Pestalazines and pestalamides, bioactive metabolites from the plant pathogenic fungus Pestalotiopsis theae

J Nat Prod. 2008 Nov;71(11):1861-5. doi: 10.1021/np800357g. Epub 2008 Oct 15.

Abstract

Pestalazines A (1) and B (2), two new diketopiperazine heterodimers, and pestalamides A-C (3-5), three new amides, have been isolated from cultures of the plant pathogenic fungus Pestalotiopsis theae. The structures of these compounds were elucidated mainly by NMR spectroscopy. The absolute configurations of 1 and 2 were determined using Marfey's method on their acid hydrolysates and by comparison of their CD spectra with that of a model compound. Compounds 1, 3, and 6 displayed inhibitory effects on HIV-1 replication in C8166 cells. Compound 3 also showed potent antifungal activity against Aspergillus fumigatus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / isolation & purification*
  • Anti-HIV Agents / pharmacology*
  • Ascomycota / chemistry*
  • Aspergillus fumigatus / drug effects
  • Camellia sinensis / microbiology
  • Diketopiperazines / chemistry
  • Diketopiperazines / isolation & purification*
  • Diketopiperazines / pharmacology*
  • Humans
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / isolation & purification*
  • Indole Alkaloids / pharmacology*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular

Substances

  • Anti-HIV Agents
  • Diketopiperazines
  • Indole Alkaloids
  • pestalazine A
  • pestalazine B