Azaphilones and p-terphenyls from the mangrove endophytic fungus Penicillium chermesinum (ZH4-E2) isolated from the South China Sea

J Nat Prod. 2011 May 27;74(5):997-1002. doi: 10.1021/np100889v. Epub 2011 Apr 21.

Abstract

Eight secondary metabolites, including three new azaphilones (chermesinones A-C, 1-3), three new p-terphenyls (6'-O-desmethylterphenyllin, 4; 3-hydroxy-6'-O-desmethylterphenyllin, 5; 3''-deoxy-6'-O-desmethylcandidusin B, 7), and two known p-terphenyls (6, 8), were isolated from the culture of the mangrove endophytic fungus Penicillium chermesinum (ZH4-E2). Their structures were established by spectroscopic analysis. The absolute configuration of 1 was determined by X-ray crystallography. Terphenyls 4, 5, and 6 exhibited strong inhibitory effects against α-glucosidase with IC50 values of 0.9, 4.9, and 2.5 μM, respectively. Terphenyls 7 and 8 showed inhibitory activity toward acetylcholinesterase with IC50 values of 7.8 and 5.2 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzopyrans / chemistry
  • Benzopyrans / isolation & purification*
  • Benzopyrans / pharmacology
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / isolation & purification*
  • Cholinesterase Inhibitors / pharmacology*
  • Crystallography, X-Ray
  • Glycoside Hydrolase Inhibitors*
  • Inhibitory Concentration 50
  • Molecular Structure
  • Oceans and Seas
  • Penicillium chrysogenum / chemistry*
  • Pigments, Biological / chemistry
  • Pigments, Biological / isolation & purification*
  • Pigments, Biological / pharmacology
  • Rhizophoraceae / microbiology
  • Terphenyl Compounds / chemistry
  • Terphenyl Compounds / isolation & purification*
  • Terphenyl Compounds / pharmacology

Substances

  • Benzopyrans
  • Cholinesterase Inhibitors
  • Glycoside Hydrolase Inhibitors
  • Pigments, Biological
  • Terphenyl Compounds
  • azaphilone