Yeast glycogen synthase kinase-3beta pathway inhibitors from an organic extract of Streptomyces sp

J Nat Prod. 2009 Aug;72(8):1520-3. doi: 10.1021/np900163f.

Abstract

Investigation of a microbial fermentation organic extract of Streptomyces sp. H7667 led to the isolation of three new imides, 3-[(5E)-5-methyl-4-oxo-2-hydroxy-5-octenyl]glutarimide (1), 2-amino-N-2'-(phenylacetyl)propanimide (5), and 2-amino-N-(2'-(cyclohex-2''-enyl)acetyl)acetimide (6), and one new isoflavonoid glycoside, 6-O-methyl-7-O-alpha-rhamnopyranosyldaidzein (7), along with four known compounds. Their structures were elucidated by HRESIMS, 1H and 13C NMR, COSY, HMQC, HMBC, and NOESY spectra. Compounds 1-8 were evaluated for their inhibitory activities in the yeast glycogen synthase kinase-3beta assay.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glycogen Synthase Kinase 3 / antagonists & inhibitors*
  • Glycogen Synthase Kinase 3 beta
  • Imides / chemistry
  • Imides / isolation & purification*
  • Imides / pharmacology*
  • Molecular Structure
  • Saccharomyces cerevisiae / drug effects
  • Saccharomyces cerevisiae / enzymology*
  • Saccharomyces cerevisiae / metabolism
  • Streptomyces / chemistry*
  • Thiadiazoles / pharmacology

Substances

  • 4-benzyl-2-methyl-1,2,4-thiadiazolidine-3,5-dione
  • Imides
  • Thiadiazoles
  • Glycogen Synthase Kinase 3 beta
  • Glycogen Synthase Kinase 3