Pochonicine, a polyhydroxylated pyrrolizidine alkaloid from fungus Pochonia suchlasporia var. suchlasporia TAMA 87 as a potent beta-N-acetylglucosaminidase inhibitor.
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.
Usuki
Hirokazu
H
Laboratory of Bioresources Chemistry, The Graduate School of Natural Science and Technology, Okayama University, Okayama 700-8530, Japan.
Toyo-oka
Miho
M
Kanzaki
Hiroshi
H
Okuda
Toru
T
Nitoda
Teruhiko
T
D000118:Acetylglucosaminidase / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005285:Fermentation; D005658:Fungi / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D011763:Pyrrolizidine Alkaloids / Q000302:isolation & purification / Q000494:pharmacology*
C546440:5-acetamidomethyl-3-hydroxymethyl-1,6,7-trihydroxypyrrolizidine; D004791:Enzyme Inhibitors; D011763:Pyrrolizidine Alkaloids; D000118:Acetylglucosaminidase