANA glycoprotein of NDV.

Download full-text PDF

Source
http://dx.doi.org/10.1006/bbrc.1996.0427DOI Listing

Publication Analysis

Top Keywords

nectrisine
4
nectrisine potent
4
potent inhibitor
4
inhibitor alpha-glucosidases
4
alpha-glucosidases demonstrating
4
demonstrating activities
4
activities enzyme
4
enzyme cellular
4
cellular levels
4
levels nectrisine
4

Similar Publications

Article Synopsis
  • The enantioselective syntheses of (-)-coniine, DAB-1, and nectrisine were achieved using a combination of enzyme-catalyzed and transition metal-catalyzed reactions.
  • Initial stereocenter creation was highly efficient, achieving over 99% enantioselectivity through enzyme-catalyzed hydrocyanation.
  • Challenges with natural enzyme compatibility were addressed by incorporating ruthenium-catalyzed olefin metathesis and employing palladium-catalyzed reactions to produce the desired piperidine and pyrrolidine alkaloid products.
View Article and Find Full Text PDF

Functional Analysis of a Gene Cluster from Involved in Biosynthesis of the Pyrrolidine Azasugar DAB-1.

J Nat Prod

December 2019

Department of Chemistry , University of Florida, Gainesville , Florida 32611-7200 , United States.

Azasugars, "nitrogen in the ring" analogues of monosaccharides, are known to be distributed in select plant, fungal. and bacterial species. We identify DSM 2588 as the first bacterial source of the plant pyrrolidine azasugar 1,4-dideoxy-1,4-aminoarabinitol (DAB-1).

View Article and Find Full Text PDF

Nectrisine Biosynthesis Genes in Thelonectria discophora SANK 18292: Identification and Functional Analysis.

Appl Environ Microbiol

November 2016

CMC Planning Department, Pharmaceutical Technology Division, Daiichi Sankyo Co., Ltd., Hiratsuka, Kanagawa, Japan.

Unlabelled: The fungus Thelonectria discophora SANK 18292 produces the iminosugar nectrisine, which has a nitrogen-containing heterocyclic 5-membered ring and acts as a glycosidase inhibitor. In our previous study, an oxidase (designated NecC) that converts 4-amino-4-deoxyarabinitol to nectrisine was purified from T. discophora cultures.

View Article and Find Full Text PDF

A formal enantioselective synthesis of nectrisine, a potent α-glucosidase inhibitor, was carried out starting from butadiene monoepoxide through a synthetic sequence involving enantioselective allylic substitution, cross-metathesis, dihydroxylation, and cyclization.

View Article and Find Full Text PDF

Characterization of a novel oxidase from Thelonectria discophora SANK 18292 involved in nectrisine biosynthesis.

AMB Express

March 2016

CM&C Planning Department, Pharmaceutical Technology Division, Daiichi Sankyo Co., Ltd., 1-12-1, Shinomiya, Kanagawa, Hiratsuka-shi, 254-0014, Japan.

A fungus, Thelonectria discophora SANK 18292 (JCM 30947), produces nectrisine that has a nitrogen-containing heterocyclic 5-membered ring acting as a glycosidase inhibitor. Our previous study showed the possibility that 4-amino-4-deoxyarabinitol was enzymatically converted to nectrisine but the enzyme was not known. In order to characterize the enzyme, which is designated as NecC, it was purified from the fungus using ammonium sulfate precipitation and anion exchange chromatography.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!