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.
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http://dx.doi.org/10.1006/bbrc.1996.0427 | DOI Listing |
ACS Omega
February 2020
Department of Chemistry, Occidental College, 1600 Campus Rd. M-5, Los Angeles, California 90041, United States.
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 PDFAppl 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 PDFJ Org Chem
June 2016
Departament de Química Analítica i Química Orgànica, Facultat de Química, Universitat Rovira i Virgili, C/Marcel·lí Domingo no. 1,43007 Taragona, Spain.
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 PDFAMB 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.
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