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Bioorg Med Chem ; 17(20): 7248-53, 2009 Oct 15.
Article in English | MEDLINE | ID: mdl-19775896

ABSTRACT

A new polyhydroxylated pyrrolizidine alkaloid designated as pochonicine (1) was isolated from a solid fermentation culture of the fungal strain Pochonia suchlasporia var. suchlasporia TAMA 87. The structure of 1 was determined using NMR and MS techniques as (1R*, 3S*, 5S*, 6S*, 7R*, 7a S*)-5-acetamidomethyl-3-hydroxymethyl-1,6,7-trihydroxypyrrolizidine. Pochonicine (1) showed potent inhibition against beta-N-acetylglucosaminidases (GlcNAcases) of various organisms including insects, fungi, mammals, and a plant but no inhibition against beta-glucosidase of almond, alpha-glucosidase of yeast, or chitinase of Bacillus sp. The GlcNAcase inhibitory activity of pochonicine (1) was comparable to nagstatin, a potent GlcNAcase inhibitor of natural origin.


Subject(s)
Acetylglucosaminidase/antagonists & inhibitors , Enzyme Inhibitors/pharmacology , Fungi/chemistry , Pyrrolizidine Alkaloids/pharmacology , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/isolation & purification , Fermentation , Gas Chromatography-Mass Spectrometry , Magnetic Resonance Spectroscopy , Pyrrolizidine Alkaloids/isolation & purification
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