Pochonicine, a polyhydroxylated pyrrolizidine alkaloid from fungus Pochonia suchlasporia var. suchlasporia TAMA 87 as a potent β-N-acetylglucosaminidase inhibitor

Hirokazu Usuki, Miho Toyo-oka, Hiroshi Kanzaki, Toru Okuda, Teruhiko Nitoda

Research output: Contribution to journalArticle

39 Citations (Scopus)

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 β-N-acetylglucosaminidases (GlcNAcases) of various organisms including insects, fungi, mammals, and a plant but no inhibition against β-glucosidase of almond, α-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.

Original languageEnglish
Pages (from-to)7248-7253
Number of pages6
JournalBioorganic and Medicinal Chemistry
Volume17
Issue number20
DOIs
Publication statusPublished - Oct 15 2009

Fingerprint

Pyrrolizidine Alkaloids
Acetylglucosaminidase
Fungi
Glucosidases
Chitinases
Mammals
Bacilli
Yeast
Fermentation
Bacillus
Insects
Yeasts
Nuclear magnetic resonance
5-acetamidomethyl-3-hydroxymethyl-1,6,7-trihydroxypyrrolizidine

Keywords

  • Chitinolytic enzyme system
  • Enzyme inhibitor
  • Family 18 chitinase
  • Family 20 GlcNAcase
  • Metabolic turnover of chitin

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry

Cite this

Pochonicine, a polyhydroxylated pyrrolizidine alkaloid from fungus Pochonia suchlasporia var. suchlasporia TAMA 87 as a potent β-N-acetylglucosaminidase inhibitor. / Usuki, Hirokazu; Toyo-oka, Miho; Kanzaki, Hiroshi; Okuda, Toru; Nitoda, Teruhiko.

In: Bioorganic and Medicinal Chemistry, Vol. 17, No. 20, 15.10.2009, p. 7248-7253.

Research output: Contribution to journalArticle

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